Physical-Chemical Properties and Environmental Fate for Organic Chemicals
Second Edition HANDBOOK OF © 2006 by Taylor & Francis Group, LLC Volume I Introduction and Hydrocarbons Volume II Halogenated Hydrocarbons Volume III Oxygen Containing Compounds Volume IV Nitrogen and Sulfur Containing Compounds and Pesticides A CRC title, part of the Taylor & Francis imprint, a member of the Taylor & Francis Group, the academic division of T&F Informa plc. Boca Raton London New York Physical-Chemical Properties and Environmental Fate for Organic Chemicals Volume I Introduction and Hydrocarbons Donald Mackay Wan Ying Shiu Kuo-Ching Ma Sum Chi Lee Second Edition HANDBOOK OF Volume II Halogenated Hydrocarbons Volume III Oxygen Containing Compounds Volume IV Nitrogen and Sulfur Containing Compounds and Pesticides © 2006 by Taylor & Francis Group, LLC Published in 2006 by CRC Press Taylor & Francis Group 6000 Broken Sound Parkway NW, Suite 300 Boca Raton, FL 33487-2742 © 2006 by Taylor & Francis Group, LLC CRC Press is an imprint of Taylor & Francis Group No claim to original U.S. Government works Printed in the United States of America on acid-free paper 10 9 8 7 6 5 4 3 2 1 International Standard Book Number-10: 1-56670-687-4 (Hardcover) International Standard Book Number-13: 978-1-56670-687-2 (Hardcover) Library of Congress Card Number 2005051402 This book contains information obtained from authentic and highly regarded sources. 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For organizations that have been granted a photocopy license by the CCC, a separate system of payment has been arranged. Trademark Notice: Product or corporate names may be trademarks or registered trademarks, and are used only for identification and explanation without intent to infringe. Library of Congress Cataloging-in-Publication Data Handbook of physical-chemical properties and environmental fate for organic chemicals.--2nd ed. / by Donald Mackay ... [et al.]. p. cm. Rev. ed. of: Illustrated handbook of physical-chemical properties and environmental fate for organic chemicals / Donald Mackay, Wan Ying Shiu, and Kuo Ching Ma. c1992-c1997. Includes bibliographical references and index. ISBN 1-56670-687-4 (set : acid-free paper) 1. Organic compounds--Environmental aspects--Handbooks, manuals, etc. 2. Environmental chemistry--Handbooks, manuals, etc. I. Mackay, Donald, 1936- II. Mackay, Donald, 1936- Illustrated handbook of physical-chemical properties and environmental fate for organic chemicals. TD196.O73M32 2005 628.5'2--dc22 2005051402 Visit the Taylor & Francis Web site at http://www.taylorandfrancis.com and the CRC Press Web site at http://www.crcpress.com Taylor & Francis Group is the Academic Division of T&F Informa plc. © 2006 by Taylor & Francis Group, LLC Preface This handbook is a compilation of environmentally relevant physical-chemical data for similarly structured groups of chemical substances. These data control the fate of chemicals as they are transported and transformed in the multimedia environment of air, water, soils, sediments, and their resident biota. These fate processes determine the exposure experienced by humans and other organisms and ultimately the risk of adverse effects. The task of assessing chemical fate locally, regionally, and globally is complicated by the large (and increasing) number of chemicals of potential concern; by uncertainties in their physical-chemical properties; and by lack of knowledge of prevailing environmental conditions such as temperature, pH, and deposition rates of solid matter from the atmosphere to water, or from water to bottom sediments. Further, reported values of properties such as solubility are often in conflict. Some are measured accurately, some approximately, and some are estimated by various correlation schemes from molecular structures. In some cases, units or chemical identity are wrongly reported. The user of such data thus has the difficult task of selecting the “best” or “right” values. There is justifiable concern that the resulting deductions of environmental fate may be in substantial error. For example, the potential for evaporation may be greatly underestimated if an erroneously low vapor pressure is selected. To assist the environmental scientist and engineer in such assessments, this handbook contains compilations of physical-chemical property data for over 1000 chemicals. It has long been recognized that within homologous series, properties vary systematically with molecular size, thus providing guidance about the properties of one substance from those of its homologs. Where practical, plots of these systematic property variations can be used to check the reported data and provide an opportunity for interpolation and even modest extrapolation to estimate unmeasured properties of other substances. Most handbooks treat chemicals only on an individual basis and do not contain this feature of chemicalto- chemical comparison, which can be valuable for identifying errors and estimating properties. This most recent edition includes about 1250 compounds and contains about 30 percent additional physical-chemical property data. There is a more complete coverage of PCBs, PCDDs, PCDFs, and other halogenated hydrocarbons, especially brominated and fluorinated substances that are of more recent environmental concern. Values of the physical-chemical properties are generally reported in the literature at a standard temperature of 20 or 25°C. However, environmental temperatures vary considerably, and thus reliable data are required on the temperature dependence of these properties for fate calculations. A valuable enhancement to this edition is the inclusion of extensive measured temperature-dependent data for the first time. The data focus on water solubility, vapor pressure, and Henry’s law constant but include octanol/water and octanol/air partition coefficients where available. They are provided in the form of data tables and correlation equations as well as graphs. We also demonstrate in Chapter 1 how the data may be taken a stage further and used to estimate likely environmental partitioning tendencies, i.e., how the chemical is likely to become distributed between the various media that comprise our biosphere. The results are presented numerically and pictorially to provide a visual impression of likely environmental behavior. This will be of interest to those assessing environmental fate by confirming the general fate characteristics or behavior profile. It is, of course, only possible here to assess fate in a “typical” or “generic” or “evaluative” environment. No claim is made that a chemical will behave in this manner in all situations, but this assessment should reveal the broad characteristics of behavior. These evaluative fate assessments are generated using simple fugacity models that flow naturally from the compilations of data on physical-chemical properties of relevant chemicals. Illustrations of estimated environmental fate are given in Chapter 1 using Levels I, II, and III mass balance models. These and other models are available for downloading gratis from the website of the Canadian Environmental Modelling Centre at Trent University (www.trent.ca/cemc). It is hoped that this new edition of the handbook will be of value to environmental scientists and engineers and to students and teachers of environmental science. Its aim is to contribute to better assessments of chemical fate in our multimedia environment by serving as a reference source for environmentally relevant physical-chemical property data of classes of chemicals and by illustrating the likely behavior of these chemicals as they migrate throughout our biosphere. © 2006 by Taylor & Francis Group, LLC Acknowledgments We would never have completed the volumes for the first and second editions of the handbook and the CD-ROMs without the enormous amount of help and support that we received from our colleagues, publishers, editors, friends, and family. We are long overdue in expressing our appreciation. We would like first to extend deepest thanks to these individuals: Dr. Warren Stiver, Rebecca Lun, Deborah Tam, Dr. Alice Bobra, Dr. Frank Wania, Ying D. Lei, Dr. Hayley Hung, Dr. Antonio Di Guardo, Qiang Kang, Kitty Ma, Edmund Wong, Jenny Ma, and Dr. Tom Harner. During their past and present affiliations with the Department of Chemical Engineering and Applied Chemistry and/or the Institute of Environment Studies at the University of Toronto, they have provided us with many insightful ideas, constructive reviews, relevant property data, computer know-how, and encouragement, which have resulted in substantial improvements to each consecutive volume and edition through the last fifteen years. Much credit goes to the team of professionals at CRC Press/Taylor & Francis Group who worked on this second edition. Especially important were Dr. Fiona Macdonald, Publisher, Chemistry; Dr. Janice Shackleton, Input Supervisor; Patrica Roberson, Project Coordinator; Elise Oranges and Jay Margolis, Project Editors; and Marcela Peres, Production Assistant. We are indebted to Brian Lewis, Vivian Collier, Kathy Feinstein, Dr. David Packer, and Randi Cohen for their interest and help in taking our idea of the handbook to fruition. We also would like to thank Professor Doug Reeve, Chair of the Department of Chemical Engineering and Applied Chemistry at the University of Toronto, as well as the administrative staff for providing the resources and assistance for our efforts. We are grateful to the University of Toronto and Trent University for providing facilities, to the Natural Sciences and Engineering Research Council of Canada and the consortium of chemical companies that support the Canadian Environmental Modelling Centre for funding of the second edition. It is a pleasure to acknowledge the invaluable contributions of Eva Webster and Ness Mackay. © 2006 by Taylor & Francis Group, LLC Biographies Donald Mackay, born and educated in Scotland, received his degrees in Chemical Engineering from the University of Glasgow. After working in the petrochemical industry he joined the University of Toronto, where he taught for 28 years in the Department of Chemical Engineering and Applied Chemistry and in the Institute for Environmental Studies. In 1995 he moved to Trent University to found the Canadian Environmental Modelling Centre. Professor Mackay’s primary research is the study of organic environmental contaminants, their properties, sources, fates, effects, and control, and particularly understanding and modeling their behavior with the aid of the fugacity concept. His work has focused especially on the Great Lakes Basin; on cold northern climates; and on modeling bioaccumulation and chemical fate at local, regional, continental and global scales. His awards include the SETAC Founders Award, the Honda Prize for Eco-Technology, the Order of Ontario, and the Order of Canada. He has served on the editorial boards of several journals and is a member of SETAC, the American Chemical Society, and the International Association of Great Lakes Research. Wan-Ying Shiu is a Senior Research Associate in the Department of Chemical Engineering and Applied Chemistry, and the Institute for Environmental Studies, University of Toronto. She received her Ph.D. in Physical Chemistry from the Department of Chemistry, University of Toronto, M.Sc. in Physical Chemistry from St. Francis Xavier University, and B.Sc. in Chemistry from Hong Kong Baptist College. Her research interest is in the area of physical-chemical properties and thermodynamics for organic chemicals of environmental concern. Kuo-Ching Ma obtained his Ph.D. from Florida State University, M.Sc. from The University of Saskatchewan, and B.Sc. from The National Taiwan University, all in Physical Chemistry. After working many years in the aerospace, battery research, fine chemicals, and metal finishing industries in Canada as a Research Scientist, Technical Supervisor/ Director, he is now dedicating his time and interests to environmental research. Sum Chi Lee received her B.A.Sc. and M.A.Sc. in Chemical Engineering from the University of Toronto. She has conducted environmental research at various government organizations and the University of Toronto. Her research activities have included establishing the physical-chemical properties of organochlorines and understanding the sources, trends, and behavior of persistent organic pollutants in the atmosphere of the Canadian Arctic. Ms. Lee also possesses experience in technology commercialization. She was involved in the successful commercialization of a proprietary technology that transformed recycled material into environmentally sound products for the building material industry. She went on to pursue her MBA degree, which she earned from York University’s Schulich School of Business. She continues her career, combining her engineering and business experiences with her interest in the environmental field. © 2006 by Taylor & Francis Group, LLC Contents Volume I Chapter 1 Introduction . . . . 1 Chapter 2 Aliphatic and Cyclic Hydrocarbons . . 61 Chapter 3 Mononuclear Aromatic Hydrocarbons . . . . . . . . . . . . . . . . 405 Chapter 4 Polynuclear Aromatic Hydrocarbons (PAHs) and Related Aromatic Hydrocarbons . . . . . . . . . . . . . . 617 Volume II Chapter 5 Halogenated Aliphatic Hydrocarbons . . . . . . . . . . . . . . . . 921 Chapter 6 Chlorobenzenes and Other Halogenated Mononuclear Aromatics . . . . . . . . . . 1257 Chapter 7 Polychlorinated Biphenyls (PCBs) . 1479 Chapter 8 Chlorinated Dibenzo-p-dioxins . . . 2063 Chapter 9 Chlorinated Dibenzofurans . . . . . . . 2167 Volume III Chapter 10 Ethers . . . . . . 2259 Chapter 11 Alcohols . . . . 2473 Chapter 12 Aldehydes and Ketones . . . . . . . . . 2583 Chapter 13 Carboxylic Acids . . . . . . . . . . . . . . 2687 Chapter 14 Phenolic Compounds . . . . . . . . . . . 2779 Chapter 15 Esters . . . . . . 3023 Volume IV Chapter 16 Nitrogen and Sulfur Compounds . . 3195 Chapter 17 Herbicides . . . 3457 Chapter 18 Insecticides . . 3711 Chapter 19 Fungicides . . . 4023 Appendix 1 . . . . . . . . . . . . . . 4133 Appendix 2 . . . . . . . . . . . . . . 4137 Appendix 3 . . . . . . . . . . . . . . 4161 © 2006 by Taylor & Francis Group, LLC 16 Nitrogen and Sulfur Compounds CONTENTS 16.1 List of Chemicals and Data Compilations . . 3197 16.1.1 Nitriles (Organic cyanides) . . . . . . 3197 16.1.1.1 Acetonitrile . . . . . . . . . 3197 16.1.1.2 Propionitrile . . . . . . . . . 3203 16.1.1.3 Butyronitrile . . . . . . . . 3207 16.1.1.4 Acrylonitrile (2-Propenenitrile) . . . . . . . . . . 3210 16.1.1.5 Benzonitrile . . . . . . . . . 3214 16.1.2 Aliphatic amines . . . . . . . . . . . . . . 3218 16.1.2.1 Dimethylamine . . . . . . 3218 16.1.2.2 Trimethylamine . . . . . . 3222 16.1.2.3 Ethylamine . . . . . . . . . 3225 16.1.2.4 Diethylamine . . . . . . . . 3228 16.1.2.5 n-Propylamine . . . . . . . 3231 16.1.2.6 n-Butylamine . . . . . . . . 3234 16.1.2.7 Ethanolamine . . . . . . . . 3236 16.1.2.8 Diethanolamine . . . . . . 3239 16.1.2.9 Triethanolamine . . . . . . 3241 16.1.3 Aromatic amines . . . . . . . . . . . . . . 3243 16.1.3.1 Aniline . . . . . . . . . . . . . 3243 16.1.3.2 2-Chloroaniline . . . . . . 3249 16.1.3.3 3-Chloroaniline . . . . . . 3253 16.1.3.4 4-Chloroaniline . . . . . . 3257 16.1.3.5 3,4-Dichloroaniline . . . 3261 16.1.3.6 o-Toluidine (2-Methylbenzeneamine) . . . . . . 3263 16.1.3.7 m-Toluidine (3-Methylbenzeneamine) . . . . . 3267 16.1.3.8 p-Toluidine (4-Methylbenzeneamine) . . . . . . 3270 16.1.3.9 N,N.-Dimethylaniline . 3274 16.1.3.10 2,6-Xylidine (2,6-Dimethylbenzeneamine) . 3277 16.1.3.11 Diphenylamine . . . . . . 3279 16.1.3.12 Benzidine . . . . . . . . . . . 3283 16.1.3.13 3,3.-Dichlorobenzidine 3285 16.1.3.14 N,N.-Bianiline . . . . . . . 3287 16.1.3.15 .-Naphthylamine (1-Aminonaphthalene) . . . 3289 16.1.3.16 .-Naphthylamine (2-Aminonaphthalene) . . . 3291 16.1.3.17 2-Nitroaniline . . . . . . . 3293 16.1.3.18 4-Nitroaniline . . . . . . . 3295 16.1.4 Nitroaromatic compounds . . . . . . . 3297 16.1.4.1 Nitrobenzene . . . . . . . . 3297 16.1.4.2 2-Nitrotoluene . . . . . . . 3304 16.1.4.3 4-Nitrotoluene . . . . . . . 3308 16.1.4.4 2,4-Dinitrotoluene (DNT) . . . . . . . . . . . . . . . 3313 © 2006 by Taylor & Francis Group, LLC 3196 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals 16.1.4.5 2,6-Dinitrotoluene . . . . 3317 16.1.4.6 2,4,6-Trinitrotoluene (TNT) . . . . . . . . . . . . . 3320 16.1.4.7 1-Nitronaphthalene (.-Nitronaphthalene) . . 3326 16.1.5 Amides and ureas . . . . . . . . . . . . . 3328 16.1.5.1 Acetamide . . . . . . . . . . 3328 16.1.5.2 Acrylamide . . . . . . . . . 3330 16.1.5.3 Benzamide . . . . . . . . . . 3331 16.1.5.4 Urea . . . . . . . . . . . . . . . 3333 16.1.6 Nitrosamines 3336 16.1.6.1 N-Nitrosodimethylamine . . . . . . . . . . . . . . . . 3336 16.1.6.2 N-Nitrosodipropylamine . . . . . . . . . . . . . . . . 3338 16.1.6.3 Diphenylnitrosoamine . 3340 16.1.7 Heterocyclic compounds . . . . . . . . 3342 16.1.7.1 Pyrrole . . . . . . . . . . . . . 3342 16.1.7.2 Indole . . . . . . . . . . . . . . 3346 16.1.7.3 Pyridine . . . . . . . . . . . . 3348 16.1.7.4 2-Methylpyridine . . . . . 3354 16.1.7.5 3-Methylpyridine . . . . . 3358 16.1.7.6 2,3-Dimethylpyridine . 3362 16.1.7.7 Quinoline . . . . . . . . . . . 3365 16.1.7.8 Isoquinoline . . . . . . . . . 3369 16.1.7.9 Benzo[f]quinoline . . . . 3372 16.1.7.10 Carbazole . . . . . . . . . . . 3375 16.1.7.11 Benzo[c,g]carbazole . . 3378 16.1.7.12 Acridine . . . . . . . . . . . . 3380 16.1.8 Sulfur compounds . . . . . . . . . . . . . 3383 16.1.8.1 Carbon disulfide . . . . . 3383 16.1.8.2 Dimethyl sulfide . . . . . 3386 16.1.8.3 Dimethyl disulfide . . . . 3391 16.1.8.4 Dimethyl sulfoxide (DMSO) . . . . . . . . . . . . 3394 16.1.8.5 Dimethyl sulfate . . . . . 3397 16.1.8.6 Methanethiol . . . . . . . . 3399 16.1.8.7 Ethanethiol . . . . . . . . . 3402 16.1.8.8 1-Propanethiol . . . . . . . 3406 16.1.8.9 1-Butanethiol (Butyl mercaptan) . . . . . . . . . 3409 16.1.8.10 Benzenethiol . . . . . . . . 3412 16.1.8.11 Thiophene . . . . . . . . . . 3415 16.1.8.12 Benzo[b]thiophene . . . 3419 16.1.8.13 Dibenzothiophene . . . . 3421 16.1.8.14 Thiourea . . . . . . . . . . . 3423 16.1.8.15 Thioacetamide . . . . . . . 3425 16.2 Summary Tables . . . . 3427 16.3 References . . . . . . . . . 3438 © 2006 by Taylor & Francis Group, LLC Nitrogen and Sulfur Compounds 3197 16.1 LIST OF CHEMICALS AND DATA COMPILATIONS 16.1.1 NITRILES (ORGANIC CYANIDES) 16.1.1.1 Acetonitrile Common Name: Acetonitrile Synonym: cyanomethane, ethanenitrile, methyl cyanide Chemical Name: acetonitrile CAS Registry No: 75-05-8 Molecular Formula: C2H3N, CH3CN Molecular Weight: 41.052 Melting Point (°C): –43.82 (Lide 2003) Boiling Point (°C): 81.65 (Lide 2003) Density (g/cm3 at 20°C): 0.7857 (Dreisbach 1961; Weast 1982–83; Dean 1985) 0.7803 (25°C, Dreisbach 1961) Molar Volume (cm3/mol): 52.7 (calculated-density, Rohrschneider 1973) 57.4 (exptl. at normal bp, Lee et al. 1972) 56.3 (calculated-Le Bas method at normal boiling point) Dissociation Constant, pK: 29.1 (pKa, Riddick et al. 1986; Howard 1993) 32.2 (pKs, Riddick et al. 1986) –10.12 (pKBH + , Riddick et al. 1986) Enthalpy of Vaporization, .HV (kJ/mol): 35.01, 31.51 (25°C, bp, Dreisbach 1961) 32.94, 29.82 (25°C, bp, Riddick et al. 1986) Enthalpy of Fusion, .Hfus (kJ/mol): 8.167 (Riddick et al. 1986) Entropy of Fusion, .Sfus (J/mol K): Fugacity Ratio at 25°C (assuming .Sfus = 56 J/mol K), F: 1.0 Water Solubility (g/m3 or mg/L at 25°C): > 3.1 . 106 (Booth & Everson 1948) miscible (Dean 1985; Riddick et al. 1986; Yaws et al. 1990; Howard 1993) Vapor Pressure (Pa at 25°C or as indicated and reported temperature dependence equations. Additional data at other temperatures designated * are compiled at the end of this section): 11870* (interpolated-regression of tabulated data, temp range –47–81.8°C, Stull 1947) log (P/mmHg) = 7.12257 – 1315.2/(230 + t/°C), (Antoine eq., Dreisbach & Martin 1949) 11240 (calculated by formula, Dreisbach 1961) log (P/mmHg) = 7.07354 – 1279.2/(224.0 + t/°C), temp range 5–119°C, (Antoine eq. for liquid state, Dreisbach 1961) 12156* (25.56°C, measured range 7.3–27.38°C, Putnam et al. 1965) log (P/mmHg) = 7.89511 – 1773.06/(T/K); temp range 280–300.5 K (Antoine eq., Putnam et al. 1965) 11510 (Hoy 1970) 24459* (41.82°C, ebulliometry, measured range 41–82°C, Meyer et al. 1971) log (P/mmHg) = 6.23655 – 1397.9228/(239.275 + t/°C); temp range 41–82°C (ebulliometry, Meyer et al. 1971) log (P/mmHg) = [–0.2185 . 8173.2/(T/K)] + 7.938662; temp range: –47.0 to 81.8°C, (Antoine eq., Weast 1972–73) 11919* (25.3°C, measured range 15.1–89.2°C, Dojcanske & Heinrich 1974) N © 2006 by Taylor & Francis Group, LLC 3198 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals 8306* (saturated-vapor volume, extrapolated from fitted Antoine eq., Mousa 1981) log (P/kPa) = 6.4914 – 1420.8649/(T/K – 42.15); temp range 438.9–530.1 K (ebulliometry, Mousa 1981) 9864, 15330 (20°C, 30°C, Verschueren 1983) 11790, 11830 (interpolated values-Antoine equations, Boublik et al. 1984) log (P/kPa) = 6.39532 – 1420.682/(241.852 + t/°C), temp range: 15.1–89.2°C (Antoine eq. from reported exptl. data, Boublik et al. 1984) log (P/kPa) = 7.54606 – 2093.145/(298.369 + t/°C), temp range: 7.26–27.4°C (Antoine eq. from reported exptl. data, Boublik et al. 1984) 12310 (calculated-Antoine eq., Dean 1985, 1992) log (P/mmHg) = 7.11988 – 1314.4/(230 + t/°C), temp range: liquid (Antoine eq., Dean 1985, 1992) 11840 (Riddick et al. 1986; Howard et al. 1986; quoted, Banerjee et al. 1990; Howard 1993) log (P/kPa) = 6.24747 – 1315.2/(230.0 + t/°C), temp range not specified (Antoine eq., Riddick et al. 1986) 11800 (extrapolated-Antoine eq., Stephenson & Malanowski 1987) log (PL/kPa) = 6.34522 – 1388.446/(–34.856 + T/K), temp range: 314–355 K, (Antoine eq., Stephenson & Malanowski 1987) 11840 (selected, Riddick et al. 1986) log (P/kPa) = 6.24724 – 1315.2/(230 + t/°C), temp range not specified (Antoine eq., Riddick et al. 1986) log (P/mmHg) = 23.1953 – 2.3389 . 103/(T/K) –5.4954·log (T/K) + 7.9894 . 10–10 · (T/K) + 2.3293 . 10–6 · (T/K)2; temp range 229–546 K (vapor pressure eq., Yaws 1994) 10604* (22.634°C, comparative ebulliometry, measured range 278–373 K, Ewing & Sanchez Ochoa 2004) ln (P/kPa) = 14.7340 – 3268.53/(T/K – 31.615), for temp range 290–362 K (comparative ebulliometry, Ewing & Sanchez Ochoa 2004) Henry’s Law Constant (Pa·m3/mol at 25°C or as indicated and reported temperature dependence equations. Additional data at other temperatures designated* are compiled at the end of this section): 3.50, 2.78 (exptl., calculated-bond contribution, Hine & Mookerjee 1975) 2.07* (headspace-GC, measured range 0–25°C, Snider & Dawson 1985) 2.033 (computed-vapor-liquid equilibrium VLE data, Yaws et al. 1991) 1.474* (20°C, headspace-GC, measured range 6.0–30°C, Benkelberg et al. 1995) 1.474, 1.477, 1.685 (20°C, headspace-GC, deionized water, rain water, artificial seawater, Benkelberg et al. 1995) ln (kH/atm) = (13.8 ± 0.3) – (4106 ± 101)/T/K), temp range: 6–30°C (headspace-GC measurement, Benkelberg et al. 1995) 1.55 (20°C, selected from literature experimentally measured data, Staudinger & Roberts 2001) log KAW = 2.353 – 1627/(T/K) (van’t Hoff eq. derived from literature data, Staudinger & Roberts 2001) 2.05 (Ostwald concentration coefficient-concn ratio-GC/FID, Bebahani et al. 2002) Octanol/Water Partition Coefficient, log KOW: –0.34 (shake flask-GC, Hansch & Anderson 1967; Leo et al. 1969, 1971; Hansch & Leo 1985) –0.54 (shake flask-GC, Tanii & Hashimoto 1984) –0.34 (recommended, Sangster 1989, 1993) –0.34 (recommended, Hansch et al. 1995) Octanol/Air Partition Coefficient, log KOA: 2.31 (head-space GC, Abraham et al. 2001) Bioconcentration Factor, log BCF: –0.523 (estimated-KOW as per regression eq of Bysshe 1982, Howard 1993) Sorption Partition Coefficient, log KOC: –0.523 (soil, estimated-KOW, Lyman et al. 1982; quoted, Howard 1993) –0.714 (calculated-KOW, Kollig 1993) Environmental Fate Rate Constants, k, or Half-Lives, t.: Volatilization: t. ~ 21 h from a model river of 1-m deep flowing at 1 m/s with a wind velocity of 3 m/s based on Henry’s law constant (Lyman et al. 1982; quoted, Howard 1993) © 2006 by Taylor & Francis Group, LLC Nitrogen and Sulfur Compounds 3199 Photolysis: Oxidation: rate constant k, for gas-phase second order rate constants, kOH for reaction with OH radical, kNO3 with NO3 radical and kO3 with O3 or as indicated, *data at other temperatures and/or the Arrhenius expression see reference: photooxidation t. = 314 – 12559 yr in water, based on measured rate data for reaction with hydroxyl radical in aqueous solution (Dorfman & Adams 1973; Howard et al. 1991) kOH* = (4.94 ± 0.6) . 10–14 cm3 molecule–1 s–1 at 297.2 K, measured range 297–424 K (flash photolysisresonance fluorescence, Harris et al. 1981; quoted, Howard 1993) kOH* = (1.94 ± 0.37) . 10–14 cm3 molecule–1 s–1 at 298 K, measured range 250–363 K (flash photolysisresonance fluorescence, Kurylo & Knable 1984) kOH* = (2.1 ± 0.3) . 10–14 cm3 molecule–1 s–1 at 295 K, measured range 295–393 K (discharge flow-EPR, Poulet et al. 1984) kOH(exptl) = 2.1 . 10–14 cm3 molecule–1 s–1, kOH(calc) = 2.0 . 10–14 cm3 molecule–1 s–1 at 298 K (Atkinson 1985) kOH = 3 . 10–14 cm3 molecule–1 s–1 (Atkinson 1985; quoted, Howard et al. 1991; Howard 1993) kOH = 1.90 . 10–14 cm3 molecule–1 s–1 and k(soln) = 3.70 . 10–14 cm3 molecule–1 s–1 for the solution-phase reaction with hydroxyl radical in aqueous solution (Wallington et al. 1988) kOH* = 2.14 . 10–14 cm3 molecule–1 s–1 at 298 K (recommended, Atkinson 1989) Hydrolysis: k = 5.8 . 10–3 M–1 h–1 at pH 7 and 25°C with t. > 150000 yr (Ellington et al. 1987) kO3(aq.) . 6 . 10–5 M–1 s–1 for direct reaction with ozone in water at pH 2 and 22°C, with t. . 18 yr at pH 7 (Yao & Haag 1991). Biodegradation: t.(aq. aerobic) = 168 – 672 h, based on aerobic river die-away test data (Ludzack et al. 1958; quoted, Howard et al. 1991); t.(aq. anaerobic) = 672 – 2688 h, based on estimated aqueous aerobic biodegradation half-life (Howard et al. 1991). Biotransformation: Bioconcentration, Uptake (k1) and Elimination (k2) Rate Constants: Half-Lives in the Environment: Air: photooxidation t. = 1299 – 12991 h, based on measured rate constant k = 3 . 10–14 cm3 molecule–1 s–1 for the vapor phase reaction with hydroxyl radical in air (Atkinson 1985; quoted, Howard et al. 1991; Howard 1993); atmospheric transformation lifetime was estimated to be > 5 d (Kelly et al. 1994). Surface water: t. = 168 – 672 h, based on aerobic river die-away test data (Howard et al. 1991); photooxidation t. = 314 – 12559 yr, based on measured rate data for reaction with hydroxyl radical in aqueous solution (Dorfman & Adams 1973; Howard et al. 1991); t. . 18 yr for direct reaction with ozone in water at pH 7 and 22°C (Yao & Haag 1991). Groundwater: t. = 336 – 8640 h, based on estimated aqueous aerobic biodegradation half-life (Howard et al. 1991). Sediment: Soil: t. = 168 – 672 h, based on estimated aqueous aerobic biodegradation half-life (Howard et al. 1991). Biota: TABLE 16.1.1.1.1 Reported vapor pressures of acetonitrile at various temperatures and the coefficients for the vapor pressure equations log P = A – B/(T/K) (1) ln P = A – B/(T/K) (1a) log P = A – B/(C + t/°C) (2) ln P = A – B/(C + t/°C) (2a) log P = A – B/(C + T/K) (3) log P = A – B/(T/K) – C·log (T/K) (4) (Continued) © 2006 by Taylor & Francis Group, LLC 3200 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals TABLE 16.1.1.1.1 (Continued) 1. Stull 1947 Putnam et al. 1965 Meyer et al. 1971 Dojcanske & Heinrich 1974 summary of literature data manometer ebulliometry in Boublik et al. 1984 t/°C P/Pa t/°C P/Pa t/°C P/Pa t/°C P/Pa –47.0 133.3 7.259 4997 41.82 24459 15.1 7359 –26.6 666.6 10.47 5861 46.09 29026 20.1 9413 –16.3 1333 13.791 6914 46.11 29032 25.3 11919 –5.0 2666 18.701 8809 50.36 34288 30.7 15252 7.7 5333 21.905 10244 55.37 41393 35 18292 15.9 7999 23.401 11031 60.64 50155 39.95 22465 27 13332 25.563 12156 65.91 60390 40 22625 43.7 26664 27.38 13187 70.74 71145 44.9 27638 62.5 53329 76.31 85512 50.1 33797 81.8 101325 eq. 1 P/mmHg 81.87 101990 54.9 40517 A 7.89511 81.89 102010 60 49022 mp/°C –41.0 B 1773.06 64.4 57182 bp/°C 81.66 64.95 58102 eq. 2 P/mmHg 70 68967 A 6.23655 73.05 76713 B 1397.923 75.1 81380 C 239.275 77.2 87952 81.1 99431 85.2 112364 88.2 123189 89.2 124776 2. Mousa 1981 Ewing & Sanchez Ochoa 2004 ebulliometry-pressure gauge comparative ebulliometry T/K P/kPa t/°C P/Pa t/°C P/kPa set A set B 438.9 784.4 4.772 4323# 81.4 100.745 440.9 842.8 5.475 4490# 87.792 122.631 442.6 862.3 8.417 5247# 98.589 168.122 444.5 876.9 12.226 6385# 105.665 204.592 447.9 960.3 14.517 7165# 110.961 235.792 450.5 999.2 17.497 8296 121.144 306.279 455.7 1116.5 19.596 9182 132.086 399.5 460.2 1234.6 22.634 10604 142.063 502.665 505.3 2604.9 27.674 13366 150.533 605.601 508.1 1704.6 30.661 15271 157.974 708.993 512.1 1924.0 36.486 19639 164.152 804.861 519.7 3243.3 42.283 24972 170.346 910.819 521.6 3303.1 47.968 31311 176.446 1025.47 524.8 3482.8 51.872 36387 182.586 1151.97 530.1 3722.1 58.125 45907 188.724 1290.2 63.263 55169 195.22 1450.28 bp/K 354.8 68.029 65092 200.902 1602.63 72.425 75440 206.004 1749.88 © 2006 by Taylor & Francis Group, LLC Nitrogen and Sulfur Compounds 3201 TABLE 16.1.1.1.1 (Continued) Mousa 1981 Ewing & Sanchez Ochoa 2004 ebulliometry-pressure gauge comparative ebulliometry T/K P/kPa t/°C P/Pa t/°C P/kPa eq.3 P/kPa 76.178 85311 211.619 2110.77 A 6.4914 79.929 95589 217.22 2303.51 B 1420.8649 81.515 101120 222.602 2523.66 C –42.15 84.406 110614 228.33 2747.95 88.462 125129 233.771 2999.22 95.816 155329 339.66 3254.08 100.02 175036 244.858 3512.89 254.64 3760.37 for temp range 290–373 K 258.929 4001.46 eq. 2a P/mmHg 261.882 4174.61 A 14.734 B 3268.53 data fitted to Wagner eq. C –31.615 for temp range 354.5–535 K # data not used in regression FIGURE 16.1.1.1.1 Logarithm of vapor pressure versus reciprocal temperature for acetonitrile. Acetonitrile: vapor pressure vs. 1/T 0.0 1.0 2.0 3.0 4.0 5.0 6.0 7.0 8.0 0.0018 0.0022 0.0026 0.003 0.0034 0.0038 0.0042 0.0046 1/(T/K) P( gol S ) aP/ experimental data Stull 1947 b.p. = 81.65 °C m.p. = -43.82 °C © 2006 by Taylor & Francis Group, LLC 3202 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals TABLE 16.1.1.1.2 Reported Henry’s law constants of acetonitrile at various temperatures and temperature dependence equations ln KAW = A – B/(T/K) (1) log KAW = A – B/(T/K) (1a) ln (1/KAW) = A – B/(T/K) (2) log (1/KAW) = A – B/(T/K) (2a) ln (kH/atm) = A – B/(T/K) (3) ln [H/(Pa m3/mol)] = A – B/(T/K) (4) ln [H/(atm·m3/mol)] = A – B/(T/K) (4a) KAW = A – B·(T/K) + C·(T/K)2 (5) Snider & Dawson 1985 Benkelberg et al. 1995 gas stripping-GC equil. vapor phase concn-GC t/°C H/(Pa m3/mol) t/°C H/(Pa m3/mol) deionized water 0 0.614 6 0.72 25 2.066 10 1.0706 20 1.474 enthalpy of transfer: 30 2.356 .H/(kJ mol–1) = 30.54 rain water 20 1.477 artificial 20 1.685 eq. 3 H/atm A 13.8 ± 0.3 B 4106 ± 101 FIGURE 16.1.1.1.2 Logarithm of Henry’s law constant versus reciprocal temperature for acetonitrile. Acetonitrile: Henry's law constant vs. 1/T -2.0 -1.0 0.0 1.0 2.0 0.003 0.0031 0.0032 0.0033 0.0034 0.0035 0.0036 0.0037 0.0038 1/(T/K) m. aP( / H nl 3 ) l om / Snider & Dawson 1985 Benkelberg et al. 1995 (in deionized water) Benkelberg et al. 1995 (in rain water) Hine & Mookerjee 1975 © 2006 by Taylor & Francis Group, LLC Nitrogen and Sulfur Compounds 3203 16.1.1.2 Propionitrile Common Name: Propionitrile Synonym: propanenitrile, ethyl cyanide, cyanoethane, propyl nitrile Chemical Name: propionitrile CAS Registry No: 107-12-0 Molecular Formula: C3H5N, CH3CH2CN Molecular Weight: 55.079 Melting Point (°C): –92.78 (Lide 2003) Boiling Point (°C): 97.14 (Lide 2003) Density (g/cm3 at 20°C): 0.7818 (Weast 1982–83; Dean 1985) 0.78182, 0.77682 (20°C, 25°C, Riddick et al. 1986) Molar Volume (cm3/mol): 70.4 (calculated-density, Taft et al. 1985; Leahy 1986; Kamlet et al. 1986, 1987) 78.5 (calculated-Le Bas method at normal boiling point) Dissociation Constant: 33.54 (pKs, Riddick et al. 1986) Enthalpy of Vaporization, .Hvap, (kJ/mol): 37.41, 32.77 (25°C, bp, Dreisbach 1961) 36.03, 30.96 (25°C, bp, Riddick et al. 1986) Enthalpy of Fusion, .Hfus (kJ/mol): 5.045 (Riddick et al. 1986) Entropy of Fusion, .Sfus (J/mol K): Fugacity Ratio at 25°C (assuming .Sfus = 56 J/mol K), F: 1.0 Water Solubility (g/m3 or mg/L at 25°C or as indicated. Additional data at other temperatures designated * are compiled at the end of this section): 104950 (Seidell 1941) 105200 (Hansch et al. 1968) 103000 (Dean 1985; Riddick et al. 1986; Howard 1990) 55000, 65000 (20°C, 30°C, shake flask-GC, measured range 0–90°C, Stephenson 1994) Vapor Pressure (Pa at 25°C or as indicated and reported temperature dependence equations. Additional data at other temperatures designated * are compiled at the end of this section): 6005* (interpolated-regression of tabulated data, temp range –35–97.1°C, Stull 1947) 10114* (35.5°C, ebulliometry, measured range 35.5–97.35°C, Dreisbach & Shrader 1949) log (P/mmHg) = 7.15217 – 1398.2/(230 + t/°C); temp range 35.5–97.35°C, (Antoine eq., Dreisbach & Martin 1949) 5333* (22.05°C, measured range –84.66–22.05°C, Milazzo 1956) 5950 (calculated by formula, Dreisbach 1961) log (P/mmHg) = 7.05846 – 1327.9/(221.0 + t/°C), temp range: 17–137°C, (Antoine eq. for liquid state, Dreisbach 1961) log (P/mmHg) = [–0.2185 . 8769.0/(T/K)] + 8.079473; temp range: –35 to 97.1°C, (Antoine eq., Weast 1972–73) 6140 (22.05°C, quoted exptl., Boublik et al. 1973, 1984) 6163, 6143 (extrapolated values-Antoine eq., Boublik et al. 1984) log (P/kPa) = 5.89149 – 1181.562/(206.603 + t/°C), temp range: 35.5–97.39°C (Antoine eq. from reported exptl. data, Boublik et al. 1984) log (P/kPa) = 4.43918 – 677.415/(160.551 + t/°C), temp range: –84.7 to 22.05°C (Antoine eq. from reported exptl. data, Boublik et al. 1984) N © 2006 by Taylor & Francis Group, LLC 3204 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals 6140 (extrapolated-Antoine eq., Dean 1985, 1992) log (P/mmHg) = 5.2782 – 665.52/(159.0 + t/°C), temp range: –84 to 22°C (Antoine eq., Dean 1985, 1992) 5950 (selected, Riddick et al. 1986) log (P/kPa) = 6.27702 – 1398.2/(230 + t/°C), temp range not specified (Antoine eq., Riddick et al. 1986) log (P/kPa) = 7.15190 – 1894.10/(T/K); temp range: 9–25°C, (Antoine eq., Riddick et al. 1986) 6306 (calculated-Antoine eq., Stephenson & Malanowski 1987) log (PL/kPa) = 7.395 – 3213/(T/K), temp range: 357–413 K, (Antoine eq.-I, Stephenson & Malanowski 1987) log (PL/kPa) = 10.31055 – 3994.667/(T/K), temp range: 373–413 K, (Antoine eq.-II, Stephenson & Malanowski 1987) log (P/mmHg) = 33.7908 – 2.9113 . 103/(T/K) – 9.1506·log (T/K) + 1.1173 . 10–11·(T/K) + 3.2756 . 10–6·(T/K)2; temp range 180–564 K (vapor pressure eq., Yaws 1994) Henry’s Law Constant (Pa·m3/mol at 25°C): 3.800 (partial pressure, Butler & Ramchandani 1935) 3.748 (partial vapor pressure-GC, Buttery et al. 1969) 3.752, 3.752, 4.114 (exptl., calculated-group contribution, calculated-bond contribution, Hine & Mookerjee 1975) 5.947 (Howard 1990) Octanol/Water Partition Coefficient, log KOW: 0.041 (shake flask, Collander 1951) 0.16 (shake flask-GC, Hansch & Anderson 1967; Hansch et al. 1968) – 0.10 (shake flask-GC, Tanii & Hashimoto 1984) 0.16 (recommended, Sangster 1989, 1993) 0.16 (recommended, Hansch et al. 1995) Octanol/Air Partition Coefficient, log KOA: 2.69 (head-space GC, Abraham et al. 2001) Bioconcentration Factor, log BCF: – 0.108 (estimated-KOW, Lyman et al. 1982; quoted, Howard 1990) Sorption Partition Coefficient, log KOC: 0.079 (soil, estimated-KOW, Lyman et al. 1982; quoted, Howard 1990) Environmental Fate Rate Constants, k, or Half-Lives, t.: Volatilization: using Henry’s law constant, t. = 13.3 h was estimated for a model river 1 m deep flowing 1 m/s with wind speed 3 m/s (Lyman et al. 1982; quoted, Howard 1990). Photolysis: Oxidation: rate constant k, for gas-phase second order rate constants, kOH for reaction with OH radical, kNO3 with NO3 radical and kO3 with O3 or as indicated, *data at other temperatures and/or the Arrhenius expression see reference: kOH* = (1.94 ± 0.20) . 10–13 cm3 molecule–1 s–1 at 298.2 K, measured range 298–423 K (flash photolysisresonance fluorescence, Harris et al. 1981) kOH = 1.9 . 10–13 cm3 molecule–1 s–1 at 298 K (Atkinson 1985) kOH = 1.94 . 10–13 cm3 molecule–1 s–1 at 298.2 K, k(soln) = 1.60 . 10–13 cm3 molecule–1 s–1 for the solutionphase reaction with hydroxyl radical in aqueous solution (Wallington et al. 1988) photooxidation t. = 83 d in air, based on experimental rate constant assuming t. = 12 h of sunlight for the vapor-phase reaction with hydroxyl radical in air and t. > 100 d for the reaction with ozone in the atmosphere (Howard 1990) kOH = 0.194 . 10–12 cm3 molecule–1 s–1 at 298.2 K (review, Atkinson 1989) Hydrolysis: Biodegradation: Biotransformation: Bioconcentration, Uptake (k1) and Elimination (k2) Rate Constants: © 2006 by Taylor & Francis Group, LLC Nitrogen and Sulfur Compounds 3205 Half-Lives in the Environment: Air: t. = 83 d, based on experimental rate constant assuming 12 h of sunlight for the vapor-phase reaction with hydroxyl radical in air and t. > 100 d for the reaction with ozone in the atmosphere (Harris et al. 1981; quoted, Howard 1990). TABLE 16.1.1.2.1 Reported aqueous solubilities and vapor pressures of propionitrile at various temperatures log P = A – B/(T/K) (1) ln P = A – B/(T/K) (1a) log P = A – B/(C + t/°C) (2) ln P = A – B/(C + t/°C) (2a) log P = A – B/(C + T/K) (3) log P = A – B/(T/K) – C·log (T/K) (4) Aqueous solubility Vapor pressure Stephenson 1994 Stull 1947 Dreisbach & Shrader 1949 Milazzo 1956 shake flask-GC summary of literature data ebulliometry t/°C S/g·m–3 t/°C P/Pa t/°C P/Pa t/°C P/Pa 0 62000 –35.0 133.3 35.5 10114 –84.66 1 20 55000 –13.8 666.6 43.76 16500 –77.01 2 30 65000 –3.0 1333 70.45 42066 –67.42 6 40 79000 8.8 2666 84.44 67661 –65.49 7 50 94000 22 5333 97.35 101325 –59.72 13 60 98000 30.1 7999 –52.96 17 70 134000 41.4 13332 –46.19 49 80 156000 58.2 26664 –34.95 133 90 195000 77.7 53329 –22.85 356 97.1 101325 –13.08 707 –2.95 1347 mp/°C –91.9 6.36 2400 16.42 4146 22.05 5333 FIGURE 16.1.1.2.1 Logarithm of mole fraction solubility (ln x) versus reciprocal temperature for propionitrile. Propionitrile: solubility vs. 1/T -4.5 -4.0 -3.5 -3.0 -2.5 0.0026 0.0028 0.003 0.0032 0.0034 0.0036 0.0038 1/(T/K) x nl Stephenson 1994 © 2006 by Taylor & Francis Group, LLC 3206 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals FIGURE 16.1.1.2.2 Logarithm of vapor pressure versus reciprocal temperature for propionitrile. Propionitrile: vapor pressure vs. 1/T -2.0 -1.0 0.0 1.0 2.0 3.0 4.0 5.0 6.0 0.0026 0.003 0.0034 0.0038 0.0042 0.0046 0.005 0.0054 0.0058 1/(T/K) P( gol S ) aP/ Dreisbach & Shrader 1949 Milazzo 1956 Stull 1947 b.p. = 97.14 °C m.p. = -92.78 °C © 2006 by Taylor & Francis Group, LLC Nitrogen and Sulfur Compounds 3207 16.1.1.3 Butyronitrile Common Name: n-Butyronitrile Synonym: butanenitrile Chemical Name: butyronitrile CAS Registry No: 109-74-0 Molecular Formula: C4H7N, CH3CH2CH2CN Molecular Weight: 69.106 Melting Point (°C): –111.9 (Lide 2003) Boiling Point (°C): 117.6 (Lide 2003) Density (g/cm3): 0.7911, 0.7865 (20°C, 25°C, Riddick et al. 1986) Dissociation Constant, pKa: Molar Volume (cm3/mol): 88.4 (30°C, Stephenson & Malanowski 1987) 100.7 (calculated-Le Bas method at normal boiling point) Enthalpy of Vaporization, .HV (kJ/mol): 39.33, 34.43 (25°C, bp, Riddick et al. 1986) Enthalpy of Sublimation, .Hsubl (kJ/mol): Enthalpy of Fusion, .Hfus (kJ/mol): 5.021 (Riddick et al. 1986) Entropy of Fusion, .Sfus (J/mol K): Fugacity Ratio at 25°C (assuming .Sfus = 56 J/mol K), F: 1.0 Water Solubility (g/m3 or mg/L at 25°C or as indicated. Other data at other temperatures designated * are compiled at the end of this section): 33000 (selected, Riddick et al. 1986) 33500* (20°C, shake flask-GC/TC, measured range 0–90°C, Stephenson 1994) Vapor Pressure (Pa at 25°C or as indicated and the reported temperature dependence equations. Additional data at other temperatures designated * are compiled at the end of this section): 1333* (25.7°C, summary of literature data, temp range –20 to 117.5°C, Stull 1947) 3592* (30.64°C, ebulliometry, measured range 30.64–120.223°C, Meyer et al. 1971) log (P/mmHg) = 6.771124 – 1444.5851/(t/°C + 223.275); temp range 30.64–120.223°C (Antoine eq., ebulliometric measurements, Meyer et al. 1971) 13831* (59.807°C, ebulliometry, measured range 59.807–127.707°C, Meyer & Hotz 1976) 2546 (selected, Riddick et al. 1986) log (P/kPa) = 6.25390 – 1452.076/(t/°C + 224.1855); temp range not specified (Riddick et al. 1986) log (PL/kPa) = 6.25397 – 1452.076/(–46.9645 + T/K); temp range 332–401 K (Antoine eq., Stephenson & Malanowski 1987) log (P/mmHg) = 4.8780 – 2.5505 . 103/(T/K) + 3.6306·log (T/K) – 1.663 . 10–2·(T/K) + 1.0604 . 10–5·(T/K)2; temp range 161–582 K (vapor pressure eq., Yaws 1994) Henry’s Law Constant (Pa m3/mol at 25°C): Octanol/Water Partition Coefficient, log KOW: 0.53 (shake flask-GC, Tanii & Hashimoto 1984) 0.53 (recommended, Sangster 1993; Hansch et al. 1995) N © 2006 by Taylor & Francis Group, LLC 3208 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals Bioconcentration Factor, log BCF or log KB: Sorption Partition Coefficient, log KOC: TABLE 16.1.1.3.1 Reported aqueous solubilities and vapor pressures of butyronitrile at various temperatures log P = A – B/(T/K) (1) ln P = A – B/(T/K) (1a) log P = A – B/(C + t/°C) (2) ln P = A – B/(C + t/°C) (2a) log P = A – B/(C + T/K) (3) log P = A – B/(T/K) – C·log (T/K) (4) Aqueous solubility Vapor pressure Stephenson 1994 Stull 1947 Meyer et al. 1971 Meyer & Hotz 1976 shake flask-GC summary of literature data ebulliometry ebulliometry t/°C S/g·m–3 t/°C P/Pa t/°C P/Pa t/°C P/Pa 0 37500 –20.0 133.3 30.64 3592 59.807 13831 20 33500 2.10 666.6 39.03 5459 65.615 17513 30 33100 13.4 1333 49.913 9041 71.638 22151 40 32500 25.7 2666 59.226 13527 77.023 27111 50 32300 38.4 5333 67.536 18888 83.599 34366 60 32100 47.3 7999 77.313 27448 89.462 42109 70 31900 59.0 13332 86.71 39316 96.022 52382 80 34000 76.7 26664 93.675 48525 102.279 63984 90 36100 96.8 53329 100.638 60811 109.175 79081 117.5 101325 100.701 60928 115.651 95737 107.041 74214 121.838 114148 mp/°C 112.04 88451 127.707 134135 117.254 100344 120.223 109170 bp/°C 117.583 log P = A – B/(C + t/°C) P/mmHg A 6.771124 B 1444.5851 C 223.275 © 2006 by Taylor & Francis Group, LLC Nitrogen and Sulfur Compounds 3209 FIGURE 16.1.1.3.1 Logarithm of mole fraction solubility (ln x) versus reciprocal temperature for butyronitrile. FIGURE 16.1.1.3.2 Logarithm of vapor pressure versus reciprocal temperature for butyronitrile. Butyronitrile: solubility vs. 1/T -5.5 -5.0 -4.5 -4.0 -3.5 0.0026 0.0028 0.003 0.0032 0.0034 0.0036 0.0038 1/(T/K) x nl Stephenson 1994 Butyronitrile: vapor pressure vs. 1/T 0.0 1.0 2.0 3.0 4.0 5.0 6.0 7.0 8.0 0.0022 0.0026 0.003 0.0034 0.0038 0.0042 1/(T/K) P ( gol S ) aP/ Meyer et al. 1971 Meyer & Hotz 1976 Stull 1947 b.p. = 117.6 °C © 2006 by Taylor & Francis Group, LLC 3210 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals 16.1.1.4 Acrylonitrile (2-Propenenitrile) Common Name: Acrylonitrile Synonym: cyanoethylene, propenenitrile, 2-propenenitrile, vinyl cyanide Chemical Name: acrylonitrile, cyanoethylene CAS Registry No: 107-13-1 Molecular Formula: C3H3N, CH2=CHCN Molecular Weight: 53.063 Melting Point (°C): –83.48 (Lide 2003) Boiling Point (°C): 77.30 (Riddick et al. 1986; Howard 1989; Lide 2003) Density (g/cm3 at 20°C): 0.8060, 0.8004 (20°C, 25°C, Riddick et al. 1986) Molar Volume (cm3/mol): 65.8 (20°C, calculated-density) 71.1 (calculated-Le Bas method at normal boiling point) Dissociation Constant, pKa: Enthalpy of Fusion, .Hfus (kJ/mol): 6.230 (Riddick et al. 1986) Entropy of Fusion, .Sfus (J/mol K): Fugacity Ratio at 25°C (assuming .Sfus = 56 J/mol K), F: 1.0 Water Solubility (g/m3 or mg/L at 25°C or as indicated. Additional data at other temperatures designated * are compiled at the end of this section): 79000 (Klein et al. 1957) 75000 (Gunther et al. 1968) 73500 (20°C, Windholz 1976) 73240 (shake flask-LSC, Veith et al. 1980) 7.35 wt%* (20°C, Kirk-Othmer Encyclopedia 3rd ed., measured range 0–60°C, quoted, Basu et al. 1983) 73500 (20°C, Riddick et al. 1986) 69000*, 66400 (20°C, 30°C, shake flask-GC, measured range 0–70°C, Stephenson 1994) Vapor Pressure (Pa at 25°C or as indicated and reported temperature dependence equations. Additional data at other temperatures designated * are compiled at the end of this section): 14340* (interpolated-regression of tabulated data, temp range –51 to 78.5°C, Stull 1947) 11732* (20°C, temp range 20–77°C, Gudkov et al. 1964; quoted, Boublik et al. 1984) 14100 (Hoy 1970) log (P/mmHg) = [–0.2185 . 7941.4/(T/K)] + 7.851016; temp range: –51 to 78.5°C, (Antoine eq., Weast 1972–73) 14720 (extrapolated-Antoine eq., Boublik et al. 1984) log (P/kPa) = 4.77668 – 649.583/(155.006 + t/°C), temp range 20–70°C (Antoine eq. from reported exptl. data, Boublik et al. 1984) 14370 (Daubert & Danner 1985) 15240 (calculated-Antoine eq., Dean 1985, 1992) log (P/mmHg) = 7.03855 – 1232.53/(222.47 + t/°C), temp range –20 to 140°C (Antoine eq., Dean 1985, 1992) 11000 (20°C, Riddick et al. 1986) log (P/kPa) = 6.643 – 11644.7/(T/K), temp range not specified (Antoine eq., Riddick et al. 1986) 14560 (interpolated-Antoine eq.-II, Stephenson & Malanowski 1987) log (PL/kPa) = 6.12021 – 1288.9/(–38.74 + T/K); temp range 257–352 K (Antoine eq.-I, Stephenson & Malanowski 1987) log (PL/kPa) = 6.4811 – 1518.381/(–12.003 + T/K); temp range 283–343 K (Antoine eq.-II, Stephenson & Malanowski 1987) N © 2006 by Taylor & Francis Group, LLC Nitrogen and Sulfur Compounds 3211 15600 (calculated-solvatochromic parameters, Banerjee et al. 1990) log (P/mmHg) = 35.921 – 2.7763 . 103/(T/K) – 10.101·log (T/K) – 3.1547 . 10–10·(T/K) + 4.7299 . 10–6·(T/K)2; temp range 190–535 K (vapor pressure eq., Yaws 1994) Henry’s Law Constant (Pa·m3/mol at 25°C): 11.14 (Bocek 1976; quoted, Basu et al. 1983; Howard 1989) 8.918 (calculated-P/C, Mabey et al. 1982) 9.420 (quoted, WERL Treatability Database, Ryan et al. 1988) Octanol/Water Partition Coefficient, log KOW: 0.25 (shake flask-HPLC, Pratesi et al. 1979) 0.00 (shake flask, Fujisawa & Masuhara 1980, 1981) 0.09 (shake flask-GC, Tanii & Hashimoto 1984) 0.25 (Hansch & Leo 1985) 0.25 (recommended, Sangster 1989) 0.25 (recommended, Hansch et al. 1995) Octanol/Air Partition Coefficient, log KOA: Bioconcentration Factor, log BCF: 1.68 (bluegill sunfish, Barrows et al. 1978) 0.00 (estimated-S, Kenaga 1980) 1.68, 0.32 (bluegill sunfish, calculated-KOW, Veith et al. 1980) 0.017 (microorganisms-water, calculated-KOW, Mabey et al. 1982) Sorption Partition Coefficient, log KOC: 0.954 (soil, calculated-S, Kenaga 1980) –0.071 (sediment-water, calculated-KOW, Mabey et al. 1982) 1.101, 1.006; 1.09 (Captina silt loam, McLaurin sandy loam; weighted mean, batch equilibrium-sorption isotherm, Walton et al. 1992) –0.0899 (calculated-KOW, Walton et al. 1992) –0.0890 (calculated-KOW, Kollig 1993) Environmental Fate Rate Constants, k, or Half-Lives, t.: Volatilization: t. = 6, 1.2, 4.8 d in a typical pond, river and lake are 6, 1.2, and 4.8 d, respectively, with the reaeration for oxygen in typical bodies of water (Lyman et al. 1982; quoted, Howard 1989) evaporation t. = 795 min from water with an assumed 1-m depth (Basu et. al. 1983). Photolysis: Oxidation: rate constant k, for gas-phase second order rate constants, kOH for reaction with OH radical, kNO3 with NO3 radical and kO3 with O3 or as indicated, *data at other temperatures see reference: k < 1 . 108 M–1 h–1 for singlet oxygen, and 36 M–1 h–1 for peroxy radical at 25°C (Mabey et al. 1982) t. = 4.0 h for photooxidation in the troposphere (Callahan et al. 1979) kOH = (40.6 ± 4.1) . 10–13 cm3 molecule–1 s–1 at 299 K (flash photolysis-resonance fluorescence technique, Harris et al. 1981) kO3 < 1 . 10–19 cm3 molecule–1 s–1 at 296 ± 2 K, and tropospheric lifetimes, . > 115 d and . = 3 d due to reactions with O3 and OH radical, respectively (Atkinson et al. 1982) kO3 < 1 . 10–19 cm3 molecule–1 s–1 at 296 ± 2 K (Atkinson et al. 1983; quoted, Atkinson & Carter 1984) t. = 3.5 d for the reaction with photochemically produced hydroxyl radical by the sunlight (Edney et al. 1983; quoted, Howard 1989) kOH = 4.8 . 10–12 cm3 molecule–1 s–1 at 298.7 K, and kOH = 3.4 . 10–12 cm3 molecule–1 s–1 at 296 K (review, flash photolysis-resonance fluorescence technique Atkinson 1985) photooxidation t. = 3.4–189 h, based on measured rate constant for the reaction with hydroxyl radical in air (Howard et al. 1991) kOH = (3.4 – 4.80) . 10–12 cm3 molecule–1 s–1 at 296–298.2 K (review, Atkinson 1989) © 2006 by Taylor & Francis Group, LLC 3212 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals Hydrolysis: k(acid) = 4.2 . 10–2 M–1 h–1 at pH 5.0 with t. = 188 yr and k(base) = 6.1 . 10–2 M–1 h–1 at pH 9.0 with t. = 13 yr (Ellington et al. 1987; quoted, Howard et al. 1991, Kollig 1993); t. = 1210 yr at pH 7.0, based on measured acid and base catalyzed hydrolysis constants (Ellington et al. 1987; quoted, Howard et al. 1991) t. = 69 d at pH 2, t. = 440000 d at pH 7 and t. = 4.7 d at pH 12 in natural waters (Capel & Larson 1995). Biodegradation: t.(aq. aerobic) = 30–552 h, based on river die-away test data (Going et al. 1979; Ludzack et al. 1958; quoted, Howard et al. 1991); t.(aq. anaerobic) = 120–2208 h, based on estimated aqueous aerobic biodegradation half-life (Howard et al. 1991) 14C labeled acrylonitrile at concentrations up to 100 ppm was completely degraded within 2.0 d in a London soil under aerobic conditions (Donberg et al. 1992) t.(aerobic) = 1.3 d, t.(anaerobic) = 5 d in natural waters (Capel & Larson 1995) Biotransformation: k = of 3 . 10–9 mL cell–1 h–1 for bacterial transformation in water (Mabey et al. 1982). Bioconcentration, Uptake (k1) and Elimination (k2) Rate Constants: Half-Lives in the Environment: Air: t. = 4.0 h for photooxidation in the troposphere (Callahan et al. 1979); t. = 3.5 d for the reaction with photochemically produced hydroxyl radical by the sunlight (Edney et al. 1983; quoted, Howard 1989); photooxidation t. = 13.4–189 h, based on measured rate constant for the reaction with hydroxyl radicals in air (Atkinson 1985; quoted, Howard et al. 1991); atmospheric transformation lifetime was estimated to be 1 – 5 to > 5 d (Kelly et al. 1994). Surface water: t. = 30–552 h, based on estimated aqueous aerobic biodegradation half-life (Howard et al. 1991) Biodegradation t.(aerobic) = 100 d, t.(anaerobic) = 400 d; hydrolysis t. = 69 d at pH 2, t. = 440000 d at pH 7 and t. = 4.7 d at pH 12 in natural waters (Capel & Larson 1995). Groundwater: t. = 60–1104 h based on estimated aqueous aerobic biodegradation half-life (Howard et al. 1991). Sediment: Soil: t. < 10 d in soil (USEPA 1979; quoted, Ryan et al. 1988); t. = 30–552 h based on estimated aqueous aerobic biodegradation half-life (Howard et al. 1991). Biota: TABLE 16.1.1.4.1 Reported aqueous solubilities and vapor pressures of acrylonitrile at various temperatures Aqueous solubility Vapor pressure Othmer Encyclopedia Stephenson 1994 Stull 1947 Gudkov et al. 1964 Basu et al. 1983 shake flask-GC summary of literature data in Boublik et al. 1984 t/°C S/g·m–3 t/°C S/g·m–3 t/°C P/Pa t/°C P/Pa 0 72000 0 65800 –51.0 133.3 20 11732 20 73500 10 66800 –30.7 666.6 30 18932 40 79000 20 69000 –20.3 1333 40 27998 60 91000 30 66400 –9.0 2666 50 38530 40 68800 3.8 5333 60 57328 50 73600 11.8 7999 70 78660 60 73900 22.8 13332 70 85600 38.7 26664 58.3 53329 78.5 101325 mp/°C –82.0 © 2006 by Taylor & Francis Group, LLC Nitrogen and Sulfur Compounds 3213 FIGURE 16.1.1.4.1 Logarithm of mole fraction solubility (ln x) versus reciprocal temperature for acrylonitrile. FIGURE 16.1.1.4.2 Logarithm of vapor pressure versus reciprocal temperature for acrylonitrile. Acrylonitrile: solubility vs. 1/T -4.5 -4.0 -3.5 -3.0 -2.5 0.0026 0.0028 0.003 0.0032 0.0034 0.0036 0.0038 1/(T/K) x nl Basu et al. 1983 Stephenson 1994 Veith et al. 1980 Acrylonitrile: vapor pressure vs. 1/T 0.0 1.0 2.0 3.0 4.0 5.0 6.0 7.0 8.0 0.0026 0.003 0.0034 0.0038 0.0042 0.0046 0.005 0.0054 1/(T/K) P( gol S ) aP/ Gudkov et al. 1964 Stull 1947 b.p. = 77.3 °C m.p. = -83.48 °C © 2006 by Taylor & Francis Group, LLC 3214 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals 16.1.1.5 Benzonitrile Common Name: Benzonitrile Synonym: benzenecarbonitrile, cyanobenzene, phenyl cyanide Chemical Name: benzonitrile, benzoic acid nitrile CAS Registry No: 100-47-0 Molecular Formula: C6H5CN Molecular Weight: 103.122 Melting Point (°C): –13.99 (Lide 2003) Boiling Point (°C): 191.1 (Lide 2003) Density (g/cm3 at 20°C): 1.0006 (25°C, Dean 1985; Riddick et al. 1986) Molar Volume (cm3/mol): 103.1 (25°C, calculated-density) 107.9 (calculated-Le Bas method at normal boiling point) Dissociation Constant, pKa: Enthalpy of Vaporization, .HV (kJ/mol): 55.48, 45.94 (25°C, bp, Riddick et al. 1986) Enthalpy of Fusion, .Hfus (kJ/mol): 10.88 (Riddick et al. 1986) Entropy of Fusion, .Sfus (J/mol K): Fugacity Ratio at 25°C (assuming .Sfus = 56 J/mol K), F: 1.0 Water Solubility (g/m3 or mg/L at 25°C or as indicated. Additional data at other temperatures designated * are compiled at the end of this section): 4330 (shake flask-UV, McGowan et al. 1966) 2000 (Dean 1985; Riddick et al. 1986) 10000 (selected, Yaws et al. 1990) 4000* (shake flask-GC/TC, measured range 0–90°C, Stephenson 1994) Vapor Pressure (Pa at 25°C and reported temperature dependence equations. Additional data at other temperatures designated * are compiled at the end of this section): 133.3* (38.4°C, static method, measured range 38.4–190.6°C, Kahlbaum 1898) 133.3* (28.2°C, summary of literature data, temp range 28.2–190.6°C, Stull 1947) log (P/mmHg) = [–0.2185 . 11341.0/(T/K)] + 8.239760; temp range: 28.2–190.6°C (Antoine eq., Weast 1972–73) 78.86 (calculated-Antoine eq., Dean 1985, 1992) log (P/mmHg) = 6.74631 – 1436.72/(181 + t/°C), temp range: liquid (Antoine eq., Dean 1985, 1992) 100.0 (Riddick et al. 1986) log (P/kPa) = 5.87121 – 1436.72/(181.0 + t/°C), temp range not specified (Antoine eq., Riddick et al. 1986) 106.0 (extrapolated-Antoine eq., Stephenson & Malanowski 1987) log (PL/kPa) = 6.79506 – 2066.71/(–32.19 + T/K), temp range 301–464 K (Antoine eq.-I, Stephenson & Malanowski 1987) Henry’s Law Constant (Pa·m3/mol at 25°C): 55.32 (computed-vapor-liquid equilibrium VLE data, Yaws et al. 1991) Octanol/Water Partition Coefficient, log KOW: 1.56 (shake flask-UV spectrophotometry, Fujita et al. 1964; quoted, Leo et al. 1969; Hansch & Leo 1979) 1.56 (shake flask-UV, Holmes & Lough 1976) N © 2006 by Taylor & Francis Group, LLC Nitrogen and Sulfur Compounds 3215 1.67 (calculated-fragment const., Rekker 1977) 1.56 (shake flask at pH 7, Unger et al. 1978) 1.66 (RP-HPLC-k. correlation, Miyake & Terada 1982) 1.65 ± 0.01 (HPLC-RV correlation-ALPM, Garst & Wilson 1984) 1.50 (HPLC-k. correlation, Haky & Young 1984) 1.56 (shake flask-GC, Tanii & Hashimoto 1984) 1.56 (RP-HPLC-capacity ratio, Minick et al. 1988) 1.45 (RP-HPLC-RT correlation, ODS column with masking agent, Bechalany et al. 1989) 1.56 (recommended, Sangster 1989, 1993) 1.56 (shake flask-GC, Alcorn et al. 1993) 1.56 (recommended, Hansch et al. 1995) Octanol/Air Partition Coefficient, log KOA: 4.46 (head-space GC, Abraham et al. 2001) Bioconcentration Factor, log BCF: Sorption Partition Coefficient, log KOC: Environmental Fate Rate Constants, k, or Half-Lives, t.: Volatilization: Photolysis: Oxidation: rate constant k; for gas-phase second order rate constants, kOH for reaction with OH radical, kNO3 with NO3 radical and kO3 with O3 or as indicated, *data at other temperatures see reference: kOH = 3.3 . 10–13 cm3 molecule–1 s–1 at room temp. (Zetzsch 1982; Atkinson 1989) kOH(calc) = 4.2 . 10–13 cm3 molecule–1 s–1 at room temp. (Atkinson 1985) kOH(calc) = 3.9 . 10–13 cm3 molecule–1 s–1 at room temp. (Atkinson et al. 1985) kOH(calc) = 3.6 . 10–13 cm3 molecule–1 s–1, kOH(obs) = 3.3 . 10–13 cm3 molecule–1 s–1 at room temp. (SAR structure-activity relationship, Atkinson 1987) kOH(calc) = 4.1 . 10–13 cm3 molecule–1 s–1 (molecular orbital calculations, Klamt 1993) Hydrolysis: Biodegradation: Biotransformation: Bioconcentration, Uptake (k1) and Elimination (k2) Rate Constants: Half-Lives in the Environment: Surface water: an estimated t. = 1.3 d in Rhine River in case of first order reduction process (Zoeteman et al. 1980) TABLE 16.1.1.5.1 Reported aqueous solubilities and vapor pressures of butyronitrile at various temperatures Aqueous solubility Vapor pressure Stephenson 1994 Kahlbaum 1898* Stull 1947 shake flask-GC static-manometer summary of literature data t/°C S/g·m–3 t/°C P/Pa t/°C P/Pa t/°C P/Pa 0 3500 38.4 133.3 141.4 26664 28.2 133.3 10 3300 45.3 266.6 155.8 39997 55.3 666.6 20 4000 50.0 400.0 165.8 53329 69.2 1333 40 4500 53.8 533.3 174.4 66661 83.4 2666 50 3800 56.9 666.6 181.6 79993 99.6 5333 60 4200 69.1 1333.2 187.7 93326 109.8 7999 (Continued) © 2006 by Taylor & Francis Group, LLC 3216 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals TABLE 16.1.1.5.1 (Continued) Aqueous solubility Vapor pressure Stephenson 1994 Stull 1947 Meyer et al. 1971 Meyer & Hotz 1976 shake flask-GC summary of literature data ebulliometry ebulliometry t/°C S/g·m–3 t/°C P/Pa t/°C P/Pa t/°C P/Pa 70 6000 83.0 2666.4 190.6 101325 123.5 13332 80 9500 92.1 3999.7 144.1 26664 90 9100 98.5 5332.9 *complete list see ref. 156.7 53329 103.9 6666.1 190.6 101325 .Hsol/(kJ mol–1) 113.7 9999.2 25 EC 121.3 13332 mp/EC –12.9 FIGURE 16.1.1.5.1 Logarithm of mole fraction solubility (ln x) versus reciprocal temperature for benzonitrile. Benzonitrile: solubility vs. 1/T -8.0 -7.5 -7.0 -6.5 -6.0 0.0026 0.0028 0.003 0.0032 0.0034 0.0036 0.0038 1/(T/K) x n l Stephenson 1994 McGowan et al. 1966 © 2006 by Taylor & Francis Group, LLC Nitrogen and Sulfur Compounds 3217 FIGURE 16.1.1.5.2 Logarithm of vapor pressure versus reciprocal temperature for benzonitrile. Benzonitrile: vapor pressure vs. 1/T 0.0 1.0 2.0 3.0 4.0 5.0 6.0 7.0 8.0 0.0018 0.0022 0.0026 0.003 0.0034 0.0038 0.0042 1/(T/K) log(PS/Pa) Kahlbaum 1898 Stull 1947 b.p. = 191.1 °C m.p. = -13.99 °C © 2006 by Taylor & Francis Group, LLC 3218 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals 16.1.2 ALIPHATIC AMINES 16.1.2.1 Dimethylamine Common Name: Dimethylamine Synonym: aminomethylmethane, N-methylmethanamine Chemical Name: aminomethylmethane, dimethylamine CAS Registry No: 124-40-3 Molecular Formula: C2H7N, CH3NHCH3 Molecular Weight: 45.084 Melting Point (°C): –92.18 (Lide 2003) Boiling Point (°C): 6.88 (Lide 2003) Density (g/cm3 at 20°C): 0.6804 (0°C, Weast 1982–83) 0.6556, 0.6496 (20°C, 25°C, Riddick et al. 1986) Molar Volume (cm3/mol): 68.8 (20°C, calculated-density) 67.5 (calculated-Le Bas method at normal boiling point) Dissociation Constant, pKa: 10.732 (Perrin 1965; Weast 1982–83; Howard 1990) 10.77 (protonated cation + 1, Dean 1985) 10.77 (Sangster 1989) Enthalpy of Vaporization, .HV (kJ/mol): 23.84, 24.61 (25°C, bp, Dreisbach 1961) 23.65, 24.61 (25°C, bp, Riddick et al. 1986) Enthalpy of Fusion, .Hfus (kJ/mol): 5.941 (Riddick et al. 1986) Entropy of Fusion, .Sfus (J/mol K): Fugacity Ratio at 25°C (assuming .Sfus = 56 J/mol K), F: 1.0 Water Solubility (g/m3 or mg/L at 25°C): very soluble (Dean 1985) 620000 (selected, Yaws et al. 1990) miscible (Stephenson 1993b) Vapor Pressure (Pa at 25°C and reported temperature dependence equations. Additional data at other temperatures designated * are compiled at the end of this section): 101141* (280.018 K, static method, measured range 201.387–280.018 K, Ashton et al. 1939) 236420* (extrapolated-regression of tabulated data, temp range –87.2 to + 7.4°C, Stull 1947) 196800 (calculated by formula, Dreisbach 1961) log (P/mmHg) = 7.06396 – 1024.4/(238.0 + t/°C), temp range –55 to 37°C, (Antoine eq. for liquid state, Dreisbach 1961) log (P/mmHg) = [–0.2185 . 6660.0/(T/K)] + 7.995166; temp range –87.7 to 162.6°C, (Antoine eq., Weast 1972–73) 172220 (20°C, Verschueren 1983) 206180 (extrapolated-Antoine eq., Boublik et al. 1984) log (P/kPa) = 6.21132 – 962.001/(221.852 + t/°C), temp range –71.77 to 6.858°C (Antoine eq. from reported exptl. data, Boublik et al. 1984) 202620 (Daubert & Danner 1985) 206000 (extrapolated-Antoine eq., Dean 1985, 1992) log (P/mmHg) = 7.08212 – 960.242/(221.67 + t/°C), temp range –72 to 6°C (Antoine eq., Dean 1985, 1992) HN © 2006 by Taylor & Francis Group, LLC Nitrogen and Sulfur Compounds 3219 196800 (quoted lit., Riddick et al. 1986) log (P/kPa) = 6.18886 – 1-024.40/(238.0 + t/°C), temp range not specified (Antoine eq., Riddick et al. 1986) 205300 (interpolated-Antoine eq-II., Stephenson & Malanowski 1987) log (PL/kPa) = 6.29031 – 993.586/(–48.12 + T/K), temp range 201–280 K (Antoine eq.-I, Stephenson & Malanowski 1987) log (PL/kPa) = 6.20646 – 965.728/(–50.151 + T/K), temp range 277–360 K (Antoine eq.-II, Stephenson & Malanowski 1987) log (PL/kPa) = 7.81489 – 2369.425/(141.433 + T/K), temp range 358–438 K (Antoine eq.-III, Stephenson & Malanowski 1987) log (P/mmHg) = 36.9182 – 2.4965 . 103/(T/K) – 10.417·log (T/K) – 1.6287 . 10–9·(T/K) + 4.6496 . 10–6·(T/K)2; temp range 181–438 K (vapor pressure eq., Yaws 1994) Henry’s Law Constant (Pa·m3/mol at 25°C): 1.796 (exptl., Hine & Mookerjee 1975; quoted, Howard 1990) 1.796, 1.03 (calculated-group contribution, calculated-bond contribution, Hine & Mookerjee 1975) 2.718 (calculated-molecular structure, Russell et al. 1992) Octanol/Water Partition Coefficient, log KOW: –0.38 (shake flask-RC at pH 13, Wolfenden 1978) –0.38 (Hansch & Leo 1985) –0.38 (recommended, Sangster 1989; 1993) –0.38 (recommended, Hansch et al. 1995) Octanol/Air Partition Coefficient, log KOA: 2.00 (calculated-Soct and vapor pressure P, Abraham et al. 2001) Bioconcentration Factor, log BCF: –0.523 (calculated-KOW, Lyman et al. 1982; quoted, Howard 1990) Sorption Partition Coefficient, log KOC: 2.638 (adsorption isotherm average for five soils, Rao & Davidson 1982; quoted, Howard 1990) 0.602; 2.212; 2.706 (Podzol soil; Alfisol soil; sediment, von Oepen et al. 1991) 2.63 (soil, calculated-MCI, Sabljic et al. 1995) Environmental Fate Rate Constants, k, or Half-Lives, t.: Volatilization: using Henry’s law constant, t. = 35.1 h was estimated for a model river of 1 m deep flowing at 1 m/s with a wind velocity of 3 m/s (Lyman et al. 1982; selected, Howard 1990). Photolysis: Oxidation: rate constant k, for gas-phase second order rate constants, kOH for reaction with OH radical, kNO3 with NO3 radical and kO3 with O3 or as indicated: kOH = 6.54 . 10–11 cm3 molecule–1 s–1 at 299 K (Atkinson et al. 1977; quoted, Carlier et al. 1986; Atkinson 1989) photooxidation t. = 5.9 h in air was estimated for the vapor phase reaction with hydroxyl radical of 5 . 105 radicals/cm3 in air (Atkinson et al. 1978; Atkinson 1985; quoted, Howard 1990); kO3 = (2.61 ± 0.30) . 10–18 cm3 molecule–1 s–1 at 296 ± 2 K (Atkinson & Carter 1984; quoted, Atkinson 1985) kOH = 6.5 . 10–11 cm3 ± molecule–1 s–1 for the gas-phase reaction with 5 . 105 OH radicals/cm3 at room temp. having a loss rate of 2.8 d–1 (Atkinson 1985) kOH(calc) = 63 . 10–12 cm3 molecule–1 s–1 at room temp. (Atkinson 1987). Hydrolysis: Biodegradation: aqueous aerobic t. = 2–79 h, based on river die-away test data (Digeronimo et al. 1979; Dojlido 1979; selected, Howard et al. 1991); aqueous anaerobic t. = 8–316 h, based on estimated unacclimated aqueous aerobic biodegradation half-life (Howard et al. 1991). Biotransformation: Bioconcentration, Uptake (k1) and Elimination (k2) Rate Constants: © 2006 by Taylor & Francis Group, LLC 3220 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals Half-Lives in the Environment: Air: t. = 5.9 h was estimated for the vapor phase reaction with hydroxyl radical of 5 . 105 radicals/cm3 in air (Atkinson et al. 1978; Atkinson 1985; quoted, Howard 1990); photooxidation t. = 0.892–9.20 h, based on measured rate constant for the gas-phase reaction with OH radical (Atkinson 1985; quoted, Howard et al. 1991) and ozone (Tuazon et al. 1978; selected, Howard et al. 1991). Surface water: t. = 2–79 h, based on estimated unacclimated aqueous aerobic biodegradation half-life (Howard et al. 1991). Groundwater: t. = 4–158 h, based on estimated unacclimated aqueous aerobic biodegradation half-life (Howard et al. 1991). Sediment: Soil: t. = 86–336 h, based on soil die-away test data (Tate & Alexander 1976; Greene et al. 1981; selected, Howard et al. 1991). Biota: TABLE 16.1.2.1.1 Reported vapor pressures of dimethylamine at various temperatures and the coefficients for the vapor pressure equations log P = A – B/(T/K) (1) ln P = A – B/(T/K) (1a) log P = A – B/(C + t/°C) (2) ln P = A – B/(C + t/°C) (2a) log P = A – B/(C + T/K) (3) log P = A – B/(T/K) – C·log (T/K) (4) log P = A – B/(T/K) – C log (T/K) + D·(T/K) – E·(T/K)2 + F·(T/K)3 (5) Ashton et al. 1939 Stull 1947 static method summary of literature data T/K P/Pa t/°C P/Pa 201.387 648 bp/K 280.04 –87.7 133.3 213.802 1959 mp/K 180.97 –72.2 666.6 222.078 3780 .HV/(kJ mol–1) = 26.48 (bp) –64.6 1333 232.137 7775 .Hfus/(kJ mol–1) = 5.94 (mp) –56.0 2666 242.078 14743 –46.7 5333 249.640 22949 eq. 5 P/mmHg –40.7 7999 256.449 33269 A 32.26370 –32.6 13332 262.977 46404 B 2460.10 –20.4 26664 270.182 65491 C 8.6390 –7.1 53329 275.934 84860 D 7.6055.10–3 7.4 101325 279.980 100974 E 3.51389.10–5 277.680 91519 F 5.3241.10–8 mp/°C –96.0 280.018 101141 © 2006 by Taylor & Francis Group, LLC Nitrogen and Sulfur Compounds 3221 FIGURE 16.1.2.1.1 Logarithm of vapor pressure versus reciprocal temperature for dimethylamine. Dimethylamine: vapor pressure vs. 1/T 0.0 1.0 2.0 3.0 4.0 5.0 6.0 7.0 8.0 0.0034 0.0038 0.0042 0.0046 0.005 0.0054 0.0058 1/(T/K) P ( gol S ) aP/ Aston et al. 1939 Stull 1947 b.p. = 6.88 °C m.p. = -92.18 °C © 2006 by Taylor & Francis Group, LLC 3222 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals 16.1.2.2 Trimethylamine Common Name: Trimethylamine Synonym: dimethylamino methane, TMA Chemical Name: trimethylamine CAS Registry No: 75-50-3 Molecular Formula: C3H9N, CH3N(CH3)2 Molecular Weight: 59.110 Melting Point (°C): –117.1 (Lide 2003) Boiling Point (C): 2.87 (Lide 2003) Density (g/cm3 at 20°C): 0.6356 (Weast 1982–83) Molar Volume (cm3/mol): 93 (20°C, calculated-density) 93.3 (calculated-Le Bas method at normal boiling point) Dissociation Constant, pKa: 9.801, 9.987 (Perrin 1972; quoted, Howard 1990) 9.80 (pKa, protonated cation + 1, Dean 1985) 9.79 (pKa, Sangster 1989) Enthalpy of Vaporization, .HV (kJ/mol): 22.85, 24.13 (25°C, bp, Dreisbach 1961) Enthalpy of Fusion, .Hfus (kJ/mol): Entropy of Fusion, .Sfus (J/mol K): Fugacity Ratio at 25°C (assuming .Sfus = 56 J/mol K), F: 1.0 Water Solubility (g/m3 or mg/L at 25°C) or as indicated: 410000 (Dean 1985) 890000 (30°C, Howard 1990) 291000 (selected, Yaws et al. 1990) miscible (Stephenson 1993b) Vapor Pressure (Pa at 25°C or as indicated and reported temperature dependence equations. Additional data at other temperatures designated * are compiled at the end of this chapter): 221715* (isoteniscope, measured range 0–40°C, Swift & Hochanadel 1945) log (P/mmHg) = 24.91300 – 2018.37/(T/K) – 6.0303 · log (T/K); temp range 0–40°C (isoteniscope method, Swift & Hochanadel 1945) 265200* (extrapolated-regression of tabulated data, temp range –97.1 to + 2.9°C, Stull 1947) 226540 (calculated by formula, Dreisbach 1961) log (P/mmHg) = 6.97038 – 968.7/(234.0 + t/°C), temp range –58 to 32°C (Antoine eq. for liquid state, Dreisbach 1961) log (P/mmHg) = [–0.2185 . 6361.7/(T/K)] + 7.952370; temp range –97.1 to 2.9°C (Antoine eq., Weast 1972–73) 192500 (20°C, 30°C, Verschueren 1983) 219300, 221800 (extrapolated-Antoine eq., interpolated-Antoine eq., Boublik et al. 1984) log (P/kPa) = 5.98554 – 1957.276/(237.664 + t/°C), temp range –80.3 to 3.45°C (Antoine eq. from reported exptl. data, Boublik et al. 1984) log (P/kPa) = 5.87712 – 894.366/(228.276 + t/°C), temp range 0–40°C (Antoine eq. from reported exptl. data, Boublik et al. 1984) 214200 (Daubert & Danner 1985) 219000 (extrapolated-Antoine eq., Dean 1985, 1992) log (P/mmHg) = 6.85755 – 955.94/(237.52 + t/°C), temp range –80 to 3°C (Antoine eq., Dean 1985, 1992) 219900 (extrapolated-Antoine eq., Stephenson & Malanowski 1987) N © 2006 by Taylor & Francis Group, LLC Nitrogen and Sulfur Compounds 3223 log (PL/kPa) = 6.01402 – 968.978/(–34.253 + T/K), temp range 192–277 K (Antoine eq., Stephenson & Malanowski 1987) log (P/mmHg) = 58.6807 – 2.686 . 103/(T/K) – 20.36·log (T/K) + 1.3131 . 10–2·(T/K) – 6.563 . 10–13·(T/K)2; temp range 156–433 K (vapor pressure eq., Yaws 1994) Henry’s Law Constant (Pa·m3/mol at 25°C): 6.672 (exptl., Hine & Mookerjee 1975) 12.71, 2.16 (calculated-group contribution, calculated-bond contribution, Hine & Mookerjee 1975) 15.64 (calculated-molecular structure, Russell et al. 1992) Octanol/Water Partition Coefficient, log KOW: 0.27 (shake flask-TN, Sandell 1962; quoted, Leo et al. 1971) 0.27; 0.20 (calculated-f const., calculated-. const., Rekker 1977) 0.16 (shake flask, Hansch & Leo 1985) 0.16 (recommended, Sangster 1989) 0.16 (recommended, Hansch et al. 1995) Octanol/Air Partition Coefficient, log KOA: Bioconcentration Factor, log BCF: < 0.0 (estimated-KOW, Lyman et al. 1982; quoted, Howard 1990) Sorption Partition Coefficient, log KOC: 1.462 (soil, estimated-KOW, Lyman et al. 1982; quoted, Howard 1990) 0.602 (soil, estimated-solubility, Lyman et al. 1982; quoted, Howard 1990) 0.778; 2.365; 2.831 (Podzol soil; Alfisol soil;, sediments von Oepen et al. 1991) Environmental Fate Rate Constants, k, or Half-Lives, t.: Volatilization: using Henry’s law constant, t. = 11 h was estimated for a model river 1 m deep flowing at 1 m/s with a wind velocity of 3 m/s (Lyman et al. 1982; quoted, Howard 1990). Photolysis: Hydrolysis: Oxidation: rate constant k, for gas-phase second order rate constants, kOH for reaction with OH radical, kNO3 with NO3 radical and kO3 with O3 or as indicated, *data at other temperatures see reference: kOH = 6.09 . 10–11 cm3 molecule–1 s–1 at 299 K (Atkinson et al. 1977; Atkinson 1989) photooxidation t. = 62 d in water, based on rate constant k = 1.3 . 1010 L mol–1 s–1 for the reaction with photochemically produced hydroxyl radicals of 1 . 10–17 mol · L–1 in water (Mill et al. 1980; Guesten et al. 1981; quoted, Howard 1990) kOH = 6.10 . 10–11 cm3 molecule–1 s–1 for the gas-phase reaction with 1 . 106 OH radicals/cm3 with a loss rate of 5.0 d–1 and rate constant kO3 = 9.70 . 10–18 cm3 molecule–1 s–1 for the gas-phase reaction with 7 . 1011 O3 molecules/cm3 with a loss rate of 0.6 d–1 both at room temp. (Atkinson & Carter 1984) calculated kOH = 64 . 10–12 cm3 molecule–1 s–1 at room temp. (SAR, Atkinson 1987). Biodegradation: Biotransformation: Bioconcentration, Uptake (k1) and Elimination (k2) Rate Constants: Half-Lives in the Environment: Air: photooxidation t. = 4.0 h, based on rate constant k = 6.09 . 10–11 cm3 molecule–1 s–1 for the vapor-phase reaction with photochemically produced hydroxyl radical of 8 . 105 radicals/cm3 in air at 25.5°C and t. = 1.4 d, based on rate constant k = 9.73 . 10–18 cm3 molecule–1 s–1 for the vapor-phase reaction with ozone of 6 . 1011 molecules/cm3 in air at 24.4°C (Atkinson 1985; GEMS 1986; quoted, Howard 1990). Surface water: t. = 62 d, based on rate constant k = 1.3 . 1010 L mol–1 s–1 for the reaction with photochemically produced hydroxyl radicals of 1 . 10–17 mol L–1 in water (Mill et al. 1980; Guesten et al. 1981; quoted, Howard 1990). © 2006 by Taylor & Francis Group, LLC 3224 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals TABLE 16.1.2.2.1 Reported vapor pressures of trimethylamine at various temperatures and the coefficients for the vapor pressure equations log P = A – B/(T/K) (1) ln P = A – B/(T/K) (1a) log P = A – B/(C + t/°C) (2) ln P = A – B/(C + t/°C) (2a) log P = A – B/(C + T/K) (3) log P = A – B/(T/K) – C·log (T/K) (4) Aston et al. 1944 Swift & Hochanadel 1945 Stull 1947 static method isoteniscope summary of literature data t/°C P/Pa t/°C P/Pa t/°C P/Pa –80.315 805 0 91059 –97.1 133.3 –74.081 1367 15 158520 –81.7 666.6 –62.339 3354 20 188651 –73.8 1333 –51.938 6777 25 221715 –65.0 2666 –46.842 9305 30 259444 –55.2 5333 –41.774 12548 35 302107 –48.8 7999 –35.617 17684 40 349437 –40.3 13332 –28.507 25624 –27.0 26664 –24.155 31772 bp/K 276.03 –12.5 53329 –23.067 33494 2.90 101325 –20.164 38401 eq. 4 P/mmHg –15.974 46505 A 24.91300 mp/°C –117.1 –11.422 56802 B 2018.37 –8.985 63039 C 6.0303 –7.399 67346 –3.113 80208 .HV/(kJ mol–1) = 23.93 0.780 93495 at bp 2.928 101526 3.454 103611 FIGURE 16.1.2.2.1 Logarithm of vapor pressure versus reciprocal temperature for trimethylamine. Trimethylamine: vapor pressure vs. 1/T 0.0 1.0 2.0 3.0 4.0 5.0 6.0 7.0 8.0 0.003 0.0034 0.0038 0.0042 0.0046 0.005 0.0054 0.0058 1/(T/K) P( gol S ) aP / Aston et al. 1944 Swift & Hochanadel 1945 Stull 1947 b.p. = 2.87 °C © 2006 by Taylor & Francis Group, LLC Nitrogen and Sulfur Compounds 3225 16.1.2.3 Ethylamine Common Name: Ethylamine Synonym: aminoethane, ethanamine, monoethylamine Chemical Name: aminoethane, ethylamine CAS Registry No: 75-04-7 Molecular Formula: C2H7N, CH3CH2NH2 Molecular Weight: 45.084 Melting Point (°C): –80.5 (Lide 2003) Boiling Point (°C): 16.5 (Lide 2003) Density (g/cm3 at 20°C): 0.6829 (Dreisbach 1961; Weast 1982–83) 0.6769 (25°C, Dreisbach 1961) Molar Volume (cm3/mol): 65.4 (5°C, Stephenson & Malanowski 1987) 66.0 (calculated-Le Bas method at normal boiling point) Dissociation Constant, pKa: 10.79 (Perrin 1972) 10.81 (20°C, Weast 1982–83) 10.63 (protonated cation + 1, Dean 1985) 10.70 (Sangster 1989) Enthalpy of Vaporization, .HV (kJ/mol): 27.08, 27.57 (25°C, bp, Dreisbach 1961) Enthalpy of Fusion, .Hfus (kJ/mol): Entropy of Fusion, .Sfus (J/mol K): Fugacity Ratio at 25°C (assuming .Sfus = 56 J/mol K), F: 1.0 Water Solubility (g/m3 or mg/L at 25°C): miscible (Dean 1985; Howard 1990; Stephenson 1993b) Vapor Pressure (Pa at 25°C or as indicated and reported temperature dependence equations. Additional data at other temperatures designated* are compiled at the end of this section): 156200* (extrapolated-regression of tabulated data, temp range –82.3 to 16.6°C, Stull 1947) 141620 (calculated by formula, Dreisbach 1961) log (P/mmHg) = 7.3862 – 1137.30/(235.85 + t/°C); temp range –43 to 47°C (Antoine eq. for liquid state, Dreisbach 1961) 93325* (20°C, temp range 1.95 to 20°C, Bittrich et al. 1962) log (P/mmHg) = [–0.2185 . 6845.1/(T/K)] + 7.973674; temp range –82.3 to 176°C, (Antoine eq., Weast 1972–73) 121570, 172220 (20°C, 30°C, Verschueren 1983) 139100 (extrapolated-Antoine eq., Boublik et al. 1984) log (P/kPa) = 5.12561 – 559.427/(162.579 + t/°C); temp range 1.95–14.65°C (Antoine eq. from reported exptl. data, Boublik et al. 1984) 139700 (Daubert & Danner 1985) 141000 (calculated-Antoine eq., Dean 1985, 1992) log (P/mmHg) = 7.05413 – 987.31/(220.0 + t/°C); temp range –20 to 90°C (Antoine eq., Dean l985, 1992) 137500, 141200 (calculated-Antoine eq.-II, III, Stephenson & Malanowski 1987) log (PL/kPa) = 6.57462 – 1167.57/(–34.18 + T/K); temp range 213–297 K (Antoine eq.-I, Stephenson & Malanowski 1987) log (PL/kPa) = 6.43082 – 1140.62/(–32.433 + T/K); temp range 290–449 K (Antoine eq.-II, Stephenson & Malanowski 1987) NH2 © 2006 by Taylor & Francis Group, LLC 3226 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals log (PL/kPa) = 6.21526 – 1009.66/(–49.804 + T/K); temp range 291–367 K (Antoine eq.-III, Stephenson & Malanowski 1987) log (PL/kPa) = 6.48782 – 1176.995/(–26.674 + T/K); temp range 377–456 K (Antoine eq.-IV, Stephenson & Malanowski 1987) 140900 (calculated-Cox eq., Chao et al. 1990) log (P/mmHg) = 33.2962 – 2.4307 . 103/(T/K) – 9.0779·log (T/K) – 1.3848 . 10–9·(T/K) + 3.8183 . 10–6·(T/K)2; temp range 192–456 K (vapor pressure eq., Yaws 1994) Henry’s Law Constant (Pa·m3/mol at 25°C): 1.012 (partial pressure, Butler & Ramchandani 1935) 0.683 (exptl., Hine & Mookerjee 1975) 0.859, 0.730 (calculated-group contribution, calculated-bond contribution, Hine & Mookerjee 1975) 0.421 (calculated-molecular structure, Russell et al. 1992) Octanol/Water Partition Coefficient, log KOW: –0.30 (shake flask-titration with ion correction, Korenman et al. 1973) –0.16, –0.14; –0.19 (calculated-fragment const.; calculated-. const., Rekker 1977) –0.13 (Hansch & Leo 1985) –0.13 (recommended, Sangster 1989) –0.14 (calculated-CLOGP, Jackel & Klein 1991) –0.13 (recommended, Hansch et al. 1995) Octanol/Air Partition Coefficient, log KOA: Bioconcentration Factor, log BCF: < 0.0 (estimated-KOW, Lyman et al. 1982; quoted, Howard 1990) Sorption Partition Coefficient, log KOC: Environmental Fate Rate Constants, k, or Half-Lives, t.: Volatilization: using Henry’s law constant, t. = 2.0 d was estimated for a model river of 1 m deep flowing at 1 m/s with a wind velocity of 3 m/s (Howard 1990). Photolysis: Oxidation: rate constant k, for gas-phase second order rate constants, kOH for reaction with OH radical, kNO3 with NO3 radical and kO3 with O3 or as indicated, *data at other temperatures see reference: photooxidation t. > 9.9 d for the gas-phase reaction with OH radical in air, based on the rate of disappearance of hydrocarbon due to reaction with hydroxyl radical (Darnall et al. 1976) kOH = 2.77 . 10–11 cm3·molecules–1·s–1 at 299 K (Atkinson et al. 1977; quoted, Carlier et al. 1986) photooxidation t. = 321 d in water, based on a rate constant k = 2.5 . 109 L·mol–1·s–1 for the aqueous-phase reaction with photochemically produced OH radical of 1 . 10–17 mol·L–1 (Mill et al. 1980; Guesten et al. 1981; quoted, Howard 1990) kO3 = (2.76 ± 0.34) . 10–20 cm3·molecules–1·s–1 at 296 ± 2 K under atmospheric conditions (Atkinson & Carter 1984) kOH = 27.7 . 10–12 cm3 molecule–1 s–1 at 299.6 K (Atkinson 1989) Hydrolysis: Biodegradation: Biotransformation: Bioconcentration, Uptake (k1) and Elimination (k2) Rate Constants: Half-Lives in the Environment: Air: t. > 9.9 d for the gas-phase reaction with hydroxyl radical in air, based on the rate of disappearance of hydrocarbon due to reaction with hydroxyl radical (Darnall et al. 1976); photooxidation t. = 8.6 h, based on rate constant k = 6.54 . 10–11 cm3·molecules–1·s–1 for the vapor-phase reaction with an average hydroxyl radical of 5 . 105 radicals/cm3 at 25.5°C (Atkinson 1985; quoted, Howard 1990). © 2006 by Taylor & Francis Group, LLC Nitrogen and Sulfur Compounds 3227 Surface water: t. = 321 d, based on a rate constant k = 2.5 . 109 L·mol–1·s–1 for the aqueous-phase reaction with photochemically produced hydroxyl radical of 1 . 10–17 mol·L–1 (Mill et al. 1980; Guesten et al. 1981; quoted, Howard 1990). TABLE 16.1.2.3.1 Reported vapor pressures of ethylamine at various temperatures Stull 1947 Bittrich et al. 1962 summary of literature data t/°C P/Pa t/°C P/Pa –82.3 133.3 1.95 53329 –66.4 666.6 4.55 59995 –58.3 1333 6.85 66661 –48.6 2666 9.15 73327 –39.8 5333 11.05 79993 –33.4 7999 12.85 86659 –25.1 13332 14.65 93325 –12.3 26664 2.0 53329 16.6 101325 mp/°C –80.6 FIGURE 16.1.2.3.1 Logarithm of vapor pressure versus reciprocal temperature for ethylamine. Ethylamine: vapor pressure vs. 1/T 0.0 1.0 2.0 3.0 4.0 5.0 6.0 7.0 8.0 0.003 0.0034 0.0038 0.0042 0.0046 0.005 0.0054 1/(T/K) P( gol S ) aP/ Bittrich et al. 1962 Stull 1947 b.p. = 16.5 °C m.p. = -80.5 °C © 2006 by Taylor & Francis Group, LLC 3228 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals 16.1.2.4 Diethylamine Common Name: Diethylamine Synonym: aminoethylethane, N-ethylethanamine Chemical Name: aminoethylethane, diethylamine CAS Registry No: 109-89-7 Molecular Formula: C4H11N, CH3CH2NHCH2CH3 Molecular Weight: 73.137 Melting Point (°C): –49.8 (Lide 2003) Boiling Point (°C): 55.5 (Lide 2003) Density (g/cm3 at 20°C): 0.6993, 0.6926 (20°C, 25°C, Dreisbach. 1961) 0.7056 (Weast 1982–83) 0.7070, 0.7016 (20°C, 25°C, Riddick et al. 1986) Molar Volume (cm3/mol): 103.4 (20°C, calculated-density) 109.0 (exptl. at normal bp, Lee et al. 1972) 111.9 (calculated-Le Bas method at normal boiling point,) Dissociation Constant, pKa: 10.98 (Perrin 1965; quoted, Howard 1990) 10.80 (35°C, Perrin 1972) 10.80 (protonated cation + 1, Dean 1985) 11.07 (Sangster 1989) Enthalpy of Vaporization, .HV (kJ/mol): 31.38, 29.50 (25°C, bp, Dreisbach 1961) 31.32, 29.07 (25°C, bp, Riddick et al. 1986) Enthalpy of Fusion, .Hfus (kJ/mol): Entropy of Fusion, .Sfus (J/mol K): Fugacity Ratio at 25°C (assuming .Sfus = 56 J/mol K), F: 1.0 Water Solubility (g/m3 or mg/L at 25°C or as indicated): 815000 (14°C, quoted, Verschueren 1983) miscible (Dean 1985; Riddick et al. 1986; Yaws et al. 1990) miscible (Stephenson 1993b) Vapor Pressure (Pa at 25°C and or as indicated reported temperature dependence equations. Additional data at other temperatures designated* are compiled at the end of this section): 26664* (21°C, summary of literature data, temp range –33.0 to 55.5°C, Stull 1947) 31130 (calculated by formula, Dreisbach 1961) log (P/mmHg) = 7.14099 – 1209.9/(229.0 + t/°C); temp range –15 to 90°C (Antoine eq. for liquid state, Dreisbach 1961) 39997* (31.45°C, temp range 31.45–60.58°C, Bittrich & Kauer 1962) 31471* (25.17°C, temp range 19.73–40.22°C, Kilian & Bittrich 1965) log (P/mmHg) = [–0.2185 . 7307.5/(T/K)] + 7.701718; temp range –33.0 to 210°C (Antoine eq., Weast 1972–73) 26660, 38660 (20°C, 30°C, Verschueren 1983) 30110, 31310 (extrapolated-Antoine eq., interpolated-Antoine eq., Boublik et al. 1984) log (P/kPa) = 4.97981 – 580.448/(143.68 + t/°C); temp range 31.45–60.58°C (Antoine eq. from reported exptl. data, Boublik et al. 1984) log (P/kPa) = 5.84728 – 994.478/(203.53 + t/°C); temp range 19.758–40.22°C (Antoine eq. from reported exptl. data, Boublik et al. 1984) NH © 2006 by Taylor & Francis Group, LLC Nitrogen and Sulfur Compounds 3229 31130 (selected, Riddick et al. 1986) log (P/kPa) = 4.92649 – 583.297/(144.145 + t/°C); temp range not specified (Antoine eq., Riddick et al. 1986) 31490 (extrapolated-Antoine eq., Stephenson & Malanowski 1987) log (PL/kPa) = 5.96802 – 1058.538/(–61.331 + T/K); temp range 302–328 K (Antoine eq.-I, Stephenson & Malanowski 1987) log (PL/kPa) = 5.92678 – 1028.405/(–66.2061 + T/K); temp range 325–437 K (Antoine eq.-II, Stephenson & Malanowski 1987) log (P/mmHg) = 5.8016 – 583.3/(144.1 + t/°C); temp range 31–61°C (Antoine eq., Dean 1992) log (P/mmHg) = 32.626 – 2.4918 . 103/(T/K) – 9.3285·log (T/K) + 3.990 . 10–3·(T/K) + 1.1732 . 10–12·(T/K)2; temp range 223–497 K (vapor pressure eq., Yaws 1994) Henry’s Law Constant (Pa·m3/mol at 25°C): 2.596 (exptl., Hine & Mookerjee 1975) 2.537, 2.37 (calculated-group contribution, calculated-bond contribution, Hine & Mookerjee 1975) 6.67 (calculated-vapor liquid equilibrium VLE data, Yaws et al. 1991) Octanol/Water Partition Coefficient, log KOW: 0.43 (shake flask, Collander 1951) 0.57 (shake flask-titration, Sandell 1962) 0.60, 0.61; 0.70 (calculated-fragment const.; calculated-. const., Rekker 1977) 0.58 (Hansch & Leo 1985) 0.58 (20°C, shake flask-GC, Takayama et al. 1985) 0.81 (HPLC-k. correlation, Eadsforth 1986) 0.58 (recommended, Sangster 1989) 0.58 (recommended, Hansch et al. 1995) Octanol/Air Partition Coefficient, log KOA: Bioconcentration Factor, log BCF: 0.210 (calculated-KOW, Lyman et al. 1982; quoted, Howard 1990) Sorption Partition Coefficient, log KOC: 1.699 (soil, calculated-KOW, Lyman et al. 1982; quoted, Howard 1990) Environmental Fate Rate Constants, k, or Half-Lives, t.: Volatilization: using Henry’s law constant, t. ~ 31.6 h for a model river 1 m deep flowing at 1 m/s with a wind velocity of 3 m/s (estimated, Lyman et al. 1982; quoted, Howard 1990). Photolysis: Oxidation: photooxidation t. > 9.9 d for the gas-phase reaction with hydroxyl radical in air, based on the rate of disappearance of hydrocarbon due to reaction with OH radical (Darnall et al. 1976); photooxidation t. = 0.21 d in air, based on an estimated second-order rate constant k = 77.1 . 10–12 cm3 molecule–1 s–1 for the vapor-phase reaction with photochemically produced hydroxyl radicals of 5 . 105 radicals/cm3 in air (Atkinson 1987; quoted, Howard 1990). Hydrolysis: Biodegradation: Biotransformation: Bioconcentration, Uptake (k1) and Elimination (k2) Rate Constants: Half-Lives in the Environment: Air: t. > 9.9 d for the gas-phase reaction with hydroxyl radicals in air, based on the rate of disappearance of hydrocarbon due to reaction with hydroxyl radical (Darnall et al. 1976); t. = 0.21 d, based on an estimated rate constant k ~ 77.1 . 10–12 cm3 molecule–1 s–1 for the vapor-phase reaction with photochemically produced hydroxyl radicals of 5 . 105 radicals/cm3 in air (Atkinson 1987; quoted, Howard 1990). © 2006 by Taylor & Francis Group, LLC 3230 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals TABLE 16.1.2.4.1 Reported vapor pressures of diethylamine at various temperatures Stull 1947 Bittrich & Kauer 1962 Kilian & Bittrich 1965 summary of literature data t/°C P/Pa t/°C P/Pa t/°C P/Pa –33.0 1333 31.45 39997 19.73 24718 –22.6 2666 34.75 46663 25.17 31471 –11.3 5333 38.05 53329 30.31 39343 –4.0 7999 41.1 59995 34.99 47596 6.0 13332 43.85 66661 40.22 58582 21.0 26664 46.5 73327 38.0 53329 48.85 79993 55.5 101325 51.10 86659 53.20 93325 mp/°C –38.9 55.53 101325 57.05 106658 59.00 113324 60.58 119990 FIGURE 16.1.2.4.1 Logarithm of vapor pressure versus reciprocal temperature for diethylamine. Diethylamine: vapor pressure vs. 1/T 0.0 1.0 2.0 3.0 4.0 5.0 6.0 7.0 8.0 0.0028 0.0032 0.0036 0.004 0.0044 0.0048 1/(T/K) P( gol S ) aP / Bittrich & Kauer 1962 Kilian & Bittrich 1965 Stull 1947 b.p. = 55.5 °C m.p. = -49.8 °C © 2006 by Taylor & Francis Group, LLC Nitrogen and Sulfur Compounds 3231 16.1.2.5 n-Propylamine Common Name: Propylamine Synonym: 1-aminopropane, 1-propanamine, n-propylamine Chemical Name: aminopropane, n-propylamine CAS Registry No: 107-10-8 Molecular Formula: C3H9N, CH3CH2CH2NH2 Molecular Weight: 59.110 Melting Point (°C): –84.75 (Lide 2003) Boiling Point (°C): 47.22 (Lide 2003) Density (g/cm3 at 20°C): 0.7173 (Dreisbach 1961; Weast 1982–83; Dean 1985; Riddick et al. 1986) 0.7123 (25°C, Dreisbach 1961) Molar Volume (cm3/mol): 82.4 (liquid molar volume, Kamlet et al. 1986, 1987) 88.2 (calculated-Le Bas method at normal boiling point) Dissociation Constant, pK: 10.74, 10.789 (20°C, Perrin 1972) 10.71 (pKa, 20°C, Weast 1982–83) 10.57 (pKBH + , Dean 1985; Riddick et al. 1986) 10.68 (pKa, Sangster 1989) Enthalpy of Vaporization, .HV (kJ/mol): 31.13, 29.73 (25°C, bp, Dreisbach 1961) 31.26, 29.54 (25°C, bp, Riddick et al. 1986) Enthalpy of Fusion, .Hfus (kJ/mol): 10.974 (Riddick et al. 1986) Entropy of Fusion, .Sfus (J/mol K): Fugacity Ratio at 25°C (assuming .Sfus = 56 J/mol K), F: 1.0 Water Solubility (g/m3 or mg/L at 25°C): miscible (Dean 1985; Stephenson 1993b) miscible (Riddick et al. 1986; Howard 1990; Yaws et al. 1990) Vapor Pressure (Pa at 25°C and reported temperature dependence equations. Additional data at other temperatures designated * are compiled at the end of this section): 41800* (interpolated-regression of tabulated data, temp range –64.4 to 48.5°C, Stull 1947) 41050 (calculated by formula, Dreisbach 1961) log (P/mmHg) = 7.2672 – 1218.1/(229.9 + t/°C); temp range –20 to 81°C (Antoine eq. for liquid state, Dreisbach 1961) 42100* (ebulliometry, calculated-Antoine eq., Osborn & Douslin 1968) log (P/mmHg) = 6.92646 – 1044.028/(t/°C + 210.833); temp range 23–77.6°C (ebulliometric method, Antoine eq., Osborn & Douslin 1968) log [(P/atm) = [1 – 320.379 ± (T/K)] . 10^{0.922208 – 10.51259 . 10–4·(T/K) + 11.25530 . 10–7·(T/K)2}, temp range: 34–77.6°C (ebulliometric method, Cox eq., Osborn & Douslin 1968) log (P/mmHg) = [–0.2185 . 7408.0/(T/K)] + 7.867998; temp range –64.4 to 214.5°C (Antoine eq., Weast 1972–73) 32660 (20°C, 31°C, Verschueren 1983) 38550; 42110 (22.97°C, quoted exptl., calculated-Antoine eq., Boublik et al. 1984) log (P/kPa) = 6.05146 – 1044.082/(210.84 + t/°C); temp range 22.97–77.6°C (Antoine eq. from reported exptl. data of Osborn & Douslin 1968, Boublik et al. 1984) 42120 (calculated-Antoine eq., Dean 1985, 1992) NH2 © 2006 by Taylor & Francis Group, LLC 3232 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals log (P/mmHg) = 6.92651 – 1044.05/(210.84 + t/°C); temp range: 23–77°C (Antoine eq., Dean l985, 1992) 41050 (Riddick et al. 1986) log (P/kPa) = 6.05136 – 1044.028/(210.833 + t/°C); temp range not specified (Antoine eq., Riddick et al. 1986) 42120 (interpolated-Antoine eq., Stephenson & Malanowski 1987) log (PL/kPa) = 6.04693 – 1041.725/(–62.596 + T/K); temp range 295–351 K (Antoine eq., Stephenson & Malanowski 1987) 42125 (calculated-Cox eq., Chao et al. 1990) log (P/mmHg) = 24.6420 – 2.3152 . 103/(T/K) – 5.8711·log (T/K) – 4.6258 . 10–11·(T/K) + 1.582 . 10–6·(T/K)2; temp range 190–497 (vapor pressure eq., Yaws 1994) Henry’s Law Constant (Pa m3/mol at 25°C): 1.274 (partial pressure, Butler & Ramchandani 1935) 0.784; 0.732 (exptl.; calculated-group contribution, Hine & Mookerjee 1975) 1.330 (calculated-bond contribution, Hine & Mookerjee 1975) 0.637 (calculated-molecular structure, Russell et al. 1992) 2.01 (gas stripping-GC, Altschuh et al. 1999) Octanol/Water Partition Coefficient, log KOW: 0.28 (shake flask-GC, Korenman et al. 1973) 0.37, 0.39; 0.31‘ (calculated-f const.; calculated-. const., Rekker 1977) 0.48 (shake flask-GC, pH 13, Yakayama et al. 1985) 0.48 (recommended, Sangster 1989) 0.48 (recommended, Hansch et al. 1995) Octanol/Air Partition Coefficient, log KOA: Bioconcentration Factor, log BCF: –0.886 (estimated-KOW, Lyman et al. 1982; quoted, Howard 1990) Sorption Partition Coefficient, log KOC: < 1.699 (soil, estimated-KOW, Lyman et al. 1982; quoted, Howard 1990) Environmental Fate Rate Constants, k, or Half-Lives, t.: Volatilization: using Henry’s law constant, t. ~ 2.44 d was estimated for a model river 1 m deep flowing at 1 m/s with a wind speed of 3 m/s (estimated, Lyman et al. 1982; quoted, Howard 1990). Photolysis: Oxidation: photooxidation t. = 12 h in air, based on estimated rate constant k = 3.21 . 10–12 cm3·molecule–1·s–1 for the vapor-phase reaction with hydroxyl radical of 5 . 105/cm3 at 25°C in the atmosphere (Atkinson 1987; quoted, Howard 1990). Hydrolysis: Biodegradation: Biotransformation: Bioconcentration, Uptake (k1) and Elimination (k2) Rate Constants: Half-Lives in the Environment: Air: t. = 12 h, based on estimated second-order rate constant of 3.21 . 10–12 cm3·molecule–1·s–1 for the vaporphase reaction with hydroxyl radical of 5 . 105/cm3 at 25°C in the atmosphere (Atkinson 1987; quoted, Howard 1990). © 2006 by Taylor & Francis Group, LLC Nitrogen and Sulfur Compounds 3233 TABLE 16.1.2.5.1 Reported vapor pressures of n-propylamine at various temperatures Stull 1947 Osborn & Douslin 1968 summary of literature data ebulliometric method t/°C P/Pa t/°C P/Pa –64.4 133.3 22.973 38547 –46.3 666.6 27.750 47359 –37.2 1333 32.564 57803 –27.1 2666 37.414 70109 –16.0 5333 42.304 84525 –9.0 7999 47.229 101325 0.50 13332 52.193 120798 15.0 26664 57.195 143268 31.5 53329 62.235 169052 48.5 101325 67.314 198530 72.430 232087 mp/°C –83.0 77.587 270110 FIGURE 16.1.2.5.1 Logarithm of vapor pressure versus reciprocal temperature for n-propylamine. n -Propylamine: vapor pressure vs. 1/T 0.0 1.0 2.0 3.0 4.0 5.0 6.0 7.0 8.0 0.0026 0.003 0.0034 0.0038 0.0042 0.0046 0.005 0.0054 1/(T/K) log(PS/Pa) Osborn & Douslin 1968 Stull 1947 b.p. = 47.22 °C m.p. = -84.75 °C © 2006 by Taylor & Francis Group, LLC 3234 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals 16.1.2.6 n-Butylamine Common Name: Butylamine Synonym: 1-aminobutane, n-butylamine. 1-butanamine Chemical Name: 1-aminobutane, n-butylamine CAS Registry No: 109-73-9 Molecular Formula: C4H11N, CH3CH2CH2CH2NH2 Molecular Weight: 73.137 Melting Point (°C): –49.1 (Dreisbach 1961; Riddick et al. 1986; Stephenson & Malanowski 1987; Lide 2003) Boiling Point (°C): 77.0 (Lide 2003) Density (g/cm3 at 20°C): 0.7414 (Dreisbach 1961; Weast 1982–83) 0.7392 (Riddick et al. 1986) Molar Volume (cm3/mol): 98.8 (20°C, calculated-density) 110.4 (calculated-Le Bas method at normal boiling point) Dissociation Constant, pK: 10.77 (Perrin 1965; pKa, 20°C, Weast 1982–83; Howard 1990) 10.65 (Perrin 1972) 10.64 (pKa, protonated + 1, Dean 1985; Sangster 1989) 10.77 (pKBH + , Riddick et al. 1986) Enthalpy of Vaporization, .HV (kJ/mol): 35.54, 32.11 (25°C, bp, Dreisbach 1961) 35.74, 31.80 (25°C, bp, Riddick et al. 1986) Enthalpy of Fusion, .Hfus (kJ/mol): Entropy of Fusion, .Sfus (J/mol K): Fugacity Ratio at 25°C (assuming .Sfus = 56 J/mol K), F: 1.0 Water Solubility (g/m3 or mg/L at 25°C): miscible (Dean 1985; Howard 1990; Yaws et al. 1990) miscible (Riddick et al. 1986) miscible (Stephenson 1993b) Vapor Pressure (Pa at 25°C and reported temperature dependence equations): 13850 (Hoy 1970; Abraham 1984) 12230 (calculated by formula, Dreisbach 1961) log (P/mmHg) = 7.213 – 1308.4/(224.2 + t/°C); temp range 4–114°C (Antoine eq. for liquid state, Dreisbach 1955) 9600 (20°C, Verschueren 1983) 12230 (quoted lit., Riddick et al. 1986; quoted, Howard 1990) log (P/kPa) = 6.07009 – 1157.810/(207.80 + t/°C); temp range not specified (Antoine eq., Riddick et al. 1986) 12520 (extrapolated-Antoine eq., Stephenson & Malanowski 1987) log (PL/kPa) = 6.2635 – 1258.745/(–54.49 + T/K); temp range 313–350 K (Antoine eq., Stephenson & Malanowski 1987) log (P/mmHg) = 25.0711 – 2.5701 . 103/(T/K) – 5.8985·log (T/K) + 7.9399 . 10–10·(T/K) + 1.192 . 10–6·(T/K)2; temp range 124–532 K (vapor pressure eq., Yaws 1994) Henry’s Law Constant (Pa m3/mol at 25°C): 1.526 (partial pressure, Butler & Ramchandani 1935) 1.528 (exptl., Hine & Mookerjee 1975) NH2 © 2006 by Taylor & Francis Group, LLC Nitrogen and Sulfur Compounds 3235 1.676, 1.68 (calculated-group contribution, calculated-bond contribution, Hine & Mookerjee 1975) 0.880 (calculated-molecular structure, Russell et al. 1992) 1.785 (gas stripping-GC, Altschuh et al. 1999) Octanol/Water Partition Coefficient, log KOW: 0.68 (shake flask, Collander 1951) 0.88 (shake flask-titration, Sandell 1962) 0.81 (shake flask, unpublished result, Leo et al. 1971; Hansch & Leo 1987) 0.74 (shake flask-titration, Korenman et al. 1973) 0.90, 0.92; 0.81 (calculated-f const.; calculated-. const., Rekker 1977) 0.80 (inter-lab. shake flask average, Eadsforth & Moser 1983) 0.97 (shake flask-GC, Takayama et al. 1985) 0.86 (recommended, Sangster 1989) 0.97 (recommended, Hansch et al. 1995) Octanol/Air Partition Coefficient, log KOA: 3.61 (calculated-Soct and vapor pressure P, Abraham et al. 2001) Bioconcentration Factor, log BCF: 0.505 (calculated-KOW, Lyman et al. 1982; quoted, Howard 1990) Sorption Partition Coefficient, log KOC: 1.903 (soil, calculated-KOW, Lyman et al. 1982; quoted, Howard 1990) 1.176, 2.021, 2.029 (Podzol soil, Alfisol soil, sediment, von Oepen et al. 1991) 1.880 (soil, quoted exptl., Meylan et al. 1992) 1.780 (soil, calculated-MCI . and fragment contribution, Meylan et al. 1992) Environmental Fate Rate Constants, k, or Half-Lives, t.: Volatilization: using Henry’s law constant, t. =1.95 d was predicted for evaporation from a model river 1 m deep, flowing at 1 m/s with a wind velocity of 3 m/s (Lyman et al. 1982; quoted, Howard 1990). Photolysis: Oxidation: estimated vapor phase photooxidation t. = 0.479 d in air, based on a result of reaction with photochemically produced hydroxyl radical at a concentration of 5 . 105 radicals/cm3 (USEPA 1986; quoted, Howard 1990). Hydrolysis: Biodegradation: Biotransformation: Bioconcentration, Uptake (k1) and Elimination (k2) Rate Constants: Half-Lives in the Environment: Air: estimated vapor phase t. = 0.479 d, based on a result of reaction with photochemically produced hydroxyl radical at a concentration of 5 . 105 radicals/cm3 (USEPA 1986; quoted, Howard 1990). © 2006 by Taylor & Francis Group, LLC 3236 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals 16.1.2.7 Ethanolamine Common Name: Ethanolamine Synonym: .-aminoethyl alcohol, ethylolamine, 2-hydroxyethylamine, .-hydroxyethylamine, monoethanolamine, MEA Chemical Name: ethanolamine, 2-aminoethanol CAS Registry No: 141-43-5 Molecular Formula: C2H7NO, HOCH2CH2NH2 Molecular Weight: 61.098 Melting Point (°C): 10.5 (Lide 2003) Boiling Point (°C): 171 (Lide 2003) Density (g/cm3 at 20°C): 1.0180 (Weast 1982–83) 1.0147 (Riddick et al. 1986) Molar Volume (cm3/mol): 60.4 (Stephenson & Malanowski 1987) 73.4 (calculated-Le Bas method at normal boiling point) Dissociation Constant, pK: 9.48, 9.4994 (Perrin 1972; quoted, Howard 1990) 9.50 (pKBH + , Riddick et al. 1986) Enthalpy of Vaporization, .HV (kJ/mol): 92.09, 49.831 (25°C, bp, Riddick et al. 1986) Enthalpy of Fusion, .Hfus (kJ/mol): 20.50 (Riddick et al. 1986) Entropy of Fusion, .Sfus J/mol K: Fugacity Ratio at 25°C (assuming .Sfus = 56 J/mol K), F: 1.0 Water Solubility (g/m3 or mg/L at 25°C): miscible (Dean 1985) miscible (Riddick et al. 1986; quoted, Howard 1990) Vapor Pressure (Pa at 25°C and reported temperature dependence equations. Additional data at other temperatures deisgnated * are compiled at the end of this section): 893* (65.4°C, Ramsay-Young method, measured range 65.4–170.9°C, Matthews et al. 1950) log (P/mmHg) = 44.008 – 4089/(T/K) – 11.446 ± log (T/K); temp range 65.4–170.9°C (Kirchhoff eq., ebulliometry, Matthews et al. 1950) 8707* (106.1°C, ebulliometry, measured range 106.1–170.37°C, McDonald et al. 1959) log (P/mmHg) = 7.7380 –1772.11/(186.25 + t/°C); temp range 106–170°C, or pressure range 65.31–760 mmHg (ebulliometry, McDonald et al. 1959) 53.32 (20°C, Verschueren 1983) 41.64, 46.67 (extrapolated values-Antoine eq., Boublik et al. 1984) log (P/kPa) = 6.54175 – 1554.149/(171.175 + t/°C); temp range 65.5–170.9°C (Antoine eq. from reported exptl. data, Boublik et al. 1984) log (P/kPa) = 6.86239 – 1725.168/(185.556 + t/°C); temp range 106.1–170.37°C (Antoine eq. from reported exptl. data, Boublik et al. 1984) 42.51 (extrapolated-Antoine eq., Dean 1985, 1992) log (P/mmHg) = 7.4568 – 1577.67/(172.37 + t/°C); temp range 65–171°C (Antoine eq., Dean 1985, 1992) 48.0 (Riddick et al. 1986) log (P/kPa) = 6.86290 – 1732.11/(186.215 + t/°C); temp range not specified (Antoine eq., Riddick et al. 1986) 47.34 (extrapolated-Antoine eq., Stephenson & Malanowski 1987) log (PL/kPa) = 6.8629 – 1732.11/(–86.6 + T/K); temp range 310–444 K (liquid, Antoine eq., Stephenson & Malanowski 1987) NH2 HO © 2006 by Taylor & Francis Group, LLC Nitrogen and Sulfur Compounds 3237 34.66 (from Dow Chemical’s Handbook, Howard 1990) log (P/mmHg) = 72.9125 – 5.8595 . 103/(T/K) –21.914·log (T/K) – 7.1511 . 10–10·(T/K) + 5.9841 . 10–6·(T/K)2; temp range 284–638 K (vapor pressure eq., Yaws 1994) Henry’s Law Constant (Pa·m3/mol at 25°C): 0.0041 (calculated-bond method, Hine & Mookerjee 1975) Octanol/Water Partition Coefficient, log KOW: –1.31 (shake flask, Collander 1951) –1.29; –1.35 (calculated-f const., calculated-. const., Rekker 1977) –1.31 (recommended, Sangster 1993) –1.31 (recommended, Hansch et al. 1995) Octanol/Air Partition Coefficient, log KOA: Bioconcentration Factor, log BCF: < 0.0 (estimated-KOW, Lyman et al. 1982; quoted, Howard 1990) Sorption Partition Coefficient, log KOC: 0.699 (soil, estimated-KOW, Lyman et al. 1982; quoted, Howard 1990) Environmental Fate Rate Constants, k, or Half-Lives, t.: Volatilization: Photolysis: Hydrolysis: Oxidation: photooxidation t. = 11 h in air, based on an estimated rate constant k ~ 3.5 . 10–11 cm3 ± molecule–1 s–1 for the vapor phase reaction with photochemically produced hydroxyl radical of 5 . 105 radicals/cm3 in air (Atkinson 1987; quoted, Howard 1990). Biodegradation: Biotransformation: Bioconcentration, Uptake (k1) and Elimination (k2) Rate Constants: Half-Lives in the Environment: Air: half-life of 11 h, based on an estimated rate constant of 3.5 . 10–11 cm3 molecule–1 s–1 for the vapor phase reaction with photochemically produced hydroxyl radical of 5 . 105 radicals/cm3 in air (Atkinson 1987; quoted, Howard 1990). © 2006 by Taylor & Francis Group, LLC 3238 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals TABLE 16.1.2.7.1 Reported vapor pressures of ethanolamine at various temperatures and the coefficients for the vapor pressure equations log P = A – B/(T/K) (1) ln P = A – B/(T/K) (1a) log P = A – B/(C + t/°C) (2) ln P = A – B/(C + t/°C) (2a) log P = A – B/(C + T/K) (3) log P = A – B/(T/K) – C·log (T/K) (4) Matthews et al. 1950 McDonald et al. 1959 Ramsay-Young method ebulliometric method t/°C P/Pa t/°C P/Pa t/°C P/Pa 65.4 893 137.9 32264 106.1 8707 65.5 947 144.6 42236 108.43 10058 69.5 1160 150.0 54195 112.29 11427 70.0 1253 161.4 73860 114.55 12702 75.4 1760 170.9 100125 116.79 14049 81.1 2320 125.73 20454 86.4 3280 bp/K 444.1 159.79 71862 90.0 3813 169.20 97584 96.4 5440 .HV/(kJ mol–1) = 46.07 at bp 170.37 101325 101.7 7146 Kirchhoff, Rankine, Dupre 105.5 8559 eq. 4 P/mmHg mp/°C 10.31 112.1 11306 A 44.008 eq. 2 P/mmHg 117.3 14012 B 4809 A 7.7380 125.0 19452 C 11.446 B 173211 132.0 25771 C 186.215 FIGURE 16.1.2.7.1 Logarithm of vapor pressure versus reciprocal temperature for ethanolamine. Ethanolamine: vapor pressure vs. 1/T 0.0 1.0 2.0 3.0 4.0 5.0 6.0 7.0 8.0 0.002 0.0022 0.0024 0.0026 0.0028 0.003 0.0032 0.0034 0.0036 1/(T/K) P( gol S ) aP/ Matthews et al. 1950 McDonald et al. 1959 b.p. = 171 °C m.p. = 10.5 °C © 2006 by Taylor & Francis Group, LLC Nitrogen and Sulfur Compounds 3239 16.1.2.8 Diethanolamine Common Name: Diethanolamine Synonym: 2,2.-amino-diethanol, 3-aza-1,5-pentanediol, diethylolamine, bis(hydroxyethyl)amine, 2,2.-dihydroxydiethylamine, .,..-dihydroxydiethylamine, 2,2.-iminobisethanol, 2,2.-iminodiethanol Chemical Name: diethanolamine CAS Registry No: 111-42-2 Molecular Formula: C4H11NO2, HOCH2CH2NHCH2CH2OH Molecular Weight: 105.136 Melting Point (°C): 28.0 (Weast 1982–83; Dean 1985; Riddick et al. 1986; Stephenson & Malanowski 1987; Lide 2003) Boiling Point (°C): 268.8 (Lide 2003) Density (g/cm3 at 20°C): 1.0966 (Weast 1982–83) 1.0936 (25°C, Riddick et al. 1986) Molar Volume (cm3/mol): 96.5 (30°C, Stephenson & Malanowski 1987) 126.7 (calculated-Le Bas method at normal boiling point) Dissociation Constant, pK: 8.88, 8.97 (Perrin 1972) 8.88 (pKBH + , Dean 1985; Riddick et al. 1986) Enthalpy of Vaporization, .HV (kJ/mol): 70.3, 65.229 (25°C, bp, Riddick et al. 1986) Enthalpy of Fusion, .Hfus (kJ/mol): 25.104 (Riddick et al. 1986) Entropy of Fusion, .Sfus (J/mol K): Fugacity Ratio at 25°C (assuming .Sfus = 56 J/mol K), F: 0.934 (mp at 28°C) Water Solubility (g/m3 or mg/L at 25°C): 954000 (Verschueren 1983) 964000 (Dean 1985) 954000 (20°C, Riddick et al. 1986) miscible (from Dow Chemical’s Handbook, Howard 1990) Vapor Pressure (Pa at 25°C and reported temperature dependence equations): < 1.333 (20°C, Verschueren 1983) 0.040 (extrapolated-Antoine eq., Dean 1985, 1992) log (P/mmHg) = 8.1388 – 2327.9/(174.4 + t/°C); temp range 194–241°C (Antoine eq., Dean l985, 1992) 0.030 (quoted lit., Riddick et al. 1986) log (P/kPa) = 7.26458 – 2328.56/(174.399 + t/°C); temp range not specified (Antoine eq., Riddick et al. 1986) log (PL/kPa) = 7.26044 – 2326.23/(–98.907 + T/K); temp range: 423–542 K (liquid, Antoine eq., Stephenson & Malanowski 1987) 0.0373 (quoted from Dow Chemical’s Handbook, Howard 1990) log (P/mmHg) =122.0877 –8.8422 . 103/(T/K) –40.422·log (T/K) + 1.4062 . 10–2·(T/K) + 1.1986 . 10–12·(T/K)2; temp range 301–542 K (vapor pressure eq., Yaws 1994) Henry’s Law Constant (Pa·m3/mol at 25°C): 5.42 . 10–9 (Hine & Mookerjee 1975) HN OH HO © 2006 by Taylor & Francis Group, LLC 3240 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals Octanol/Water Partition Coefficient, log KOW: –1.43 (shake flask, Collander 1951) –1.51 (calculated-fragment const., Rekker & De Kort 1979) –1.43 (recommended, Sangster 1993) –1.43 (recommended, Hansch et al 1995) Octanol/Air Partition Coefficient, log KOA: Bioconcentration Factor, log BCF: < 0.0 (estimated-KOW, Howard 1990) Sorption Partition Coefficient, log KOC: 0.602 (soil, estimated-KOW, Howard 1990) Environmental Fate Rate Constants, k, or Half-Lives, t.: Volatilization: Photolysis: Hydrolysis: Oxidation: photooxidation t. = 0.72–7.2 h in air, based on estimated rate constant for the reaction with hydroxyl radical in air (Atkinson 1987; quoted, Howard 1990; Howard et al. 1991). Biodegradation: aqueous aerobic t. = 14.4–168 h, based on measured half-life in surface water grab sample experiment (Boethling & Alexander 1979; quoted, Howard et al. 1991) and aqueous aerobic screening test data (Gerike & Fischer 1979; Bridie et al. 1979; quoted, Howard et al. 1991); aqueous anaerobic t. = 57.6–672 h, based on estimated unacclimated aqueous aerobic biodegradation half-life (Howard et al. 1991). Biotransformation: Bioconcentration, Uptake (k1) and Elimination (k2) Rate Constants: Half-Lives in the Environment: Air: photooxidation t. = 0.72–7.2 h, based on estimated rate constant for the reaction with hydroxyl radical in air (Atkinson 1987; quoted, Howard 1990; Howard et al. 1991); atmospheric transformation lifetime by reaction with water was estimated to be < 1 d (Kelly et al. 1994). Surface water: t. = 14.4–168 h, based on estimated unacclimated aqueous aerobic biodegradation half-life (Howard et al. 1991). Groundwater: t. = 28.8–336 h, based on estimated unacclimated aqueous aerobic biodegradation half-life (Howard et al. 1991). Sediment: Soil: t. = 14.4–168 h, based on estimated unacclimated aqueous aerobic biodegradation half-life (Howard et al. 1991). Biota: © 2006 by Taylor & Francis Group, LLC Nitrogen and Sulfur Compounds 3241 16.1.2.9 Triethanolamine Common Name: Triethanolamine Synonym: 2,2.,2.-nitrilotriethanol, 2,2.,2.-nitrilotrisethanol, triethylolamine, trihydroxytriethylamine, trolamine, tris(hydroxyethyl)–amine, TEA Chemical Name: triethanolamine CAS Registry No: 102-71-6 Molecular Formula: C6H15NO3, (HOCH2CH2)3N Molecular Weight: 149.188 Melting Point (°C): 20.5 (Lide 2003) Boiling Point (°C): 335.4 (Dean 1985; Riddick et al. 1986; Stephenson & Malanowski 1987; Lide 2003) Density (g/cm3 at 20°C): 1.1242 (Weast 1982–83; Dean 1985) 1.1196 (25°C, Riddick et al. 1986) Molar Volume (cm3/mol): 133.3 (Stephenson & Malanowski 1987) 182.1 (calculated-Le Bas method at normal boiling point) Dissociation Constant, pK: 7.92 (Perrin 1972; quoted, Howard 1990) 7.76 (pKBH + , Dean 1985; Riddick et al. 1986) Enthalpy of Vaporization, .HV (kJ/mol): 67.475 (bp, Riddick et al. 1986) Enthalpy of Fusion, .Hfus (kJ/mol): 27.20 (Riddick et al. 1986) Entropy of Fusion, .Sfus (J/mol K): Fugacity Ratio at 25°C (assuming .Sfus = 56 J/mol K), F: 1.0 Water Solubility (g/m3 or mg/L at 25°C): miscible (Dean 1985; Howard 1990) miscible (Riddick et al. 1986) Vapor Pressure (Pa at 25°C and reported temperature dependence equations): < 1.33 (20°C, Verschueren 1983) 0.0131 (extrapolated-Antoine eq., Boublik et al. 1984) log (P/kPa) = 9.19319 – 4543.817/(297.839 + t/°C), temp range: 252.7–305.6°C (Antoine eq. from reported exptl. data, Boublik et al. 1984) 0.0100 (extrapolated-Antoine eq., Dean 1985, 1992) log (P/mmHg) = 10.0675 – 4542.78/(297.76 + t/°C), temp range: 252–305°C (Antoine eq., Dean l985, 1992) < 1.30 (20°C, Riddick et al. 1986) log (P/kPa) = 7.67989 – 2962.73/(186.75 + t/°C), temp range not specified (Antoine eq., Riddick et al. 1986) log (PL/kPa) = 9.53861 – 4951.87/(49.99 + T/K), temp range: 523–579 K, (Antoine eq., Stephenson & Malanowski 1987) 4.79 . 10–4 (quoted from Dow Chemical’s Handbook, Howard 1990) log (P/mmHg) = 135.3206 –1.0312 . 104/(T/K) –44.637·log (T/K) + 1.4368 . 10–2·(T/K) – 1.7552 . 10–13·(T/K)2; temp range 294–787 K (vapor pressure eq., Yaws 1994) Henry’s Law Constant (Pa·m3/mol at 25°C): 3.42 . 10–14 (Hine & Mookerjee 1975) N OH HO OH © 2006 by Taylor & Francis Group, LLC 3242 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals Octanol/Water Partition Coefficient, log KOW: –1.32, –1.75 (calculated, Verschueren 1983) –1.59 (Howard 1990) –1.00 (recommended, Hansch et al. 1995) Octanol/Air Partition Coefficient, log KOA: Bioconcentration Factor, log BCF: < 0.0 (estimated-KOW, Howard 1990) Sorption Partition Coefficient, log KOC: 0.477 (soil, estimated-KOW, Howard 1990) Environmental Fate Rate Constants, k, or Half-Lives, t.: Volatilization: Photolysis: Hydrolysis: Oxidation: photooxidation t. = 4.0 h in air, based on an estimated rate constant k ~ 10.4 . 10–11 cm3·molecule–1 s–1 for the vapor phase reaction with photochemically produced hydroxyl radical of 5 . 105 radicals/cm3 in air at 25°C (Atkinson 1987; quoted, Howard 1990). Biodegradation: Biotransformation: Bioconcentration, Uptake (k1) and Elimination (k2) Rate Constants: Half-Lives in the Environment: Air: t. = 4.0 h, based on an estimated rate constant k ~ 10.4 . 10–11 cm3 molecule–1 s–1 for the vapor phase reaction with photochemically produced hydroxyl radical of 5 . 105 radicals/cm3 in air at 25°C (Atkinson 1987; quoted, Howard 1990). © 2006 by Taylor & Francis Group, LLC Nitrogen and Sulfur Compounds 3243 16.1.3 AROMATIC AMINES 16.1.3.1 Aniline Common Name: Aniline Synonym: phenylamine, aminobenzene, benzeneamine, benzenamine Chemical Name: aniline CAS Registry No: 62-53-3 Molecular Formula: C6H5NH2 Molecular Weight: 93.127 Melting Point (°C): –6.02 (Lide 2003) Boiling Point (°C): 184.1 (Lide 2003) Density (g/cm3 at 20°C): 1.02173, 1.01750 (20°C, 25°C, Dreisbach 1955) 1.02173 (20°C, Weast 1982–83) Molar Volume (cm3/mol): 91.2 (20°C, calculated-density) 110.2 (calculated-Le Bas method at normal boiling point) Dissociation Constant, pKa: 4.596 (Perrin 1972; Howard 1989) 4.600 (McLeese et al. 1979; Riddick et al. 1986; Sangster 1989 ) 4.630 (Weast 1982–83) 4.58, 3.96 (quoted, HPLC, Miyake et al. 1987) Enthalpy of Vaporization, .HV (kJ/mol): 54.28, 43.17 (25°C, bp, Dreisbach 1955) 55.843, 44.53 (25°C, bp, Riddick et al. 1986) Enthalpy of Fusion, .Hfus (kJ/mol): Entropy of Fusion, .Sfus (J/mol K): Fugacity Ratio at 25°C (assuming .Sfus = 56 J/mol K), F: 1.0 Water Solubility (g/m3 or mg/L at 25°C): 36650 (Hill & Macy 1924) 36070 (Seidell 1941) 38670 (shake flask-residue volume method, Booth & Everson 1948) 36220 (shake flask-interferometry, Donahue & Bartell 1952) 34100 (Stephen & Stephen 1963) 36600 (Kenaga 1980) 34000 (Verschueren 1983) 56900 (calculated-activity coeff. . by UNIFAC, Fu & Luthy 1985, 1986) 33800 (selected, Riddick et al. 1986) 34200 (selected, Yaws et al. 1990) Vapor Pressure (Pa at 25°C and reported temperature dependence equations. Additional data at other temperatures designated * are compiled at the end of this section): 133.3 (43.7°C, static method, measured range 43.7–183.9°C, Kahlbaum 1898) 85.71* (extrapolated-regression of tabulated data, temp range 34.8–184.4°C Stull 1947) log (P/mmHg) = 7.57170 – 1941.7/(230 + t/°C) (Antoine eq., Dreisbach & Martin 1949) 10351* (112.92°C, ebulliometry, measured range 112.92–183.93°C, Dreisbach & Shrader 1949) 89.52 (calculated by formula, Dreisbach 1955; quoted, Riddick et al. 1986) NH2 © 2006 by Taylor & Francis Group, LLC 3244 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals log (P/mmHg) = 7.24179 – 1674.3/(200.0 + t/°C); temp range 90–250°C (Antoine eq. for liquid state, Dreisbach 1955) 6806* (102.59°C, ebulliometry, measured range 102.59–185.15°C, McDonald et al. 1959) log (P/mmHg) = 7.25375 – 1684.35/(201.175 + t/°C, temp range 103–185°C (Antoine eq., ebulliometry, McDonald et al. 1959) 133.3* (31.55°C, calculated-thermodynamic properties, temp range 31.55–184.40°C, Hatton et al. 1962) log (P/mmHg) = [–0.2185 . 11307.6/(T/K)] + 8.221995; temp range 34.8–422.4°C (Antoine eq., Weast 1972–73) 88.30 (extrapolated-Antoine eq., Boublik et al. 1973) log (P/mmHg) = 7.3201 – 1731.515/(205.049 + t/°C); temp range 102.6–185.2°C (Antoine eq. from reported exptl. data of McDonald et al.1959, Boublik et al. 1973) log (P/mmHg) = [–0.2185 . 11307.6/(T/K)] + 8.221995; temp range 34.8–422.4°C (Antoine eq., Weast 1972–73) 82.71 (calculated-Cox eq., Chao et al. 1983) log (P/atm) = [1– 457.025/(T/K)] . 10^{0.911551 – 6.64936 . 10–4·(T/K) + 5.25455 . 10–7·(T/K)2}; temp range: 267.3–695.0 K (Cox eq., Chao et al. 1983) 80 ± 6 (gas saturation-HPLC/UV, Sonnefeld et al. 1983) 40.0 (20°C, Verschueren 1983) 88.0, 48.24 (extrapolated-Antoine eq., Boublik et al. 1984) log (P/kPa) = 6.43196 – 1722.154/(205.002 + t/°C); temp range 102.6–185.2°C (Antoine eq. from reported exptl. data, Boublik et al. 1984) log (P/kPa) = 5.68977 – 1234.569/(151.207 + t/°C); temp range 112.9–183.9°C (Antoine eq. from reported exptl. data, Boublik et al. 1984) 65.18 (Daubert & Danner 1985) 89.30 (extrapolated-Antoine eq., Dean 1985, 1992) log (P/mmHg) = 7.32010 – 1731.515/(206.049 + t/°C); temp range 102–185°C (Antoine eq., Dean l985, 1992) log (P/kPa) = 5.69066 – 1941.7/(230.0 + t/°C), temp range not specified (Antoine eq., Riddick et al. 1986) 89.60 (calculated-Antoine eq., Stephenson & Malanowski 1987) log (PL/kPa) = 6.40627 – 1702.817/(–70.155 + T/K); temp range 304–458 K (Antoine eq.-I, Stephenson & Malanowski 1987) log (PL/kPa) = 8.1019 – 2728/(T/K); temp range 273–338 K (Antoine eq.-II, Stephenson & Malanowski 1987) log (PL/kPa) = 6.41147 – 1708.239/(–69.454 + T/K); temp range 373–458 K (Antoine eq.-III, Stephenson & Malanowski 1987) log (PL/kPa) = 6.44338 – 1682.348/(–78.065 + T/K); temp range: 455–523 K (Antoine eq.-IV, Stephenson & Malanowski 1987) 86.70 (calculated-Cox eq., Chao et al. 1990) log (P/mmHg) =124.3764 –7.1676 . 103/(T/K) –42.763·log (T/K) + 1.7336 . 10–2·(T/K) + 5.7138 . 10–15·(T/K)2; temp range 267–699 K (vapor pressure eq., Yaws 1994) Henry’s Law Constant (Pa·m3/mol at 25°C): 13778 (Hakuta et al. 1977) 12.16 (measured, Yoshida et al. 1983) 0.193 (gas stripping-GC, Altschuh et al. 1999) Octanol/Water Partition Coefficient, log KOW: 0.90 (shake flask-UV, Fujita et al. 1964) 0.90 (shake flask, Iwasa et al. 1965) 0.90 (shake flask-UV, Hansch et al. 1968) 0.90 (Leo et al. 1971; Hansch & Leo 1979; Hansch & Leo 1983, Hansch & Leo 1985) 0.89 (shake flask-UV at pH 5.6, Umeyama et al. 1971) 0.90 (HPLC-k. correlation, Carlson et al. 1975) 0.85 (shake flask, Lu & Metcalf 1975) 0.90 (HPLC-RT correlation, Mirrlees et al. 1976) 0.93 ± 0.05 (shake flask at pH 7, Unger et al. 1978) 0.90, 0.98, 0.85 (shake flask, Hansch & Leo 1979) 0.91 (HPLC-k. correlation, Konemann et al. 1979) 0.90 (shake flask-UV, Briggs 1981) © 2006 by Taylor & Francis Group, LLC Nitrogen and Sulfur Compounds 3245 1.03 (RP-HPLC-k. correlation, D’Amboise & Hanai 1982) 0.90 (HPLC-k. correlation, Hammers et al. 1982) 0.90 (inter-laboratory studies. shake flask average, Eadsforth & Moser 1983) 1.09 (inter-laboratory studies, HPLC-RT correlation, average, Eadsforth & Moser 1983; Brooke et al. 1990) 1.34, 1.27, 1.08 (HPLC-RT correlation, Harnish et al. 1983) 1.08 (shake flask average, OECD/EEC lab. comparison tests, Harnish et al. 1983) 0.79, 0.96 (HPLC-RV correlation-ALPM, Garst & Wilson 1984) 0.89 (shake flask-UV at pH 7.4, El Tayar et al. 1984) 0.99 (calculated-activity coeff. . from UNIFAC, Campbell & Luthy 1985) 0.81, 1.08 (HPLC-k. correlation, Eadsforth 1986) 0.91 (RP-HPLC-RT correlation, Eadsforth 1986) 0.98 (shake flask-UV at pH 7.5, Martin-Villodre et al. 1986) 0.93 (HPLC method average, Ge et al. 1987) 0.78 (HPLC-k. correlation, Miyake et al. 1987) 1.18 (calculated-activity coeff. . from UNIFAC, Banerjee & Howard 1988) 0.940 ± 0.006 ( shake flask/slow-stirring-GC, De Bruijn et al. 1989) 0.90 (recommended, Sangster 1989, 1993) 0.942 ± 0.010; 0.940 ± 0.006 (shake flask/stir-flask method by BRE; RITOX, inter-laboratory studies, Brooke et al. 1990) 0.90 (shake flask-GC, Alcorn et al. 1993) 1.21, 0.89, 0.87, 1.09 (HPLC-k. correlation, different combinations of stationary and mobile phases under isocratic conditions, Makovskaya et al. 1995) 0.92 (shake flask-dialysis tubing-HPLC/UV, both phases, Andersson & Schrader 1999) 0.88 (microemulsion electrokinetic chromatography-retention factor correlation, Jia et al. 2003) Octanol/Air Partition Coefficient, log KOA: Bioconcentration Factor, log BCF: 0.78 (fish, Lu & Metcalf 1975) 0.30 (calculated-S, Kenaga 1980) < 1.0 (fish, Freitag et al. 1982) < 1.0, 0.602, 3.01 (golden orfe, algae, activated sludge, Freitag et al. 1982) 0.602 (alga Chlorella fusca, wet wt. basis, Geyer et al. 1984) 0.845 (alga Chlorella fusca, calculated-KOW, Geyer et al. 1984) < 1.0, < 1.0, 2.70 (golden ide, algae, activated sludge, Freitag et al. 1985) 2.77 (Daphnia magna, based on elimination phase, Dauble et al. 1986) 1.87 (Daphnia magna, based on 14C and exposure water, Dauble et al. 1986) 0.70 (fish, correlated-KOW, Isnard & Lambert 1988) 0.78 (quoted, Isnard & Lambert 1988, 1989) 0.41 (zebrafish, Kalsch et al. 1991) 0.41 (zebrafish, Zok et al. 1991) 0.41; 1.04, –0.87, 0.03 (quoted exptl.; calculated values-KOW, Bintein et al. 1993) Sorption Partition Coefficient, log KOC: 3.11; 2.11 (H-montmorillonite at pH 8.35; pH 6.80, Bailey et al. 1968) 1.86 (soil average, Moreale & Van Bladel 1976) 1.41 (average of seven agricultural soils, Briggs 1981) 3.59 (colloidal organic carbon/ground water, Means et al.1982) 2.11; 2.61 (soil; more acidic soil, Pillai et al. 1982) 2.49; 2.11 (nonsterile Hagerstown soil; sterile Hagerstown soil, Pillai et al. 1982) 2.96; 2.61 (nonsterile Palouse soil; sterile Palouse soil, Pillai et al. 1982) 1.17 (soil, quoted as log KOM, Sabljic 1987) 2.12, 2.05, 2.06 (calculated values: Podzol soil, Alfisol soil, sediment, von Oepen et al. 1991) 0.596 (calculated-KOW, Kollig 1993) © 2006 by Taylor & Francis Group, LLC 3246 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals 1.08, 1.25, 0.98 (RP-HPLC-k. correlation on 3 different stationary phases, Szabo et al. 1995) 1.41 (soil, calculated-MCI 1., Sabljic et al. 1995) 2.07; 1.65 (HPLC-screening method; calculated-PCKOC fragment method, Muller & Kordel 1996) 2.70, 1.64, 2.08, 2.04, 2.29 (first generation Eurosoils ES-1, ES-2, ES-3, ES-4, ES-5, shake flask-batch equilibrium- HPLC/UV, Gawlik et al. 1998) 2.384, 1.503, 1.279, 1.437, 2.136 (second generation Eurosoils ES-1, ES-2, ES-3, ES-4, ES-5, shake flask-batch equilibrium-HPLC/UV and HPLC-k. correlation, Gawlik et al. 2000) 1.0–1.54 (5 soils, pH 2.8–7.2, batch equilibrium-sorption isotherm, Li et al. 2000) Environmental Fate Rate Constants, k, or Half-Lives, t.: Volatilization: estimated t. = 12 d from a measured Henry’s law constant of 1.2 . 10–4 atm m3 mol–1 (Yoshida et al. 1983; quoted, Howard 1989) for a model river of 1-m deep with a 1 m/s current and a 3 m/s wind (Lyman et al. 1982; quoted, Howard 1989); volatilization t.(calc) = 55 d (Torang et al. 2002). Photolysis: first-order rate constants for photosensitized reactions in water with various humic substances as sensitizers: k = 0.17 h–1 with aquatic humus from Aucilla River, k = 0.12 h–1 with Aldrich humic acid, k = 0.091 h–1 with Fluka humic acid and k = 0.11 h–1 with Contech fulvic acid in sunlight, corresponding to half-lives of 4 to 8 h (Zepp et al. 1981); photolysis t. = > 50 yr at 15°C and a pH 5–9 (Torang et al. 2002). Oxidation: rate constant k; for gas-phase second order rate constants, kOH for reaction with OH radical, kNO3 with NO3 radical and kO3 with O3 or as indicated, *data at other temperatures and/or the Arrhenius expression see reference: k = 1 . 104 M–1 s–1 for oxidation by RO2 radical at 30°C in aquatic systems with t. = 0.8 d (Howard 1972; Hendry et al. 1974; quoted, Mill 1982) k < 2 . 102 M–1 s–1 for oxidation by singlet oxygen at 25°C in aquatic systems with t. > 100 yr (Foote 1976; Mill 1979; quoted, Mill 1982) kOH = 1.20 . 10–10 cm3 molecule–1 s–1, kOH(av.) = 1.17 . 10–10 cm3 molecule–1 s–1 at 296 K (flash photolysis -RF, Rinke & Zetzsch 1984; Witte et al. 1986) kOH* = 1.10 . 10–10 cm3 molecule–1 s–1 at 298 K, measured range: 239–362 K (flash photolysis-resonance fluorescence, Witte et al. 1986) kOH(calc) = 1.54 . 10–10 cm3·molecule–1 s–1 at room temp. (Atkinson et al. 1985) kOH(obs) . 6.0 . 10–11 cm3 molecule–1 s–1; kOH(calc.) = 1.16 . 10–10 cm3 molecule–1 s–1 at room temp. (Atkinson 1985) kOH(calc) = 1.36 . 10–10 cm3 molecule–1 s–1, kOH(obs.) = 1.17 . 10–10 cm3 molecule–1 s–1, (SAR structureactivity relationship, Atkinson 1987) kOH*(exptl) = 1.18 . 10–10 cm3 molecule–1 s–1 at 296 ± 2 K, measured range: 265–455 K; and kO3 = 1.12 . 10–18 cm3 molecule–1 s–1 at 296 ± 2 K (relative rate method, Atkinson et al. 1987) kOH* = 1.11 . 10–10 cm3 molecule–1 s–1 at 298 K (recommended, Atkinson 1989) kOH(calc) = 1.385 . 10–10 cm3 molecule–1 s–1 (molecular orbital calculations, Klamt 1993) Hydrolysis: Biodegradation: completely degraded by a soil inoculum in 4 d (Alexander & Lustigman 1966; quoted, Verschueren 1983; Howard 1989); completely degraded in 20 d by bacteria in river mud (Calamari et al. 1980; quoted, Howard 1989); k = 0.23 d–1 and corresponding to a t. = 3 d in samples of White Lake water at 29°C (Subba-Rao et al. 1982); average rate of biodegradation k = 19.0 mg COD g–1 h–1 for 94.5% removal (Scow 1982); biodegradation t. = 4.5 d in unpolluted and t. < 0.5 d in polluted pond water as model environments (Lyons et al. 1984); 0.46 mM aniline solution degraded by strain Ani1 within 14 d in water (Schnell et al. 1989); average exptl. k = 0.044 h–1 compared to the group-contribution method predicted rate constants of 0.050 h–1 (nonlinear) and 0.018 h–1 (Tabak & Govind 1993); first-order k = 1.0 d–1 for batch expt. with Elbe water at 20°C (Bornick et al. 2001); field first-order degradation k ~ 1.8 d–1 for 2 different dates with water temperatures of 21.9 and 14.7°C, respectively, in Rhine river and rate constant obtained in laboratory shake flask batch tests with Rhine water averaged 1.5 d–1 at 15°C and 2.0 d–1 at 20°C (Torang et al. 2002). © 2006 by Taylor & Francis Group, LLC Nitrogen and Sulfur Compounds 3247 Biotransformation: mean bacteria transformation rate constant for all three sites of (1.1 ± 0.8) . 10–11 L·organism–1·h–1 (Paris & Wolfe 1987; quoted, Steen 1991). Bioconcentration, Uptake (k1) and Elimination (k2) Rate Constants: k1 = 0.052 ± 0.0067 h–1; k2 = 7.200 ± 1.3000 h–1 (Kalsch et al. 1991) k1 = 11.10 ± 3.2000 h–1 (zebrafish, Zok et al. 1991) Half-Lives in the Environment: Air: atmospheric lifetimes of 2.3 h in clean troposphere and 1.2 h in moderately polluted atmosphere, based on gas-phase reaction with hydroxyl radical at room temp.; atmospheric lifetimes of 15.0 d in clean troposphere and 5.0 d in moderately polluted atmosphere, based on gas-phase reaction with O3 at room temp. (Atkinson et al. 1987) t. ~ 3.3 h, based on reaction with photochemically produced hydroxyl radical (Howard 1989); atmospheric transformation lifetime was estimated to be < 1 d (Kelly et al. 1994). Surface water: estimated t. = 2.3 d in Rhine river in case of a first order reduction process (Zoeteman et al. 1980; quoted, Howard 1989); estimated t. = 0.3–3.0 d in river waters (Zoeteman et al. 1980); t. = 4 to 8 h in May sunlight with both commercial humic acids and aquatic humus as photosensitizers near-surface water and t. ~ 1 wk in distilled water (Zepp et al. 1981); t. = 6 d in eutropic pond and t. = 21 d in an oligotrophic lake (Subba-Rao et al. 1982; quoted, Howard 1989); biodegradation t. = 4.5 d in unpolluted and t. < 0.5 d in polluted pond water as model environments (Lyons et al. 1984); t. = 4–33 d at 15°C (Ingerslev & Nyholm 2000); t. ~ 9 h in the Rhine river at 15 and 22°C (Torang et al. 2002). Ground water: estimated t. ~ 30–300 d (Zoeteman et al. 1980). Sediment: Soil: Biota: TABLE 16.1.3.1.1 Reported vapor pressures of aniline at various temperatures and the coefficients for the vapor pressure equations log P = A – B/(T/K) (1) ln P = A – B/(T/K) (1a) log P = A – B/(C + t/°C) (2) ln P = A – B/(C + t/°C) (2a) log P = A – B/(C + T/K) (3) log P = A – B/(T/K) – C·log (T/K) (4) Stull 1947 Dreisbach & Shrader 1949 McDonald et al. 1959 Hatton et al. 1962 summary of literature data ebulliometry ebulliometry calc-thermodynamic properties t/°C P/Pa t/°C P/Pa t/°C P/Pa t/°C P/Pa 34.8 133.3 112.92 10351 102.59 6806 31.55 133.3 57.9 666.6 125.16 17039 117.22 12295 41.82 666.6 69.4 1333 153.2 42103 137.5 25439 52.59 1333 82.0 2666 168.21 67701 160.08 51913 68.62 2666 96.7 5333 183.93 101325 182.4 97103 82.11 5333 106.0 7999 184.24 101912 97.02 7999 119.9 13332 bp/°C 183.93 185.15 104589 119.41 13332 140.1 26664 138.90 26664 161.9 53329 mp/°C –6.02 161.05 53329 184.4 101325 184.40 101325 eq. 2 P/mmHg mp/°C –6.2 A 7.25375 B 1684.35 C 201.175 © 2006 by Taylor & Francis Group, LLC 3248 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals FIGURE 16.1.3.1.1 Logarithm of vapor pressure versus reciprocal temperature for aniline. Aniline: vapor pressure vs. 1/T 0.0 1.0 2.0 3.0 4.0 5.0 6.0 7.0 8.0 0.002 0.0024 0.0028 0.0032 0.0036 0.004 1/(T/K) P( gol S ) aP/ Kahlbaum 1898 Dreisbach & Shrader 1949 McDonald et al. 1959 Hatton et al. 1962 Stull 1947 b.p. = 184.17 °C m.p. = -6.02 °C © 2006 by Taylor & Francis Group, LLC Nitrogen and Sulfur Compounds 3249 16.1.3.2 2-Chloroaniline Common Name: 2-Chloroaniline Synonym: 1-amino-2-chlorobenzene, o-aminochlorobenzene, o-chloroaniline, 2-chlorophenylamine Chemical Name: 1-amino-2-chlorobenzene, o-chloroaniline, 2-chloroaniline CAS Registry No: 95-51-2 Molecular Formula: C6H4NH2Cl Molecular Weight: 127.572 Melting Point (°C): –1.94 (.-2-chloroaniline, Dreisbach 1955; Weast 1872–83, Riddick et al. 1986) –14.0 (.-2-chloroaninline, Weast 1982–83; Verschueren 1983; Howard 1989) –1.9 (Lide 2003) Boiling Point (°C): 208.8 (Kahlbaum 1898; Stull 1947; Dreisbach 1955; Weast 1982–83; Lide 2003) Density (g/cm3 at 20°C): 1.21266, 1.20787 (20°C, 25°C, Dreisbach 1955) 1.21251, 1.20775 (20°C, 25°C, Riddick et al. 1986) Molar Volume (cm3/mol): 105.2 (20°C, Stephenson & Malanowski 1987) 131.1 (calculated-Le Bas method at normal boiling point) Dissociation Constant, pKa: 2.661 (Perrin 1972; quoted, Howard 1989) 2.650 (Weast 1982–83) 2.640 (protonated cation + 1, Dean 1985) 2.640 (Riddick et al. 1986) Enthalpy of Vaporization, .HV (kJ/mol): 57.5 ± 5 (25°C, Piacente et al. 1985) 56.756, 44.35 (25°C, bp, Riddick et al. 1986) Enthalpy of Fusion, .Hfus (kJ/mol): 11.88 (Riddick et al. 1986) Entropy of Fusion, .Sfus (J/mol K): Fugacity Ratio at 25°C (assuming .Sfus = 56 J/mol K), F: 1.0 Water Solubility (g/m3 or mg/L at 25°C or as indicated): 8760 (Dreisbach 1955) 3765 (20°C, shake flask-GC, Chiou 1981; Chiou & Schmedding 1981; Chiou et al. 1982) 3763 (calculated-KOW, Muller & Klein 1992) 4740 (calculated-group contribution method, Kuhne et al. 1995) Vapor Pressure (Pa at 25°C or as indicated and reported temperature dependence equations. Additional data at other temperatures designated * are compiled at the end of this section): 40.31* (extrapolated-regression of tabulated data, measured range 64.4–208.8°C, Kahlbaum 1898) 37.77* (extrapolated-regression of tabulated data, temp range 46.3–208.8°C, Stull 1947) log (P/mmHg) = 7.63311 – 2085.5/(230 + t/°C) (Antoine eq., Dreisbach & Martin 1949) 7605* (124.48°C, ebulliometry, measured range 124.48–208.84°C, Dreisbach & Shrader 1949) 33.77 (calculated by formula, Dreisbach 1955; selected, Riddick et al. 1986) log (P/mmHg) = 7.19240 – 1762.74/(200.0 + t/°C); temp range 110–330°C (Antoine eq. for liquid state, Dreisbach 1955) log (P/mmHg) = [–0.2185 . 12441.0/(T/K)] + 8.56946; temp range 46.3–208.8°C (Antoine eq., Weast 1972–73) 33.88 (calculated-Antoine eq., Dean 1985, 1992) NH2 Cl © 2006 by Taylor & Francis Group, LLC 3250 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals log (P/mmHg) = 7.56265 – 1998.6/(220.0 + t/°C), temp range 20–108°C (Antoine eq., Dean 1985, 1992) log (P/mmHg) = 7.19240 – 1762.74/(200.0 + t/°C), temp range: 108–300°C (Antoine eq., Dean 1985, 1992) 35.30* (torsion-weighing effusion, Piacente et al. 1985) log (P/kPa) = (8.63 ± 0.16) – (3006 ± 56)/(T/K); temp range: 287–336 K (Antoine eq., combined torsionweighing effusion, Piacente et al. 1985) log (P/kPa) = 6.75801 – 2085.50/(230.0 + t/°C); temp range not specified (Antoine eq., Riddick et al. 1986) 18.97 (extrapolated-Antoine eq., Stephenson & Malanowski 1987) log (PL/kPa) = 5.84227 – 1432.2/(–108.81 + T/K); temp range 397–482 K (Antoine eq., Stephenson & Malanowski 1987) log (P/mmHg) = 90.6491 – 6.041 . 103/(T/K) – 31.118·log (T/K) + 1.1564 . 10–2·(T/K) + 4.8388 . 10–13·(T/K)2; temp range 271–722 K (vapor pressure eq., Yaws 1994) Henry’s Law Constant (Pa·m3/mol at 25°C): 0.760 (calculated-P/C, Howard 1989) 0.425 (calculated-P/C, Meylan & Howard 1991) 0.143 (estimated-bond contribution, Meylan & Howard 1991) Octanol/Water Partition Coefficient, log KOW: 1.81 (shake flask, Fujita et al. 1964) 1.90 (Leo et al. 1971; Hansch & Leo 1979; Hansch & Leo 1985) 1.92 (exptl., Leo et al. 1971; McCall 1975; Rekker 1977) 1.92 (HPLC-k. correlation, Carlson et al. 1975) 1.63 (calculated-. const., Norrington et al. 1975) 1.61, 1.73 (calculated-. const., calculated-f const., Rekker 1977) 1.90, 1.92 (shake flask, Hansch & Leo 1979) 1.74 (HPLC-k. correlation, Konemann et al. 1979) 1.74 (calculated-f const., Rekker & De Kort 1979) 1.91 ± 0.01 (HPLC-k., Hammers et al. 1982) 1.99 (HPLC-k. correlated, Hammers et al. 1982) 1.926 ± 0.021 (slow-stirring-GC, De Bruijn et al. 1989) 1.88 (recommended, Sangster 1993) 1.93 ± 0.14, 1.55 ± 0.51 (solvent generated liquid-liquid chromatography SGLLC-correlation, RP-HPLC-k. correlation, Cichna et al. 1995) 1.90 (recommended, Hansch et al. 1995) Octanol/Air Partition Coefficient, log KOA: Bioconcentration Factor, log BCF: < 2.0 (Kawasaki 1980) 1.30 (estimated, Canton et al. 1985) 1.18 (zebrafish, Zok et al. 1991) 0.301–0.57 (carp, Tsuda et al. 1993) 1.18; 1.56, 0.73, 0.94 (quoted; calculated values-KOW, Bintein et al. 1993) Sorption Partition Coefficient, log KOC: Environmental Fate Rate Constants, k, or Half-Lives, t.: Volatilization: using Henry’s law constant, t. ~ 5.6 d was estimated for a model river of 1-m deep (Lyman et al. 1982; quoted, Howard 1989); estimated t. = 64 d from a representative environmental pond (stagnant) (USEPA 1987; quoted, Howard 1989). Photolysis: Oxidation: rate constant of 5.1 . 10–12 cm3/molecule·s for the reaction with hydroxyl radical in a typical ambient atmosphere at 25°C with t. ~ 2 d (GEMS 1987; quoted, Howard 1989). Hydrolysis: Biodegradation: average biodegradation rate of 25 mg COD g–1 h–1 for 95.6% removal (Scow 1982). © 2006 by Taylor & Francis Group, LLC Nitrogen and Sulfur Compounds 3251 Biotransformation: Bioconcentration, Uptake (k1) and Elimination (k2) Rate Constants: k1 = 7.10 h–1 (zebrafish, Zok et al. 1991) k2 = 0.19 h–1 (carp, Tsuda et al. 1993) Half-Lives in the Environment: Air: estimated atmospheric t. = 2 d, based on the reaction with sunlight-produced hydroxyl radical (GEMS 1987; quoted, Howard 1989). Surface water: Groundwater: Sediment: Soil: Biota: t. = 3.6 h in carp with excretion rate constant k = 0.19 h–1 (Tsuda et al. 1993). TABLE 16.1.3.2.1 Reported vapor pressures of 2-chloroaniline at various temperatures and the coefficients for the vapor pressure equations log P = A – B/(T/K) (1) ln P = A – B/(T/K) (1a) log P = A – B/(C + t/°C) (2) ln P = A – B/(C + t/°C) (2a) log P = A – B/(C + T/K) (3) log P = A – B/(T/K) – C·log (T/K) (4) Kahlbaum 1898 Stull 1947 Piacente et al. 1985 Piacente et al. 1985 static method summary of literature data torsion-weighing effusion torsion-weighing effusion t/°C P/Pa t/°C P/Pa t/°C P/Pa t/°C P/Pa run 62 average average 64.4 400 46.3 133.3 14 18 23 36 72.3 666.6 72.3 666.6 20 32 24 41 84.8 1333 84.8 1333 27 45 28 50 92.9 2000 99.2 2666 32 72 30 66 99.2 2666 115.6 5333 34 96 31 62 104.2 3333 125.7 7999 34.5 86 32 83 108.4 4000 139.5 13332 38 117 34 87 112.0 4666 160.0 26664 43 200 35 90 115.2 6333 183.7 53329 34 203 38 112 118.1 6000 208.8 101325 48.5 251 41 167 120.7 6666 52.5 347 43 190 131.4 9999 mp/°C - 54 362 45 200 139.5 13332 63 505 47 218 160.0 26664 49 269 173.6 39997 Dreisbach & Shrader 1949 51 275 183.7 53329 ebulliometry 51 309 192.0 66661 t/°C P/Pa 55 343 199.4 79993 56 354 208.8 101325 124.48 7605 57 398 131.54 10114 145.3 16500 overall vapor pressure eq. 154.55 42066 eq. 1 P/kPa 192.71 67661 A 8.63 ± 0.16 208.84 101325 B 3006 ± 56 .HV/(kJ mol–1) = 57.5 ± 5 at 25°C © 2006 by Taylor & Francis Group, LLC 3252 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals FIGURE 16.1.3.2.1 Logarithm of vapor pressure versus reciprocal temperature for 2-chloroaniline. 2-Chloraniline: vapor pressure vs. 1/T 0.0 1.0 2.0 3.0 4.0 5.0 6.0 7.0 8.0 0.0018 0.0022 0.0026 0.003 0.0034 0.0038 1/(T/K) P( gol S ) aP/ Kahlbaum 1898 Dreisbach & Shrader 1949 Piacente et al. 1985 Stull 1947 b.p. = 208.8 °C m.p. = -1.9 °C © 2006 by Taylor & Francis Group, LLC Nitrogen and Sulfur Compounds 3253 16.1.3.3 3-Chloroaniline Common Name: 3-Chloroaniline Synonym: 1-amino-3-chlorobenzene, m-chloroaniline, 3-chlorophenylamine Chemical Name: 1-amino-3-chlorobenzene, m-chloroaniline, 3-chloroaniline CAS Registry No: 108-42-9 Molecular Formula: C6H4NH2Cl Molecular Weight: 127.572 Melting Point (°C): –10.28 (Lide 2003) Boiling Point (°C): 230.5 (Lide 2003) Density (g/cm3 at 20°C): 1.21606 (20°C, Weast 1982–83) 1.2150 (22°C, Dean 1985; Budavari 1989) Molar Volume (cm3/mol): 105.0 (22°C, calculated-density, Stephenson & Malanowski 1987) 131.1 (calculated-Le Bas method at normal boiling point) Dissociation Constant, pKa: 3.52 (Perrin 1972) 3.50 (McLeese et al. 1979) 3.46 (Weast 1982–83) 3.52 (protonated cation + 1, Dean 1985) Enthalpy of Vaporization, .HV (kJ/mol): 61.04, 46.016 (25°C, bp, Dreisbach 1955) 60.9 ± 5 (25°C, Piacente et al. 1985) Enthalpy of Fusion, .Hfus (kJ/mol): 10.25 (Dreisbach 1955) Entropy of Fusion, .Sfus (J/mol K): Fugacity Ratio at 25°C (assuming .Sfus = 56 J/mol K), F: 1.0 Water Solubility (g/m3 or mg/L at 25°C): 5442 (20°C, shake flask-GC, Chiou 1981; Chiou & Schmedding 1981; Chiou et al. 1982) 5447 (calculated-KOW, Muller & Klein 1992) 4740 (calculated-group contribution method, Kuhne et al. 1995) Vapor Pressure (Pa at 25°C and reported temperature dependence equations. Additional data at other temperatures designated * are compiled at the end of this section): 13.14* (extrapolated-regression of tabulated data, measured range 81.7–228.5°C, Kahlbaum 1898) 11.94* (extrapolated-regression of tabulated data, temp range 63.5–228.5°C, Stull 1947) 11.17 (calculated by formula, Dreisbach 1955) log (P/mmHg) = 7.23603 – 1857.75/(196.64 + t/°C); temp range 125–350°C (Antoine eq. for liquid state, Dreisbach 1955) log (P/mmHg) = [–0.2185 . 133854.6/(T/K)] + 8.761546; temp range 63.5–228.5°C (Antoine eq., Weast 1972–73) 11.06 (calculated-Antoine eq., Dean 1985, 1992) log (P/mmHg) = 7.59939 – 2073.75/(215.0 + t/°C), temp range 15–125°C (Antoine eq., Dean 1985, 1992) log (P/mmHg) = 7.23603 – 1857.75/(196.64 + t/°C), temp range 125–310°C (Antoine eq., Dean 1985, 1992) 15.60* (torsion-weighing effusion, Piacente et al. 1985) NH2 Cl © 2006 by Taylor & Francis Group, LLC 3254 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals log (P/kPa) = (8.86 ± 0.10) – (3180 ± 40)/(T/K); temp range ~290–345 K (Antoine eq., combined torsionweighing effusion, Piacente et al. 1985) 9.530 (extrapolated from Antoine eq., Stephenson & Malanowski 1987) log (PL/kPa) = 6.36093 – 1857.75/(–76.51 + T/K); temp range 398–573 K (Antoine eq., Stephenson & Malanowski 1987) log (P/mmHg) = 65.6033 – 5.3779 . 103/(T/K) –20.518·log (T/K) + 6.7861 . 10–3·(T/K) + 2.1167 . 10–13·(T/K)2; temp range 263–751 K (vapor pressure eq., Yaws 1994) Henry’s Law Constant (Pa·m3/mol at 25°C): 0.223 (calculated-P/C) 0.102 (gas stripping-GC, Altschuh et al. 1999) Octanol/Water Partition Coefficient, log KOW: 1.88 (shake flask-UV, Fujita et al. 1964) 1.88 (Ichikawa et al. 1969) 1.88 (Leo et al. 1971; Hansch & Leo 1979) 1.90 (exptl., Leo et al. 1971; Rekker 1977) 1.98 (calculated-. const., Norrington et al. 1975) 1.73, 1.75; 1.61 (calculated-f const., calculated-. const., Rekker 1977) 1.90, 1.88 (shake flask, Hansch & Leo 1979) 1.57 (HPLC-k. correlation, Konemann et al. 1979) 1.89 ± 0.01 (HPLC-k. correlation, Hammers et al. 1982) 2.00 (HPLC-k. correlation, Hammers et al. 1982) 1.910 ± 0.013 (slow-stirring-GC, De Bruijn et al. 1989) 1.88 (recommended, Sangster 1993) 1.91 ± 0.14, 1.52 ± 0.51 (solvent generated liquid-liquid chromatography SGLLC-correlation, RP-HPLC-k. correlation, Cichna et al. 1995) 1.88 (recommended, Hansch et al. 1995) Octanol/Air Partition Coefficient, log KOA: Bioconcentration Factor, log BCF: 1.06 (zebrafish, Zok et al. 1991) –0.097 to 0.342 (average for carp, Tsuda et al. 1993) 1.06; 1.55, 0.70, 0.92 (quoted; calculated values, Bintein et al. 1993) Sorption Partition Coefficient, log KOC: Environmental Fate Rate Constants, k, or Half-Lives, t.: Volatilization: Photolysis: direct aqueous photolysis rate constant k = 0.393 ± 0.006 min–1 with a calculated t. = 1.76 min (Stegeman et al. 1993). Oxidation: Hydrolysis: direct photohydrolysis rate constant k = 0.393 ± 0.006 min–1 with a calculated t. = 1.76 min (Stegeman et al. 1993). Biodegradation: average biodegradation rate of 6.2 mg COD g–1 h–1 for 97.2% removal (Scow 1982). Biotransformation: mean bacteria transformation rate constant for all three sites of (2.2 ± 1.7) . 10–12 L·organism–1·h–1 (Paris & Wolfe 1987; quoted, Steen 1991). Bioconcentration, Uptake (k1) and Elimination (k2) Rate Constants: k1 = 19.1 h–1 (zebrafish, Zok et al. 1991) k2 = 0.21 h–1 (carp, Tsuda et al. 1993) Half-Lives in the Environment: Biota: t. = 3.3 h in carp with excretion rate k = 0.21 h–1 (Tsuda et al. 1993). © 2006 by Taylor & Francis Group, LLC Nitrogen and Sulfur Compounds 3255 TABLE 16.1.3.3.1 Reported vapor pressures of 3-chloroaniline at various temperatures and the coefficients for the vapor pressure equations log P = A – B/(T/K) (1) ln P = A – B/(T/K) (1a) log P = A – B/(C + t/°C) (2) ln P = A – B/(C + t/°C) (2a) log P = A – B/(C + T/K) (3) log P = A – B/(T/K) – C·log (T/K) (4) Kahlbaum 1898 Stull 1947 Piacente et al. 1985 static method summary of literature data torsion-weighing effusion t/°C P/Pa t/°C P/Pa t/°C P/Pa t/°C P/Pa run 63 average run 64 average 81.7 400 63.5 133.3 19 8 31 19 89.8 666.6 89.8 666.6 29 17 39 41 102 1333 102 1333 36.5 33 42 50 110.4 2000 116.7 2666 43 49 44 52 116.8 2666 133.6 5333 50 89 45 56 122.0 3333 144.1 7999 57.5 145 46 66 126.2 4000 158 13332 65 250 47 70 129.8 4666 179.5 26664 73 376 49 89 133.2 6333 203.5 53329 50 85 136.2 6000 228.5 101325 51 95 138.8 6666 52 105 149.9 9999 mp/°C –10.4 53 102 158.0 13332 55 126 179.5 26664 57 146 193.2 53329 59 151 203.5 66661 60.5 170 211.9 79993 62 190 228.5 101325 63 204 65 240 69 296 overall vapor pressure eq. eq. 1 P/kPa A 8.86 ± 0.10 B 3180 ± 40 .HV/(kJ mol–1) = 60.9 ± 5 at 25°C © 2006 by Taylor & Francis Group, LLC 3256 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals FIGURE 16.1.3.3.1 Logarithm of vapor pressure versus reciprocal temperature for 3-chloroaniline. 3-Chloraniline: vapor pressure vs. 1/T -2.0 -1.0 0.0 1.0 2.0 3.0 4.0 5.0 6.0 0.0018 0.0022 0.0026 0.003 0.0034 0.0038 0.0042 1/(T/K) P ( gol S ) aP/ Kahlbaum 1898 Piacente et al. 1985 Stull 1947 b.p. = 230.5 °C m.p. = -10.28 °C © 2006 by Taylor & Francis Group, LLC Nitrogen and Sulfur Compounds 3257 16.1.3.4 4-Chloroaniline Common Name: 4-Chloroaniline Synonym: 1-amino-4-chlorobenzene, p-chloroaniline, 4-chlorophenylamine Chemical Name: 1-amino-4-chlorobenzene, p-chloroaniline, 4-chloroaniline CAS Registry No: 106-47-8 Molecular Formula: NH2C6H4Cl Molecular Weight: 127.572 Melting Point (°C): 70.5 (Lide 2003) Boiling Point (°C): 232.0 (Weast 1982–83; Verschueren 1983; Howard 1989) Density (g/cm3 at 20°C): 1.429 (19°C, Weast 1982–83) Molar Volume (cm3/mol): 131.1 (calculated-Le Bas method at normal boiling point) Dissociation Constant, pKa: 3.98 (Perrin 1972; Freitag et al. 1984; quoted, Howard 1989) 4.20 (McLeese et al. 1979) 4.15 (Weast 1982–83) 3.99 (protonated + 1, Dean 1985) Enthalpy of Vaporization, .HV (kJ/mol): 79 ± 5 (25°C, Piacente et al. 1985) Enthalpy of Fusion, .Hfus (kJ/mol): 15.69 (Tsonopoulos & Prausnitz 1971) Entropy of Fusion, .Sfus (J/mol K): 57.74 (Tsonopoulos & Prausnitz 1971) Fugacity Ratio at 25°C (assuming .Sfus = 56 J/mol K), F: 0.358 (mp at 70.5°C) Water Solubility (g/m3 or mg/L at 25°C): 3000 (Philpot et al. 1940) 3900 (Kilzer et al. 1979) 2620 (Schmidt-Bleek et al. 1982; Rott et al. 1982) 2487 (calculated-group contribution method, Kuhne et al. 1995) Vapor Pressure (Pa at 25°C and reported temperature dependence equations. Additional data at other temperatures designated * are compiled at the end of this section): 1.707* (20°C, Knkudsen effusion, measured range 10–30°C, Swan & Mack 1925) 15.19* (extrapolated-regression of tabulated data, temp range 59.3–230.5°C, Stull 1947) log (P/mmHg) = [–0.2185 . 12832.8/(T/K)] + 8.461034; temp range 59.3–230.5°C (Antoine eq., Weast 1972–73) 3.173 (effusion method, DePablo 1976) 3.33 (extrapolated, Verschueren 1977) 2.00, 6.67 (20°C, 30°C, quoted, Verschueren 1983) 0.224 (extrapolated-Antoine eq., Boublik et al. 1984) log (P/kPa) = 3.55438 – 521.556/(47.392 + t/°C); temp range 90–150°C (Antoine eq. from reported exptl. data, Boublik et al. 1984) 1.636* (torsion-weighing effusion, Piacente et al. 1985) NH2 Cl © 2006 by Taylor & Francis Group, LLC 3258 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals log (P/kPa) = (11.20 ± 0.20) – (4170 ± 60)/(T/K); temp range ~298–360 K (Antoine eq., combined torsionweighing effusion, Piacente et al. 1985) 3.66 (calculated-Antoine eq.-I, Stephenson & Malanowski 1987) log (PS/kPa) = 13.448 – 4736/(T/K), temp range 283–303 K (Antoine eq.-I, Stephenson & Malanowski 1987) log (PL/kPa) = 7.3489 – 2729/(T/K), temp range 363–505 K (Antoine eq.-II, Stephenson & Malanowski 1987) 3.33, 32.0 (quoted, calculated-solvatochromic parameters, Banerjee et al. 1990) log (P/mmHg) = –15.3259 – 2.8592 . 103/(T/K) + 11.527·log (T/K) – 1.8071 . 10–2·(T/K) + 7.2359 . 10–6·(T/K)2; temp range 343–754 K (vapor pressure eq., Yaws 1994) Henry’s Law Constant (Pa m3/mol at 25°C): 1.0840 (calculated-P/C, Howard 1989) 0.0395 (calculated-P/C, Meylan & Howard 1991) 0.1430 (estimated-bond contribution, Meylan & Howard 1991) Octanol/Water Partition Coefficient, log KOW: 1.84 (Ichikawa et al. 1969) 1.83 (quoted exptl., Leo et al. 1969, 1971; Hansch & Leo 1985) 1.83 (HPLC-k. correlation; Carlson et al. 1975) 1.83 (shake flask, Hansch & Leo 1979) 1.57 (HPLC-k. correlation, Konemann et al. 1979) 1.83, 20.2 (HPLC-k. correlation, Hammers et al. 1982) 1.64 (inter-laboratory studies, HPLC-RT correlation average, Eadsforth & Moser 1983) 1.88 ± 0.02 (HPLC-RV correlation-ALPM; Garst & Wilson 1984) 2.78 (shake flask, OECD 1981 Guidelines, Geyer et al. 1984) 1.83 (shake flask, Log P Database, Hansch & Leo 1987) 1.83 (RP-HPLC-k. correlation, Minick et al. 1988) 1.88 ± 0.014 (shake flask/slow-stirring-GC, De Brujin et al. 1989) 1.83 (shake flask, Leahy et al. 1989) 1.80, 1.82 (shake flask, HPLC-RT correlation, Wang et al. 1989) 2.01 (centrifugal partition chromatography CPC-RV correlation, El Tayar et al. 1991) 1.83 (recommended, Sangster 1993) 1.83 (pH 7.4, Hansch et al. 1995) Octanol/Air Partition Coefficient, log KOA: Bioconcentration Factor, log BCF: < 1.30 (golden orfe for 3-d exposure, Korte et al. 1978) 3.08 (green algae for 24-h exposure of dry wt. basis, Korte et al. 1978) 2.42 (green algae for 24-h exposure of wet wt. basis, Korte et al. 1978) < 1.0, 2.41, 3.11 (golden orfe, algae, activated sludge, Freitag et al. 1982) 2.42 (alga Chlorella fusca, wet wt. basis, Geyer et al. 1984) 2.06 (alga Chlorella fusca, calculated-KOW, Geyer et al. 1984) 1.11, 2.42, 2.45 (golden ide, algae, activated sludge, Freitag et al. 1985) 0.91 (zebrafish, Zok et al. 1991) –0.097–0.23 (carp, Tsuda et al. 1993) 0.91; 1.52, 0.63, 0.88 (quoted; calculated values, Bintein et al. 1993) 2.58 (algae Chlorella fusca, wet wt basis, Wang et al. 1996) Sorption Partition Coefficient, log KOC: 2.36–2.67 (five Belgium soils, Van Bladel & Moreale 1977) 1.98–3.18 (five German soils, Rott et al. 1982) 3.74 (colloidal org. matter in ground water, Means 1983) 1.86 (calculated-MCI ., Sabljic 1987) 2.08 (RP-HPLC-k. correlation, cyanopropyl column, Hodson & Williams 1988) 1.96, 1.86 (soil, quoted exptl., calculated-MCI . and fragment contribution, Meylan et al. 1992) © 2006 by Taylor & Francis Group, LLC Nitrogen and Sulfur Compounds 3259 1.61 (calculated-KOW, Kollig 1993) 1.96 (soil, calculated-MCI 1., Sabljic et al. 1995) 2.28; 1.86 (HPLC-screening method; calculated-PCKOC fragment method, Muller & Kordel 1996) 3.086, 2.21, 2.48, 2.374, 2.973 (first generation Eurosoils ES-1, ES-2, ES-3, ES-4, ES-5, shake flask/batch equilibrium-HPLC/UV, Gawlik et al. 1998) 2.801, 2.326, 2.145, 2.420 (second generation Eurosoils ES-1, ES-3, ES-4, ES-5, shake flask/batch equilibrium- HPLC/UV and HPLC-k. correlation, Gawlik et al. 2000) Environmental Fate Rate Constants, k, or Half-Lives, t.: Volatilization: estimated t. = 6.4 h from using Henry’s law constant for a model river of 1-m deep with 1 m/s current and 3 m/s wind (Lyman et al. 1982; quoted, Howard 1989); t. = 3 d in an experimental pond with spiked 4-chloroaniline (Schauerte et al. 1982; quoted, Howard 1989). Photolysis: Oxidation: rate constant k; for gas-phase second order rate constants, kOH for reaction with OH radical, kNO3 with NO3 radical and kO3 with O3 or as indicated, *data at other temperatures see reference: kOH = (8.3 ± 0.42) . 10–11 cm3 molecule–1 s–1 at 295 K (flash photolysis-resonance fluorescence, Wahner & Zetzsch 1983) kOH(obs.) = 83 . 10–12 cm3 molecule–1 s–1; kOH(calc) = 34.7 . 10–12 cm3 molecule–1 s–1 at room temp. in air (Atkinson 1985; Atkinson et al. 1985) kOH(calc) = 54 . 10–12 cm3 molecule–1 s–1; kOH(obs.) = 83 . 10–12 cm3 molecule–1 s–1 at room temp. (SAR, Atkinson 1987) kOH = (83 to ~44) . 10–12 cm3 molecule–1 s–1 at 295–296 K (Atkinson 1989) Hydrolysis: Biodegradation: Biotransformation: Bioconcentration, Uptake (k1) and Elimination (k2) Rate Constants: k1 = 42.9 h–1 (zebrafish, Zok et al. 1991) k2 = 0.16 h–1 (carp, Tsuda et al. 1993) k1 = 17.74 h, k2 = 0.0465 h (algae Chlorella fusca, Wang et al. 1996) Half-Lives in the Environment: Air: t. = 4.6 h, based on estimated reaction rate with photochemically produced hydroxyl radical of 5 . 105 radicals/cm3 in atmosphere (Wahner & Zetzsch 1983; quoted, Howard 1989). Surface water: estimated t. = 0.3–3.0 d in river waters in case of a first order reduction process (Zoeteman et al. 1980); 72.1 mg/L total organic carbon (TOC) degraded to 92% TOC after 5 h illumination with a 250 watt tungsten lamp by photo-Fenton reaction in distilled water (Ruppert et al. 1993). Groundwater: estimated t. = 30–300 d in Rhine River (Zoeteman et al. 1980). Sediment: Soil: Biota: t. = 4.3 h in carp with excretion rate k = 0.16 h–1 (Tsuda et al. 1993). © 2006 by Taylor & Francis Group, LLC 3260 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals TABLE 16.1.3.4.1 Reported vapor pressures of 4-chloroaniline at various temperatures and the coefficients for the vapor pressure equations log P = A – B/(T/K) (1) ln P = A – B/(T/K) (1a) log P = A – B/(C + t/°C) (2) ln P = A – B/(C + t/°C) (2a) log P = A – B/(C + T/K) (3) log P = A – B/(T/K) – C·log (T/K) (4) Swan & Mack 1925 Stull 1947 Piacente et al. 1985 Knudsen effusion summary of literature data torsion-weighing effusion t/°C P/Pa t/°C P/Pa t/°C P/Pa t/°C P/Pa Run 58 average Run 66 average 10 0.513 59.3 133.3 26 3.0 52 56 20 1.707 87.9 666.6 31 6.0 56.5 75 30 6.493 102.1 1333 34 8.0 61 128 117.8 2666 39 13 63 136 135.0 5333 40 17 65 152 145.8 7999 43 20 68 238 eq. 4 P/mmHg 159.9 13332 48 31 71 275 A 415.007 182.3 26664 49.5 35 72 316 B 22322 206.6 53329 53 48 C 138.475 230.5 101325 59 87 60.5 100 overall vapor pressure eq. .HV/(kJ mol–1) = 90.37 mp/°C 70.5 63.5 127 eq. 1 P/kPa at 20°C 67 170 A 11.20 ± 0.20 69.5 224 B 4170 ± 60 82.5 549 88.5 832 .HV/(kJ mol–1) = 70.9 ± 5 at 25°C FIGURE 16.1.3.4.1 Logarithm of vapor pressure versus reciprocal temperature for 4-chloroaniline. 4-Chloraniline: vapor pressure vs. 1/T -1.0 0.0 1.0 2.0 3.0 4.0 5.0 6.0 7.0 0.0018 0.0022 0.0026 0.003 0.0034 0.0038 1/(T/K) P ( gol S ) aP / Swan & Mack 1925 Piacente et al. 1985 Stull 1947 b.p. = 232 °C m.p. = -70.5 °C © 2006 by Taylor & Francis Group, LLC Nitrogen and Sulfur Compounds 3261 16.1.3.5 3,4-Dichloroaniline Common Name: 3,4-Dichloroaniline Synonym: Chemical Name: 3,4-dichloroaniline CAS Registry No: 95-76-1 Molecular Formula: C6H5Cl2N, C6H3NH2Cl2 Molecular Weight: 162.017 Melting Point (°C): 72.0 (Weast 1982–83; Lide 2003) Boiling Point (°C): 272.0 (Weast 1982–83; Lide 2003) Density (g/cm3 at 20°C): Molar Volume (cm3/mol): 111.7 (calculated-density, Jaworska & Schultz 1993) 152.0 (calculated-Le Bas method at normal boiling point) Dissociation Constant, pKa: 2.968, 3.0 (Perrin 1972) 2.00 (estimated, Wolff & Crossland 1985) Enthalpy of Fusion, .Hfus (kJ/mol): Entropy of Fusion, .Sfus (J/mol K): Fugacity Ratio at 25°C (assuming .Sfus = 56 J/mol K), F: 0.346 (mp at 72°C) Water Solubility (g/m3 or mg/L at 25°C): 92.03 (20°C, Wolff & Crossland 1985) 93.2; 740 (quoted exptl.; calculated-group contribution method, Kuhne et al. 1995) Vapor Pressure (Pa at 25°C or as indicated and reported temperature dependence equations): 1.30 (20°C, Wolff & Crossland 1985) 2.27 (extrapolated-Antoine eq., Stephenson & Malanowski 1987) log (PL/kPa) = 7.6189 – 3060.03/(T/K); temp range 420–545 K (Antoine eq., Stephenson & Malanowski 1987) log (P/mmHg) = –15.2685 – 3.3857 . 103/(T/K) + 11.926·log (T/K) –1.9227 . 10–2·(T/K) + 7.4179 . 10–6·(T/K)2; temp range 345–800 K (vapor pressure eq., Yaws 1994) Henry’s Law Constant (Pa·m3/mol at 25°C): 2.289 (calculated-P/C) Octanol/Water Partition Coefficient, log KOW: 2.69 (unpublished result, Leo et al. 1971, Hansch & Leo 1979) 2.12 (HPLC-k. correlation, Konemann et al. 1979) 2.78 (20°C, shake flask-UV, Briggs 1981) 2.69, 2.67 (HPLC-k. correlation, Hammers et al. 1982) 2.62 (inter-laboratory studies, shake flask average, Eadsforth & Moser 1983) 2.30 (inter-laboratory studies, HPLC-RT correlation average, Eadsforth & Moser 1983) 2.14, 2.63 (HPLC-k. correlation, Eadsforth 1986) 2.69 (shake flask, Log P Database, Hansch & Leo 1987) 2.68 (recommended, Sangster 1993) 2.69 (recommended, Hansch et al. 1995) 2.69 (LOGPSTAR or CLOGP data, Sabljic et al. 1995) NH2 Cl Cl © 2006 by Taylor & Francis Group, LLC 3262 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals Octanol/Air Partition Coefficient, log KOA: Bioconcentration Factor, log BCF: 1.48 (zebrafish, Zok et al. 1991) 1.48; 2.02, 1.88, 1.75 (fish: quoted; calculated values-KOW, Bintein et al. 1993) Sorption Partition Coefficient, log KOC: 2.29 (20°C, sorption isotherm-GC, converted from KOM multiplied by 1.724, Briggs 1981) 1.40 (calculated-KOW, wet sediment, Wolff & Crossland 1985) 2.29 (Sabljic 1987) 2.05 (soil, quoted, Sabljic 1987) 2.29, 2.08 (soil, quoted, calculated-MCI . and fragment contribution, Meylan et al. 1992) 2.29 (calculated-MCI 1., Sabljic et al. 1995) 2.26, 2.39 (RP-HPLC-k. correlation including MCI related to non-dispersive intermolecular interactions, hydrogen-bonding indicator variable, Hong et al. 1996) Environmental Fate Rate Constants, k, or Half-Lives, t.: Volatilization: first order rate constant k(calc) = 5.0 . 10–3 d–1 (Wolff & Crossland 1985). Photolysis: phototransformation rate constant k = 0.12 to 0.20 d–1 (Wolff & Crossland 1985). Oxidation: Hydrolysis: not expected to occur (Wolff & Crossland 1985). Biodegradation: Biotransformation: Bioconcentration, Uptake (k1) and Elimination (k2) Rate Constants: k1 = 78.5 h–1 (zebrafish, Zok et al. 1991) Half-Lives in the Environment: Surface water: overall rate of loss predicted from outdoor ponds was calculated based on direct phototransformation, and indirect phototransformation k = 0.13 to 0.22 d–1 corresponding to t. = 3.2 to 5.3 d; the observed rate of loss varied from 0.11 to 0.17 d–1 corresponding to t. = 4.1 – 6.3 d (Wolff & Crossland 1985). © 2006 by Taylor & Francis Group, LLC Nitrogen and Sulfur Compounds 3263 16.1.3.6 o-Toluidine (2-Methylbenzeneamine) Common Name: o-Toluidine Synonym: 2-aminotoluene, o-aminotoluene, 2-methylaniline, 2-methylbenzeneamine Chemical Name: 2-aminotoluene, o-methylaniline, o-toluidine CAS Registry No: 95-53-4 Molecular Formula: C7H9N, C6H4(CH3)NH2 Molecular Weight: 107.153 Melting Point (°C): –14.41 (Lide 2003) Boiling Point (°C): 200.3 (Lide 2003) Density (g/cm3 at 20°C): 0.9984, 0.99430 (10, 25°C, Dreisbach 1955, Riddick et al. 1986) 0.9984 (20°C, Weast 1982–83) Molar ]Volume (cm3/mol): 107.3 (20°C, calculated-density, Stephenson & Malanowski 1987) 132.4 (calculated-Le Bas method at normal boiling point) Dissociation Constant, pKa: 4.40, 4.447, 4.46 (Perrin 1972) 4.44 (Weast 1982–83) 4.45 (protonated cation + 1, Dean 1985) 4.43 (Sangster 1989) Enthalpy of Vaporization, .HV (kJ/mol): 56.739, 44.597 (25°C, bp, Riddick et al. 1986) Enthalpy of Fusion, .Hfus (kJ/mol): 7.535 (Dreisbach 1955) Entropy of Fusion, .Sfus (J/mol K): Fugacity Ratio at 25°C (assuming .Sfus = 56 J/mol K), F: 1.0 Water Solubility (g/m3 or mg/L at 25°C): 16330 (20°C, shake flask-GC, Chiou 1981; Chiou & Schmedding 1981; Chiou et al. 1982) 15000 (quoted, Verschueren 1983) 16300 (calculated-KOW, Muller & Klein 1992) Vapor Pressure (Pa at 25°C and reported temperature dependence equations. Additional data at other temperatures designated * are compiled at the end of this section): 133.3* (48.2°C, static method, measured range 48.2–199.7°C, Kahlbaum 1898) 42.72* (extrapolated-regression of tabulated data, temp range 44–199.7°C, Stull 1947) log (P/mmHg) = 7.60681 – 2033.6/(230 + t/°C) (Antoine eq., Dreisbach & Martin 1949) 7605* (118.46°C, ebulliometry, measured range 118.46–200.30°C, Dreisbach & Shrader 1949) 42.26 (calculated by formula, Dreisbach 1955) log (P/mmHg) = 7.28896 – 1768.7/(201.0 + t/°C); temp range 103–320°C (Antoine eq. for liquid state, Dreisbach 1955) log (P/atm) = [–0.2185 . 12663.4/(T/K)] + 8.440371; temp range 41–203.3°C (Antoine eq., Weast 1972–73) 42.93 (extrapolated-Cox eq., Chao et al. 1983) log (P/mmHg) = [1 – 473.369/(T/K)] . 10^{0.907135 – 6.44774 . 10–4·(T/K) + 4.94693 . 10–7·(T/K)2}; temp range: 300.0–710.0 K (Cox eq., Chao et al. 1983) 13.33, 40.0 (20°C, 30°C, quoted, Verschueren 1983) 33.96 (extrapolated-Antoine eq., Boublik et al. 1984) NH2 CH3 © 2006 by Taylor & Francis Group, LLC 3264 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals log (P/kPa) = 6.20039 – 1623.158/(186.641 + t/°C); temp range 118.5–200.3°C (Antoine eq. from reported exptl. data, Boublik et al. 1984) 43.0 (selected lit., Riddick et al. 1986) log (P/mmHg) = 6.73171 – 2033.6/(230.0 + t/°C); temp range: not specified (Antoine eq., Riddick et al. 1986) 34.18 (extrapolated-Antoine eq., Dean 1985, 1992) log (P/mmHg) = 7.08203 – 1627.72/(187.13 + t/°C); temp range 118–200°C (Antoine eq., Dean l985, 1992) 36.46 (extrapolated-Antoine eq., Stephenson & Malanowski 1987) log (PL/kPa) = 6.26948 – 1672.87/(–81.47 + T/K); temp range 391–474 K, (Antoine eq., Stephenson & Malanowski 1987) log (P/mmHg) = 96.5685 – 6.2643 . 103/(T/K) – 32.265·log (T/K) + 1.2361 . 10–2·(T/K) + 6.2915 . 10–13·(T/K)2; temp range 249–694 K (vapor pressure eq., Yaws 1994) Henry’s Law Constant (Pa·m3/mol at 25°C): 0.095 (calculated-P/C) 0.201 (gas stripping-GC, Altschuh et al. 1999) Octanol/Water Partition Coefficient, log KOW: 1.29 (shake flask-UV, Leo et al. 1971) 1.43 (HPLC-k. correlation, Carlson et al. 1975) 1.63 (RP-HPLC-RT correlation, Veith et al. 1979a) 1.42 (shake flask-UV at pH 7.5, Martin-Villodre et al. 1986) 1.34 (HPLC-RT correlation, average, Ge et al. 1987) 1.32 (shake flask, Log P Database, Hansch & Leo 1987) 1.32 (recommended, Sangster 1989) 1.44, 1.57 (shake flask, HP:C-RT correlation, Wang et al. 1989) 1.43 (recommended, Sangster 1993) 1.32 (recommended, Hansch et al. 1995) Octanol/Air Partition Coefficient, log KOA: Bioconcentration Factor, log BCF: Sorption Partition Coefficient, log KOC: 1.24 (calculated-KOW, Kollig 1993) Environmental Fate Rate Constants, k, or Half-Lives, t.: Volatilization: Photolysis: Hydrolysis: Oxidation: rate constant k = 1 . 104 M–1 s–1 for oxidation by RO2 radicals at 30°C in aquatic systems with t. = 0.8 d (Howard 1972; Hendry et al. 1974; quoted, Mill 1982); rate constant k < 2 . 102 M–1 s–1 for oxidation by singlet oxygen at 25°C in aquatic systems with t. > 100 yr (Foote 1976; Mill 1979; quoted, Mill 1982); photooxidation t. = 62.4 – 3480 h in water, based on estimated rate constants for reactions of representative aromatic amines with OH and RO2 radicals (Mill & Mabey 1985; quoted, Howard et al. 1991); photooxidation t. = 0.394 – 3.94 h in air, based on estimated rate constant for the reaction with hydroxyl radical in air (Atkinson 1987; quoted, Howard et al. 1991). Biodegradation: decomposition by a soil microflora in > 64 d (Alexander & Lustigman 1966; quoted, Verschueren 1983); aqueous aerobic t. = 24 – 168 h, based on aqueous aerobic screening test data (Baird et al. 1977; Sasaki 1978; quoted, Howard et al. 1991); average biodegradation k = 15.1 mg COD g–1 h–1 for 97.7% removal (Scow 1982); aqueous anaerobic t. = 96 – 672 h, based on estimated unacclimated aqueous aerobic biodegradation halflife (Howard et al. 1991). Biotransformation: © 2006 by Taylor & Francis Group, LLC Nitrogen and Sulfur Compounds 3265 Bioconcentration, Uptake (k1) and Elimination (k2) Rate Constants: Half-Lives in the Environment: Air: photooxidation t. = 0.394 – 3.94 h, based on estimated rate constant for the reaction with hydroxyl radical in air (Atkinson 1987; quoted, Howard et al. 1991); atmospheric transformation lifetime was estimated to be < 1 d (Kelly et al. 1994). Surface water: estimated t. = 1.0 d for methylaniline in Rhine River in case of a first order reduction process (Zoeteman et al. 1980) photooxidation t. = 62.4 – 3480 h, based on estimated rate constants for reactions of representative aromatic amines with OH and RO2 radicals (Mill & Mabey 1985; quoted, Howard et al. 1991). Groundwater: t. = 48 – 336 h, based on estimated unacclimated aqueous aerobic biodegradation half-life (Howard et al. 1991). Sediment: Soil: t. = 24 – 168 h, based on estimated unacclimated aqueous aerobic biodegradation half-life (Howard et al. 1991). Biota: TABLE 16.1.3.6.1 Reported vapor pressures of o-toluidine at various temperatures Kahlbaum 1898 Stull 1947 Dreisbach & Shrader 1949 static method-manometer* summary of literature data ebulliometry t/°C P/Pa t/°C P/Pa t/°C P/Pa 48.2 133.3 44.0 133.3 118.46 7605 55.3 266.6 69.3 666.6 122.22 8851 61.4 400.0 81.4 1333 125.99 10106 65.7 533.3 95.1 2666 139.0 16500 69.3 666.6 110.0 5333 168.06 42066 81.4 1333.2 119.8 7999 184.80 67661 94.9 2666.4 133.0 13332 200.30 101325 103.6 3999.7 153.0 26664 110.0 5332.9 170.2 53329 115.1 6666.1 199.7 101325 125.4 9999.2 133.0 13332 mp/°C –16.3 154.0 26664 166.2 39997 176.2 53329 183.9 66661 190.5 79993 196.2 93326 199.7 101325 *complete list see ref. © 2006 by Taylor & Francis Group, LLC 3266 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals FIGURE 16.1.3.6.1 Logarithm of vapor pressure versus reciprocal temperature for o-toluidine. o -Toluidine: vapor pressure vs. 1/T 0.0 1.0 2.0 3.0 4.0 5.0 6.0 7.0 8.0 0.0018 0.0022 0.0026 0.003 0.0034 0.0038 0.0042 1/(T/K) P( gol S ) aP/ Kahlbaum 1898 Dreisbach & Shrader 1949 Stull 1947 b.p. = 200.3 °C m.p. = -14.41 °C © 2006 by Taylor & Francis Group, LLC Nitrogen and Sulfur Compounds 3267 16.1.3.7 m-Toluidine (3-Methylbenzeneamine) Common Name: m-Toluidine Synonym: 3-aminotoluene, 3-methylbenzeneamine, 3-methylaniline Chemical Name: 3-aminotoluene, m-amino-methylbenzene, m-methylaniline, m-toluidine CAS Registry No: 108-44-1 Molecular Formula: C6H4(CH3)NH2 Molecular Weight: 107.153 Melting Point (oC): –31.3 (Lide 2003) Boiling Point (°C): 203.3 (Stull 1947; Weast 1982–83; Lide 2003) Density (g/cm3 at 20°C): 0.9889 (Dreisbach 1955; Weast 1982–83) Molar Volume (cm3/mol): 108.4 (20°C, Stephenson & Malanowski 1987) 132.4 (calculated-Le Bas method at normal boiling point) Dissociation Constant, pKa: 4.66, 4.712, 4.72 (Perrin 1972) 4.73 (Weast 1982–83) 4.71 (protonated cation + 1, Dean 1985) 4.70 (Sangster 1989) Enthalpy of Vaporization, .HV (kJ/mol): 57.283, 44.848 (25°C, bp, Riddick et al. 1986) Enthalpy of Fusion, .Hfus (kJ/mol): 7.08 (Dreisbach 1955) 3.891 (Riddick et al. 1986) Entropy of Fusion, .Sfus (J/mol K): Fugacity Ratio at 25°C (assuming .Sfus = 56 J/mol K), F: 1.0 Water Solubility (g/m3 or mg/L at 25°C): 15031 (20°C, shake flask-GC, Chiou 1981; Chiou & Schmedding 1981; Chiou et al. 1982) Vapor Pressure (Pa at 25°C and reported temperature dependence equations. Additional data at other temperatures designated * are compiled at the end of this section): 133.3* (49.8°C, static method, measured range 49.8–203.3°C, Kahlbaum 1898) 49.54* (extrapolated-regression of tabulated data, temp range 41–203.3°C, Stull 1947) log (P/mmHg) = 7.616512 – 2052.0/(230 + t/°C) (Antoine eq., Dreisbach & Martin 1949) 7605* (121.77°C, ebulliometry, measured range 121.77-203.34°C, Dreisbach & Shrader 1949) 36.64 (calculated by formula, Dreisbach 1955) log (P/mmHg) = 7.27435 – 1772.06/(200.0 + t/°C); temp range 105–320°C (Antoine eq. for liquid state, Dreisbach 1955) log (P/mmHg) = [–0.2185 . 12104.1/(T/K)] + 8.440371; temp range 41–203°C (Antoine eq., Weast 1972–73) 33.49 (calculated-Cox eq., Chao et al. 1983) log (P/atm) = [1– 476.329/(T/K)] . 10^{0.923479 – 6.91988 . 10–4·(T/K) + 5.41104 . 10–7·(T/K)2}; temp range: 280.0–705.0 K (Cox eq., Chao et al. 1983) 27.91 (extrapolated-Antoine eq., Boublik et al. 1984) log (P/kPa) = 6.21454 – 1620.608/(203.346 + t/°C); temp range 121.9–203.4°C (Antoine eq. from reported exptl. data, Boublik et al. 1984) 25.66 (extrapolated-Antoine eq., Dean 1985, 1992) NH2 CH3 © 2006 by Taylor & Francis Group, LLC 3268 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals log (P/mmHg) = 7.09367 – 1631.43/(183.91 + t/°C); temp range 122–203°C (Antoine eq., Dean l985, 1992) 36.0 (quoted lit., Riddick et al. 1986) log (P/kPa) = 17.6292 – 3200.9/(T/K) – 3.323·log (T/K), temp range not specified (vapor pressure eq., Riddick et al. 1986) 26.86 (extrapolated-Antoine eq., Stephenson & Malanowski 1987) log (PL/kPa) = 6.27299 – 1669.26/(–85.339 + T/K); temp range 394–447 K (Antoine eq., Stephenson & Malanowski 1987) 25.50 (calculated-Cox eq., Chao et al. 1990) log (P/mmHg) = 7.0317 – 3.2034 . 103/(T/K) + 2.3006·log (T/K) – 9.7791 . 10–3·(T/K) + 4.6824 . 10–6·(T/K)2; temp range 243–709 K (vapor pressure eq., Yaws 1994) Henry’s Law Constant (Pa·m3/mol at 25°C): 0.257 (calculated-P/C) 0.169 (gas stripping-GC, Altschuh et al. 1999) Octanol/Water Partition Coefficient, log KOW: 1.40 (shake flask-UV, Fujita et al. 1964) 1.43 (HPLC-k. correlation, Carlson et al. 1975) 1.42 (20°C, shake flask-UV, Briggs 1981) 1.43 (shake flask, Log P Database, Hansch & Leo 1987) 1.40 (recommended, Sangster 1989) 1.49, 1.37 (shake flask, HPLC-RT correlation, Wang et al. 1989) 1.40 (recommended, Hansch et al. 1995) Octanol/Air Partition Coefficient, log KOA: Bioconcentration Factor, log BCF: Sorption Partition Coefficient, log KOC: 1.41 (soil, quoted obs. as log KOM, Sabljic 1987) 1.65 (soil, calculated-MCI 1., Sabljic et al. 1995) Environmental Fate Rate Constants, k, or Half-Lives, t.: Volatilization: Photolysis: Hydrolysis: Oxidation: rate constant k = 1 . 104 M–1 s–1 for oxidation by RO2 radical at 30°C in aquatic systems with t. = 0.8 d (Howard 1972; Hendry et al. 1974; quoted, Mill 1982); k < 2 . 102 M–1 s–1 for oxidation by singlet oxygen at 25°C in aquatic systems with t. > 100 yr (Foote 1976; Mill 1979; quoted, Mill 1982). Biodegradation: decomposition by a soil microflora in 8 d (Alexander & Lustigman 1966; quoted, Verschueren 1983); average biodegradation rate of 30.0 mg COD g–1 h–1 for 97.7% removal (Scow 1982). Biotransformation: Bioconcentration, Uptake (k1) and Elimination (k2) Rate Constants: Half-Lives in the Environment: Surface water: estimated t. = 1.0 d for methylaniline in Rhine River in case of a first order reduction process (Zoeteman et al. 1980) © 2006 by Taylor & Francis Group, LLC Nitrogen and Sulfur Compounds 3269 TABLE 16.1.3.7.1 Reported vapor pressures of m-toluidine at various temperatures Kahlbaum 1898 Stull 1947 Dreisbach & Shrader 1949 static method-manometer* summary of literature data ebulliometry t/°C P/Pa t/°C P/Pa t/°C P/Pa 49.8 133.3 41.0 133.3 121.77 7605 58.9 266.6 68.0 666.6 125.57 8851 64.8 400.0 82.0 1333 129.03 10114 69.3 533.3 96.7 2666 142.27 16500 72.8 666.6 113.5 5333 171.18 42066 85.3 1333.2 123.8 7999 187.87 67661 98.5 2666.4 136.7 13332 203.34 101325 107.1 3999.7 157.6 26664 113.6 5332.9 180.6 53329 118.7 6666.1 203.3 101325 129.0 9999.2 136.6 13332 mp/°C –31.5 157.6 26664 169.8 39997 179.8 53329 187.5 66661 194.0 79993 199.8 93326 203.3 101325 *complete list see ref. FIGURE 16.1.3.7.1 Logarithm of vapor pressure versus reciprocal temperature for m-toluidine. m-Toluidine: vapor pressure vs. 1/T 0.0 1.0 2.0 3.0 4.0 5.0 6.0 7.0 8.0 0.0018 0.0022 0.0026 0.003 0.0034 0.0038 0.0042 0.0046 1/(T/K) P ( g o l S ) a P / Kahlbaum 1898 Dreisbach & Shrader 1949 Stull 1947 b.p. = 203.3 °C m.p. = -31.3 °C © 2006 by Taylor & Francis Group, LLC 3270 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals 16.1.3.8 p-Toluidine (4-Methylbenzeneamine) Common Name: p-Toluidine Synonym: 4-aminotoluene, 4-methylaniline, 4-methylbenzenamine Chemical Name: 4-aminotoluene, p-amino-methylbenzene, p-methylaniline, p-toluidine CAS Registry No: 106-49-0 Molecular Formula: C6H4(CH3)NH2 Molecular Weight: 107.153 Melting Point (°C): 43.6 (Lide 2003) Boiling Point (C): 200.4 (Lide 2003) Density (g/cm3 at 20°C): 0.9619 (20°C, Weast 1982–83) 1.043 (Verschueren 1983) Molar Volume (cm3/mol): 132.4 (calculated-Le Bas method at normal boiling point) Dissociation Constant, pKa: 5.02, 5.08, 5.084 (Perrin 1972) 5.08 (Weast 1982–83; Sangster 1989) 5.08 (protonated cation + 1, Dean 1985) 5.17 (shake flask-HPLC/UV, Johnson & Westall 1990) Enthalpy of Vaporization, .HV (kJ/mol): 56.195, 44.271 (25°C, bp, Riddick et al. 1986) Enthalpy of Fusion, .Hfus (kJ/mol): 17.32 (Tsonopoulos & Prausnitz 1971) 18.91 (Riddick et al. 1986) Entropy of Fusion, .Sfus (J/mol K): 54.81 (Tsonopoulos & Prausnitz 1971) 57.61 (observed, Yalkowsky & Valvani 1980) Fugacity Ratio at 25°C (assuming .Sfus = 56 J/mol K), F: 0.657 (mp at 43.6°C) Water Solubility (g/m3 or mg/L at 25°C as indicated): 65400 (20–25°C, shake flask-gravimetric, Dehn 1917) 8965 (Seidell 1941, 1952) 7400 (21°C, Verschueren 1983) 6643, 5370 (20°C, shake flask-UV, calculated, Hashimoto et al. 1984) Vapor Pressure (Pa at 25°C or as indicated and reported temperature dependence equations. Additional data at other temperatures designated * are compiled at the end of this section): 133.3* (46.9°C, static method, measured range 46.9–200.4°C, Kahlbaum 1898) log (P/mmHg) = –2597/(T/K) + 8.366 (isoteniscope method, temp range not specified, Kobe et al. 1941) 46.27* (extrapolated-regression of tabulated data, temp range 42–200.4°C, Stull 1947) 44.70 (calculated by formula, Dreisbach 1955) log (P/mmHg) = 7.25173 – 1755.0/(201.0 + t/°C); temp range 103–330°C (Antoine eq. for liquid state, Dreisbach 1955) log (P/atm) = [–0.2185 . 12428.6/(T/K)] + 8.748585; temp range 42–200.4°C (Antoine eq., Weast 1972–73) 38.13 (calculated-Cox eq., Chao et al. 1983) NH2 CH3 © 2006 by Taylor & Francis Group, LLC Nitrogen and Sulfur Compounds 3271 log (P/mmHg) = [1– 473.445/(T/K)] . 10^{0.915691 – 6.57014 . 10–4·(T/K) + 5.11261 . 10–7·(T/K)2}; temp range 290.0–700.0 K (Cox eq., Chao et al. 1983) 40.17 (calculated-Antoine eq., Dean 1985, 1992) log (P/mmHg) = 7.26022 – 1758.55/(201.0 + t/°C); temp range not specified (Antoine eq., Dean 1985,1992) 45.0 (quoted lit., Riddick et al. 1986) log (P/kPa) = 18.2818 – 3269.3/(T/K) – 3.877·log (T/K); temp range not specified (vapor pressure eq., Riddick et al. 1986) 27.03 (extrapolated-Antoine eq., Stephenson & Malanowski 1987) log (PL/kPa) = 6.17451 – 1585.0/(–93.44 + T/K); temp range 393–474 K (Antoine eq., Stephenson & Malanowski 1987) log (P/mmHg) = –13.9927 – 2.5795 . 103/(T/K) –10.823·log (T/K) –1.7705 . 10–2·(T/K) + 7.6741 . 10–6·(T/K)2; temp range 317–693 K (vapor pressure eq., Yaws 1994) Henry’s Law Constant (Pa·m3/mol at 25°C): 0.656 (calculated-P/C) 0.0768 (gas stripping-GC, Altschuh et al. 1999) Octanol/Water Partition Coefficient, log KOW: 1.39 (shake flask-UV, Fujita et al. 1964) 1.41 (HPLC-k. correlation, Carlson et al. 1975) 1.56 (shake flask-UV, Ezumi & Kubota 1980) 1.40 (20°C, shake flask-UV, Briggs 1981) 1.44 ± 0.03 (HPLC-RV correlation-ALPM, Garst & Wilson 1984) 1.42 (HPLC-k. correlation, Haky & Young 1984) 1.39 (shake flask-UV at pH 7.5, Martin-Villodre et al. 1986) 1.41 (HPLC-RT correlation, average, Ge et al. 1987) 1.39 (shake flask, Leahy et al. 1989) 1.39 (recommended, Sangster 1989, 1993) 1.38, 1.39 (shake flask, HPLC-RT correlation, Wang et al. 1989) 1.40 (shake flask-HPLC/UV, Johnson & Westall 1990) 1.40 (shake flask-UV, Roberts et al. 1991) 1.40 (32°C, shake flask-UV, pH 7, Takahashi et al.1993) 1.39 (recommended, Hansch et al. 1995) Octanol/Air Partition Coefficient, log KOA: Bioconcentration Factor, log BCF: Sorption Partition Coefficient, log KOC: 2.51, 2.70, 2.71 (Morocco soil, Oakville soil, Milford soil, Graveel et al. 1986) 1.66 (soil, quoted obs. as log KOM, Sabljic 1987) 2.74, 2.22, 2.20 (Podzol soil, Alfisol soil, sediment, von Oepen et al. 1991) 1.24 (calculated-KOW, Kollig 1993) 1.90 (soil, calculated-MCI 1., Sabljic et al. 1995) 2.21; 1.86 (HPLC-screening method; calculated-PCKOC fragment method, Muller & Kordel 1996) 3.28, 2.01, 2.30, 2.084 (first generation Eurosoils ES-1, ES-2, ES-3, ES-4, shake flask/batch equilibrium- HPLC/UV, Gawlik et al. 1998) 2.138, 2.133, 2.212, 2.041 (second generation Eurosoils ES-1, ES-2, ES-3, ES-4, shake flask-batch equilibrium- HPLC/UV and HPLC-k. correlation, Gawlik et al. 2000) Environmental Fate Rate Constants, k, or Half-Lives, t.: Volatilization: Photolysis: Hydrolysis: © 2006 by Taylor & Francis Group, LLC 3272 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals Oxidation: rate constant k = 1 . 104 M–1 s–1 for oxidation by RO2 radical at 30°C in aquatic systems with t. = 0.8 d (Howard 1972; Hendry et al. 1974; quoted, Mill 1982); k < 2 . 102 M–1 s–1 for oxidation by singlet oxygen at 25°C in aquatic systems with t. > 100 yr (Foote 1976; Mill 1979; quoted, Mill 1982). Biodegradation: decomposition by a microflora in 4 d (Alexander & Lustigman 1966; quoted, Verschueren 1983); average biodegradation rate of 20 mg COD g–1 h–1 for 97.7% removal (Scow 1982). Biotransformation: Bioconcentration, Uptake (k1) and Elimination (k2) Rate Constants: Half-Lives in the Environment: Surface water: estimated t. = 1.0 d for methylaniline in Rhine River in case of a first order reduction process (Zoeteman et al. 1980) TABLE 16.1.3.8.1 Reported vapor pressures of p-toluidine at various temperatures Kahlbaum 1898 Stull 1947 static method-manometer* summary of literature data t/°C P/Pa t/°C P/Pa 46.9 133.3 42.0 133.3 55.9 266.6 68.2 666.6 62.0 400.0 81.8 1333 66.4 533.3 95.8 2666 70.1 666.6 111.5 5333 82.2 1333.2 121.5 7999 95.6 2666.4 133.7 13332 104.3 3999.7 154.0 26664 110.7 5332.9 176.9 53329 115.8 6666.1 200.4 101325 126.1 9999.2 133.7 13332 mp/°C 44.5 154.7 26664 166.9 39997 176.9 53329 184.6 66661 191.1 79993 196.9 93326 200.4 101325 *complete list see ref. © 2006 by Taylor & Francis Group, LLC Nitrogen and Sulfur Compounds 3273 FIGURE 16.1.3.8.1 Logarithm of vapor pressure versus reciprocal temperature for p-toluidine. p -Toluidine: vapor pressure vs. 1/T 0.0 1.0 2.0 3.0 4.0 5.0 6.0 7.0 8.0 0.0018 0.002 0.0022 0.0024 0.0026 0.0028 0.003 0.0032 0.0034 1/(T/K) P( gol S ) aP/ Kahlbaum 1898 Stull 1947 b.p. = 200.4 °C m.p. = 43.6 °C © 2006 by Taylor & Francis Group, LLC 3274 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals 16.1.3.9 N,N’-Dimethylaniline Common Name: N,N.-Dimethylaniline Synonym: N,N.-dimethylbenzenamine Chemical Name: N,N.-dimethylaniline CAS Registry No: 121-69-7 Molecular Formula: C8H11N, C6H5N(CH3)2 Molecular Weight: 121.180 Melting Point (°C): 2.42 (Lide 2003) Boiling Point (°C): 194.0 (Weast 1982–83) 194.15 (Lide 2003) Density (g/cm3 at 20°C): 0.9557 (Weast 1982–83) Molar Volume (cm3/mol): 154.6 (calculated-Le Bas method at normal boiling point) Dissociation Constant pK: 5.15 (pKBH + , Riddick et al. 1986) 5.10 (Sangster 1993) Enthalpy of Fusion, .Hfus (kJ/mol): 11.42 (Tsonopoulos & Prausnitz 1971) Entropy of Fusion, .Sfus (J/mol K): 41.46 (Tsonopoulos & Prausnitz 1971) Fugacity Ratio at 25°C (assuming .Sfus = 56 J/mol K), F: 1.0 Water Solubility (g/m3 or mg/L at 25°C or as indicated): 1105 (shake flask-GC, Chiou et al. 1982) 1540, 1680 (20, 30°C, shake flask-GC/TC, measured range 0–90°C, Stephenson 1993c) Vapor Pressure (Pa at 25°C and reported temperature dependence equations): 106.3 (extrapolated-regression of tabulated data, temp range 20.0–193.1°C, Stull 1947) 133.3 (29.5°C, Stull 1947) 83.90 (calculated-Antoine eq., Boublik et al. 1973) log (P/atm) = [–0.2185 . 11320.4/(T/K)] + 8.197379; temp range: 29.5–193°C, (Antoine eq., Weast 1972–73) 68.95 (calculated-Cox eq., Chao et al. 1983) log (P/mmHg) = [1– 466.445/(T/K)] . 10^{0.909397 – 7.07673 . 10–4 ± (T/K) + 5.69581 . 10–7 ± (T/K)2}; temp range 275.0–685.0 K (Cox eq., Chao et al. 1983) 84.5 (extrapolated-Antoine eq., Boublik et al. 1984) log (P/kPa) = 6.5031 – 1865.084/(211.171 + t/°C); temp range 71.02–196.8°C (Antoine eq. from reported exptl. data, Boublik et al. 1984) 83.91 (extrapolated-Antoine eq., Dean 1985, 1992) log (P/mmHg) = 6.91048 – 946.35/(246.68 + t/°C); temp range –87 to 7°C (Antoine eq., Dean 1985, 1992) 670.0 (quoted from Stull 1947, Riddick et al. 1986) 107.0 (extrapolated-Antoine eq., Stephenson & Malanowski 1987) log (PL/kPa) = 7.07329 – 2301.63/(–12.001 + T/K); temp range 302–467 K (liquid, Antoine eq.-I, Stephenson & Malanowski 1987) log (PL/kPa) = 6.55663 – 1864.075/(–55.854 + T/K); temp range 363–418 K (liquid, Antoine eq.-II, Stephenson & Malanowski 1987) N © 2006 by Taylor & Francis Group, LLC Nitrogen and Sulfur Compounds 3275 log (P/mmHg) = 2–.177 – 3.1095 . 103/(T/K) – 4.0127·log (T/K) + 5.8538 . 10–10·(T/K) + 3.5387 . 10–7·(T/K)2; temp range 276–687 K (vapor pressure eq., Yaws 1994) Henry’s Law Constant (Pa·m3/mol): 11.73 (calculated-P/C) Octanol/Water Partition Coefficient, log KOW: 2.31 (shake flask-UV, Fujita et al. 1964) 2.62 (shake flask-UV at pH 7.4, Rogers & Cammarata 1969) 1.66 (shake flask-UV, Leo et al. 1971) 2.29 (shake flask-UV, Yaguzhinskii et al. 1973) 2.30 (shake flask at pH 7, Unger et al. 1978) 2.43 (HPLC-RT correlation, Miyake et al. 1986) 2.28 (RP-HPLC-RT correlation, ODS column with masking agent, Bechalany et al. 1989) 2.32 (CPC correlation, El Tayar et al. 1991) 2.31 (recommended, Sangster 1993) 2.31 (recommended, Hansch et al. 1995) 2.05 (microemulsion electrokinetic chromatography-retention factor correlation, Poole et al. 2000) Octanol/Air Partition Coefficient, log KOA: Bioconcentration Factor, log BCF: Sorption Partition Coefficient, log KOC: 1.99; 2.53; 2.06 (Alfisol soil; Podzol soil; sediment, von Oepen et al. 1991) 2.26, 1.89 (soil, quoted, calculated-MCI . and fragment contribution, Meylan et al. 1992) 2.26 (soil, calculated-MCI 1., Sabljic et al. 1995) Environmental Fate Rate Constants, k, or Half-Lives, t.: Volatilization: Photolysis: Oxidation: rate constant k; for gas-phase second order rate constants, kOH for reaction with OH radical, kNO3 with NO3 radical and kO3 with O3 or as indicated, *data at other temperatures see reference: k = 1 . 104 M–1 s–1 for oxidation by RO2 radical at 30°C in aquatic systems with t. = 0.8 d (Howard 1972; Hendry et al. 1974; quoted, Mill 1982) k < 2 . 102 M–1 s–1 for oxidation by singlet oxygen at 25°C in aquatic systems with t. > 100 yr (Foote 1976; Mill 1979; quoted, Mill 1982) kOH*(exptl) = (1.48 ± 0.11) . 10–10 cm3 molecule–1 s–1, measured range 278–464 K; kO3 = (9.1 ± 1.0) . 10–18 cm3 molecule–1 s–1 at 296 ± 2 K (relative rate method, Atkinson et al. 1987) kOH = 1.5 . 10–10 cm3 molecule–1 s–1 with atmospheric lifetimes of 1.9 h in clean troposphere and 1.0 h in moderately polluted atmosphere; kO3 = 9.1 . 10–18 cm3 molecule–1 s–1 with atmospheric lifetimes of 1.8 d in clean troposphere and 14 h in moderately polluted atmosphere at room temp. (Atkinson et al. 1987) kOH(calc) = 4.66 . 10–10 cm3 molecule–1 s–1, kOH(obs) = 1.48 . 10–10 cm3 molecule–1 s–1, (SAR structureactivity relationship, Atkinson 1987) kOH(calc) = 1.78 . 10–10 cm3 molecule–1 s–1 (molecular orbital calculations, Klamt 1993) Hydrolysis: Biodegradation: aerobic t. = 672–4320 h, based on unacclimated aqueous screening test data and anaerobic t. = 2880–17280 h, based on estimated unacclimated aqueous aerobic biodegradation half-life (Howard et al. 1991) Biotransformation: Bioconcentration, Uptake (k1) and Elimination (k2) Rate Constants: Half-Lives in the Environment: Air: atmospheric lifetimes of 1.9 h in clean troposphere and 1.0 h in moderately polluted atmosphere, based on the gas-phase reaction with hydroxyl radical in air at room temp.; atmospheric lifetimes of 1.8 d in clean © 2006 by Taylor & Francis Group, LLC 3276 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals troposphere and 14 h in moderately polluted atmosphere, based on the gas-phase reaction with O3 in air at room temp. (Atkinson et al. 1987); t. = 2.7–21 h, based on photooxidation half-life in air (Howard et al. 1991); atmospheric transformation lifetime was estimated to be < 1 d (Kelly et al. 1994). Surface water: estimated t. = 2.3 d in Rhine River in case of a first order reduction process (Zoeteman et al. 1980) t. = 19.3–1925 h, based on reaction with singlet oxygen in aqueous solution (Howard et al. 1991) Groundwater: t. = 1344–8640 h, based on estimated unacclimated aqueous aerobic biodegradation half-life (Howard et al. 1991) Sediment: Soil: t. = 672–4320 h, based on estimated unacclimated aqueous aerobic biodegradation half-life (Howard et al. 1991) Biota: © 2006 by Taylor & Francis Group, LLC Nitrogen and Sulfur Compounds 3277 16.1.3.10 2,6-Xylidine (2,6-Dimethylbenzeneamine) Common Name: 2,6-Xylidine Synonym: 2,6-dimethylaniline, 2,6-dimethylbenzeneamine Chemical Name: 2,6-dimethylaniline CAS Registry No: 87-62-7 Molecular Formula: C8H11N, 2,6-(CH3)2C6H3NH2 Molecular Weight: 121.180 Melting Point (°C): 11.20 (Weast 1982–83; Riddick et al. 1986; Lide 2003) Boiling Point (°C): 214.0 (at 739 mm Hg, Weast 1982–83; Verschueren 1983) 215 (Lide 2003) Density (g/cm3 at 20°C): 0.9842 (Weast 1982–83; Riddick et al. 1986) Molar Volume (cm3/mol): 123.1 (20°C, calculated-density) 154.6 (calculated-Le Bas method at normal boiling point) Dissociation Constant pK: 3.95 (pKBH + , Riddick et al. 1986) Enthalpy of Fusion, .Hfus (kJ/mol): Entropy of Fusion, .Sfus (J/mol K): Fugacity Ratio at 25°C (assuming .Sfus = 56 J/mol K), F: 1.0 Water Solubility (g/m3 or mg/L at 25°C): slightly soluble (Dean 1985; Budavari 1989) Vapor Pressure (Pa at 25°C and reported temperature dependence equations): 43.03 (extrapolated-regression of tabulated data, temp range 44–217.9°C, Stull 1947) log (P/atm) = [1– 490.795/(T/K)] . 10^{0.926009 – 6.89676 . 10–4·(T/K) + 5.31053 . 10–7·(T/K)2}; temp range: 285.0–720.0 K (Cox eq., Chao et al. 1983) 17.33 (Howard et al. 1986) 670.0 (quoted from Stull 1947, Riddick et al. 1986) 35.99 (calculated-solvatochromic parameters, Banerjee et al. 1990) Henry’s Law Constant (Pa·m3/mol at 25°C): 17.28 (calculated-P/C from selected value) Octanol/Water Partition Coefficient, log KOW: 1.96 (calculated, Verschueren 1983) 1.91 (calculated-CLOGP, Jackel & Klein 1991) Octanol/Air Partition Coefficient, log KOA: Bioconcentration Factor, log BCF: Sorption Partition Coefficient, log KOC: NH2 © 2006 by Taylor & Francis Group, LLC 3278 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals Environmental Fate Rate Constants, k, or Half-Lives, t.: Volatilization: Photolysis: Oxidation: rate constant k = 1 . 104 M–1 s–1 for oxidation by RO2 radical at 30°C in aquatic systems with t. = 0.8 d (Howard 1972; Hendry et al. 1974; quoted, Mill 1982); k < 2 . 102 M–1 s–1 for oxidation by singlet oxygen at 25°C in aquatic systems with t. > 100 yr (Foote 1976; Mill 1979; quoted, Mill 1982); photooxidation t. = 0.33–3.3 h in air, based on estimated reaction rate constant with OH radical (Atkinson 1987; selected, Howard et al. 1991) and photooxidation t. = 62.4–3480 h in water, based on reaction rate constants of amine class with RO2· and OH radicals in water (Guesten et al. 1981; Mill & Mabey 1985; selected, Howard et al. 1991). Hydrolysis: no hydrolyzable group (Howard et al. 1991). Biodegradation: aqueous aerobic biodegradation t. = 672–4320 h, based on a biological screening study (Baird et al. 1977; selected Howard et al. 1991) and a soil degradation study (Bollag et al. 1978; selected, Howard et al. 1991); aqueous anaerobic biodegradation t. = 2688–17280 h, based on estimated aqueous biodegradation half-lives (Howard et al. 1991). Biotransformation: Bioconcentration, Uptake (k1) and Elimination (k2) Rate Constants: Half-Lives in the Environment: Air: t. = 0.33–3.3 h, based on estimated photooxidation half-lives in air from estimated reaction rate constant with OH radical in air (Atkinson 1987; selected, Howard et al. 1991). Surface water: estimated t. = 2.0 d for dimethylaniline in Rhine River in case of a first order reduction process (Zoeteman et al. 1980) t. = 62.4–3480 h, based on photooxidation half-life in water (Howard et al. 1991). Groundwater: t. = 1344–8640 h, based on estimated aqueous aerobic biodegradation half-lives (Howard et al. 1991). Sediment: Soil: t. = 72–7584 h, based on soil persistence and soil biodegradation studies (Bollag et al. 1978; Medvedev & Davidov 1981; selected, Howard et al. 1991). Biota: © 2006 by Taylor & Francis Group, LLC Nitrogen and Sulfur Compounds 3279 16.1.3.11 Diphenylamine Common Name: Diphenylamine Synonym: N-diphenylamine, N-phenyl aniline, DPA Chemical Name: N-diphenylamine, diphenylamine CAS Registry No: 122-39-4 Molecular Formula: C12H11N, C6H5NHC6H5 Molecular Weight: 169.222 Melting Point (°C): 53.2 (Lide 2003) Boiling Point (°C): 302.0 (Stull 1947; Weast 1982–83; Verschueren 1983; Dean 1985; Lide 2003) Density (g/cm3 at 20°C): 1.160 (Weast 1982–83; Dean 1985) Molar Volume (cm3/mol): 145.9 (20°C calculated-density) 200.3 (calculated-Le Bas method at normal boiling point) Dissociation Constant, pKa: 0.89 (Perrin 1972) 0.90 (protonated cation + 1, Dean 1985) 0.78 (Sangster 1989) Enthalpy of Fusion, .Hfus (kJ/mol): 17.53 (Tsonopoulos & Prausnitz 1971) Entropy of Fusion, .Sfus (J/mol K): 53.56 (Tsonopoulos & Prausnitz 1971) 54.81; 56.5 (exptl., calculated, Yalkowsky & Valvani 1980) Fugacity Ratio at 25°C (assuming .Sfus = 56 J/mol K), F: 0.529 (mp at 53.2°C) Water Solubility (g/m3 or mg/L at 25°C as indicated): 150 (20–25°C, shake flask-gravimetric method, Dehn 1917) 308 (Briggs 1981) 48 (20°C, shake flask and membrane filter-fluorophotometric, Hashimoto et al. 1982) 52, 54 (20°C, shake flask and glass fiber filters-fluorophotometric, Hashimoto et al. 1982) 300 (Verschueren 1983) 53 (20°C, Yalkowsky et al. 1987) Vapor Pressure (Pa at 25°C and reported temperature dependence equations. Additional data at other temperatures designated * are compiled at the end of this section): 0.5682* (extrapolated-regression of tabulated data, temp range 108.3–302°C, Stull 1947) log (P/mmHg) = [–0.2185 . 14920.3/(T/K)] + 8.564067; temp range 108.3–302°C (Antoine eq., Weast 1972–73) log (P/atm) = [1 – 575.114/(T/K)] . 10^{0.936992 – 6.17195 . 10–4·(T/K) + 4.32696 . 10–7·(T/K)2}; temp range 335.0–670.0 K (Cox eq., Chao et al. 1983) 0.0612 (calculated-Antoine eq.-I, Stephenson & Malanowski 1987) log (PS/kPa) = 12.704 – 5043.9/(T/K); temp range 298–323 K (solid, Antoine eq.-I, Stephenson & Malanowski 1987) log (PL/kPa) = 7.15045 – 2778.28/(–35.102 + T/K); temp range 381–575 K (liquid, Antoine eq.-II, Stephenson & Malanowski 1987) log (PL/kPa) = 6.5746 – 2430.7/(–41.15 + T/K); temp range 573–673 K (liquid, Antoine eq.-III, Stephenson & Malanowski 1987) log (P/mmHg) = 9.7736 – 3.9008 . 103/(T/K) + 0.91207·log (T/K) – 5.898 . 10–3·(T/K) + 2.3012 . 10–6·(T/K)2; temp range 326–817 K (vapor pressure eq., Yaws 1994) HN © 2006 by Taylor & Francis Group, LLC 3280 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals Henry’s Law Constant (Pa m3/mol at 25°C): 0.285 (calculated-P/C, Meylan & Howard 1991) 0.106 (estimated-bond contribution, Meylan & Howard 1991) 0.035 (calculated-P/C from selected values) Octanol/Water Partition Coefficient, log KOW: 3.23 (shake flask-UV, pH 7.4, Rogers & Cammarata 1969) 3.34 (unpublished result, Leo et al. 1971) 3.34, 3.50, 3.72 (unpublished results, Rekker 1977) 2.37 (RP-HPLC-RT correlation, Veith et al. 1979a) 3.45 (Hansch & Leo 1979) 3.42 (shake flask-UV, Briggs 1981) 3.37 (inter-laboratory shake flask average, Eadsforth & Moser 1983) 3.72 ± 0.03 (HPLC-RV correlation-ALPM, Garst & Wilson 1984) 2.69 (HPLC-RT correlation, average, Ge et al. 1987) 3.42 (shake flask, Log P Database, Hansch & Leo 1987) 3.50 (recommended, Sangster 1989, 1993) 3.70, 3.68 (shake flask, HPLC-RT correlation, Wang et al. 1989) 3.50 (recommended, Hansch et al. 1995) 2.99, 3.13, 3.04, 3.18 (HPLC-k. correlation, different combinations of stationary and mobile phases under isocratic conditions, Makovskaya et al. 1995) 3.35 (microemulsion electrokinetic chromatography-retention factor correlation, Poole et al. 2000) Octanol/Air Partition Coefficient, log KOA: 7.64 (calculated-Soct and vapor pressure P, Abraham et al. 2001) Bioconcentration Factor, log BCF: 1.48 (fathead minnow, Veith et al. 1979b) 1.48, 2.10 (quoted, calculated-KOW, Mackay 1982) Sorption Partition Coefficient, log KOC: 2.78 (sorption isotherm-GC, converted from KOM organic matter-water in various soils, Briggs 1981) 2.78, 3.28 (soil, calculated-MCI . and fragment contribution, Meylan et al. 1992) 3.30 (calculated-KOW, Kollig 1993) 2.70 (soil, calculated-MCI 1., Sabljic et al. 1995) 2.80, 2.93 (RP-HPLC-k. correlation including MCI related to non-dispersive intermolecular interactions, hydrogen-bonding indicator variable, Hong et al. 1996) Environmental Fate Rate Constants, k, or Half-Lives, t.: Volatilization: Photolysis: Oxidation: rate constant k = 1 . 104 M–1 s–1 for oxidation by RO2 radical at 30°C in aquatic systems with t. = 0.8 d (Howard 1972; Hendry et al. 1974; quoted, Mill 1982); k < 2 . 102 M–1 s–1 for oxidation by singlet oxygen at 25°C in aquatic systems with t. > 100 yr (Foote 1976; Mill 1979; quoted, Mill 1982); photooxidation t. = 31–1740 h in water, based on photooxidation rate constants with OH and RO2 radicals for the amine class (Mill & Mabey 1985; Guesten et al. 1981; selected, Howard et al. 1991); photooxidation t. = 0.247–2.47 h, based on estimated rate data for the reaction with hydroxyl radicals in air (Atkinson 1987; selected, Howard et al. 1991). Hydrolysis: rate constant k = 1.2 . 1010 L mol–1 s–1 for reactions with hydroxyl radical in aqueous solution, (Buxton et al. 1986; quoted, Armbrust 2000); measured hydroxy radical rate constant k = 4.9 . 1013 M–1·h–1 (Armbrust 2000) Biodegradation: aqueous aerobic t. = 168–672 h, based on estimated aqueous aerobic biodegradation screening test data (Malaney 1960; quoted, Howard et al. 1991); © 2006 by Taylor & Francis Group, LLC Nitrogen and Sulfur Compounds 3281 aqueous anaerobic t. = 672–2688 h, based on estimated aqueous aerobic biodegradation half-life (Howard et al. 1991). Biotransformation: Bioconcentration, Uptake (k1) and Elimination (k2) Rate Constants: Half-Lives in the Environment: Air: photooxidation t. = 0.247–2.47 h, based on estimated rate data for the reaction with hydroxyl radical in air (Atkinson 1987; selected, Howard et al. 1991). Surface water: photooxidation t. = 31–1740 h in water, based on photooxidation rate constants with OH and RO2 radicals for the amine class (Mill & Mabey 1985; Guesten et al. 1981; selected, Howard et al. 1991); t. = 31–672 h, based on estimated unacclimated aqueous aerobic degradation half-life and photooxidation half-life in water (Howard et al. 1991). Groundwater: t. = 336–1344 h, based on estimated aqueous aerobic biodegradation half-life (Howard et al. 1991). Sediment: Soil: t. = 168–672 h, based on estimated aqueous aerobic biodegradation half-life (Howard et al. 1991). Biota: TABLE 16.1.3.11.1 Reported vapor pressures of diphenylamine at various temperatures Stull 1947 summary of literature data t/°C P/Pa 108.3 133.3 141.7 666.6 157.0 1333 175.2 2666 194.3 5333 206.9 7999 222.9 13332 247.5 26664 274.1 53329 302.0 101325 mp/°C 52.9 © 2006 by Taylor & Francis Group, LLC 3282 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals FIGURE 16.1.3.11.1 Logarithm of vapor pressure versus reciprocal temperature for diphenylamine. Diphenylamine: vapor pressure vs. 1/T 0.0 1.0 2.0 3.0 4.0 5.0 6.0 7.0 8.0 0.0016 0.0018 0.002 0.0022 0.0024 0.0026 0.0028 0.003 0.0032 1/(T/K) P( gol S ) aP/ Stull 1947 b.p. = 302 °C m.p. = 53.2 °C © 2006 by Taylor & Francis Group, LLC Nitrogen and Sulfur Compounds 3283 16.1.3.12 Benzidine Common Name: Benzidine Synonym: p,p.-bianiline, 4,4.-diaminobiphenyl, 4,4.-biphenyldiamine, (1,1.-biphenyl)-4,4.-diamine Chemical Name: p-benzidine CAS Registry No: 92-87-5 Molecular Formula: C12H12N2, NH2C6H4C6H4NH2 Molecular Weight: 184.236 Melting Point (°C): 128 (Weast 1982–83) 120 (Lide 2003) Boiling Point (°C): 400 (Weast 1982–83) 401 (Lide 2003) Density (g/cm3 at 20°C): 1.250 (Verschueren 1983) Molar Volume (cm3/mol): 213.0 (calculated-Le Bas method at normal boiling point) Dissociation Constant, pKa: 4.66 (pK1), 3.57 (pK2) (30°C, Perrin 1965; quoted, Mabey et al. 1982; Howard 1989) Enthalpy of Fusion, .Hfus (kJ/mol): Entropy of Fusion, .Sfus (J/mol K): Fugacity Ratio at 25°C (assuming .Sfus = 56 J/mol K), F: 0.117 (mp at 120°C) Water Solubility (g/m3 or mg/L at 25°C as indicated): 400 (12°C, Verschueren 1977, 1983) 520 (Shriner et al. 1978) 360 (24°C at pH 5.9, shake flask-LSC, Means et al. 1980) 276 (20°C, Schmidt-Bleek et al. 1982) 359 (Gerstl & Helling 1987) Vapor Pressure (Pa at 25°C): 0.724 (calculated-Trouton’s rule, Mabey et al. 1982) 1.0 . 10–6 (20°C, Schmidt-Bleek et al. 1982) Henry’s Law Constant (Pa·m3/mol at 25°C or as indicated): 3.93 . 10–6 (estimated, Hine & Mookerjee 1975) 0.0394 (calculated-P/C at 12°C, Mabey et al. 1982) 4.60 . 10–7 (calculated-P/C, this work) Octanol/Water Partition Coefficient, log KOW: 1.34 (shake flask, Korenman 1971) 1.34 (recommended, Sangster 1993) 1.34 (recommended, Hansch et al. 1995) Octanol/Air Partition Coefficient, log KOA: Bioconcentration Factor, log BCF: 1.74, 2.66, 2.81, 3.4 (fish, mosquitoes, snail, algae; Lu et al. 1977) 1.60 (bluegills, USEPA 1980; quoted, Howard 1989) 1.00 (microorganisms-water, calculated-KOW, Mabey et al. 1982) H2N NH2 © 2006 by Taylor & Francis Group, LLC 3284 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals 1.90, 2.93, 3.08 (golden ide, algae, activated sludge, Freitag et al. 1985) Sorption Partition Coefficient, log KOC: 1.66 (soil/sediment, equilibrium sorption isotherm by shake flask-LSC at pH 5.9, Means et al. 1980) 1.02 (sediment-water, calculated-KOW, Mabey et al. 1982) 5.95; 5.68; 5.35; 5.91 (Russell soil; Chalmers soil; Kokomo soil; Milford soil, Graveel et al. 1986) 3.00 (calculated-MCI ., Gerstl & Helling 1987) 3.46, 3.44 (soil, quoted, calculated-MCI . and fragment contribution, Meylan et al. 1992) 1.26 (calculated-KOW, Kollig 1993) 3.46 (soil, calculated-MCI 1., Sabljic et al. 1995) Environmental Fate Rate Constants, k, or Half-Lives, t.: Volatilization: Photolysis: Hydrolysis: Oxidation: aqueous oxidation rate constants for singlet oxygen k < 4 . 107 M–1 h–1 and for peroxy radical of 1.1 . 108 M–1 h–1 at 25°C (Mabey et al. 1982); photooxidation t. = 0.312–3.12 h, based on estimated rate constant for the reaction with hydroxyl radical in air (Atkinson 1987; quoted, Howard et al. 1991). Biodegradation: aqueous aerobic t. = 48–192 h, based on aerobic soil die-away test data (Lu et al. 1977; quoted, Howard et al. 1991); overall biodegradation t. = 76 d, when in sludge was applied to a sandy loam soil in a biological soil reactor and worked into the top 20 cm of soil (Kincannon & Lin 1985; quoted, Howard 1989); aqueous aerobic t. = 192–768 h, based on estimated unacclimated aqueous aerobic biodegradation half-life (Howard et al. 1991). Biotransformation: rate constant for bacterial transformation of 1 . 10–10 mL·cell–1·h–1 in water (Mabey et al. 1982). Bioconcentration, Uptake (k1) and Elimination (k2) Rate Constants: Half-Lives in the Environment: Air: t. = 0.312–3.12 h, based on estimated rate constant for the reaction with hydroxyl radical in air (Atkinson 1987; quoted, Howard et al. 1991); estimated t. ~ 1 d for the reaction with hydroxyl radical and ozone (Howard 1989); atmospheric transformation lifetime was estimated to be < 1 d (Kelly et al. 1994). Surface water: estimated t. ~ 1 d for the reaction with radicals and redox reactions with naturally occurring cations, etc. and perhaps with photodegradation (Howard 1989); t. = 31.2–192 h, based on estimated photooxidation half-life in water and estimated unacclimated aqueous aerobic biodegradation half-life (Howard et al. 1991). Ground water: t. = 96–484 h, based on estimated unacclimated aqueous aerobic biodegradation half-life (Howard et al. 1991). Sediment: Soil: t. < 10 d in soil (USEPA 1979; quoted, Ryan et al. 1988); t. = 48–192 h, based on aerobic soil die-away test data (Lu et al. 1977; quoted, Howard et al. 1991); overall biodegradation t. = 76 d, when in sludge was applied to a sandy loam soil in a biological soil reactor and worked into the top 20 cm of soil (Kincannon & Lin 1985; quoted, Howard 1989). Biota: depuration t. ~ 7 d from bluegills (Lu et al. 1977; quoted, Howard 1989). © 2006 by Taylor & Francis Group, LLC Nitrogen and Sulfur Compounds 3285 16.1.3.13 3,3’-Dichlorobenzidine Common Name: 3,3.-Dichlorobenzidine Synonym: 3,3.-dichloro-4,4.-diamino(1,1.-biphenyl), DCB Chemical Name: 3,3.-dichlorobenzidine CAS Registry No: 91-94-1 Molecular Formula: C12H10Cl2N2, NH2C6H3(Cl)C6H3(Cl)NH2 Molecular Weight: 253.126 Melting Point (°C): 132.5 (Lide 2003) Boiling Point (°C): Density (g/cm3 at 20°C): Molar Volume (cm3/mol): 254.8 (calculated-Le Bas method at normal boiling point) Dissociation Constant, pKb: 11.7 (Kollig 1993) Enthalpy of Fusion, .Hfus (kJ/mol): Entropy of Fusion, .Sfus (J/mol K): Fugacity Ratio at 25°C (assuming .Sfus = 56 J/mol K), F: 0.0882 (mp at 132.5°C) Water Solubility (g/m3 or mg/L at 25°C or as indicated): 4.00 (22°C, as dihydrochloride, Banerjee et al. 1978) 3.99 (22°C, at pH 6.9 as DCB.2HCl, quoted, Verschueren 1983) 3.11 (shake flask-UV/LSC, Banerjee et al. 1980) Vapor Pressure (Pa at 25°C): 0.00133 (estimated, Mabey et al. 1982) Henry’s Law Constant (Pa·m3/mol at 25°C): 0.0811 (calculated-P/C, Mabey et al. 1982) Octanol/Water Partition Coefficient, log KOW: 3.02 (calculated as per Leo et al.1971) 3.51 (23°C, shake flask, Banerjee et al. 1980) 3.35 (calculated-activity coeff. . from UNIFAC, Banerjee & Howard 1988) 3.51 (recommended, Sangster 1993) 3.51 (recommended, Hansch et al. 1995) Octanol/Air Partition Coefficient, log KOA: Bioconcentration Factor, log BCF: 2.70 (bluegill sunfish, Appleton & Sikka 1980) 2.97 (microorganisms-water, calculated-KOW, Mabey et al. 1982) 2.79, 2.97, 3.49 (fish, algae, activated sludge, Freitag et al. 1985) Sorption Partition Coefficient, log KOC: 3.19 (sediment-water, calculated-KOW, Mabey et al. 1982) 4.35, 3.87 (soil: quoted, calculated-MCI . and fragment contribution, Meylan et al. 1992) 3.30 (calculated-KOW, Kollig 1993) 4.35 (soil, calculated-MCI 1., Sabljic et al. 1995) H2N NH2 Cl Cl © 2006 by Taylor & Francis Group, LLC 3286 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals Environmental Fate Rate Constants, k, or Half-Lives, t.: Volatilization: Photolysis: direct aqueous photolysis rate constant k = 2.1 . 10–6 h–1 in summer at 40°N latitude (Mabey et al. 1982); both aqueous and atmospheric photolysis t. = 0.025–0.075 h, based on direct photolysis in distilled water in midday summer sunlight (Banerjee et al. 1978; Sikka et al. 1978; quoted, Callahan et al. 1979; Howard et al. 1991) and approximate winter sunlight direct photolysis half-life (Banerjee et al. 1978; Sikka et al. 1978; Lyman et al. 1982; quoted, Howard et al. 1991). Hydrolysis: Oxidation: aqueous oxidation rate constants for singlet oxygen k < 4 . 107 M–1 h–1 and for peroxy radical k < 4 . 107 M–1 h–1 at 25°C (Mabey et al. 1982); photooxidation t. = 31.2 – 1740 h in water, based on estimated rate constants for reactions with OH and RO2 radicals in water (Mill & Mabey 1985; quoted, Howard et al. 1991); photooxidation t. = 0.905 – 9.05 h in air, based on estimated rate constant for the reaction with hydroxyl radical in air (Atkinson 1987; quoted, Howard et al. 1991) Biodegradation: aqueous aerobic t. = 672 – 4320 h, based on lake die-away study test data (Appleton et al. 1978; quoted, Howard et al. 1991) and a soil die-away test (Boyd et al. 1984; quoted, Howard et al. 1991); aqueous anaerobic t. = 2688 – 17280 h, based on estimated unacclimated aqueous aerobic biodegradation half-life (Howard et al. 1991). Biotransformation: rate constant for bacterial transformation k = 3 . 10–12 mL·cell–1·h–1 in water (Mabey et al. 1982). Bioconcentration, Uptake (k1) and Elimination (k2) Rate Constants: Half-Lives in the Environment: Air: t. = 0.905 – 9.05 h, based on estimated rate constant for the reaction with hydroxyl radical in air (Atkinson 1987; quoted, Howard et al. 1991); estimated t. ~ 1 d for the reaction with hydroxyl radical and ozone (Howard 1989); atmospheric transformation lifetime by photolysis was estimated to be < 1 d (Kelly et al 1994). Surface water: t. = 0.025 – 0.075 h, based on direct photolysis in distilled water in midday summer sunlight (Banerjee et al. 1978; Sikka et al. 1978; quoted, Howard et al. 1991) and approximate winter sunlight direct photolysis half-life (Banerjee et al. 1978; Sikka et al. 1978; Lyman et al. 1982; quoted, Howard et al. 1991). Ground water: t. = 1344 – 8640 h, based on estimated unacclimated aqueous aerobic biodegradation half-life (Howard et al. 1991). Sediment: t. = 30 min by suspended microcrystalline clays may be considered the most important fate process in the aquatic environment (Callahan et al. 1979). Soil: t. = 672 – 4320 h, based on estimated unacclimated aqueous aerobic biodegradation half-life (Howard et al. 1991). Biota: © 2006 by Taylor & Francis Group, LLC Nitrogen and Sulfur Compounds 3287 16.1.3.14 N,N’-Bianiline Common Name: N,N.-Bianiline Synonym: 1,2-diphenylhydrazine, hydrazobenzene Chemical Name: 1,2-diphenylhydrazine, hydrazobenzene CAS Registry No: 122-66-7 Molecular Formula: C12H12N2, C6H5NHNHC6H5 Molecular Weight: 184.236 Melting Point (°C): 131 (Weast 1982–83; Lide 2003) Boiling Point (°C): 293 (as azobenzene, IARC 1975) Density (g/cm3 at 20°C): 1.158 (16°C, Weast 1982–83) Molar Volume (cm3/mol): 213.0 (calculated-Le Bas method at normal boiling point) Dissociation constant pKb: 13.2 (Kollig 1993) Enthalpy of Fusion, .Hfus (kJ/mol): Entropy of Fusion, .Sfus (J/mol K): Fugacity Ratio at 25°C (assuming .Sfus = 56 J/mol K), F: 0.0912 (mp at 131°C) Water Solubility (g/m3 or mg/L at 25°C): 0.252 (20°C, as azobenzene, Takagishi et al. 1968) Vapor Pressure (Pa at 25°C or as indicated and reported temperature dependence equations): 0.00347 (quoted, Mabey et al. 1982) log (P/mmHg) = 16.8982 – 5.0039 . 103/(T/K) –0.35846·log (T/K) –9.9629 . 10–3·(T/K) + 4.2938 . 10–6·(T/K)2; temp range 404–573 K (vapor pressure eq., Yaws 1994) Henry’s Law Constant (Pa·m3/mol at 25°C): 3.45 . 10–4 (calculated-P/C, Mabey et al. 1982) Octanol/Water Partition Coefficient, log KOW: 3.82 (shake flask-UV as for azobenzene, Fujita et al. 1964) 3.03 (calculated as per Leo et al. 1971, Callahan et al. 1979) 2.94 (shake flask, Hansch & Leo 1979; 1987) 2.94 (recommended, Sangster 1993) 2.94 (recommended, Hansch et al. 1995) Octanol/Air Partition Coefficient, log KOA: Bioconcentration Factor, log BCF: 2.46 (microorganisms-water, calculated-KOW, Mabey et al. 1982) Sorption Partition Coefficient, log KOC: 2.62 (sediment-water, calculated-KOW, Mabey et al. 1982) 1.40 (calculated-KOW, Kollig 1993) HN NH © 2006 by Taylor & Francis Group, LLC 3288 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals Environmental Fate Rate Constants, k, or Half-Lives, t.: Volatilization: Photolysis: Hydrolysis: Oxidation: aqueous oxidation rate constants for singlet oxygen k < 4 . 107 M–1 h–1 and for peroxy radical, k < 1 . 109 M–1 h–1 at 25°C (Mabey et al. 1982); photooxidation t. = 31 – 1740 h, based on photooxidation rate constants with OH and RO2 radicals for the amine class (Guesten et al. 1981; Mill & Mabey 1985; quoted, Howard et al. 1991); photooxidation t. = 0.3 – 3.0 h in air, based on estimated rate data for the reaction with hydroxyl radical in air (Atkinson 1987; quoted, Howard et al. 1991). Biodegradation: aqueous aerobic t. = 672 – 4320 h, based on acclimated aerobic aqueous screening test data (Malaney 1960; quoted, Howard et al. 1991); aqueous anaerobic t. = 2880 – 17280 h, based on estimated unacclimated aqueous aerobic biodegradation half-life (Howard et al. 1991). Biotransformation: bacterial transformation k = 1 . 10–10 mL·cell–1·h–1 in water (Mabey et al. 1982). Bioconcentration, Uptake (k1) and Elimination (k2) Rate Constants: Half-Lives in the Environment: Air: photooxidation t. = 0.3 – 3.0 h, based on estimated rate data for the reaction with hydroxyl radical in air (Atkinson 1987; quoted, Howard et al. 1991); atmospheric transformation lifetime was estimated to be < 1 d (Kelly et al. 1994). Surface water: photooxidation t. = 31 – 1740 h, based on photooxidation rate constants with OH and RO2 radicals for the amine class (Guesten et al. 1981; Mill & Mabey 1985; quoted, Howard et al. 1991). Groundwater: t. = 1344 – 8640 h, based on estimated unacclimated aqueous aerobic biodegradation half-life (Howard et al. 1991). Sediment: Soil: t. = 672 – 4320 h, based on estimated aqueous aerobic biodegradation half-life (Howard et al. 1991). Biota: © 2006 by Taylor & Francis Group, LLC Nitrogen and Sulfur Compounds 3289 16.1.3.15 .-Naphthylamine (1-Aminonaphthalene) Common Name: 1-Naphthylamine Synonym: 1-naphthalenamine, .-naphthylamine, 1-NA, 1-aminonaphthalene, naphthalidine Chemical Name: 1-naphthalenamine CAS Registry No: 134-32-7 Molecular Formula: C10H7NH2 Molecular Weight: 143.185 Melting Point (°C): 49.2 (Lide 2003) Boiling Point (°C): 300.7 (Lide 2003) Density (g/cm3 at 20°C): 1.1229 (25°C, Weast 1982–8) 1.123 (Dean 1985) Molar Volume (cm3/mol): 161.8 (calculated-Le Bas method at normal boiling point) Dissociation Constant pKa: 3.92 (Sangster 1993) Enthalpy of Fusion, .Hfus (kJ/mol): 14.23 ± 0.105 (Tsonopoulos & Prausnitz 1971) Entropy of Fusion, .Sfus (J/mol K): 44.35 ± 3.35 (Tsonopoulos & Prausnitz 1971) Fugacity Ratio at 25°C (assuming .Sfus = 56 J/mol K), F: 0.579 (mp at 49.2°C) Water Solubility (g/m3 or mg/L at 25°C): 1700 (Verschueren 1983) 590 parts in water (Budavari 1989) Vapor Pressure (Pa at 25°C and reported temperature dependence equations): 0.803 (extrapolated-regression of tabulated data, temp range 104.3–300.8°C, Stull 1947) log (P/mmHg) = [–0.2185 . 14529.5/(T/K)] + 8.29900; temp range 104.3–300.8°C (Antoine eq., Weast 1972–73) 0.557 (extrapolated-Cox eq., Chao et al. 1983) log (P/atm) = [1– 574.066/(T/K)] . 10^{0.822931 – 2.94554 . 10–4·(T/K) + 2.19845 . 10–7·(T/K)2}; temp range: 325.0–645.0 K (Cox eq., Chao et al. 1983) 0.446 (extrapolated, liquid, Antoine eq., Stephenson & Malanowski 1987) log (PL/kPa) = 6.88407 – 2570.55/(–46.989 + T/K); temp range 377–574 K (Antoine eq., Stephenson & Malanowski 1987) Henry’s Law Constant (Pa·m3/mol at 25°C): 6.197 (gas stripping-GC, Altschuh et al. 1999) Octanol/Water Partition Coefficient, log KOW: 2.23 (Leo et al. 1969) 2.25 (shake flask, Hansch & Leo 1979) 2.27 (shake flask-UV at pH 7.5, Martin-Villodre et al. 1986) 2.33 (HPLC-k. correlation, Minick et al. 1988) 2.25 (recommended, Sangster 1993) 2.25 (recommended, Hansch et al. 1995) 2.34 (microemulsion electrokinetic chromatography-retention factor correlation, Poole et al. 2000) NH2 © 2006 by Taylor & Francis Group, LLC 3290 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals Octanol/Air Partition Coefficient, log KOA: Bioconcentration Factor, log BCF: Sorption Partition Coefficient, log KOC: 3.58, 3.43, 3.50 (Milford soil, Morocco soil, Oakville soil, Graveel et al. 1986) 2.63, 2.68, 3.15 (sediment, Alfisol soil, Podzol soil, von Oepen et al. 1991) 3.51, 3.48 (soil, quoted exptl., calculated-MCI ., Meylan et al. 1992) 3.51 (soil, calculated-MCI 1., Sabljic et al. 1995) 2.0–2.65 (5 soils, pH 2.8–7.4, batch equilibrium-sorption isotherm, Li et al. 2000) Environmental Fate Rate Constants, k, or Half-Lives, t.: Volatilization: Photolysis: Oxidation: rate constant k = 1 . 104 M–1 s–1 for oxidation by RO2 radical at 30°C in aquatic systems with t. = 0.8 d (Howard 1972; Hendry et al. 1974; quoted, Mill 1982); rate constant k < 2 . 102 M–1 s–1 for oxidation by singlet oxygen at 25°C in aquatic systems with t. > 100 yr (Foote 1976; Mill 1979; quoted, Mill 1982); atmospheric t. = 0.292–2.92 h, based on estimated rate constants for the reaction with OH radical in air and aqueous photooxidation t. = 62.4–3480 h, based on estimated rate constants for reaction of representative aromatic amines with OH and RO2 radicals in aqueous solution (Howard et al. 1991); photooxidation t. = 0.08–0.13 h under sunlight and t. = 0.25–9.1 h under UV light when adsorbed on silica; t. = 0.10–0.15 h under sunlight and t. = 0.15–10.5 h under UV light when adsorbed on alumina on the TLC plates under simulated atmospheric conditions (Hasegawa et al. 1993). Hydrolysis: Biodegradation: aqueous aerobic biodegradation t. = 672–4320 h and aqueous anaerobic biodegradation t. = 2688–17280 h, based on slow biodegradation observed in aerobic soil die-away test study and aerobic activated sludge screening tests (Howard et al. 1991). Biotransformation: Bioconcentration, Uptake (k1) and Elimination (k2) Rate Constants: Half-Lives in the Environment: Air: t. = 0.292–2.92 h, based on estimated photooxidation half-life in air (Howard et al. 1991). Surface water: t. = 0.62.4–3840 h, based on estimated rate constants for reactions of aromatic amines with OH and RO2 radicals in aqueous solutions (Howard et al. 1991). Groundwater: t. = 1344–8640 h, based on slow biodegradation observed in an aerobic soil die-away test study and aerobic activated sludge screening tests (Howard et al. 1991). Sediment: Soil: t. = 672–4320 h, based on slow biodegradation observed in an aerobic soil die-away test study and aerobic activated sludge screening tests (Howard et al. 1991). Biota: © 2006 by Taylor & Francis Group, LLC Nitrogen and Sulfur Compounds 3291 16.1.3.16 .-Naphthylamine (2-Aminonaphthalene) Common Name: 2-Naphthylamine Synonym: 2-naphthalenamine, .-naphthylamine, 2-NA, 2-aminonaphthalene, naphthalidine Chemical Name: 2-naphthalenamine CAS Registry No: 91-59-8 Molecular Formula: C10H7NH2 Molecular Weight: 143.185 Melting Point (°C): 113 (Weast 1982–83; Lide 2003) Boiling Point (°C): 306.2 (Lide 2003) Density (g/cm3): 1.0614 (at 98°C, Weast 1982–83; Verschueren 1983; Dean 1985) Molar Volume (cm3/mol): 161.8 (calculated-Le Bas method at normal boiling point) Dissociation Constant pKa: 4.15 (Sangster 1993) Enthalpy of Fusion, .Hfus (kJ/mol): 21.97 (Tsonopoulos & Prausnitz 1971) Entropy of Fusion, .Sfus (J/mol K): 57.32 (Tsonopoulos & Prausnitz 1971) Fugacity Ratio at 25°C (assuming .Sfus = 56 J/mol K), F: 0.137 (mp at 113°C) Water Solubility (g/m3 or mg/L at 25°C or as indicated): 6.40 (18°C, Ciusa 1922; quoted, Tsonopoulos & Prausnitz 1971) 0.19 (18–20°C, Neish 1948; quoted, Tsonopoulos & Prausnitz 1971) Vapor Pressure (Pa at 25°C and reported temperature dependence equations): 0.634 (extrapolated-regression of tabulated data, temp range 108–306.1°C, Stull 1947) log (P/atm) = [–0.2185 . 14679.6/(T/K)] + 8.435133; temp range 108–306.1°C (Antoine eq., Weast 1972–73) 0.369 (extrapolated-Cox eq., Chao et al. 1983) log (P/atm) = [1 – 579.422/(T/K)] . 10^{0.860256 – 4.44286 . 10–4·(T/K) + 3.71453 . 10–7·(T/K)2}; temp range: 385.0–645.0 K (Cox eq., Chao et al. 1983) 0.035 (Howard et al. 1986) 0.035 (interpolated, solid, Antoine eq., Stephenson & Malanowski 1987) 0.362 (extrapolated, liquid, Antoine eq., Stephenson & Malanowski 1987) log (PS/kPa) = 8.4859 – 3859/(T/K), temp range: 283–323 K, (Antoine eq.-I, Stephenson & Malanowski 1987) log (PL/kPa) = 6.88978 – 2604.31/(–46.068 + T/K), temp range 388–579 K (Antoine eq.-II, Stephenson & Malanowski 1987) 0.340 (calculated-solvatochromic parameters, Banerjee et al. 1990) Henry’s Law Constant (Pa·m3/mol at 25°C): Octanol/Water Partition Coefficient, log KOW: 2.28 (shake flask, Hansch & Leo 1979) 2.26 (20°C, shake flask, Korenman & Polumestnaya, 1982) 2.40 (calculated-UNIFAC activity coeff., Campbell & Luthy 1985) 2.40 (shake flask-AS, pH 7.5, Martin-Villodre et al. 1986) 2.34 (recommended, Sangster 1993) 2.28 (recommended, Hansch et al. 1995) NH2 © 2006 by Taylor & Francis Group, LLC 3292 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals Octanol/Air Partition Coefficient, log KOA: Bioconcentration Factor, log BCF: Sorption Partition Coefficient, log KOC: 1.77 (calculated-KOW, Kollig 1993) Environmental Fate Rate Constants, k, or Half-Lives, t.: Volatilization: Photolysis: Oxidation: rate constant k = 1 . 104 M–1 s–1 for oxidation by RO2 radicals at 30°C in aquatic systems with t. = 0.8 d (Howard 1972; Hendry et al. 1974; quoted, Mill 1982); rate constant k < 2 . 102 M–1 s–1 for oxidation by singlet oxygen at 25°C in aquatic systems with t. > 100 yr (Foote 1976; Mill 1979; quoted, Mill 1982); photooxidation t. = 0.30–2.90 h in air, based on estimated rate constant for the vapor-phase reaction with hydroxyl radical in air (Atkinson 1987; quoted, Howard et al. 1991); aqueous photooxidation t. = 62–3480 h, based on estimated rate constants for reaction of representative aromatic amines with OH and RO2 radicals in aqueous solution (Guesten et al. 1981; Mill & Mabey 1985; quoted, Howard et al. 1991); photooxidation t. = 0.05–0.14 h under sunlight and 0.20–10.0 h under UV light when adsorbed on silica and t. = 0.16–0.19 h under sunlight and t. = 0.22–10.8 h under UV light when adsorbed on alumina TLC plates under simulated atmospheric conditions (Hasegawa et al. 1993). Hydrolysis: Biodegradation: aqueous aerobic biodegradation t. = 672–4320 h, based on unacclimated aerobic screening test data (Fochtman & Eisenberg 1979; quoted, Howard et al. 1979) and unacclimated soil grab sample data (Medvedev & Davidov 1981; quoted, Howard et al. 1991); aqueous anaerobic biodegradation t. = 2880–17280 h, based on estimated unacclimated aqueous aerobic biodegradation half-life (Howard et al. 1991). Biotransformation: Bioconcentration, Uptake (k1) and Elimination (k2) Rate Constants: Half-Lives in the Environment: Air: photooxidation t. = 0.30–2.90 h, based on estimated rate constant for the vapor-phase reaction with hydroxyl radical in air (Atkinson 1987; quoted, Howard et al. 1991). Surface water: t. = 62.0–3840 h, based on estimated rate constants for reactions of aromatic amines with OH and RO2 radicals in aqueous solutions (Guesten et al. 1981; Mill & Mabey 1985; quoted, Howard et al. 1991). Groundwater: t. = 1344–8640 h, based on estimated unacclimated aqueous aerobic biodegradation half-life (Howard et al. 1991). Sediment: Soil: t. = 672–4320 h, based on unacclimated aerobic screening test data (Fochtman & Eisenberg 1979; quoted, Howard et al. 1991) and unacclimated aerobic soil grab sample data (Medvedev & Davidov 1981; quoted, Howard et al. 1981). Biota: © 2006 by Taylor & Francis Group, LLC Nitrogen and Sulfur Compounds 3293 16.1.3.17 2-Nitroaniline Common Name: 2-Nitroaniline Synonym: 1-amino-2-nitrobenzene, o-aminonitrobenzene, o-nitroaniline, 2-nitrophenylamine, 2-nitrobenzeneamine Chemical Name: 1-amino-2-nitrobenzene, o-nitroaniline, 2-nitroaniline CAS Registry No: 88-74-4 Molecular Formula: C6H6N2O2, C6H4NH2NO2 Molecular Weight: 138.124 Melting Point (°C): 71.0 (Lide 2003) Boiling Point (°C): 284 (Lide 2003) Density (g/cm3 at 20°C): 1.442 (15°C, Weast 1982–83; Verschueren 1983; Dean 1985) Molar Volume (cm3/mol): 138.7 (calculated-Le Bas method at normal boiling point) Dissociation Constant, pKa: Enthalpy of Fusion, .Hfus (kJ/mol): 16.11 (Tsonopoulos & Prausnitz 1971) Entropy of Fusion, .Sfus (J/mol K): 46.86 (Tsonopoulos & Prausnitz 1971) Fugacity Ratio at 25°C (assuming .Sfus = 56 J/mol K), F: 0.354 (mp at 71.0°C) Water Solubility (g/m3 or mg/L at 25°C or as indicted): 1212, 2423 (25, 40°C, synthetic method-shake flask-titration, Collet & Johnson 1926) 1740 (calculated-KOW, Yalkowsky & Morozowich 1980) 1260 (Verschueren 1983) Vapor Pressure (Pa at 25°C and reported temperature dependence equations): log (P/mmHg) = 8.81842 – 3336.52/(T/K); measured range 150–215°C (isoteniscope, Berliner & May 1925) log (P/mmHg) = 9.55950 – 4037.7/(T/K); measured range 190–250°C (isoteniscope, Berliner & May 1925) 0.620 (extrapolated-regression of tabulated data, temp range 104–284.5°C, Stull 1947) 0.072 (Knudsen method, calculated-Antoine eq., Hoyer & Peperle 1958) log (P/mmHg) = 12.50 – 4701/(T/K), temp range 0–50°C (Knudsen effusion method, Hoyer & Peperle 1958) log (P/mmHg) = [–0.2185 . 15284.0/(T/K)] + 8.868383; temp range 104–284.5°C (Antoine eq., Weast 1972–73) < 13.3 (30°C, Verschueren 1983) 0.650 (extrapolated-Antoine eq., Dean 1985, 1992) log (P/mmHg) = 8.8684 – 3336.5/(T/K); temp range 150–260°C (Antoine eq., Dean 1985, 1992) log (PS/kPa) = 11.625 – 4701/(T/K); temp range 273–323 K (Antoine eq.-I, Stephenson & Malanowski 1987) log (PL/kPa) = 11.3629 – 7444.3/(240.83 + T/K); temp range 423–553 K (Antoine eq.-II, Stephenson & Malanowski 1987) log (P/mmHg) = –112.5774 –1.5945 . 103/(T/K) + 54.577·log (T/K) –7.6775 . 10–2·(T/K) + 3.6152 . 10–5·(T/K)2; temp range 345–558 K (vapor pressure eq., Yaws 1994) Henry’s Law Constant (Pa·m3/mol): Octanol/Water Partition Coefficient, log KOW: 1.44 (shake flask-UV, Fujita et al. 1964) 1.83 (shake flask-UV, Hansch & Anderson 1967) 1.62 (HPLC-RT correlation, Carlson et al. 1975) 1.81 (Hansch & Leo 1979) NH2 NO2 © 2006 by Taylor & Francis Group, LLC 3294 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals 1.72 (shake flask, Eadsforth & Moser 1983) 1.67 (calculated-HPLC-k. correlation, Deneer et al. 1987) 1.50 (calculated-linear extrapolation exptl. log k at various solvent compositions, Deneer et al. 1987) 1.93, 1.73 (25°C, 60°C, shake flask-UV, Kramer & Henze 1990) 1.85 (recommended, Sangster 1993) 1.80 ± 0.14, 1.35 ± 0.51 (solvent generated liquid-liquid chromatography SGLLC-correlation, RP-HPLC-k. correlation, Cichna et al. 1995) 1.85 (recommended, Hansch et al. 1995) Octanol/Air Partition Coefficient, log KOA: Bioconcentration Factor, log BCF: 0.91; 1.49, 0.55, 0.83 (quoted exptl.; calculated values-KOW, Bintein et al. 1993) Sorption Partition Coefficient, log KOC: Environmental Fate Rate Constants, k, or Half-Lives, t.: Half-Lives in the Environment: Surface water: estimated t. = 1.4 d in Rhine River in case of a first order reduction process (Zoeteman et al. 1980) © 2006 by Taylor & Francis Group, LLC Nitrogen and Sulfur Compounds 3295 16.1.3.18 4-Nitroaniline Common Name: 4-Nitroaniline Synonym: 1-amino-4-nitrobenzene, p-aminonitrobenzene, p-nitroaniline, 4-nitrobenzenamine, 4-nitrophenylamine Chemical Name: 1-amino-4-nitrobenzene, p-nitroaniline, 4-nitroaniline CAS Registry No: 100-01-6 Molecular Formula: C6H6N2O2, C6H4NH2NO2 Molecular Weight: 138.124 Melting Point (°C): 147.5 (Lide 2003) Boiling Point (°C): 332 (Lide 2003) Density (g/cm3 at 20°C): 1.424 (Weast 1982–83; Verschueren 1983) 1.4370 (14°C, Dean 1985) Molar Volume (cm3/mol): 138.7 (calculated-Le Bas method at normal boiling point) Dissociation Constant, pKa: Enthalpy of Fusion, .Hfus (kJ/mol): 21.09 (Tsonopoulos & Prausnitz 1971) Entropy of Fusion, .Sfus (J/mol K): 50.21 (Tsonopoulos & Prausnitz 1971) Fugacity Ratio at 25°C (assuming .Sfus = 56 J/mol K), F: 0.0628 (mp at 147.5°C) Water Solubility (g/m3 or mg/L at 25°C or as indicated): 568, 1157 (25, 40°C, synthetic method-shake flask-titration, Collet & Johnson 1926) 728 (30°C, shake flask-interferometry, Gross et al. 1931) 603 (calculated-KOW, Yalkowsky & Morozowich 1980) 380 (20°C, shake flask-membrane filter-fluorophotometry, Hashimoto et al. 1982) 390, 400 (20°C, shake flask-glass fiber filters-fluorophotometry, Hashimoto et al. 1982) 800; 22000 (19°C, 100°C, Verschueren 1983) 800 (Dean 1985) Vapor Pressure (Pa at 25°C and reported temperature dependence equations): log (P/mmHg) = 9.55950 – 4037.7/(T/K); measured range 190–250°C (isoteniscope, Berliner & May 1925) 0.035 (extrapolated-regression of tabulated data, temp range 142.4–336°C, Stull 1947) log (P/mmHg) = 13.69 – 5707/(T/K), temp range 30–90°C, (Knudsen effusion method, Hoyer & Peperle 1958) log (P/mmHg) = [–0.2185 . 17220.2/(T/K)] + 9.041879; temp range 142.4–336°C (Antoine eq., Weast 1972–73) 0.200, 0.933 (20°C, 30°C, Verschueren 1983) 0.014 (extrapolated-Antoine eq., Dean 1985) log (P/mmHg) = 9.5595 – 4039.73/(T/K); temp range 190–260°C (Antoine eq., Dean 1985, 1992) log (PS/kPa) = 11.1109 – 5093/(T/K); temp range 346–366 K (solid, Antoine eq.-I, Stephenson & Malanowski 1987) log (PL/kPa) = 8.7988 – 4071.3/(T/K); temp range 473–538 K (liquid, Antoine eq.-II., Stephenson & Malanowski 1987) log (P/mmHg) = 56.1642 – 5.3655 . 103/(T/K) –17.958·log (T/K) + 9.092 . 10–3·(T/K) + 7.0305 . 10–10·(T/K)2; temp range 421–609 K (vapor pressure eq., Yaws 1994) NH2 NO2 © 2006 by Taylor & Francis Group, LLC 3296 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals Henry’s Law Constant (Pa·m3/mol): Octanol/Water Partition Coefficient, log KOW: 1.39 (shake flask-UV, Fujita et al. 1964; Hansch & Leo 1979) 0.59 (calculated-activity coeff. . from UNIFAC, Campbell & Luthy 1985) 1.16 (HPLC-k. correlation, Deneer et al. 1987) 1.10 (calculated-linear extrapolation exptl. values of log k at various solvent compositions, Deneer et al. 1987) 1.15 (HPLC-RT correlation, Wang et al. 1989) 1.51, 1.36 (25°C, 60°C, shake flask-UV, Kramer & Henze 1990) 1.30 (CPC-RV correlation, Tsai et al. 1991) 1.30 (CPC-RV correlation, El Tayar et al. 1991) 1.35 (recommended, Sangster 1993) 1.39 ± 0.14, 0.75 ± 0.48 (solvent generated liquid-liquid chromatography SGLLC-correlation, RP-HPLC-k. correlation, Cichna et al. 1995) 1.37 (recommended, Hansch et al. 1995) Octanol/Air Partition Coefficient, log KOA: Bioconcentration Factor, log BCF: Sorption Partition Coefficient, log KOC: 2.26; 2.66; 2.12 (Alfisol soil; Podzol soil; sediment, von Oepen et al. 1991) 0.64; 1.25, –0.18, 0.41 (quoted exptl.; calculated values-KOW, Bintein et al. 1993) 2.16, 2.22, 2.19 (RP-HPLC-k. correlation on 3 different stationary phases, Szabo et al. 1995) 1.86, 1.84 (RP-HPLC-k. correlation including MCI related to non-dispersive intermolecular interactions, hydrogen- bonding indicator variable, Hong et al. 1996) Environmental Fate Rate Constants, k, or Half-Lives, t.: Half-Lives in the Environment: Surface water: estimated t. = 2.3 d in Rhine River in case of a first order reduction process (Zoeteman et al. 1980) © 2006 by Taylor & Francis Group, LLC Nitrogen and Sulfur Compounds 3297 16.1.4 NITROAROMATIC COMPOUNDS 16.1.4.1 Nitrobenzene Common Name: Nitrobenzene Synonym: nitrobenzol, oil of mirbane Chemical Name: nitrobenzene CAS Registry No: 98-95-3 Molecular Formula: C6H5NO2 Molecular Weight: 123.110 Melting Point (°C): 5.7 (Stull 1947; Dreisbach 1955; Weast 1982–83; Howard 1989; Lide 2003) Boiling Point (°C): 210.8 (Weast 1982–83; Lide 2003) Density (g/cm3 at 20°C): 1.2032, 1.1982 (20°C, 25°C, Dreisbach 1955) 1.2036 (20°C, Weast 1982–83) Molar Volume (cm3/mol): 102.0 (calculated from density, Rohrschneider 1973; Chiou 1985) 112.0 (calculated-Le Bas method at normal boiling point) Dissociation Constant pKa: Enthalpy of Vaporization, .HV (kJ/mol): 55.186, 43.421 (25°C, bp, Dreisbach 1961) 55.013, 40.769 (25°C, bp, Riddick et al. 1986) Enthalpy of Fusion, .Hfus (kJ/mol): 11.59 (Dreisbach 1955) 12.13 (Tsonopoulos & Prausnitz 1971) 11.63 (Riddick et al. 1986) Entropy of Fusion, .Sfus (J/mol K): 43.51 (Tsonopoulos & Prausnitz 1971) Fugacity Ratio at 25°C (assuming .Sfus = 56 J/mol K), F: 1.0 Water Solubility (g/m3 or mg/L at 25°C or as indicated. Additional data at other temperatures designated * are compiled at the end of this section): 1780, 2050 (15, 30°C, shake flask-interferometry, Gross et al. 1931) 2060* (30°C, shake flask-interferometry and titration, measured range 0–60°C, Vermillion et al. 1941) 1204 (shake flask-centrifuge, Booth & Everson 1948) 1930 (Seidell 1941) 2018 (shake flask-interferometry, Donahue & Bartell 1952) 1950 (Deno & Berkheimer 1960) 2259 (35°C, shake flask-UV spectrophotometry, Hine et al. 1963) 2060 (Hansch et al. 1968) 1900 (20°C, Verschueren 1977, 1983) 2093 (shake flask-LSC, Banerjee et al. 1980) 2090 (shake flask-radioactive analysis, Veith et al. 1980) 2043 (20–27°C, shake flask-GC, Chiou 1985) 1900 (20°C, Riddick et al. 1986; quoted, Howard 1989) 1930* (20°C, shake flask-UV spectrophotometry, measured range 10–40°C, Benes & Dohnal 1999) NO2 © 2006 by Taylor & Francis Group, LLC 3298 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals Vapor Pressure (Pa at 25°C or as indicated and reported temperature dependence equations. Additional data at other temperatures designated * are compiled at the end of this section): 133.3* (53.1°C, static-manometer, measured range 53.1–208.3°C, Kahlbaum 1898) 38.80 (saturated vapor density-gas saturation, Puck & Wise 1946) 42.06* (extrapolated-regression of tabulated data, temp range 44.4–210.6°C, Stull 1947) 10063* (134.1°C, ebulliometry, measured range 134.1–210.629°C, Brown 1952) 37.86 (calculated by formula, Dreisbach 1955; quoted, Hine & Mookerjee 1975) log (P/mmHg) = 7.08283 – 1722.2/(199.0 + t/°C); temp range 108–300°C (Antoine eq. for liquid state, Dreisbach 1955) 32.3* (23.14°C, gas saturation, measured range 6.09–23.14°C, Lynch & Wilke 1960) log (P/mmHg) = 7.545 – 2064/(t/°C + 230); temp range 6.09–23.14°C (gas saturation, Lynch & Wilke 1960) 80.0 (35°C, gas saturation-gravitational or UV spectrophotometry, Hine et al. 1963) log (P/mmHg) = [–0.2185 . 12168.2/(T/K)] + 8.416268; temp range 44.4–210.6°C (Antoine eq., Weast 1972–73) 34.60 (extrapolated-Antoine eq., Boublik et al. 1973) log (P/mmHg) = 7.11562 – 1746.585/(201.783 + t/°C), temp range 134–210.6°C (Antoine eq. from reported exptl. data, Boublik et al. 1973) 20.00 (20°C, Verschueren 1977, 1983) 28.37 (calculated-bp, Mackay et al. 1982) 34.36 (extrapolated-Antoine eq., Boublik et al. 1984) log (P/kPa) = 6.23424 – 1741.779/(201.257 + t/°C); temp range 134–210.6°C (Antoine eq. from reported exptl. data, Boublik et al. 1984) log (P/kPa) = 4.06596 – 323.457/(–58.276 + t/°C); temp range 239–291°C (Antoine eq. from reported exptl. data, Boublik et al. 1984) 34.63 (extrapolated-Antoine eq., Dean 1985; 1992) log (P/mmHg) = 6.91048 – 946.35/(246.68 + t/°C); temp range –87 to 7°C (Antoine eq., Dean 1985, 1992) 37.0 (quoted lit., Riddick et al. 1986) log (P/kPa) = 6.670 – 2064.0/(230.0 + t/°C), temp range not specified (Antoine eq., Riddick et al. 1986) 37.65 (extrapolated-Antoine eq.-II, Stephenson & Malanowski 1987) log (PL/kPa) = 6.22069 – 1732.222/(–72.886 + T/K); temp range 407–484 K (Antoine eq.-I, Stephenson & Malanowski 1987) log (PL/kPa) = 6.6699 – 2064/(–43.15 + T/K); temp range 279–296 K (Antoine eq.-II, Stephenson & Malanowski 1987) 33.33 (Howard et al. 1986) log (P/mmHg) = –54.4937 –2.1123 . 103/(T/K) + 29.321·log (T/K) –4.4839 . 10–2·(T/K) + 2.0162 . 10–5·(T/K)2; temp range 279–719 K (vapor pressure eq., Yaws 1994) Henry’s Law Constant (Pa·m3/mol at 25°C): 2.367, 4.51, 4.723 (exptl., calculated-group contribution, calculated-bond contribution, Hine & Mookerjee 1975) 1.327 (calculated-P/C, Mabey et al. 1982) 2.472 (estimated, Lyman et al. 1982) 5.06 (calculated-molecular structure, Russell et al. 1992) 0.868 (gas stripping-GC, Altschuh et al. 1999) Octanol/Water Partition Coefficient, log KOW: 1.85 (shake flask-UV, Fujita et al. 1964; Hansch et al. 1968; Leo et al. 1969, 1971; Hansch & Leo 1979, 1985;) 1.74 (Neely et al. 1974) 1.85, 1.84 (Hansch & Leo 1979) 1.82 (HPLC-RT correlation, Veith et al. 1979a) 1.83 (shake flask-LSC, Banerjee et al. 1980) 1.98, 1.78 (HPLC-k. correlation, McDuffie 1981) 1.85 (generator column-HPLC, Wasik et al. 1981; Tewari et al. 1982;) 1.88 (shake flask-UV, Unger & Chiang 1981) 1.99 (RP-HPLC-k. correlation, Miyake & Terada 1982) 1.83, 1.84 (calculated-activity coeff. . from UNIFAC, octanol and water solubility considered; calculatedactivity coeff. . from UNIFAC, octanol and water solubility not considered, Arbuckle 1983) 1.85, 1.88 (lit. values, Verschueren 1983) © 2006 by Taylor & Francis Group, LLC Nitrogen and Sulfur Compounds 3299 1.83 ± 0.02 (HPLC-RV correlation-ALPM, Garst & Wilson 1984) 1.84 (calculated-activity coefficient . from UNIFAC, Campbell & Luthy 1985) 1.87 (Lu et al. 1986) 1.85 (RP-HPLC-k. correlation, Minick et al. 1988) 1.89 (HPLC-k. correlation, Deneer et al. 1987) 1.84 (calculated-activity coeff. . from UNIFAC, Banerjee & Howard 1988) 1.70 (RP-HPLC-RT correlation, ODS column with masking agent, Bechalany et al. 1989) 1.828 ± 0.001 (shake flask/slow-stirring-GC, De Bruijn et al. 1989) 1.85 (recommended, Sangster 1989, 1993) 1.836 ± 0.051; 1.828 ± 0.001 (average values, stir-flask method by BRE; by RITOX, Brooke et al. 1990) 1.83, 1.85, 1.88 (CPC-retention volume correlation; Gluck & Martin 1990) 1.94, 2.25 (25°C, 60°C, shake flask-UV, Kramer & Henze 1990) 1.57 (shake flask-UV, Nakagawa et al. 1992) 1.85 (shake flask-GC, Alcron et al. 1993) 1.85 (recommended, Hansch et al. 1995) 2.25, 2.12, 2.20, 2.23 (HPLC-k. correlation, different combinations of stationary and mobile phases under isocratic conditions, Makovskaya et al. 1995) 1.88 (shake flask-dialysis tubing-HPLC/UV, both phases, Andersson & Schrader 1999) 1.93 (microemulsion electrokinetic chromatography-retention factor correlation, Poole et al. 2000) Octanol/Air Partition Coefficient, log KOA: Bioconcentration Factor, log BCF: 1.18 (fathead minnows, Veith et al. 1979b) 0.06 (calculated-KOW, Veith et al. 1980) < 1.0; 1.36 (golden orfe; green algae, Freitag et al. 1982) 1.38; 1.42 (alga Chlorella fusca, wet wt. basis; calculated-KOW, Geyer et al. 1984) 0.78 (P. reticulata, Canton et al. 1985; quoted, Howard 1989) < 1.0, 1.38, 1.60 (golden orfe, algae, activated sludge, Freitag et al. 1982) < 1.0, 1.30, 1.60 (golden ide, algae, activated sludge, Freitag et al. 1985) 1.47 ± 0.12 (guppy-fat wt. basis, Deneer et al. 1987) Sorption Partition Coefficient, log KOC: 1.94 (20°C, sorption isotherm-GC, converted from KOM multiplied by 1.724, Briggs 1981) 2.30 (Lincoln fine sand, calculated exptl. value, Wilson et al. 1981) 2.23, 2.57 (Danish subsoils, Loekke 1985) 1.63, 1.84 (two Norwegian organic soils, Seip et al. 1986) 1.70 (soil, quoted, Sabljic 1987) 1.95 ± 0.84, 2.02 ± 1.18; 1.99 (Captina slit loam, McLaurin sandy loam; weighted mean, batch equilibriumsorption isotherm, Walton et al. 1992) 1.43 (predicted-KOW, Walton et al. 1992) 1.51 (calculated-KOW, Kollig 1993) 2.20 (soil, calculated-QSAR MCI 1., Sabljic et al. 1995) 2.05, 2.16, 2.15 (RP-HPLC-k. correlation on 3 different stationary phases, Szabo et al. 1995) 1.99, 1.84 (RP-HPLC-k. correlation including MCI related to non-dispersive intermolecular interactions, hydrogen-bonding indicator variable, Hong et al. 1996) 2.20; 2.28 (HPLC-screening method; calculated-PCKOC fragment method, Muller & Kordel 1996) 2.51, 2.03, 2.26, 2.09, 1.90 (soil: calculated-KOW; HPLC-screening method using LC-columns of different stationary phases, Szabo et al. 1999) Environmental Fate Rate Constants, k, or Half-Lives, t.: Volatilization: t.(calc) . 200 h from water bodies (Mackay & Leinonen 1975; quoted, Callahan et al. 1979) t. = 45 d was estimated in a model river 1 m deep with a 1.0 m/s current and a 3 m/s wind (Lyman et al. 1982; quoted, Howard 1989). © 2006 by Taylor & Francis Group, LLC 3300 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals Photolysis: aqueous photolysis t. = 67–200 d, based on measured photolysis rate constant in distilled water under midday sun at 40°N latitude (Simmons & Zepp 1986; Howard 1989; Howard et al. 1991); atmospheric photolysis t. = 67–200 d, based on measured photolysis rate constant in distilled water under midday sun at 40°N latitude (Simmons & Zepp 1986; quoted, Howard 1989; Howard et al. 1991); rate constant k = 2.37 . 10–3 h–1 with H2O2 under photolysis at 25°C in F-113 solution and with HO- in the gas (Dilling et al. 1988). Hydrolysis: Oxidation: rate constant k, for gas-phase second order rate constants, kOH for reaction with OH radical, kNO3 with NO3 radical and kO3 with O3 or as indicated *data at other temperatures see reference: photooxidation t. = 125 d to 22 yr in water, based on measured rate constant for reaction with hydroxyl radical in water (Dorfman & Adams 1973; Anbar & Neta 1967; quoted, Howard et al. 1991) k << 360 M–1 h–1 for singlet oxygen, k << 1.0 M–1 h–1 for peroxy radical at 25°C (Mabey et al. 1982) k = (0.09 ± 0.02) M–1 s–1 for 5–10 mM to react with ozone in water using 50–1000 mM of t-BuOH as scavenger at pH 2 and 20–23°C (Hoigne & Bader 1983) kOH(obs.) = 0.15 . 10–12 cm3 molecule–1 s–1 at 296 K (Becker et al. 1984; quoted, Carlier et al. 1986) kOH = 0.21 . 10–12 cm3 molecule–1 s–1 at room temp. (Zetzsch 1982) kOH(calc) = 0.30 . 10–12 cm3 molecule–1 s–1 and 0.27 . 10–12 cm3 molecule–1 s–1 at room temp. (Atkinson 1985; Atkinson et al. 1985) kOH* = 0.137 . 10–12 cm3 molecule–1 s–1 at 299 K, measured range 259–362 K (flash photolysis-resonance fluorescence, Witte et al. 1986) kOH(calc) = 1.1 . 10–13 cm3 molecule–1 s–1, 1.7 . 10–13 cm3 molecule–1 s–1 (addition of OH for different positions of the electrophilic attack, Witte et al. 1986) kO3 < 7 . 10–21 cm3 molecule–1 s–1 at 296 ± 2 K (relative rate method, Atkinson et al. 1987) kOH = 1.3 . 10–13 cm3 molecule–1 s–1 with atmospheric lifetimes . = 180 d in clean troposphere and 90 d in moderately polluted atmosphere; kO3 < 7 . 10–21 cm3 molecule–1 s–1 with atmospheric lifetimes . > 6 yr in clean troposphere and . > 2 yr in moderately polluted atmosphere at room temp. (Atkinson et al. 1987) kOH(calc) = 2.5 . 10–13 cm3·molecule–1 s–1, kOH(obs.) = 1.4 . 10–13 cm3·molecule–1 s–1 (SAR structure-activity relationship, Atkinson 1987) kOH = (0.16 – < 0.90) . 10–12 cm3 molecule–1 s–1 at 296 K (review, Atkinson 1989) phototransformation decay rate constant of 0.17 min–1 on 0.20 g/L of TiO2, 8.8 min–1 on 0.20 g/L of ZnO and 3.1 min–1 on 1.0 g/L of Al2O3 (Minero et al. 1994) Abiotic Transformation: Degradation in reductive environment: k = 0.187 min–1 with solute concn of 50 µM in a 19 day-old 0.2g/L magnetite suspension at pH 7 and 1.5 mM Fe(II) at 25°C (Klusen et al. 1995) k = (7.39 ± 1.28) . 10–2 M–1 s–1 in H2S with (mercapto)juglone (an abiotic reductant found in natural systems) solution at pH 6.65 (Wang & Arnold 2003) Biodegradation: decomposition by a soil microflora in more than 64 d (Alexander & Lustigman 1966; quoted, Verschueren 1983) t.(aq. anaerobic) = 48–300 h, based on anaerobic natural die-away test data for 2,4-dinitrotoluene (Spanggord et al. 1980; quoted, Howard et al. 1991) k = 14 mg COD g–1 h–1 average biodegradation rate for 98% removal (Scow 1982) t.(aq. aerobic) = 322–4728 h, based on aerobic soil column biodegradation study data (Kincannon & Lin 1985; quoted, Howard et al. 1991) t.(aerobic) = 13 d, t.(anaerobic) = 2 d in natural waters (Capel & Larson 1995) Biotransformation: first-order rate constant of 0.7 d–1 corresponding to a half-life of 1 d in adopted activated sludge under aerobic conditions (Mills et al. 1982); rate constant for bacterial transformation of 3 . 10–9 mL cell–1 h–1 in water (Mabey et al. 1982). Bioconcentration, Uptake (k1) and Elimination (k2) Rate Constants: Half-Lives in the Environment: Air: atmospheric lifetimes: . = 180 d in clean troposphere and . = 90 d in moderately polluted atmosphere, based on gas-phase reaction with OH radical in atmosphere at room temp. and atmospheric lifetimes . > 6 yr in clean troposphere and . > 2 yr in moderately polluted atmosphere, based on gas-phase reaction with O3 (estimated rate constant) in atmosphere at room temp. (Atkinson et al. 1987); © 2006 by Taylor & Francis Group, LLC Nitrogen and Sulfur Compounds 3301 photooxidation t. = 0.544 – 5.44 h, based on measured rate constant for reaction with hydroxyl radical in air (Atkinson et al. 1987; quoted, Howard 1989; Howard et al. 1991); atmospheric transformation lifetime was estimated to be > 5 d (Kelly et al. 1994). Surface water: photooxidation t. = 125 d to 22 yr, based on measured rate constant for reaction with hydroxyl radical in water (Dorfman & Adams 1973; Anbar & Neta 1967; quoted, Howard et al. 1991); estimated t. = 0.3 – 3.0 d in rivers (Zoeteman et al. 1980); t. = 322 – 4728 h, based on estimated unacclimated aqueous aerobic biodegradation half-life (Howard et al. 1991) t.(aerobic) = 13 d, t.(anaerobic) = 2 d in natural waters (Capel & Larson 1995). Groundwater: estimated t. = 1.0 d in Rhine River in case of a first order reduction process (Zoeteman et al. 1980) t. = 48 – 9456 h, based on estimated unacclimated aqueous anaerobic biodegradation half-life for 2,4- dinitrotoluene and estimated unacclimated aqueous aerobic biodegradation half-life (Howard et al. 1991). Sediment: Soil: estimated degradation t. = 625 d in activated sludge (Freitag et al. 1985; quoted, Anderson et al. 1991) t. = 322 – 4728 h, based on aerobic soil column biodegradation study data (Kincannon & Lin 1985; quoted, Howard et al. 1991); calculated t. = 9.1 d from first-order kinetic of degradation rate in sterilized soils (Anderson et al. 1991). Biota: TABLE 16.1.4.1.1 Reported aqueous solubilities of nitrobenzene at various temperatures Gross et al. 1931 Vermillion et al. 1941 Benes & Dohnal 1999 shake flask-interferometry interferometry shake flask-UV t/°C S/g·m–3 t/°C S/g·m–3 t/°C S/g·m–3 15 1780 0 1660 10 1770 30 2050 6 1700 20 1930 30 2060 30 2060 60 3120 40 2200 titration .Hsol/(kJ mol–1) =5.4 ± 0.2 30 2060 at 25°C. 50 2640 FIGURE 16.1.4.1.1 Logarithm of mole fraction solubility (ln x) versus reciprocal temperature for nitrobenzene. Nitrobenzene: solubility vs. 1/T -9.0 -8.5 -8.0 -7.5 -7.0 0.0028 0.003 0.0032 0.0034 0.0036 0.0038 1/(T/K) x nl Gross et al. 1931 Vermillion et al. 1941 Benes & Dohnal 1999 © 2006 by Taylor & Francis Group, LLC 3302 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals TABLE 16.1.4.1.2 Reported vapor pressures of nitrobenzene at various temperatures and the coefficients for the vapor pressure equations log P = A – B/(T/K) (1) ln P = A – B/(T/K) (1a) log P = A – B/(C + t/°C) (2) ln P = A – B/(C + t/°C) (2a) log P = A – B/(C + T/K) (3) log P = A – B/(T/K) – C·log (T/K) (4) Kahlbaum 1898* Stull 1947 Lynch & Wilke 1960 Brown 1952 static-manometer summary of literature data gas saturation ebulliometry t/°C P/Pa t/°C P/Pa t/°C P/Pa t/°C P/Pa 53.1 133.3 44.4 133.3 6.09 8.799 134.1 10063 59.8 266.6 71.6 666.6 12.57 14.80 139.75 13372 64.9 400.0 84.9 1333 12.67 13.33 143.17 16084 69.2 533.3 99.3 2666 14.67 16.93 149.73 18692 72.9 666.6 115.4 5333 14.72 17.73 154.61 21866 85.4 1333.2 125.8 7999 21.37 29.06 159.77 25704 99.1 2666.4 139.9 13332 21.54 29.33 164.45 29641 108.2 3999.7 161.2 26664 23.12 32.26 168.72 33649 114.9 5332.9 185.8 53329 23.14 32.26 172.96 38002 120.0 6666.1 210.6 101325 176.48 44455 131.1 9999.2 bp/°C 210.8 182.07 49014 139.9 13332 mp/°C 5.7 185.70 54019 160.5 26664 eq. 2 P/mmHg 188.90 58839 174.5 39997 A 7.545 196.63 65426 184.5 53329 B 2064 200.41 71843 192.5 66661 C 230 203.88 78997 199.5 79993 206.62 86075 205.0 93326 209.49 92023 208.3 101325 210.626 101322 210.629 101330 *complete list see ref. © 2006 by Taylor & Francis Group, LLC Nitrogen and Sulfur Compounds 3303 FIGURE 16.1.4.1.2 Logarithm of vapor pressure versus reciprocal temperature for nitrobenzene. Nitrobenzene: vapor pressure vs. 1/T 0.0 1.0 2.0 3.0 4.0 5.0 6.0 7.0 8.0 0.0018 0.0022 0.0026 0.003 0.0034 0.0038 0.0042 1/(T/K) P( gol S ) aP/ Kahlbaum 1898 Brown 1952 Lynch & Wilke 1960 Stull 1947 b.p. = 210.8 °C m.p. = 5.7 °C © 2006 by Taylor & Francis Group, LLC 3304 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals 16.1.4.2 2-Nitrotoluene Common Name: 2-Nitrotoluene Synonym: 1-methyl-2-nitrobenzene, o-nitrotoluene, 2-methylnitrobenzene Chemical Name: 2-nitrotoluene, o-nitrotoluene CAS Registry No: 88-72-2 Molecular Formula: C7H7NO2, CH3C6H4NO2 Molecular Weight: 137.137 Melting Point (°C): –10.4 (Lide 2003) Boiling Point (°C): 222 (Lide 2003) Density (g/cm3 at 20°C): 1.15693, 1.15232 (20°C, 25°C, Dreisbach & Martin 1949) 1.1629 (Weast 1982–83) Molar Volume (cm3/mol): 117.9 (20°C, Stephenson & Malanowski 1987) 153.0 (calculated-Le Bas method at normal boiling point) Dissociation Constant pKa: Enthalpy of Fusion, .Hfus (kJ/mol): Entropy of Fusion, .Sfus (J/mol K): Fugacity Ratio at 25°C (assuming .Sfus = 56 J/mol K), F: 1.0 Water Solubility (g/m3 or mg/L at 25°C. Additional data at other temperatures designated * are compiled at the end of this section): 652 (30°C, shake flask-interferometer, Gross et al. 1933) 656 (quoted, Deno & Berkheimer 1960) < 233 (shake flask-centrifuge, Booth & Everson 1948) 324 (Hansch et al. 1968) 656, 2076 (quoted, predicted-KOW, Valvani et al. 1981) 652 (30°C, Verschueren 1983) 656, 771 (quoted, calculated-fragment const., Wakita et al. 1986) 641; 444 (quoted exptl.; calculated-group contribution method, Kuhne et al. 1995) 609* (20°C, shake flask-UV spectrophotometry, measured range 10–40°C, Benes & Dohnal 1999) Vapor Pressure (Pa at 25°C and reported temperature dependence equations. Additional data at other temperatures designated * are compiled at the end of this section): 23.97* (extrapolated-regression of tabulated data, Kahlbaum 1898) 27.69* (extrapolated-regression of tabulated data, temp range 50–222.3°C, Stull 1947) log (P/mmHg) = 7.49454 – 2086.1/(230 + t/°C) (Antoine eq., Dreisbach & Martin 1949) 3640* (115.842°C, ebulliometry, measured range 115.842–174.744°C, Dreisbach & Shrader 1949) log (P/mmHg) = [–0.2185 . 12239.7/(T/K)] + 8.286642; temp range 50–222.3°C (Antoine eq., Weast 1972–73) 13.33 (20°C, Verschueren 1983) 1.670 (extrapolated-Antoine eq., Boublik et al. 1984) log (P/kPa) = 5.01415 – 967.744/(99.208 + t/°C); temp range 129.31–222.2°C (Antoine eq. from reported exptl. data, Boublik et al. 1984) 1.440 (extrapolated-Antoine eq., Dean 1985, 1992) log (P/mmHg) = 5.851 – 946/(96 + t/°C), temp range 129–222°C (Antoine eq., Dean 1985, 1992) log (PL/kPa) = 6.32043 – 1827.66/(–71.63 + T/K); temp range 402–496 K (Antoine eq., Stephenson & Malanowski 1987) NO2 © 2006 by Taylor & Francis Group, LLC Nitrogen and Sulfur Compounds 3305 24.80* (ebulliometry, average from extrapolated-Antoine eq., Aim 1994) log (P/mmHg) = 7.8266 – 2.9906 . 103/(T/K) + 1.1064·log (T/K) – 4.9168 . 10–3·(T/K) + 2.2375 . 10–6·(T/K)2; temp range 270–720 K (vapor pressure eq., Yaws 1994) Henry’s Law Constant (Pa·m3/mol at 25°C): 5.811 (exptl., Hine & Mookerjee 1975) 4.723, 4.616 (calculated-group contribution, calculated-bond contribution, Hine & Mookerjee 1975) Octanol/Water Partition Coefficient, log KOW: 2.30 (Leo et al. 1971; Hansch & Leo 1985) 2.30 (HPLC-k. correlation, Deneer et al. 1987) 2.30 (unpublished data quoted from CLOGP Database and recommended, Sangster 1989) 2.39, 2.43, 2.58 (CPC-RV correlation, Gluck & Martin 1990) 2.46, 2.60; 2.30 (25°C, 60°C, shake flask-UV; quoted lit. value, Kramer & Henze 1990) 2.13 (shake flask-UV, Nakagawa et al. 1992) 2.30 (recommended, Sangster 1993) 2.40 ± 0.15, 2.21 ± 0.53 (solvent generated liquid-liquid chromatography SGLLC-correlation, RP-HPLC-k. correlation, Cichna et al. 1995) 2.30 (recommended, Hansch et al. 1995) Octanol/Air Partition Coefficient, log KOA: Bioconcentration Factor, log BCF: < 2.0 (carprinus carpio, Sasaki 1978; Kawasaki 1980) 1.52, 1.20 (calculated-KOW, S, Lyman et al. 1982; quoted, Howard 1989) 2.28 ± 0.06 (guppy-fat basis, Deneer et al. 1987) Sorption Partition Coefficient, log KOC: 2.63, 2.09 (soil, calculated-KOW, S, Lyman et al. 1982; quoted, Howard 1989) Environmental Fate Rate Constants, k, or Half-Lives, t.: Volatilization: estimated t. = 21 h using Henry’s law constant for a model river 1-m deep flowing 1 m/s with a wind speed of 3 m/s (Lyman et al. 1982; quoted, Howard 1989). Photolysis: Oxidation: rate constant k =3.0 . 10–11 cm3 molecules–1 s–1 for the reaction with 8 . 10–5 molecules/cm3 photochemically produced hydroxyl radical in air (GEMS 1986; quoted, Howard 1989); rate constant k = 7.0 . 10–11 cm3 molecule–1 s–1 for the gas-phase reactions with OH radical at 298 K (Atkinson 1989). Hydrolysis: Abiotic Transformation: Degradation in reductive environment: k = 0.141 min–1 with solute concn of 50 µM in a 19 day-old 0.2g/L magnetite suspension at pH 7 and 1.5 mM Fe(II) at 25°C (Klusen et al. 1995) Biodegradation: average biodegradation rate of 32.5 mg COD g–1 h–1 for 98% removal (Scow 1982). Biotransformation: Bioconcentration, Uptake (k1) and Elimination (k2) Rate Constants: Half-Lives in the Environment: Air: t. = 8 h, based on a rate constant k = 3.0 . 10–11 cm3 molecules–1 s–1 for the reaction with 8 . 10–5 molecules/cm3 photochemically produced hydroxyl radical in air (GEMS 1986; quoted, Howard 1989). Surface water: estimated t. = 3.2 d in Rhine River in case of a first order reduction process (Zoeteman et al. 1980) midday t.(calc) = 45 min in Aucilla River water due to indirect photolysis using an experimentally determined reaction rate constant k = 0.92 h–1 (Zepp et al. 1984; quoted, Howard 1989); estimated t. = 3.2 d for a river 4 to 5 m deep, based on monitoring data (Zoeteman et al. 1980; quoted, Howard 1989). Ground water: Sediment: Soil: Biota: © 2006 by Taylor & Francis Group, LLC 3306 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals TABLE 16.1.4.2.1 Reported aqueous solubilities of 2-nitrotoluene at various temperatures Gross et al. 1931 Benes & Dohnal 1999 shake flask-interferometry shake flask-UV t/°C S/g·m–3 t/°C S/g·m–3 15 - 10 531 30 652 20 609 30 688 40 773 .Hsol/(kJ mol–1) = 9.4 ± 0.1 25°C FIGURE 16.1.4.2.1 Logarithm of mole fraction solubility (ln x) versus reciprocal temperature for 2-nitrotoluene. TABLE 16.1.4.2.2 Reported vapor pressures of 2-nitrotoluene at various temperatures and the coefficients for the vapor pressure equations log P = A – B/(T/K) (1) ln P = A – B/(T/K) (1a) log P = A – B/(C + t/°C) (2) ln P = A – B/(C + t/°C) (2a) log P = A – B/(C + T/K) (3) log P = A – B/(T/K) – C·log (T/K) (4) Kahlbaum 1898 Stull 1947 Dreisbach & Shrader 1949 Aim 1994 static method summary of literature data ebulliometry comparative ebulliometry t/°C P/Pa t/°C P/Pa t/°C P/Pa t/°C P/Pa 81.8 666.6 50.0 133.3 129.31 6287 115.842 3640 94.8 1333.2 79.1 666.6 134.51 7605 115.847 3639 109.6 2666.4 93.8 1333 138.75 8851 127.245 5773 114.8 3333.1 109.6 2666 142.43 10114 127.268 5778 2-Nitrotoluene: solubility vs. 1/T -10.0 -9.5 -9.0 -8.5 -8.0 0.0028 0.003 0.0032 0.0034 0.0036 0.0038 1/(T/K) x nl Benes & Dohnal 1999 Gross et al. 1931 © 2006 by Taylor & Francis Group, LLC Nitrogen and Sulfur Compounds 3307 TABLE 16.1.4.2.2 (Continued) Kahlbaum 1898 Stull 1947 Dreisbach & Shrader 1949 Aim 1994 static method summary of literature data ebulliometry comparative ebulliometry t/°C P/Pa t/°C P/Pa t/°C P/Pa t/°C P/Pa 119.2 3999.7 126.3 5333 156.61 16500 137.028 8376 122.8 4666.3 137.6 7999 185.48 42077 137.052 8375 126.1 5333 151.5 13332 205.48 67661 144.838 11104 131.7 6666 173.7 26664 222.15 101325 151.379 13955 150.6 13332 197.7 53329 151.415 13946 172.4 26664 222.3 101325 bp/°C 222.15 157.004 16843 186.1 39997 157.028 16827 196.0 53329 mp/°C –4.1 162.792 20322 204.2 66661 162.840 20311 211.3 79993 168.856 24597 217.5 93326 168.917 24587 220.4 101325 174.744 29405 mp/°C –2.90 bp/°C 222.946 eq. 3 P/kPa A 6.45342 B 1906.532 C 65.441 for temp range: 115–175°C FIGURE 16.1.4.2.2 Logarithm of vapor pressure versus reciprocal temperature for 2-nitrotoluene. 2-Nitrotoluene: vapor pressure vs. 1/T 0.0 1.0 2.0 3.0 4.0 5.0 6.0 7.0 8.0 0.0018 0.0022 0.0026 0.003 0.0034 0.0038 0.0042 1/(T/K) P( gol S ) aP/ Kahlbaum 1898 Dreisbach & Shrader 1949 Aim 1994 Stull 1947 b.p. = 222 °C m.p. = -10.4 °C © 2006 by Taylor & Francis Group, LLC 3308 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals 16.1.4.3 4-Nitrotoluene Common Name: 4-Nitrotoluene Synonym: 1-methyl-4-nitrobenzene, p-nitrotoluene, 4-methylnitrobenzene Chemical Name: 4-nitrotoluene, p-nitrotoluene CAS Registry No: 99-99-0 Molecular Formula: CH3C6H4NO2 Molecular Weight: 137.137 Melting Point (°C): 51.63 (Lide 2003) Boiling Point (°C): 238.3 (Stull 1947; Weast 1982–83; Dean 1985; Howard 1989) Density (g/cm3 at 20°C): 1.16278, 1.15799 (20°C, 25°C, Dreisbach & Martin 1949) 1.392 (Dean 1985) Molar Volume (cm3/mol): 124.2 (75°C, Stephenson & Malanowski 1987) 153.0 (calculated-Le Bas method at normal boiling point) Dissociation Constant, pK: –11.27 (Perrin 1972) Enthalpy of Fusion, .Hfus (kJ/mol): 17.15 (Tsonopoulos & Prausnitz 1971) Entropy of Fusion, .Sfus (J/mol K): 50.21 (Tsonopoulos & Prausnitz 1971) Fugacity Ratio at 25°C (assuming .Sfus = 56 J/mol K), F: 0.548 (mp at 51.63°C) Water Solubility (g/m3 or mg/L at 25°C or as indicated. Additional data at other temperatures designated * are compiled at the end of this section): 442 (30°C, shake flask-interferometer, Gross et al. 1933) < 278 (shake flask-centrifuge, Booth & Everson 1948) 302 (Tsonopoulos & Prausnitz 1971) 442 (30°C, Verschueren 1983) 288 (20°C, shake flask-UV spectrophotometry, Hashimoto et al. 1984) 307 (calculated-group contribution method, Kuhne et al. 1995) 242* (20°C, shake flask-UV spectrophotometry, measured range 10–40°C, Benes & Dohnal 1999) Vapor Pressure (Pa at 25°C or as indicated and reported temperature dependence equations. Additional data at other temperatures designated * are compiled at the end of this section): 13.98* (extrapolated-regression of tabulated data, measured range 92–237°C, Kahlbaum 1898) log (P/mmHg) = –2630/(T/K) + 8.025 (isoteniscope method, temp range not specified, Kobe et al. 1941) 22.81* (extrapolated-regression of tabulated data, temp range 53.7–238.2°C, Stull 1947) log (P/mmHg) = 7.52323 – 2150.6/(230 + t/°C) (Antoine eq., Dreisbach & Martin 1949) 8851* (147.71°C, ebulliometry, measured range 147.71–233.25°C, Dreisbach & Shrader 1949) 0.622* (23.886°C, Knudsen effusion, measured range 297.036–309.518 K, Lenchitz & Velicky 1970) log (P/mmHg) = 11.5424 – 4130.0708/(T/K); temp range 297–310 K (Knudsen effusion, Lenchitz & Velicky 1970) log (P/mmHg) = [–0.2185 . 11915.0/(T/K)] + 7.965025; temp range 53.7–238.3°C (Antoine eq., Weast 1972–73) 5.50* (ebulliometry, fitted to Antoine eq., measured range 144–239°C, Ambrose & Gundry 1980) 9.50 (extrapolated-supercooled liq., Ambrose & Gundry 1980) NO2 © 2006 by Taylor & Francis Group, LLC Nitrogen and Sulfur Compounds 3309 13.33 (20°C, Verschueren 1983; quoted, Howard 1989) 8.347 (extrapolated-Antoine eq., Boublik et al. 1984) log (P/kPa) = 6.11507 – 1716.897/(184.543 + t/°C); temp range 147.7–233.3°C (Antoine eq. from reported exptl. data, Boublik et al. 1984) 8.38 (extrapolated-Antoine eq., Dean 1985, 1992) log (P/mmHg) = 6.9948 – 1720.39/(184.9 + t/°C); temp range 148–233°C (Antoine eq., Dean l985, 1992) 0.653 (interpolated-Antoine eq.-I, Stephenson & Malanowski 1987) log (PS/kPa) = 10.6673 – 4130.07/(T/K); temp range 296–310 K (solid, Antoine eq.-I, Stephenson & Malanowski 1987) log (PL/kPa) = 7.40605 – 2889.12/(23.37 + T/K); temp range 423–512 K (liquid, Antoine eq.-II, Stephenson & Malanowski 1987) 15.18* (ebulliometry, average of extrapolated-Antoine eq., Aim 1994) log (P/mmHg) = 9.9641 – 2.6549 . 103/(T/K) – 0.80182·log (T/K) + 5.3926 . 10–4·(T/K) – 4.109 . 10–14·(T/K)2; temp range 325–736 K (vapor pressure eq., Yaws 1994) Henry’s Law Constant (Pa·m3/mol at 25°C): 5.065 (calculated, Hine & Mookerjee 1975) Octanol/Water Partition Coefficient, log KOW: 2.37 (shake flask-UV, Fujita et al. 1964) 2.40 (unpublished result, Leo et al. 1971) 2.34 (HPLC-k. correlation, Deneer et al. 1987) 2.42 (recommended, Sangster 1989) 2.10, 2.05 (25°C, 60°C, shake flask-UV, Kramer & Henze 1990) 2.61 (shake flask-UV, Nakagawa et al. 1992) 2.37 (recommended, Sangster 1993) 2.37 ± 0.15 (solvent generated liquid-liquid chromatography SGLLC-correlation, Cichna et al. 1995) 2.42 (recommended, Hansch et al. 1995) 2.18 (microemulsion electrokinetic chromatography-retention factor correlation, Poole et al. 2000) Octanol/Air Partition Coefficient, log KOA: Bioconcentration Factor, log BCF: < 2.0 (Carprinus carpio, Sasaki 1978; Kawasaki 1980) 1.57, 1.30 (calculated-KOW, S, Lyman et al. 1982; quoted, Howard 1989) 2.37 ± 0.05 (guppy-fat basis, Deneer et al. 1987) Sorption Partition Coefficient, log KOC: 2.67, 2.18 (soil, calculated-KOW, S, Lyman et al. 1982; quoted, Howard 1989) Environmental Fate Rate Constants, k, or Half-Lives, t.: Volatilization: based on Henry’s law constant an estimated t. = 25 h was obtained for a model river of 1- m deep with a current of 1 m/s and wind speed of 3 m/s (Lyman et al. 1982; quoted, Howard 1989). Photolysis: Oxidation: photooxidation t. = 8.0 h in air, based on measured rate constant k = 3 . 10–11 cm3 molecule–1 s–1 at 25°C for the reaction with photochemically produced 8 . 105 molecules/cm3 hydroxyl radical (GEMS 1986; quoted, Howard 1989). Hydrolysis: Abiotic Transformation: Degradation in reductive environment: k = 0.101 min–1 with solute concn of 50 µM in a 19 d-old 0.2g/L magnetite suspension at pH 7 and 1.5 mM Fe(II) at 25°C (Klusen et al. 1995) Biodegradation: average biodegradation rate of 32.5 mg COD g–1 h–1 for 98% removal (Scow 1982). Biotransformation: Bioconcentration, Uptake (k1) and Elimination (k2) Rate Constants: © 2006 by Taylor & Francis Group, LLC 3310 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals Half-Lives in the Environment: Air: photooxidation t. = 8.0 h, based on measured rate constant of 3 . 10–11 cm3 molecule–1 s–1 at 25°C for the reaction with photochemically produced 8 . 105 molecules/cm3 hydroxyl radical (GEMS 1986; quoted, Howard 1989). Surface water: estimated t. = 2.7 d in Rhine River in case of a first order reduction process (Zoeteman et al. 1980) estimated t. = 2.7 d, based on monitoring data for a river of 4 to 5-m deep (Zoeteman et al. 1980; quoted, Howard 1989). Groundwater: Sediment: Soil: Biota: TABLE 16.1.4.3.1 Reported aqueous solubilities of 4-nitrotoluene at various temperatures Gross et al. 1931 Benes & Dohnal 1999 shake flask-interferometry shake flask-UV t/°C S/g·m–3 t/°C S/g·m–3 15 - 10 179 30 442 20 242 30 322 40 418 .Hsol/(kJ mol–1) = 21.1 ± 0.1 25°C FIGURE 16.1.4.3.1 Logarithm of mole fraction solubility (ln x) versus reciprocal temperature for 4-nitrotoluene. 4-Nitrotoluene: solubility vs. 1/T -11.0 -10.5 -10.0 -9.5 -9.0 0.0028 0.003 0.0032 0.0034 0.0036 0.0038 1/(T/K) x nl Benes & Dohnal 1999 Gross et al. 1931 © 2006 by Taylor & Francis Group, LLC Nitrogen and Sulfur Compounds 3311 TABLE 16.1.4.3.2 Reported vapor pressures of 4-nitrotoluene at various temperatures and the coefficients for the vapor pressure equations log P = A – B/(T/K) (1) ln P = A – B/(T/K) (1a) log P = A – B/(C + t/°C) (2) ln P = A – B/(C + t/°C) (2a) log P = A – B/(C + T/K) (3) log P = A – B/(T/K) – C·log (T/K) (4) 1. Kahlbaum 1898 Stull 1947 Dreisbach & Shrader 1949 Lenchitz & Velicky 1970 static method-manometer summary of literature data ebulliometry Knudsen effusion t/°C P/Pa t/°C P/Pa t/°C P/Pa t/°C P/Pa 92.3 666.6 53.7 133.3 147.71 8851 23.886 0.6218 105.6 1333.2 85.0 666.6 151.43 10114 23.888 0.6283 120.3 2666.4 100.5 1333 165.98 16500 26.042 0.7311 125.7 3333 117.7 2666 197.75 42077 26.06 0.7330 130.4 3999.7 136.0 5333 216.17 67661 28.029 0.9426 134.4 4666 147.9 7999 233.25 101325 28.065 0.8994 137.9 5333 163.0 13332 30.205 1.0348 143.8 6666 186.7 26664 bp/°C 233.25 30.207 1.0423 164.0 13332 212.5 53329 32.012 1.3291 186.5 26664 238.3 101325 32.033 1.2987 201.2 39997 34.16 1.6681 212.2 53329 mp/°C 51.9 34.165 1.6551 220.8 66661 35.348 2.3313 228.4 79993 35.358 2.2839 234.8 93326 36.368 2.3087 237.7 101325 mp/°C 51.5 enthalpy of sublimation: .Hsub = 43.095 kJ mol–1 at 25°C eq. 1 P/mmHg A 11.5424 B 4130.0828 2. Ambrose & Gundry 1980 Aim 1994 bubble-cap ebulliometer comparative ebulliometry t/°C P/Pa t/°C P/Pa 143.498 5649 128.161 3639 148.11 7742 128.167 3639 153.159 9254 140.078 5776 158.081 10956 140.132 5787 163.205 12999 150.293 8378 168.438 15403 150.369 8400 173.494 18066 158.455 11107 180.103 22110 158.487 11118 185.757 26135 165.32 13946 (Continued) © 2006 by Taylor & Francis Group, LLC 3312 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals TABLE 16.1.4.3.2 (Continued) Ambrose & Gundry 1980 Aim 1994 bubble-cap ebulliometer comparative ebulliometry t/°C P/Pa t/°C P/Pa 192.227 31460 165.32 13967 198.564 37505 171.181 16823 205.643 44864 171.225 16845 212.568 54256 171.236 16848 218.948 63659 177.246 20306 225.722 75033 177.30 20332 233.058 89121 183.698 24639 238.685 101268 239.269 102565 mp/°C 51.5 bp/°C 238.343 tp/°C 51.64 bp/°C 238.675 eq. 2 P/kPa .Hfus = 16.81 kJ mol–1 A 6.36793 .HV = 46.60 kJ mol–1, at bp B 1931.718 C 68.661 eq. 3 P/kPa for temp range: 128–184°C A 6.27217 B 1682,295 C –75.321 for temp range: 416 to 513 K vapor pressure eq. for solid: eq. 1 P/kPa A 32.2514 B 9018.0 at triple pt P = 67.72 Pa at 298.15 K P = 5.5Pa FIGURE 16.1.4.3.2 Logarithm of vapor pressure versus reciprocal temperature for 4-nitrotoluene. 4-Nitrotoluene: vapor pressure vs. 1/T -1.0 0.0 1.0 2.0 3.0 4.0 5.0 6.0 7.0 0.0018 0.0022 0.0026 0.003 0.0034 0.0038 1/(T/K) P( gol S ) aP/ experimental data Lenchitz & Velicky 1970 Stull 1947 b.p. = 238.3 °C m.p. = 51.63 °C © 2006 by Taylor & Francis Group, LLC Nitrogen and Sulfur Compounds 3313 16.1.4.4 2,4-Dinitrotoluene (DNT) Common Name: 2,4-Dinitrotoluene Synonym: dinitrotoluol, 1-methyl-2,4-dinitrobenzene, DNT Chemical Name: 2,4-dinitrotoluene, 1-methyl-2,4-dinitrobenzene CAS Registry No: 121-14-2 Molecular Formula: C7H6N2O4, CH3C6H3(NO2)2 Molecular Weight: 182.134 Melting Point (°C): 70.5 (Lide 2003) Boiling Point (°C): 300 dec. (Weast 1982–83; Lide 2003) Density (g/cm3 at 20°C): 1.521 (15°C, Verschueren 1983) Molar Volume (cm3/mol): 175.2 (calculated-Le Bas method at normal boiling point) Dissociation Constant, pK: –13.53 (Perrin 1972) Enthalpy of Fusion, .Hfus (kJ/mol): Entropy of Fusion, .Sfus (J/mol K): 58.99 (Yalkowsky & Valvani 1980) Fugacity Ratio at 25°C (assuming .Sfus = 56 J/mol K), F: 0.358 (mp at 70.5°C) Water Solubility (g/m3 or mg/L at 25°C or as indicated and reported temperature dependence equations. Additional data at other temperatures designated * are compiled at the end of this section): 270 (22°C, Verschueren 1977, 1983) 300 (22°C, Dunlap 1981) 276; 145 (quoted exptl.; calculated-group contribution method, Kuhne et al. 1995) 199 (25.2°C, shake flask-HPLC/UV, Phelan & Barnett 2001) 188* (22°C, shake flask-HPLC/UV, measured range 12.4–61.8°C, Phelan & Barnett 2001) Vapor Pressure (Pa at 25°C and reported temperature dependence equations. Additional data at other temperatures designated * are compiled at the end of this section): 0.133* (59°C, Knudsen effusion, measured range 59–69°C, Lenchitz & Velicky 1970) 0.00321 (extrapolated-Antoine eq., Lenchitz & Velicky 1970) log (P/mmHg) = 12.6177 – 5139.058/(T/K); temp range 331.913–342.277 K (Knudsen effusion, Lenchitz & Velicky 1970) 0.0177* (20°C, gas saturation-GC/ECD, measured range 277.5–344.15 K, Pella 1977) 0.0290 (gas saturation-GC/ECD, interpolated-Antoine eq., measured range 277.5–344.15 K Pella 1977) log (P/mmHg) = (13.08 ± 0.19) – (4992 ± 59)/(T/K); temp range 277.5–344.15 K (gas saturation, Pella 1977) 0.0147 (20°C, Spanggord et al. 1980) 0.6800 (quoted, Mabey et al. 1982) log (P/kPa) = 5.06336 – 1216.523/(76.54 + t/°C); temp range 100–199°C (Antoine eq. from reported exptl. data, Boublik et al. 1984) 0.0296, 0.0032 (extrapolated-Antoine eq.-I, eq.-II, Stephenson & Malanowski 1987) log (PS/kPa) = 12.27361 – 5009.432/(T/K); temp range 277–343 K (solid, Antoine eq.-I, Stephenson & Malanowski 1987) log (PS/kPa) = 11.7426 – 5139.058/(T/K); temp range 331–342 K (solid, Antoine eq.-II, Stephenson & Malanowski 1987) NO2 NO2 © 2006 by Taylor & Francis Group, LLC 3314 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals log (PL/kPa) = 7.1423 – 3039/(T/K); temp range 473–572 K (liquid, Antoine eq.-III, Stephenson & Malanowski 1987) log (PL/kPa) = 6.04898 – 1956.095/(–108.183 + T/K); temp range 344–572 K (liquid, Antoine eq.-IV, Stephenson & Malanowski 1987) log (P/mmHg) = 5.798 – 1118/(61.8 + t/°C); temp range 200–299°C (Antoine eq., Dean 1992) log (P/mmHg) = 11.5966 – 3.0079 . 103/(T/K) –1.6468·log (T/K) + 1.5949 . 10–3·(T/K) – 1.8722 . 10–14·(T/K)2; temp range 343–814 K (vapor pressure eq., Yaws 1994) Henry’s Law Constant (Pa·m3/mol at 25°C): 0.0160 (calculated-P/C, Smith et al. 1981) 0.4560 (calculated-P/C, Mabey et al. 1982) 0.0878 (Smith et al. 1983; quoted, Howard 1989) 32.23 (quoted from WERL Treatability database, Ryan et al. 1988) Octanol/Water Partition Coefficient, log KOW: 1.98 (shake flask, Hansch & Leo 1985) 2.04 (HPLC-k. correlation, Deneer et al. 1987) 1.98 (recommended, Sangster 1993) 1.98 (recommended, Hansch et al. 1995) Octanol/Air Partition Coefficient, log KOA: Bioconcentration Factor, log BCF: 1.59 (microorganisms-water, calculated-KOW, Mabey et al. 1982) 1.11, 1.76 (daphnia magna, lumbriculus variegatus, Liu et al. 1983) > 3.30 (selanastrum capricornutum, Liu et al. 1983) 1.89, 0.602 (bluegill sunfish in viscera, bluegill sunfish in muscle, Liu et al. 1983) 2.31 ± 0.03 (guppy-fat basis, Deneer et al. 1987) Sorption Partition Coefficient, log KOC: 1.65 (sediment-water, calculated-KOW, Mabey et al. 1982) 1.68 (calculated-KOW, Kollig 1993) Environmental Fate Rate Constants, k, or Half-Lives, t.: Volatilization: half-life of approximately 100 d (Mills et al. 1982). Photolysis: direct photolysis rate constant k = 1.6 . 10–2 h–1 for summer at 40°N latitude in water (Mabey et al. 1982); aqueous photolysis t. = 23–72 h, based on measured photolysis rates in water (Mill & Mabey 1985; Simmons & Zepp 1986; quoted, Howard et al. 1991); atmospheric transformation lifetime . ~ 1–5 d (Kelly et al. 1994). Hydrolysis: Oxidation: aqueous oxidation rate constants k << 360 M–1 h–1 for singlet oxygen and k = 144 M–1 h–1 for peroxy radical at 25°C (Mabey et al. 1982); photooxidation t. = 284 – 2840 h in air, based on estimated rate constant for the reaction with hydroxyl radical in air (Atkinson 1987; quoted, Howard et al. 1991); photooxidation t. = 3–33 h, based on measured photooxidation rates in natural waters (Spanggord et al. 1980; Simmons & Zepp 1986; quoted, Howard et al. 1991). Biodegradation: aqueous anaerobic t. = 48–240 h, based on anaerobic natural water die-away test data (Spanggord et al. 1980; quoted, Howard et al. 1991); aqueous aerobic t. = 672–4320 h, based on aerobic natural water die-away test data (Spanggord et al. 1981; quoted, Howard et al. 1991). Biotransformation: rate constant of 1 . 10–7 mL cell–1 h–1 for bacterial transformation in water (Mabey et al. 1982). Bioconcentration, Uptake (k1) and Elimination (k2) Rate Constants: © 2006 by Taylor & Francis Group, LLC Nitrogen and Sulfur Compounds 3315 Half-Lives in the Environment: Air: photooxidation t. = 284–2840 h, based on estimated rate constant for the reaction with hydroxyl radical in air (Atkinson 1987; quoted, Howard et al. 1991); atmospheric transformation lifetime . ~ 1–5 d (Kelly et al. 1994). Surface water: photooxidation t. = 3–33 h, based on measured photooxidation rates in natural waters (Spanggord et al. 1980; Simmons & Zepp 1986; quoted, Howard et al. 1991); estimated t. = 1.7 d in Rhine River in case of a first order reduction process (Zoeteman et al. 1980) sunlight photolysis t. ~ 42 h in pure water but ranged from 3 h to 10 h in three natural waters (Mabey et al. 1982). Groundwater: t. = 48 – 8640 h, based on estimated unacclimated aqueous anaerobic and aerobic biodegradation half-life (Howard et al. 1991). Sediment: Soil: t. = 672 – 4320 h, based on estimated unacclimated aqueous aerobic biodegradation half-life (Howard et al. 1991). Biota: TABLE 16.1.4.4.1 Reported aqueous solubilities and vapor pressures of 2,4-dinitrotoluene at various temperatures and the coefficients for the vapor pressure equations log P = A – B/(T/K) (1) ln P = A – B/(T/K) (1a) log P = A – B/(C + t/°C) (2) ln P = A – B/(C + t/°C) (2a) log P = A – B/(C + T/K) (3) log P = A – B/(T/K) – C·log (T/K) (4) Aqueous solubility Vapor pressure Phelan & Barnett 2001 Lenchitz & Velicky 1970 Pella 1977 shake flask-HPLC/UV Knudsen effusion gas saturation-GC t/°C S/g·m–3 t/°C P/Pa t/°C P/Pa 12.4 129 58.765 0.1731 4.0 0.00164 22.0 188 59.927 0.2073 10.0 0.0038 21.7 182 59.927 0.2138 20.0 0.0177 32.0 269 60.883 0.2328 30.0 0.0453 42.0 410 62.926 0.2568 40.0 0.171 51.0 608 62.824 0.3192 50.0 0.695 61.8 975 64.002 0.3450 60.0 1.663 41.2 397 65.115 0.3836 71.0 5.295 25.2 199 67.023 0.4380 68.10 0.4952 mp/°C 69.75–70.95 69.127 0.5202 eq. 1 P/mmHg mp/°C 71.1 A 13.08 B 4992 enthalpy of sublimation: .Hsubl = 98.324 kJ mol–1 enthalpy of sublimation: (at 25°C) .Hsubl = 95.81 kJ mol–1 eq. 1 P/mmHg A 12.6177 B 5139.058 © 2006 by Taylor & Francis Group, LLC 3316 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals FIGURE 16.1.4.4.1 Logarithm of vapor pressure versus reciprocal temperature for 2,4-dinitrotoluene. 2,4-Dinitrotoluene: vapor pressure vs. 1/T -4.0 -3.0 -2.0 -1.0 0.0 1.0 2.0 3.0 4.0 0.0028 0.003 0.0032 0.0034 0.0036 0.0038 1/(T/K) P( gol S ) aP/ Lenchitz & Velicky 1970 Pella 1977 m.p. = 70.5 °C © 2006 by Taylor & Francis Group, LLC Nitrogen and Sulfur Compounds 3317 16.1.4.5 2,6-Dinitrotoluene Common Name: 2,6-Dinitrotoluene Synonym: dinitrotoluol, 1-methyl-2,6-dinitrobenzene, 2-methyl-1,3-dinitrobenzene Chemical Name: 2,6-dinitrotoluene, 1-methyl-2,6-dinitrobenzene CAS Registry No: 606-20-2 Molecular Formula: C7H6N2O4, CH3C6H3(NO2)2 Molecular Weight: 182.134 Melting Point (°C): 66.0 (Weast 1982–83; Howard 1989; Lide 2003) Boiling Point (°C): 285 (Verschueren 1977; Callahan et al. 1979; Howard 1989; Lide 2003) Density (g/cm3 at 20°C): 1.2833 (111°C, Weast 1982–83; Dean 1985) Molar Volume (cm3/mol): 141.9 (111°C, Stephenson & Malanowski 1987) 175.2 (calculated-Le Bas method at normal boiling point) Dissociation Constant pKa: Enthalpy of Fusion, .Hfus (kJ/mol): Entropy of Fusion, .Sfus (J/mol K): Fugacity Ratio at 25°C (assuming .Sfus = 56 J/mol K), F: 0.396 (mp at 66.0°C) Water Solubility (g/m3 or mg/L at 25°C or as indicated.): 180 (20°C, estimated, Mabey et al. 1982) 300 (selected, Mills et al. 1982) 182; 155 (quoted exptl.; calculated-group contribution method, Kuhne et al. 1995) Vapor Pressure (Pa at 25°C and reported temperature dependence equations. Additional data at other temperatures designated * are compiled at the end of this section): 2.40 (29°C, Mabey et al. 1982) 0.0756* (gas saturation-GC/ECD, fitted to Antoine eq., temp range 277.5–323.15 K, Pella 1977) log (P/mmHg) = (13.99 ± 0.18) – (5139 ± 52)/(T/K), temp range 277.5–323.15 K (gas saturation, Pella 1977) 0.0756 (Howard et al. 1986; quoted, Banerjee et al. 1990) 0.0767 (interpolated-Antoine eq.-I, Stephenson & Malanowski 1987) log (PS/kPa) = 11.9436 – 4446.22/(–21.279 + T/K); temp range 277–323 K (solid, Antoine eq.-I, Stephenson & Malanowski 1987) log (PL/kPa) = 7.329 – 2971/(T/K); temp range 423–523 K (liquid, Antoine eq.-II, Stephenson & Malanowski 1987) log (PL/kPa) = 6.70024 – 2160.968/(–93.282 + T/K); temp range 330–533 K (liquid, Antoine eq.-III, Stephenson & Malanowski 1987) 0.0756, 1.008 (quoted, calculated-solvatochromic parameters, Banerjee et al. 1990) log (P/mmHg) = 4.372 – 380/(–43.6 + t/°C); temp range 150–260°C (Antoine eq., Dean 1992) log (P/mmHg) = –14.5673 – 4.2746 . 103/(T/K) + 12.904·log (T/K) – 2.380 . 10–2·(T/K) + 9.4513 . 10–6·(T/K)2; temp range 339–770 K (vapor pressure eq., Yaws 1994) Henry’s Law Constant (Pa·m3/mol at 25°C) 0.800 (calculated-P/C, Mabey et al. 1982) 32.23 (quoted from WERL Treatability database, Ryan et al. 1988) 0.022 (SOGC 1987; quoted, Howard 1989) NO2 O2N © 2006 by Taylor & Francis Group, LLC 3318 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals Octanol/Water Partition Coefficient, log KOW: 1.72 (shake flask, Hansch & Leo 1985) 2.02 (HPLC-k. correlation, Deneer et al. 1987) 2.02 (shake flask-HPLC, Leggett et al. 1992) 2.07 (shake flask-UV, Nakagawa et al. 1992) 2.06 (recommended, Sangster 1993) 2.10 (recommended, Hansch et al. 1995) Octanol/Air Partition Coefficient, log KOA: Bioconcentration Factor, log BCF: 3.72 (algal biomass, Davis et al. 1981) 1.71 (microorganisms-water, calculated-KOW, Mabey et al. 1982) 1.08 (calculated-KOW, Lyman et al. 1982; quoted, Howard 1989) 2.44 ± 0.04 (guppy-fat basis, Deneer et al. 1987) Sorption Partition Coefficient, log KOC: 1.96 (sediment-water, calculated-KOW, Mabey et al. 1982) 2.31 (soil, calculated-KOW, Lyman et al. 1982; quoted, Howard 1989) 1.40 (calculated-KOW, Kollig 1993) Environmental Fate Rate Constants, k, or Half-Lives, t.: Volatilization: t. ~ 100 d (Mills et al. 1982). Photolysis: aqueous photolysis t. = 17–25 h, based on measured photolysis rates in water (Simmons & Zepp 1986; Mill & Mabey 1985; quoted, Howard et al. 1991) 89% was photo-transformed in 24 h and none left after 72 h from seawater solution under UV light (Nipper et al. 2004). Hydrolysis: Oxidation: aqueous oxidation rate constants k << 360 M–1 ± h 1 for singlet oxygen and k = 144 M–1 h–1 for peroxy radical at 25°C (Mabey et al. 1982); photooxidation t. = 2–17 h in water, based on measured photooxidation rates in natural waters (Simmons & Zepp 1986; quoted, Howard et al. 1991); photooxidation t. = 284–2840 h, based on estimated rate constant for the reaction with hydroxyl radical in air (Atkinson 1987; quoted, Howard et al. 1991). Biodegradation: aqueous anaerobic t. = 48–300 h, based on anaerobic natural water die-away test data for 2,4-dinitrotoluene; aqueous aerobic t. = 672–4320 h, based on aerobic natural water die-away test data (Spanggord et al. 1981; quoted, Howard et al. 1991). Biotransformation: k = 1 . 10–10 mL cell–1 h–1 for bacterial transformation in water (Mabey et al. 1982) Biotransformation in marine sediments: all broken down in 28 d when incubated at 10°C, and in 7 d when incubated at 20°C in the sandy sediment; degraded by days 7 and 3 for incubation at 10 and 20°C, respectively, in fine-grained sediment (Nipper et al. 2004). Bioconcentration, Uptake (k1) and Elimination (k2) Rate Constants: Half-Lives in the Environment: Air: estimated atmospheric t. = 8 h, based on the vapor phase reaction with hydroxyl radical in air (GEMS 1985; quoted, Howard 1989); photooxidation t. = 284 – 2840 h, based on estimated rate constant for the reaction with hydroxyl radical in air (Atkinson 1987; quoted, Howard et al. 1991). Surface water: midday t. ~ 12 min in Aucilla river due to indirect photolysis using experimentally determined rate constant k = 3.6 h–1 (Zepp et al. 1984); photooxidation t. = 2 – 17 h in water, based on measured photooxidation rates in natural waters (Simmons & Zepp 1986; quoted, Howard et al. 1991) 89% was photo-transformed in 24 h and none left after 72 h from seawater solution under UV light (Nipper et al. 2004). Ground water: t. = 48 – 8640 h, based on estimated unacclimated aqueous anaerobic biodegradation half-life 2,4-dinitrotoluene and estimated unacclimated aqueous aerobic biodegradation half-life (Howard et al. 1991). © 2006 by Taylor & Francis Group, LLC Nitrogen and Sulfur Compounds 3319 Sediment: degraded by days 28 and 7 for incubation at 10 and 20°C, respectively, in sandy marine sediment; degraded by days 7 and 3 for incubation at 10 and 20°C, respectively, in fine-grain sediment (Nipper et al. 2004) Soil: t. = 672 – 4320 h, based on estimated unacclimated aqueous aerobic biodegradation half-life (Howard et al. 1991). TABLE 16.1.4.5.1 Reported vapor pressures of 2,6-dinitrotoluene at various temperatures Pella 1977 gas saturation-GC t/°C P/Pa 4.0 0.00342 10.0 0.0107 20.0 0.0383 30.0 0.147 40.0 0.483 50.0 1.718 mp/°C 57.25–57.75 eq. 1 P/mmHg log P = A – B/(T/K) A 13.99 B 5139 enthalpy of sublimation: .Hsubl = 98.324 kJ mol–1 FIGURE 16.1.4.5.1 Logarithm of vapor pressure versus reciprocal temperature for 2,6-dinitrotoluene. 2,6-Dinitrotoluene: vapor pressure vs. 1/T -4.0 -3.0 -2.0 -1.0 0.0 1.0 2.0 3.0 4.0 0.0028 0.003 0.0032 0.0034 0.0036 0.0038 1/(T/K) P( gol S ) aP/ Pella 1977 m.p. = 66 °C © 2006 by Taylor & Francis Group, LLC 3320 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals 16.1.4.6 2,4,6-Trinitrotoluene (TNT) Common Name: 2,4,6-Trinitrotoluene Synonym: TNT Chemical Name: 2,4,6-trinitrotoluene CAS Registry No: 118-96-7 Molecular Formula: C7H5N3O6, (NO2)3C6H2CH3 Molecular Weight: 227.131 Melting Point (°C): 80.5 (Lide 2003) Boiling Point (°C): 240 explodes (Weast 1982–83; Dean 1992; Lide 2003) Density (g/cm3): 1.654 (20°C, Weast 1982–83; Dean 1992) Dissociation Constant, pKa: Molar Volume (cm3/mol): 137.3 (20°C, calculated-density) 187.1 (calculated-Le Bas method at normal boiling point) Enthalpy of Fusion, .Hfus (kJ/mol): Entropy of Fusion, .Sfus (J/mol K): Fugacity Ratio at 25°C (assuming .Sfus = 56 J/mol K), F: 0.285 (mp at 80.5°C) Water Solubility (g/m3 or mg/L at 25°C or as indicated and reported temperature dependence equations. Additional data at other temperatures designated * are compiled at the end of this section): 120* (20°C, shake flask, measured range 0.30–99.5°C, Taylor & Rinkenbach 1923) 85.8 (21°C, Hale et al. 1979) 104* (20°C, temp range 10–30°C, Spanggord et al. 1983) 200 (15°C, Verschueren 1983) 100 (Dean 1992) 101.5* (average value at pH < 9.1, shake flask-HPLC/UV, measured range 6–42°C, Ro et al. 1996) 101.6, 100.5, 110.5 (pH 3.5, pH 6.8, pH 9.1, shake flask-HPLC/UV spectrophotometry, Ro et al. 1996) ln [S/(mg L–1)] = 16.12 – 3413/(T/K), temp range 6–42°C, (pH < 8, shake flask-HPLC/spec., Ro et al. 1996) 115* (23.02°C, shake flask-HPLC/UV, measured range 13.6–61°C, Phelan & Barnett 2001) 99.85* 97.7* 99.9* (20°C, pH 4.2, 5.7, 6.2, shake flask-HPLC/UV, measured range 2.3–38°C, Lynch et al. 2001) ln [S/(mg L–1)] = 16.981 – 3607.5/(T/K); temp range 2.3–38°C (composite solubility prediction correlation, shake flask-HPLC/UV measurements, Lynch et al. 2001) Vapor Pressure (Pa at 25°C or as indicated and reported temperature dependence equations. Additional data at other temperatures designated * are compiled at the end of this section): 0.352* (53°C, Knudsen effusion, measured range 50–143°C, Edwards 1950) log (PS/cmHg) = 14.34 – 6180/(T/K); range 50–81°C (solid, Knudsen effusion, Edwards 1950) log (PL/cmHg) = 10.90 – 4960/(T/K); range 81–143°C (liquid, Knudsen effusion, Edwards 1950) 0.0568* (54.756°C, Knudsen effusion, measured range 55–76°C, Lenchitz & Velicky 1970) log (P/mmHg) = 13.0776 – 5400.536/(T/K); temp range 55–76°C (Knudsen effusion, Lenchitz & Velicky 1970) 0.00107* (gas saturation-GC/ECD, measured range 287.15–329.65 K, Pella 1977) log (P/mmHg) = (12.31 ± 0.34) – (5175 ± 105)/(T/K), temp range 287.15–329.65 K (gas saturation, Pella 1977) log (P/kPa) = 7.36331 – 3199.923/(248.004 + t/°C); temp range 230–250°C (liquid, Antoine eq. from reported exptl. data, Boublik et al. 1984) 0.00078 (interpolated-Antoine eq.-I, Stephenson & Malanowski 1987) NO2 NO2 O2N © 2006 by Taylor & Francis Group, LLC Nitrogen and Sulfur Compounds 3321 log (PS/kPa) = 13.596 – 5874.238/(T/K); temp range 293–353 K (solid, Antoine eq.-I, Stephenson & Malanowski 1987) log (PS/kPa) = 12.2025 – 5400.536/(T/K); temp range 337–350 K (solid, Antoine eq-II., Stephenson & Malanowski 1987) log (PL/kPa) = 6.40336 – 2191.85/(–121.43 + T/K); temp range 353–523 K (liquid, Antoine eq.-III, Stephenson & Malanowski 1987) log (P/mmHg) = 7.67152 – 2669.4/(205.6 + t/°C); temp range 230–250°C (Antoine eq., Dean 1992) log (P/mmHg) = 6.3156 – 2.6756 . 103/(T/K) – 4.6215·log (T/K) + 6.1747 . 10–9·(T/K) – 2.3743 . 10–12·(T/K)2; temp range 354–518 K (vapor pressure eq., Yaws 1994) Henry’s Law Constant (Pa·m3/mol at 25°C): Octanol/Water Partition Coefficient, log KOW: 1.60 (shake flask, Log P Database, Hansch & Leo 1987) 1.8 (shake flask-HPLC, Leggett et al. 1992) 1.73 (recommended, Sangster 1993) 2.05 (estimated-SPARC, Elovitz & Weber 1999) Octanol/Air Partition Coefficient, log KOA: Bioconcentration Factor, log BCF or log KB: 1.09 (aquatic oligochaete Tubifex tubifex, Conder et al. 2004) Sorption Partition Coefficient, log KOC: Environmental Fate Rate Constants, k, and Half-Lives, t.: Volatilization: Photolysis: t. = 14 h in summer, t. = 22–84 h in winter in pure water and photolyzed very rapidly in natural waters (Mabey et al. 1983) photocatalytic degradation rates of TNT in a circular photocatalytic reactor using a UV lamp as a light source and TiO2 as a photocatalyst: 1) at different initial TNT concns: k = 0.0989 min–1 with t. = 7.07 min at initial concn of 10 mg/L; k = 0.0644 min–1 with t. = 10.76 min at initial concn of 20 mg/L; k = 0.0405 min–1 with t. = 17.11 min at initial concn of 30 mg/L; k = 0.0269 min–1 with t. = 25.77 min at initial concn of 50 mg/L; and k = 0.0165 min–1 with t. = 42.01 min at initial concn of 100 mg/L. 2) at different pH: k = 0.0173 min–1 with t. = 27.6 min at pH 3.0; k = 0.0422 min–1 with t. = 20.1 min at pH 7.0 and k = 0.0451 min–1 with t. = 21.5 min at pH 11.0 (Son et al. 2004) Photooxidation: Hydrolysis: Biodegradation: 95% disappearance within 2 h under aerobic conditions, and complete loss within 10 min under anaerobic conditions in sediment-water systems (Elovitz & Weber 1999) Biotransformation: 100 % biotransformed when incubated at both 10 and 20°C in 7 d in fine-grain sediment; in sandy sediment although some picric acid could still be measured after 28 d of incubation at 10°C, none left after 56 d of incubation at 20°C (Nipper 2004) Bioconcentration and Uptake and Elimination Rate Constants (k1 and k2): Half-Lives in the Environment: Air: Surface water: photolysis t. = 14 h in summer, t. = 22–84 h in water in pure water, less than 1/2 h in some natural waters (Mabey et al. 1983) photocatalytic degradation t. = 7.07 min to 42.1 min for different initial concn of TNT from 10- 100 mg/L, and t. = 27.1 – 21.5 min at pH 3.0–7.0 in a circular reactor, using a UV lamp as a light source and TiO2 as a photocatalyst (Son et al. 2004) Ground water: Sediment: rapid disappearance 95% within 2 h, of TNT in an aerobic sediment-water system; under anaerobic conditions, TNT loss was complete within 10 min (Elovitz & Weber 1999) © 2006 by Taylor & Francis Group, LLC 3322 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals 100 % biotransformed when incubated at both 10 and 20°C in 7 d in fine-grain sediment; in sandy sediment although some picric acid could still be measured after 28 d of incubation at 10°C, none left after 56 d of incubation at 20°C (Nipper 2004) Soil: Biota: steady-state concn reached within 1-h in uptake experiments, and TNT depuration after a 24-h exposure occurred completely by 3 h (aquatic oligochaete, Conder et al. 2004) TABLE 16.1.4.6.1 Reported aqueous solubilities of 2,4,6-trinitrotoluene (TNT) at various temperatures ln S = A – B/(T/K) (1) 1. Taylor & Rinkenbach ‘23 Spanggord et al. 1983 Ro et al. 1996 Phelan & Barnett 2001 shake flask shake flask-HPLC/UV shake flask-HPLC/UV t/°C S/g·m–3 t/°C S/g·m–3 t/°C pH S/g·m–3 t/°C S/g·m–3 average* 0.30 110 10 67 6 3.7 52.5 13.9 86 5.9 113 20 104 6 6.9 51.3 23.02 115 20.0 120 30 165 12 6.9 64.0 33.3 191 33.1 203 13 3.7 72.2 42.6 266 44.2 340 13 6.9 64.4 51.8 427 45.0 370 20 4.2 86.2 61.0 641 53.0 534 20 7.3 88.5 33.2 191 57.15 614 20 9.2 96.8 13.6 90 73.25 963 20 9.4 95.7 13.6 92 94.4 1375 20 10.1 91.2 99.5 1467 21 3.5 74.5 21 6.8 82.5 average of 3 sets of data 21 9.1 88.2 25 3.5 101.6 25 6.8 100.5 25 9 110.5 42 4.0 204.9 42 6.8 204.5 42 9.3 167.6 ln [S/(mg/L)] = 16.12 – 3413/(T/K) for pH < 8 2. Lynch et al. 2001 shake flask-HPLC/UV t/°C S/g·m–3 t/°C S/g·m–3 t/°C S/g·m–3 pH 4.2 pH 5.7 pH 6.2 2.3 49.5 2.3 54.5 2.4 55.0 2.3 50.5 2.2 54.2 2.4 56.4 2.6 54.9 2.3 47.5 2.4 54.9 2.6 55.7 2.3 47.3 2.4 55.4 4.2 57.6 4.1 47.9 4.7 56.7 © 2006 by Taylor & Francis Group, LLC Nitrogen and Sulfur Compounds 3323 TABLE 16.1.4.6.1 (Continued) Lynch et al. 2001 shake flask-HPLC/UV t/°C S/g·m–3 t/°C S/g·m–3 t/°C S/g·m–3 4.2 57.7 4.1 48.2 4.7 57.4 4.2 45.7 4.6 58.1 5.2 56.7 4.2 48.4 4.6 59.1 5.2 56.1 20 100.7 20 96.7 20 99.6 20 99.0 20 98.7 20 100.2 20 99.2 20.1 98.9 20.1 99.5 20 101.7 20.1 100.6 20.1 96.3 20.1 96.3 20.2 98.8 20.1 99.5 20.1 95.9 20.2 99.8 20.1 99.8 20.1 96.0 20.2 97.5 20.2 94.6 20.1 97.8 20.2 100.4 20.2 97.2 36 211.7 35.7 208.5 35.9 216.5 36 213.1 35.7 213.5 35.9 213.9 36 208.5 36 215.2 36 212.2 36 211.6 36 214.3 36 215.3 37.7 219.6 37.7 229.7 37.6 229.4 37.7 219.4 37.7 230.6 37.6 231.4 37.8 218.2 37.7 226.2 38 234.4 37.8 214.8 37.7 228.3 38 235 eq. 1 S/(mg L–1) eq. 1 S/(mg L–1) eq. 1 S/(mg L–1) A 22.741 A 22.399 A 23.244 B 6332 B 6230 B 6506.8 composite correlation eq. : ln [S/(mg L–1) = 16981 – 3607.5/(T/K); temp range 2.3–38°C FIGURE 16.1.4.6.1 Logarithm of mole fraction solubility (ln x) versus reciprocal temperature for 2,4,6-trinitrotoluene. 2,4,6-Trinitrotoluene (TNT): solubility vs. 1/T -12.5 -12.0 -11.5 -11.0 -10.5 -10.0 -9.5 0.0028 0.003 0.0032 0.0034 0.0036 0.0038 1/(T/K) x nl Taylor & Rinkenbach 1923 Spanggord et al. 1983 Phelan & Barnett 2001 © 2006 by Taylor & Francis Group, LLC 3324 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals TABLE 16.1.4.6.2 Reported vapor pressures of 2,4,6-trinitrotoluene (2,4,6-TNT) at various temperatures and the coefficients for the vapor pressure equations log P = A – B/(T/K) (1) ln P = A – B/(T/K) (1a) log P = A – B/(C + t/°C) (2) ln P = A – B/(C + t/°C) (2a) log P = A – B/(C + T/K) (3) log P = A – B/(T/K) – C·log (T/K) (4) Edwards 1950 Lenchitz & Velicky 1970 Pella 1977 Knudsen method Knudsen effusion gas saturation-GC t/°C P/Pa t/°C P/Pa t/°C P/Pa 53.0 0.0352 54.756 0.0568 14.0 0.000302 60.1 0.0724 59.704 0.0935 19.0 0.000412 60.8 0.0843 64.853 0.1613 25.0 0.00107 61.5 0.0915 70.02 0.3118 25.3 0.00128 61.0 0.0829 72.469 0.3665 26.5 0.00170 72.1 0.4146 72.493 0.3409 35.0 0.00676 72.1 0.4186 75.065 0.5142 40.0 0.00887 78.5 0.8586 65.91 0.1811 45.0 0.0143 78.5 0.7839 68.933 0.2342 50.0 0.0243 78.3 0.8293 73.981 0.4453 55.0 0.0446 79.8 0.8733 76.057 0.5796 56.5 0.05406 80.2 0.9546 82.4 1.0612 mp/°C 81.1 mp/°C 80.15–81.25 86.9 1.5865 99.5 5.2529 enthalpy of sublimation: eq. 2 P/mmHg 99.5 5.4262 .Hsubl = 120.92 kJ mol–1 A 12.31 110.6 11.012 (at 25°C) B 5175 110.5 10.612 131.5 46.396 eq. 1 P/mmHg enthalpy of sublimation: 141.4 82.793 A 13.0776 .Hsubl = 99.161 kJ mol–1 142.0 87.728 B 5400.536 142.5 82.260 For solid: eq. 1 P/cmHg A 14.34 B 6180 .Hsubl = 118.41 kJ mol–1 For liquid: eq. 1 P/cmHg A 10.90 B 4960 .Hsubl = 94.98.34 kJ mol–1 © 2006 by Taylor & Francis Group, LLC Nitrogen and Sulfur Compounds 3325 FIGURE 16.1.4.6.2 Logarithm of vapor pressure versus reciprocal temperature for 2,4,6-trinitrotoluene. 2,4,6-Trinitrotoluene: vapor pressure vs. 1/T -4.0 -3.0 -2.0 -1.0 0.0 1.0 2.0 3.0 4.0 0.0018 0.0022 0.0026 0.003 0.0034 0.0038 1/(T/K) P( gol S ) aP/ Edwards 1950 Lenchitz & Velicky 1970 Pella 1977 b.p. =240 °C explodes b.p. = 80.5 °C © 2006 by Taylor & Francis Group, LLC 3326 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals 16.1.4.7 1-Nitronaphthalene (.-Nitronaphthalene) Common Name: 1-Nitronaphthalene Synonym: .-nitronaphthalene Chemical Name: 1-nitronaphthalene, .-nitronaphthalene CAS Registry No: 86-57-7 Molecular Formula: C10H7NO2 Molecular Weight: 173.169 Melting Point (°C): 61 (Lide 2003) Boiling Point (°C): 304.0 (Weast 1982–83; Dean 1985; Stephenson & Malanowski 1987) Density (g/cm3 at 20°C): 1.3320 (Weast 1982–83) 1.2230 (Dean 1985) Molar Volume (cm3/mol): 176.1 (calculated-Le Bas method at normal boiling point) 135.8 (calculated-density) Dissociation Constant pKa: Enthalpy of Fusion, .Hfus (kJ/mol): 17.99 (Tsonopoulos & Prausnitz 1971) Entropy of Fusion, .Sfus (J/mol K): 54.39 (Tsonopoulos & Prausnitz 1971) Fugacity Ratio at 25°C (assuming .Sfus = 56 J/mol K), F: 0.443 (mp at 61°C) Water Solubility (g/m3 or mg/L at 25°C): 50.0 (Aqueous Solubility Database, Yalkowsky et al. 1987) 9.82 (generator column-HPLC/UV, Yu & Xu 1992) 9.83 (calculated-molar concentration, Yu & Xu 1992) 50; 34.6 (quoted exptl.; calculated-group contribution method, Kuhne et al. 1995) Vapor Pressure (Pa at 25°C and reported temperature dependence equations): 0.202 (effusion method-fitted to Antoine eq., Radchenko & Kitiagorodskii 1974) 0.202 (solid, extrapolated-Antoine eq.-I, Stephenson & Malanowski 1987) 0.184 (liquid, extrapolated-Antoine eq.-III, Stephenson & Malanowski 1987) log (PS/kPa) = 8.31261 – 3579.698/(T/K); temp range 309–326 K (solid, Antoine eq.-I, Stephenson & Malanowski 1987) log (PS/kPa) = 13.223 – 5584/(T/K); temp range 325–332 K (solid, Antoine eq.-II, Stephenson & Malanowski 1987) log (PL/kPa) = 7.8959 – 3468.4/(T/K); temp range 332–580 K (liquid, Antoine eq.-III, Stephenson & Malanowski 1987) Henry’s Law Constant (Pa m3/mol at 25°C): 3.463 (calculated-P/C with selected values) 0.178 (gas stripping-GC, Altschuh et al. 1999) Octanol/Water Partition Coefficient, log KOW: 3.19 (Hansch & Leo 1979) 3.19 (shake flask, Hansch & Leo 1987) NO2 © 2006 by Taylor & Francis Group, LLC Nitrogen and Sulfur Compounds 3327 3.19 (shake flask-UV, Debnath & Hansch 1992) 3.19 (recommended, Sangster 1993) Octanol/Air Partition Coefficient, log KOA: Bioconcentration Factor, log BCF: Sorption Partition Coefficient, log KOC: Environmental Fate Rate Constants, k, or Half-Lives, t.: Volatilization: Photolysis: measured photolysis rate constant are: 15.9 . 10–4 s–1 in a 6400-L indoor all-Teflon chamber under blacklamp irradiation and 1.37 . 10–4 s–1 outdoor in a 1000-L all-Teflon chamber under natural solar irradiation (Atkinson et al. 1989); photolysis rate kphot = 1.5 . 10–4 s–1 with a half-life of 1.7 h (Arey et al. 1990) Hydrolysis: Oxidation: rate constant k, for gas-phase second order rate constants, kOH for reaction with OH radical, kNO3 with NO3 radical and kO3 with O3 or as indicated, *data at other temperatures see reference: kOH = (5.4 ± 1.8) . 10–12 cm3 molecule–1 s–1; kNO3 . 7.2 . 10–15 cm3 molecule–1 s–1, kO3 < 6.0 . 10–19 cm3 molecule–1 s–1 and kN2O5 = 1.3 . 10–18 cm3 molecule–1 s–1 with N2O5 and at 298 ± 2 K in the atmosphere (Atkinson et al. 1989) kOH = 5.4 . 10–12 cm3 molecule–1 s–1 with calculated lifetime of 2.9 d; kNO3 . 7.2 . 10–15 cm3 molecule–1 s–1 with calculated lifetime of –13 d, kO3 < 6.0 . 10–19 cm3 molecule–1 s–1 with a lifetime of > 28 d and kN2O5 = 1.3 . 10–18 cm3 molecule–1 s–1 with N2O5 a calculated lifetime of 2.4 yr at 298 ± 2 K in the atmosphere (Arey et al. 1990) Biodegradation: Biotransformation: Bioconcentration, Uptake (k1) and Elimination (k2) Rate Constants: Half-Lives in the Environment: Air: calculated lifetime of ~2 h based on measured outdoor photolysis rate and rate constants the gas-phase reactions (Atkinson et al. 1989); photolysis t. = 1.7 h using an average 12-h daytime NO2 photolysis rate k = 5.2 . 10–3 s–1 – a dominant atmospheric loss process; calculated lifetimes of 2.9 d, –13 d, > 28 d and 2.4 yr due to reactions with OH radial, NO3 radical, O3 and N2O5 (Arey et al. 1990) © 2006 by Taylor & Francis Group, LLC 3328 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals 16.1.5 AMIDES AND UREAS 16.1.5.1 Acetamide Common Name: Acetamide Synonym: ethanamide Chemical Name: acetamide, acetic acid amine CAS Registry No: 60-35-5 Molecular Formula: C2H5NO, CH3CONH2 Molecular Weight: 59.067 Melting Point (°C): 80.16 (Lide 2003) Boiling Point (°C): 221 (Lide 2003) Density (g/cm3 at 20°C): 0.9986 (78°C, Weast 1982–83) 1.159 (Verschueren, 1983) Molar Volume (cm3/mol): 59.2 (calculated-density, Stephenson & Malanowski 1987) 66.9 (calculated-Le Bas method at normal boiling point) Dissociation Constant pKa: 7.62 Enthalpy of Vaporization, .HV (kJ/mol): 56.1 (at bp, Riddick et al. 1986) Enthalpy of Sublimation, .Hsubl (kJ/mol): 78.66 (25°C, Riddick et al. 1986) Enthalpy of Fusion, .Hfus (kJ/mol): 17.707 (Riddick et al. 1986) Entropy of Fusion, .Sfus (J/mol K): Fugacity Ratio at 25°C (assuming .Sfus = 56 J/mol K), F: 0.288 (mp at 80.16°C) Water Solubility (g/m3 or mg/L at 25°C or as indicated): 975000 (20°C, Verschueren 1983) 408000 (20°C, Riddick et al. 1986) Vapor Pressure (Pa at 25°C and reported temperature dependence equations): 8.61 (extrapolated-regression of tabulated data, temp range 65–222°C, Stull 1947) log (P/mmHg) = [–0.2185 . 14025.3/(T/K)] + 9.088352; temp range 65.0–222°C (Antoine eq., Weast 1972–73) 100 (Riddick et al. 1986) log (P/kPa) = 8.24516 – 3282.80/(T/K); temp range 65–150°C (Antoine eq., Riddick et al. 1986) log (P/kPa) = 7.93409 – 2936.07/(T/K); temp range 65–bp (Antoine eq., Riddick et al. 1986) 2.44 (interpolated-Antoine eq.-I, Stephenson & Malanowski 1987) log (PS/kPa) = 10.9717 – 4050.1/(T/K); temp range 298–349 K (solid, Antoine eq.-I, Stephenson & Malanowski 1987) log (PL/kPa) = 7.97079 – 1998.3/(–89.32 + T/K); temp range 381–492 K (liquid, Antoine eq.-II, Stephenson & Malanowski 1987) log (P/mmHg) = –413.1683 + 8.1328 . 103/(T/K) + 172.9·log (T/K) – 0.16059·(T/K) + 5.3892 . 10–5·(T/K)2; temp range 354–761 K (vapor pressure eq., Yaws 1994) Henry’s Law Constant (Pa·m3/mol at 25°C): 3.53 . 10–4 (calculated-P/C with selected values) Octanol/Water Partition Coefficient, log KOW: –1.09 (shake flask-radiochemical method, Cornford 1982) O NH2 © 2006 by Taylor & Francis Group, LLC Nitrogen and Sulfur Compounds 3329 –1.26 (shake flask, Log P Database, Hansch & Leo 1987) –1.26 (shake flask-GC, Sotomatsu et al. 1987) –1.26 (recommended Sangster 1989, 1993) –1.23 (calculated-QSAR, Kollig 1993) –1.26 (recommended, Hansch et al. 1995) Octanol/Air Partition Coefficient, log KOA: Bioconcentration Factor, log BCF: Sorption Partition Coefficient, log KOC: –1.55 (calculated-KOW, Kollig 1993) Environmental Fate Rate Constants, k, or Half-Lives, t.: Volatilization: Photolysis: Oxidation: photooxidation t. = 3.2–32 h in air, based on estimated rate constant for the vapor-phase reaction with hydroxyl radical in air (Atkinson 1987; quoted, Howard et al. 1991); atmospheric transformation lifetime was estimated to be < 1 d (Kelly et al. 1994). Hydrolysis: overall rate constant kh = 5.5 . 10–12 s–1 with t. = 3950 yr; acid rate constant kA = 8.36 . 10–6 s–1 and base rate constant kB = 5.5 . 10–5 s–1 at 25°C and pH 7 (Mabey & Mill 1978) acid rate constant k = 0.03 [M ± (H+) ± h]–1 at pH 5 and base rate constant k = 0.17 [M ± (OH–) ± h]–1 at pH 9 with first-order hydrolysis t. = 3950 yr at pH 7 and 25°C, (Mabey & Mill 1978; quoted, Howard et al. 1991). Biodegradation: aqueous aerobic biodegradation t. = 24–168 h, based on aerobic aqueous screening test data (Malaney & Gerhold 1962, 1969; Urano & Kato 1986; quoted, Howard et al. 1991); aqueous anaerobic biodegradation t. = 96–672 h, based on estimated unacclimated aqueous aerobic biodegradation half-life (Howard et al. 1991). Biotransformation: Bioconcentration, Uptake (k1) and Elimination (k2) Rate Constants: Half-Lives in the Environment: Air: photooxidation t. = 3.2–32 h, based on estimated rate constant for the vapor-phase reaction with hydroxyl radical in air (Atkinson 1987; quoted, Howard et al. 1991); atmospheric transformation lifetime was estimated to be < 1 d (Kelly et al. 1994). Surface water: t. = 24–168 h, based on estimated unacclimated aqueous aerobic biodegradation half-life (Howard et al. 1991). Groundwater: t. = 48–336 h, based on estimated unacclimated aqueous aerobic biodegradation half-life (Howard et al. 1991). Sediment: Soil: t. = 24–168 h, based on estimated unacclimated aqueous aerobic biodegradation half-life (Howard et al. 1991). Biota: © 2006 by Taylor & Francis Group, LLC 3330 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals 16.1.5.2 Acrylamide Common Name: Acrylamide Synonym: 2-propenamide Chemical Name: acrylamide CAS Registry No: 79-06-1 Molecular Formula: C3H5NO, CH2=CHCONH2 Molecular Weight: 71.078 Melting Point (°C): 84.5 (Lie 2003) Boiling Point (°C): 192.5 (Lide 2003) Density (g/cm3 at 20°C): 1.122 (30°C, Dean 1985) Molar Volume (cm3/mol): 80.8 (calculated-Le Bas method at normal boiling point) Dissociation Constant pKa: Enthalpy of Fusion, .Hfus (kJ/mol): Entropy of Fusion, .Sfus (J/mol K): Fugacity Ratio at 25°C (assuming .Sfus = 56 J/mol K), F: 0.261 (mp at 84.5°C) Water Solubility (g/m3 or mg/L at 25°C): 2050000 (quoted, Verschueren 1983) 2150000 (30°C, Dean 1985) Vapor Pressure (Pa at 25°C and reported temperature dependence equations): 0.616 (average, extrapolated-Antoine eq.-I and II, Stephenson & Malanowski 1987) log (PL/kPa) = 7.395 – 3213/(/K), temp range 357–413K (Antoine eq.-I, Stephenson & Malanowski 1987) log (PL/kPa) = 10.31055 – 3994.667/(T/K), temp range 373–413 K (Antoine eq.-II, Stephenson & Malanowski 1987) log (P/mmHg) = 17.0034 – 4.4434 . 103/(T/K) –1.7158·log (T/K) + 2.0063 . 10–6·(T/K) – 8.0394 . 10–10·(T/K)2; temp range 358–477 K (vapor pressure eq., Yaws 1994) Henry’s Law Constant (Pam3/mol at 25°C): Octanol/Water Partition Coefficient, log KOW: –0.90 (shake flask, Fujisawa & Masuhara 1980, 1981) –1.24 (calculated-HPLC-RT correlation, Fujisawa & Masuhara 1981) –0.67 (shake flask, Log P Database, Hansch & Leo 1987) –0.78 (recommended, Sangster 1989) –0.67 (recommended, Hansch et al. 1995) Octanol/Air Partition Coefficient, log KOA: Bioconcentration Factor, log BCF: Sorption Partition Coefficient, log KOC: –0.969 (calculated-KOW, Kollig 1993) Environmental Fate Rate Constants, k, or Half-Lives, t.: Half-Lives in the Environment: Surface water: measured rate constant k = (1.0 ± 0.1) . 105 M–1 s–1 for direct reaction with ozone in water at pH 5.4–5.8 and 22 ± 1°C, with t. = 0.3 s at pH 7 (Yao & Haag 1991). O NH2 © 2006 by Taylor & Francis Group, LLC Nitrogen and Sulfur Compounds 3331 16.1.5.3 Benzamide Common Name: Benzamide Synonym: benzoylamide Chemical Name: benzamide CAS Registry No: 55-21-0 Molecular Formula: C7H7NO, C6H5CONH2 Molecular Weight: 121.137 Melting Point (°C): 127.3 (Lide 2003) Boiling Point (°C): 290 (Lide 2003) Density (g/cm3 at 20°C): Molar Volume (cm3/mol): 112.2 (130°C, Stephenson & Malanowski 1987) 132.4 (calculated-Le Bas method at normal boiling point) Dissociation Constant pKa: Enthalpy of Fusion, .Hfus (kJ/mol): Entropy of Fusion, .Sfus (J/mol K): Fugacity Ratio at 25°C (assuming .Sfus = 56 J/mol K), F: 0.0992 (mp at 127.3°C) Water Solubility (g/m3 or mg/L at 25°C or as indicated): 13500 (20–25°C, shake flask-gravimetric method, Dehn 1917) 13499 (Tsonopoulos & Prausnitz 1971) 13490 (Windholz 1983) 13515 (1 g in 74 mL, Budavari 1989) Vapor Pressure (Pa at 25°C and reported temperature dependence equations): 0.00522 (extrapolated, Antoine eq., Stephenson & Malanowski 1987) log (PS/kPa) = 11.69847 – 5062.899/(T/K), temp range 325–342 K (solid, Antoine eq., Stephenson & Malanowski 1987) Henry’s Law Constant (Pam3/mol at 25°C): 4.52 . 10–5 (calculated-P/C, this work) Octanol/Water Partition Coefficient, log KOW: 0.64 (shake flask-UV, Fujita et al. 1964) 0.65 (shake flask, Leo et al. 1971; Hansch & Leo 1979; Hansch & Leo 1987) 0.66 (shake flask-UV, Yaguzhinskii et al.1973) 0.84 (HPLC-k. correlation, Hammers et al. 1982) 0.64 (shake flask-UV, Sotomatsu et al. 1987) 0.50 (centrifugal partition chromatography CPC, Berthod et al. 1988) 0.81 (RP-HPLC-RT correlation, ODS column with masking agent, Bechalany et al. 1989) 0.64 (recommended, Sangster 1989, 1993) 0.65 (counter-current chromatography, Vallat et al. 1990) 0.65 (CPC-RV correlation, El Tayar et al. 1991) 0.64 (shake flask-GC, Alcorn et al. 1993) 0.64 (recommended, Hansch et al. 1995) NH2 O © 2006 by Taylor & Francis Group, LLC 3332 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals Octanol/Air Partition Coefficient, log KOA: Bioconcentration Factor, log BCF: Sorption Partition Coefficient, log KOC: 0.954; 1.301; 1.756 (sediment; Alfisol soil; Podzol soil, von Oepen et al. 1991) 1.46 (soil, quoted exptl., Meylan et al. 1992) 1.71 (soil, calculated-MCI . and fragment contribution, Meylan et al. 1992) 1.46 (soil, mean value, Kordel et al. 1993) 1.46 (soil, calculated-MCI 1., Sabljic et al. 1995) 1.46; 1.71 (HPLC-screening method; calculated-PCKOC fragment method, Muller & Kordel 1996) 1.87, 2.17, 1.12, 1.36, 1.645 (first generation Eurosoils ES-1, ES-2, ES-3, ES-4, ES-5, shake flask/batch equilibrium-HPLC/UV, Gawlik et al. 1998) 1.46, 1.22; 2.18, 1.75, 1.88, 1.83, 1.31 (soil: quoted lit., calculated-KOW; HPLC-screening method using LCcolumns of different stationary phases, Szabo et al. 1999) 1.747, 1.358, 1.236 (second generation of European reference soil set, Eurosoils ES-1, ES-3, ES-5, shake flask/batch equilibrium-HPLC/UV and HPLC-k. correlation, Gawlik et al. 2000) Environmental Fate Rate Constants, k, or Half-Lives, t.: Volatilization: Photolysis: Oxidation: aqueous photooxidation t. = 960–7.4 . 104 h, based on measured rates for reaction with OH radical in water (Anbar et al. 1966; Dorfman and Adams 1973; selected, Howard et al. 1991); photooxidation t. = 3.1 – 31 h in air, based on estimated rate constant for the vapor-phase reaction with hydroxyl radicals in air (Atkinson et al. 1987; selected, Howard et al. 1991). Hydrolysis: not expected to be significant based on estimated half-lives for hydrolysis of acetamide of 261, 3950, and 46 yr at pH 5,7,9, respectively, which were calculated using experimental acid and base hydrolysis rate constants for acetamide (Mabey & Mill 1978; selected, Howard et al. 1991). Biodegradation: aqueous aerobic biodegradation t. = 48 – 360 h, and aqueous anaerobic biodegradation t. = 192 – 1400 h, both based on grab sample aerobic soil column test data (Fournier & Salle 1974; selected, Howard et al. 1991). Biotransformation: Bioconcentration, Uptake (k1) and Elimination (k2) Rate Constants: Half-Lives in the Environment: Air: photooxidation t. = 3.1 – 31 h, based on estimated rate constant for the vapor-phase reaction with hydroxyl radical in air (Atkinson et al. 1987; selected, Howard et al. 1991). Surface water: t. = 48 – 360 h, based on grab sample aerobic soil column test data (Fournier & Salle 1974; selected, Howard et al. 1991). Ground water: t. = 96 – 720 h, based on grab sample aerobic soil column test data (Fournier & Salle 1974; selected, Howard et al. 1991). Sediment: Soil: t. = 48 – 360 h, based on grab sample aerobic soil column test data (Fournier & Salle 1974; selected, Howard et al. 1991). Biota: © 2006 by Taylor & Francis Group, LLC Nitrogen and Sulfur Compounds 3333 16.1.5.4 Urea Common Name: Urea Synonym: carbamide, carbonyldiamide, Aquacare, Aqiadrate, Basodexam, Keratinamin, Nutraplus, Onychomal, Pastaron, Ureaphil, Ureophil, Ureapearl Chemical Name: urea, carbamide, carbonyldiamide CAS Registry No: 57-13-6 Molecular Formula: CH4N2O, H2NCONH2 Molecular Weight: 60.055 Melting Point (°C): 133 (Lide 2003) Boiling Point (°C): decompose (Weast 1982–83; Lide 2003) Density (g/cm3): 1.323 (Weast 1982–83) Dissociation Constant, pKa: Molar Volume (cm3/mol): 58.0 (calculated-Le Bas method at normal boiling point) Enthalpy of Fusion, .Hfus (kJ/mol): Entropy of Fusion, .Sfus (J/mol K): Fugacity Ratio at 25°C (assuming .Sfus = 56 J/mol ± K), F: 0.0872 (mp at 133°C) Water Solubility (g/m3 or mg/L at 25°C or as indicated. Additional data at other temperatures designated * are compiled at the end of this section): 975000* (shake flask, measured range 0–69.5°C, Speyers 1902) 790000 (20–25°C, shake flask-gravimetric method, Dehn 1917) 1047000* (20°C, shake flask, measured range 0–70°C, Pinck & Kelly 1925) 53.97 wt %* (23.85°C, synthetic method, measured range 18.72–73.11°C, Shnidman & Sunier 1932) log x = – 609.8/(T/K) + 1.468; temp range 20–70°C (synthetic method, Shnidman & Sunier 1932) 0.4388* (60°C, mole fraction solubility, synthetic method, measured range 60–100°C, Kakinuma 1941) 997400 (W indholz 1983) 1000000 (Dean 1985; Budavari 1989) Vapor Pressure (Pa at 25°C and reported temperature dependence equations): 1.61 . 10–3 (extrapolated-Antoine eq., Stephenson & Malanowski 1987) log (PS/kPa) = 9.565 – 4579/(T/K); temp range 345–368 K (solid, Antoine eq., Stephenson & Malanowski 1987) Henry’s Law Constant (Pam3/mol): Octanol/Water Partition Coefficient, log KOW: –1.09 (Hansch & Leo 1979) –3.00 (Kenaga & Goring 1980) –1.21, –1.79 to –0.62 (shake flask method: mean, range of mean values, OECD 1981) –1.54 (shake flask-radiochemical method, Cornford 1982) –1.57 (HPLC-RT correlation, Harnish et al. 1983) –1.56 (shake flask, OECD 1981 Guidelines, Geyer et al. 1984) –1.66, –2.11 (shake flask, Log P Database, Hansch & Leo 1987) –1.60 (shake flask-UV, pH 7.4, Huang 1990) –2.11 (from Medchem software value, Chessells et al. 1992) –2.11 (recommended, Sangster 1993) –1.66 (Hansch et al. 1995) O H2N NH2 © 2006 by Taylor & Francis Group, LLC 3334 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals Octanol/Air Partition Coefficient, log KOA: Bioconcentration Factor, log BCF: 4.068 (alga chlorella fusca, wet wt. basis, Geyer et al. 1984) –0.10 (alga chlorella fusca, calculated-KOW, Geyer et al. 1984) Sorption Partition Coefficient, log KOC: 0.50, 0.62 (soil, quoted, calculated-MCI . and fragment contribution, Meylan et al. 1992) 0.90 (soil, calculated-MCI 1., Sabljic et al. 1995) Environmental Fate Rate Constants, k, and Half-Lives, t.: Half-Lives in the Environment: TABLE 16.1.5.4.1 Reported aqueous solubilities of urea at various temperatures Speyers 1902 Shnidman & Sunier 1932 Kakinuma 1941 re-calcd by Pinck & Kelly synthetic method-heating -shake flask synthetic method t/°C S/g·m–3 t/°C wt % x t/°C wt % x t/°C x urea 1# urea 2# 0 674000 18.72 51.10 0.2387 21.59 52.80 0.2513 60 0.4388 11.0 875000 26.80 55.37 0.2712 23.85 53.97 0.2602 65 0.4610 19.8 975000 27.31 55.83 0.2740 30.38 57.51 0.2888 70 0.4903 31.7 1310000 35.42 59.94 0.3099 35.15 59.97 0.3102 75 0.5204 51.4 1930000 37.36 60.87 0.3183 41.11 62.95 0.3377 80 0.6617 69.5 2530000 43.94 64.19 0.3489 43.85 64.31 0.3510 85 0.5843 46.56 65.39 0.3618 54.97 69.53 0.4065 90 0.6190 54.77 69.33 0.4041 55.88 70.10 0.4131 95 0.6542 67.02 70.38 0.4163 69.13 71.49 0.4294 100 0.6910 .Hsol/(kJ mol–1) 61.76 72.59 0.4428 63.79 73.64 0.4561 25°C 73.11 77.57 0.5093 70.49 76.60 0.4956 log x = A –B/(T/K) A 1.5314 mp/°C 132.7 mp/°C 132.6 B 631.86 Pinck & Kelly 1925 mole fraction solubility expressed as: shake flask log x = – 609.8/(T/K) + 1.468; temp range 20–70°C t/°C S/g·m–3 0 670000 10.0 840000 20.0 1047000 30.0 1360000 39.7 1654000 50.0 2050000 50.6 2064000 60.0 2460000 68.5 2950000 70.0 3146000 urea 1# – urea made by synthetic NH2 + CO2 process—re-crystallized from water urea 2# – urea made from calcium-cyanamid — re-crystallized from water and methanol © 2006 by Taylor & Francis Group, LLC Nitrogen and Sulfur Compounds 3335 FIGURE 16.1.5.4.1 Logarithm of mole fraction solubility (ln x) versus reciprocal temperature for urea. Urea: solubility vs. 1/T -2.5 -2.0 -1.5 -1.0 -0.5 0.0 0.5 0.0026 0.0028 0.003 0.0032 0.0034 0.0036 0.0038 1/(T/K) x nl Speyers 1902 Pinck & Kelly 1925 Shnidman & Sunier 1932 Kakinuma 1941 © 2006 by Taylor & Francis Group, LLC 3336 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals 16.1.6 NITROSAMINES 16.1.6.1 N-Nitrosodimethylamine Common Name: Dimethylnitrosoamine Synonym: N-nitrosodimethylamine, N-methyl-N-nitrosomethanamine, nitrous dimethylamine Chemical Name: dimethylnitrosoamine, N-nitrosodimethylamine CAS Registry No: 62-75-9 Molecular Formula: C2H6N2O, CH3N(NO)CH3 Molecular Weight: 74.081 Melting Point (°C): Boiling Point (°C): 152 (Lide 2003) Density (g/cm3 at 20°C): 1.005 (18°C, Verschueren 1983) Molar Volume (cm3/mol): 73.7 (10°C, Stephenson & Malanowski 1987) 87.7 (calculated-Le Bas method at normal boiling point) Dissociation Constant pKa: < 1.0 (Kollig 1993) Enthalpy of Fusion, .Hfus (kJ/mol): Entropy of Fusion, .Sfus (J/mol K): Fugacity Ratio at 25°C (assuming .Sfus = 56 J/mol K), F: Water Solubility (g/m3 or mg/L at 25°C): miscible (Mirvish et al. 1976) Vapor Pressure (Pa at 25°C and the reported temperature dependence equations): 1080 (Mabey et al. 1982) 730 (extrapolated-Antoine eq., Stephenson & Malanowski 1987) log (PL/kPa) = 7.10632 – 2159.476/(T/K), temp range 309–423 K (Antoine eq., Stephenson & Malanowski 1987) Henry’s Law Constant (Pam3/mol at 25°C): 3.344 (calculated, Mabey et al. 1982) Octanol/Water Partition Coefficient, log KOW: 0.06 (Radding et al. 1977) –0.57 (shake flask-UV, Singer et al. 1977) –0.68 (calculated-f const., Mabey et al. 1982) 0.46 (30.5°C, shake flask-HPLC, Vera et al. 1992) 0.76 (calculated, Kollig 1993) –0.57 (recommended, Sangster 1993) –0.57 (recommended, Hansch et al. 1995) Octanol/Air Partition Coefficient, log KOA: Bioconcentration Factor, log BCF: –0.96 (microorganisms-water, calculated-KOW, Mabey et al. 1982) Sorption Partition Coefficient, log KOC: –1.00 (sediment-water, calculated-KOW, Mabey et al. 1982) 0.448 (calculated-KOW, Kollig 1993) NO N © 2006 by Taylor & Francis Group, LLC Nitrogen and Sulfur Compounds 3337 Environmental Fate Rate Constants, k, or Half-Lives, t.: Volatilization: Photolysis: both aqueous and atmospheric photolysis t. = 0.5–1.0 h, based on measured rate of photolysis in the vapor phase under sunlight (Hanst et al. 1977; quoted, Howard et al. 1991). Hydrolysis: Oxidation: rate constant k, for gas-phase second order rate constants, kOH for reaction with OH radical, kNO3 with NO3 radical and kO3 with O3 or as indicated, *data at other temperatures see reference: rate constants k < 3600 M–1 h–1 for singlet oxygen, and k < 3600 M–1 h–1 for peroxy radical at 25°C (Mabey et al. 1982); kOH = 3.0 . 10–12 cm3 molecule–1 s–1 and kO3 . 1 . 10–20 cm3 molecule–1 s–1 at 298 K (Tuazon et al. 1984); photooxidation t. = 25.4–254 h in air, based on measured rate constant for the reaction with OH radical in air (Howard et al. 1991); kOH = (2.53 – 3.6) . 10–12 cm3 molecule–1 s–1 for the gas-phase reactions with OH radical at 296–298 K (Atkinson 1989). Biodegradation: aqueous aerobic t. = 504–4320 h, based on aerobic soil die-away test data; and aqueous anaerobic t. = 2016–17280 h, based on estimated unacclimated aqueous aerobic biodegradation half-life (derived from results of Tate & Alexander 1975; and Oliver et al. 1979; Howard et al. 1991). Biotransformation: rate constant for bacterial transformation k = 3 . 10–12 mL ± cell–1 ± h–1 in water (Mabey et al. 1982). Bioconcentration, Uptake (k1) and Elimination (k2) Rate Constants: Half-Lives in the Environment: Air: t. = 0.5–1.0 h, based on measured rate of photolysis in the vapor phase under sunlight (Hanst et al. 1977; quoted, Howard et al. 1991); estimated photolysis t. ~ 5 min, t. = 3 d for reaction with OH radical and t. > 2 yr for reaction with O3 (Tuazon et al. 1984); photooxidation t. = 25.4–254 h, based on measured rate constant for the reaction with OH radical in air (Atkinson 1985; quoted, Howard et al. 1991). Surface water: t. = 0.5–1.0 h, based on measured rate of photolysis in the vapor phase under sunlight (Hanst et al. 1977; quoted, Howard et al. 1991). Groundwater: t. = 1008–8640 h, based on estimated unacclimated aqueous aerobic biodegradation half-life (Howard et al. 1991). Sediment: Soil: degradation t. ~ 3 wk in 4 aerobic soils (shake flask-GC, Oliver et al. 1979) t. = 504–4320 h, based on aerobic soil die-away test data (derived from data of Tate & Alexander 1975 and Oliver et al. 1979, Howard et al. 1991). Biota: © 2006 by Taylor & Francis Group, LLC 3338 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals 16.1.6.2 N-Nitrosodipropylamine Common Name: Di-n-Propylnitrosoamine Synonym: N-nitrosodi-n-propylamine, N-nitroso-N-propyl-1-propanamine Chemical Name: di-n-propylnitrosoamine, N-nitrosodi-n-propylamine CAS Registry No: 621-64-7 Molecular Formula: C6H14N2O, CH3CH2CH2N(NO)CH2CH2CH3 Molecular Weight: 130.187 Melting Point (°C): Boiling Point (°C): 206 (Lide 2003) Density (g/cm3 at 20°C): Molar Volume (cm3/mol): 176.5 (calculated-Le Bas method at normal boiling point) Enthalpy of Fusion, .Hfus (kJ/mol): Entropy of Fusion, .Sfus (J/mol K): Fugacity Ratio at 25°C (assuming .Sfus = 56 J/mol K), F: Water Solubility (g/m3 or mg/L at 25°C): 9900 (Mirvish et al. 1976) Vapor Pressure (Pa at 25°C): 53.33 (37°C, calculated-Troutin’s rule, Mabey et al. 1982) Henry’s Law Constant (Pam3/mol at 25°C): 0.638 (calculated-P/C, Mabey et al. 1982) 0.355 (calculated-P/C, this work) Octanol/Water Partition Coefficient, log KOW: 1.31 (calculated as per Leo et al. 1971 from Mirvish et al. 1976 data, Callahan et al. 1979) 1.36 (shake flask-UV, Singer et al. 1977) 1.49 (calculated-f const., Mabey et al. 1982) 2.35 (30.5°C, shake flask-HPLC, Vera et al. 1992) 2.45 (recommended, Sangster 1993) 1.35 (Kollig 1993) 1.36 (recommended, Hansch et al. 1995) Octanol/Air Partition Coefficient, log KOA: Bioconcentration Factor, log BCF: 0.99 (microorganisms-water, calculated-KOW, Mabey et al. 1982) Sorption Partition Coefficient, log KOC: 1.18 (sediment-water, calculated-KOW, Mabey et al. 1982) 1.09 (calculated-KOW, Kollig 1993) Environmental Fate Rate Constants, k, or Half-Lives, t.: Volatilization: Photolysis: both aqueous and atmospheric photolysis t. = 0.17–1.0 h, based on measured rate of photolysis in the vapor phase under sunlight (Oliver 1981; quoted, Howard et al. 1991). Hydrolysis: NO N © 2006 by Taylor & Francis Group, LLC Nitrogen and Sulfur Compounds 3339 Oxidation: rate constants in water for singlet oxygen k < 3600 M–1 h–1 and for peroxy radical k < 3600 M–1 h–1 at 25°C (Mabey et al. 1982); photooxidation t. = 2.66–26.6 h in air, based on estimated rate constant for the reaction with hydroxyl radicals in air (Howard et al. 1991). Biodegradation: aqueous aerobic t. = 504–4320 h, based on aerobic soil die-away test data, and aqueous anaerobic t. = 2016–17280 h, based on estimated unacclimated aqueous aerobic biodegradation half-life (derived rom results of Tate & Alexander 1975 and Oliver et al. 1979, Howard et al. 1991). Biotransformation: rate constant for bacterial biotransformation k ~ 3 . 10–12 mL ± cell–1 ± h–1 in water (Mabey et al. 1982). Bioconcentration, Uptake (k1) and Elimination (k2) Rate Constants: Half-Lives in the Environment: Air: photooxidation t. = 2.66–26.6 h, based on estimated rate constant for the reaction with hydroxyl radicals in air (Howard et al. 1991). Surface water: t. = 0.17–1.0 h, based on measured rate of photolysis in the vapor phase under sunlight (Oliver 1981; quoted, Howard et al. 1991). Groundwater: t. = 1008–8640 h, based on estimated unacclimated aqueous aerobic biodegradation half-life (Howard et al. 1991). Sediment: Soil: degradation t. ~ 3 wk in 4 aerobic soils (shake flask-GC, Oliver et al. 1979) t. = 504 – 4320 h, based on aerobic soil die-away test data (derived from results of Tate & Alexander 1975 and Oliver et al. 1979, Howard et al. 1991). Biota © 2006 by Taylor & Francis Group, LLC 3340 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals 16.1.6.3 Diphenylnitrosoamine Common Name: Diphenylnitrosoamine Synonym: N-nitrosodiphenylamine, N-nitroso-N-phenylbenzamine Chemical Name: diphenylnitrosoamine, N-nitrosodiphenylamine CAS Registry No: 86-30-6 Molecular Formula: C12H10N2O, C6H5N(NO)C6H5 Molecular Weight: 198.219 Melting Point (°C): 66.5 (Weast 1982–83; Lide 2003) Boiling Point (°C): 151–153 (Windholz 1976; Callahan et al. 1979) Density (g/cm3 at 20°C): Molar Volume (cm3/mol): 220.5 (calculated-Le Bas method at normal boiling point) Dissociation Constant pKa: Enthalpy of Fusion, .Hfus (kJ/mol): Entropy of Fusion, .Sfus (J/mol K): Fugacity Ratio at 25°C (assuming .Sfus = 56 J/mol K), F: 0.392 (mp at 66.5°C) Water Solubility (g/m3 or mg/L at 25°C): 35.1 (shake flask-LSC, Banerjee et al. 1980) 40.0 (calculated-S, Mabey et al. 1982) Vapor Pressure (Pa at 25°C): 13.33 (estimated, Mabey et al. 1982) Henry’s Law Constant (Pam3/mol at 25°C): 66.87 (calculated-P/C, Mabey et al. 1982) Octanol/Water Partition Coefficient, log KOW: 3.13 (shake flask-LSC, Banerjee et al. 1980;) 3.13 (recommended, Sangster 1993) 3.13 (recommended, Hansch et al. 1995) Octanol/Air Partition Coefficient, log KOA: Bioconcentration Factor, log BCF: 2.63 (microorganisms-water, calculated-KOW, Mabey et al. 1982) 2.34 (quoted, Isnard & Lambert 1988) Sorption Partition Coefficient, log KOC: 2.81 (sediment-water, calculated-KOW, Mabey et al. 1982) 2.84 (calculated-KOW, Kollig 1993) Environmental Fate Rate Constants, k, or Half-Lives, t.: Volatilization: Photolysis: Hydrolysis: NO N © 2006 by Taylor & Francis Group, LLC Nitrogen and Sulfur Compounds 3341 Oxidation: rate constants in water for singlet oxygen k < 3600 M–1 h–1 and for peroxy radical k < 3600 M–1 ± h–1 at 25°C (Mabey et al. 1982); photooxidation t. = 0.70 – 7.0 h in air, based on measured rate constant for the reaction with hydroxyl radicals in air (Howard et al. 1991). Biodegradation: aqueous aerobic t. = 240 – 816 h, based on data from one soil-die-away test; a range was bracketed around the reported t. = 22 d (Mallik & Tesfai 1981; quoted, Howard et al. 1991); aqueous anaerobic t. = 960 – 3264 h, based on estimated unacclimated aqueous aerobic biodegradation half-life (Howard et al. 1991). Biotransformation: rate constant for bacterial transformation k = 1 . 10–10 mL ± cell–1 ± h–1 in water (Mabey et al. 1982). Bioconcentration, Uptake (k1) and Elimination (k2) Rate Constants: Half-Lives in the Environment: Air: photooxidation t. = 0.70 – 7.0 h, based on estimated rate constant for the reaction with hydroxyl radicals in air (quoted, Howard et al. 1991). Surface water: t. = 240 – 816 h, based on estimated unacclimated aqueous aerobic biodegradation half-life (Howard et al. 1991). Groundwater: t. = 480 – 1632 h, based on estimated unacclimated aqueous aerobic biodegradation half-life (Howard et al. 1991). Sediment: Soil: t. = 240 – 816 h, based on estimated unacclimated aqueous aerobic biodegradation half-life (Howard et al. 1991). Biota: © 2006 by Taylor & Francis Group, LLC 3342 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals 16.1.7 HETEROCYCLIC COMPOUNDS 16.1.7.1 Pyrrole Common Name: Pyrrole Synonym: 1H-pyrrole Chemical Name: pyrrole, 1H-pyrrole CAS Registry No: 109-97-7 Molecular Formula: C4H4NH Molecular Weight: 67.090 Melting Point (°C): –23.39 (Lide 2003) Boiling Point (°C): 129.79 (Lide 2003) Density (g/cm3 at 20°C): 0.9691 (Weast 1982–83; Dean 1985) 0.96985, 0.96565 (20°C, 25°C, Riddick et al. 1986) Molar Volume (cm3/mol): 69.2 (20°C, calculated-density, Stephenson & Malanowski 1987) 78.2 (calculated-Le Bas method at normal boiling point Dissociation Constant, pKa: –4.40 (Perrin 1972) –3.80 (Riddick et al. 1986) –4.10 (Sangster 1989) Enthalpy of Vaporization, .HV (kJ/mol): 45.15, 38.75 (25°C, bp, Riddick et al. 1986) Enthalpy of Fusion, .Hfus (kJ/mol): 7.908 (Riddick et al. 1986) Entropy of Fusion, .Sfus (J/mol K): Fugacity Ratio at 25°C (assuming .Sfus = 56 J/mol K), F: 1.0 Water Solubility (g/m3 or mg/L at 25°C): 47000 (Dean 1985) 45000 (Riddick et al. 1986) Vapor Pressure (Pa at 25°C and reported temperature dependence equations. Additional data at other temperatures designated * are compiled at the end of this section): 358285* (176.67°C, static-Bourdon gauge, measured range 176.67–271.11°C, Kobe et al. 1956) 1102* (ebulliometry, extrapolated-Antoine eq., measured range 65.67–166°C, Scott et al. 1967; Osborn & Douslin 1968) log (P/mmHg) = 7.30295 – 1507.015/(t/°C + 211.010); temp range 65.67–166°C (Antoine eq., ebulliometry, Scott et al. 1967) log [(P/atm) = [1 – 402.914 ± (T/K)] . 10^{0.870073 – 5.43768 . 10–4 ± (T/K) + 4.16086 . 10–7 ± (T/K)2}, temp range: 65.67–166°C (ebulliometric method, Cox eq., Scott et al. 1967) log (P/mmHg) = 7.30275 – 1506.877/(t/°C + 210.995), temp range 65.57–166°C (ebulliometric method, Antoine eq., Scott et al. 1967; Osborn & Douslin 1968) log [(P/atm) = [1 – 402.915 ± (T/K)] . 10^{0.872196 – 5.54923 . 10–4 ± (T/K) + 4.30369 . 10–7 ± (T/K)2}, temp range: 65.57–166°C (ebulliometric method, Cox eq., Osborn & Douslin 1968) 8386* (60.3°C, isoteniscope method, measured range 60.3–100.3°C, Eon et al. 1971) 1136 (calculated-Cox eq., Chao et al. 1983) log (P/atm) = [1– 402.916/(T/K)] . 10^{0.880256 – 6.05913 . 10–4 ± (T/K) + 5.02726 . 10–7 ± (T/K)2}; temp range: 250.0–635.0 K (Cox eq., Chao et al. 1983) NH © 2006 by Taylor & Francis Group, LLC Nitrogen and Sulfur Compounds 3343 1100 (extrapolated-Antoine eq., Boublik et al. 1984) log (P/kPa) = 6.42113 – 1502.586/(129.775 + t/°C); temp range 65.67–166°C (Antoine eq. from exptl. data of Scott et al. 1967, Boublik et al. 1984) 1100 (extrapolated-Antoine eq., Dean 1985, 1992) log (P/mmHg) = 7.29470 – 1501.56/(210.42 + t/°C); temp range 66–166°C (Antoine eq., Dean l985, 1992) 1100 (quoted lit., Riddick et al. 1986) log (P/kPa) = 6.42765 – 1506.877/(210.995 + t/°C); temp range not specified (Antoine eq., Riddick et al. 1986) 1103 (extrapolated-Antoine eq., Stephenson & Malanowski 1987) log (PL/kPa) = 6.42263 – 1504.171/(–62.39 + T/K); temp range 338–440 K (Antoine eq., Stephenson & Malanowski 1987) log (P/mmHg) = 54.1597 – 4.2745 . 103/(T/K) –15.873·log (T/K) – 4.5171 . 10–10·(T/K) + 4.2338 . 10–6·(T/K)2; temp range 250–640 K (vapor pressure eq., Yaws 1994) Henry’s Law Constant (Pa m3/mol at 25°C): 1.640 (calculated-P/C with selected values) Octanol/Water Partition Coefficient, log KOW at 25°C or as indicated 0.75 (shake flask-AS, Hansch & Anderson 1967; Leo et al. 1971; Hansch & Leo 1979) 0.62 (HPLC-RV correlation, Garst 1984) 0.82 (23°C, shake flask-HPLC, De Voogt et al. 1988) 0.80 (23°C, TLC-RT correlation, De Voogt et al. 1990) 0.75 (recommended, Sangster 1989, 1993) 0.75 (recommended, Hansch et al. 1995) Octanol/Air Partition Coefficient, log KOA: Bioconcentration Factor, log BCF: Sorption Partition Coefficient, log KOC: Environmental Fate Rate Constants, k, or Half-Lives, t.: Volatilization: Photolysis: Oxidation: rate constant k, for gas-phase second order rate constants, kOH for reaction with OH radical, kNO3 with NO3 radical and kO3 with O3 or as indicated, *data at other temperatures and/or the Arrhenius expression see reference: kOH = (1.22 ± 0.04) . 10–10 cm3 molecule–1 s–1 at 295 K (relative rate method, Atkinson et al. 1984) kO3 = 1.6 . 10–17 cm3 ± molecule–1 s–1 with loss rate of 1.0 d–1, kOH = 1.2 . 10–10 cm3 molecule–1 s–1 with loss rate of 10 d–1 and kNO3 = 4.9 . 10–11 cm3 molecule–1 s–1 with loss rate of 1000 d–1 (review, Atkinson & Carter 1984) kO3 = 1.6 . 10–17 cm3 ± molecule–1 s–1 with loss rate of 1.0 d–1, kOH = 1.2 . 10–10 cm3 molecule–1 s–1 with loss rate of 5.2 d–1 and kNO3 = 4.9 . 10–11 cm3 molecule–1 s–1 with loss rate k = 1000 d–1 (review, Atkinson 1985) kNO3 = (4.9 ± 1.1) . 10–11 cm3 molecule–1 s–1 at 295 ± 1 K (relative rate method, Atkinson et al. 1985) kO3 = 1.6 . 10–17 cm3 ± molecule–1 s–1 with calculated tropospheric lifetime . = 24 h, kOH = 1.2 . 10–10 cm3 molecule–1 s–1 with .(calc) = 2.3 h during daylight hours, kNO3 = 4.9 . 10–11 cm3 molecule–1 s–1 with .(calc) = 1.4 min during nighttime hours at room temp. (Atkinson et al. 1985) kOH = 1.2 . 10–10 cm3 molecule–1 s–1 with a loss rate of 5.2 d–1 at room temp. (Atkinson 1985) kOH* = (1.03 ± 0.06) . 10–10 cm3 molecule–1 s–1 at 298 K, measured range 298–442 K (flash photolysisresonance fluorescence, Wallington et al. 1988) kOH* = 9.31 . 10–10 cm3 molecule–1 s–1 at 298 K, measured range 298–442 K (flash photolysis-resonance fluorescence, Atkinson 1989) kOH = 1.10 . 10–12 cm3 molecule–1 s–1 at 298 K (recommended, Atkinson 1989) kOH(calc) = 287.45 . 10–12 cm3 molecule–1 s–1 (molecular orbital calculations, Klamt 1993) Hydrolysis: © 2006 by Taylor & Francis Group, LLC 3344 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals Biodegradation: Biotransformation: Bioconcentration, Uptake (k1) and Elimination (k2) Rate Constants: Half-Lives in the Environment: Air: calculated lifetimes of 2.3 h, 1.4 min and 24 h due to gas-phase reactions with OH radical (concn of 1 . 106 cm–3 during daylight hours), No3 radical (conc of 2.4 . 106 cm–3 during nighttime hours) and O3 (clean tropospheric conc of 7.2 . 1011 molecule cm–3), respectively, at room temp. (Atkinson et al. 1985) TABLE 16.1.7.1.1 Reported vapor pressures of pyrrole at various temperatures and the coefficients for the vapor pressure equations log P = A – B/(T/K) (1) ln P = A – B/(T/K) (1a) log P = A – B/(C + t/°C) (2) ln P = A – B/(C + t/°C) (2a) log P = A – B/(C + T/K) (3) log P = A – B/(T/K) – C·log (T/K) (4) Kobe et al. 1956 Scott et al. 1967 Eon et al. 1971 static-Bourdon gauge ebulliometry isoteniscope/manometry t/°C P/Pa t/°C P/Pa t/°C P/Pa 176.67 358285 65.671 9582 60.3 8386 182.22 399626 68.522 10884 70.3 13025 187.78 454747 71.374 12335 80.3 19732 193.33 509867 77.098 15740 90.3 29198 198.89 571878 79.970 17725 100.3 42263 204.44 647669 82.847 19920 210.00 730351 88.622 25007 .HV/(kJ mol–1) = 41.84 215.56 806142 94.422 31160 221.11 895713 100.244 38547 226.67 992174 106.096 47359 232.22 1081746 111.972 57803 237.78 1185097 117.875 70109 243.33 1309119 123.806 84525 248.89 1440031 129.764 101325 254.44 1564053 135.753 120798 260.00 1715635 141.768 143268 265.56 1867217 147.812 169052 271.11 2032580 153.884 198530 159.984 232087 166.109 270110 eq. 2 P/mmHg A 7.30295 B 1507.015 C 210.010 bp/°C 129.764 .HV/(kJ mol–1) = 45.10 © 2006 by Taylor & Francis Group, LLC Nitrogen and Sulfur Compounds 3345 FIGURE 16.1.7.1.1 Logarithm of vapor pressure versus reciprocal temperature for pyrrole. Pyrrole: vapor pressure vs. 1/T 0.0 1.0 2.0 3.0 4.0 5.0 6.0 7.0 8.0 0.0018 0.002 0.0022 0.0024 0.0026 0.0028 0.003 0.0032 0.0034 1/(T/K) P( gol S ) aP/ Kobe et al. 1956 Scott et al. 1967 Eon et al. 1971 b.p. =129.79 °C © 2006 by Taylor & Francis Group, LLC 3346 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals 16.1.7.2 Indole Common Name: Indole Synonym: benzo[b]pyrrole, 1-benzo[b]pyrrole, 1H-indole Chemical Name: indole CAS Registry No: 120-72-9 Molecular Formula: C8H7N Molecular Weight: 117.149 Melting Point (°C): 52.5 (Weast 1982–83; Lide 2003) Boiling Point (°C): 254.0 (Weast 1982–83; Stephenson & Malanowski 1987) 253.6 (Lide 2003) Density (g/cm3 at 20°C): 1.2200 (Weast 1982–83) 1.0643 (Dean 1985) Molar Volume (cm3/mol): 133.4 (calculated-Le Bas method at boiling point) Dissociation Constant, pKa: –3.5, –3.62 (Perrin 1972) –3.17 (Sangster 1989) Enthalpy of Fusion, .Hfus (kJ/mol): Entropy of Fusion, .Sfus J/mol K: Fugacity Ratio at 25°C (assuming .Sfus = 56 J/mol K), F: 0.537 (mp at 52.5°C) Water Solubility (g/m3 or mg/L at 25°C): 3558 (shake flask-GC, Price 1976) 1874 (Pearlman et al. 1984) Vapor Pressure (Pa at 25°C and reported temperature dependence equations): 2.24 (extrapolated-Antoine eq., Boublik et al. 1984) log (P/kPa) = 6.369 – 1933.005/(254.707 + t/°C); temp range 193.3–254.7°C (Antoine eq., Boublik et al. 1984) 1.565 (calculated-Antoine eq., Stephenson & Malanowski 1987) log (PS/kPa) = 10.3289 – 3916/(T/K); temp range 291–319 K, (solid, Antoine eq., Stephenson & Malanowski 1987) log (P/mmHg) = 94.1625 – 6.9431 . 103/(T/K) – 30.613·log (T/K) + 9.928 . 10–3·(T/K) + 1.7461 . 10–13·(T/K)2; temp range 274–790 K (vapor pressure eq., Yaws 1994) Henry’s Law Constant (Pam3/mol at 25°C): 0.14 (calculated-P/C with selected values) Octanol/Water Partition Coefficient, log KOW: 1.14 ± 0.01 (shake flask-UV, Iwasa et al. 1965) 2.14 (shake flask-UV, Hansch & Anderson 1967) 2.25 (shake flask-UV at pH 7.4, Rogers & Cammarata 1969) 2.00 (unpublished result, Leo et al. 1971) 2.00, 2.25, 2.13 ( Hansch & Leo 1979) 1.66 (RP-HPLC-RT correlation, Veith et al. 1979a) 2.17 (RP-HPLC-RT correlation, Hanai & Hubert 1982) 2.14 (inter-laboratory studies, shake flask average, Eadsforth & Moser 1983) NH © 2006 by Taylor & Francis Group, LLC Nitrogen and Sulfur Compounds 3347 1.92 (inter-laboratory studies, HPLC average, Eadsforth & Moser 1983) 2.16 ± 0.03 (HPLC-RV correlation-ALPM, Garst & Wilson 1984) 1.81 (HPLC-k. correlation, Eadsforth 1986) 2.16 (HPLC-RT correlation, Minick et al. 1988) 2.14 (recommended, Sangster 1989; 1993) 2.27 (23°C, shake flask-HPLC, De Voogt et al. 1988, 1990) 2.07 (HPLC-RT correlation, De Voogt et al. 1990) 2.19 (HPLC-RT correlation, Ritter et al. 1994) 2.14 (recommended, Hansch et al. 1995) Octanol/Air Partition Coefficient, log KOA: Bioconcentration Factor, log BCF: Sorption Partition Coefficient, log KOC: Environmental Fate Rate Constants or Half-Lives: Half-Lives in the Environment: © 2006 by Taylor & Francis Group, LLC 3348 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals 16.1.7.3 Pyridine Common Name: Pyridine Synonym: Chemical Name: pyridine CAS Registry No: 110-86-1 Molecular Formula: C5H5N Molecular Weight: 79.101 Melting Point (°C): –41.7 (Lide 2003) Boiling Point (°C): 115.23 (Lide 2003) Density (g/cm3 at 20°C): 0.9819 (Weast 1982–83) Molar Volume (cm3/mol): 80.6 (calculated-density, Rohrschneider 1973) 93.0 (calculated-Le Bas method at normal boiling point) Dissociation Constant, pK: 5.23 (pKa, Leo et al. 1971; Jori et al. 1983; Zachara et al. 1987) 5.198, 5.21, 5.22, 5.229 (Perrin 1972) 5.54 (UV, Yeh & Higuchi 1976) 5.23, 5.16 (quoted, shake flask-TN, Clarke 1984) 5.17 (pKBH + , Dean 1985; Riddick et al. 1986) 5.21 (pKa, Sangster 1989) Enthalpy of Vaporization, .HV (kJ/mol): 40.41, 36.39 (25°C, bp, Riddick et al. 1986) Enthalpy of Fusion, .Hfus (kJ/mol): 7.414 (Riddick et al. 1986) Entropy of Fusion, .Sfus (J/mol K): Fugacity Ratio at 25°C (assuming .Sfus = 56 J/mol K), F: 1.0 Water Solubility (g/m3 or mg/L at 25°C): miscible (Andon & Cox 1952; Andon et al. 1954; Jori et al. 1983; Riddick et al. 1986) miscible (Dean 1985; Zachara et al. 1987; Stephenson 1993a) miscible (Yaws et al. 1990) Vapor Pressure (Pa at 25°C and reported temperature dependence equations. Additional data at other temperatures designated * are compiled at the end of this section): 2666* (24.8°C, summary of literature data, temp range –18.9 to 115.4°C, Stull 1947) 2520 (interpolated-regression of tabulated data, Stull 1947) 620, 2109 (0, 20°C, static method-tensimeter, Brown & Barbaras 1947) 2775* (ebulliometry, measured range 47.3–115.5°C, extrapolated-Antoine eq., Herington & Martin 1953) log (P/mmHg) = 7.05811 – 1384.991/(216.296 + t/°C); temp range 47.3–115.5°C (Antoine eq., ebulliometric measurements, Herington & Martin 1953) 2774* (gas saturation, measured range 20–40°C, Andon et al. 1954) 461637* (176.67°C, static-Bourdon gauge, measured range 176.67–343.33°C, Kobe et al. 1956) 19920* (67.299°C, comparative ebulliometry, measured range 67.299–152.886°C, McCullough et al. 1957) log (P/mmHg) = 7.04162 – 1374.103/(215.014 + t/°C); temp range 67.3–152.9°C (Antoine eq. ebulliometry, McCullough et al. 1957) 2763* (ebulliometry, calculated-Antoine eq., Osborn & Douslin 1968) N © 2006 by Taylor & Francis Group, LLC Nitrogen and Sulfur Compounds 3349 log (P/mmHg) = 7.04144 – 1373.990/(t/°C + 215.001); temp range 67.3–152.9°C (ebulliometric method, Antoine eq., Osborn & Douslin 1968) log [(P/atm) = [1 – 399.384 ± (T/K)] . 10^{0.856586 – 6.60597 . 10–4 ± (T/K) + 5.93625 . 10–7 ± (T/K)2}, temp range: 67.3–152.9°C (ebulliometric method, Cox eq., Osborn & Douslin 1968) 2789 (calculated-Antoine eq., Cabani et al. 1971) log (P/mmHg) = [–0.2185 . 9649.4/(T/K)] + 8.347670; temp range –18.9 to 115.4°C (Antoine eq., Weast 1972–73) 2767 (calculated-Cox eq., Chao et al. 1983) log (P/atm) = [1– 388.399/(T/K)] . 10^{0.848882 – 6.09810 . 10–4 ± (T/K) + 5.15399 . 10–7 ± (T/K)2}; temp range: 235.0–620.0 K (Cox eq., Chao et al. 1983) 2775, 2763 (extrapolated-Antoine equations, Boublik et al. 1984) log (P/kPa) = 6.18358 – 1385.39/(115.256 + t/°C); temp range 47.3–115.47°C (Antoine eq. from reported exptl. data of Herington & Martin 1953, Boublik et al. 1984) log (P/kPa) = 6.16609 – 1373.826/(115.235 + t/°C); temp range 67.3–152.9°C (Antoine eq. from reported exptl. data of McCullough et al. 1957, Boublik et al. 1984) 2763 (extrapolated-Antoine eq., Dean 1985, 1992) log (P/mmHg) = 7.04115 – 1373.80/(214.98 + t/°C); temp range 67–153°C (Antoine eq., Dean l985, 1992) 2773 (Howard et al. 1986; quoted, Banerjee et al. 1990) 2700 (selected, Riddick et al. 1986) log (P/kPa) = 6.18595 – 1386.683/(216.469 + t/°C), temp range not specified (Antoine eq., Riddick et al. 1986) 2770 (interpolated-Antoine eq. II, Stephenson & Malanowski 1987) log (PL/kPa) = 6.17372 – 1379.953/(–57.436 + T/K); temp range 323–426 K (Antoine eq. I, Stephenson & Malanowski 1987) log (PL/kPa) = 6.30308 – 1448.781/(–50.948 + T/K); temp range 296–353 K (Antoine eq. II, Stephenson & Malanowski 1987) log (PL/kPa) = 6.16446 – 1373.263/(–58.18 + T/K); temp range 348–434 K (Antoine eq. III, Stephenson & Malanowski 1987) log (PL/kPa) = 6.284 – 1455.584/(–48.272 + T/K); temp range 431–558 K (Antoine eq. IV, Stephenson & Malanowski 1987) log (PL/kPa) = 7.25663 – 2578.625/(115.604 + T/K); temp range 552–620 K (Antoine eq. V, Stephenson & Malanowski 1987) 2773, 1653 (measured, calculated-solvatochromic parameters, Banerjee et al. 1990) 2573* (24.82°C, ebulliometry, measured range 23.55–116.23°C, Lencka 1990) ln (P/kPa) = 14.1480 – 3132.3/[(T/K) – 59.179); temp range 295.7–388.4 K (ebulliometric measurements, Antoine eq., Lencka 1990) log (P/mmHg) = 33.5541 – 3.1318 . 103/(T/K) –8.8646·log (T/K) + 7.1293 . 10–12·(T/K) + 2.2813 . 10–6·(T/K)2; temp range 232–620 K (vapor pressure eq., Yaws 1994) Henry’s Law Constant (Pa·m3/mol at 25°C or as indicated): 0.895 (volatility ratio-transpiration method, Andon et al. 1954) 0.900 (exptl., Hine & Mookerjee 1975) 0.595, 0.766 (calculated-group contribution, calculated-bond contribution, Hine & Mookerjee 1975) 1.114 (modified gas-stripping, Hawthorne et al. 1985) 1.120 (computed, Yaws et al. 1991) 0.305 (calculated-molecular structure, Russell et al. 1992) 27.78 (20°C, selected from literature experimentally measured data, Staudinger & Roberts 2001) log KAW = –1.508 – 128/(T/K) (van’t Hoff eq. derived from literature data, Staudinger & Roberts 2001) Octanol/Water Partition Coefficient, log KOW: 0.65 (shake flask-UV, Iwasa et al. 1965) 0.64 (Gehring et al. 1967) 0.65, 0.64 (Leo et al. 1971; Hansch & Leo 1979) 0.66 (HPLC-RT correlation, Mirrlees et al. 1976) 0.63 ± 0.02 (shake flask at pH 7, Unger et al. 1978) 0.63 (shake flask-titration, Clarke 1984; Clarke & Cahoon 1987) © 2006 by Taylor & Francis Group, LLC 3350 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals 0.63 ± 0.06 (HPLC-RV correlation-ALPM, Garst & Wilson 1984) 0.62 (shake flask-UV at pH 7.4, El Tayar et al. 1984) 0.63 (shake flask-potentiometric titration, Clarke 1984) 0.54 (calculated- activity coeff. . from UNIFAC, Campbell & Luthy 1985) 1.28 (HPLC-k. correlation, Eadsforth 1986) 0.79 (calculated-. from UNIFAC, Banerjee & Howard 1988) 0.70 (shake flask-CPC, Berthod et al. 1988) 0.63 (shake flask-HPLC at pH 7, De Voogt et al. 1988, 1990) 0.65 (recommended, Sangster 1989, 1993) 0.70 (RP-TLC-RT correlation, De Voogt et al. 1990) 0.65 (shake flask-UV, Yamagami et al. 1990) 0.60 (pH 7.2, Hansch et al. 1995) Octanol/Air Partition Coefficient, log KOA: Bioconcentration Factor, log BCF: Sorption Partition Coefficient, log KOC: –1.805 (estimated of Anvil Points subsurface materials, Zachara et al. 1987) –2.541 (estimated of Loring subsurface materials, Zachara et al. 1987) 0.340 (calculated-KOW, Kollig 1993) Environmental Fate Rate Constants, k, Half-Lives, t. Volatilization: Photolysis: Oxidation: rate constant k; for gas-phase second order rate constants, kOH for reaction with OH radical, kNO3 with NO3 radical and kO3 with O3 or as indicated *data at other temperatures see reference: photooxidation t. = 14.7–24.4 yr in water, based on measured rate data for the reaction with hydroxyl radical in aqueous solution (Dorfman & Adams 1973; selected, Howard et al. 1991) kOH = (4.9 ± 0.4) . 10–13 cm3 molecule–1 s–1 with atmospheric lifetimes of 46 d in clean troposphere and 23 d in moderately polluted atmosphere; kO3 < 1.1 . 10–20 cm3 molecule–1 s–1 with atmospheric lifetimes of > 4 yr in clean troposphere and > 1.3 yr in moderately polluted atmosphere at room temp. (relative rate method, Atkinson et al. 1987) kOH = (0.494 - 0.256) . 10–12 cm3 molecule–1 s–1 at 296–297 K (review, Atkinson 1989) kOH(calc) = 0.45 . 10–12 cm3 molecule–1 s–1 at room temp. (molecular orbital calculations, Klamt 1993) Hydrolysis: Biodegradation: aqueous aerobic t. = 24–168 h, based on unacclimated grab sample of aerobic soil (Sims & Sommers 1985; quoted, Howard et al. 1991); aqueous anaerobic t. = 168–672 h, based on anaerobic acclimated screening test data (Naik et al. 1972; selected, Howard et al. 1991). Biotransformation: Bioconcentration, Uptake (k1) and Elimination (k2) Rate Constants: Half-Lives in the Environment: Air: atmospheric lifetimes of 46 d in clean troposphere and 23 d in moderately polluted atmosphere, based on the gas-phase reaction with hydroxyl radical in air at room temp. and > 4 yr in clean troposphere and > 1.3 yr in moderately polluted atmosphere, based on the gas-phase reaction with O3 (calculated rate constant) in air at room temp. (Atkinson et al. 1987); photooxidation t. = 128–1284 h, based on measured rate data for the reaction with hydroxyl radical in air (selected, Howard et al. 1991). Surface water: photooxidation t. = 14.7–24.4 yr, based on measured rate data for the reaction with hydroxyl radical in aqueous solution (Dorfman & Adams 1973; selected, Howard et al. 1991); t. = 24–168 h, based on estimated aqueous aerobic biodegradation half-life (Howard et al. 1991). Groundwater: t. = 48–336 h, based on estimated aqueous aerobic biodegradation half-life (Howard et al. 1991). Sediment: Soil: disappears in less than 7 d in soil suspensions (Sims & O’Loughlin 1989); © 2006 by Taylor & Francis Group, LLC Nitrogen and Sulfur Compounds 3351 t. = 24–168 h, based on unacclimated grab sample of aerobic soil (Sims & Sommers 1985; selected, Howard et al. 1991). Biota: TABLE 16.1.7.3.1 Reported vapor pressures of pyridine at various temperatures and the coefficients for the vapor pressure equations log P = A – B/(T/K) (1) ln P = A – B/(T/K) (1a) log P = A – B/(C + t/°C) (2) ln P = A – B/(C + t/°C) (2a) log P = A – B/(C + T/K) (3) log P = A – B/(T/K) – C·log (T/K) (4) log P = A[1 – B/(T/K)] (5) where log A = a – b(T/K) + c(T/K)2 1. Stull 1947 Herington & Martin 1953 Andon et al. 1954 Kobe et al. 1956 summary of literature data ebulliometry gas saturation static-Bourdon gauge t/°C P/Pa t/°C P/Pa t/°C P/Pa t/°C P/Pa –18.9 133.3 47.327 8506 20 2109 176.67 461637 2.50 666.6 52.71 10820 25 2774 182.22 502988 13.2 1333 58.349 13806 40 6013 187.78 564988 24.8 2666 68.403 20805 193.33 633889 38.0 5333 75.77 27592 198.89 702790 46.8 7999 82.43 35246 204.44 778581 57.8 13332 82.728 35597 210.00 868153 75.0 26664 88.459 43472 215.56 950834 95.6 53329 92.749 50279 221.11 1047295 115.4 101325 100.994 65759 226.67 1157537 105.356 75351 232.22 1267778 mp/°C –42 107.169 79679 237.78 1378020 110.028 86860 243.33 1495152 113.222 95488 248.89 1632954 113.232 95536 254.44 1763866 113.374 95905 260.00 1908558 114.015 97713 265.56 2067030 114.699 99692 271.11 2232392 115.112 100914 276.67 2397755 115.287 101402 282.22 2590678 115.407 101758 287.78 2790491 115.473 101977 293.33 2997194 298.89 3183226 bp/°C 115.256 304.44 3438160 .HV/(kJ mol–1) = 36.39 310.00 3672423 Antoine eq. 315.56 3941137 eq. 2 P/mmHg 321.11 4216741 A 7.05811 326.67 4478565 B 1384.991 332.22 4774839 C 216.296 337.78 5084894 343.33 5429399 (Continued) © 2006 by Taylor & Francis Group, LLC 3352 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals TABLE 16.1.7.3.1 (Continued) 2. McCullough et al. 1957 Osborn & Douslin 1968 Lencka 1990 comparative ebulliometry ebulliometry ebulliometry t/°C P/Pa t/°C P/Pa t/°C P/Pa 67.299 19920 67.299 19920 23.55 2394 75.154 25007 73.154 25007 24.82 2573 79.045 31160 79.054 31160 27.0 2902 84.847 38547 84.974 38547 29.26 3290 90.946 47359 90.946 47359 31.63 3720 96.958 57803 96.958 57803 35.86 4626 103.008 70109 103.008 70109 41.0 6035 109.101 84525 109.101 84525 48.51 8525 115.234 101325 115.234 101325 54.17 10999 121.408 120789 121.408 120798 60.65 14321 127.622 143268 127.622 143268 69.25 20650 133.878 169052 133.878 169053 76.97 27794 140.174 198530 140.174 198517 83.45 35213 146.509 232067 146.509 232088 88.70 42359 152.886 270110 152.886 270111 91.76 47951 96.68 55423 mp/°C 115.23 Antoine eq 100.01 61720 Antoine eq eq. 2 P/mmHg 102.18 66148 eq. 2 P/mmHg A 7.04144 106.03 74603 A 7.04162 B 1373.990 112.70 91299 B 1374.103 C 215.001 116.23 101277 C 215.014 data also fitted to Cox eq. eq. 3 cP/kPa data also fitted to Cox eq. A 14.1480 eq. 5 P/atm B 3132.30 A C 59.719 a 0.858631 10–4b 6.7114 10–7c 6.0722 B 388.394 © 2006 by Taylor & Francis Group, LLC Nitrogen and Sulfur Compounds 3353 FIGURE 16.1.7.3.1 Logarithm of vapor pressure versus reciprocal temperature for pyridine. Pyridine: vapor pressure vs. 1/T 0.0 1.0 2.0 3.0 4.0 5.0 6.0 7.0 8.0 0.0016 0.002 0.0024 0.0028 0.0032 0.0036 0.004 1/(T/K) P( gol S ) aP/ experimental data Stull 1947 b.p. =115.23 °C © 2006 by Taylor & Francis Group, LLC 3354 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals 16.1.7.4 2-Methylpyridine Common Name: 2-Methylpyridine Synonym: .-picoline, 2-picoline Chemical Name: 2-methylpyridine, .-picoline CAS Registry No: 109-06-8 Molecular Formula: C5H4NCH3 Molecular Weight: 93.127 Melting Point (°C): –66.68 (Lide 2003) Boiling Point (°C): 129.38 (Lide 2003) Density (g/cm3 at 20°C): 0.9443 (Weast 1982–83) 0.9444, 0.93981 (20°C, 25°C, Riddick et al. 1986) Molar Volume (cm3/mol): 98.6 (20°C, calculated-density) 115.2 (calculated-Le Bas method at normal boiling point) Dissociation Constant, pK: 5.957, 6.06 (Perrin 1972) 5.97 (pKa, 20°C, Weast 1982–83) 6.00 (pKBH + , Riddick et al. 1986; quoted, Howard 1990) Enthalpy of Vaporization, .HV (kJ/mol): 42.919, 36.271 (25°C, bp, Riddick et al. 1986) Enthalpy of Fusion, .Hfus (kJ/mol): 9.724 (Riddick et al. 1986) Entropy of Fusion, .Sfus (J/mol K): Fugacity Ratio at 25°C (assuming .Sfus = 56 J/mol K), F: 1.0 Water Solubility (g/m3 or mg/L at 25°C): miscible (Andon & Cox 1952) miscible (Riddick et al. 1986; Yaws et al. 1990) miscible (Stephenson 1993a) Vapor Pressure (Pa at 25°C and reported temperature dependence equations. Additional data at other temperatures designated * are compiled at the end of this section): 1370* (interpolated-regression of tabulated data, temp range –11.0 to 128.8°C, Stull 1947) 308, 1140 (0, 20.3°C, static method-tensimeter, Brown & Barbaras 1947) 1277 (manometry, calculated-Antoine eq., Hopke & Sears 1951) 1496* (ebulliometry, extrapolated-Antoine eq., measured range 64.3–130°C, Herington & Martin 1953) log (P/mmHg) = 7.03450 – 1417.578/(211.874 + t/°C); temp range 64.3–130°C (ebulliometric measurements, Antoine eq., Herington & Martin 1953) 1496 (calculated-Antoine eq., Andon et al. 1954) 19920* (79.794°C, comparative ebulliometry, measured range 79.8–168°C. Scott et al. 1963a) log (P/mmHg) = 7.03202 – 1415.494/(t/°C + 211.589); temp range 79.8–168°C (ebulliometric measurements, Antoine eq., Scott et al. 1963a) 1493 (ebulliometry, calculated-Antoine eq., Osborn & Douslin 1968) log (P/mmHg) = 7.03192 – 1415.424/(t/°C + 211.589); temp range 79.8–168°C (ebulliometric measurements, Antoine eq., Osborn & Douslin 1968) log [(P/atm) = [1 – 402.536 ± (T/K)] . 10^{0.866637 – 6.80114 . 10–4 ± (T/K) + 6.00534 . 10–7 ± (T/K)2}, temp range: 79.8–168°C (ebulliometric method, Cox eq., Osborn & Douslin 1968) N © 2006 by Taylor & Francis Group, LLC Nitrogen and Sulfur Compounds 3355 log (P/mmHg) = [–0.2185 . 9933.2/(T/K)] + 8.290910; temp range –11.0 to 128.8°C (Antoine eq., Weast 1972–73) 1500 (calculated-Cox eq., Chao et al. 1983) log (P/atm) = [1– 402.320/(T/K)] . 10^{0.887914 – 7.70705 . 10–4 ± (T/K) + 6.85261 . 10–7 ± (T/K)2}; temp range: 215.0–620.0 K (Cox eq., Chao et al. 1983) 1067 (20°C, Verschueren 1983) 1494, 1498 (extrapolated-Antoine equations, Boublik et al. 1984) log (P/kPa) = 6.16509 – 1421.237/(212.286 + t/°C); temp range 64.363–130.04°C (Antoine eq. from reported exptl. data of Herington & Martin 1953, Boublik et al. 1984) log (P/kPa) = 6.15718 – 1415.663/(211.617 + t/°C); temp range 79.79–168.36°C (Antoine eq. from reported exptl. data of Scott et al. 1963, Boublik et al. 1984) 1494 (extrapolated-Antoine eq., Dean 1985, 1992) log (P/mmHg) = 7.0324 – 1415.73/(211.63 + t/°C), temp range: 80–168°C (Antoine eq., Dean 1985, 1992) 1333 (Riddick et al. 1986) log (P/kPa) = 6.15940 – 1417.578/(211.874 + t/°C); temp range not specified (Antoine eq., Riddick et al. 1986) 1386 (extrapolated-Antoine eq., Stephenson & Malanowski 1987) log (PL/kPa) = 5.2309 – 1164.1/(–71.0 + T/K); temp range 209–245 K (Antoine eq.-I, Stephenson & Malanowski 1987) log (PL/kPa) = 6.1558 – 1415.29/(–61.521 + T/K); temp range 352–442 K (Antoine eq.-II, Stephenson & Malanowski 1987) log (PL/kPa) = 6.15522 – 1414.906/(–61.566 + T/K); temp range 352–442 K (Antoine eq.-III, Stephenson & Malanowski 1987) log (PL/kPa) = 6.32356 – 1546.248/(–44.271 + T/K), temp range: 429–537 K (Antoine eq.-IV, Stephenson & Malanowski 1987) log (PL/kPa) = 7.32144 – 2667.496/(107.978 + T/K); temp range 521–621 K (Antoine eq.-V, Stephenson & Malanowski 1987) 1500* (ebulliometry, interpolated-Antoine eq., measured range 295.7–388.4 K, Lencka 1990) ln (P/kPa) = 14.1560 – 3249.15/[(T/K) – 61.863); temp range 295.7–388.4 K (ebulliometric measurements, Antoine eq., Lencka 1990) log (P/mmHg) = 34.3728 – 3.2825 . 103/(T/K) –9.0927·log (T/K) – 3.6324 . 10–10·(T/K) + 2.1425 . 10–6·(T/K)2; temp range 206–621 K (vapor pressure eq., Yaws 1994) Henry’s Law Constant (Pa·m3/mol at 25°C or as indicated and reported temperature dependence equations): 1.010 (measured volatility ratio-transpiration method, Andon et al. 1954) 1.010 (exptl., Hine & Mookerjee 1975) 0.821, 0.749 (calculated-group contribution, calculated-bond contribution, Hine & Mookerjee 1975) 2.90 (computed-vapor-liquid equilibrium VLE data, Yaws et al. 1991) 30.22 (20°C, selected from literature experimentally measured data, Staudinger & Roberts 2001) log KAW = –0.700 – 354/(T/K) (van’t Hoff eq. derived from literature data, Staudinger & Roberts 2001) Octanol/Water Partition Coefficient, log KOW: 0.52 (HPLC-RT correlation, Schultz & Moulton 1985) 1.11 (shake flask, Log P Database, Hansch & Leo 1987) 1.11 (shake flask-UV, Yamagami et al. 1990) 1.11 (recommended, Sangster 1989; 1993) 1.11 (recommended, Hansch et al. 1995) Octanol/Air Partition Coefficient, log KOA: Bioconcentration Factor, log BCF: 0.602 (calculated-KOW, Lyman et al. 1982) Sorption Partition Coefficient, log KOC: Environmental Fate Rate Constants, k, or Half-Lives, t.: © 2006 by Taylor & Francis Group, LLC 3356 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals Volatilization: using Henry’s law constant, t. = 88 h for a model river 1 m deep flowing at 1 m/s with a wind velocity of 3 m/s (estimated, Howard 1990). Photolysis: Oxidation: photooxidation t. = 11.2 d in air, based on the gas-phase reaction with photochemically produced hydroxyl radicals in air (Atkinson 1987; quoted, Howard 1990). Hydrolysis: Biodegradation: Biotransformation: Bioconcentration, Uptake (k1) and Elimination (k2) Rate Constants: Half-Lives in the Environment: Air: t. = 11.2 d, based on the gas-phase reaction with photochemically produced hydroxyl radicals in air (Atkinson 1987; quoted, Howard 1990). Surface water: estimated t. = 1.0 d for methylpyridine in Rhine River in case of a first order reduction process (Zoeteman et al. 1980) Groundwater: Sediment: Soil: Biota: TABLE 16.1.7.4.1 Reported vapor pressures of 2-methylpryridine at various temperatures and the coefficients for the vapor pressure equations log P = A – B/(T/K) (1) ln P = A – B/(T/K) (1a) log P = A – B/(C + t/°C) (2) ln P = A – B/(C + t/°C) (2a) log P = A – B/(C + T/K) (3) log P = A – B/(T/K) – C·log (T/K) (4) Stull 1947 Herington & Martin 1953 Scott et al. 1963(a) Lencka 1990 summary of literature data ebulliometry comparative ebulliometry ebulliometry t/°C P/Pa t/°C P/Pa t/°C P/Pa t/°C P/Pa –11.1 133.3 64.363 10660 79.794 19920 18.49 1015 12.6 666.6 69.916 13459 85.853 25007 22.09 1264 24.4 1333 76.836 17758 91.942 31160 24.58 1463 37.4 2666 82.362 21954 98.074 38547 26.74 1657 51.2 5333 88.566 27600 104.252 47359 30.60 2062 59.9 7999 93.617 33044 110.472 57803 33.71 2446 71.4 13332 101.283 42906 116.736 70109 40.03 3414 89.0 26664 108.594 54434 123.038 84525 48.69 5258 108.4 53329 114.552 65581 129.387 101325 57.60 7942 128.8 101325 117.647 72020 135.773 120798 71.51 14375 122.132 82297 142.207 143268 80.35 20380 mp/°C –70.0 126.992 91140 148.683 169052 87.31 26426 125.664 94663 155.201 198530 94.31 33920 127.828 96885 161.761 232087 101.18 42854 128.591 99021 168.356 270110 104.03 47076 129.290 100985 109.24 55653 129.608 101879 bp/°C 129.39 113.01 62604 130.037 103095 Antoine eq. 115.31 67182 © 2006 by Taylor & Francis Group, LLC Nitrogen and Sulfur Compounds 3357 TABLE 16.1.7.4.1 (Continued) Stull 1947 Herington & Martin 1953 Scott et al. 1963(a) Lencka 1990 summary of literature data ebulliometry comparative ebulliometry ebulliometry t/°C P/Pa t/°C P/Pa t/°C P/Pa t/°C P/Pa eq. 2 P/mmHg 119.20 75535 bp/°C 129.408 A 7.03202 122.93 84296 .HV/(kJ mol–1) = 37.76 B 1415.494 125.77 92024 eq. 2 P/mmHg C 211.598 129.88 102813 A 7.03450 B 1417.578 Antoine eq. C 211.874 eq. 3 P/kPa A 14.1560 B 3249.15 C 61.383 FIGURE 16.1.7.4.1 Logarithm of vapor pressure versus reciprocal temperature for 2-methylpyridine. 2-Methylpyridine: vapor pressure vs. 1/T 0.0 1.0 2.0 3.0 4.0 5.0 6.0 7.0 8.0 0.0018 0.0022 0.0026 0.003 0.0034 0.0038 0.0042 0.0046 1/(T/K) P( gol S ) aP / Herington & Martin 1953 Scott et al. 1963a Lencka 1990 Stull 1947 b.p. = 129.38 °C © 2006 by Taylor & Francis Group, LLC 3358 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals 16.1.7.5 3-Methylpyridine Common Name: 3-Methylpyridine Synonym: .-picoline, 3-picoline Chemical Name: 3-methylpyridine, .-picoline CAS Registry No: 108-99-6 Molecular Formula: C5H4NCH3 Molecular Weight: 93.127 Melting Point (°C): –18.14 (Lide 2003) Boiling Point (°C): 144.14 (Lide 2003) Density (g/cm3 at 20°C): 0.9443 (Weast 1982–83) 0.9566 (Riddick et al. 1986) Molar Volume (cm3/mol): 97.35 (20°C, calculated-density) 115.2 (calculated-Le Bas method at normal boiling point) Dissociation Constant, pK: 5.67, 5.703 (Perrin 1972) 5.68 (pKa, 20°C, Weast 1982–83; pKa, protonated cation + 1, Dean 1985) 5.75 (pKBH + , Riddick et al. 1986) 5.65 (pKa, Sangster 1989) Enthalpy of Vaporization, .HV (kJ/mol): 45.233, 37.323 (25°C, bp, Riddick et al. 1986) Enthalpy of Fusion, .Hfus (kJ/mol): 14.18 (Riddick et al. 1986) Entropy of Fusion, .Sfus (J/mol K): Fugacity Ratio at 25°C (assuming .Sfus = 56 J/mol K), F: 1.0 Water Solubility (g/m3 or mg/L at 25°C): miscible (Andon & Cox 1952; Andon et al. 1954; Yaws et al. 1990) miscible (Riddick et al. 1986; Howard 1993) miscible (Stephenson 1993a) Vapor Pressure (Pa at 25°C or as indicated and reported temperature dependence equations. Additional data at other temperatures designated * are compiled at the end of this section): 150.7, 594.6 (0, 20°C, static method-tensimeter, Brown & Barbaras 1947) 794* (ebulliometry, extrapolated-Antoine eq., Herington & Martin 1953) log (P/mmHg) = 7.03247 – 1469.894/(209.907 + t/°C); temp range 81.2–145.1°C (ebulliometric measurements, Antoine eq., Herington & Martin 1953) 794 (calculated-Antoine eq., Andon et al. 1954) 9582* (74.036.C, comparative ebulliometry, measured range 74.036–184.568.C, Scott et al. 1963b) log (P/mmHg) = 7.05375 – 1484.208/(t/°C + 211.532), temp range 79.8–168°C (ebulliometric measurements, Antoine eq., Scott et al. 1963b) 811 (ebulliometry, calculated-Antoine eq., Osborn & Douslin 1968) log (P/mmHg) = 7.30275 – 1506.877/(t/°C + 210.995), temp range: 74–185°C, (ebulliometric measurements, Antoine eq., Osborn & Douslin 1968) log [(P/atm) = [1 – 417.287 ± (T/K)] . 10^{0.854256 – 6.02835 . 10–4 ± (T/K) + 5.00169 . 10–7 ± (T/K)2}, temp range: 74–185°C (ebulliometric method, Cox eq., Osborn & Douslin 1968) 806 (calculated-Cox eq., Chao et al. 1983) N © 2006 by Taylor & Francis Group, LLC Nitrogen and Sulfur Compounds 3359 log (P/atm) = [1– 417.217/(T/K)] . 10^{0.865977 – 6.48542 . 10–4 ± (T/K) + 5.41256 . 10–7 ± (T/K)2}; temp range: 255.0–645.0 K (Cox eq., Chao et al. 1983) 796, 800 (extrapolated-Antoine equations, Boublik et al. 1984) log (P/kPa) = 6.16152 – 1472.639/(210.214 + t/°C); temp range 81.3–145.1°C (Antoine eq. from reported exptl. data of Herington & Martin 1953, Boublik et al. 1984) log (P/kPa) = 6.17577 – 1482.229/(211.305 + t/°C); temp range 74.03–184.6°C (Antoine eq. from reported exptl. data of Scott et al. 1963, Boublik et al. 1984) 800 (extrapolated-Antoine eq., Dean 1985, 1992) log (P/mmHg) = 7.05021 – 1481.78/(211.25 + t/°C); temp range 74–185°C (Antoine eq., Dean l985, 1992) 1333 (Riddick et al. 1986) log (P/kPa) = 6.15737 – 1469.894/(209.907 + t/°C); temp range not specified (Antoine eq., Riddick et al. 1986) 802 (extrapolated-Antoine eq., Stephenson & Malanowski 1987) log (PS/kPa) = 11.245 – 3246.9/(T/K); temp range 225–255 K (Antoine eq.-I, Stephenson & Malanowski 1987) log (PL/kPa) = 6.17593 – 1482.943/(–61.705 + T/K); temp range 347–458 K (Antoine eq.-II, Stephenson & Malanowski 1987) log (PL/kPa) = 6.17791 – 1484.285/(–61.554 + T/K); temp range 347–458 K (Antoine eq.-III, Stephenson & Malanowski 1987) log (PL/kPa) = 6.18988 – 1491.897/(–60.745 + T/K); temp range 347–381 K (Antoine eq.-IV, Stephenson & Malanowski 1987) log (PL/kPa) = 6.16648 – 1476.25/(–62.502 + T/K); temp range 374–458 K (Antoine eq.-V, Stephenson & Malanowski 1987) log (PL/kPa) = 6.38586 – 1659.184/(–38.176 + T/K); temp range 450–570 K (Antoine eq.-VI, Stephenson & Malanowski 1987) log (PL/kPa) = 7.57549 – 3151.52/(161.352 + T/K); temp range 561–645 K (Antoine eq.-II, Stephenson & Malanowski 1987) log (P/mmHg) = 35.2679 – 3.4364 . 103/(T/K) – 9.3555·log (T/K) – 1.3286 . 10–10·(T/K) + 2.0461 . 10–6·(T/K)2; temp range 255–645 K (vapor pressure eq., Yaws 1994) Henry’s Law Constant (Pa·m3/mol at 25°C or as indicated): 0.788 (volatility ratio-transpiration method, Andon et al. 1954) 0.784; 0.637; 0.749 (exptl.; calculated-group contribution; calculated-bond contribution, Hine & Mookerjee 1975) 1.836 (computed-vapor-liquid equilibrium VLE data, Yaws et al. 1991) 12.69 (20°C, selected from literature experimentally measured data, Staudinger & Roberts 2001) log KAW = –0.826 – 348/(T/K) (van’t Hoff eq. derived from literature data, Staudinger & Roberts 2001) Octanol/Water Partition Coefficient, log KOW: 1.20 (HPLC-RT correlation, Mirrlees et al. 1976) 1.20 ± 0.02 (shake flask at pH 7, Unger et al. 1978) 1.19 (HPLC-RT correlation, Lewis et al. 1983) 1.18 ± 0.01 (HPLC-RV correlation-ALPM, Garst 1984; Garst & Wilson 1984) 1.20 (shake flask, Log P Database, Hansch & Leo 1985, 1987) 1.20 (recommended, Sangster 1989, 1993) 1.20 (recommended, Hansch et al. 1995) Octanol/Air Partition Coefficient, log KOA: Bioconcentration Factor, log BCF: 0.699 (calculated-KOW, Lyman et al. 1982; quoted, Howard 1993) Sorption Partition Coefficient, log KOC: 2.029 (soil, calculated-KOW, Lyman et al. 1982; quoted, Howard 1993) Environmental Fate Rate Constants, k, or Half-Lives, t.: Volatilization: Photolysis: Oxidation: estimated photooxidation rate constant k = 1.43 . 10–12 cm3 molecule–1 s–1 for the vapor-phase reaction with 5 . 105 hydroxyl radicals/cm3 in air at 25°C which corresponds to an atmospheric half-life of 11 d (Atkinson 1987; quoted, Howard 1993). © 2006 by Taylor & Francis Group, LLC 3360 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals Hydrolysis: Biodegradation: Biotransformation: Bioconcentration, Uptake (k1) and Elimination (k2) Rate Constants: Half-Lives in the Environment: Air: atmospheric t. = 11 d from estimated photooxidation rate constant k = 1.43 . 10–12 cm3 ± molecule–1 s–1 for the vapor-phase reaction with 5 . 105 hydroxyl radicals/cm3 in air at 25°C (Atkinson 1987; quoted, Howard 1993). Surface water: estimated t. = 1.0 d for methylpyridine in Rhine River in case of a first order reduction process (Zoeteman et al. 1980) TABLE 16.1.7.5.1 Reported vapor pressures of 3-methylpyridine at various temperatures and the coefficients for the vapor pressure equations log P = A – B/(T/K) (1) ln P = A – B/(T/K) (1a) log P = A – B/(C + t/°C) (2) ln P = A – B/(C + t/°C) (2a) log P = A – B/(C + T/K) (3) log P = A – B/(T/K) – C·log (T/K) (4) Herington & Martin 1953 Scott et al. 1963(b) ebulliometry comparative ebulliometry t/°C P/Pa t/°C P/Pa 81.282 12871 74.036 9582 85.275 15061 77.115 10884 92.059 19478 80.202 12335 97.519 23773 85.303 13949 103.922 29747 86.403 15740 109.006 35349 89.524 17725 115.583 43796 92.658 19920 121.932 53445 98.946 25007 129.368 66822 105.270 31160 132.163 72471 111.640 38547 137.714 84938 118.052 47359 140.871 92693 124.508 57803 142.132 95948 131.008 70109 142.639 97265 137.551 84525 143.293 99017 144.135 101325 143.577 99782 150.767 120798 143.993 100927 157.441 143268 144.320 101791 164.156 169052 144.659 102725 170.918 198530 145.101 103988 177.821 232087 184.568 270110 bp/°C 144.143 .HV/(kJ mol–1) = 37.76 bp/°C 144.14 eq. 2 P/mmHg A 7.03247 Antoine B 1469.894 eq. 2 P/mmHg C 209.907 A 7.05375 B 1484.208 C 211.532 © 2006 by Taylor & Francis Group, LLC Nitrogen and Sulfur Compounds 3361 FIGURE 16.1.7.5.1 Logarithm of vapor pressure versus reciprocal temperature for 3-methylpyridine. 3-Methylpyridine: vapor pressure vs. 1/T 0.0 1.0 2.0 3.0 4.0 5.0 6.0 7.0 8.0 0.002 0.0022 0.0024 0.0026 0.0028 0.003 0.0032 1/(T/K) P( gol S ) aP/ Herington & Martin 1953 Scott et al. 1963b b.p. = 144.14 °C © 2006 by Taylor & Francis Group, LLC 3362 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals 16.1.7.6 2,3-Dimethylpyridine Common Name: 2,3-Dimethylpyridine Synonym: 2,3-lutidine Chemical Name: 2,3-dimethylpyridine, 2,3-lutidine CAS Registry No: 583-61-9 Molecular Formula: C7H9N, C5H3N(CH3)2 Molecular Weight: 107.153 Melting Point (°C): –15.5 (Stephenson & Malanowski 1987) Boiling Point (°C): 161.12 (Lide 2003) Density (g/cm3 at 20°C): 0.9461, 0.9421 (20°C, 25°C, Coulson et al. 1959) 0.9319 (25°C, Weast 1982–83) Molar Volume (cm3/mol): 115.0 (calculated-density, Stephenson & Malanowski 1987) 135.9 (calculated-Le Bas method at normal boiling point) Dissociation Constant, pK: 6.70 (20°C, Perrin 1972) 6.57 (pKa, Weast 1982–83) Enthalpy of Fusion, .Hfus (kJ/mol): Entropy of Fusion, .Sfus (J/mol K): Fugacity Ratio at 25°C (assuming .Sfus = 56 J/mol K), F: 1.0 Water Solubility (g/m3 or mg/L at 25°C or as indicated. Additional data at other temperatures designated * are compiled at the end of this section): 104000* (20°C, shake flask-GC, measured range 16–90°C, Stephenson 1993a) Vapor Pressure (Pa at 25°C and reported temperature dependence equations. Additional data at other temperatures designated * are compiled at the end of this section): 366.6, 922.6, 7119 (25, 40, 81.2°C, calculated-empirical method with bp and Antoine eq., Andon et al. 1954) 346.4* (ebulliometry, extrapolated-Antoine eq., measured range 99.5–162.4°C, Coulson et al. 1959) log (P/mmHg) = 7.05075 – 1528.935/(205.499 + t/°C); temp range 99.5–162.4°C (Antoine eq., ebulliometry, Coulson et al. 1959) 359.0 (calculated-Cox eq., Chao et al. 1983) log (P/atm) = [1– 434.216/(T/K)] . 10^{0.881714 – 6.74484 . 10–4 ± (T/K) + 5.55055 . 10–7 ± (T/K)2}; temp range: 260.0–655.0 K (Cox eq., Chao et al. 1983) 425.5 (extrapolated-Antoine eq., Boublik et al. 1984) log (P/kPa) = 6.45509 – 1739.902/(229.887 + t/°C); temp range 155.3–162.4°C (Antoine eq. from reported exptl. data of Coulson et al. 1959, Boublik et al. 1984) 352.2 (extrapolated-Antoine eq., Stephenson & Malanowski 1987) log (PL/kPa) = 6.18881 – 1538.772/(–66.477 + T/K); temp range; 372–476 K (Antoine eq., Stephenson & Malanowski 1987) 457 (extrapolated-Antoine eq., Dean 1992) log (P/mmHg) = 7.447 – 1832.6/(240.1 + t/°C); temp range 155–162°C (Antoine eq., Dean. 1992) 2000* (54.556°C, comparative ebulliometry, measured range 327.706–475.952 K, data fitted to Wagner eq., Steele et al. 1995) Henry’s Law Constant (Pa·m3/mol at 25°C or as indicated and reported temperature dependence equations): 0.725 (volatility ratio-transpiration method, Andon et al. 1954) 0.732 (exptl., Hine & Mookerjee 1975) N © 2006 by Taylor & Francis Group, LLC Nitrogen and Sulfur Compounds 3363 0.859, 0.732 (calculated.-group contribution, bond contribution, Hine & Mookerjee 1975) 21.01 (20°C, selected from literature experimentally measured data, Staudinger & Roberts 2001) log KAW = 0.039 – 617/(T/K), (van’t Hoff eq. derived from literature data, Staudinger & Roberts 2001) Octanol/Water Partition Coefficient, log KOW: Octanol/Air Partition Coefficient, log KOA: Bioconcentration Factor, log BCF: Sorption Partition Coefficient, log KOC: Environmental Fate Rate Constants, k, or Half-Lives, t.: Half-Lives in the Environment: Surface water: estimated t. = 13.0 d for dimethylpyridine in Rhine River in case of a first order reduction process (Zoeteman et al. 1980) TABLE 16.1.7.6.1 Reported aqueous solubilities and vapor pressures of 2,3-dimethylpyridine at various temperatures Aqueous solubility Vapor pressure Stephenson 1993a Coulson et al. 1959 Steele et al. 1995 shake flask-GC/TC ebulliometry comparative ebulliometry t/°C S/g·m–3 t/°C P/Pa T/K P/Pa 16.0 171500 99.543 14583 327.706 2000 18.0 121500 107.822 19765 333.396 2666 20.0 104000 116.337 26607 341.852 3999.9 25.0 86000 122.909 33113 348.166 5333 30.0 69100 128.606 39759 357.560 7998.9 35.0 59900 133.429 46191 364.611 10666 40.0 53700 137.704 52572 370.315 13332 50.0 48200 141.757 59255 376.239 16665 60.0 43700 145.829 66652 381.163 19933 70.0 43000 148.764 72421 387.649 25023 80.0 43300 152.203 79677 387.646 25023 90.0 43500 155.326 86769 394.176 31177 157.94 93067 400.749 38565 158.603 94703 407.364 47375 159.141 96085 414.025 57817 160.125 98614 420.729 70120 160.668 100030 427.477 84533 161.199 101438 434.270 101325 161.682 102701 441.106 120790 162.077 103788 447.989 143250 162.412 104696 454.913 169020 461.885 198490 mp/°C –15.22 468.897 232020 bp/°C 161.157 475.982 270020 .HV = 41.07 kJ/mol Antoine eq. Data fitted to Wagner eq. log P = A – B/(C + t/°C) P/mmHg A 7.05075 B 1528.935 C 205.499 © 2006 by Taylor & Francis Group, LLC 3364 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals FIGURE 16.1.7.6.1 Logarithm of mole fraction solubility (ln x) versus reciprocal temperature for 2,3-dimethylpyridine. FIGURE 16.1.7.6.2 Logarithm of vapor pressure versus reciprocal temperature for 2,3-dimethylpyridine. 2,3-Dimethylpyridine: solubility vs. 1/T -5.5 -5.0 -4.5 -4.0 -3.5 -3.0 -2.5 0.0026 0.0028 0.003 0.0032 0.0034 0.0036 0.0038 1/(T/K) x nl Stephenson 1993 2,3-Dimethylpyridine: vapor pressure vs. 1/T 0.0 1.0 2.0 3.0 4.0 5.0 6.0 7.0 8.0 0.002 0.0022 0.0024 0.0026 0.0028 0.003 0.0032 1/(T/K) P ( gol S ) aP / Coulson et al. 1959 Steele et al. 1995 b.p. = 161.12 °C © 2006 by Taylor & Francis Group, LLC Nitrogen and Sulfur Compounds 3365 16.1.7.7 Quinoline Common Name: Quinoline Synonym: benzo[b]-pyridine, 1-benzazine Chemical Name: quinoline CAS Registry No: 91-22-5 Molecular Formula: C9H7N Molecular Weight: 129.159 Melting Point (C): –14.78 (Lide 2003) Boiling Point (°C): 237.16 (Lide 2003) Density (g/cm3 at 20°C): 1.0929 (Weast 1982–83) 1.09771, 1.08579 (15, 30°C, Riddick et al. 1986) Molar Volume (cm3/mol): 118.1 (calculated-density, Rohrschneider 1973) 144.7 (calculated-Le Bas method at normal boiling point) Dissociation Constant, pK: 4.90 (pKa, 20°C, Weast 1982–83; Zachara et al. 1987; Matzner et al. 1991) 4.80 (pKa, protonated cation + 1, Dean 1985) 4.94 (pKBH + , Riddick et al. 1986) 4.87 (pKa, Sangster 1989) Enthalpy of Vaporization, .HV (kJ/mol): 49.71 (at bp, Riddick et al. 1986) Enthalpy of Fusion, .Hfus (kJ/mol): 10.79 (Riddick et al. 1986) Entropy of Fusion, .Sfus (J/mol K): Fugacity Ratio at 25°C (assuming .Sfus = 56 J/mol K), F: 1.0 Water Solubility (g/m3 or mg/L at 25°C or as indicated. Additional data at other temperatures designated * are compiled at the end of this section): 6110 (Albersmeyer 1958) 6840 (shake flask-HPLC/UV, Fu & Luthy 1985, 1986) 6386* (20.35°C, equilibrium cell-GC, measured range 20.35–225°C, Leet et al. 1987) 5426 (centrifuge-HPLC at pH 7 and pH 8, Matzner et al. 1991) 8400, 6600 (20°C, 30°C, shake flask-GC, Stephenson 1993a) Vapor Pressure (Pa at 25°C and reported temperature dependence equations. Additional data at other temperatures designated *, are compiled at the end of this section): 15.51* (extrapolated-regression of tabulated data, temp range 59.7–237.7°C, Stull 1947) 1.213 (extrapolated, Maczynski & Maczynska 1965) 11.20* (25.16°C, gas saturation-IR, measured range 12.62–35.9°C, Van De Rostyne & Prausnitz 1980) ln (P/mmHg) = 20.96 – 6993.2/(T/K); temp range 12.62–35.9°C (gas saturation-IR, Van De Rostyne & Prausnitz 1980) 11.14 (calculated-bp, Mackay et al. 1982) 12.83 (calculated-Cox eq., Chao et al. 1983) log (P/atm) = [1– 510.552/(T/K)] . 10^{0.897177 – 6.73559 . 10–4 ± (T/K) + 4.69070 . 10–7 ± (T/K)2}; temp range: 290.0–780.0 K (Cox eq., Chao et al. 1983) 11.04 (extrapolated-Antoine eq., Boublik et al. 1984) N © 2006 by Taylor & Francis Group, LLC 3366 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals log (P/kPa) = 5.94201 – 1668.355/(186.212 + t/°C), temp range 164.7–237.9°C (Antoine eq. from reported exptl. data, Boublik et al. 1984) 11.05 (extrapolated-Antoine eq., Dean 1985, 1992) log (P/mmHg) = 6.81759 – 1668.73/(186.26 + t/°C), temp range 164–238°C (Antoine eq., Dean 1985, 1992) 1.216 (recommended, Neely & Blau 1985) 12.8 (Howard et al. 1986) 11.2 (Riddick et al. 1986) log (P/kPa) = 5.92679 – 1656.30/(184.78 + t/°C); temp range not specified (Antoine eq., Riddick et al. 1986) 42120* (472.85 K, vapor-liquid equilibrium, measured range 472.85–548.05 K, Klara et al. 1987) log (P/kPa) = 14.4961 – 4390.0/(65.19 + T/K); temp range 472.85–548.05 K (vapor-liquid equilibrium, Klara et al. 1987) log (PL/kPa) = 5.92679 – 1656.3/(–88.37 + T/K); temp range 433–511 K (Antoine eq.-I, Stephenson & Malanowski 1987) log (PL/kPa) = 7.15102 – 2846.253/(41.795 + T/K); temp range 463–794 K (Antoine eq.-II, Stephenson & Malanowski 1987) 6.145 (calculated-solvatochromic parameters, Banerjee et al. 1990) log (P/mmHg) = 76.5432 – 5.7748 . 103/(T/K) –24.619·log (T/K) + 8.4666 . 10–3·(T/K) + 3.5586 . 10–13·(T/K)2; temp range 258–782 K (vapor pressure eq., Yaws 1994) Henry’s Law Constant (Pa m3/mol at 25°C): 0.0253 (calculated-P/C, Smith & Bomberger 1980) 0.026 (calculated-P/C, Mackay 1985) 0.168 (calculated-P/C, Meylan & Howard 1991) 0.0697 (estimated-bond contribution, Meylan & Howard 1991) Octanol/Water Partition Coefficient, log KOW: 2.03 (shake flask-UV, Iwasa et al. 1965) 2.06 (shake flask-UV at pH 7.4, Rogers & Cammarata 1969) 2.03 (Schultz et al. 1970) 2.04 (HPLC-RT correlation, Mirrlees et al. 1976) 2.04 ± 0.02 (shake flask at pH 7, Unger et al. 1978) 2.02 (Hansch & Leo 1979) 2.01 ± 0.02 (HPLC-RV correlation-ALPM, Garst & Wilson 1984) 1.88 (HPLC-k. correlation, Haky & Young 1984) 2.20 (calculated-activity coeff. . from UNIFAC, Banerjee & Howard 1988) 2.10 (shake flask-HPLC, De Voogt et al. 1988, 1990) 2.09 (28°C, shake flask-UV at pH 7.4, Go & Ngiam 1988) 2.03 (recommended, Sangster 1989, 1993) 2.10, 2.15 (HPLC-RT correlation, shake flask-electrometric titration, Slater et al. 1994) 2.03 (recommended, Hansch et al. 1995) 2.17 ± 0.66, 2.33 ± 0.56 (HPLC-k. correlation: ODS–65 column, Diol–35 column, Helweg et al. 1997) 1.91 (microemulsion electrokinetic chromatography-retention factor correlation, Jia et al. 2003) Octanol/Air Partition Coefficient, log KOA: Bioconcentration Factor, log BCF: Sorption Partition Coefficient, log KOC: 1.04 (Coyote Creek sediment with organic content of 1.9%, Smith et al. 1978) 1.96, 2.10, 1.67, 1.72 (estimated-KOW, Karickhoff 1985) 1.42, 1.62 (estimated-S, Karickhoff 1985) 2.20 (best estimate, Karickhoff 1985) 0.251 (estimated Anvil Points subsurface materials, Zachara et al. 1987) –1.516 (estimated Loring subsurface materials, Zachara et al. 1987) 2.89; 3.05 (humic acid, HPLC-k. correlation; quoted lit., Nielsen et al. 1997) © 2006 by Taylor & Francis Group, LLC Nitrogen and Sulfur Compounds 3367 Environmental Fate Rate Constants, k, or Half-Lives, t.: Volatilization: t. = 7000 h in stream, t. = 35000 h in eutrophic pond and t. = 28000 h in eutrophic lake and oligotrophic lake, based on transformation and transport of quinoline predicted by the one-compartment model (Smith et al. 1978). Photolysis: k = 7.8 . 10–7 s–1, assuming exposed to 12-h sunlight per day in June, photolysis t. = 1200 h in stream, t. = 3000 h in eutrophic lake and pond and t. = 600 h in oligotrophic lake, based on transformation and transport of quinoline predicted by the one-compartment model (Smith et al. 1978) k(aq.) = 3.6 . 10–7 s–1 for summer with t. = 535 h and k = 5.0 . 10–8 s–1 for winter with t. = 3851 h both at pH 6.9 and under sunlight at 40°N (Mill et al. 1981; quoted, Howard et al. 1991) photolytic t. = 550 h in aquatics (Haque et al. 1980) t. = 5–12 d for disappearance via direct photolysis in aqueous media (Harris 1982) Oxidation: k = 2.8 M–1 s–1 for the reaction with RO2 radical with t. > 104 h in stream, eutrophic pond and lake and oligotrophic lake, based on RO2 concentration of 10–9 M on transformation and transport of quinoline predicted by the one-compartment model (Smith et al. 1978) k(aq.) = 3.5 . 10–7 s–1 with t. = 548 h under natural sunlight conditions for midday, midsummer at a latitude of 40°N; k(aq.) = 2.8 M–1 s–1 with t. = 8 yr for free-radical oxidation in air-saturated water (NRCC 1983) photooxidation t. = 10–99 h in air, based on an estimated rate constant for vapor phase reaction with hydroxyl radicals in air (Atkinson 1987; quoted, Howard et al. 1991) first-order photodegradation k = 8.0 . 10–6 s–1 at 313 nm of in organic-free water with t. = 24.0 h and k = 8.4 . 10–6 s–1 in lake water with t. = 23 h both saturated with air (Kochany & Maguire 1994) Hydrolysis: no hydrolyzable groups (Howard et al. 1991). Biodegradation: t. = 0.5 h in stream, eutrophic lake and pond and t. = 10000 h in oligotrophic lake, based on transformation and transport of quinoline predicted by the one-compartment model (Smith et al. 1978); Biodegradation k = 7.4 . 10–5 mL cell–1 d–1 in enrichment culture (Klecka 1985); t.(aq. aerobic) = 72–240 h, based on an acclimated fresh water grab sample data (Rogers et al. 1984; quoted, Howard et al. 1991); t.(aq. anaerobic) = 288–960 h, based on estimated aqueous aerobic biodegradation half-life (Howard et al. 1991) Biotransformation: Bioconcentration, Uptake (k1) and Elimination (k2) Rate Constants: Half-Lives in the Environment: Air: t. = 10 – 99 h, based on an estimated rate constant for vapor phase reaction with hydroxyl radicals in air (Atkinson 1987; selected, Howard et al. 1991); atmospheric transformation lifetime was estimated to be 1 to 5 d (Kelly et al. 1994). Surface water: half-life for all processes, except for dilution: t. = 0.5 h in stream, eutrophic lake and pond and t. = 600 h in oligotrophic lake, based on transformation and transport of quinoline predicted by the onecompartment model (Smith et al. 1978); half-life for all processes, including for dilution: t. = 0.28 h in stream, t. = 0.5 h in eutrophic lake and pond and t. = 600 h in oligotrophic lake, based on transformation and transport of quinoline predicted by the one-compartment model (Smith et al. 1978); t. = 5 – 12 d for direct photolysis in aqueous media (Harris 1982); t. = 72 – 240 h, based on an acclimated fresh water grab sample data (Rogers et al. 1984; quoted, Howard et al. 1991); degrade readily in sunlight in near surface lake water at 40°N latitude in summer with a t. ~ 14 calendar-d while its t.(calc) ~ 123 calendar-d in winter (Kochany & Maguire 1994). Groundwater: t. = 144 – 480 h, based on estimated aqueous aerobic biodegradation half-life (Howard et al. 1991). Sediment: Soil: t. = 72 – 240 h, based on estimated aqueous aerobic biodegradation half-life (Howard et al. 1991) Complete mineralization within 7 – 10 d in batch experiments independent of pH (5.8 and 7.2) (Thomsen et al. 1999) Biota: © 2006 by Taylor & Francis Group, LLC 3368 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals TABLE 16.1.7.7.1 Reported aqueous solubilities and vapor pressures of quinoline at various temperatures and the coefficients for the vapor pressure equations: Vapor pressure Aqueous solubility Stull 1947 Van De Rostyne & Prausnitz Klara et al. 1987 Leet et al. 1987 summary of literate data gas saturation-IR (1980) vapor-liquid equilibrium equilibrium cell-GC t/°C P/Pa t/°C P/Pa T/K P/Pa t/°C S/g·m–3 59.7 133.3 12.62 3.853 472.85 42120 20.35 6386 89.6 666.6 16.71 5.963 504.95 90990 40.05 6458 103.8 1333 21.35 8.159 514.35 112400 64.85 8252 119.8 2666 22.42 9.56 534.35 170300 80.25 10620 136.7 5333 25.16 11.20 548.05 222600 100.05 13920 148.1 7999 28.25 14.80 120.65 20163 163.2 13332 29.10 14.93 eq. 3 P/kPa 145.85 31285 186.2 26664 35.90 24.26 log P = A – B/(C + T/K) 159.65 43555 212.3 53329 A 14.4961 179.85 69602 237.7 101325 eq. 1a P/mmHg B 4390.0 199.25 126288 ln P = A – B/(T/K) C 65.19 209.05 171494 mp/°C –15.0 A 20.96 220.25 324333 B 6993.2 225.05 498697 FIGURE 16.1.7.7.1 Logarithm of vapor pressure versus reciprocal temperature for quinoline. Quinoline: vapor pressure vs. 1/T 0.0 1.0 2.0 3.0 4.0 5.0 6.0 7.0 8.0 0.0018 0.0022 0.0026 0.003 0.0034 0.0038 1/(T/K) P( gol S ) aP/ Van De Rostyne & Prausnitz 1980 Klara et al. 1987 Stull 1947 b.p. = 237.16 °C © 2006 by Taylor & Francis Group, LLC Nitrogen and Sulfur Compounds 3369 16.1.7.8 Isoquinoline Common Name: Isoquinoline Synonym: leucoline Chemical Name: isoquinoline CAS Registry No: 119-65-3 Molecular Formula: C9H7N Molecular Weight: 129.159 Melting Point (°C): 26.47 (Lide 2003) Boiling Point (°C): 243.22 (Lide 2003) Density (g/cm3 at 20°C): 1.0986 (Weast 1982–83) 1.0910 (Dean 1985) Molar Volume (cm3/mol): 118.4 (30°C, Stephenson & Malanowski 1987) 144.7 (calculated-Le Bas method at normal boiling point) Dissociation Constant, pK: 5.40 (pKa, Perrin 1972) 5.42 (pKa, 20°C, Weast 1982–83) 5.40 (pKa, protonated cation + 1, Dean 1985) 5.38 (pKBH + , Riddick et al. 1986) 5.39 (pKa, Sangster 1989) Enthalpy of Vaporization, .HV (kJ/mol): 48.96 (bp, Riddick et al. 1986) Enthalpy of Fusion, .Hfus (kJ/mol): 7.448 (Riddick et al. 1986) Entropy of Fusion, .Sfus (J/mol K): Fugacity Ratio at 25°C (assuming .Sfus = 56 J/mol K), F: 0.967 (mp at 26.47°C) Water Solubility (g/m3 or mg/L at 25°C): 4520 (Pearlman et al. 1984) Vapor Pressure (Pa at 25°C and reported temperature dependence equations. Additional data at other temperatures designated * are compiled at the end of this section): 11.8* (extrapolated-regression of tabulated data, temp range 63.5–240.5°C, Stull 1947) 7.80 (extrapolated-Cox eq., Chao et al. 1983) log (P/atm) = [1– 516.182/(T/K)] . 10^{0.91210 – 6.33889 . 10–4 ± (T/K) + 4.267359 . 10–7 ± (T/K)2}; temp range: 300.0–800.0 K (Cox eq., Chao et al. 1983) 6.33 (extrapolated-Antoine eq., Boublik et al. 1984) log (P/kPa) = 6.03709 – 1723.459/(184.268 + t/°C); temp range 166–244°C (Antoine eq. from reported exptl. data, Boublik et al. 1984) 6.35 (extrapolated-Antoine eq., Dean 1985, 1992) log (P/mmHg) = 6.9122 – 1723.4/(184.3 + t/°C); temp range 167–244°C (Antoine eq., Dean 1992) 6.70 (Riddick et al. 1986) log (PL/kPa) = 6.03203 – 1719.5/(–89.12 + T/K); temp range 439–517 K (Antoine eq., Stephenson & Malanowski 1987) log (P/mmHg) = 45.5737 – 4.4715 . 103/(T/K) –13.308·log (T/K) + 4.0186 . 10–3·(T/K) – 6.4589 . 10–14·(T/K)2; temp range 299–803 K (vapor pressure eq., Yaws 1994) N © 2006 by Taylor & Francis Group, LLC 3370 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals Henry’s Law Constant (Pa·m3/mol at 25°C): 19.14 (calculated-P/C with selected values) Octanol/Water Partition Coefficient, log KOW: 2.08 (shake flask-UV, Hansch & Anderson 1967) 2.09 (HPLC-RT correlation, Mirrlees et al. 1976) 2.08 (recommended, Sangster 1989, 1993) 2.30 ± 0.15, 2.17 ± 0.53 (solvent generated liquid-liquid chromatography SGLLC-correlation, RP-HPLC-k. correlation, Cichna et al. 1995) 2.08 (recommended, Hansch et al. 1995) 2.21 ± 0.66, 2.2 6 ± 0.56 (HPLC-k. correlation: ODS-65 column, Diol-35 column, Helweg et al. 1997) Octanol/Air Partition Coefficient, log KOA: Bioconcentration Factor, log BCF: Sorption Partition Coefficient, log KOC: 3.09 (humic acid, HPLC-k. correlation, Nielsen et al. 1997) Environmental Fate Rate Constants, k, or Half-Lives, t.: Bioconcentration, Uptake (k1) and Elimination (k2) Rate Constants: k1 = 82.0 h–1, k2 = 34.2 h–1 (daphnia pulex, 21°C, Southworth et al. 1978) Half-Lives in the Environment: Biota: elimination t. = 1 min (daphnia pulex, Southworth et al. 1978). TABLE 16.1.7.8.1 Reported vapor pressures of isoquinoline at various temperatures Stull 1947 summary of literature data t/°C P/Pa 63.5 133.3 92.7 666.6 107.8 1333 123.7 2666 141.6 5333 152.0 7999 167.6 13332 190.0 26664 214.5 53329 240.5 101325 mp/°C 24.5 © 2006 by Taylor & Francis Group, LLC Nitrogen and Sulfur Compounds 3371 FIGURE 16.1.7.8.1 Logarithm of vapor pressure versus reciprocal temperature for isoquinoline. Isoquinoline: vapor pressure vs. 1/T 0.0 1.0 2.0 3.0 4.0 5.0 6.0 7.0 8.0 0.0018 0.0022 0.0026 0.003 0.0034 0.0038 1/(T/K) P( gol S ) aP/ Stull 1947 b.p. = 243.22 °C m.p. = 26.47 °C © 2006 by Taylor & Francis Group, LLC 3372 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals 16.1.7.9 Benzo[f]quinoline Common Name: Benzo[f]quinoline Synonym: 5,6-benzoquinoline, naphthopyridine Chemical Name: 5,6-benzoquinoline, benzo(f)quinoline CAS Registry No: 85-02-9 Molecular Formula: C13H9N Molecular Weight: 179.217 Melting Point (°C): 94 (Lide 2003) Boiling Point (°C): 352 (Lide 2003) Density (g/cm3 at 20°C): Molar Volume (cm3/mol): 196.3 (calculated-Le Bas method at normal boiling point) Dissociation Constant, pK: 5.15 (Sangster 1993) Enthalpy of Fusion, .Hfus (kJ/mol): Entropy of Fusion, .Sfus (J/mol K): Fugacity Ratio at 25°C (assuming .Sfus = 56 J/mol K), F: 0.210 (mp at 94°C) Water Solubility (g/m3 or mg/L at 25°C): 76.1 (shake flask-GC, Smith et al. 1978) 77.1 (Mill et al. 1981) l76.0 (Steen & Karickhoff 1981) 78.7 (average literature value, Pearlman et al. 1984) Vapor Pressure (Pa at 25°C or as indicated and reported temperature dependence equations. Additional data at other temperatures designated * are compiled at the end of this section): 0.00747* (25.05°C, gas saturation, measured range 288.26–323.15 K, McEachern et al. 1975) log (P/mmHg) = 4339.977/(T/K) + 10.2555; temp range 288.26–323.15 K (Antoine eq., gas saturation, McEachern et al. 1975 0.00670 (interpolated-Antoine eq., Stephenson & Malanowski 1987) log (PL/kPa) = 9.37682 – 4338.411/(T/K); temp range 288–323 K (Antoine eq., Stephenson & Malanowski 1987) Henry’s Law Constant (Pa·m3/mol at 25°C): 0.0096 (calculated-P/C, Smith & Bomberger 1980) Octanol/Water Partition Coefficient, log KOW: 3.20 (Steen & Karickhoff 1981) 3.40 (TLC-RT correlation, De Voogt et al. 1988) 3.25 (23°C, shake flask-HPLC, pH 7, De Voogt et al. 1990) 3.25, 3.40 (lit. values; Sangster 1993) 3.46 ± 0.64, 3.51 ± 0.53 (HPLC-k. correlation: ODS-65 column, Diol-35 column, Helweg et al. 1997) Octanol/Air Partition Coefficient, log KOA: Bioconcentration Factor, log BCF: 2.18 (mixed microbial populations, Steen & Karickhoff 1981) N © 2006 by Taylor & Francis Group, LLC Nitrogen and Sulfur Compounds 3373 Sorption Partition Coefficient, log KOC: 3.11 (Coyote Creek sediment, Smith et al. 1978) 4.64, 4.32 (soil, quoted, calculated-MCI . and fragment contribution, Meylan et al. 1992) 4.07 (humic acid, HPLC-k. correlation, Nielsen et al. 1997) Environmental Fate Rate Constants, k, or Half-Lives, t.: Volatilization: estimated t. > 10000 h in river, t. > 100000 h in eutrophic pond, eutrophic lake and oligotrophic lake by the one compartment model (Smith et al. 1978). Photolysis: k = (1.4 ± 0.7) . 10–4 s–1 for transformation and transport when exposed to 12 h sunlight in mid-June with estimated t. = 2.8 h in river, t. = 7.0 h in eutrophic pond and eutrophic lake and t. = 1.4 h in oligotrophic lake from average photolysis rates on a summer day at 40°N latitude by the one compartment model (Smith et al. 1978) photolytic t. = 0.52 h in aquatics (Haque et al. 1980) t. = 1 h for disappearance via direct photolysis in aqueous media (Harris 1982) Oxidation: laboratory studied k < 2.8 M–1 s–1 for the reaction with the RO2 radicals and estimated t. > 105 h in river, eutrophic pond, eutrophic lake and oligotrophic lake by the one compartment model (Smith et al. 1978) k(aq.) = 3.7 . 10–4 s–1 with t. = 0.5 h under natural sunlight conditions for midday, midsummer at a latitude of 40°N; k(aq.) < 2.8 M–1 s–1 with t. > 8 yr for free-radical oxidation in air-saturated water (NRCC 1983) Hydrolysis: Biodegradation: estimated t. = 190 h in river, eutrophic pond, eutrophic lake and t. > 106 h in oligotrophic lake by the one compartment model (Smith et al. 1978). Biotransformation: Bioconcentration, Uptake (k1) and Elimination (k2) Rate Constants: Half-Lives in the Environment: Surface water: t. = 0.5 h in river water, t. = 6.9 h in pond water, t. = 7.0 h in eutrophic lake and t. = 1.4 h in oligotrophic lake predicted by one-compartment for all processes including dilution (Smith et al. 1978) t. = 1 h for disappearance via direct photolysis in aqueous media (Harris 1982). TABLE 16.1.7.9.1 Reported vapor pressures of benzo[f]quinoline at various temperatures McEachern et al. 1975 gas saturation T/K P/Pa 288.26 0.00213 293.10 0.00333 298.20 0.00747 303.13 0.0116 308.23 0.0199 313.17 0.0324 318.24 0.0560 323.15 0.0901 P/mmHg log P = A – B/(T/K) A 10.2555 B 4399.977 .Hsubl/(kJ mol–1) = 83.094 .Ssubl/(J mol–1 K–1) = 196.36 © 2006 by Taylor & Francis Group, LLC 3374 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals FIGURE 16.1.7.9.1 Logarithm of vapor pressure versus reciprocal temperature for benzo[f]quinoline. Benzo[f ]quinoline: vapor pressure vs. 1/T -5.0 -4.0 -3.0 -2.0 -1.0 0.0 1.0 2.0 3.0 0.0026 0.0028 0.003 0.0032 0.0034 0.0036 1/(T/K) P( gol S ) aP/ McEachern et al. 1975 m.p. = 94 °C © 2006 by Taylor & Francis Group, LLC Nitrogen and Sulfur Compounds 3375 16.1.7.10 Carbazole Common Name: Carbazole Synonym: 9H-carbazole, dibenzopyrrole Chemical Name: carbazole CAS Registry No: 86-74-8 Molecular Formula: C12H9N, C6H4NHC6H4 Molecular Weight: 167.206 Melting Point (°C): 246.3 (Lide 2003) Boiling Point (°C): 354.69 (Lide 2003) Density (g/cm3 at 20°C): 1.260 (25°C, Jimenez et al. 1990) Molar Volume (cm3/mol): 192.9 (calculated-Le Bas method at normal boiling point) Enthalpy of Fusion, .Hfus (kJ/mol): Entropy of Fusion, .Sfus (J/mol K): Fugacity Ratio at 25°C (assuming .Sfus = 56 J/mol K), F: 0.00674 (mp at 246.3°C) Water Solubility (g/m3 or mg/L at 25°C): 1.03 ± 0.05 (20°C, shake flask-GC, Smith et al. 1978) 1.037 (Mill et al. 1981) 0.428 (20°C, shake flask-fluorophotometry, Hashimoto et al. 1982) 1.67, 1.03, 0.908; 1.204 (quoted values; lit. average, Pearlman et al. 1984) Vapor Pressure (Pa at 25°C and reported temperature dependence equations. Additional data at other temperatures designated * are compiled at the end of this section): 7999* (248.2°C, summary of literature data, temp range: 248.2–354.8°C, Stull 1947) log (P/mmHg) = [–0.2185 . 15421.6/(T/K)] + 8.251923; temp range: 248.2–354.8°C (Antoine eq., Weast 1972–73) 0.0933 (20°C, Smith et al. 1978) log (P/atm) = [1 – 627.897/(T/K)] . 10^{0.924810 – 5.18974 . 10–4 ± (T/K) + 2.68415 . 10–7 ± (T/K)2}; temp range: 518.0–631.0 K (Cox eq., Chao et al. 1983) 0.00424 (extrapolated-Antoine eq., Boublik et al. 1984) log (P/kPa) = 6.20101 – 2169.73/(162.465 + t/°C); temp range 252.6–357.3°C (Antoine eq. from reported exptl. data, Boublik et al. 1984) log (P/mmHg) = 7.0863 – 2179.4/(163.5 + t/°C); temp range 253–368°C (Antoine eq., Dean 1985, 1992) 0.0012 (Antoine eq.-I, Stephenson & Malanowski 1987) 0.0045 (liquid, extrapolated-Antoine eq.-II, Stephenson & Malanowski 1987) log (PS/kPa) = 10.1069 – 4780/(T/K); temp range not specified (solid, Antoine eq.-I, Stephenson & Malanowski 1987) log (PL/kPa) = 6.21123 – 2179.424/(–109.636 + T/K); temp range 525–631 K (liquid, Antoine eq-II., Stephenson & Malanowski 1987) 0.0002* (extrapolated-Antoine eq., Knudsen effusion, measured range 73.43–90.80°C, Jimenez et al. 1990) log (P/Pa) = 14.64– 5288.4/(T/K); temp range 73.43–90.80°C (Knudsen effusion, Jimenez et al. 1990) log (P/mmHg) = –119.857 – 3.2537 . 103/(T/K) + 52.568·log (T/K) – 4.6797 . 10–2·(T/K) + 1.4113 . 10–5·(T/K)2; temp range 518–899 K (vapor pressure eq., Yaws 1994) NH © 2006 by Taylor & Francis Group, LLC 3376 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals Henry’s Law Constant (Pa·m3/mol at 25°C): 16.0 (calculated-P/C, Smith & Bomberger 1980) Octanol/Water Partition Coefficient, log KOW: 3.29 (shake flask-UV at pH 7.4, Rogers 1969) 3.01 (HPLC-k. correlation, Eadsforth 1986) 3.50 (calculated, Eadsforth 1986) 3.72 (recommended, Sangster 1989, 1993) 3.59 (HPLC-RT correlation, Jenke et al. 1990) 3.84 (shake flask-HPLC at pH 7, De Voogt et al. 1988) 3.47 ± 0.63, 3.22 ± 0.53 (HPLC-k. correlation: ODS-65 column, Diol-35 column, Helweg et al. 1997) 3.72 (recommended, Hansch et al. 1995) Octanol/Air Partition Coefficient, log KOA: Bioconcentration Factor, log BCF: Sorption Partition Coefficient, log KOC: 2.24 (Coyote Creek sediment, Smith et al. 1978) 4.74 (humic acid, HPLC-k. correlation, Nielsen et al. 1997) 3.80 (soil-pore water partition coeff., Askov soil - a Danish agricultural soil, Sverdrup et al. 2002) Environmental Fate Rate Constants, k, or Half-Lives, t.: Volatilization: estimated t. > 105 h in river, eutrophic pond, eutrophic lake and oligotrophic lake by the one compartment model (Smith et al. 1978). Photolysis: k = 6.6 . 10–5 s–1 for transformation and transport when exposed to midday sunlight in late January with estimated t. = 6.0 h in river, t. = 15.0 h in eutrophic pond and eutrophic lake and t. = 3.0 h in oligotrophic lake from average photolysis rates on a summer day at 40°N latitude by the one compartment model (Smith et al. 1978) photolytic t. = 1.0 h in aquatics (Haque et al. 1980) t. = 3 h for disappearance via direct photolysis in aquatic media (Harris 1982). Oxidation: laboratory investigated k = 29 M–1 s–1 for the reaction with RO2 radicals and estimated t. > 240 h in river, eutrophic pond, eutrophic lake and oligotrophic lake by the one compartment model (Smith et al. 1978) k(aq.) = 1.9 . 10–4 s–1 with t. = 1.0 h under natural sunlight conditions for midday, midsummer at a latitude of 40°N; k(aq.) = 29 M–1 s–1 with t. = 280 yr for free-radical oxidation in air-saturated water (NRCC 1983) Hydrolysis: Biodegradation: estimated half-lives of 14 h in river, eutrophic pond, eutrophic lake and > 103 h in oligotrophic lake by the one compartment model (Smith et al. 1978). Biotransformation: Bioconcentration, Uptake (k1) and Elimination (k2) Rate Constants: Half-Lives in the Environment: Surface water: estimated t. = 6.0 h in river, t. = 15.0 h in eutrophic pond and eutrophic lake and t. = 3.0 h in oligotrophic lake from average photolysis rates on a summer day at 40°N latitude by the one compartment model (Smith et al. 1978); photolytic t. = 1.0 h in aquatics (Haque et al. 1980); t. = 3 h for disappearance via direct photolysis in aquatic media (Harris 1982). © 2006 by Taylor & Francis Group, LLC Nitrogen and Sulfur Compounds 3377 TABLE 16.1.7.10.1 Reported vapor pressures of carbazole at various temperatures and the coefficients for the vapor pressure equations log P = A – B/(T/K) (1) ln P = A – B/(T/K) (1a) log P = A – B/(C + t/°C) (2) ln P = A – B/(C + t/°C) (2a) log P = A – B/(C + T/K) (3) log P = A – B/(T/K) – C·log (T/K) (4) Stull 1947 Jimenez et al. 1990 summary of literature data Knudsen effusion t/°C P/Pa t/°C P/Pa 248.2 7999 73.43 0.0610 265.0 13332 78.72 0.101 292.5 26664 81.0 0.129 323.0 53329 83.59 0.167 354.8 101325 86.67 0.219 87.13 0.227 mp/°C 244.8 90.80 0.329 . (at 25°C) 1.26 g/cm3 eq. 1 P/Pa A 14.04 B 5288.4 enthalpy of sublimation: .Hsub/(kJ mol–1) = 103.3 at 25°C FIGURE 16.1.7.10.1 Logarithm of vapor pressure versus reciprocal temperature for carbazole. Carbazole: vapor pressure vs. 1/T -2.0 -1.0 0.0 1.0 2.0 3.0 4.0 5.0 6.0 0.001 0.0014 0.0018 0.0022 0.0026 0.003 0.0034 1/(T/K) log(PS /Pa) Jimenez et al. 1990 Stull 1947 m.p. = 246.3 °C b.p. = 354.7 °C © 2006 by Taylor & Francis Group, LLC 3378 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals 16.1.7.11 Benzo[c,g]carbazole Common Name: Benzo[c,g]carbazole Synonym: 7H-dibenzo[c,g]carbazole Chemical Name: 7H-dibenzo[c,g]carbazole CAS Registry No: 194-59-2 Molecular Formula: C20H13N, C10H6NHC10H6 Molecular Weight: 267.324 Melting Point (°C): 158 (Lide 2003) Boiling Point (°C) Density (g/cm3 at 20°C): Molar Volume (cm3/mol): 296.1 (calculated-Le Bas method at normal boiling point) Dissociation Constant, pKa: Enthalpy of Fusion, .Hfus (kJ/mol): Entropy of Fusion, .Sfus (J/mol K): Fugacity Ratio at 25°C (assuming .Sfus = 56 J/mol K), F: 0.0496 (mp at 158°C) Water Solubility (g/m3 or mg/L at 25°C): 0.063 ± 0.003 (shake flask-GC, Smith et al. 1978) 0.064 (Mill et al. 1981) 0.064 (Pearlman et al. 1984) Vapor Pressure (Pa at 25°C): 1.33 . 10–7 (estimated by comparison with benzo[a]pyrene, Smith et al. 1978) Henry’s Law Constant (Pa·m3/mol at 25°C): 0.00048 (calculated-P/C, Smith & Bomberger 1980) Octanol/Water Partition Coefficient, log KOW: 5.75 (calculated-S, Steen & Karickhoff 1981) Octanol/Air Partition Coefficient, log KOA: Bioconcentration Factor, log BCF: 4.93 (mixed microbial populations, Steen & Karickhoff 1981) Sorption Partition Coefficient, log KOC: 4.31 (Coyote Creek sediment, Smith et al. 1978) 6.03, 6.16 (soil, quoted, calculated-MCI . and fragment contribution, Meylan et al. 1992) Environmental Fate Rate Constants, k, or Half-Lives, t.: Volatilization: estimated t. = 15000 h in river, t. = 37000 h in eutrophic pond, t. = 73000 h in eutrophic lake and oligotrophic lake by the one compartment model (Smith et al. 1978). Photolysis: rate constant k = 5.2 . 10–4 s–1 for transformation and transport when exposed to midday sunlight in mid-January with estimated t. = 1.0 h in river, t. = 1.5 h in eutrophic pond and eutrophic lake and t. = 0.5 h in oligotrophic lake assuming winter insulation by the one compartment model (Smith et al. 1978) photolytic t. = 0.35 h in aquatics (Haque et al. 1980). NH © 2006 by Taylor & Francis Group, LLC Nitrogen and Sulfur Compounds 3379 Oxidation: laboratory studied k = 830 M–1 s–1 for the reaction with the RO2 radicals and estimated t. > 700 h in river, eutrophic pond, eutrophic lake and oligotrophic lake by the one compartment model (Smith et al. 1978) k = 5.5 . 10–4 s–1 with t. = 0.4 d under natural sunlight conditions for midday, midsummer at a latitude of 40°N; k = 830 M–1 s–1 with t. = 10 d for free-radical oxidation in air-saturated water (NRCC 1983) Hydrolysis: Biodegradation: estimated half-life to be very long in river, eutrophic pond, eutrophic lake and oligotrophic lake by the one compartment model with no acclimated cultures obtained during the screening studies (Smith et al. 1978). Biotransformation: Bioconcentration, Uptake (k1) and Elimination (k2) Rate Constants: Half-Lives in the Environment: Surface water: t. = 0.36 h in river water, t. = 1.5 h in pond water, t. = 1.5 h in eutrophic lake and t. = 0.5 h in oligotrophic lake for all processes predicted by one-compartment model (Smith et al. 1981); t. = 10 d for free-radical oxidation in air-saturation water (NRCC 1983). © 2006 by Taylor & Francis Group, LLC 3380 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals 16.1.7.12 Acridine Common Name: Acridine Synonym: 2,3,5,6-dibenzopyridine Chemical Name: acridine, 2,3,5,6-dibenzopyridine CAS Registry No: 260-94-6 Molecular Formula: C13H9N Molecular Weight: 179.217 Melting Point (°C): 110 (Lide 2003) Boiling Point (°C): 344.86 (Lide 2003) Density (g/cm3 at 20°C): 1.005 (Weast 1982–83) Molar Volume (cm3/mol): 196.3 (calculated-Le Bas method at normal boiling point) Dissociation Constant, pKa: 5.60 (Albert 1966; Matzner et al. 1991; Matzner & Bales 1994) 5.58 (20°C, Weast 1982–83) 5.60 (protonated cation + 1, Dean 1985) 10.65 (Sangster 1989) Enthalpy of Fusion, .Hfus (kJ/mol): 18.58 ± 0.38 (McEachern et al. 1975) Entropy of Fusion, .Sfus (J/mol K): Fugacity Ratio at 25°C (assuming .Sfus = 56 J/mol K), F: 0.147 (mp at 110°C) Water Solubility (g/m3 or mg/L at 25°C or as indicated): 57.4 (Albert 1966) 38.4 (24°C, shake flask-LSC, Means et al. 1980) 46.6 (literature average, Pearlman et al. 1984) 54.8 (centrifuge-HPLC at pH 8, Matzner et al. 1991) Vapor Pressure (Pa at 25°C and reported temperature dependence equations. Additional data at other temperatures designated * are compiled at the end of this section): 133.3* (129.4°C, summary of literature data, temp range 129.4–346°C, Stull 1947) log (P/mmHg) = [–0.2185 . 15174.6/(T/K)] + 8.251980; temp range 129.4–346°C (Antoine eq., Weast 1972–73) 0.0065* (Langmuir free evaporation, measured range 7.96–50°C, McEachern et al. 1975) log (P/mmHg) = 27.076 – 11021.64/(T/K); measured range 281.2–323.3 K (Langmuir free evaporation, McEachern et al. 1975) 0.0075 (extrapolated-Cox eq., Chao et al. 1983) log (P/atm) = [1 – 618.827/(T/K)] . 10^{0.839996 – 4.19344 . 10–4 ± (T/K) + 3.63487 . 10–7 ± (T/K)2}; temp range: 402.6–619.2 K (Cox eq., Chao et al. 1983) 0.2066 (static apparatus-extrapolated from Chebyshev polynomials, Sivaraman & Kobayashi 1983) 0.0065 (Interpolated-Antoine eq.-I, Stephenson & Malanowski 1987; quoted, Ma et al. 1990) N © 2006 by Taylor & Francis Group, LLC Nitrogen and Sulfur Compounds 3381 log (PS/kPa) = 8.30838 – 3365.943/(–48.723 + T/K); temp range 293–367 K (solid, Antoine eq.-I, Stephenson & Malanowski 1987) log (PL/kPa) = 6.73664 – 2699.39/(–48.611 + T/K); temp range 402–619 K (liquid, Antoine eq.-II, Stephenson & Malanowski 1987) Henry’s Law Constant (Pa·m3/mol at 25°C): 0.030 (calculated-P/C, Ma et al. 1990) Octanol/Water Partition Coefficient, log KOW: 3.40 (shake flask-UV, Hansch & Fujita 1964) 3.39 (HPLC-RT correlation, Mirrlees et al. 1976) 3.39 (shake flask at pH 7.4, Unger et al. 1978) 3.62 (shake flask-LSC, Means et al. 1980) 3.29 (shake flask-AS at pH 7.4, Unger & Chiang 1981) 3.31 ± 0.03 (HPLC-RV correlation-ALPM, Garst 1984) 3.35 ± 0.02 (HPLC-RV correlation-ALPM, Garst & Wilson 1984) 3.32 (shake flask-GC at pH 7.0, Haky & Leja 1986) 3.40 (recommended, Sangster 1989, 1993) 3.40 (recommended, Hansch et al. 1995) 3.18 ± 0.64, 3.27 ± 0.53 (HPLC-k. correlation: ODS-65 column, Diol-35 column, Helweg et al. 1997) Octanol/Air Partition Coefficient, log KOA: Bioconcentration Factor, log BCF: 2.40 (selected, Ma et al. 1990) Sorption Partition Coefficient, log KOC: 4.69 (average of sediments and soil samples, equilibrium sorption isotherm, Means et al. 1980) 3.32 (calculated, Means et al. 1980) –0.157 (estimated of Loring subsurface material, Zachara et al. 1987) 0.610 (estimated of Anvil Points subsurface material, Zachara et al. 1987) 3.09–3.41 (soil, calculated-KOW, model of Karickhoff et al. 1979, Sabljic 1987) 3.16–3.33 (soil, calculated-KOW, model of Kenaga & Goring 1980, Sabljic 1987) 2.36–2.52 (soil, calculated-KOW, model of Briggs 1981, Sabljic 1987) 2.98–3.30 (soil, calculated-KOW, model of Means et al. 1982, Sabljic 1987) 2.19–2.48 (soil, calculated-KOW, model of Chiou et al. 1983, Sabljic 1987) 4.22, 4.26 (soil, quoted, calculated-MCI ., Sabljic 1987) 4.11, 3.32 (quoted, calculated-MCI ., Gerstl & Helling 1987) 4.11, 4.31 (soil, quoted, calculated-MCI . and fragment contribution, Meylan et al. 1992) 4.00 (HPLC-k. correlation, Nielsen et al. 1997) 4.79 (soil-pore water partition coeff., Askov soil - a Danish agricultural soil, Sverdrup et al. 2002) Environmental Fate Rate Constants, k, or Half-Lives, t.: Bioconcentration, Uptake (k1) and Elimination (k2) Rate Constants: k1 = 109 h–1, k2 = 3.68 h–1 (daphnia pulex, 21°C, Southworth et al. 1978) Half-Lives in the Environment: Biota: elimination t. = 11.3 min (daphnia pulex, Southworth et al. 1978). © 2006 by Taylor & Francis Group, LLC 3382 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals TABLE 16.1.7.12.1 Reported vapor pressures of acridine at various temperatures and the coefficients for the vapor pressure equations log P = A – B/(T/K) (1) ln P = A – B/(T/K) (1a) log P = A – B/(C + t/°C) (2) ln P = A – B/(C + t/°C) (2a) log P = A – B/(C + T/K) (3) log P = A – B/(T/K) – C·log (T/K) (4) Stull 1947 McEachern et al. 1975 summary of literature data Langmuir free evaporation t/°C P/Pa t/°C P/Pa t/°C P/Pa 129.4 133.3 7.96 0.000653 eq. 1a P/mmHg 165.8 666.6 12.02 0.001027 A 27.076 184.0 1333 16.08 0.002413 B 11021.64 203.5 2666 19.95 0.00329 temp range: 281.2–323.2 K 224.2 5333 25.05 0.00652 enthalpy of fusion: 238.7 7999 25.05 0.00656 .Hfus/(kJ mol–1) = 18.58 256.0 13332 29.98 0.01145 enthalpy of sublimation: 284.0 26664 35.08 0.0213 .Hsub/(kJ mol–1) = 121.75 314.3 53329 40.02 0.0380 temp range: 281.2–323.3 K 345.0 101325 45.09 0.0640 enthalpy of vaporization: 50.0 0.1074 .HV/(kJ mol–1) = 72.59 mp/°C 110.5 FIGURE 16.1.7.12.1 Logarithm of vapor pressure versus reciprocal temperature for acridine. Acridine: vapor pressure vs. 1/T -4.0 -3.0 -2.0 -1.0 0.0 1.0 2.0 3.0 4.0 5.0 6.0 0.0014 0.0018 0.0022 0.0026 0.003 0.0034 0.0038 1/(T/K) P( gol S ) aP/ McEachern et al. 1975 Stull 1947 b.p. = 344.86°C m.p. = 106 °C © 2006 by Taylor & Francis Group, LLC Nitrogen and Sulfur Compounds 3383 16.1.8 SULFUR COMPOUNDS 16.1.8.1 Carbon disulfide Common Name: Carbon disulfide Synonym: carbon disulphide Chemical Name: carbon disulfide CAS Registry No: 75-15-0 Molecular Formula: CS2 Molecular Weight: 76.141 Melting Point (°C): –112.1 (Lide 2003) Boiling Point (°C): 46 (Lide 2003) Density (g/cm3): 1.2632 (20°C, Weast 19820–83) 1.26311, 1.2555 (20°C, 25°C, Riddick et al. 1986) Molar Volume (cm3/mol): 66.0 (calculated-Le Bas method at normal boiling point) Enthalpy of Vaporization, .HV (kJ/mol): 27.522, 26.736 (25°C, bp, Riddick et al. 1986) Enthalpy of Sublimation, .Hsubl (kJ/mol): Enthalpy of Fusion, .Hfus (kJ/mol): 4.389 (Riddick et al. 1986) Entropy of Fusion, .Sfus (J/mol K): Fugacity Ratio at 25°C (assuming .Sfus = 56 J/mol K), F: 1.0 Water Solubility (g/m3 or mg/L at 25°C): 2100 (20°C, selected, Riddick et al. 1986) Vapor Pressure (Pa at 25°C or as indicated and reported temperature dependence equations. Additional data at other temperatures designated * are compiled at the end of this section): 53329* (28°C, summary of literature data, temp range –73.8 to 46.5°C, Stull 1947) 47359* (24.582°C, comparative ebulliometry, measured range 3.6–80°C, Waddington et al. 1962) log (P/mmHg) = 6.94194 – 1168.623/(241.534 + t/°C); temp range 3.6–80°C (Antoine eq., comparative ebulliometry, Waddington et al. 1962) 49704* (25.931°C, temp range –17.76 to 45.142°C, Boublik & Aim 1972; quoted, Boublik et al 1984) log (P/kPa) = 6.86752 – 1169.022/(241.582 + t/°C), temp range 3.6–80°C (Antoine eq. derived from exptl. data of Waddington et al. 1949, Boublik et al. 1984) log (P/kPa) = 6.03385 – 1151.908/(239.748 + t/°C), temp range –17.76 to 45.14°C (Antoine eq. derived from exptl. data, Boublik et al. 1984) 48210 (selected, Riddick et al. 1986) log (P/kPa) = 6.06694 – 1168.623/(t/°C + 241.534) temp range not specified (Antoine eq., Riddick et al. 1986) log (PL/kPa) = 6.03694 – 1153.5/(–33.22 + T/K); temp range 256–319 K (Antoine eq.-I, Stephenson & Malanowski 1987) log (PL/kPa) = 6.07588 – 1174.112/(–30.896 + T/K); temp range 260–353 K (Antoine eq.-II, Stephenson & Malanowski 1987) log (PL/kPa) = 6 19814– 1231.307/(–26.024 + T/K); temp range 338–408 K (Antoine eq.-III, Stephenson & Malanowski 1987) log (PL/kPa) = 6 80466– 1278.903/(43.404 + T/K); temp range 388–497 K (Antoine eq.-IV, Stephenson & Malanowski 1987) log (PL/kPa) = 7.58592 – 2639.181/(165.312 + T/K); temp range 490–533 K (Antoine eq.-V, Stephenson & Malanowski 1987) S S C © 2006 by Taylor & Francis Group, LLC 3384 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals 39597 (20°C, Howard 1990) log (P/mmHg) = 25.1475 – 2.0349 . 103/(T/K) –6.7794·log (T/K) + 3.4828 . 10–3·(T/K) – 1.0105 . 10–14·(T/K)2; temp range 162–552 K (vapor pressure eq., Yaws 1994) Henry’s Law Constant (Pa m3/mol at 25°C or as indicated): 142 (calculated-P/C, Howard 1990) 1946 (calculated-vapor-liquid equilibrium VLE data, Yaws et al. 1991) 1577 (20°C, selected from literature experimentally measured data, Staudinger & Roberts 2001) log KAW = 3.485 – 1077/(T/K) (van’t Hoff eq. derived from literature data, Staudinger & Roberts 2001) Octanol/Water Partition Coefficient, log KOW: 1.70–4.60 (Hansch & Leo 1985) 2.14 (recommended, Sangster 1993) 1.94 (recommended, Hansch et al. 1995) Octanol/Air Partition Coefficient, log KOA: Bioconcentration Factor, log BCF or log KB: 0.90 (calculated-solubility, Howard 1990) Sorption Partition Coefficient, log KOC: 1.80 (calculated-solubility, Howard 1990) Environmental Fate Rate Constants, k, and Half-Lives, t.: Volatilization: t. = 2.6 h in a model river (Howard 1990) Photolysis: Oxidation: Hydrolysis: t. = 1.1 yr at pH 9 in alkaline solution (Howard 1990) Biodegradation: Biotransformation: Bioconcentration and Uptake and Elimination Rate Constants (k1 and k2): Half-Lives in the Environment: Air: t.: = 9 d degraded by reacting with atomic oxygen and photochemically produced OH radicals (Howard 1990) TABLE 16.1.8.1.1 Reported vapor pressures of carbon disulfide at various temperatures and the coefficients for the vapor pressure equations log P = A – B/(T/K) (1) ln P = A – B/(T/K) (1a) log P = A – B/(C + t/°C) (2) ln P = A – B/(C + t/°C) (2a) log P = A – B/(C + T/K) (3) log P = A – B/(T/K) – C·log (T/K) (4) Stull 1947 Waddington et al. 1962 Boublik & Aim 1972 summary of literature data comparative ebulliometry in Boublik et a. 1984 t/°C P/Pa t/°C P/Pa t/°C P/Pa –73.8 133.3 3.588 19920 –17.76 6967 –54.3 666.6 8.772 25007 ~12.358 9306 –44.7 1333 13.999 31168 ~7.204 12046 –34.3 2666 19.269 38547 ~3.286 14549 –22.5 5333 24.582 47359 1.223 17921 –15.3 7999 29.927 57803 5.076 21314 © 2006 by Taylor & Francis Group, LLC Nitrogen and Sulfur Compounds 3385 TABLE 16.1.8.1.1 (Continued) Stull 1947 Waddington et al. 1962 Boublik & Aim 1972 summary of literature data comparative ebulliometry in Boublik et a. 1984 t/°C P/Pa t/°C P/Pa t/°C P/Pa –5.1 13332 35.318 70109 9.448 25780 10.4 26664 40.751 84525 12.981 29923 28.0 53329 46.225 101325 17.168 35493 46.5 101325 51.744 120798 21.087 41470 57.295 143268 25.931 49704 mp/°C –110.8 62.885 169052 31.522 61295 68.531 198530 38.041 77125 74.218 232087 45.142 97853 79.927 270110 bp/°C 46.217 bp/°C 46.22 Antoine eq. eq. 2 P/kPa eq. 2 P/mmHg A 6.03385 A 6.94194 B 1151.908 B 1168.623 C 239.748 C 241.534 data also fitted to Cox eq. see ref. FIGURE 16.1.8.1.1 Logarithm of vapor pressure versus reciprocal temperature for carbon disulfide. Carbon disulfide: vapor pressure vs. 1/T 0.0 1.0 2.0 3.0 4.0 5.0 6.0 7.0 8.0 0.0028 0.0032 0.0036 0.004 0.0044 0.0048 0.0052 1/(T/K) P ( g o l S ) a P / Waddington et al. 1962 Boublik & Aim 1972 Stull 1947 b.p. = 46 °C © 2006 by Taylor & Francis Group, LLC 3386 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals 16.1.8.2 Dimethyl sulfide Common Name: Dimethyl sulfide Synonym: DMS, methyl sulfide, thiobismethane, 2-thiapropane Chemical Name: dimethyl sulfide CAS Registry No: 75-18-3 Molecular Formula: C2H6S, (CH3)2S Molecular Weight: 62.134 Melting Point (°C): –98.24 (Lide 2003) Boiling Point (C): 37.33 (Riddick et al. 1986; Lide 2003) Density (g/cm3 at 25°C): 0.84825, 0.84230 (20°C, 25°C, Dreisbach 1961) 0.8423 (Riddick et al. 1986) Molar Volume (cm3/mol): 73.2 (Kamlet et al. 1986) 73.8 (20°C, calculated-density) 77.4 (calculated-Le Bas method at normal boiling point) Dissociation Constant pKBH + : –6.99 (Riddick et al. 1986) Enthalpy of Vaporization, .HV (kJ/mol): 27.49, 26.82 (25°C, bp, Dreisbach 1961) 27.65, 27.0 (25°C, bp, Riddick et al. 1986) Enthalpy of Fusion, .Hfus (kJ/mol): 7.99 (Riddick et al. 1986) Entropy of Fusion, .Sfus (J/mol K): Fugacity Ratio at 25°C (assuming .Sfus = 56 J/mol K), F: 1.0 Water Solubility (g/m3 or mg/L at 25°C): 15606 (Hine & Mookerjee 1975) 6300 (Verschueren 1983) 22000 (estimated-activity coefficient by headspace-GC, Przyjazny et al. 1983) 20000 (Riddick et al. 1986) 19600 (selected, Yaws et al. 1990) Vapor Pressure (Pa at 25°C and reported temperature dependence equations. Additional data at other temperatures designated * are compiled at the end of this section): 53174* (20.087°C, static method, measured range –22.547 to 20.087°C, Osborn et al. 1942) log (P/mmHg) = 16.51798 – 1876.370/(T/K) – 3.04727 ± log (T/K); temp range –22.547 to 20.087°C (static method, Osborn et al. 1942) 53329* (18.7°C, summary of literature data, temp range –75.6 to 36°C, Stull 1947) 64650 (calculated from determined data, Dreisbach 1961) log (P/mmHg) = 6.93138 – 1081.587/(229.746 + t/°C), temp range –50 to 130°C (Antoine eq. for liquid state, Dreisbach 1961) 64501* (interpolated-Antoine eq., temp range –47.4 to 58.319°C, Zwolinski & Wilhoit 1971) log (P/mmHg) = 6.94879 – 1090.755/(230.799 + t/°C); temp range –47.4 to 58.319°C (liquid, Antoine eq., Zwolinski & Wilhoit 1971) 70300 (Hine & Mookerjee 1975) log (P/mmHg) =[–0.2185 . 6742.3/(T/K)] + 7.589204; temp range –75 to 224.5°C (Antoine eq., Weast 1972–73) 56000 (20°C, Verschueren 1983) 64443 (calculated-Antoine eq. of Boublik et al. 1973, Przyjazny et al. 1983) 64460 (extrapolated-Antoine eq., Boublik et al. 1984) S © 2006 by Taylor & Francis Group, LLC Nitrogen and Sulfur Compounds 3387 log (P/kPa) = 6.27843 – 1196.875/(242.81 + t/°C), temp range –22.55 to 20.09°C (Antoine eq. from reported exptl. data, Boublik et al. 1984) 64470 (extrapolated-Antoine eq., Dean 1985, 1992) log (P/mmHg) = 7.1509 – 1195.58/(242.68 + t/°C); temp range –22 to 20°C (Antoine eq., Dean 1985, 1992) 64650 (quoted, Riddick et al. 1986) log (P/kPa) = 6.07369 – 1090.755/(230.799 + t/°C); temp range not specified (Antoine eq., Riddick et al. 1986) 64520 (interpolated, Antoine eq., Stephenson & Malanowski 1987) log (PL/kPa) = 6.07043 – 1088.851/(–42.594 + T/K); temp range 268–319 K (Antoine eq.-I, Stephenson & Malanowski 1987) log (PL/kPa) = 6.13042 – 1124.998/(–37.961 + T/K); temp range 307–379 K (Antoine eq.-II, Stephenson & Malanowski 1987) log (PL/kPa) = 6.42655 – 1344.329/(–7.456 + T/K); temp range 372–453 K (Antoine eq.-III, Stephenson & Malanowski 1987) log (PL/kPa) = 7.36327 – 2293.043/(130.243 + T/K); temp range 447–503 K (Antoine eq.-IV, Stephenson & Malanowski 1987) log (P/mmHg) = 37.2604 – 2.4251 . 103/(T/K) –11.384·log (T/K) + 5.8122 . 10–3·(T/K) + 8.5893 . 10–14·(T/K)2; temp range 175–503 K (vapor pressure eq., Yaws 1994) Henry’s Law Constant (Pa·m3/mol at 25°C or as indicated and reported temperature dependence. Additional data at other temperatures designated * are compiled at the end of this section): 278.1 (1/KAW, exptl., Hine & Mookerjee 1975) 298, 366.6 (calculated-group contribution, calculated-bond contribution, Hine & Mookerjee 1975) 165 (20°C, headspace-GC, Vitenberg et al. 1975) 180.4, 184.7, 173.5 (headspace-GC, concn. of 10, 1.0, 0.1 ppm by weight, Przyjazny et al. 1983) 180.4, 184.7, 173.5 (headspace-GC, concn. of 10, 1.0 and 0.1 ppm by weight, measured range 25–70°C, data presented in graph, Przyjazny et al. 1983) log (1/KAW) = 1637.3/(T/K) – 4.354; temp range 25–70°C (headspace-GC, concn of 10 ppm by weight, Przyjazny et al. 1983) log (1/KAW) = 1635.6/(T/K) – 4.358; temp range 25–70°C (headspace-GC, concn of 1.0 ppm by weight, Przyjazny et al. 1983) log (1/KAW) = 1598.2/(T/K) – 4.205; temp range 25–70°C (headspace-GC, concn of 0.1 ppm by weight, Przyjazny et al. 1983) 163.4 (quoted, Gaffney et al. 1987) 184, 1271 (quoted, calculated-molecular structure, Russell et al. 1992) 138 (20°C, selected from literature experimentally measured data, Staudinger & Roberts 1996) 233.0* (equilibrium headspace-GC, in seawater, measured range 18–44°C, Wong & Wang 1997) 61.97 (equilibrium headspace-GC, Marin et al. 1999) 155 (20°C, selected from literature experimentally measured data, Staudinger & Roberts 2001) log KAW = 3.556 – 1394/(T/K), (van’t Hoff eq. derived from literature data, Staudinger & Roberts 2001) Octanol/Water Partition Coefficient, log KOW: Octanol/Air Partition Coefficient, log KOA: Bioconcentration Factor, log BCF: Sorption Partition Coefficient, log KOC: Environmental Fate Rate Constants, k, or Half-Lives, t.: Volatilization: Photolysis: Oxidation: rate constant k, for gas-phase second order rate constants, kOH for reaction with OH radical, kNO3 with NO3 radical and kO3 with O3 or as indicated, *data at other temperatures and/or the Arrhenius expression see reference: © 2006 by Taylor & Francis Group, LLC 3388 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals kOH* = (9.80 ± 1.2) . 10–12 cm3 molecule–1 s–1 at 299.9 K, measured range 299.9–426.5 K (flash photolysisresonance fluorescence, Atkinson et al. 1978) kOH* = (8.28 ± 0.87) . 10–12 cm3 molecule–1 s–1 at 297 K, measured range 273–400 K by flash photolysisresonance fluorescence, Kurylo 1978) kO(3P)* = 57 . 10–12 cm3 molecule–1 s–1 for gas-phase reaction with O(3P) atom at 296 K, measured range 252–493 K (Slagle et al. 1978) kOH* = (4.26 ± 0.56) . 10–11 cm3 molecule–1 s–1 at 298 K, measured range 248–363 K (flash photolysisresonance fluorescence, Wine et al. 1981) kOH = (1.0 ± 0.1) . 10–11 cm3 molecule–1 s–1 with an estimated lifetime . ~ 30 h in the daytime, kNO3 = (5.4 ± 0.7) . 10–13 cm3 molecule–1 s–1 with an estimated . ~ 3 h in the nighttime hours at 296 ± 2 K (Atkinson et al 1984) kO3 < 8 . 10–19 cm3 molecule–1 s–1 with a loss rate of < 0.05 d–1, kOH = 9.80 . 10–12 cm3 ± molecule–1 s–1 with a loss rate of 0.8 d–1, and kNO3 = 9.7 . 10–13 cm3 molecule–1 s–1 with a loss rate of 20 d–1 at room temp. (review, Atkinson & Carter 1984) kO3 < 8 . 10–20 cm3 molecule–1 s–1 with a loss rate of < 0.004 d–1, kOH = 6.3 . 10–12 cm3 molecule–1 s–1 with a loss rate of 0.27 d–1, and kNO3 = 9.7 . 10–13 cm3 molecule–1 s–1 with a loss rate of 20 d–1 at room temp. (review, Atkinson 1985) kOH* = (4.09, 4.44) . 10–12 cm3 molecule–1 s–1 at 298 K, measured range 267–397 K (flash photolysisresonance fluorescence, Hynes et al. 1986) kOH* = (3.60 ± 0.2) . 10–12 cm3 molecule–1 s–1 at 297 K, measured range 297–440 K by flash photolysisresonance fluorescence; kOH = 9.36 . 10–12 cm3 molecule–1 s–1 relative rate to n-hexane, kOH = 5.36 . 10–12 cm3 molecule–1 s–1 relative rate to cyclohexane at 296 K (Wallington et al. 1986a) kNO3* = (8.1 ± 1.3) . 10–13 cm3 molecule–1 s–1 at 298 K, measured range 280–350 K (flash photolysis-visible absorption, Wallington et al. 1986b) kOH* = (5.50 ± 1.0) . 10–12 cm3 molecule–1 s–1 at 298 K, measured range 260–393 K (discharge flowresonance fluorescence, Hsu et al. 1987) kOH = (8.0 ± 0.5) . 10–12 cm3 molecule–1 s–1 at 298 K (Relative rate method, Barnes et al. 1989) kOH = 3.60 . 10–12 cm3 molecule–1 s–1; k(soln) = 3.2 . 10–11 cm3 molecule–1 s–1 for reaction with OH radical in aqueous solution (Wallington et al. 1988) kNO3* = (10.6 ± 1.3) . 10–13 cm3 molecule–1 s–1 at room temp., measured range 256–376 K (flow tube-laser induced fluorescence, Dlugokencky & Howard 1988) kOH* = 4.56 . 10–12 cm3 molecule–1 s–1 at 298 K (recommended, Atkinson 1989) kOH = 4.57 . 10–12 cm3 molecule–1 s–1, kNO3 = 9.77 . 10–13 cm3 molecule–1 s–1 (Sabljic & Gusten 1990; Muller & Klein 1991) kNO3* = 1.07 . 10–12 cm3 molecule–1 s–1 at 298 K (recommended, Atkinson 1991) Hydrolysis: Biodegradation: Biotransformation: Bioconcentration, Uptake (k1) and Elimination (k2) Rate Constants: Half-Lives in the Environment: Air: atmospheric lifetime . ~ 30 h due to reaction with OH radical in the daytime and . ~3 h due to reaction at night with NO3 radical (Atkinson et al. 1984); calculated lifetimes, . > 20 d due to reaction with O3 in 24-h, . = 28 h with OH radical during daytime and . = 120 min with NO3 radical during nighttime in “clean” atmosphere; . > 3 d due to reaction with O3 in 24-h, . = 420 min with OH radical in daytime and . = 13 min with NO3 in nighttime in “moderately polluted” atmosphere (Winer et al. 1984) estimated tropospheric chemical lifetimes, . = 2 d, 2 d and > 15 d for reactions with OH, NO3 and O3, respectively, under typical remote tropospheric conditions (Falbe-Hansen et al. 2000) © 2006 by Taylor & Francis Group, LLC Nitrogen and Sulfur Compounds 3389 TABLE 16.1.8.2.1 Reported vapor pressures and Henry’s law constants of dimethyl sulfide at various temperatures Vapor pressure Henry’s law constant Osborn et al. 1942 Stull 1947 Zwolinski & Wilhoit 1971 Wong & Wang 1997 static method-manometer summary of literature data selected values equilibrium headspace-GC t/°C P/Pa t/°C P/Pa t/°C P/Pa t/°C H/(Pa m3/mol) in seawater –22.547 6994 –75.6 –133.3 47.4 1333 18 164.6 –10.028 13699 –58.0 666.6 –37.7 2666 25 233.0 0.096 22437 –49.2 1333 –31.5 4000 35 381.7 4.943 28042 –39.4 2666 –26.9 5333 44 556.4 15.138 43512 –28.4 5333 –23.03 6666 20.087 53174 –21.4 7999 –19.85 7999 log KAW = A – B/(T/K) –12.0 13332 –14.62 10666 KAW mp/K 174.855 2.60 26664 –10.39 13332 A 4.806 bp/K 310.49 18.7 53329 –2.258 19998 B 1735 36.0 101325 3.885 26664 log P = A – B/(T/K) – C·log (T/K) 8.883 33331 P/mmHg mp/°C –83.2 13.127 39997 A 16.51798 20.138 53329 B 1876.370 25.860 66661 C 3.04727 30.733 79993 35.000 93326 .Hfus/(kJ mol–1) = 7.985 35.794 95992 .HV/(kJ mol–1) = 27.98 36.572 98659 at 291.06 K 37.333 101325 25 64501 Antoine eq. log P = A – B/(C + t/°C) P/mmHg A 6.94879 B 1090.755 C 230.799 bp/°C 37.333 .HV/(kJ mol–1) = at 25°C 27.65 at bp 26.92 © 2006 by Taylor & Francis Group, LLC 3390 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals FIGURE 16.1.8.2.1 Logarithm of vapor pressure versus reciprocal temperature for dimethyl sulfide. FIGURE 16.1.8.2.2 Logarithm of Henry’s law constant versus reciprocal temperature for dimethyl sulfide. Dimethyl sulfide: vapor pressure vs. 1/T 0.0 1.0 2.0 3.0 4.0 5.0 6.0 7.0 8.0 0.0028 0.0032 0.0036 0.004 0.0044 0.0048 0.0052 1/(T/K) P ( gol S ) aP/ Osborn et al. 1942 Stull 1947 Zwolinski & Wilhoit 1971 b.p. = 37.33 °C Dimethyl sulfide: Henry's law constant vs. 1/T 4.0 5.0 6.0 7.0 8.0 0.003 0.0031 0.0032 0.0033 0.0034 0.0035 0.0036 0.0037 0.0038 1/(T/K) m. aP( / H nl 3 ) l om/ Wong & Wang 1997 (in seawater) Hine & Mookerjee 1975 Vitenberg et al. 1975 Marin et al. 1999 © 2006 by Taylor & Francis Group, LLC Nitrogen and Sulfur Compounds 3391 16.1.8.3 Dimethyl disulfide Common Name: Dimethyl disulfide Synonym: 2,3-dithiabutane Chemical Name: dimethyl didisulfide CAS Registry No: 624-92-0 Molecular Formula: C2H6S2, CH3SSCH3 Molecular Weight: 94.199 Melting Point (°C): –84.67 (Lide 2003) Boiling Point (°C): 109.74 (Lide 2003) Density (g/cm3): 1.6025 (20°C, Weast 1982–83) Dissociation Constant, pKa: Molar Volume (cm3/mol): 103.0 (calculated-Le Bas method at normal boiling point) Enthalpy of Vaporization, .HV (kJ/mol): 38.37, 33.68 (25, bp, Zwolinski & Wilhoit 1971) Enthalpy of Sublimation, .Hsubl (kJ/mol): Enthalpy of Fusion, .Hfus (kJ/mol): Entropy of Fusion, .Sfus (J/mol K): Fugacity Ratio at 25°C (assuming .Sfus = 56 J/mol K), F: 1.0 Water Solubility (g/m3 or mg/L at 25°C): 3400 (estimated-activity coefficient by headspace-GC, Przyjazny et al. 1983) Vapor Pressure (Pa at 25°C or as indicated and reported temperature dependence equations. Additional data at other temperatures designated * are compiled at the end of this section): 3825* (static method, measured range 0–60°C, Scott et al. 1950) 3813* (interpolated-Antoine eq., temp range 5.356–109.745°C, Zwolinski & Wilhoit 1971) log (P/mmHg) = 6.97792 – 1396.342/(218.863 + t/°C); temp range 5.356 –109.745°C (Antoine eq., Zwolinski & Wilhoit 1971) 3850 (calculated-Antoine eq. of Boublik et al. 1973, Przyjazny et al. 1983) log (P/kPa) = 6.18000 – 1389.151/(223.184 + t/°C), temp range 0–60°C (Antoine eq. derived from Scott et al. 1950 data, Boublik et al. 1984) log (P/kPa) = 6.08703 – 1336.665/(217.767 + t/°C), temp range 61.4–128,6°C (Antoine eq. derived from Scott et al. 1950 data, Boublik et al. 1984) log (PL/kPa) = 6.10018 – 1349.006/(–54.389 + T/K), temp range 297–402 K, (Antoine eq., Stephenson & Malanowski 1987) log (P/mmHg) = 36.232 – 3.1241 . 103/(T/K) – 9.9328·log (T/K) + 2.2831 . 10–11·(T/K) + 3.1730 . 10–6·(T/K)2; temp range 125–499 K (vapor pressure eq., Yaws 1994) Henry’s Law Constant (Pa m3/mol at 25°C or as indicated): 121 (20°C, headspace-GC, Vitenberg et al. 1975) 112, 101 (headspace-GC, concn. of 10 and 1.0 ppm by weight, measured range 25–70°C, data presented in graph, Przyjazny et al. 1983) log (1/KAW) = 1657.1/(T/K) – 4.211; temp range 25–70°C (headspace-GC, concn of 10 ppm by weight, Przyjazny et al. 1983) log (1/KAW) = 1854.4/(T/K) – 4.828; temp range 25–70°C (headspace-GC, concn of 1.0 ppm by weight, Przyjazny et al. 1983) 77.5 (20°C, selected from literature experimentally measured data, Staudinger & Roberts 1996, 2001) S S © 2006 by Taylor & Francis Group, LLC 3392 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals log KAW = 4.828 – 1384/(T/K), (van’t Hoff eq. derived from literature data, Staudinger & Roberts 2001) Octanol/Water Partition Coefficient, log KOW: 1.77 (shake flask, Log P Database, Hansch & Leo 1987) 1.77 (recommended, Sangster 1993) 1.77 (recommended, Hansch et al. 1995) Octanol/Air Partition Coefficient, log KOA: Bioconcentration Factor, log BCF or log KB: Sorption Partition Coefficient, log KOC: Environmental Fate Rate Constants, k, and Half-Lives, t., or Lifetimes, .: Volatilization: Photolysis: Oxidation: rate constant k, for gas-phase second order rate constants, kOH for reaction with OH radical, kNO3 with NO3 radical and kO3 with O3 or as indicated, *data at other temperatures see reference: kOH = 2.40 . 10–10 cm3 molecule–1 s–1, at 297 K (relative rate method, Cox & Sheppard 1980) kOH* = (1.84 – 19.8) . 10–10 cm3 molecule–1 s–1, at 298 K, measured range 255–377 K (flask photolysisresonance fluorescence, Wine et al. 1984) kOH* = 2.05 . 10–10 cm3 molecule–1 s–1, at 298 K (tentative recommended, Atkinson 1985) kNO3* = 4.9 . 10–13 cm3 molecule–1 s–1 at 298 K, measured range 280–350 K (flash photolysis-optical absorption, Wallington et al. 1986) kNO3* = (7.3 ± 1.5) . 10–13 cm3 molecule–1 s–1 at room temp., measured range 334–382 K (flow tube-laser induced fluorescence, Dlugokencky & Howard 1988) kNO3 = 7.0 . 10–13 cm3 molecule–1 s–1, independent of temperature over the range ~300–380 K (recommended, Atkinson 1991) Hydrolysis: Biodegradation: Biotransformation: Bioconcentration and Uptake and Elimination Rate Constants (k1 and k2): Half-Lives in the Environment: © 2006 by Taylor & Francis Group, LLC Nitrogen and Sulfur Compounds 3393 TABLE 16.1.8.3.1 Reported vapor pressures of dimethyl disulfide at various temperatures and the coefficients for the vapor pressure equations log P = A – B/(T/K) (1) ln P = A – B/(T/K) (1a) log P = A – B/(C + t/°C) (2) ln P = A – B/(C + t/°C) (2a) log P = A – B/(C + T/K) (3) log P = A – B/(T/K) – C·log (T/K) (4) Scott et al. 1950 Zwolinski & Wilhoit 1971 static method-manometer ebulliometric method selected values t/°C P/Pa t/°C P/Pa t/°C P/Pa t/°C P/Pa 0 904 61.411 19920 5.356 1333 106.905 93326 15 2230 67.301 25007 18.299 2666 107.872 95992 20 2936 73.234 31160 25.891 4000 108.819 98659 25 3825 79.201 38547 31.579 5333 109.745 101325 30 4930 85.218 47359 36.177 6666 25.0 3813 35 6301 91.283 57803 40.060 7999 Antoine eq. 40 7975 97.393 70109 46.435 10666 eq. 2 P/mmHg 45 10007 103.54 84525 51.600 13332 A 6.97792 50 12448 109.738 101325 61.518 19998 B 1396.342 55 15359 115.984 120798 69.008 26664 C 218.863 60 18813 122.273 143268 75.099 33331 bp/°C 109.745 128.611 169052 80.271 39997 .HV/(kJ mol–1) = 88.812 53329 at 25°C 38.37 95.780 66661 at bp 33.68 101.712 79993 FIGURE 16.1.8.3.1 Logarithm of vapor pressure versus reciprocal temperature for dimethyl disulfide. Dimethyl disulfide: vapor pressure vs. 1/T 0.0 1.0 2.0 3.0 4.0 5.0 6.0 7.0 8.0 0.0024 0.0026 0.0028 0.003 0.0032 0.0034 0.0036 0.0038 0.004 1/(T/K) log (PS/Pa) Scott et al. 1950 Zwolinski & Wilhoit 1971 b.p. = 109.74 °C © 2006 by Taylor & Francis Group, LLC 3394 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals 16.1.8.4 Dimethyl sulfoxide (DMSO) Common Name: Dimethyl sulfoxide Synonym: DMSO, sulfinylbismethane, methyl sulfoxide, methylsulfinylmethane, SQ 9453, DMS-70, DMS-90, Deltan, Demasorb, Demavet, Demeso, Dermasorb, Dolicur, Domoso, Dromisol, Gamasol 90, Hyadur, Rimso-50, Sclerosol, Somipront, Somtexan, Topsym Chemical Name: dimethyl sulfoxide CAS Registry No: 67-68-5 Molecular Formula: C2H6OS, (CH3)2SO Molecular Weight: 78.133 Melting Point (°C): 17.89 (Lide 2003) Boiling Point (°C): 189.0 (Stephenson & Malanowski 1987; Lide 2003) Density (g/cm3 at 25°C): 1.1014 (Weast 1982–83) Molar Volume (cm3/mol): 85.7 (calculated-Le Bas method at normal boiling point) Dissociation Constant pKa: 1.4 (Riddick et al. 1986) Enthalpy of Vaporization, .HV (kJ/mol): 52.88, 43.14 (25°C, bp, Riddick et al. 1986) Enthalpy of Fusion, .Hfus (kJ/mol): 14.368 (Riddick et al. 1986) Entropy of Fusion, .Sfus (J/mol K): Fugacity Ratio at 25°C (assuming .Sfus = 56 J/mol K), F: 1.0 Water Solubility (g/m3 or mg/L at 25°C): 253000 (Riddick et a. 1986) Vapor Pressure (Pa at 25°C or as indicated and reported temperature dependence equations. Additional data at other temperatures designated * are compiled at the end of this section): 80.0* (gas saturation, measured range 20–50°C, Douglas 1948) log (P/mmHg) = 26.49588 – 3539.32/(T/K) – 6.000 ± ln (T/K); temp range 20–50°C (gas saturation, Douglas 1948) 460* (52.35°C, Hg manometer, measured range 325.5–442.1 K, Jakli & van Hook 1972) ln (P/mmHg) = 17.4922 – 4517.79/(T/K – 47.2583); temp range 291.7–463 K (Hg manometer, Antoine eq. with literature data, Jakli & van Hook 1972) 56.0 (20°C, Verschueren 1983) 80.9 (extrapolated-Antoine eq., Boublik et al. 1984) log (P/kPa) = 6.64816 – 1922.32/(223.353 + t/°C); temp range 52.4–168.95°C (Antoine eq. from reported exptl. data of Jakli & von Hook 1972, Boublik et al. 1984) 80.0 (selected, Riddick et al. 1986) log (P/kPa) = 6.72161 – 1962.06/(225.892 + t/°C); temp range not specified (Antoine eq., Riddick et al. 1986) 79.5 (extrapolated-Antoine eq., Stephenson & Malanowski 1987) log (PL/kPa) = 6.72167 – 1962.05/(–47.258 + T/K); temp range 305–464 K (Antoine eq., Stephenson & Malanowski 1987) log (P/mmHg) = 45.4653 – 4.0439 . 103/(T/K) – 13.21·log (T/K) + 1.0981 . 10–7·(T/K) + 6.4155 . 10–6·(T/K)2; temp range 292–465 K (vapor pressure eq., Yaws et al. 1994) Henry’s Law Constant (Pa·m3/mol): O S © 2006 by Taylor & Francis Group, LLC Nitrogen and Sulfur Compounds 3395 Octanol/Water Partition Coefficient, log KOW: –1.35 (shake flask, Hansch & Leo 1979, 1987) –0.85 (calculated-UNIFAC activity coefficients, Banerjee & Howard 1988) –1.35 (recommended, Sangster 1989) –1.35 (recommended, Hansch et al. 1995) Octanol/Air Partition Coefficient, log KOA: 4.96 (head-space GC, Abraham et al. 2001) Bioconcentration Factor, log BCF: Sorption Partition Coefficient, log KOC: Environmental Fate Rate Constants, k, or Half-Lives, t.: Volatilization: Photolysis: Oxidation: rate constant k, for gas-phase second order rate constants, kOH for reaction with OH radical, kNO3 with NO3 radical and kO3 with O3 or as indicated, *data at other temperatures see reference: kOH = (6.2 ± 2.2) . 10–11 cm3 molecule–1 s–1; kNO3 = (1.7 ± 0.3) . 10–13 cm3 molecule–1 s–1; kO3 < 5.0 . 10–19 cm3 ± molecule–1 s–1 at room temp (Barnes et al. 1989) kOH = (62 ± 25) . 10–12 cm3 molecule–1 s–1 at 300 K (Atkinson 1989) kOH = (1.0 ± 0.3) . 10–12 cm3 molecule–1 s–1 at room temp (Hynes & Wine 1996) kOH = (8.7 ± 1.6) . 10–11 cm3 molecule–1 s–1 at room temp. (Urbanski et al. 1998) kOH = (5.9 ± 1.5) . 10–11 cm3 ± molecule–1 s–1 with tropospheric lifetime . = 5 h, kNO3 = (5.0 ± 3.8) . 10–13 cm3 molecule–1 s–1 with tropospheric lifetime . = 3 d; kO3 < 1.0 . 10–19 cm3 ± molecule–1 s–1 with tropospheric lifetime . > 150 d and kCl = (7.4 ± 1.0) . 10–11 cm3 molecule–1 s–1 for reaction wit Cl atoms with tropospheric lifetime . = 62 d at room temp and 740 torr (Relative rate method, Falbe-Hansen et al. 2000) Hydrolysis: k = 6.60 . 109 M–1 s–1 (Buxton et al. 1986) Biodegradation: Biotransformation: Bioconcentration, Uptake (k1) and Elimination (k2) Rate Constants: Half-Lives in the Environment: Air: estimated tropospheric chemical lifetimes, . = 5 h, 3 d and > 150 d for reactions with OH, NO3 and O3, respectively, under typical remote tropospheric conditions (Falbe-Hansen et al. 2000) © 2006 by Taylor & Francis Group, LLC 3396 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals TABLE 16.1.8.4.1 Reported vapor pressures of dimethyl sulfoxide at various temperatures and the coefficients for the vapor pressure equations log P = A – B/(T/K) (1) ln P = A – B/(T/K) (1a) log P = A – B/(C + t/°C) (2) ln P = A – B/(C + t/°C) (2a) log P = A – B/(C + T/K) (3) log P = A – B/(C + T/K) (3a) log P = A – B/(T/K) – C·log (T/K) (4) ln P = A – B/(T/K) – C·ln(T/K) (4a) Douglas 1948 Jakli & van Hook 1972 gas saturation mercury manometer t/°C P/Pa t/°C P/Pa t/°C P/Pa 20 55.6 52.35 460 140.15 22905 25 80.0 56.25 573 148.05 29471 30 113.7 61.45 767 162.15 47036 35 159.3 66.15 993 168.95 56342 40 220.8 74.85 1560 eq. 3 P/mmHg 45 302.6 79.95 2000 A 17.4922 50 409.3 85.65 2653 B 4517.79 90.26 3293 C 47.2583 eq. 4 P/mmHg 96.05 4226 A 29.49558 100.45 5106 B 3539.32 100.55 5133 C 6.0000 104.95 6246 111.95 8359 bp/°C 192 117.95 10452 .HV = 52.89 kJ/mol 127.45 14745 FIGURE 16.1.8.4.1 Logarithm of vapor pressure versus reciprocal temperature for dimethyl sulfoxide. Dimethyl sulfoxide: vapor pressure vs. 1/T 0.0 1.0 2.0 3.0 4.0 5.0 6.0 7.0 8.0 0.002 0.0022 0.0024 0.0026 0.0028 0.003 0.0032 0.0034 0.0036 1/(T/K) P( gol S ) aP / Douglas 1948 Jakli & van Hook 1972 b.p. = 189 °C m.p. = 17.89 °C © 2006 by Taylor & Francis Group, LLC Nitrogen and Sulfur Compounds 3397 16.1.8.5 Dimethyl sulfate Common Name: Dimethyl sulfate Synonym: sulfuric acid dimethyl ester, DMS Chemical Name: dimethyl sulfate CAS Registry No: 77-78-1 Molecular Formula: C2H6O4S, CH3O-SO2-OCH3 Molecular Weight: 126.132 Melting Point (°C): –27 (Lide 2003) Boiling Point (°C): 188 (decomposes, Lide 2003) Density (g/cm3 at 20°C): 1.3322 (Dean 1985) Molar Volume (cm3/mol): 95.0 (20°C, Stephenson & Malanowski 1987) 109.7 (calculated-Le Bas method at normal boiling point) Dissociation Constant pKa: Enthalpy of Fusion, .Hfus (kJ/mol): Entropy of Fusion, .Sfus (J/mol K): Fugacity Ratio at 25°C (assuming .Sfus = 56 J/mol K), F: 1.0 Water Solubility (g/m3 or mg/L at 25°C): 28000 (hydrolyzes, Verschueren 1983; Dean 1985) 28000 (18°C, Budavari 1989) Vapor Pressure (Pa at 25°C and reported temperature dependence equations): < 133 (20°C, Verschueren 1983) 128 (extrapolated, Antoine eq., Stephenson & Malanowski 1987) log (PL/kPa) = 7.28235 – 2437.54/(T/K), temp range 340–470 K, (Antoine eq., Stephenson & Malanowski 1987) log (P/mmHg) = 33.9406 – 3.853 . 103/(T/K) – 8.5921·log (T/K) – 1.1705 . 10–10·(T/K) + 8.226 . 10–7·(T/K)2; temp range 241–758 K (vapor pressure eq., Yaws 1994) Henry’s Law Constant (Pa·m3/mol): Octanol/Water Partition Coefficient, log KOW: Octanol/Air Partition Coefficient, log KOA: Bioconcentration Factor, log BCF: Sorption Partition Coefficient, log KOC: Environmental Fate Rate Constants, k, or Half-Lives, t.: Volatilization: Photolysis: Oxidation: atmospheric photooxidation t. = of 36.5–365 h, based on estimated rate constant for the vapor-phase reaction with OH radical in air (Atkinson 1987; quoted, Howard et al. 1991). Hydrolysis: first order hydrolysis rate constant k = 1.6 . 10–4 s–1 at pH 7 and 25°C with t. = 1.2 h (Mabey & Mill 1978; quoted, Howard et al. 1991). O S O O O © 2006 by Taylor & Francis Group, LLC 3398 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals Biodegradation: aqueous aerobic biodegradation t. ~ 168–672 h and aqueous anaerobic biodegradation t. ~ 672–2688 h (Howard et al. 1991). Biotransformation: Bioconcentration, Uptake (k1) and Elimination (k2) Rate Constants: Half-Lives in the Environment: Air: t. = 36.5–365 h, based on photooxidation half-life in air from estimated rate constant for the vapor phase reaction with hydroxyl radical in air (Atkinson 1987; quoted, Howard et al. 1991); atmospheric transformation lifetime (reaction with liquid water) estimated to be < 1 d (Kelly et al. 1994). Surface water: t. = 1.2–12 h, based on overall hydrolysis rate constant for pH 7 at 25°C (Mabey & Mill 1978; quoted, Howard et al. 1991) and for complete hydrolysis in neutral, slightly basic, and acidic aqueous solutions (Lee et al. 1980; quoted, Howard et al. 1991). Groundwater: t. = 1.2–12 h, based on overall hydrolysis rate constant for pH 7 at 25°C (Mabey & Mill 1978; quoted, Howard et al. 1991) and for complete hydrolysis in neutral, slightly basic, and acidic aqueous solutions (Lee et al. 1980; quoted, Howard et al. 1991). Sediment: Soil: t. = 1.2–12 h, based on overall hydrolysis rate constant for pH 7 at 25°C and for complete hydrolysis in neutral, slightly basic, and acidic aqueous solutions (Howard et al. 1991). Biota: © 2006 by Taylor & Francis Group, LLC Nitrogen and Sulfur Compounds 3399 16.1.8.6 Methanethiol Common Name: Methanethiol Synonym: methyl mercaptan Chemical Name: methanethiol CAS Registry No: 74-93-1 Molecular Formula: CH4S, CH3SH Molecular Weight: 48.108 Melting Point (°C): –123 (Weast 1982–83; Lide 2003) Boiling Point (°C): 5.9 (Lide 2003) Density (g/cm3): 0.8665 (20°C, Weast 1982–83) Dissociation Constant, pKa: Molar Volume (cm3/mol): 55.3 (20°C, Stephenson & Malanowski 1987) 55.2 (calculated-Le Bas method at normal boiling point) Enthalpy of Vaporization, .HV (kJ/mol): 23.8, 24.57 (25, bp, Zwolinski & Wilhoit 1971) Enthalpy of Sublimation, .Hsubl (kJ/mol): Enthalpy of Fusion, .Hfus (kJ/mol): Entropy of Fusion, .Sfus (J/mol K): Fugacity Ratio at 25°C (assuming .Sfus = 56 J/mol K), F: 1.0 Water Solubility (g/m3 or mg/L at 25°C): 39000 (estimated-activity coefficient by headspace-GC/FID, Przyjazny et al. 1983) Vapor Pressure (Pa at 25°C or as indicated and reported temperature dependence equations. Additional data at other temperatures designated * are compiled at the end of this section): 101410* (5.977°C, static method-Hg manometer, measured range –51.3 to 5.977°C, Russell et al. 1942) log (P/mmHg) = 18.27429 – 1769.05/(T/K) – 3.70248 ± log (T/K); temp range 221.88–279.137 K (static method, Russell, et al. 1942) 101325* (8.7°C, summary of literature data, temp range –90.7 to 7.8°C, Stull 1947) 202117* (extrapolated, summary of literature data, temp range –70.3 to 5.956°C, Zwolinski & Wilhoit 1971) log (P/mmHg) = 7.03163 – 1015.547/(238.706 + t/°C); temp range –70.3 to 24.694°C (Antoine eq., Zwolinski & Wilhoit 1971) 202346 (calculated-Antoine eq. of Boublik et al. 1973, Przyjazny et al. 1983) log (P/kPa) = 6.18991 – 1030.496/(248.330 + t/°C), temp range –51.28 to 5.977°C, (Antoine eq. derived from Russell et al. 1942 data, Boublik et al. 1984) log (PL/kPa) = 6.19283 – 1031.216/(–32.916 + T/K), temp range 221–283 K, (Antoine eq.-I, Stephenson & Malanowski 1987) log (PL/kPa) = 6.19219 – 1030.918/(–32.845 + T/K), temp range 222–279 K, (Antoine eq.-II, Stephenson & Malanowski 1987) log (PL/kPa) = 6.13699 – 1006.199/(–35.529 + T/K), temp range 267–359 K, (Antoine eq.-III, Stephenson & Malanowski 1987) log (PL/kPa) = 6.53487 – 1278.361/(5.318 + T/K), temp range 345–424 K, (Antoine eq.-IV, Stephenson & Malanowski 1987) H H H SH © 2006 by Taylor & Francis Group, LLC 3400 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals Henry’s Law Constant (Pa m3/mol at 25°C or as indicated): 247 (distilled water, headspace-GC/FID, measured range 25–70°C, data in graph, Przyjazny et al. 1983) Log (1/KAW) = 1347.1/(T/K) – 3.537; temp range 25–70°C (headspace-GC, Przyjazny et al. 1983) 187 (20°C, selected from literature experimentally measured data, Staudinger & Roberts 1996) 300 (20°C, selected from literature experimentally measured data, Staudinger & Roberts 2001) log KAW = 3.249 – 1219/(T/K), (van’t Hoff eq. derived from literature data, Staudinger & Roberts 2001) Octanol/Water Partition Coefficient, log KOW: Octanol/Air Partition Coefficient, log KOA: Bioconcentration Factor, log BCF or log KB: Sorption Partition Coefficient, log KOC: Environmental Fate Rate Constants, k, and Half-Lives, t.: Volatilization: Photolysis: Oxidation: rate constant k, for gas-phase second order rate constants, kOH for reaction with OH radical, kNO3 with NO3 radical and kO3 with O3 or as indicated, *data at other temperatures see reference: kOH* = 3.39 . 10–11 cm3 molecule–1 s–1 at 299.8 K, measured range 300–423 K (flash photolysis-resonance fluorescence, Atkinson et al. 1977) kOH* = 3.37 . 10–11 cm3 molecule–1 s–1 at 298 K, measured range 244–366 K (flash photolysis-resonance fluorescence, Wine et al. 1981) kOH = 9.7 . 10–11 cm3 molecule–1 s–1 at 297 K (relative rate method, Cox & Sheppard 1980) kOH = 2.01 . 10–11 cm3 molecule–1 s–1 at 293 K (discharge flow-EPR, Mac Leod et al. 1983) kOH = 2.56 . 10–11 cm3 molecule–1 s–1 at 296 K (discharge flow-RF, Lee & Tang 1983) kOH* = (3.04 – 32.5) . 10–11 cm3 molecule–1 s–1 at 298 K, measured range 254–430 K ((flash photolysisresonance fluorescence, Wine et al. 1984) kOH* = 3.31 . 10–11 cm3 molecule–1 s–1 at 298 K (recommended, Atkinson 1985) kNO3 = 9.2 . 10–13 cm3 ± molecule–1 s–1, independent of temperature over the range 250–370 K (IUPAC recommended, Atkinson et al. 1989) kNO3 = 9.3 . 10–13 cm3 ± molecule–1 s–1, independent of temperature over the range 254–367 K (Atkinson 1991) Hydrolysis: Biodegradation: Biotransformation: Bioconcentration and Uptake and Elimination Rate Constants (k1 and k2): Half-Lives in the Environment: © 2006 by Taylor & Francis Group, LLC Nitrogen and Sulfur Compounds 3401 TABLE 16.1.8.6.1 Reported vapor pressures of methanethiol at various temperatures and the coefficients for the vapor pressure equations log P = A – B/(T/K) (1) ln P = A – B/(T/K) (1a) log P = A – B/(C + t/°C) (2) ln P = A – B/(C + t/°C) (2a) log P = A – B/(C + T/K) (3) log P = A – B/(T/K) – C·log (T/K) (4) Russell et al. 1942 Stull 1947 Zwolinski & Wilhoit 1971 static-Hg manometer summary of literature data selected values t/°C P/Pa t/°C P/Pa t/°C P/Pa t/°C P/Pa –53.28 5484 –90.7 133.3 –70.3 1333 3.869 93326 –23.872 26859 –75.3 666.6 –61.5 2666 4.580 95992 –9.474 53235 –67.5 1333 –55.9 4000 5.275 98659 0.029 79913 –58.8 2666 –51.7 5333 5.956 101325 5.977 101410 –49.2 5333 –48.3 6666 25.0 202117 –43.1 7999 –45.4 7999 eq. 2 P/mmHg bp/K 279.12 –34.8 13332 –40.7 10666 A 7.03163 –22.1 26664 –36.87 13332 B 1015.547 eq. 4 P/mmHg –7.80 53329 –29.55 19998 C 238.706 A 18.27429 8.70 101325 –24.03 26664 bp/°C 5.956 B 1769.05 –19.54 33331 .HV/(kJ mol–1) = C 3.70248 mp/°C – –15.73 39997 at 25°C 23.8 –9.44 53329 at bp 24.57 –4.31 66661 0.051 79993 FIGURE 16.1.8.6.1 Logarithm of vapor pressure versus reciprocal temperature for methanethiol. Methanethiol: vapor pressure vs. 1/T 0.0 1.0 2.0 3.0 4.0 5.0 6.0 7.0 8.0 0.003 0.0034 0.0038 0.0042 0.0046 0.005 0.0054 1/(T/K) P( gol S ) aP/ Russell et al. 1942 Osborn & Scott 1980 Stull 1947 Zwolinski & Wilhoit 1971 b.p. = 5.9 °C © 2006 by Taylor & Francis Group, LLC 3402 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals 16.1.8.7 Ethanethiol Common Name: Ethanethiol Synonym: ethyl mercaptan, thioethyl alcohol, ethylhydrosulfide Chemical Name: ethanethiol CAS Registry No: 75-08-1 Molecular Formula: C2H6S, C2H5SH Molecular Weight: 62.134 Melting Point (C): –147.88 (Lide 2003) Boiling Point (°C): 35.0 (Stull 1947; Dreisbach 1961; Weast 1982–83; Boublik et al. 1984; Dean 1985; Lide 2003) Density (g/cm3 at 20°C): 0.83914, 0.83316 (20°C, 25°C, Dreisbach 1961) 0.8391 (Weast 1982–83) 0.8315 (25°C, Dean 1985) Molar Volume (cm3/mol): 74.0 (20°C, calculated-density) 77.4 (calculated-Le Bas method at normal boiling point) Dissociation Constant pKa: Enthalpy of Vaporization, .HV (kJ/mol): 27.30, 26.78 (25°C, bp, Dreisbach 1961) Enthalpy of Fusion, .Hfus (kJ/mol): Entropy of Fusion, .Sfus (J/mol K): Fugacity Ratio at 25°C (assuming .Sfus = 56 J/mol K), F: 1.0 Water Solubility (g/m3 or mg/L at 25°C): 15600 (Hine & Mookerjee 1975) 12000 (estimated-activity coefficient by headspace-GC/FID, Przyjazny et al. 1983) 15000 (Verschueren 1983) 6800 (Dean 1985) 6760 (20°C, Budavari 1989) 14800 (selected, Yaws et al. 1990) Vapor Pressure (Pa at 25°C or as indicated and reported temperature dependence equations. Additional data at other temperatures designated * are compiled at the end of this section): 74630* (interpolated-regression of tabulated data, temp range –76.7 to 35°C, Stull 1947) 70110* (24.933°C, ebulliometric method, measured range 0.405–66.14°C, McCullough et al. 1952) log (P/mmHg) = 6.95206 – 1084.531/(231.385 + t/°C); temp range 0.405–66.14°C (Antoine eq., ebulliometric method, McCullough et al. 1952) 70300 (calculated from determined data, Dreisbach 1961) log (P/mmHg) = 6.95206 – 1084.531/(231.385 + t/°C); temp range –40 to 100°C (Antoine eq. for liquid state, Dreisbach 1961) log (P/mmHg) = 6.95205 – 1084.531/(T/K + 231.385) (Antoine eq., Osborn & Douslin 1966) 66660*, 70290 (23.613°C, interpolated-Antoine eq., Zwolinski & Wilhoit 1971) log (P/mmHg) = 6.95026 – 1084.531/(231.385 + t/°C); temp range –49.2 to 55.83°C (liquid, Antoine eq., Zwolinski & Wilhoit 1971) 70320 (calculated-Antoine eq. of Boublik et al. 1973, Przyjazny et al. 1983) 58660 (20°C, Verschueren 1983) 70290 (interpolated-Antoine eq., Boublik et al. 1984) log (P/kPa) = 6.0768 – 1084.455/(231.374 + t/°C), temp range 0.405–66.115°C (Antoine eq. from reported exptl. data of McCullough et al. 1952, Boublik et al. 1984) 70300 (calculated-Antoine eq., Dean 1985, 1992) SH © 2006 by Taylor & Francis Group, LLC Nitrogen and Sulfur Compounds 3403 log (P/mmHg) = 6.95206 – 1084.531/(231.39 + t/°C); temp range –49 to 56°C (Antoine eq., Dean 1985, 1992) log (PL/kPa) = 6.07243 – 1081.984/(–42.085 + T/K), temp range 273–340 K (Antoine eq.-I, Stephenson & Malanowski 1987) log (PL/kPa) = 6.08253 – 1086.982/(–41.517 + T/K), temp range 273–313 K (Antoine eq.-II, Stephenson & Malanowski 1987) log (PL/kPa) = 6.10279 – 1099.374/(–39.807 + T/K), temp range 303–375 K (Antoine eq.-III, Stephenson & Malanowski 1987) log (PL/kPa) = 6.42565 – 1328.598/(–6.231 + T/K), temp range 365–448 K (Antoine eq.-IV, Stephenson & Malanowski 1987) log (PL/kPa) = 7.84948 – 2874.377/(200.657 + T/K), temp range 442–499 K (Antoine eq.-V, Stephenson & Malanowski 1987) log (P/mmHg) = 29.2763 – 2.2725 . 103/(T/K) – 7.7769·log (T/K) – 3.8954 . 10–11·(T/K) + 3.517 . 10–6·(T/K)2; temp range 125–499 K (vapor pressure eq., Yaws 1994) Henry’s Law Constant (Pa·m3/mol at 25°C or as indicated and reported temperature dependence equations): 278.1 (exptl., Hine & Mookerjee 1975) 298, 366.6 (calculated-group contribution, calculated-bond contribution, Hine & Mookerjee 1975) 451 (20°C, headspace-GC, Vitenberg et al. 1975) 360.3 (distilled water, headspace-GC/FID, measured range 25–70°C, data in graph, Przyjazny et al. 1983) log (1/KAW) = 1486.1/(T/K) – 4.147; temp range 25–70°C (headspace-GC, Przyjazny et al. 1983) 292.4 (computed-vapor-liquid equilibrium VLE data, Yaws et al. 1991) 278, 96.44 (quoted, calculated-molecular structure, Russell et al. 1992) 292.5 (20°C, selected from literature experimentally measured data, Staudinger & Roberts 1996, 2001) log KAW = 4.147 – 1486/(T/K) (van’t Hoff eq. derived from literature data, Staudinger & Roberts 2001) Octanol/Water Partition Coefficient, log KOW: Octanol/Air Partition Coefficient, log KOA: Bioconcentration Factor, log BCF: Sorption Partition Coefficient, log KOC: Environmental Fate Rate Constants, k, or Half-Lives, t.: Volatilization: Photolysis: Oxidation: rate constant k, for gas-phase second order rate constants, kOH for reaction with OH radical, kNO3 with NO3 radical and kO3 with O3 or as indicated, *data at other temperatures and the Arrhenius expression see reference: kO(3P)* = 3.0 . 10–12 cm3 ± molecule–1 s–1 for gas-phase reaction with O(3P) atom at 298 K, measured range 257–495 K (Slagle et al. 1978) kOH = 3.67 . 10–11 cm3 molecule–1 s–1 at 296 K (discharge flow-RF, Lee & Tang 1983) kOH = 2.70 . 10–11 cm3 molecule–1 s–1 at 293 K (discharge flow-EPR, Mac Leod et al. 1984) kOH* = 4.26 . 10–11 cm3 molecule–1 s–1 at 298 K, measured range 252–425 K (flash photolysis-resonance fluorescence, Wine et al. 1984) kOH* = 4.65 . 10–11 cm3 molecule–1 s–1 at 298 K (recommended, Atkinson 1985) kOH = 4.65 . 10–11 cm3 molecule–1 s–1 at 300 K (relative rate method, Barnes et al. 1986) kOH* = 4.68 . 10–11 cm3 molecule–1 s–1 at 298 K (recommended, Atkinson 1989) kNO3 = (1.21 ± 0.28) . 10–12 cm3 molecule–1 s–1 at 298K (relative rate method, Mac Leod et al. 1986; quoted, Atkinson 1991) Hydrolysis: Biodegradation: Biotransformation: Bioconcentration, Uptake (k1) and Elimination (k2) Rate Constants: Half-Lives in the Environment: © 2006 by Taylor & Francis Group, LLC 3404 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals TABLE 16.1.8.7.1 Reported vapor pressures of ethanethiol at various temperatures and the coefficients for the vapor pressure equations log P = A – B/(T/K) (1) ln P = A – B/(T/K) (1a) log P = A – B/(C + t/°C) (2) ln P = A – B/(C + t/°C) (2a) log P = A – B/(C + T/K) (3) log P = A – B/(T/K) – C·log (T/K) (4) Stull 1947 McCullough et al. 1952 Zwolinski & Wilhoit 1971 summary of literature data ebulliometry selected values t/°C P/Pa t/°C P/Pa t/°C P/Pa t/°C P/Pa –76.7 133.3 0.405 25007 –49.2 1333 eq. 2 P/mmHg –59.1 666.6 5.236 31160 –39.5 2666 A 6.95206 –50.2 1333 10.111 38547 –33.3 4000 B 1084.531 –40.7 2666 15.017 47359 –28.7 5333 C 231.385 –29.8 5333 19.954 57803 –24.9 6666 bp/°C 35.003 –22.4 7999 24.933 70109 –21.77 7999 .HV/(kJ mol–1) = –13.0 13332 29.944 84525 –16.58 10666 at 25°C 27.30 1.50 26664 35.000 101325 –12.38 13332 at bp 26.78 17.7 53329 40.092 120798 –4.304 19998 35.0 101325 45.221 142368 1.796 26664 50.390 169052 6.758 33331 mp/°C –121 55.604 198530 10.972 39997 60.838 232087 17.932 53329 66.115 270110 23.613 66661 28.451 79993 Antoine eq. 32.686 93326 eq. 2 P/mmHg 33.475 95992 A 6.95206 34.247 98659 B 1084.531 35.003 101325 C 231.385 25.0 70288 © 2006 by Taylor & Francis Group, LLC Nitrogen and Sulfur Compounds 3405 FIGURE 16.1.8.7.1 Logarithm of vapor pressure versus reciprocal temperature for ethanethiol. Ethanethiol: vapor pressure vs. 1/T 0.0 1.0 2.0 3.0 4.0 5.0 6.0 7.0 8.0 0.0028 0.0032 0.0036 0.004 0.0044 0.0048 0.0052 1/(T/K) P( gol S ) aP / McCullough et al. 1952 Stull 1947 Zwolinski & Wilhoit 1971 b.p. = 35 °C © 2006 by Taylor & Francis Group, LLC 3406 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals 16.1.8.8 1-Propanethiol Common Name: 1-Propanethiol Synonym: n-propyl mercaptan, 1-mercaptopropane Chemical Name: 1-propanethiol CAS Registry No: 107-03-9 Molecular Formula: C3H8S, CH3CH2CH2SH Molecular Weight: 76.171 Melting Point (°C): –113.13 (Lide 2003) Boiling Point (°C): 67.8 (Lide 2003) Density (g/cm3): 0.8411 (20°C, Weast 1982–83) Dissociation Constant, pKa: Molar Volume (cm3/mol): 99.6 (calculated-density, Stephenson & Malanowski 1987) Enthalpy of Vaporization, .HV (kJ/mol): 31.88, 29.53 (25°C, bp, Zwolinski & Wilhoit 1971) Enthalpy of Sublimation, .Hsubl (kJ/mol): Enthalpy of Fusion, .Hfus (kJ/mol): Entropy of Fusion, .Sfus (J/mol K): Fugacity Ratio at 25°C (assuming .Sfus = 56 J/mol K), F: 1.0 Water Solubility (g/m3 or mg/L at 25°C): 3800 (estimated-activity coefficient by headspace-GC/FID, Przyjazny et al. 1983) Vapor Pressure (Pa at 25°C or as indicated and reported temperature dependence equations. Additional data at other temperatures designated * are compiled at the end of this section): 13332* (15.3°C, summary of literature data, temp range –56.0 to 67.4°C, Stull 1947) 19920* (24.275°C, ebulliometry, measured range 24.3–102.088°C, Pennington et al. 1956) log (P/mmHg) = 6.92846 – 1183.307/(T/K + 224.624); temp range 24.3–102.088°C (Antoine eq., ebulliometry, Pennington et al. 1956; Osborn & Douslin 1966) 20558* (interpolated-Antoine eq., temp range –25 to 90.73°C, Zwolinski & Wilhoit 1971) log (P/mmHg) = 6.92846 – 1183.307/(224.624 + t/°C); temp range –25 to 90.73°C (Antoine eq., Zwolinski & Wilhoit 1971) 20569 (calculated-Antoine eq. of Boublik et al. 1973, Przyjazny et al. 1983) log (P/kPa) = 6.05331 – 1183.265/(224.618 + t/°C), temp range 24.27–102.088°C (Antoine eq. derived from Pennington et al. 1956 data, Boublik et al. 1984) log (PL/kPa) = 6.05019 – 1181.703/(–48.687 + T/K), temp range 296–376 K, (Antoine eq., Stephenson & Malanowski 1987) log (P/mmHg) = 6.92846 – 1183.307/(224.62 + t/°C), temp range –25 to 91°C (Antoine eq., Dean 1992) Henry’s Law Constant (Pa m3/mol at 25°C or as indicated): 414 (distilled water, headspace-GC/FID, measured range 25–70°C, data in graph, Przyjazny et al. 1983) log (1/KAW) = 1552.2/(T/K) – 4.428; temp range 25–70°C (headspace-GC, Przyjazny et al. 1983) 331 (20°C, selected from literature experimentally measured data, Staudinger & Roberts 2001) log KAW = 4.428 – 1552/(T/K), (van’t Hoff eq. derived from literature data, Staudinger & Roberts 2001) Octanol/Water Partition Coefficient, log KOW: 1.81 (shake flask, Log P Database, Hansch & Leo 1987) 1.81 (recommended, Sangster 1993) 1.81 (recommended, Hansch et al. 1995) SH © 2006 by Taylor & Francis Group, LLC Nitrogen and Sulfur Compounds 3407 Octanol/Air Partition Coefficient, log KOA: Bioconcentration Factor, log BCF or log KB: Sorption Partition Coefficient, log KOC: Environmental Fate Rate Constants, k, and Half-Lives, t.: Volatilization: Photolysis: Oxidation: rate constant k, for gas-phase second order rate constants, kOH for reaction with OH radical, kNO3 with NO3 radical and kO3 with O3 or as indicated, *data at other temperatures see reference: kOH* = (4.18–4.56) . 10–11 cm3 molecule–1 s–1 at 298 K, measured range 257–419 K (flash photolysisresonance fluorescence, Wine et al. 1984) Hydrolysis: Biodegradation: Biotransformation: Bioconcentration and Uptake and Elimination Rate Constants (k1 and k2): Half-Lives in the Environment: TABLE 16.1.8.8.1 Reported vapor pressures of 1-propanethiol at various temperatures and the coefficients for the vapor pressure equations log P = A – B/(T/K) (1) ln P = A – B/(T/K) (1a) log P = A – B/(C + t/°C) (2) ln P = A – B/(C + t/°C) (2a) log P = A – B/(C + T/K) (3) log P = A – B/(T/K) – C·log (T/K) (4) Stull 1947 Pennington et al. 1956 Zwolinski & Wilhoit 1971 summary of literature data ebulliometry selected values t/°C P/Pa t/°C P/Pa t/°C P/Pa –56.0 133.3 24.275 18820 –25.0 1333 –36.3 666.6 29.563 25007 –14.3 2666 –26.3 1333 34.891 31160 –7.60 4000 –15.4 2666 40.254 38547 –2.50 5333 –3.20 5333 45.663 47359 1.65 6666 4.60 7999 51.113 57803 5.13 7999 15.3 13332 56.605 70109 10.84 10666 31.5 26664 62.139 84525 15.47 13332 49.2 53329 67.719 101325 24.369 19998 67.4 101325 73.341 120798 31.092 26664 79.004 143268 36.562 33331 mp/°C –112 84.710 169052 41.208 39997 90.464 198543 48.884 53329 96.225 232087 55.151 66661 102.088 270110 60.489 79993 65.163 93326 bp/°C 67.72 66.034 95992 Antoine eq. 66.886 98659 © 2006 by Taylor & Francis Group, LLC 3408 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals TABLE 16.1.8.8.1 (Continued) Stull 1947 Pennington et al. 1956 Zwolinski & Wilhoit 1971 summary of literature data ebulliometry selected values t/°C P/Pa t/°C P/Pa t/°C P/Pa eq. 2 P/mmHg 67.720 101325 A 6.92846 25.0 20558 B 1183.307 C 224.824 eq. 2 P/mmHg A 6.92846 data also fitted to Cox eq. B 1193.307 C 224.624 bp/°C 67.72 .HV/(kJ mol–1) = at 25°C 31.88 at bp 29.53 FIGURE 16.1.8.8.1 Logarithm of vapor pressure versus reciprocal temperature for 1-propanethiol. 1-Propanethiol: vapor pressure vs. 1/T 0.0 1.0 2.0 3.0 4.0 5.0 6.0 7.0 8.0 0.0026 0.003 0.0034 0.0038 0.0042 0.0046 1/(T/K) P( gol S ) aP/ Pennington et al. 1956 Stull 1947 Zwolinski & Wilhoit 1971 b.p. = 76.8 °C © 2006 by Taylor & Francis Group, LLC Nitrogen and Sulfur Compounds 3409 16.1.8.9 1-Butanethiol (Butyl mercaptan) Common Name: 1-Butanethiol Synonym: butyl mercaptan, n-butyl mercaptan Chemical Name: 1-butanethiol CAS Registry No: 109-79-5 Molecular Formula: C4H10S, CH3(CH2)3SH Molecular Weight: 90.187 Melting Point (°C): –115.7 (Weast 1982–83; Riddick et al. 1986; Stephenson & Malanowski 1987; Lide 2003) Boiling Point (°C): 98.5 (Lide 2003) Density (g/cm3 at 25°C): 0.8337 (20°C, Weast 1982–83) 0.84159, 0.83674 (20°C, 25°C, Riddick et al. 1986) Molar Volume (cm3/mol): 107.8 (calculated-density, Stephenson & Malanowski 1987) 121.8 (calculated-Le Bas method at normal boiling point) Dissociation Constant pKa: Enthalpy of Vaporization, .HV (kJ/mol): 36.53, 32.225 (25°C, bp, Riddick et al. 1986) Enthalpy of Fusion, .Hfus (kJ/mol): 10.46 (Riddick et al. 1986) Entropy of Fusion, .Sfus (J/mol K): Fugacity Ratio at 25°C (assuming .Sfus = 56 J/mol K), F: 1.0 Water Solubility (g/m3 or mg/L at 25°C): 597 (Riddick et al. 1986) 600 (selected, Yaws et al. 1990) Vapor Pressure (Pa at 25°C and reported temperature dependence equations. Additional data at other temperatures designated * are compiled at the end of this section): 19920* (51.409°C, ebulliometry, measured range 51.4–135.7°C, Scott et al. 1957) log (P/mmHg) = 6.92754 – 1281.018/(T/K + 218.100) (Antoine eq., Osborn & Douslin 1966) 5330*, 6070 (22.4°C, interpolated-Antoine eq., Zwolinski & Wilhoit 1971) log (P/mmHg) = 6.92754 – 1281.018/(218.10 + t/°C); temp range –2.0 to 123.37°C (liquid, Antoine eq., Zwolinski & Wilhoit 1971) log (P/kPa) = 6.05296 – 1281.344/(218.139 + t/°C), temp range 51.409–135.7°C (Antoine eq. derived from Scott et al. 1957 data, Boublik et al. 1984) 6070 (Riddick et al. 1986) log (P/kPa) = 6.05244 – 1281.018/(218.10 + t/°C), temp range not specified (Antoine eq., Riddick et al. 1986) log (PL/kPa) = 6.05011 – 1279.95/(–55.132 + T/K), temp range 323–409 K (Antoine eq., Stephenson & Malanowski 1987) log (P/mmHg) = 6.92754 – 1281.018/(218.10 + t/°C), temp range –2 to 123°C (Antoine eq., Dean 1992) log (P/mmHg) = 36.2672 – 3.0452 . 103/(T/K) –9.9743·log (T/K) – 9.1432 . 10–11·(T/K) + 3.2087 . 10–6·(T/K)2; temp range 157–569 K (vapor pressure eq., Yaws 1994) Henry’s Law Constant (Pa m3/mol at 25°C or as indicated and reported temperature dependence equations): 460.7 (distilled water, headspace-GC/FID, measured range 25–70°C, data in graph, Przyjazny et al. 1983) log (1/KAW) = 1655.9/(T/K) – 4.823; temp range 25–70°C (headspace-GC, Przyjazny et al. 1983) 911.4 (computed-vapor-liquid equilibrium VLE data, Yaws et al. 1991) 363 (20°C, selected from literature experimentally measured data, Staudinger & Roberts 1996, 2001) log KAW = 4.823 – 1656/(T/K) (van’t Hoff eq. derived from literature data, Staudinger & Roberts 2001) SH © 2006 by Taylor & Francis Group, LLC 3410 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals Octanol/Water Partition Coefficient, log KOW: 2.28 (shake flask, Log P Database, Hansch & Leo 1987) 2.28 (recommended, Sangster 1989) 2.28 (recommended, Hansch et al. 1995) Octanol/Air Partition Coefficient, log KOA: Bioconcentration Factor, log BCF: Sorption Partition Coefficient, log KOC: Environmental Fate Rate Constants, k, or Half-Lives, t.: Volatilization: Photolysis: Oxidation: rate constant k, for gas-phase second order rate constants, kOH for reaction with OH radical, kNO3 with NO3 radical and kO3 with O3 or as indicated, *data at other temperatures see reference: kOH = 4.21 . 10–11 cm3 molecule–1 s–1 and kOH = 4.55 . 10–11 cm3 molecule–1 s–1 at 298 K (flash photolysisresonance fluorescence, Wine et al. 1984) kOH = 5.82 . 10–11 cm3 molecule–1 s–1 at 300 K (relative rate method, Barnes et al. 1986) kOH = 5.11 . 10–11 cm3 molecule–1 s–1 at 298 K (recommended, Atkinson 1989) Hydrolysis: Biodegradation: Biotransformation: Bioconcentration, Uptake (k1) and Elimination (k2) Rate Constants: Half-Lives in the Environment: TABLE 16.1.8.9.1 Reported vapor pressures of 1-butanethiol at various temperatures and the coefficients for the vapor pressure equations log P = A – B/(T/K) (1) ln P = A – B/(T/K) (1a) log P = A – B/(C + t/°C) (2) ln P = A – B/(C + t/°C) (2a) log P = A – B/(C + T/K) (3) log P = A – B/(T/K) – C·log (T/K) (4) Scott et al. 1957 Zwolinski & Wilhoit 1971 ebulliometry selected values t/°C P/Pa t/°C P/Pa t/°C P/Pa 51.409 19920 –2.0 1333 95.687 93326 57.130 25007 9.60 2666 96.630 95992 62.897 31169 16.9 4000 97.553 98659 68.710 38547 22.4 5333 98.456 101325 74.567 47359 26.9 6666 25.0 7399 80.472 57803 30.67 7999 eq. 2 P/mmHg 86.418 70109 36.86 10666 A 6.92854 92.414 84525 41.87 13332 B 1281.018 98.454 101325 51.506 19998 C 218.100 104.544 120798 58.786 26664 bp/°C 98.456 110.682 143268 64.170 33331 .HV/(kJ mol–1) = 116.863 169052 69.742 39997 at 25°C 36.53 123.088 198530 78.056 53329 at bp 32.23 129.362 232087 84.844 66661 135.678 170110 90.625 79993 © 2006 by Taylor & Francis Group, LLC Nitrogen and Sulfur Compounds 3411 FIGURE 16.1.8.9.1 Logarithm of vapor pressure versus reciprocal temperature for 1-butanethiol. 1-Butanethiol: vapor pressure vs. 1/T 0.0 1.0 2.0 3.0 4.0 5.0 6.0 7.0 8.0 0.0024 0.0026 0.0028 0.003 0.0032 0.0034 0.0036 0.0038 0.004 1/(T/K) P ( gol S ) aP/ Scott et al. 1957 Zwolinski & Wilhoit 1971 b.p. = 98.5 °C © 2006 by Taylor & Francis Group, LLC 3412 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals 16.1.8.10 Benzenethiol Common Name: Benzenethiol Synonym: thiophenol, phenyl mercaptan, mercaptobenzene Chemical Name: benzenethiol CAS Registry No: 108-98-5 Molecular Formula: C6H6S, C6H5SH Molecular Weight: 110.177 Melting Point (°C): –14.93 (Lide 2003) Boiling Point (°C): 169.1 (Lide 2003) Density (g/cm3): 1.0766 (20°C, Weast 1982–83) Dissociation Constant, pKa: 6.615 (Riddick et al. 1986) Molar Volume (cm3/mol): 102.7 (calculated-density, Stephenson & Malanowski 1987) 106.8 (calculated-Le Bas method at normal boiling point) Enthalpy of Vaporization, .HV (kJ/mol): 45.35, 36.97 (25°C, bp, Riddick et al 1986) Enthalpy of Sublimation, .Hsubl (kJ/mol): Enthalpy of Fusion, .Hfus (kJ/mol): 11.45 (calorimetry at triple pt 258.27 K, Scott et al. 1956) 11.447 (Riddcik et al. 1986) Entropy of Fusion, .Sfus (J/mol K): Fugacity Ratio at 25°C (assuming .Sfus = 56 J/mol K), F: 1.0 Water Solubility (g/m3 or mg/L at 25°C): Vapor Pressure (Pa at 25°C or as indicated and reported temperature dependence equations. Additional data at other temperatures designated * are compiled at the end of this section): 133* (18.6°C, summary of literature data, temp range 18.6–168°C, Stull 1947) 1333* (51.5°C, ebulliometry, measured range 51.5–167.0°C, Vonterres et al. 1955) 19920* (114.543°C, ebulliometry, measured range 114.543–7212.160°C, Scott et al. 1956) log (P/mmHg) = 6.99019 – 1529.454/(230.048 + t/°C); temp range 114.5–212°C (comparative ebulliometry, data fitted to Antoine eq., Scott et al. 1956) log (P/mmHg) = A ± [1 – 442.298/(T/K)], where log A = 0.87370 – 6.4975 . 10–4 ± (T/K) + 5.2309 . 10–7 ± (T/K)2; measured range 114.5–212°C (data fitted to Cox eq., comparative ebulliometry, Scott et al. 1956) 1333* (52.28°C, derived from compiled data, temp range 52.3–198°C, Zwolinski & Wilhoit 1971) log (P/mmHg) = 6.99019 – 1529.454/(230.048 + t/°C); temp range 52.3–198°C (Antoine eq., Zwolinski & Wilhoit 1971) log (P/kPa) = 6.11539 – 1529.668/(203.074 + t/°C), temp range 114.54–212.16°C (Antoine eq. derived from Scott et al. 1956 data, Boublik et al. 1984) 397 (selected, Riddick et al. 1986) log (P/kPa) = 6.11509 – 1529.46/(t/°C + 258.21); temp range not specified (Antoine eq., Riddick et al. 1986) log (PL/kPa) = 6.11531 – 1530.286/(–69.948 + T/K); temp range 385–486 K (Antoine eq., Stephenson & Malanowski 1987) log (P/mmHg) = –5.4919 – 2.8549 . 103/(T/K) + 8.1770·log (T/K) – 1.9494 . 10–2·(T/K) + 9.2817 . 10–6·(T/K)2; temp range 258–69 K (vapor pressure eq., Yaws et al. 1994) SH © 2006 by Taylor & Francis Group, LLC Nitrogen and Sulfur Compounds 3413 Henry’s Law Constant (Pa m3/mol at 25°C): Octanol/Water Partition Coefficient, log KOW: 2.52 (shake flask, Log P Database, Hansch & Leo 1987) 2.52 (recommended, Sangster 1989) 2.52 (recommended, Hansch et al. 1995) Octanol/Air Partition Coefficient, log KOA: Bioconcentration Factor, log BCF or log KB: Sorption Partition Coefficient, log KOC: Environmental Fate Rate Constants, k, and Half-Lives, t.: Half-Lives in the Environment: TABLE 16.1.8.10.1 Reported vapor pressures of benzenethiol at various temperatures and the coefficients for the vapor pressure equations log P = A – B/(T/K) (1) ln P = A – B/(T/K) (1a) log P = A – B/(C + t/°C) (2) ln P = A – B/(C + t/°C) (2a) log P = A – B/(C + T/K) (3) log P = A – B/(T/K) – C·log (T/K) (4) Stull 1947 Vonterres et al. 1955 Scott et al. 1956 Zwolinski & Wilhoit 1971 summary of literature data ebulliometry comparative ebulliometry selected values t/°C P/Pa t/°C P/Pa t/°C P/Pa t/°C P/Pa 18.6 133.3 51.5 1333 114.543 19920 52.28 1333 43.7 666.6 71.5 5333 121.191 25007 65.79 2666 56.0 1333 87.8 6666 127.897 31160 74.38 4000 69.7 2666 97.4 9999 134.649 38547 80.81 5333 84.2 5333 105.5 13332 141.447 47359 86.01 6666 93.9 7999 116.3 19998 148.294 57803 90.40 7999 106.6 13332 124.5 26664 155.194 70109 97.61 10666 125.8 26664 131.3 33330 162.140 84525 103.444 13332 146.7 53329 136.5 39997 176.188 120789 114.655 19998 168.0 101325 141.5 46663 183.278 143268 123.120 26664 146.0 53329 190.426 169052 130.003 33331 mp/°C - 149.7 59995 197.623 198530 135.847 39997 153.0 66661 204.867 232087 145.496 53329 156.0 73327 212.160 270110 153.367 66661 159.0 79993 160.067 79993 162.0 86659 mp/K 258.27 165.932 93326 165.0 93325 .Hfus/(kJ mol–1) = 11.447 167.024 95992 167.0 101325 bp/K 416.9 168.092 98659 169.138 101325 (Continued) © 2006 by Taylor & Francis Group, LLC 3414 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals TABLE 16.1.8.10.1 (Continued) Stull 1947 Vonterres et al. 1955 Scott et al. 1956 Zwolinski & Wilhoit 1971 summary of literature data ebulliometry comparative ebulliometry selected values t/°C P/Pa t/°C P/Pa t/°C P/Pa t/°C P/Pa eq. 2 P/mmHg 169.653 102658 A 6.99019 170.163 103991 B 1529.454 171.167 106658 C 203.048 temp range 114–212°C eq. 2 P/mmHg A 6.99019 B 1529.454 C 203.048 bp/°C .HV/(kJ mol–1) = 40.6 at normal bp FIGURE 16.1.8.10.1 Logarithm of vapor pressure versus reciprocal temperature for benzenethiol. Benzenethiol: vapor pressure vs. 1/T 0.0 1.0 2.0 3.0 4.0 5.0 6.0 7.0 8.0 0.0018 0.0022 0.0026 0.003 0.0034 0.0038 0.0042 0.0046 1/(T/K) P ( gol S ) aP/ Vonterres et al. 1955 Scott et al. 1956 Stull 1947 Zwolinski & Wilhoit 1971 b.p. = 169.1 °C m.p. = -14.93 °C © 2006 by Taylor & Francis Group, LLC Nitrogen and Sulfur Compounds 3415 16.1.8.11 Thiophene Common Name: Thiophene Synonym: thiofuran Chemical Name: thiophene, thiofuran CAS Registry No: 110-02-1 Molecular Formula: C4H4S Molecular Weight: 84.140 Melting Point (°C): –38.21 (Lide 2003) Boiling Point (°C): 84.0 (Lide 2003) Density (g/cm3 at 20°C): 1.06485, 1.05887 (20°C, 25°C, Dreisbach 1955) 1.0649 (Weast 1982–83) 1.06482, 1.05884 (20°C, 25°C, Riddick et al. 1986) Molar Volume (cm3/mol): 79.0 (20°C, calculated from density) 88.10 (calculated-Le Bas method at normal boiling point) Dissociation Constant pKa: Enthalpy of Vaporization, .HV (kJ/mol): 34.6, 31.472 (25°C, bp, Riddick et al. 1986) Enthalpy of Fusion, .Hfus (kJ/mol): 5.088 (Riddick et al. 1986) Entropy of Fusion, .Sfus (J/mol K): Fugacity Ratio at 25°C (assuming .Sfus = 56 J/mol K), F: 1.0 Water Solubility (g/m3 or mg/L at 25°C): 3015 (shake flask-GC, Price 1976) 3900 (estimated-activity coefficient by headspace-GC, Przyjazny et al. 1983) 3600 (18°C, Verschueren 1983) 3020 (selected, Yaws et al. 1990) Vapor Pressure (Pa at 25°C or as indicated and reported temperature dependence equations. Additional data at other temperatures designated * are compiled at the end of this section): 9670* (interpolated-regression of tabulated data, temp range –40.7 to 81.4°C, Stull 1947) 7998 (20.1°C, Stull 1947) 10622* (ebulliometry and manometry, measured range 0–84.155°C, Waddington et al. 1949) 10620 (calculated from determined data, Dreisbach 1955) log (P/mmHg) = 6.95926 – 1246.038/(221.354 + t/°C), temp range 5–155°C (Antoine eq. for liquid state, Dreisbach 1955) 482307* (148.89°C, static-Bourdon gauge, measured range 148.89–304.44°C, Kobe et al. 1956) 44930* (60.3 °C, isoteniscope/manometry, measured range 60.3–100.3 °C, Eon et al. 1971) 10670, 10660* (25.09°C, interpolated-Antoine eq., Zwolinski & Wilhoit 1971) log (P/mmHg) = 6.95926 – 1246.01/(221.35 + t/°C); temp range –12.3 to 108.1°C (Antoine eq., Zwolinski & Wilhoit 1971) log (P/mmHg) = [–0.2185 . 8748.3/(T/K)] + 8.273276; temp range –40.7 to 84.4°C (Antoine eq., Weast 1972–73) 2450 (calculated-Cox eq., Chao et al. 1983) log (P/atm) = [1 – 394.395/(T/K)] . 10^{0.901276 – 10.3229 . 10–4 ± (T/K) + 21.9193 . 10–7 ± (T/K)2}; temp range: 278.35–443.60 K (Cox eq., Chao et al. 1983) S © 2006 by Taylor & Francis Group, LLC 3416 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals 7998, 13330 (20°C, 30°C, quoted, Verschueren 1983) 10622, 10620 (quoted exptl., calculated-Antoine eq., Boublik et al. 1984) log (P/kPa) = 6.1336 – 1260.606/(222.787 + t/°C), temp range 0–40°C (Antoine eq. from reported exptl. data, Boublik et al. 1984) log (P/kPa) = 6.0723 – 1138.803/(220.477 + t/°C), temp range 39.9–119.79°C (Antoine eq. from reported exptl. data, Boublik et al. 1984) 10620 (calculated-Antoine eq., Dean 1985, 1992) log (P/mmHg) = 6.95926 – 1246.02/(221.35 + t/°C), temp range –12 to 108°C (Antoine eq., Dean l985, 1992) 10620 (selected, Riddick et al. 1986) log (P/kPa) = 6.08416 – 1246.02/(221.35 + t/°C), temp range not specified (Antoine eq., Riddick et al. 1986) 10600 (extrapolated-Antoine eq., Stephenson & Malanowski 1987) log (PS/kPa) = 9.84733 – 2447.236/(T/K), temp range 195–228 K (solid, Antoine eq.-I, Stephenson & Malanowski 1987) log (PL/kPa) = 6.06132 – 1232.35/(–53.438 + T/K), temp range 311–393 K (liquid, Antoine eq.-II, Stephenson & Malanowski 1987) log (P/mmHg) = 36.6016 – 2.9794 . 103/(T/K) – 10.104·log (T/K) + 1.1445 . 10–9·(T/K) + 3.2472 . 10–6·(T/K)2; temp range 235–579 K (vapor pressure eq., Yaws et al. 1994) Henry’s Law Constant (Pa·m3/mol at 25°C or as indicated and reported temperature dependence equations): 224, 236, 230 (headspace-GC, concn. of 10, 1.0 and 0.1 ppm by weight, measured range 25–70°C, data presented in graph, Przyjazny et al. 1983) log (1/KAW) = 1563.6/(T/K) – 4.199; temp range 25–70°C (headspace-GC, concn of 10 ppm by weight, Przyjazny et al. 1983) log (1/KAW) = 1580.0/(T/K) – 4.277; temp range 25–70°C (headspace-GC, concn of 1.0 ppm by weight, Przyjazny et al. 1983) log (1/KAW) = 1661.9/(T/K) – 4.542; temp range 25–70°C (headspace-GC, concn of 0.1 ppm by weight, Przyjazny et al. 1983) 223.3 (calculated-P/C with selected values) 296 (computed-vapor-liquid equllibrium VLE data, Yaws et al. 1991) 182 (20°C, selected from literature experimentally measured data, Staudinger & Roberts 1996, 2001) log KAW = 4.542 – 1662/(T/K), (van’t Hoff eq. derived from literature data, Staudinger & Roberts 2001) Octanol/Water Partition Coefficient, log KOW: 1.81 ± 0.01 (shake flask-UV, Iwasa et al. 1965) 1.79 (calculated-f const., Rekker 1977) 1.74 (HPLC-RV correlation, Garst 1984) 1.82 (shake flask, Log P Database, Hansch & Leo 1987) 1.81 (recommended, Sangster 1989, 1993) 1.82 (shake flask-UV, Yamagami & Takao 1992) 1.81 (recommended, Hansch et al. 1995) Octanol/Air Partition Coefficient, log KOA: Bioconcentration Factor, log BCF: Sorption Partition Coefficient, log KOC: Environmental Fate Rate Constants, k, or Half-Lives, t.: Volatilization: Photolysis: Oxidation: rate constant k, for gas-phase second order rate constants, kOH for reaction with OH radical, kNO3 with NO3 radical and kO3 with O3 or as indicated, *data at other temperatures and the Arrhenius expression see reference: © 2006 by Taylor & Francis Group, LLC Nitrogen and Sulfur Compounds 3417 kOH = (9.58 ± 0.38) . 10–12 cm3 molecule–1 s–1 with calculated atmospheric lifetime . ~ 28 h; and kO3 < 6 . 10–20 cm3 molecule–1 s–1 at 298 ± 2 K and kO(3P) = 4.9 . 10–12 cm3 molecule–1 s–1 for reaction with O(3P) atom at room temp. (relative rate method, Atkinson et al 1983) kO3 < 6 . 10–20 cm3 molecule–1 s–1 with a loss rate of < 0.004 d–1, kOH = 9.6 . 10–12 cm3 molecule–1 s–1 with a loss rate of 0.8 d–1; kNO3 = 3.2 . 10–14 cm3 molecule–1 s–1 with a loss rate of 0.7 d–1 at room temp. (review, Atkinson & Carter 1984) kOH* = (9.37, 9.57) . 10–12 cm3 molecule–1 s–1 at 298 K, measured range 255–425 K (flash photolysisresonance fluorescence, Wine & Thompson 1984) kOH = 9.49 . 10–12 cm3 molecule–1 s–1 at 298 K (recommended, Atkinson 1985) kO3 < 6 . 10–20 cm3 molecule–1 s–1 with a loss rate of < 0.004 d–1, kOH = 9.70 . 10–12 cm3 ± molecule–1 s–1 with a loss rate of 0.4 d–1, and kNO3 = 3.2 . 10–14 cm3 molecule–1 s–1 with a loss rate of 0.7 d–1 at room temp. (review, Atkinson 1985) kNO3 = (3.2 ± 0.7) . 10–14 cm3 molecule–1 s–1 with a calculated lifetime of 36 h and a loss rate of 0.7 d–1 assuming 2.4 . 108 NO3 radicals/cm3 in nighttime air at 295 ± 1 K in the atmosphere (relative rate technique, Atkinson et al. 1985) kO3 < 6 . 10–20 cm3 molecule–1 s–1 with a calculated tropospheric lifetime . > 270 d, kOH = 9.70 . 10–12 cm3 molecule–1 s–1 with a calculated lifetime of 29 h during daytime hours, and kNO3 = 3.2 . 10–14 cm3 molecule–1 s–1 with a calculated lifetime of 36 h at room temp. (review, Atkinson 1985) kOH* = 9.53 . 10–12 cm3 molecule–1 s–1 at 298 K (recommended, Atkinson 1989) kNO3 = 3.93 . 10–14 cm3 molecule–1 s–1, independent of temperature over the range 272–296 K (recommended, Atkinson 1991) kOH(calc) = 14.81 . 10–12 cm3 molecule–1 s–1 at room temp. (molecular orbital calculations, (Klamt 1993) Hydrolysis: Biodegradation: Biotransformation: Bioconcentration, Uptake (k1) and Elimination (k2) Rate Constants: Half-Lives in the Environment: Air: atmospheric lifetime of ~28 h due to reactions with OH radical (Atkinson et al. 1983); calculated gas-phase lifetime of 29 h for the reaction with OH radical during daytime hours, calculated lifetime of 36 h for reaction with NO3 radical and a calculated lifetime > 270 d for reaction with O3 at room temp. (Atkinson et al. 1985) TABLE 16.1.8.11.1 Reported vapor pressures of thiophene at various temperatures and the coefficients for the vapor pressure equations log P = A – B/(T/K) (1) ln P = A – B/(T/K) (1a) log P = A – B/(C + t/°C) (2) ln P = A – B/(C + t/°C) (2a) log P = A – B/(C + T/K) (3) log P = A – B/(T/K) – C·log (T/K) (4) Stull 1947 Waddington et al. 1949 Kobe et al. 1956 Zwolinski & Wilhoit 1971 summary of literature data manometry and ebulliometry static-Bourdon gauge selected values t/°C P/Pa t/°C P/Pa t/°C P/Pa t/°C P/Pa static method –40.7 133 0 2858 148.89 482307 –12.3 1333 –20.8 666.6 15 6497 154.44 585659 –1.10 2666 –10.9 1333 20 8355 160.00 620109 5.94 4000 0.0 2666 25 10627 165.56 730351 11.24 5333 12.5 5333 30 13398 171.11 813032 15.52 6666 20.1 7999 35 16733 176.67 895713 19.14 7999 (Continued) © 2006 by Taylor & Francis Group, LLC 3418 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals TABLE 16.1.8.11.1 (Continued) Stull 1947 Waddington et al. 1949 Kobe et al. 1956 Zwolinski & Wilhoit 1971 summary of literature data manometry and ebulliometry static-Bourdon gauge selected values t/°C P/Pa t/°C P/Pa t/°C P/Pa t/°C P/Pa 30.5 13332 40 20736 182.22 992174 25.09 10666 46.5 26664 ebulliometric method 187.78 1088636 29.90 13332 64.7 53329 39.061 19920 193.33 1198877 39.15 19998 81.4 101325 44.560 25007 198.89 1316009 46.14 26664 50.094 31160 204.44 1440031 51.82 33331 mp/°C –38.3 55.663 38547 210.00 1584723 56.65 39997 61.276 47359 215.56 1722525 64.62 53329 66.931 57903 221.11 1874107 71.12 66661 Eon et al. 1971 72.629 70109 226.67 2039470 76.66 79993 isoteniscope-manometer 78.370 84525 232.22 2211722 81.51 93326 t/°C P/Pa 84.155 101325 237.78 2397755 82.41 95992 243.33 2590678 83.30 98659 60.3 44930 mp/°C –38.1 248.89 2797381 84.16 101325 70.3 64795 bp/°C 84.16 254.44 3010974 80.3 91459 260.00 3238347 bp/°C 84.16 90.3 126790 eq. 2 P/mmHg 265.56 3472610 100.3 172519 A 6.95926 271.11 3727544 eq. 2 P/mmHg B 1246.038 276.67 3996258 A 6.95926 .HV/(kJ mol–1) =34.77 C 221.354 282.22 4251192 B 1246.02 287.78 4540576 C 221.35 .HV/(kJ mol–1) = 293.33 4836850 at 45.36°C 33.61 298.89 5146905 .HV/(kJ mol–1) = at 63.08°C 32.67 304.44 5463849 at 25°C 34.60 at bp 31.47 at bp 31.47 FIGURE 16.1.8.11.1 Logarithm of vapor pressure versus reciprocal temperature for thiophene. Thiophene: vapor pressure vs. 1/T 0.0 1.0 2.0 3.0 4.0 5.0 6.0 7.0 8.0 0.0016 0.002 0.0024 0.0028 0.0032 0.0036 0.004 0.0044 1/(T/K) P( gol S ) aP/ Waddington et al. 1949 Kobe et al. 1956 Eon et al. 1971 Stull 1947 Zwolinski & Wilhoit 1971 m.p. = -38.21 °C b.p. = 84 °C © 2006 by Taylor & Francis Group, LLC Nitrogen and Sulfur Compounds 3419 16.1.8.12 Benzo[b]thiophene Common Name: Benzo[b]thiophene Synonym: thianaphthene, thionaphthene, 1-benzothiophene Chemical Name: CAS Registry No: 95-15-8 Molecular Formula: C8H6S Molecular Weight: 134.199 Melting Point (°C): 32 (Lide 2003) Boiling Point (°C): 221 (Lide 2003) Density (g/cm3 at 20°C): 1.1500 (Verschueren 1983) Molar Volume (cm3/mol): 139.7 (calculated-Le Bas method at normal boiling point) Enthalpy of Fusion, .Hfus (kJ/mol): Entropy of Fusion, .Sfus (J/mol K): Fugacity Ratio at 25°C (assuming .Sfus = 56 J/mol K), F: 0.854 (mp at 32°C) Water Solubility (g/m3 or mg/L at 25°C or as indicated): 130.0 (20°C, shake flask, Smith et al. 1978) 130.2 (Mill et al. 1981) 216* (59.05°C, equilibrium cell-GC, measured range 332.2–490.5 K, Leet et al. 1987) Vapor Pressure (Pa at 25°C or as indicated): 26.7 (20°C, estimated from naphthalene, Smith et al. 1978) 14.80 (calculated-bp, Mackay et al. 1982) log (P/mmHg) = –9.5352 – 2.6947 . 103/(T/K) + 8.8858·log (T/K) – 1.5478 . 10–2·(T/K) + 6.5159 . 10–6·(T/K)2; temp range 305–754 K (vapor pressure eq., Yaws 1994) Henry’s Law Constant (Pa·m3/mol at 25°C): 28.0 (calculated-P/C, Smith & Bomberger 1980) 24.1 (calculated-P/C, this work) Octanol/Water Partition Coefficient, log KOW: 3.09 (shake flask-UV, pH 7.4, Rogers & Cammarata 1969) 3.05 (HPLC-RT correlation, De Voogt et al. 1988) 3.12 (recommended, Sangster 1989, 1993) 3.26 (shake flask-HPLC, De Voogt et al. 1990) 3.18 (HPLC-RT correlation, Ritter et al. 1994) 3.17 (shake flask-dialysis tubing-HPLC/UV, both phases, Andersson & Schrader 1999) Octanol/Air Partition Coefficient, log KOA: Bioconcentration Factor, log BCF: 2.08 (mixed microbial populations, Steen & Karickhoff 1981) Sorption Partition Coefficient, log KOC: 1.77 (Coyote Creek sediment, Smith et al. 1978) 2.30 (lab. mixture of microorganisms, Smith et al. 1978) 3.49, 3.0 (soil, quoted, calculated-MCI . and fragment contribution, Meylan et al. 1992) S © 2006 by Taylor & Francis Group, LLC 3420 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals Environmental Fate Rate Constants, k, or Half-Lives, t.: Volatilization: estimated t. = 45 h in river, t. = 230 h in eutrophic pond, t. = 180 hours in eutrophic lake and oligotrophic lake by the one compartment model (Smith et al. 1978). Photolysis: rate constant of transformation and transport of (6.9 ± 0.7) . 10–7 s–1 exposed to 12 h sunlight per day in late May with estimated t. = 1200 h in river, t. = 2900 h in eutrophic pond, t. = 3500 h in eutrophic lake and t. = 600 h in oligotrophic lake by the one compartment model (Smith et al. 1978). Oxidation: laboratory investigated k = 83 M–1 s–1 for the reaction with RO2 radical and estimated t. = 105 h in river, eutrophic pond, eutrophic lake and oligotrophic lake by the one compartment model (Smith et al. 1978) k = 5.7 . 10–6 s–1 with t. = 34 h under natural sunlight conditions, k = 83 M–1 s–1 with t. = 96 d for freeradical oxidation in air-saturated water (NRCC 1983) Hydrolysis: Biodegradation: estimated t. > 20 h in river, t. < 20 h in eutrophic pond, t. = 20 h in eutrophic lake and very long half-life in oligotrophic lake, based on the biodegradation rate in the presence of alternative carbon sources will be one-half the biodegradation rate of quinoline when quinoline is the only carbon source by the one compartment model (Smith et al. 1978). Biotransformation: Bioconcentration, Uptake (k1) and Elimination (k2) Rate Constants: Half-Lives in the Environment: Surface water: estimated volatilization t. = 45 h in river, t. = 230 h in eutrophic pond, t. = 180 h in eutrophic lake and oligotrophic lake by the one compartment model (Smith et al. 1978); photolysis rate constant of transformation and transport of (6.9 ± 0.7) . 10–7 s–1 exposed to 12 h sunlight per day in late May with estimated photolysis t. = 1200 h in river, t. = 2900 h in eutrophic pond, t. = 3500 h in eutrophic lake and t. = 600 h in oligotrophic lake by the one compartment model (Smith et al. 1978). © 2006 by Taylor & Francis Group, LLC Nitrogen and Sulfur Compounds 3421 16.1.8.13 Dibenzothiophene Common Name: Dibenzothiophene Synonym: Chemical Name: dibenzothiophene CAS Registry No: 132-65-0 Molecular Formula: C12H8S Molecular Weight: 184.257 Melting Point (°C): 98.2 (Lide 2003) Boiling Point (°C): 332.5 (Lide 2003) Density (g/cm3 at 20°C): Molar Volume (cm3/mol): 191.3 (calculated-Le Bas method at normal boiling point) Entropy of Fusion, .Sfus (J/mol K): Fugacity Ratio at 25°C (assuming .Sfus = 56 J/mol K), F: 0.191 (mp at 98.2°C) Water Solubility (g/m3 or mg/L at 25°C or as indicated): 1.11 ± 0.09 (28°C, measured, Smith et al. 1978) 1.470 (24°C, shake flask-LSC, Means et al. 1980) 1.106 (Mill et al. 1981) 1.500 (Steen & Karickhoff 1981) 1.032 (literature average, Pearlman et al. 1984) Vapor Pressure (Pa at 25°C or as indicated and reported temperature dependence equations): 0.267 (20°C, estimated, Aubry et al. 1975) log (P/mmHg) = 22.90 – 10910/(T/K), temp range 60–00°C (solid, gas saturation, Edward & Prausnitz 1981) log (P/mmHg) = 21.10 – 8353/(T/K), temp range 100–130°C (liquid, gas saturation, Edward & Prausnitz 1981) 0.263, 0.0083 (20°C, quoted, calculated-bp, Mackay et al. 1982) 0.893 (static apparatus-extrapolated from Chebyshev polynomials, Sivaraman & Kobayashi 1982) 0.586 (extrapolated-Cox eq., Chao et al. 1983) log (P/atm) = [1– 605.160/(T/K)] . 10^{0.865373 – 5.51221 . 10–4 ± (T/K) + 6.05701 . 10–7 ± (T/K)2}; temp range: 424.81–607.53 K (Cox eq., Chao et al. 1983) log (PL/kPa) = 7.18577 – 3140.15/(T/K), temp range 385–574 K (Antoine eq., Stephenson & Malanowski 1987) Henry’s Law Constant (Pa·m3/mol at 25°C): 44.3 (calculated-P/C, Smith & Bomberger 1980) Octanol/Water Partition Coefficient, log KOW: 4.38 (shake flask-LSC, Means et al. 1980) 4.33 (HPLC-RT correlation, De Voogt et al. 1988) 4.38 (recommended, Sangster 1989, 1993) 4.49 (shake flask-HPLC, De Voogt et al. 1990) 4.38 (recommended, Hansch et al. 1995) 4.41 ± 0.19, 4.43 ± 0.61 (HPLC-k. correlation: ODS-65 column, Diol-35 column, Helweg et al. 1997) 4.36 (shake flask-dialysis tubing-HPLC/UV, both phases, Andersson & Schrader 1999) Octanol/Air Partition Coefficient, log KOA: S © 2006 by Taylor & Francis Group, LLC 3422 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals Bioconcentration Factor, log BCF: 3.20 (mixed microbial populations, Steen & Karickhoff 1981) Sorption Partition Coefficient, log KOC: 3.14 (Coyote Creek sediment, Smith et al. 1978) 4.05 (soil, Hassett et al. 1980) 4.05 (average of 3 sediment/soil samples, equilibrium sorption isotherm, Means et al. 1980) 4.00 (soil, calculated-MCI ., Sabljic 1987) 4.00 (soil, calculated-MCI ., Sabljic 1987) 4.17 (soil, calculated-KOW, model of Karickhoff et al. 1979, Sabljic 1987) 3.75 (soil, calculated-KOW, model of Kenaga & Goring 1980, Sabljic 1987) 2.92 (soil, calculated-KOW, model of Briggs 1981, Sabljic 1987) 4.00 (soil, calculated-KOW, model of Means et al. 1982, Sabljic 1987) 3.60 (soil, calculated-KOW, model of Chiou et al. 1983, Sabljic 1987) 4.59 (humic acid, HPLC-k. correlation, Nielsen et al. 1997) 3.87 (soil: organic carbon OC . 0.1%, average, Delle Site 2001) 4.02, 4.04 (sediments: organic carbon OC . 0.1%, OC . 0.5%, average, Delle Site 2001) 4.07 (Askov soil, a Danish agricultural soil, Sverdrup et al. 2002) Environmental Fate Rate Constants, k, or Half-Lives, t.: Volatilization: estimated t. = 140 h in river, t. = 720 h in eutrophic pond, t. = 580 h in eutrophic lake and oligotrophic lake by the one compartment model (Smith et al. 1978). Photolysis: solar photolysis k = 1.5 . 10–8 s–1 over 24-h day; rate constant of transformation and transport of (2.04 ± 0.08) . 10–6 s–1 exposed to 12 h sunlight per day in early March with estimated t. = 380 h in river, t. = 950 h in eutrophic pond and eutrophic lake and t. = 190 h in oligotrophic lake from average photolysis rates on a summer day at 40°N latitude by the one compartment model (Smith et al. 1978); t. = 4–8 h for disappearance via direct photolysis in aquatic media (Harris 1982). Oxidation: laboratory investigated k < 7.5 M–1 s–1 for the reaction with RO2 radical and estimated t. > 105 h in river, eutrophic pond, eutrophic lake and oligotrophic lake by the one compartment model (Smith et al. 1978). k = 1.5 . 10–6 s–1 with t. = 128 h under natural sunlight conditions, k < 7.5 M–1 s–1 with t. > 3.5 yr for free-radical oxidation in air-saturated water (NRCC 1983) Hydrolysis: Biodegradation: k = 5.3 . 10–7 mL cell–1 h–1 and the estimated t. = 13 h in river, eutrophic pond, and eutrophic lake and t. > 104 h in oligotrophic lake by the one compartment model (Smith et al. 1978) Biotransformation: Bioconcentration, Uptake (k1) and Elimination (k2) Rate Constants: Half-Lives in the Environment: Surface water: t. = 0.5 h from river water, t. = 13 h from pond water, t. = 13 h from eutrophic lake and t. = 140 h from oligotrophic lake predicted by one-compartment model for all processes; estimated volatilization t. = 140 h in river, t. = 720 h in eutrophic pond, t. = 580 h in eutrophic lake and oligotrophic lake; photolysis rate constant of transformation and transport k = (2.04 ± 0.08) . 10–6 s–1 exposed to 12 h sunlight per day in early March with estimated photolysis t. = 380 h in river, 950 h in eutrophic pond and eutrophic lake and t. = 190 h in oligotrophic lake; biodegradation t. = 13 h in river, eutrophic pond water and t. = 140 h in oligotrophic lake (Smith et al. 1978); t. = 4–8 h for disappearance via direct photolysis in aqueous media (Harris 1982). © 2006 by Taylor & Francis Group, LLC Nitrogen and Sulfur Compounds 3423 16.1.8.14 Thiourea Common Name: Thiourea Synonym: thiocarbamide Chemical Name: thiourea CAS Registry No: 62-56-6 Molecular Formula: CH4N2S, H2NCSNH2 Molecular Weight: 76.121 Melting Point (°C): 178 (Lide 2003) Boiling Point (°C): decomposes (Verschueren 1983) Density (g/cm3 at 20°C): 1.045 (Weast 1982–83; Verschueren 1983, Dean 1992) Dissociation Constant, pK: 2.03 (pK1, Dean 1985) Molar Volume (cm3/mol): 76.2 (calculated-Le Bas method at normal boiling point) Enthalpy of Fusion, .Hfus (kJ/mol): 14.42 (Donnelly et al. 1990) 12.55 (Kim et al. 1994) 15.64, 14.92, 15.17 (differential scanning calorimetry in three types of crucibles, Gatta et al. 2000) Entropy of Fusion, .Sfus (J/mol K): 35.2, 33.7, 34.1 (Gatta et al. 2000) Fugacity Ratio at 25°C (assuming .Sfus = 56 J/mol K), F: 0.0315 (mp at 178°C) Water Solubility (g/m3 or mg/L at 25°C or as indicated): 91000 (20–25°C, shake flask-gravimetric, Dehn 1917) 91800 (13°C, Verschueren 1983) 89800 (Windholz 1983) 110000 (Budavari 1989) 90000 (Dean 1985) Vapor Pressure (Pa at 25°C): Henry’s Law Constant (Pa m3/mol at 25°C): Octanol/Water Partition Coefficient, log KOW: –1.02 (Leo et al. 1971) –0.95 (shake flask, Cornford 1982) –2.38, –0.95 (calculated, Verschueren 1983) –1.17 (shake flask, OECD 1981 Guidelines, Geyer et al. 1984) –1.08, –1.03 (pH 6.5, pH 12, shake flask-HPLC, Govers et al. 1986) –1.14, –1.02 (shake flask, Log P Database, Hansch & Loe 1987) –0.99 (recommended, Sangster 1993) –1.02 (recommended, Hansch et al. 1995) Octanol/Air Partition Coefficient, log KOA: Bioconcentration Factor, log BCF: 1.73 (alga chlorella fusca, wet wt. basis, Geyer et al. 1984) –0.699 (alga chlorella fusca, calculated-KOW, Geyer et al. 1984) S H2N NH2 © 2006 by Taylor & Francis Group, LLC 3424 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals Sorption Partition Coefficient, log KOC: Environmental Fate Rate Constants, k, and Half-Lives, t.: Volatilization: Photolysis: Oxidation: photooxidation t. = 1.6–16 h in air, based on rate constant for the vapor-phase reaction with OH radical and photooxidation t. = 2048–81927 h in water, based on estimated rate data for reaction with OH radical in aqueous solution (Howard et al. 1991). Hydrolysis: Biodegradation: aqueous aerobic biodegradation t. = 24–168 h, based on aqueous aerobic screening test data and aqueous anaerobic biodegradation t. = 96–672 h, based on aqueous aerobic degradation half-life (Howard et al. 1991). Biotransformation: Bioconcentration Uptake (k1) and Elimination (k2) Rate Constants: Half-Lives in the Environmental Compartments: Air: t. = 1.6–16 h, based on estimated photooxidation half-life in air (Howard et al. 1991). Surface water: t. = 24–168 h, based on estimated aqueous aerobic biodegradation half-life (Howard et al. 1991). Ground water: t. = 48–336 h, based on estimated unacclimated aqueous aerobic biodegradation half-life (Howard et al. 1991). Sediment: Soil: t. = 24–168 h, based on estimated aqueous aerobic biodegradation half-life (Howard et al. 1991) Biota: © 2006 by Taylor & Francis Group, LLC Nitrogen and Sulfur Compounds 3425 16.1.8.15 Thioacetamide Common Name: Thioacetamide Synonym: ethanethioamide, acetothioamide Chemical Name: thioacetamide CAS Registry No: 62-55-5 Molecular Formula: C2H5NS, CH3CSNH2 Molecular Weight: 75.133 Melting Point (°C): 115.5 (Lide 2003) Boiling Point (°C): Density (g/cm3 at 20°C): Molar Volume (cm3/mol): 84.2 (calculated-Le Bas method at normal boiling point) Dissociation Constant pKa: Enthalpy of Fusion, .Hfus (kJ/mol): Entropy of Fusion, .Sfus (J/mol K): Fugacity Ratio at 25°C (assuming .Sfus = 56 J/mol K), F: 0.129 (mp at 115.5°C) Water Solubility (g/m3 or mg/L at 25°C): 163000 (Dean 1985) 163000 (Budavari 1989) Vapor Pressure (Pa at 25°C): Henry’s Law Constant (Pa·m3/mol at 25°C): Octanol/Water Partition Coefficient, log KOW: –0.46, 0 36 (Verschueren 1983) –0.26 (shake flask, Log P Database, Hansch & Leo 1987) –0.26 (recommended, Sangster 1993) –0.26 (recommended, Hansch & Leo 1995) Octanol/Air Partition Coefficient, log KOA: Bioconcentration Factor, log BCF: Sorption Partition Coefficient, log KOC: Environmental Fate Rate Constants, k, or Half-Lives, t.: Volatilization: Photolysis: Oxidation: atmospheric t. = 3.2–31.7 h, based on estimated rate data for OH radical in air (Howard et al. 1991). Hydrolysis: first-order rate constant k = 8.6 . 10–1 h–1 at pH 7 and 25°C (Ellington et al. 1987), corresponding to a t. = 8064 h (Howard et al. 1991); acid rate constant k = 6.0 . 10–2 M–1 ± h–1, corresponding to a t. = 333 d and base rate constant k = 1.4 M–1 ± h–1, corresponding to a t. = 289 d (Howard et al. 1991). Biodegradation: aerobic biodegradation t. = 24–168 h, based on aqueous aerobic screening test data and anaerobic biodegradation t. = 96–672 h, based on estimated aqueous aerobic biodegradation half-life (Howard et al. 1991). Biotransformation: Bioconcentration, Uptake (k1) and Elimination (k2) Rate Constants: S NH2 © 2006 by Taylor & Francis Group, LLC 3426 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals Half-Lives in the Environment: Air: t. = 3.2–31.7 h, based on estimated photooxidation half-life in air (Howard et al. 1991). Surface water: t. = 24–268 h, based on estimated aqueous aerobic biodegradation half-life (Howard et al. 1991). Groundwater: t. = 48–336 h, based on estimated unacclimated aqueous aerobic biodegradation half-life (Howard et al. 1991). Sediment: Soil: t. = 24–168 h, based on estimated aqueous aerobic biodegradation half-life (Howard et al. 1991). Biota: © 2006 by Taylor & Francis Group, LLC Nitrogen and Sulfur Compounds 3427 16.2 SUMMARY TABLES TABLE 16.2.1 Summary of physical properties of nitrogen and sulfur containing compounds Compound CAS no. Molecular formula Molecular weight, MW g/mol m.p. °C b.p. °C Fugacity ratio, F at 25°C* Molar volume, VM cm3/mol pKa or pKb MW/ . at 20°C Le Bas Nitriles: Acetonitrile 75-05-8 CH3CN 41.052 –43.82 81.65 1 52.25 56.3 Propionitrile 107-12-0 C2H5CN 55.079 –92.78 97.14 1 70.45 78.5 Butyronitrile 109-74-0 C3H7CN 69.106 –111.9 117.6 1 87.35 100.7 Acrylonitrile (2-Propenitrile) 107-13-1 C2H3CN 53.063 –83.48 77.3 1 65.83 71.1 Benzonitrile 100-47-0 C6H5CN 103.122 –13.99 191.1 1 107.9 Adiponitrile 111-69-3 CN(CH2)4CN 108.141 1 295 1 149.6 Aliphatic amines: Methylamine 74-89-5 CH3NH2 31.058 –93.5 –6.32 1 43.8 Dimethylamine 124-40-3 (CH3)2NH 45.084 –92.18 6.88 1 68.77 67.5 10.77 Trimethylamine 75-50-3 (CH3)3N 59.110 –117.1 2.87 1 93.00 93.3 9.8 Ethylamine 75-04-7 CH3CH2NH2 45.084 –80.5 16.5 1 66.02 66.0 10.63 Diethylamine 109-89-7 (C2H5)2NH 73.137 –49.8 55.5 1 103.45 111.9 10.8 Triethylamine 121-44-8 (C2H5)3N 101.910 –114.7 89 1 154.8 10.78 n-Propylamine 107-10-8 C3H7NH2 59.110 –84.75 47.22 1 82.41 88.2 10.568 Dipropylamine 142-84-7 (C3H7)2NH 101.190 –63 109.3 1 Diisopropylamine 108-18-9 i(C3H7)2NH 101.190 –61 83.9 1 Tripropylamine 102-69-2 (C3H7)3N 143.270 –93.5 156 1 10.66 n-Butylamine 109-73-9 C4H9NH2 73.137 –49.1 77.0 1 98.94 110.4 10.64 Isobutylamine 78-81-9 iC4H9NH2 73.137 –86.7 67.75 1 110.4 10.41 tert-Butylamine 75-64-9 (CH3)3CNH2 73.137 –66.94 44.04 1 110.4 1.685 Di-n-butylamine 111-92-2 (C4H9)2NH 129.244 –62 159.6 1 199.2 11.25 Tributylamine 102-82-9 (C4H9)3N 185.349 –70 216.5 1 288 9.93 Ethylenediamine 107-15-3 H2NCH2CH2NH2 60.098 11.14 117 1 Ethanolamine 141-43-5 HOCH2CH2NH2 61.098 10.5 171 1 60.21 73.4 9.48 Diethanolamine 111-42-2 (HOCH2CH2)2NH 105.136 28 268.8 0.934 95.87 126.7 8.88 Triethanolamine 102-71-6 (HOCH2CH2)3N 149.188 20.5 335.4 1 132.71 182.1 7.76 Cyclohexylamine 108-91-8 C6H12NH 99.174 –17.8 134 1 117.4 10.66 (Continued) © 2006 by Taylor & Francis Group, LLC 3428 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals TABLE 16.2.1 (Continued) Compound CAS no. Molecular formula Molecular weight, MW g/mol m.p. °C b.p. °C Fugacity ratio, F at 25°C* Molar volume, VM cm3/mol pKa or pKb MW/ . at 20°C Le Bas Aromatic amines: Aniline 62-53-3 C6H5NH2 93.127 –6.02 184.17 1 91.15 110.2 4.596 2-Chloroaniline 95-51-2 Cl(C6H4)NH2 127.572 –1.9 208.8 1 105.21 131.1 2.661 3-Chloroaniline 108-42-9 Cl(C6H4)NH2 127.572 –10.28 230.5 1 104.91 131.1 3.5 4-Chloroaniline 106-47-8 Cl(C6H4)NH2 127.572 70.5 232 0.358 131.1 3.982 3,4-Dichloroaniline 95-76-1 Cl2C6H3NH2 162.017 72 272 0.346 152.0 2,4,6-Trichloroaniline 634-93-5 C6H4Cl3N 196.462 78.5 262 0.299 172.9 o-Toluidine 95-53-4 CH3C6H4NH2 107.153 –14.41 200.3 1 107.32 132.4 4.45 m-Toluidine 108-44-1 CH3C6H4NH2 107.153 –31.3 203.3 1 108.36 132.4 4.71 p-Toluidine 106-49-0 CH3C6H4NH2 107.153 43.6 200.4 0.657 111.40 132.4 5.08 N,N.-Dimethylaniline 121-69-7 C6H5N(CH3)2 121.180 2.42 194.15 1 126.80 154.6 5.15 2,4-Xylidine 95-68-1 (CH3)2C6H3NH2 121.180 –14.3 214 1 154.6 4.89 2,5-Xylidine 95-78-3 (CH3)2C6H3NH2 121.180 15.5 214 1 154.6 4.54 2,6-Xylidine 87-62-7 (CH3)2C6H3NH2 121.180 11.2 215 1 123.12 154.6 3.95 2-Ethylaniline 578-54-1 C2H5C6H4NH2 121.180 –43 209.5 1 139.6 4.42 3-Ethylaniline 587-02-0 C2H5C6H4NH2 121.180 –64 214 1 139.6 4.70 4-Ethylaniline 589-16-2 C2H5C6H4NH2 121.180 –2.4 217.5 1 139.6 5.00 N,N.-Diethylaniline 91-66-7 C6H5N(C2H5)2 149.233 –38.8 216.3 1 199.0 6.56 Diphenylamine 122-39-4 (C6H5)2NH 169.222 53.2 302 0.529 145.88 200.3 0.90 4-Aminobiphenyl 92-67-1 C6H5C6H4NH2 169.222 53.5 302 0.525 168.8 4.27 Benzidine 92-87-5 NH2(C6H4)2NH2 184.236 120 401 0.117 213.0 4.66 3,3.-Dichlorobenzidine 91-94-1 C12H10Cl2N2 253.126 132.5 0.0882 254.8 11.7 .-Naphthylamine 134-32-7 C10H7NH2 143.185 49.2 300.7 0.579 161.8 3.92 .-Naphthylamine 91-59-8 C10H7NH2 143.185 113 306.2 0.137 161.8 4.15 N,N.-Bianiline 122-66-7 (C6H5)2(NH)2 184.236 131 0.0912 213.0 13.2 2-Nitroaniline 88-74-4 C6H6N2O2 138.124 71.0 284 0.354 138.7 –0.28 3-Nitroaniline 99-09-2 C6H6N2O2 138.124 113.4 306 dec 0.136 138.7 2.46 4-Nitroaniline 100-01-6 C6H6N2O2 138.124 147.5 332 0.0628 97.00 138.7 1.01 2,4-Dinitroaniline 97-02-9 (O2N)2C6H3NH2 183.122 180.0 0.0301 167.2 –4.25 2,6-Dinitroaniline 606-22-4 (O2N)2C6H3NH2 183.122 141 0.0728 167.2 –5.23 3,5-Dinitroaniline 618-87-1 (O2N)2C6H3NH2 183.122 163 0.0443 167.2 0.229 © 2006 by Taylor & Francis Group, LLC Nitrogen and Sulfur Compounds 3429 Nitroaromatic compounds: Nitrobenzene 98-95-3 C6H5NO2 123.110 5.7 210.8 1 102.28 112.0 1,2-Dinitrobenzene 528-29-0 C6H4(NO2)2 168.107 116.5 318 0.127 149.4 1,3-Dinitrobenzene 99-65-0 C6H4(NO2)2 168.107 90.3 291 0.229 149.4 1,4-Dinitrobenzene 100-25-4 C6H4(NO2)2 168.107 173.5 297 0.0349 149.4 2-Nitrotoluene 88-72-2 CH3C6H4NO2 137.137 –10.4 222 1 117.93 153.0 3-Nitrotoluene 99-08-1 CH3C6H4NO2 137.137 15.5 232 1 153.0 4-Nitrotoluene 99-99-0 CH3C6H4NO2 137.137 51.63 238.3 0.548 153.0 2,4-Dinitrotoluene (DNT) 121-14-2 CH3C6H3(NO2)2 182.134 70.5 300 dec 0.358 175.2 2,6-Dinitrotoluene 606-20-2 CH3C6H3(NO2)2 182.134 66.0 285 0.396 175.2 2,4,6-Trinitrotoluene (TNT) 118-96-7 CH3C6H2(NO2)3 227.131 80.5 240 exp 0.285 137.32 203.7 1-Nitronaphthalene 86-57-7 C10H7NO2 173.169 61 304 0.443 176.1 2-Nitronaphthalene 581-89-5 C10H7NO2 173.169 79 314 0.295 176.1 4-Nitrobiphenyl 92-93-3 C12H9NO2 199.205 114 340 0.134 211.3 5-Nitro-acenaphthene 602-87-9 C12H9NO2 199.205 103 0.172 211.3 Amide and ureas: Acetamide 60–35-5 CH3CONH2 59.067 80.16 222 0.288 66.9 7.62 Acrylamide 79-06-1 H2C=CHCONH2 71.078 84.5 192.5 0.261 80.8 Benzamide 55-21-0 C6H5CONH2 121.137 127.3 290 0.0992 132.4 Urea 57-13-6 H2NCONH2 60.055 133 dec 0.0872 45.39 58.0 Nitrosoamines: N-Nitrosodimethylamine 62-75-9 (CH3)2NNO 74.081 152 87.7 N-Nitrosodiethylamine 55-18-5 (C2H5)2NNO 120.134 176.9 130.6 Di-n-propyl nitrosamine 621-64-7 (C3H7)2NNO 130.187 206 176.5 Diphenylnitrosamine 86-30-6 (C6H5)2NNO 198.219 66.5 152 0.392 220.5 Heterocyclic compounds: 1H-Pyrrole 109-97-7 C4H5N 67.090 –23.39 129.79 1 69.18 78.2 1-Methylpyrrole 96-54-8 C5H7N 81.117 –56.32 112.81 1 104.0 Pyrrolidine 123-75-1 C4H8NH 71.121 –57.79 86.56 1 96.6 4.453 Imidazole 288-32-4 C3H4N2 68.077 89.5 257 0.233 78.9 11.305 Indazole 271-44-3 C7H6N2 118.136 148 269 0.0621 130.5 Indole 120-72-9 C8H7N 117.149 52.5 253.6 0.537 133.4 Indoline 496-15-1 C8H9N 119.164 229 140.8 Pyridine 110-86-1 C5H5N 79.101 –41.70 115.23 1 80.56 93.0 5.17 2-Methylpyridine 109-06-8 C6H7N 93.127 –66.68 129.38 1 98.61 115.2 5.96 3-Methylpyridine 108-99-6 C6H7N 93.127 –18.14 144.14 1 97.35 115.2 5.68 4-Methylpyridine 108-89-4 C6H7N 93.127 3.67 145.36 1 115.2 6.00 (Continued) © 2006 by Taylor & Francis Group, LLC 3430 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals TABLE 16.2.1 (Continued) Compound CAS no. Molecular formula Molecular weight, MW g/mol m.p. °C b.p. °C Fugacity ratio, F at 25°C* Molar volume, VM cm3/mol pKa or pKb MW/ . at 20°C Le Bas 2,3-Dimethylpyridine 583-61-9 C7H9N 107.153 –15.5 161.12 1 135.9 6.6 2,4-Dimethylpyridine 108-47-4 C6H9N 107.153 –64 158.38 1 135.9 2,6-Dimethylpyridine 108-48-5 C7H9N 107.153 –6.1 144.01 1 135.9 6.72 2,4,6-Trimethylpyridine 108-75-8 C8H11N 121.180 -46 170.6 1 158.1 7.43 Quinolines: Quinoline 91-22-5 C9H7N 129.159 –14.78 237.16 1 144.7 4.90 Isoquinoline 119-65-3 C9H7N 129.159 26.47 243.22 0.967 144.7 5.4 3-Methyl-isoquinoline 1125-80-0 C10H9N 143.185 68 249 0.379 166.9 2,7-Dimethylquinoline 93-37-8 C11H11N 157.212 61 264.5 0.443 189.1 Benzo[f]quinoline 85-02-9 C13H9N 179.217 94 352 0.210 196.3 Benzo(h)quinoline 230-27-3 C13H9N 179.217 52 339 0.543 196.3 9H-Carbazole 86-74-8 C6H4NHC6H4 167.206 246.3 354.69 0.00674 192.9 7H-Dibenzo[c,g]carbazole 194-59-2 (C10H6)2NH 267.324 158 0.0496 296.1 Acridine 260-94-6 C13H9N 179.217 110 344.86 0.147 196.3 5.60 Benz[a]acridine 225-11-6 C17H11N 229.276 244.8 Benz[c]acridine 225-51-4 C17H11N 229.276 132 0.0892 244.8 Dibenz[a,h]acridine 53–70–3 C22H14 278.346 269.5 524 0.00399 300.0 Sulfur compounds: Carbon disulfide 75-15-0 CS2 76.141 –112.1 46 1 60.28 66.0 Dimethyl sulfate 77-78-1 (CH3O)2SO2 126.132 –27 188 dec 1 109.7 Diethyl sulfate 64-67-5 (C2H5O)2SO2 154.185 –24 208 1 138.4 Dimethyl sulfite 616-42-2 (CH3O)2SO 110.132 126 100.5 Dimethyl sulfoxide (DMSO) 67-68-5 (CH3)2SO 78.133 17.89 189 1 85.7 Dimethyl sulfone 67-71-0 (CH3)2SO2 94.133 108.9 238 0.150 94.0 Dimethyl sulfide 75-18-3 (CH3)2S 62.134 –98.24 37.33 1 73.77 77.4 Dimethyl disulfide 624-92-0 C2H6S2 94.199 –84.67 109.74 1 58.78 103.0 Diethyl sulfide 352-93-2 C4H10S 90.187 –103.91 92.1 1 128.1 Diethyl disulfide 110-81-6 C4H10S2 122.252 –101.5 154.0 1 147.4 Thiols: Methanethiol 74-93-1 CH3SH 48.108 –123 5.9 1 55.52 55.2 10.7 Ethanethiol 75-08-1 C2H5SH 62.134 –147.88 35.0 1 74.05 77.4 10.61 Propanethiol 107-03-9 C3H7SH 76.161 –113.13 67.8 1 90.55 99.6 1-Butanethiol (Butyl mercaptan) 109-79-5 CH3(CH2)3SH 90.187 –115.7 98.5 1 107.16 121.8 © 2006 by Taylor & Francis Group, LLC Nitrogen and Sulfur Compounds 3431 2-Butanethiol 513-53-1 C4H7SH 90.187 –165 85.0 1 121.8 Benzenethiol 108-98-5 C6H5SH 110.177 -14.93 169.1 1 102.34 106.8 6.5 2-Methylbenzenethiol 137-06-4 C7H8S 124.204 15 195 1 129.0 3-Methylbenzenethiol 108-40-7 C7H8S 124.204 –20 195 1 129.0 4-Methylbenzenethiol 106-45-6 C7H8S 124.204 43 195 0.666 129.0 Thiophenes: Thioazole 288-47-1 C3H3NS 85.128 –33.62 118 1 85.2 Thiophene 110-02-1 C4H4S 84.140 –38.21 84.0 1 79.02 88.1 2-Methylthiophene 554-14-3 C5H6S 98.167 –63.4 112.6 1 110.3 3-Methylthiophene 616-44-4 C5H6S 98.167 –69 115.5 1 110.3 Benzo[b]thiophene 95-15-8 C8H6S 134.199 32 221 0.854 139.7 Dibenzothiophene 132-65-0 C12H8S 184.257 98.2 332.5 0.191 191.3 Thianthrene 92-85-3 (C6H4)2S2 216.322 159.3 365 0.0481 210.9 Thiobenzamide 2227-79-4 C6H5CSNH2 137.203 117 0.125 135.8 Thiourea 62-56-6 H2NCSNH2 76.121 178 0.0315 72.84 76.2 2.03 Thioacetamide 62-55-5 CH3CSNH2 75.133 115.5 0.129 84.2 * Assuming .Sfus = 56 J/mol K © 2006 by Taylor & Francis Group, LLC 3432 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals TABLE 16.2.2 Summary of selected physical-chemical properties of nitrogen and sulfur containing compounds at 25°C. Compound Selected properties Henry’s law constant Vapor pressure Solubility H/(Pa·m3/mol) PS/Pa PL/Pa S/(g/m3) CS/(mol/m3) CL/(mol/m3) log KOW calcd P/C exptl Nitriles: Acetonitrile 11840 11840 miscible –0.34 2.75 Propionitrile 5950 5950 103000 1870.0 1870.0 0.16 3.182 3.8 Butyronitrile 2546 2546 33000 477.5 477.5 5.263 Benzonitrile 100 100 2000 19.39 19.39 1.55 5.156 Acrylonitrile (2-Propenitrile) 11000 11000 75500 1423 1423 0.25 7.731 11.14 Adiponitrile 0.3066 0.3066 8000 73.96 73.96 –0.32 0.0041 Aliphatic amines: Methylamine 357300 357300 miscible –0.57 1.125 Dimethylamine 206200 206200 miscible –0.38 1.8 Trimethylamine 219300 219300 miscible 0.27 6.67 Ethylamine 141650 141650 miscible –0.13 1.012 Diethylamine 31490 31490 miscible 0.43 2.60 Triethylamine 7610 7610 55000 540 540 1.64 14.099 n-Propylamine 40740 40740 miscible 0.48 1.274 Dipropylamine 53000 520 520 Diisopropylamine 12390 122 Tripropylamine 220 1.536 1.54 2.79 n-Butylamine 13650 13650 miscible 0.97 1.526 Isobutylamine 18760 18760 miscible 0.73 t-Butylamine 48260 48260 miscible 0.4 Di-n-butylamine 304 304 4700 36.37 36.37 2.83 8.359 Tributylamine 5330 5330 40 0.216 0.216 2.47 . 104 Ethanolamine 34.66 34.66 miscible –1.31 Diethanolamine 0.0373 0.0399 miscible –1.43 Triethanolamine 4.79 . 10–4 4.79 . 10–4 miscible –1.59 Cyclohexylamine 1173 1173 miscible 1.49 Diphenylamine 0.0612 0.115 300 1.773 3.338 3.45 0.035 .-Naphthylamine 0.254 0.45 2.23 .-Naphthylamine 0.035 0.248 6.4 0.045 0.317 2.34 4-Aminobiphenyl 2.83 © 2006 by Taylor & Francis Group, LLC Nitrogen and Sulfur Compounds 3433 Aromatic amines: Aniline 65.19 65.19 36070 387.4 387.35 0.90 0.168 12.16 2-Chloroaniline 22.66 22.66 3800 29.79 29.79 1.90 0.761 3-Chloroaniline 9.53 9.530 5440 42.64 42.64 1.88 0.223 4-Chloroaniline 2.33 6.873 3000 23.52 69.37 1.83 0.099 3,4-Dichloroaniline 1.3 3.746 92.05 0.568 1.637 2.67 2.289 2,4,6-Trichloroaniline 0.00626 0.021 3.694 o-Toluidine 13.3 13.30 15000 139.98 139.98 0.095 m-Toluidine 36 36.0 15030 140.26 140.26 1.44 0.257 p-Toluidine 45 61.48 7350 68.59 93.70 1.4 0.656 N,N.-Dimethylaniline 107 107.0 1105 9.119 9.119 2.31 11.734 2,4-Xylidine 20.5 20.50 5900 48.69 48.69 0.421 2,5-Xylidine 5000 41.26 41.26 2,6-Xylidine 670 670.0 4700 38.79 38.79 1.94 17.275 2-Ethylaniline 7500 61.89 61.89 1.93 4-Ethylaniline 13.5 13.50 5100 42.09 42.09 1.96 0.321 N,N.-Diethylaniline 9.7 9.70 670 4.49 4.49 2.161 Benzidine 1.0 . 10–6 1.06 . 10–5 400 2.17 23.1 1.81 4.61 . 10–7 3,3.-Dichlorobenzidine 5.6 . 10–5 6.41 . 10–4 3.1 0.0122 0.140 3.51 0.005 N,N.-Bianiline 0.0035 0.252 0.0014 0.0154 3.82 3.45 . 10–4 2-Nitroaniline 0.62 1.851 1200 8.687 25.93 1.78 4-Nitroaniline 0.035 0.589 800 5.792 97.50 1.31 2,4-Dinitroaniline 4.1 Nitroaromatic compounds: Nitrobenzene 20 20.0 1900 15.43 15.43 1.85 1.296 1,2-Dinitrobenzene 0.0052 0.0433 1,3-Dinitrobenzene 0.0081 0.0348 546 3.25 13.94 1.49 0.002 1,4-Dinitrobenzene 13.3 386.63 442 2.63 76.43 2.37 5.059 2-Nitrotoluene 17.9 17.90 651.42 4.75 4.75 2.30 3.768 3-Nitrotoluene 27.2 27.20 499.19 3.64 3.64 2.45 7.473 4-Nitrotoluene 0.653 1.2004 254.4 1.86 3.41 2.37 0.352 2,4-Dinitrotoluene (DNT) 0.133 0.3705 270 1.48 4.13 2.01 0.090 2,6-Dinitrotoluene 0.0767 0.1952 200 1.72 0.070 2,4,6-Trinitrotoluene (TNT) 0.00107 0.0038 210 0.925 3.29 1-Nitronaphthalene 0.702 0.0312 0.072 9.82 0.057 0.132 3.19 3.50 2-Nitronaphthalene 9.24 0.053 0.183 4-Nitrobiphenyl 1.231 6.18 . 10–3 0.045 3.78 5-Nitro-acenaphthene 0.91 4.57 . 10–3 0.026 (Continued) © 2006 by Taylor & Francis Group, LLC 3434 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals TABLE 16.2.2 (Continued) Compound Selected properties Henry’s law constant Vapor pressure Solubility H/(Pa·m3/mol) PS/Pa PL/Pa S/(g/m3) CS/(mol/m3) CL/(mol/m3) log KOW calcd P/C exptl Amides: RCONH2 Acetamide (ethanamide) 2.44 8.3562 408000 6907.1 23650 –1.26 3.53 . 10–4 Acrylamide 0.415 1.5900 2050000 2884 11050 –0.9 1.44 . 10–4 Benzamide 0.00522 0.0544 14000 1692 17630 0.64 4.52 . 10–5 Urea: (NH2)2C=O Urea 0.0016 0.0186 1000000 16650 1.93x105 –2.11 9.61 . 10–8 Nitrosoamines: N-Nitrosodimethylamine miscible –0.57 3.343 Di-n-propyl nitrosamine 27 9900 76.04 1.31 0.355 Diphenyl nitrosamine 13.33 34.27 35.10 0.116 0.299 3.13 114.6 Heterocyclic compounds: 1H-Pyrrole 1100 1100 45000 670.7 670.7 0.75 1.640 1-Methylpyrrole 3312 Indazole 827 7.00 100.43 Indole 2.24 4.187 1874 16.00 29.90 2 0.140 Indoline 10800 90.63 Pyridine 2775 2775 miscible 0.65 0.895 2-Methylpyridine 1496 1496 miscible 1.11 1.01 3-Picoline 1333 1333 miscible 1.2–1.24 0.788 4-Picoline 757 757 miscible 1.22 0.601 2,3-Dimethylpyridine 426 104000 970.6 0.725 2,4-Dimethylpyridine 456 456 miscible 0.678 2,6-Dimethylpyridine 746 746 miscible 1.06 2,4,6-Trimethylpyridine 5170 5170 35700 294.6 294.6 17.549 Quinolines: Quinoline 1.21 1.21 6110 47.31 47.31 2.06 0.026 Isoquinoline 670 693 4521 35.00 36.20 2.08 19.141 2,7-Dimethylquinoline 1795 11.42 24.77 Benzo[f]quinoline 0.0067 76.1 0.42 2.02 3.20 0.0096 Benzo[h]quinoline 0.03 0.0555 9H-Carbazole 0.0933 14.976 1.03 0.006 0.989 3.80 15.146 7H-Dibenzo[c,g]carbazole 1.3 . 10–7 2.5 . 10–6 0.063 0.236 4.532 5.75 © 2006 by Taylor & Francis Group, LLC Nitrogen and Sulfur Compounds 3435 Acridine 0.0065 0.0451 38.5 0.215 1.492 3.4 0.030 Benz[a]acridine 4.45 Sulfur compounds: Carbon disulfide 48210 48210 2100 27.584 27.584 1747.75 Dimethyl sulfate 128 128 Diethyl sulfate 49.1 49.1 Dimethyl sulfoxide (DMSO) 80.0 80.0 253000 354.8 354.8 –1.35 0.225 Dimethyl sulfone 5.16 34.17 –1.41 200.83 Dimethyl sulfide 64650 64650 20000 321.9 7.72 Dimethyl disulfide 4000 4000 6300 66.88 66.88 59.81 Diethyl sulfide 7782 7782 1.95 Diethyl disulfide 689 689 Thiols: Methanethiol 201980 201980 Ethanethiol 70000 15000 289.94 Propanethiol 20635 20635 1.81 1-Butanethiol 6070 6070 597 6.62 6.62 2.28 916.94 2-Butanethiol 10790 10790 Benzenethiol 397 397 2.52 2-Methylbenzenethiol 87.4 87.4 3-Methylbenzenethiol 76.6 76.60 4-Methylbenzenethiol 85.2 128.3 Thiophenes: Thioazole 2287 Thiophene 10620 8000 3015 35.833 35.833 1.81 223.3 224 2-Methylthiophene 3318 3-Methylthiophene 2953 Benzo[b]thiophene 26.66 26.7 130 0.969 1.107 3.12 24.1 Dibenzothiophene 0.267 1.11 0.006 4.38 44.3 Thiourea 90000 1182 36833 –0.99 Thioacetamide 163000 2170 15722 –0.26 © 2006 by Taylor & Francis Group, LLC 3436 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals TABLE 16.2.3 Suggested half-life classes for nitrogen and sulfur containing compounds in various environmental compartments at 25oC Compound Air class Water class Soil class Sediment class Acetonitrile 6 5 5 6 Propionitrile 6 5 5 6 Acrylonitrile (2-Propenitrile) 3 4 4 5 Dimethylamine 1 3 4 5 Ethylamine 2 3 4 5 Eiethylamine 1 2 2 3 n-Butylamine 2 3 3 4 Ethanolamine 1 3 3 4 Diethanolamine 1 4 4 5 Cyclohexylamine 1 3 3 4 Aniline 1 4 4 6 2-Chloroaniline 3 4 5 6 4-Chloroaniline 1 4 4 5 o-Toluidine 1 3 3 4 N,N'-Dimethylaniline 1 4 5 6 2,6-Xylidine 1 4 5 6 Diphenylamine 1 4 5 6 Benzidine 1 4 4 5 3,3'-Dichlorobenzidine 1 1 5 6 N,N'-Bianiline 1 3 3 4 .-Naphthylamine 1 4 4 6 .-Naphthylamine 1 4 4 6 Nitrobenzene 1 6 6 7 2-Nitrotoluene 2 3 6 7 4-Nitrotoluene 2 3 6 7 2,4-Dinitrotoluene (DNT) 2 3 6 7 2,4,6-Trinitrotoluene (TNT) 1 2 6 7 Acetamide 2 4 4 5 Benzamide 2 4 4 5 n-Nitrosodimethylamine 1 2 6 7 n-Nitrosodiethylamine 1 2 6 7 Di-n-propyl nitrosoamine 1 2 6 7 Diphenyl nitrosoamine 1 2 6 7 Pyridine 5 5 6 7 3-Methylpyridine 5 5 6 7 4-Methylpyridine 5 5 6 7 Quinoline 3 4 5 6 Dimethyl sulfate 4 2 2 3 Diethyl sulfate 2 2 3 4 Thiophene 3 3 6 7 Benzo[b]thiophene 4 5 6 7 Thiourea 1 4 4 5 Thioacetamide 2 4 4 5 © 2006 by Taylor & Francis Group, LLC Nitrogen and Sulfur Compounds 3437 TABLE 16.2.3 (Continued) where, Class Mean half-life (hours) Range (hours) 1 5 < 10 2 17 (~ 1 day) 10–30 3 55 (~ 2 days) 30–100 4 170 (~ 1 week) 100–300 5 550 (~ 3 weeks) 300–1,000 6 1700 (~ 2 months) 1,000–3,000 7 5500 (~ 8 months) 3,000–10,000 8 17000 (~ 2 years) 10,000–30,000 9 ~ 5 years > 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API 44, TRC Publication No. 101, Texas A & M University, College Station, TX. © 2006 by Taylor & Francis Group, LLC 3457 17 Herbicides CONTENTS 17.1 List of Chemicals and Data Compilations (in Alphabetical Order) . . . . . . . . . . . . . . . 3461 17.1.1 Herbicides . 3461 17.1.1.1 Alachlor . . . . . . . . . . . 3461 17.1.1.2 Ametryn . . . . . . . . . . . 3466 17.1.1.3 Amitrole . . . . . . . . . . . 3469 17.1.1.4 Atrazine . . . . . . . . . . . 3471 17.1.1.5 Barban . . . . . . . . . . . . 3480 17.1.1.6 Benefin . . . . . . . . . . . . 3482 17.1.1.7 Bifenox . . . . . . . . . . . . 3484 17.1.1.8 Bromacil . . . . . . . . . . . 3486 17.1.1.9 Bromoxynil . . . . . . . . 3489 17.1.1.10 sec-Bumeton . . . . . . . . 3491 17.1.1.11 Butachlor . . . . . . . . . . 3493 17.1.1.12 Butralin . . . . . . . . . . . 3495 17.1.1.13 Butylate . . . . . . . . . . . 3497 17.1.1.14 Chloramben . . . . . . . . 3499 17.1.1.15 Chlorazine . . . . . . . . . 3501 17.1.1.16 Chlorbromuron . . . . . . 3502 17.1.1.17 Chlorpropham . . . . . . 3504 17.1.1.18 Chlorsulfuron . . . . . . . 3507 17.1.1.19 Chlorotoluron . . . . . . . 3510 17.1.1.20 Cyanazine . . . . . . . . . . 3513 17.1.1.21 2,4-D . . . . . . . . . . . . . 3517 17.1.1.22 Dalapon . . . . . . . . . . . 3522 17.1.1.23 2,4-DB . . . . . . . . . . . . 3525 17.1.1.24 Diallate . . . . . . . . . . . . 3527 17.1.1.25 Dicamba . . . . . . . . . . . 3530 17.1.1.26 Dichlobenil . . . . . . . . . 3534 17.1.1.27 Dichlorprop . . . . . . . . 3537 17.1.1.28 Diclofop-methyl . . . . . 3539 17.1.1.29 Dinitramine . . . . . . . . 3542 17.1.1.30 Dinoseb . . . . . . . . . . . 3544 17.1.1.31 Diphenamid . . . . . . . . 3547 17.1.1.32 Diquat . . . . . . . . . . . . . 3549 17.1.1.33 Diuron . . . . . . . . . . . . 3551 17.1.1.34 EPTC . . . . . . . . . . . . . 3555 17.1.1.35 Ethalfluralin . . . . . . . . 3558 17.1.1.36 Fenoprop . . . . . . . . . . 3560 17.1.1.37 Fenuron . . . . . . . . . . . 3562 17.1.1.38 Fluchloralin . . . . . . . . 3564 17.1.1.39 Fluometuron . . . . . . . . 3566 © 2006 by Taylor & Francis Group, LLC 3458 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals 17.1.1.40 Fluorodifen . . . . . . . . . 3568 17.1.1.41 Fluridone . . . . . . . . . . 3569 17.1.1.42 Glyphosate . . . . . . . . . 3572 17.1.1.43 Isopropalin . . . . . . . . . 3575 17.1.1.44 Isoproturon . . . . . . . . . 3577 17.1.1.45 Linuron . . . . . . . . . . . . 3580 17.1.1.46 MCPA . . . . . . . . . . . . . 3584 17.1.1.47 MCPB . . . . . . . . . . . . 3587 17.1.1.48 Mecoprop . . . . . . . . . . 3589 17.1.1.49 Metolachlor . . . . . . . . 3591 17.1.1.50 Metribuzin . . . . . . . . . 3595 17.1.1.51 Molinate . . . . . . . . . . . 3597 17.1.1.52 Monolinuron . . . . . . . 3600 17.1.1.53 Monuron . . . . . . . . . . . 3602 17.1.1.54 Napropamide . . . . . . . 3606 17.1.1.55 Neburon . . . . . . . . . . . 3608 17.1.1.56 Nitralin . . . . . . . . . . . . 3610 17.1.1.57 Nitrofen . . . . . . . . . . . 3612 17.1.1.58 Norflurazon . . . . . . . . 3614 17.1.1.59 Oryzalin . . . . . . . . . . . 3616 17.1.1.60 Pebulate . . . . . . . . . . . 3618 17.1.1.61 Pendimethalin . . . . . . 3620 17.1.1.62 Picloram . . . . . . . . . . . 3622 17.1.1.63 Profluralin . . . . . . . . . 3626 17.1.1.64 Prometon . . . . . . . . . . 3628 17.1.1.65 Prometryn . . . . . . . . . . 3631 17.1.1.66 Pronamide . . . . . . . . . 3634 17.1.1.67 Propachlor . . . . . . . . . 3636 17.1.1.68 Propanil . . . . . . . . . . . 3639 17.1.1.69 Propazine . . . . . . . . . . 3642 17.1.1.70 Propham . . . . . . . . . . . 3645 17.1.1.71 Pyrazon . . . . . . . . . . . . 3647 17.1.1.72 Simazine . . . . . . . . . . . 3649 17.1.1.73 2,4,5-T . . . . . . . . . . . . 3653 17.1.1.74 Terbacil . . . . . . . . . . . . 3657 17.1.1.75 Terbutryn . . . . . . . . . . 3659 17.1.1.76 Thiobencarb . . . . . . . . 3662 17.1.1.77 Triallate . . . . . . . . . . . 3664 17.1.1.78 Triclopyr . . . . . . . . . . . 3668 17.1.1.79 Trifluralin . . . . . . . . . . 3670 17.1.1.80 Vernolate . . . . . . . . . . 3677 © 2006 by Taylor & Francis Group, LLC Herbicides 3459 17.1 List of Chemicals and Data Compilations (by Functional Group) . . . . . . . . . . . . . . . . 3461 Aliphatic acids: Dalapon . . . . . . . 3522 Aromatic Acids: Chloramben . . . 3499 Dicamba . . . . . . 3530 Picloram . . . . . . 3622 Amides: Alachlor . . . . . . 3461 Butachlor . . . . . 3493 Diphenamid . . . 3547 Metolachlor . . . . 3591 Napropamide . . 3606 Pronamide . . . . . 3634 Propachlor . . . . . 3636 Propanil . . . . . . . 3639 Benzonitriles: Bromoxynil . . . . 3489 Dichlobenil . . . 3534 Carbamates: Barban . . . . . . . . 3480 Chlorpropham . . 3504 Propham . . . . . . 3645 Dinitroanilines: Benefin . . . . . . . 3482 Butralin . . . . . . 3495 Dinitramine . . . . 3542 Fluchloralin . . . . 3564 Isopropalin . . . . 3575 Nitralin . . . . . . . 3610 Oryzalin . . . . . . 3616 Pendimethalin . . 3620 Profluralin . . . . . 3626 Trifluralin . . . . 3670 Diphenylethers: Bifenox . . . . . . . 3484 Fluorodifen . . . . 3568 Nitrofen . . . . . . . 3612 Phenols: Dinoseb . . . . . . . 3544 PCP (Pentachlorophenol) (See Chapter 14. Phenolic Compounds and Chapter 18. Insecticides) Phenoxyalkanoic acids: 2,4-D . . . . . . . . . 3517 2,4-DB . . . . . . . 3525 Dichlorprop . . . . 3537 Fenoprop . . . . . 3560 MCPA . . . . . . . . 3584 MCPB . . . . . . . . 3587 Mecoprop . . . . . 3589 2,4,5-T . . . . . . . 3653 Thiocarbamates: Butylate . . . . . . . 3497 Diallate . . . . . . . 3527 EPTC . . . . . . . . 3555 Molinate . . . . . . 3597 © 2006 by Taylor & Francis Group, LLC 3460 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals Pebulate . . . . . . 3618 Thiobencarb . . . 3662 Triallate . . . . . . . 3664 Vernolate . . . . . 3677 Triazines: Ametryn . . . . . . 3466 Atrazine . . . . . . 3471 sec-Bumeton . . 3491 Chlorazine . . . . . 3501 Cyanazine . . . . . 3513 Metribuzin . . . . 3595 Prometon . . . . . . 3628 Prometryn . . . . 3631 Propazine . . . . . 3642 Simazine . . . . . 3649 Terbutryn . . . . . 3659 Uracils: Bromacil . . . . . . 3486 Terbacil . . . . . . . 3657 Ureas: Chlorbromuron 3502 Chlorsulfuron . . 3507 Chlorotoluron . . 3510 Diuron . . . . . . . 3551 Fenuron . . . . . . 3562 Fluometuron . . . 3566 Isoproturon . . . . 3577 Linuron . . . . . . . 3580 Monolinuron . . 3600 Monuron . . . . . . 3602 Neburon . . . . . . 3608 Miscellaneous: Amitrole (Triazole) . . . . . . . . . . . . . . . 3469 Diclofop-methyl (Chlorophenoxy acid ester) . . . . . . . . . . . 3539 Diquat (Bipyridyl) . . . . . . . . . . . . . . . 3549 Ethalfluralin (trifluoroorg-nitro compound) . . . . . . . . . . . . 3558 Fluridone (Fluoro-phenyl pyridinone) 3569 Glyphosate (Phosphate) . . . . . . . . . . . 3572 Norflurazon . . . . 3614 Pyrazon (Pyridazinone) . . . . . . . . . . . 3647 Triclopyr (pyridine, organochlorine) . 3668 © 2006 by Taylor & Francis Group, LLC Herbicides 3461 17.1 LIST OF CHEMICALS AND DATA COMPILATIONS (By Functional Group) 17.1.1 HERBICIDES 17.1.1.1 Alachlor Common Name: Alachlor Synonym: alachlore, alochlor, Alanex, Bronco, Bullet, Cannon, Lasso, Lazo, metachlor, Pillarzo Chemical Name: 2-chloro-2,6-diethyl-N-methoxymethylacetanilide; 2-chloro-N-(2,6-diethylphenyl)-N-(methoxymethyl) acetamide Uses: pre-emergence, early post-emergence or soil-incorporated herbicide to control most annual grasses and many annual broadleaf weeds in beans, corn, cotton, milo, peanuts, peas, soybeans, sunflower, and certain woody ornamentals. CAS Registry No: 15972-60-8 Molecular Formula: C14H20ClNO2 Molecular Weight: 269.768 Melting Point (°C): 40 (Lide 2003) Boiling Point (°C): 100 (at 0.02 mmHg, Ashton & Crafts 1981; Herbicide Handbook 1989; Worthing & Hance 1991; Montgomery 1993; Tomlin 1994; Milne 1995) 135 (at 0.30 mmHg, Herbicide Handbook 1989; Milne 1995) Density (g/cm3 at 20°C): 1.133 (25°C, Hartley & Kidd 1987; Montgomery 1993; Tomlin 1994) Molar Volume (cm3/mol): 240.7 (calculated-Le Bas method at normal boiling point) Dissociation Constant pKa: Enthalpy of Fusion, .Hfus (kJ/mol): 29.288 (DSC method, Plato 1972) Entropy of Fusion, .Sfus (J/mol K): Fugacity Ratio at 25°C (assuming .Sfus = 56 J/mol K), F: 0.713 (mp at 40°C) Water Solubility (g/m3 or mg/L at 25°C or as indicated): 242 (20°C, Weber 1972; Weber et al. 1980) 200 (Bailey & White 1965) 242 (Herbicide Handbook 1974, 1978, 1983, 1989; Martin & Worthing 1977) 240 (Hartley & Graham-Bryce 1980; Beste & Humburg 1983) 148 (Khan 1980) 242 (Ashton & Crafts 1981; Worthing & Walker 1987, Worthing & Hance 1991) 242 (Hartley & Kidd 1983, 1987; Tomlin 1994) 130 (20°C, selected, Suntio et al. 1988; quoted, Majewski & Capel 1995) 148, 242 (literature data variability, Heller et al. 1989) 140 (23°C, Budavari 1989) 240 (Wauchope 1989) 240 (20–25°C, selected, Wauchope et al. 1992; Hornsby et al. 1996) 23.5 (calculated-group contribution fragmentation method, Kuhne et al. 1995) 140 (23°C, Milne 1995) 512 (predicted-AQUAFAC, Lee et al. 1996) 532, 785 (supercooled liquid SL: literature derived value LDV, final adjust value FAV, Muir et al. 2004) N O Cl O © 2006 by Taylor & Francis Group, LLC 3462 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals Vapor Pressure (Pa at 25°C or as indicated): 0.00293 (20°C, Weber 1972; Worthing & Walker 1987, Worthing & Hance 1991) 0.00293 (Herbicide Handbook 1974, 1983, 1989) 0.00293 (20–25°C, Weber et al. 1980) 0.00293 (Ashton & Crafts 1981; Schnoor & McAvoy 1981; Schnoor 1992) 0.00290 (Beste & Humburg 1983) 0.00290 (Hartley & Kidd 1987; Worthing & Hance 1991; Tomlin 1994) 0.00300 (20°C, selected, Suntio et al. 1988; quoted, Majewski & Capel 1995) 0.00187 (20–25°C, selected, Wauchope et al. 1992; Hornsby et al. 1996) 0.00413 (Montgomery 1993) 0.0064. 0.0044 (supercooled liquid PL: literature derived value LDV, final adjust value FAV, Muir et al. 2004) Henry’s Law Constant (Pa·m3/mol at 25°C or as indicated. Additional data at other temperatures designated * are compiled at the end of this section): 6.20 . 10–3 (20°C, calculated-P/C, Suntio et al. 1988) 8.43 . 10–4 (wetted-wall-GC/ECD, Fendinger & Glotfelty 1988) 3.26 . 10–3 (calculated-P/C, Taylor & Glotfelty 1988) 1.12 . 10–3 (fog chamber-GC/ECD, Fendinger et al. 1989) 8.38 . 10–4 (23°C, known LWAPC of Fendinger et al. 1989, Meylan & Howard 1991) 1.21 . 10–5 (bond-estimated LWAPC, Meylan & Howard 1991) 3.26 . 10–3 (20°C, calculated-P/C, Muir 1991) 6.20 . 10–3 (calculated-P/C, Montgomery 1993) 3.22 . 10–3 (Gish et al. 1995) 7.24 . 10–3* (Gas stripping-GC/MS, measured range 10–25°C, Gautier et al. 2003) ln [H./(M atm–1)] = –20.946 + 9200/(T/K); temp range 2830298 K (gas stripping-GC/MS, Gautier et al. 2003) 0.00101. 1.49 (literature derived value LDV, final adjust value FAV, Muir et al. 2004) Octanol/Water Partition Coefficient, log KOW: 2.92 (Leo et al. 1971) 2.30 (Kenaga 1980) 2.64 (Rao & Davidson 1980) 3.087 (shake flask, Dubelman & Bremer 1983) 3.52 (shake flask, Log P Database, Hansch & Leo 1987) 3.27 (RP-HPLC-RT correlation, Sicbaldi & Finizio 1993) 3.52 (recommended, Sangster 1993) 3.52 (recommended, Hansch et al. 1995) 3.27 (RP-HPLC-RT correlation, Finizio et al. 1997) 3.09 (literature derived value LDV, Muir et al. 2004) Octanol/Air Partition Coefficient, log KOA: 9.31 (final adjust value FAV, Muir et al. 2004) Bioconcentration Factor, log BCF: 1.45 (calculated-solubility, Kenaga 1980) 0.954 (calculated-KOC, Kenaga 1980) 1.88 (Schnoor & McAvoy 1981, Schnoor 1992) 0.778 (freshwater fish, Call et al. 1984) 1.70 (Pait et al. 1992) Sorption Partition Coefficient, log KOC: 2.28 (soil, Beestman & Demming 1976) 2.32 (soil, calculated, Kenaga & Goring 1980) 2.30 (soil, Kenaga 1980) 1.70 (sediment/water, Schnoor & McAvoy 1981) © 2006 by Taylor & Francis Group, LLC Herbicides 3463 1.91 (soil, average for soils 2–7, Weber & Peter 1982) 2.08 (soil, screening model calculations, Jury et al. 1987b) 2.28 (Carsel 1989) 2.18, 2.23, 2.28, 2.53 (soil, lit. values, Bottoni & Funari 1992) 2.23 (soil, 20–25°C, selected, Wauchope et al. 1992; Hornsby et al. 1996) 1.63–2.28 (quoted values, Montgomery 1993) 2.21 (selected, Wienhold & Gish 1994) 2.28 (soil, calculated-MCI 1., Sabljic et al. 1995) 2.28; 2.53 (soil, quoted exptl.; estimated-general model using molecular descriptors, Gramatica et al. 2000) 2.22, 2.22, 2.20 (soils: organic carbon OC . 0.1%, OC . 0.5%, 0.1 . OC < 0.5%, average, Delle Site 2001) Environmental Fate Rate Constants, k, or Half-Lives, t.: Volatilization: k(measured) = 9000 d–1 and k(estimated) = 49000 d–1 (Glotfelty et al. 1989); estimated t. = 2444 d from 1-m depth of water at 20°C (Muir 1991) Volatilization rate k = 4.4 . 10–4 d–1, 2.8 . 10–3 d–1, 4.3 . 10–3 d–1 at 15, 25, 35°C, respectively, for commercial formulation; k = 5.8 . 10–5 d–1, 8.7 . 10–3 d–1, 1.4 . 10–2 d–1 at 15, 25, 35°C, respectively, for starch encapsulated formulation after application (Weinhold et al. 1993) Photolysis: t. = 2.25 h in distilled water (Tanaka et al. 1981; quoted, Cessna & Muir 1991); 640 ppb contaminated water in the presence of TiO2 and H2O2 photodegraded to 3.5 ppb by 15 h solar irradiation with complete degradation after 75 h (Muszkat et al. 1992). Oxidation: rate constant k, for gas-phase second order rate constants, kOH for reaction with OH radical, kNO3 with NO3 radical and kO3 with O3 or as indicated, *data at other temperatures see reference: k(aq.) = (3.8 ± 0.4) M–1 s–1 for direct reaction with ozone in water at pH 2–6.0 and 21°C, with a half-life of 2.4 h at pH 7 (Yao & Haag 1991). k(calc) = 7 . 109 M–1 s–1 for the reaction with hydroxyl radical in aqueous solutions at 24 ± 1°C (Haag & Yao 1992) kOH = 2.3 . 10–11 cm3·molecule–1 s–1 with calculated tropospheric lifetime about 0.5 d at 298 K assuming an average OH concn of 1 . 106 molecule/cm3 (Gautier et al. 2003) Hydrolysis: alkaline chemical hydrolysis t. > 365 d (Schnoor & McAvoy 1981; quoted, Schnoor 1992). Biodegradation: t. < 6 months for 0.07 µg/mL to biodegrade in ground water, t. > 15 months for 10.0 µg/mL to biodegrade in groundwater both at 25°C and t. < 12 wk for 3.2 µg/mL to biodegrade in soil-water suspension at 35°C (Weidner 1974; quoted, Muir 1991); t. = 23 d for 0.244 µg/mL to biodegrade in river water at 23°C with biodegradation rate k = 0.030 d–1 (Schnoor et al. 1982; quoted, Muir 1991); t. = 18 d from screening model calculations (Jury et al. 1987b); t. > 6 wk for 0.01–1.0 µg/mL to biodegrade in sewage effluent lake water at 28°C (Novick & Alexander 1985; quoted, Muir 1991); overall degradation rate constant k = 0.0403 h–1 with t. = 17.2 h in sewage sludge and rate constant k = 0.1601 d–1 with t. = 4.3 d in garden soil (Muller & Buser 1995). Biotransformation: Bioconcentration, Uptake (k1) and Elimination (k2) Rate Constants: Half-Lives in the Environment: Air: tropospheric lifetime of 0.5 d for gas phase reaction with OH radicals; wet deposition lifetime estimated to be 2.8 d in the atmosphere by rainfall (Gautier et al. 2003) Surface water: t. = 23 d for 0.244 µg/mL to biodegrade in river water at 23°C with biodegradation rate k = 0.030 d–1 (Schnoor et al. 1982; quoted, Muir 1991); t. > 6 wk for 0.01–1.0 µg/ml to biodegrade in sewage effluent lake water at 28°C (Novick & Alexander 1985; quoted, Muir 1991); k(measured) = (3.8 ± 0.4) M–1 s–1 for direct reaction with ozone in water at pH 2–6 and 21°C, with t. = 2.4 h at pH 7 (Yao & Haag 1991). Ground water: t. < 6 months for 0.07 µg/mL to biodegrade in groundwater, and t. > 15 months for 10.0 µg/mL to biodegrade in groundwater both at 25°C (Weidner 1974; quoted, Muir 1991) reported t. = 7, 4–21 and 38 d (Bottoni & Funari 1992) Sediment: © 2006 by Taylor & Francis Group, LLC 3464 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals Soil: dissipation t. = 7.8 d in soil (Beestman & Demming 1974); measured dissipation rate k = 0.077 d–1 (Zimdahl & Clark 1982); t. = 23 and 5.7 d in soil containing 6 and 15% moisture, respectively (Walker & Brown 1985); t. = 18 d from screening model calculations (Jury et al. 1987b); estimated dissipation rate k = 0.020 and 0.036 d–1 (Nash 1988); field t. < 1.5 wk by using field lysimeters (Bowman 1990); degradation rate constant k = (4.52 ± 0.192) . 10–2 d–1 with t. = 15.3 d in control soil and k = (7.27 ± 0.772 . 10–2 d–1 with t. = 9.53 d in pretreated soil in the field; k = (2.77 ± 0.226) . 10–2 d–1 with t. = 25 d in control soil and k = (14.1 ± 1.75) . 10–2 d–1 with t. = 4.93 d in pretreated soil once only in the laboratory (Walker & Welch 1991); selected field t. = 15 d (Wauchope et al. 1992; Hornsby et al. 1996; quoted, Richards & Baker 1993); soil t. = 30 d (quoted, Pait et al. 1992); reported t. = 7, 4–21 and 38 d (Bottoni & Funari 1992); soil t. = 14–28 d (Di Guardo et al. 1994); dissipation t. = 42 d from soil surface (Gish et al. 1995); degradation t. = 4.3 d in garden soil (Muller & Buser 1995); t. = 15 d (selected, Halfon et al. 1996); dissipation t.(calc) = 5 and 5.3 d in soil in model ecosystem, t. = 3.3 and 3.4 d in water in model ecosystem (Ramesh & Maheswari 2004). Biota: biochemical t. = 18 d from screening model calculations (Jury et al. 1987b). TABLE 17.1.1.1.1 Reported Henry’s law constants of alachlor at various temperatures Gautier et al. 2003 gas stripping-GC/MS t/°C H/(Pa m3/mol) t/°C H/(Pa m3/mol) 10 1.097.10.3 23 3.46.10.3 10 1.26.10.3 25 6.33.10.3 10 1.30.10.3 25 8.44.10.3 11 9.76.10.4 25.0 7.24.10.3 12 2.115.10.3 15 1.68.10.3 Arrhenius expression: 17 2.58.10.3 ln H’/(M atm.1) = –A + B/(T/K) 18 3.13.10.3 A 20.946 20 4.24.10.3 B 9200 23 3.07.10.3 © 2006 by Taylor & Francis Group, LLC Herbicides 3465 FIGURE 17.1.1.1.1 Logarithm of Henry’s law constant versus reciprocal temperature for alachlor. Alachlor: Henry's law constant vs. 1/T -8.0 -7.0 -6.0 -5.0 -4.0 -3.0 0.0032 0.0033 0.0034 0.0035 0.0036 1/(T/K) m . a P ( / H n l 3 ) l o m / Gautier et al. 2003 Fendinger & Glotfelty 1988 Fendinger et al. 1989 © 2006 by Taylor & Francis Group, LLC 3466 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals 17.1.1.2 Ametryn Common Name: Ametryn Synonym: Amephyt, Ametrex, Evik, Gesapax Chemical Name: 6-methylthio-2-(ethylamino)-4-(isopropylamino)-1,3,5-triazine; N-ethyl-N.-(1-methylethyl)- 6-(methyl-thio)-1,3,5-triazine-2,4-diamine Uses: herbicide to control broadleaf and grass weeds in corn, sugarcane, some citrus fruits, and in noncropland; also used as pre-harvest and post-harvest dessicant in potatoes to control crop and weeds. CAS Registry No: 834-12-8 Molecular Formula: C9H17N5S Molecular Weight: 227.330 Melting Point (°C): 88 (Lide 2003) Boiling Point (°C): 328.78 (Rordorf 1989) Density (g/cm3 at 20°C): 1.19 (Hartley & Kidd 1987; Worthing & Hance 1991; Montgomery 1993; Tomlin 1994) Molar Volume (cm3/mol): 277.5 (calculated-Le Bas method at normal boiling point) Dissociation Constant: 4.00 (pKa, Weber 1970; quoted, Bintein & Devillers 1994) 4.10 (pKa, Worthing & Hance 1991; Montgomery 1993) 10.07 (pKb, Wauchope et al. 1992; Hornsby et al. 1996) 9.90 (pKb, Tomlin 1994) Enthalpy of Vaporization, .HV (kJ/mol): 91.96 (Rordorf 1989) Enthalpy of Fusion, .Hfus (kJ/mol): 19.8 (Rordorf 1989) Entropy of Fusion, .Sfus (J/mol K): 55 (Rordorf 1989) Fugacity Ratio at 25°C (assuming .Sfus = 56 J/mol K), F: 0.241 (mp at 88°C) Water Solubility (g/m3 or mg/L at 25°C or as indicated): 700 (Woodford & Evans 1963) 405, 195, 192 (26°C, shake flask-UV at pH 3.0, 7.0, 10.0, Ward & Weber 1968) 185 (Martin & Worthing 1977; Herbicide Handbook 1978) 185 (20°C, Khan 1980; Ashton & Crafts 1981; Verschueren 1983) 194 (Weber et al. 1980) 185 (20°C, Hartley & Kidd 1987; Herbicide Handbook 1989; Worthing & Hance 1991; Montgomery 1993; Milne 1995) 185 (20–25°C, selected, Wauchope et al. 1992; Hornsby et al. 1996) 200 (Tomlin 1994) 134 (calculated-group contribution fragmentation method, Kuhne et al. 1995) Vapor Pressure (Pa at 25°C or as indicated and reported temperature dependence equations): 1.12 . 10–4 (20°C, extrapolated-Antoine eq. from gas saturation-GC measurements, measured range 50–130°C, Friedrich & Stammbach 1964) (See figure at the end of this section.) log (P/mmHg) = 11.911 – 4933/(T/K), temp range 50–130°C (gas saturation-GC, data presented in Antoine eq., Friedrich & Stammbach 1964) (See figure at the end of this section.) N N N HN NH S © 2006 by Taylor & Francis Group, LLC Herbicides 3467 1.12 . 10–4 (20°C, Khan 1980; Ashton & Crafts 1981; Verschueren 1983) 1.12 . 10–4 (20°C, Hartley & Kidd 1987; Worthing & Hance 1991; Montgomery 1993) log (PS/kPa) = 11.036 – 5270/(T/K), temp range 323–403 K, (solid, Antoine eq., Stephenson & Malanowski 1987) 1.00 . 10–4 (20°C, selected, Suntio et al. 1988) 1.12 . 10–4, 4.40 . 10–4 (20°C, 30°C, Herbicide Handbook 1989) 3.74 . 10–4, 1.40 . 10–2, 0.30, 4.40, 46 (25, 50, 70, 100, 125°C, gas saturation-GC, Rordorf 1989) log (PS/Pa) = 16.85 – 6048.6/(T/K); measured range 49.5–85°C (gas saturation-GC, Rordorf 1989) log (PL/Pa) = 13.396 – 4803.6/(T/K); measured range 49.5–140°C (gas saturation-GC, Rordorf 1989) 3.65 . 10–4 (20–25°C, selected, Wauchope et al. 1992; Hornsby et al. 1996) 3.65 . 10–4 (Tomlin 1994) Henry’s Law Constant (Pa·m3/mol at 25°C or as indicated): 1.20 . 10–4 (20°C, calculated, Suntio et al. 1988) 1.38 . 10–4 (calculated-P/C, Montgomery 1993) 1.23 . 10–4 (calculated-P/C, this work) Octanol/Water Partition Coefficient, log KOW: 2.69 (Kenaga & Goring 1980) 2.58 (Gerstl & Helling 1987) 2.98 (shake flask, Log P Database, Hansch & Leo 1987) 2.82 (Worthing & Hance 1991) 2.98 (shake flask, Biagi et al. 1991) 3.07 (RP-HPLC-RT correlation, Finizio et al. 1991) 2.88 (RP-HPLC-RT correlation, Sicbaldi & Finizio 1993) 2.98 (recommended, Sangster 1993) 2.63 (Tomlin 1994) 2.61 (shake flask-UV, Liu & Qian 1995) 2.58 (calculated-RP-HPLC-k. correlation, Liu & Qian 1995) 2.83 (Milne 1995) 2.98 (recommended, Hansch et al. 1995) 2.88 (RP-HPLC-RT correlation, Finizio et al. 1997) Bioconcentration Factor, log BCF: 1.52 (calculated-S, Kenaga 1980) 1.32 (calculated-KOC, Kenaga 1980) Sorption Partition Coefficient, log KOC: 2.59 (soil, Hamaker & Thompson 1972;) 2.40 (soil, calculated, Kenaga & Goring 1980) 2.59 (soil, Kenaga & Goring 1980) 2.59 (Rao & Davidson 1980) 2.59, 2.86 (quoted, calculated-MCI ., Gerstl & Helling 1987) 2.59, 2.51 (reported as log KOM, estimated as log KOM, Magee 1991) 2.40–2.59, 2.58 (soil, quoted values, Bottoni & Funari 1992) 2.48 (soil, 20–25°C, selected, Wauchope et al. 1992; Hornsby et al. 1996) 2.23–2.44 (Montgomery 1993) 2.48 (Tomlin 1994) 2.42 (calculated-KOW, Liu & Qian 1995) 2.59 (soil, calculated-MCI 1., Sabljic et al. 1995) 2.70, 2.59 (soil, estimated-class-specific model, estimated-general model using molecular descriptors, Gramatica et al. 2000) 2.52, 2.63, 2.60, 2.35 (soils with organic carbon OC . 0.5% at: pH 4.5–9.0, pH 4.5–5.4, pH 5.5–6.0, pH-6.1, average, Delle Site 2001) 1.84, 2.23 (Kishon river sediments, sorption isotherm, Chefetz et al. 2004) © 2006 by Taylor & Francis Group, LLC 3468 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals Environmental Fate Rate Constants, k, or Half-Lives, t.: Volatilization: Photolysis: t. = 10 h for 10 µg mL–1 to degrade in distilled water under > 290 nm light and t. = 3.3 h in 1% acetone solution (Burkhard & Guth 1976; quoted, Cessna & Muir 1991); t. = 2.25 h for 17% of 33 µg mL–1 to degrade in 0.2% aqueous solutions of the surfactant Triton X-100 and for 8% of 33 µg/mL to degrade in distilled water both under 300 nm light (Tanaka et al. 1981; quoted, Cessna & Muir 1991). Oxidation: Hydrolysis: t. = 32 d at pH 1 and t. > 200 d at pH 13 (Montgomery 1993). Biodegradation: Biotransformation: Bioconcentration, Uptake (k1) and Elimination (k2) Rate Constants: Half-Lives in the Environment: Air: Surface water: Groundwater: reported half-lives or persistence, t. = 7–120 d (Bottoni & Funari 1992) Sediment: Soil: t. = 6.0 months at 15°C and t. = 4.5 months at 30°C in soils (Freed & Haque 1973); t. = 70–120 d (Bottoni & Funari 1992); selected t. = 60 d (Wauchope et al. 1992; Hornsby et al. 1996); t. = 70–129 d in soil (Tomlin 1994). Biota: FIGURE 17.1.1.2.1 Logarithm of vapor pressure versus reciprocal temperature for ametryn. Ametryn: vapor pressure vs. 1/T -5.0 -4.0 -3.0 -2.0 -1.0 0.0 1.0 2.0 3.0 0.0022 0.0024 0.0026 0.0028 0.003 0.0032 0.0034 0.0036 1/(T/K) P( gol S ) aP/ Friedrich & Stammbach 1964 (50 to 130 °C) Friedrich & Stammbach 1964 (extrapolated) m.p. = 88 °C © 2006 by Taylor & Francis Group, LLC Herbicides 3469 17.1.1.3 Amitrole Common Name: Amitrole Synonym: Amazole, Amitrol, Amizole, aminotriazole, Azolan, Azole, cytrol, Diurol Chemical Name: 3-amino-1,2,4-triazole; 3-amino-s-triazole; 1H-1,2,4-triazol-3-amine Uses: nonselective, foliage-applied herbicide in uncropped land and orchards to control perennial weeds in certain grasses. CAS Registry No: 61-82-5 Molecular Formula: C2H4N4 Molecular Weight: 84.080 Melting Point (°C): 159 (Khan 1980; Herbicide Handbook 1989; Lide 2003) Boiling Point (°C): Density (g/cm3 at 20°C): 1.138 (Hartley & Kidd 1987; Herbicide Handbook 1989; Montgomery 1993; Tomlin 1994) Molar Volume (cm3/mol): 85.1 (calculated-Le Bas method at normal boiling point) Dissociation Constant: 9.83 (pKb, Wauchope et al. 1992; Hornsby et al. 1996) Enthalpy of Fusion, .Hfus (kJ/mol): 24.69 (DSC method, Plato 1972) Entropy of Fusion, .Sfus (J/mol K): Fugacity Ratio at 25°C (assuming .Sfus = 56 J/mol K), F: 0.0484 (mp at 159°C) Water Solubility (g/m3 or mg/L at 25°C or as indicated): 252000 (Freed & Burschel 1957) 280000 (Martin 1961; Spencer 1981) 280000 (Bailey & White 1965; Khan 1980; Weber et al. 1980; Ashton & Crafts 1981; Willis & McDowell 1982) soluble (Wauchope 1978) 280000 (Worthing 1983, Worthing & Hance 1991) 280000 (Hartley & Kidd 1987; Herbicide Handbook 1989; Reinert 1989) 360000 (20–25°C, selected, Wauchope et al. 1992; Lohninger 1994; Hornsby et al. 1996) 280000 (20°C at pH 7, quoted, Montgomery 1993) 280000 (23°C, Tomlin 1994) Vapor Pressure (Pa at 25°C or as indicated): < 0.001 (Agrochemicals Handbook 1983; quoted, Howard 1991) < 0.001 (Hartley & Kidd 1987) 5.50 . 10–8 (20°C, Worthing & Hance 1991; Tomlin 1994) 5.87 . 10–5 (20–25°C, selected, Wauchope et al. 1992; Hornsby et al. 1996) 5.51 . 10–7 (20°C, quoted, Montgomery 1993) Henry’s Law Constant (Pa·m3/mol at 25°C or as indicated): < 3.04 . 10–7 (calculated-P/C, Howard 1991) 1.650 . 10–10 (20°C, calculated-P/C, Montgomery 1993) 1.650 . 10–10 (calculated-P/C, this work) N NH N NH2 © 2006 by Taylor & Francis Group, LLC 3470 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals Octanol/Water Partition Coefficient, log KOW: –0.85 (shake flask, pH 7, Lichtner 1983) 0.52 (selected, Dao et al. 1983; Gerstl & Helling 1987) –0.15 (Reinert 1989; quoted, Howard 1991; Montgomery 1993) –0.87, –0.84 (pH 7) (Hansch et al. 1995) –0.87 (LOGPSTAR or CLOGP data, Sabljic et al. 1995) Bioconcentration Factor, log BCF: –0.301 (estimated-S, Lyman et al. 1982; quoted, Howard 1991) –0.347 (estimated-log KOW, Lyman et al. 1982; quoted, Howard 1991) Sorption Partition Coefficient, log KOC: 2.04 (soil, estimated-molecular topology & QSAR, Sabljic 1984) 0.23 (calculated-MCI ., Gerstl & & Helling 1987) 1.26 (Reinert 1989) 2.00 (soil, 20–25°C, selected, Wauchope et al. 1992; Hornsby et al. 1996) 1.73–2.31 (quoted, Montgomery 1993) 2.00 (estimated-chemical structure, Lohninger 1994) 1.25 (soil, calculated-MCI 1., Sabljic et al. 1995) Environmental Fate Rate Constants, k, or Half-Lives, t.: Volatilization: Photolysis: Oxidation: photooxidation t. = 3.2–32 h in air, based on estimated rate constant for the vapor-phase reaction with hydroxyl radicals in air (Atkinson 1987; quoted, Howard et al. 1991). Hydrolysis: Biodegradation: aqueous aerobic t. = 672–4032 h, based on reported half-lives in soil and water (Freed & Haque 1973; Reinert & Rogers 1987; quoted, Howard et al. 1991); aqueous anaerobic t. = 2688–16128 h, based on estimated aqueous aerobic biodegradation half-life (Howard et al. 1991). Biotransformation: Bioconcentration, Uptake (k1) and Elimination (k2) Rate Constants: Half-Lives in the Environment: Air: t. = 3.8 d, based on a theoretical calculation for the vapor-phase reaction with hydroxyl radicals in the atmosphere at 25°C (GEMS 1986; quoted, Howard 1989); t. = 3.2–32 h, based on estimated rate constant for the vapor-phase reaction with hydroxyl radicals in air (Atkinson 1987; quoted, Howard et al. 1991). Surface water: t. = 672–4320 h, based on estimated aqueous aerobic biodegradation half-life (Howard et al. 1991). Groundwater: t. = 1344–8640 h, based on estimated aqueous aerobic biodegradation half-life (Howard et al. 1991).‘ Sediment: Soil: t. = 1.4, 1.6, 1.3, 92, 36, and 56 d with disappearance rates: k = 0.495, 0.433, 0.533, 0.0075, 0.0193, and 0.124 d–1 at pH 6.0, 7.0, 8.0, 5.3, 6.5, and 7.5 (Hamaker 1972; quoted, Nash 1988); t. = 1.5 month at 15°C and t. = 1.0 month at 30°C in soils (Freed & Haque 1973); persistence of one month in soil (Wauchope 1978); persistence in soil for ca. 2–4 wk (Herbicide Handbook 1989; Tomlin 1994); t. = 672–4320 h, based on estimated aqueous aerobic biodegradation half-life (Howard et al. 1991); selected field t. = 14 d (Wauchope et al. 1992; Hornsby et al. 1996). Biota: © 2006 by Taylor & Francis Group, LLC Herbicides 3471 17.1.1.4 Atrazine Common Name: Atrazine Synonym: Aatrex, Akikon, Aktikon, Aktinit, Atratol, Atred, Atrex, Candex, Fenamine, Gesaprim, Hungazin, Inakor, Primatol, Primaze, Radazine, Strazine, Triazine A, Vectal, Weedex A, Wonuk, Zeazine Chemical Name: 2-chloro-4-(ethylamino)-6-(isopropylamino)-1,3,5-triazine; 6-chloro-N-ethyl-N.-(1-methylethyl)-1,3,5- triazine-diamine Uses: pre-emergence and post-emergence herbicide to control some annual grasses and broadleaf weeds in corn, fallow land, rangeland, sorghum, noncropland, certain tropical plantations, evergreen nurseries, fruit crops, and lawns. CAS Registry No: 1912-24-9 Molecular Formula: C8H14ClN5 Molecular Weight: 215.684 Melting Point (°C): 173 (Lide 2003) Boiling Point (C): Density (g/cm3 at 20°C): 1.187 (Worthing & Hance 1991; Montgomery 1993; Tomlin 1994) Molar Volume (cm3/mol): 250.6 (calculated-Le Bas method at normal boiling point) Dissociation Constant: 1.68 (pKa, Weber 1970; Somasundaram et al. 1991; Bintein & Devillers 1994) 1.70 (pKa, Weber et al. 1980; Willis & McDowell 1982; Worthing & Hance 1991; Francioso et al. 1992; Montgomery 1993; Tomlin 1994) 1.60 (pKa, Yao & Haag 1991; Haag & Yao 1992) 12.32 (pKb, Wauchope et al. 1992; Hornsby et al. 1996) 1.62 (pKa, 20°C, Montgomery 1993) Enthalpy of Fusion, .Hfus (kJ/mol): 40.585 (DSC method, Plato 1972) Entropy of Fusion, .Sfus (J/mol K): Fugacity Ratio at 20°C (assuming .Sfus = 56 J/mol K), F: 0.0353 (mp at 173°C) Water Solubility (g/m3 or mg/L at 25°C or as indicated): 70.0 (26°C, Bailey & White 1965) 50.0 (Gunther et al. 1968) 31.1, 34.9, 36.8 (26°C, shake flask-UV at pH 3.0, 7.0. 10.0, Ward & Weber 1968) 98.0 (50°C, Getzen & Ward 1971) 33.0 (shake flask-GC, Hormann & Eberle 1972) 29.9 (shake flask-UV, Hurle & Freed 1972) 30.0 (20°C, Weber 1972; Worthing & Walker 1987; Worthing & Hance 1991; Burkhard & Guth 1981) 33.0 (27°C, Ashton & Crafts 1973, 1981; Khan 1980; Herbicide Handbook 1989; Pait et al. 1992) 32.0 (Freed 1976; Beste & Humburg 1983; Jury et al. 1983) 31.5 (Spencer 1976) 33.0 (Wauchope 1978; Kenaga 1980; Kenaga & Goring 1980) 35.0 (Weber et al. 1980) 30.0 (shake flask-HPLC, Ellgehausen et al. 1981) 24.0 (Thomas 1982) 70.0 (Windholz 1983) N N N HN NH Cl © 2006 by Taylor & Francis Group, LLC 3472 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals 28.0 (20°C, Hartley & Kidd 1987) 29.9, 33, 70 (literature data variability, Heller et al. 1989) 33.0 (20–25°C, selected, Wauchope et al. 1992; Hornsby et al. 1996) 28.0, 33.0 (20°C, 27°C, Montgomery 1993) 33.0 (20°C, Tomlin 1994) 28.0 (Milne 1995) 4012, 4012 (supercooled liquid SL: literature derived value LDV, final adjust value FAV, Muir et al. 2004) Vapor Pressure (Pa at 25°C or as indicated and reported temperature dependence equations. Additional data at other temperatures designated * are compiled at the end of this section): 44.0 . 10–5* (20°C, extrapolated-Antoine eq. from gas saturation-GC measurements, measured range 50–130°C, Friedrich & Stammbach 1964) log (P/mmHg) = 13.766 – 5945/(T/K), temp range 50–130°C (gas saturation-GC, data presented in graph and Antoine eq., Friedrich & Stammbach 1964) 4.00 . 10–5 (20°C, Weber 1972; Worthing 1979; Worthing & Walker 1987, Worthing & Hance 1991; quoted, Khan 1980; Dobbs et al. 1984; Muir 1991) 3.99 . 10–5 (20°C, gas saturation, extrapolated from Friedrich & Stammbach 1964, Spencer 1976) 4.00 . 10–5 (20°C, Hartley & Graham-Bryce 1980; Beste & Humburg 1983) 4.00 . 10–5 (20–25°C, Weber et al. 1980) 4.00 . 10–5 (20°C, Ashton & Crafts 1981) 1.33 . 10–4 (selected, Schnoor & McAvoy 1981) 3.70 . 10–5* (20°C, extrapolated from gas saturation measurement, Grayson & Fosbracey 1982) ln (P/Pa) = 36.8 – 13778/(T/K), for temp range 51–81.5°C, (Antoine eq., gas saturation, Grayson & Fosbracey 1982) 1.13 . 10–4 (Thomas 1982) 4.00 . 10–5 (20°C, Hartley & Kidd 1987) log (PS/kPa) = 12.8909 – 5945/(/K), temp range 323–403 K, (solid, Antoine eq., Stephenson & Malanowski 1987) 8.70 . 10–5 (selected, Nash 1989) 3.99 . 10–5, 18.6 . 10–5 (20°C, 30°C, Herbicide Handbook 1989) 3.90 . 10–5* (gas saturation-GC, measured range 40.5–125°C, Rordorf 1989) log (PS/Pa) = 13.27071 – 6558.5/(T/K); measured range 40.5–125°C (gas saturation-GC, Rordorf 1989) log (PL/Pa) = 13.396 – 4803.6/(T/K); measured range not specified (gas saturation-GC, Rordorf 1989) 4.05 . 10–5 (Riederer 1990) 3.85 . 10–5 (20–25°C, selected, Wauchope et al. 1992; Hornsby et al. 1996) 4.00 . 10–5 (20°C, Montgomery 1993) 2.00 . 10–5 (selected, Sieber et al. 1994) 3.90 . 10–5 (Tomlin 1994; quoted, Halfon et al. 1996) 6.70 . 10–4* (40°C, Knudsen effusion method, measured range 40–80°C, Goodman 1997) log (P/Pa) = 16.08 – 6040/(T/K); temp range 40–80°C, Goodman 1997) 0.0096, 0.0096 (supercooled liquid PL: literature derived value LDV, final adjust value FAV, Muir et al. 2004) Henry’s Law Constant (Pa·m3/mol at 25°C or as indicated): 6.20 . 10–4 (calculated-P/C, Jury et al. 1983, 1984, 1987a; Jury & Ghodrati 1989) 2.90 . 10–4 (20°C, calculated-P/C, Suntio et al. 1988) 6.19 . 10–4 (calculated-P/C, Taylor & Glotfelty 1988) 5.70 . 10–4 (calculated-P/C, Nash 1989) 3.04 . 10–4 (Riederer 1990) 2.66 . 10–4 (calculated-P/C, Howard 1991) 2.89 . 10–4 (20°C, calculated-P/C, Muir 1991) 3.08 . 10–4 (20°C, calculated-P/C, Montgomery 1993) 1.00 . 10–3 (calculated-P/C, Sieber et al. 1994) 6.20 . 10–4 (Gish et al. 1995) 2.88 . 10–4 (calculated-P/C, this work) 0.518 (final adjust value FAV, Muir et al. 2004) © 2006 by Taylor & Francis Group, LLC Herbicides 3473 Octanol/Water Partition Coefficient, log KOW: 2.75 (shake flask-GC, Erkell & Walum 1979) 2.63 (HPLC-RT correlation, Veith et al. 1979, 1980; Veith & Kosian 1982) 2.35 (Rao & Davidson 1980) 2.71 (shake flask-both phases analyzed by GC and UV spec., Brown & Flagg 1981) 2.40, 2.21 (HPLC-k. correlation, McDuffie 1981) 2.75 (shake flask, Ellgehausen et al. 1981) 2.80 (Elgar 1983) 2.05 (RP-HPLC-k. correlation, Braumann et al. 1983) 2.64 (shake flask-GC, Geyer et al. 1984) 2.75 (Hansch & Leo 1985) 2.64 (OECD method 1981, Kerler & Schonherr 1988) 2.68 (Lopez-Avila et al. 1989) 2.61, 2.61 (RP-HPLC-RT correlation, calculated, Finizio et al. 1991) 2.34 (Worthing & Hance 1991; Milne 1995) 2.10 (shake flask, pH 7, Baker et al. 1992) 2.33–2.80 (quoted values, Montgomery 1993) 2.75 (recommended, Sangster 1993) 2.42 (RP-HPLC-RT correlation, Sicbaldi & Finizio 1993) 2.50 (Tomlin 1994) 2.27 (shake flask-UV, Liu & Qian 1995) 2.61 (selected, Hansch et al. 1995) 2.43 (RP-HPLC-RT correlation, Finizio et al. 1997) 2.00 (RP-HPLC-RT correlation using short ODP column, Donovan & Pescatore 2002) 2.63 ± 0.07, 2.47 ± 0.15, 2.46 ± 0.09 (shake flask, isocratic RP-HPLC-k. correlation, gradient RP-HPLC-k. correlation, Paschke et al. 2004) 2.40 (literature derived value LDV, Muir et al. 2004) Octanol/Air Partition Coefficient, log KOA: 9.08 (final adjust value FAV, Muir et al. 2004) Bioconcentration Factor, log BCF: –2.00 (vegetation, correlated-KOW, Beynon et al. 1972; quoted, Travis & Arms 1988) 1.04 (Metcalf & Sanborn 1975; quoted, Kenaga & Goring 1980; Isensee 1991) 1.00 (Isensee 1976) 0.50 (whitefish, Burkhard & Guth 1976) 0.90 (fathead minnow, Veith et al. 1979) 0.30 (catfish, Ellgehausen et al. 1980; quoted, Howard 1991) 0.26 (Daphnia magna, wet wt. basis, Ellgehausen et al. 1980) 0.48 (Corygonus fera. at 12°C, Gunkel & Streit 1980) 1.93, 0.845 (calculated-S, KOC, Kenaga 1980) < 0.90 (Veith et al. 1980) 1.90 (selected, Schnoor & McAvoy 1981) 1.93, 1.77 (estimated-S, estimated-KOW, Bysshe 1982) 0.90 (fathead minnow, Veith & Kosian 1982) 2.00 (mottled sculpin, Lynch et al. 1982) 1.60 (activated sludge, Freitag et al. 1984) 1.00 (golden ide, Freitag et al. 1985) 0.477, 0.954, 0.845, 0.778 (zebrafish: egg, embryo, yolk sac fry, juvenile; Gorge & Nagel 1990) 0.78 (Brachydanio rerio, Gorge & Nagel 1990) 0.983 (Hydrilla, Hinman & Klaine 1992) 1.98, 0.748, 0.230 (algae Scenedesmus acutus, catfish Ictalurus melas, Daphnia magna, wet wt basis, Wang et al. 1996) © 2006 by Taylor & Francis Group, LLC 3474 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals Bioaccumulation Factor, log BAF: 1.710 (algae, Ellgehausen et al. 1980;) 0.329 (catfish, Ellgehausen et al. 1980) 0.261 (daphnids, Ellgehausen et al. 1980) 1.72, 0.477, 1.60 (algae, fish, sludge, Klein et al. 1984) 1.70, < 1.00, 1.60 (algae, fish, sludge, Freitag et al. 1985) Sorption Partition Coefficient, log KOC at 25°C or as indicated: 2.17 (soil, Hamaker & Thompson 1972) 2.09 (average of 4 soils, Rao & Davidson 1979; Davidson et al. 1980) 2.81 (calculated, Kenaga & Goring 1980; Kenaga 1980) 2.20 (average of soils/sediments, Rao & Davidson 1980) 2.21 (average of 56 soils from lit. review, Rao & Davidson 1980) 2.33 (a Georgia pond sediment, sorption isotherms by shake flask-GC/ECD, Brown & Flagg 1981) 1.59 (a Swiss soil, Burkhard & Guth 1981) 3.11, 2.31; 1.94, 2.42 (estimated-S, calculated-S and mp; estimated-KOW, Karickhoff 1981) 0.7–1.48 (selected, sediment/water, Schnoor & McAvoy 1981) 2.18 (soil, Thomas 1982) 2.29–3.18 (Wolf & Jackson 1982) 3.23–4.13 (Means & Wijayaratne 1982) 2.21 (soil average, Jury et al. 1983) 1.63–3.29 (Wauchope & Myers 1985; 1991) 2.46 (calculated-MCI ., Gerstl & Helling 1987) 2.20 (soil, screening model calculations, Jury et al. 1987a,b; Jury & Ghodrati 1989) 1.92 (RP-HPLC-k. correlation, cyanopropyl column, Hodson & Williams 1988) 2.21 (estimated as log KOM, Magee 1991) 2.0, 2.18, 2.17–2.81, 2.26 (soil, literature values, Bottoni & Funari 1992) 2.27, 2.41, 2.59, 2.16 (soils, no. 1, 2, 3, 4; Francioso et al. 1992) 1.81 (soil, HPLC-screening method, mean value from different stationary and mobile phases, Kordel et al. 1993, 1995a,b) 2.00 (soil, 20–25°C, selected, Wauchope et al. 1992; quoted, Dowd et al. 1993; Richards & Baker 1993; Wienhold & Gish 1994; Hornsby et al. 1996) 1.95–2.71 (quoted values, Montgomery 1993) 2,60 (soil with 9.23% organic carbon, Donati et al. 1994) 2.04 (agricultural soil, Dousset et al. 1994) 2.40 (estimated-chemical structure, Lohninger 1994) 2.05 (soil with low organic carbon 0.18%, Roy & Krapac 1994) 1.95–2.19 (Tomlin 1994) 2.23 (calculated-KOW, Liu & Qian 1995) 2.24 (soil, calculated-MCI 1., Sabljic et al. 1995) 1.81; 2.36 (HPLC-screening method; calculated-PCKOC fragment method, Muller & Kordel 1996) 1.00 (sediment/water, Chung et al. 1996) 2.64 (Levy wetland soil, sorption equilibrium technique, 24°C, Mersie & Seybold 1996) 2.14–2.21; 2.03–2.12 (Teufelsweiher pond sediment: field measurement; exptl laboratory data, Gao et al. 1997) 2.19 (sediment from Teufelsweiher pond, batch equilibrium isotherm, Gao et al. 1998) 1.93, 1.80–1.85, 1.81 (soil, liquid sewage sludge amended soil, sludge, pH 7.2, batch equilibrium-sorption isotherm, Celis et al. 1998) 1.93, 1.83, 1.79 (soil + CaCl2 at pH 7.2, soil + liquid sewage sludge and dissolved organic matter at pH 7.5, soil + liquid sewage sludge at pH 7.2, batch equilibrium-sorption isotherm, Celis et al. 1998) 2.566, 1.72, 1.75, 1.505, 2.40 (first generation Eurosoils ES-1, ES-2, ES-3, ES-4, ES-5, shake flask/batch equilibrium- HPLC/UV, Gawlik et al. 1998, 1999) 2.24, 2.45; 2.82., 1.81, 2.81, 1.98, 1.99 (quoted lit., calculated-KOW; HPLC-screening method with different LCcolumns, Szabo et al. 1999) 2.154, 1.97, 1.77, 1.61, 2.496 (second generation Eurosoils ES-1, ES-2, ES-3, ES-4, ES-5, shake flask/batch equilibrium-HPLC/UV, Gawlik et al. 1999) © 2006 by Taylor & Francis Group, LLC Herbicides 3475 1.69 (sandy loam soil, column equilibrium method, 20°C, Xu et al. 1999) 2.154, 1.969, 1.769, 1,610, 2.486 (second generation Eurosoils ES-1, ES-2, ES-3, ES-4, ES-5, shake flask/batch equilibrium-HPLC/UV and HPLC-k. correlation, Gawlik et al. 2000) 2.24; 2.27, 2.47 (soil, quoted obs.; estimated-class-specific model, estimated-general model using molecular descriptors, Gramatica et al. 2000) 2.59, 2.16 (average values for sediments, soils, Delle Site 2001) 2.31, 2.17, 2.56 (soils: organic carbon OC . 0.1%, OC . 0.5%, 0.1 . OC < 0.5%, and pH 3.2–8.2, average, Delle Site 2001) 2.34, 2.24, 2.06, 2.59 (soils with organic carbon OC . 0.5% at: pH 3.2–5.0, pH 5.1–5.9, pH-6.0, pH 4.4–7.7, average, Delle Site 2001) 1.77, 2.10 (Kishon river sediments, sorption isotherm, Chefetz et al. 2004) Environmental Fate Rate Constants, k, or Half-Lives, t.: Volatilization: initial rate constant k = 6.4 . 10–4 h–1 and predicted rate constant k = 4.2 . 10–4 h–1 from soil with t. = 1650 h (Thomas 1982); t. = 97 d (Jury et al. 1983; quoted, Grover 1991); rate constants k(measured) = 1100 d–1 and k(est.) = 6000 d–1 (Glotfelty et al. 1989); Half-lives from soil surfaces: t. = 655 to > 1000 d in peat soil and t. = 143–939 d in sandy soil; half-lives from plant surfaces: t. = 25.6 d in bean, t. = 24.3 d in turnips and t. = 14.6 d in oats at 20 ± 1°C (Dorfler et al. 1991) Volatilization rate k = 1.4 . 10–4 d–1, 2.6 . 10–3 d–1, 4.4 . 10–3 d–1 at 15, 25, 35°C, respectively, for commercial formulation; k = 1.2 . 10–5 d–1, 4.8 . 10–4 d–1, 8.1 . 10–4 d–1 at 15, 25, 35°C, respectively, for starchencapsulated formulation after application (Weinhold et al. 1993) Photolysis: t. = (19 ± 9) h under summer sunlight of 9.1 h d–1 exposure and t. = 61 ± 29 h under spring sunlight of 3.7 h d–1 exposure in 10 ppm aqueous solutions: (Burkhard et al. 1975); t. = 4.9 h for 10 µg/mL to degrade in 1% acetone solution and t. = 25 h for 10 µg/mL to degrade in distilled water both under > 290 nm light (Burkhard & Guth 1976); nearsurface direct sunlight photolysis rate constant k = 9 . 10–6 d–1 with t. = 81,000 d (Schnoor & McAvoy 1981; quoted, Schnoor 1992); t. = 2.25 h for 17–27% of 100 µg/mL to degrade in distilled water under 300 nm light (Tanaka et al. 1981; quoted, Cessna & Muir 1991); rate of photolytic degradation was slightly higher in water (t. = 3–12 d) than in sediments (t. = 1–4 wk) (Jones et al. 1982; quoted, Montgomery 1993); 40 ppb contaminated water in presence of TiO2 and H2O2 degraded to 4 ppb after 15 h by solar irradiation with complete degradation after 75 h (Muszkat et al. 1992) t.(aq.) = 335 d at pH 7 under natural light; t. = 17.5 h at pH 7 using mercury lamp in aqueous solution; soil photolysis t.= 12 d under natural light, t. = 5 d using mercury lamp and t. = 45 d using xenon lamp (Solomon et al. 1996); Oxidation: rate constant k, for gas-phase second order rate constants, kOH for reaction with OH radical, kNO3 with NO3 radical and kO3 with O3 or as indicated, *data at other temperatures see reference: kOH = 147.2 . 10–12 cm3 molecule–1 s–1 with n half-life of 2.6 h at 25°C for the vapor-phase reaction with hydroxyl radical in air (Atkinson 1987; quoted, Howard et al. 1991); k(aq.) = 5.9 . 109 M–1 s–1 for the reaction (photo-Fenton with reference to acetophenone) with OH radical in aqueous solutions at pH 3.6 and 24 ± 1°C (Buxton et al. 1988; quoted, Faust & Hoigne 1990; Haag & Yao 1992) k(aq.) = (24 ± 4) M–1 s–1 for direct reaction with ozone at pH 4 and 26°C; k = (13 ± 1) M–1 s–1 at pH 4.2 and 21°C and k = (24 ± 4) M–1 s–1 at pH 4.1 and 19°C in water, with a half-life of 1.5 h at pH 7 (Yao & Haag 1991) k(aq.) = (2.6 ± 0.4) . 109 M–1 s–1 for the reaction (photo-Fenton with reference to acetophenone) with hydroxyl radical in aqueous solutions at pH 3.6 and 24 ± 1°C (Haag & Yao 1992) k(aq.) = 0.82 . 109 M–1 s–1 for reaction with hydroxyl radical in irradiated field water (Mabury & Crosby 1996) © 2006 by Taylor & Francis Group, LLC 3476 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals Hydrolysis: t. ~ 70 d at pH 3.1 of citrate buffer; t. ~ 75 d at pH 11.1 of carbonate buffer and t. ~ 2 d at 3.9 of phosphate buffer + sterile lake sediment in aqueous solutions at 25°C (Armstrong et al. 1967; quoted, Muir 1991) Over all rate constant k = 7.6 . 10–5 s–1 with t. = 2.5 h at 25°C and pH 7 (Mabey & Mill 1978) t. = 3.3, 14, 58, 240, 100, 12.5, and 1.5 d at pH 1, 2, 3, 4, 11, 12, and 13, respectively, in aqueous buffered solutions in soil at 25°C (Armstrong et al. 1967; quoted, Montgomery 1993); t. = 244 d without humic materials, t. = 1.37 d with the presence of 2% humic acid at pH 4 and 25°C (Li & Felbeck 1972; quoted, Howard 1991; Montgomery 1993) k = 3.9 . 10–5 M–1 s–1 and k = 7.6 . 10–5 M–1 s–1 with t. = 66 and 81 d in aqueous solutions of pH 3.1 and 11.1, respectively (Wolfe et al. 1976; quoted, Muir 1991) k(aq.) = 19.9 d–1 at pH 2.9, k = 3.99 d–1 at pH 4.5, k = 1.74 d–1 at pH 6.0, and k = 0.934 d–1 at pH 7.0 with corresponding t. = 34.8, 174, 398, and 742 d all at 25°C in 0.5 mg mL–1 concn. of aqueous fulvic acid (Khan 1978; quoted, Howard 1991; Montgomery 1993) k(aq.) = 28.4 d–1 at pH 2.8, k = 12.6 d–1 at pH 4.5, k = 3.16 d–1 at pH 6.0, and k = 1.23 d–1 at pH 7.0 with corresponding t. = 24.4, 55.0, 219, and 563 d all at 25°C in 1.0 mg mL–1 concn. of aqueous fulvic acid (Khan 1978) k(aq.) = 151 d–1 at pH 2.4, k = 43.7 d–1 at pH 4.5, k = 13.2 d–1 at pH 6.0, and k = 7.93 d–1 at pH 7.0 with corresponding t. = 4.60, 15.9, 52.5 and 87.3 d all at 25°C in 5.0 mg mL–1 concn. of aqueous fulvic acid (Khan 1978) k(aq.) = 9.30 . 10–6 s–1 with t. = 86 d at 20°C in a buffer at pH 5 (Burkhard & Guth 1981; quoted, Muir 1991) t. > 3 months (in sterile buffer solution at pH 7.2) and t. > 14 d (in sterile mineral salt solution at pH 7.2) for 20 µg mL–1 to hydrolyze at 23°C (Geller 1980; quoted, Muir 1991) k(alkaline) = 1 . 10–16 M–1 s–1 with t. = 742 d (Schnoor & McAvoy 1981; quoted, Schnoor 1992) t. = 1771 yr at pH 7 and 25°C (Montgomery 1993) Biodegradation: t. = 64 d in soil (Armstrong et al. 1967; Dao et al. 1979; quoted, Means et al. 1983) t. = 3.21 d in aqueous solution from river die-away tests (Furmidge & Osgerby 1967; quoted, Scow 1982) t.(aerobic) > 90 d for 10–20 µg mL–1 to degrade in soil-water suspension (Goswami & Green 1971; quoted, Muir 1991) k(aq.) = 0.019 d–1 by soil incubation die-away studies (Rao & Davidson 1980; quoted, Scow 1982); t.(aerobic) > 35 d for 0.1–1.0 µg mL–1 to slowly biodegrade in sediment/water at 25°C (Wolf & Jackson 1982; quoted, Muir 1991) t. = 36 and 110 d in soil (Jones et al. 1982; quoted, Means et al. 1983) t. = 71 d for a 100 d leaching and screening test in 0–10 cm depth of soil (Jury et al. 1983, 1984, 1987a; Jury & Ghodrati 1989; quoted, Grover 1991) k = 0.22 d–1 of aerobic degradation rate observed in incubations of river water samples (Lyman et al. 1990; quoted, Hemond & Fechner 1994) t. = 201 d with 12 mM methanol, for aqueous atrazine using first-order decay rate, t. = 289 d with 6 mM sodium acetate, t. = 164 d with 6 mM acetic acid and t. = 200 d with 2 mM glucose; however t. = 224 d in the sample reactors without any organic amendments (Chung et al. 1996) degradation t. = 39 h and 43 h by soil micro Rhodococcus. sp. NI86/21 with atrazine concn 4 µg/mL and 8 µg/mL respectively (Van Zwieten & Kennedy 1995) first order removal of atrazine from sediment organic carbon: k = –0.0054 d–1 with t. = 128 d in surface sediment 0–6 cm depth, k = –0.0016 d–1 with t. = 433 d in sub-surface sediment 24–34 cm depth from Blue Heron Pond; k = –0.007 d–1 with t. = 99 d in surface sediment 0–6 cm depth, k = –0.0022 d–1 with t. = 630 d in sub-surface sediment 24–34 cm depth rom Oyster Rake Pond; k = –0.0142 d–1 with t. = 49 d in surface sediment 0–6 cm depth, k = –0.0009 d–1 with t. = 770 d in sub-surface sediment 24–34 cm depth from Trumpet Creeper East Pond, and k = –0.0149 d–1 with t. = 47 d in surface sediment 0–6 cm depth, k = –0.0000 d–1 with t. = 70 d in sub-surface sediment 24–34 cm depth from Trumpet Creeper North, Kiawah island (Smalling & Aelion 2004) 50–60% degradation in 35–100 d by anaerobic mixed culture microorganisms with atrazine as sole carbon source (Ghosh & Philip 2004) Biotransformation: Bioconcentration, Uptake (k1) and Elimination (k2) Rate Constants: © 2006 by Taylor & Francis Group, LLC Herbicides 3477 k2 = 0.0248, 1.26 h–1 (algae, daphnids, Ellgehausen et al. 1980) k2 = 27.2 d–1 (catfish, Ellgehausen et al. 1980) k1 = 2.4, 30, 19.0 h–1 (zebrafish: egg, yolk sac fry, juvenile; Gorge & Nagel 1990) k1 = 227.0 h–1; k2 = 2.354 h–1 (algae Scenedesmus acutus, Wang et al. 1996) k1 = 0.412 h–1; k2 = 0.073 h–1 (catfish Ictalurus melas, Wang et al. 1996) k1 = 2.027 h–1; k2 = 1.161 h–1 (water flea Daphnia magna, Wang et al. 1996) Half-Lives in the Environment: Air: t. = 2.6 h, based on estimated rate constant k = 147.2 . 10–12 cm3 molecule–1 s–1 at 25°C for the vaporphase reaction with hydroxyl radical in air (Atkinson 1987; quoted, Howard 1991). Surface water: estimated t. ~ 3.21 d in aqueous solution from river die-away tests (Furmidge & Osgerby 1967; quoted, Scow 1982); t. = 1–4 wk in estuarine systems (Jones et al. 1982; quoted, Meakins et al. 1994); under laboratory conditions in distilled water and river water was completely degraded after 21.3 and 7.3 h, respectively (Mansour et al. 1989; quoted, Montgomery 1993); t. = 3.2 d to 7–8 months in aquatic environments (Eisler 1985; quoted, Day 1991); measured rate constant k = (24 ± 4) M–1 s–1 at pH 4.0, k = (13 ± 1) M–1 s–1 at pH 4.2, for direct reaction with ozone in water at 26 and 21°C, respectively, with t. = 1.5 h at pH 7 (Yao & Haag 1991);. t. = 35.6–168 h in surface water system of a small stream in Iowa by water quality analyses (Kolpin & Kalkhoff 1993); t. = 235 d at 6°C, t. = 164 d at 22°C in darkness, t. = 59 d under sunlight conditions for river water at pH 17.3; t. = 130 d at 22°C in darkness for filtered river water at pH 7.3 and t. = 200 d at 22°C in darkness, t. = 169 d under sunlight conditions for seawater, pH 8.1 (Lartiges & Garrigues 1995) Groundwater: t. = 6–15 months for 0.72–10 µg mL–1 to biodegrade slowly at 25°C (Weidener 1974; quoted, Muir 1991) reported half-lives or persistence, t. = 60–150, 71, 74, and 130 d (Bottoni & Funari 1992) Sediment: t. = 145 d in a Wisconsin Lake sediment (Armstrong et al. 1967; quoted, Jones et al. 1982; Means et al. 1983) and t. ~ 30 d for Chesapeake Bay sediment (Ballantine et al. 1978; quoted, Jones et al. 1982); t. = 7–28 d for 0.1 µg mL–1 to rapid degrade in both aerobic and low oxygen systems in estuarine sediment/water at 12–35°C (Jones et al. 1982, quoted, Muir 1991); t.(aerobic) > 35 d for 0.1–1.0 µg mL–1 to slowly biodegrade in sediment/water at 25°C (Wolf & Jackson 1982; quoted, Muir 1991) t. = 60–120 d in surface sediment, t. = 60–223 d in subsurface sediment biodegradation t. = 47–128 d in the surface and t. = 70–770 in subsurface sediment (Smalling & Aelion 2004) Soil: half-lives in aqueous buffered solutions in soil at 25°C and pH 1, 2, 3, 4, 11, 12, and 13 were reported to be 3.3, 14, 58, 240, 100, 12.5, and 1.5 d, respectively (Armstrong et al. 1967; quoted, Montgomery 1993); t. = 3–5 yr in agricultural soils (Armstrong et al. 1967; quoted, Jones et al. 1982); estimated persistence of 10 months in soil (Kearney et al. 1969; quoted, Jury et al. 1987a); t. = 1.73, and 244 d at 25°C and pH 4 with and without fulvic acid (2%) (Li & Felbeck 1972; quoted, Montgomery 1993); persistence of 10 months in soil (Edwards 1973; quoted, Morrill et al. 1982); t. = 6.0 months at 15°C and t. = 2.0 months at 30°C in soils (Freed & Haque 1973); persistence of 12 months (Wauchope 1978); correlated t. = 37 d at pH 5.1–7.0, and t. = 28 d at pH 7.7–8.2 (Boddington Barn soil, Hance 1979), t. ~ 30 d at pH 4.6–5.3 and t. = 40 d at pH 6.3–8.0 (Triangle soil, Hance 1979); t. = 37 d in agricultural soils (Dao et al. 1979; quoted, Jones et al. 1982); estimated first-order t. = 36.5 d from biodegradation rate constant k = 0.019 d–1 by soil incubation die-away studies (Rao & Davidson 1980; quoted, Scow 1982); t. = 53 and 113 d at pH 6.5 at 22°C in a Hatzenbuhl soil at pH 4.8 and Neuhofen soil, respectively (Burkhard & Guth 1981; quoted, Montgomery 1993); t. = 1–6 months (Jones et al. 1982; quoted, Meakins et al. 1994); moderately persistent in soils with t. = 20–100 d (Willis & McDowell 1982); biodegradation t. = 71 d from screening model calculations (Jury et al. 1984; 1987a,b; Jury & Ghodrati 1989); © 2006 by Taylor & Francis Group, LLC 3478 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals t. ~ 6–10 wk (Hartley & Kidd 1987; quoted, Montgomery 1993); field t. = 4 wk by using lysimeters (Bowman 1990); half-lives from soil surfaces: t. = 655 to > 1000 d in peat soil and t. = 143–939 d in sandy soil at 20 ± 1°C (Dorfler et al. 1991); degradation rate constant k = (1.20 ± 0.097) . 10–2 d–1 with t. = 57.8 d in control soil and k = (1.01 ± 0.034) . 10–2 d–1 with t. = 68.6 d in pretreated soil once only in the laboratory (Walker & Welch 1991); t. ~ 21 d based on extractable residues in microcosm studies, compared to t. = 14 d in surface field soil (Winkelmann & Klaine 1991); selected field t. = 60 d (Wauchope et al. 1992; quoted, Dowd et al. 1993; Richards & Baker 1993; Hornsby et al. 1996); soil t. = 130 d (quoted, Pait et al. 1992); field t. = 35–50 d in soil and water but may be longer under cold or dry conditions; t. = 105 to > 200 d under groundwater conditions, depending on test system (Wood et al. 1991; quoted, Tomlin 1994); reported t. = 60–150 d, 71 d, 74 d and 130 d (Bottoni & Funari 1992); first-order k = –0.017 to –0.003 d–1 with corresponding t. = 41 d in the 0- to 30-cm soil to t. = 231 d in the 90 to 120-cm soil in Ames, Iowa (Kruger et al. 1993); dissipation t. = 71 d from soil surface (Gish et al. 1995); t. = 60 d (selected, Halfon et al. 1996). t. = 60 d (Gao et al. 1997) Biota: t. = 0.03 h in algae, t. = 1.52 d in catfish and t. = 9.5 h in daphnids (Ellgehausen et al. 1980); biochemical t. = 64 d from screening model calculations (Jury et al. 1987b); t. = 25.6 d in bean, t. = 24.3 d in turnips and t. = 14.6 d in oats at 20 ± 1°C from plant surfaces (Dorfler et al. 1991). TABLE 17.1.1.4.1 Reported vapor pressures of atrazine at various temperatures and the coefficients for the vapor pressure equations log P = A – B/(T/K) (1) ln P = A – B/(T/K) (1a) log P = A – B/(C + t/°C) (2) ln P = A – B/(C + t/°C) (2a) log P = A – B/(C + T/K) (3) log P = A – B/(T/K) – C·log (T/K) (4) Friedrich & Stammbach 1964 Grayson & Fosbracey 1982 Rordorf 1989 Goodman 1997 gas saturation-GC gas saturation-GC gas saturation-GC Knudsen effusion method t/°C P/Pa t/°C P/Pa t/°C P/Pa t/°C P/Pa 20 4.0 . 10–5 51.0 0.0040 25 3.9 . 10–5 40 6.7 . 10–4 extrapolated 55.5 0.0048 50 1.9 . 10–3 50 2.2 . 10–3 measured range 50–130°C 63.0 0.0095 75 0.056 60 9.5 . 10–3 Antoine eq. 66.0 0.0337 100 1.0 70 0.030 eq. 1 P/mmHg 66.7 0.023 125 13.0 80 0.098 A 13.766 76.5 0.0713 B 5945 81.5 0.117 eq. 1 PS/Pa eq. 1 P/Pa 20 3.7 . 10–5 A 17.583 A 16.08 B 6558.5 B 6040 eq. 1a P/Pa for temp range 40–125°C A 36.80 B 13.778 liquid eq. 1 PL/Pa A 13.2701 B 4626.79 © 2006 by Taylor & Francis Group, LLC Herbicides 3479 FIGURE 17.1.1.4.1 Logarithm of vapor pressure versus reciprocal temperature for atrazine. Atrazine: vapor pressure vs. 1/T -5.0 -4.0 -3.0 -2.0 -1.0 0.0 1.0 2.0 3.0 0.0022 0.0024 0.0026 0.0028 0.003 0.0032 0.0034 0.0036 1/(T/K) P( gol S ) aP/ Grayson & Fosbracey 1982 Rordorf 1989 Goodman 1997 Friedrich & Stammbach 1964 (50 to 130 °C) Friedrich & Stammbach 1964 (extrapolated) m.p. = 173 °C © 2006 by Taylor & Francis Group, LLC 3480 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals 17.1.1.5 Barban Common Name: Barban Synonym: Barbamate, Barbane, Carbine, Carbyne, CBN, Chlorinat Chemical Name: carbamic acid, (3-chlorophenyl)-, 4-chloro-2-butynyl ester; 4-chlorobut-2-ynyl 3-chloro-carbanilate; 4-chloro-2-butynyl 3-chlorophenylcarbamate Uses: herbicide for post-emergence control of wild oats in wheat, barley, broad beans, field beans, soybeans, peas, sugar beet, flax, lucerne, lentils, mustard, oilseed rape, sunflowers, etc. CAS Registry No: 101-27-9 Molecular Formula: C11H9Cl2NO2 Molecular Weight: 258.101 Melting Point (°C): 75 (Khan 1980; Herbicide Handbook 1989; Lide 2003) Boiling Point (°C): Density (g/cm3 at 20°C): 1.403 (25°C, Hartley & Kidd 1987) Molar Volume (cm3/mol): 262.8 (calculated-Le Bas method at normal boiling point, this work) Dissociation Constant pKa: Enthalpy of Vaporization, .HV (kJ/mol): 109.1 (Rordorf 1989) Enthalpy of Fusion, .Hfus (kJ/mol): 26.8 (Rordorf 1989) Entropy of Fusion, .Sfus (J/mol K): Fugacity Ratio at 25°C (assuming .Sfus = 56 J/mol K), F: 0.323 (mp at 75°C) Water Solubility (g/m3 or mg/L at 25°C or as indicated): 15.0 (Swezey & Nex 1961) 11.0 (20°C, Weber 1972; Worthing & Walker 1987) 11.0 (Martin & Worthing 1977; Ashton & Crafts 1981; Hartley & Kidd 1987; Worthing & Walker 1987; Herbicide Handbook 1989, Budavari 1989; Milne 1995) 11.0 (20–25°C, selected, Augustijn-Beckers et al. 1994; Hornsby et al. 1996) Vapor Pressure (Pa at 25°C or as indicated and reported temperature dependence equations): 1.33 . 10–3 (20°C, Weber 1972; Worthing & Walker 1987) 5.00 . 10–5 (Hartley & Kidd 1987) 1.60 . 10–4 (Worthing & Walker 1987) 5.05 . 10–5 (Herbicide Handbook 1989) 3.50 . 10–5, 1.0 . 10–3, 0.019, 0.240, 2.20 (25, 50, 70, 100, 125°C, gas saturation-GC, Rordorf 1989) log (PL/Pa) = 14.669 – 5703.8/(T/K); measured range 72–150°C (gas saturation-GC, Rordorf 1989) 5.07 . 10–5 (20–25°C, selected, Augustijn-Beckers et al. 1994; Hornsby et al. 1996) Henry’s Law Constant (Pa·m3/mol at 25°C or as indicated): 0.00117 (20°C, calculated-P/C, Muir 1991) 1.17 (calculated-P/C as per Worthing & Walker 1987, Majewski & Capel 1995) 0.00117 (calculated-P/C, this work) HN O O Cl Cl © 2006 by Taylor & Francis Group, LLC Herbicides 3481 Octanol/Water Partition Coefficient, log KOW: 2.68 (selected, Gerstl & Helling 1987) Bioconcentration Factor, log BCF: 2.20 (calculated-S, Kenaga 1980) Sorption Partition Coefficient, log KOC at 25°C or as indicated: 3.06 (soil, calculated-S, Kenaga 1980) 2.66 (calculated-MCI ., Gerstl & Helling 1987) 3.00 (20–25°C, estimated, Augustijn-Beckers et al. 1994; Hornsby et al. 1996) Environmental Fate Rate Constants, k, or Half-Lives, t.: Volatilization: estimated t. = 6690 d from 1 m depth of water at 20°C (Muir 1991). Photolysis: t. = 2.25 h for 22–99% of 10 µg/ml to degrade in distilled water under 300 nm light (Tanaka et al. 1981; quoted, Cessna & Muir 1991). Oxidation: Hydrolysis: Biodegradation: Biotransformation: Bioconcentration, Uptake (k1) and Elimination (k2) Rate Constants: Half-Lives in the Environment: Soil: estimated persistence of 2 months (Kearney et al. 1969; quoted, Jury et al. 1987); persistence of 2 weeks in soil (Edwards 1973; quoted, Morrill et al. 1982); persistence of about 3 weeks in soil (Herbicide Handbook 1989); selected field t. = 5 d (Augustijn-Beckers et al. 1994; Hornsby et al. 1996). © 2006 by Taylor & Francis Group, LLC 3482 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals 17.1.1.6 Benefin Common Name: Benefin Synonym: Balan, Bonalan, benfluralin Chemical Name: N-butyl-N-ethyl-.,.,.-trifluoro-2,6-dinitro-p-toluidine Uses: as pre-emergence herbicide for the control of annual grasses and broadleaf weeds in chicory, cucumbers, endive, groundnuts, lettuce, lucerne, and other foliage crops. CAS Registry No: 1861-40-1 Molecular Formula: C13H16F3N3O4 Molecular Weight: 335.279 Melting Point (°C): 66 (Lide 2003) Boiling Point (°C): 121–122 (0.5 mmHg), 148–149 at 7 mmHg (Tomlin 1994) Density (g/cm3 at 20°C): 1.28 (tech., Tomlin 1994) Molar Volume (cm3/mol): 295.9 (calculated-Le Bas method at normal boiling point) Dissociation Constant pKa: Enthalpy of Fusion, .Hfus (kJ/mol): 38.70 (DSC method, Plato & Glasgow 1969) Entropy of Fusion, .Sfus (J/mol K): Fugacity Ratio at 25°C (assuming .Sfus = 56 J/mol K), F: 0.396 (mp at 66°C) Water Solubility (g/m3 or mg/L at 25°C or as indicated): < 1.0 (Ashton & Crafts 1973) 0.50 (Weber et al. 1980) 1.0 (20°C, selected, Suntio et al. 1988) 0.10 (Herbicide Handbook 1983; Tomlin 1994) 0.10 (20–25°C, selected, Hornsby et al. 1996) Vapor Pressure (Pa at 25°C or as indicated): 0.00519 (30°C, Ashton & Crafts 1973) 0.0104 (Herbicide Handbook 1983) 0.0040 (20°C, estimated, Suntio et al. 1988) 0.0087 (Tomlin 1994) 0.0088 (20–25°C, selected, Hornsby et al. 1996) Henry’s Law Constant (Pa·m3/mol at 25°C or as indicated): 1.34 (20°C, calculated-P/C, Suntio et al. 1988) Octanol/Water Partition Coefficient, log KOW: 5.34 (selected, Magee 1991) 5.29 (20°C, pH 7, Tomlin 1994) 5.29 (pH 7, selected, Hansch et al. 1995) Bioconcentration Factor, log BCF: 3.36 (calculated-S per Kenaga 1980, this work) N NO2 O2N F F F © 2006 by Taylor & Francis Group, LLC Herbicides 3483 Sorption Partition Coefficient, log KOC: 4.03 (quoted exptl., Sabljic 1987) 4.03, 3.75 (quoted, estimated; Magee 1991) 3.95 (soil, Hornsby et al. 1996) 2.96 (2.59–3.33) (soil: organic carbon OC . 0.5%, average, Delle Site 2001) Environmental Fate Rate Constants, k, or Half-Lives, t.: Volatilization: Photolysis: atmospheric and aqueous photolysis half-lives were estimated to be 288–864 h (Howard et al. 1991). Oxidation: photooxidation t. ~ 0.782–7.82 h based on reaction with OH radicals in air (Howard et al. 1991). Hydrolysis: no hydrolyzable group (Howard et al. 1991). Biodegradation: aerobic t. ~ 504–2880 h in soil, and anaerobic soil t. = 144–480 h (Howard et al. 1991). Biotransformation: Bioconcentration, Uptake (k1) and Elimination (k2) Rate Constants: Half-Lives in the Environment: Air: t. = 0.782–7.82 h based on estimated reaction with OH radicals in the gas-phase (Howard et al. 1991). Surface water: t. = 288–864 h based on observed photolysis by sunlight (Howard et al. 1991). Groundwater: t. = 144–5760 h based on unacclimated aqueous aerobic and anaerobic biodegradation half-lives (Howard et al. 1991). Sediment: Soil: t. = 504–2880 h based on aerobic solid die-away test data (Howard et al. 1991); field t. = 40 d (Hornsby et al. 1996). Biota: © 2006 by Taylor & Francis Group, LLC 3484 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals 17.1.1.7 Bifenox Common Name: Bifenox Synonym: MC-4379, Modown Chemical Name: benzoic acid, 5-(2,4-dichlorophenoxy)-2-nitro-, methyl ester; methyl-5-(2,4-dichlorophenoxy)-2- nitrobenzoate Uses: selective pre-emergence and post-emergence herbicide to effectively control a wide variety of broadleaf weeds in corn, grain, sorghum, maize, rice, and soybeans. CAS Registry No: 42576-02-3 Molecular Formula: C14H9Cl2NO5 Molecular Weight: 342.131 Melting Point (°C): 85 (Lide 2003) Boiling Point (°C): Density (g/cm3 at 20°C): 1.155 (Ashton & Crafts 1981; Herbicide Handbook 1989; Montgomery 1993) Molar Volume (cm3/mol): 305.5 (calculated-Le Bas method at normal boiling point) Dissociation Constant pKa: Enthalpy of Vaporization, .HV (kJ/mol): 90.5 (Rordorf 1989) Enthalpy of Fusion, .Hfus (kJ/mol): 26.4 (Rordorf 1989) Entropy of Fusion, .Sfus (J/mol K): 74.0 (Rordorf 1989) Fugacity Ratio at 25°C (assuming .Sfus = 56 J/mol K), F: 0.258 (mp at 85°C) Water Solubility (g/m3 or mg/L at 25°C or as indicated): 0.35 (20°C, Weber 1972; Worthing & Walker 1987) 0.35 (Martin & Worthing 1977; Herbicide Handbook 1978) 0.35 (Ashton & Crafts 1981; Herbicide Handbook 1989; Budavari 1989) 0.35 (30°C, Worthing & Walker 1987) 0.35 (Hartley & Kidd 1987; Worthing & Hance 1991; Montgomery 1993; Tomlin 1994; Milne 1995) 0.398 (20–25°C, selected, Wauchope et al. 1992; Lohninger 1994; Hornsby et al. 1996) Vapor Pressure (Pa at 25°C or as indicated and reported temperature dependence equations): 0.00032 (20°C, Weber 1972; Worthing & Walker 1987) 0.00032 (30°C, Ashton & Crafts 1981; Worthing & Hance 1991; Tomlin 1994) 0.00032 (30°C, Hartley & KIdd 1987; Budavari 1989; Montgomery 1993) 5.40 . 10–6, 2.0 . 10–4, 4.40 . 10–3, 0.064, 0.67 (25, 50, 70, 100, 125°C, gas saturation-GC, Rordorf 1989) log (PS/Pa) = 14.996 – 6040.4/(T/K); measured range 36.9–85.5°C (solid, gas saturation-GC, Rordorf 1989) log (PL/Pa) = 13.815 – 5582.5/(T/K); measured range 90.5–175°C (liquid, gas saturation-GC, Rordorf 1989) 0.00032 (20–25°C, selected, Wauchope et al. 1992; Hornsby et al. 1996) Henry’s Law Constant (Pa·m3/mol at 25°C or as indicated): 0.321 (20°C, calculated-P/C, Muir 1991) 0.011 (calculated-P/C, Montgomery 1993) 0.313 (calculated-P/C, this work) O Cl Cl NO2 O O © 2006 by Taylor & Francis Group, LLC Herbicides 3485 Octanol/Water Partition Coefficient, log KOW: 5.63 (selected, Dao et al. 1983) 4.50 (Worthing & Hance 1991) 4.48 (Montgomery 1993; Tomlin 1994) 4.48 (selected, Hansch et al. 1995) 5.24 (RP-HPLC-RT correlation using short ODP column, Donovan & Pescatore 2002) Bioconcentration Factor, log BCF: 2.30 (static water, Metcalf & Sanborn 1975; quoted, Kenaga & Goring 1980; Isensee 1991) 3.05 (calculated-S, Kenaga 1980; quoted, Isensee 1991) Sorption Partition Coefficient, log KOC: 3.89 (soil, calculated per Kenaga & Goring, Kenaga 1980) 4.0 (soil, 20–25°C, estimated, Wauchope et al. 1992; Hornsby et al. 1996) 2.24–4.39 (Montgomery 1993) 4.0 (estimated-chemical structure, Lohninger 1994) 2.70–4.36 (Tomlin 1994) Environmental Fate Rate Constants, k, or Half-Lives, t.: Volatilization: estimated t. = 29.8 d from 1 m depth of water at 30°C (Muir 1991). Photolysis: with < 5% degradation by UV light of 290–400 nm in 48 h (Worthing & Hance 1991). Oxidation: Hydrolysis: stable in aqueous solution at pH 5.0–7.3 but rapidly hydrolyzed at pH 9.0 both at 22°C (Worthing & Hance 1991). Biodegradation: t. = 2–5 d for 10 µg/mL to biodegrade in flooded soil at 30°C (Ohyama & Kuwatsuka 1978; quoted, Muir 1991). Biotransformation: Bioconcentration, Uptake (k1) and Elimination (k2) Rate Constants: Half-Lives in the Environment: Soil: t. = 2–5 d for 10 µg/ml to biodegrade in flooded soil at 30°C (Ohyama & Kuwatsuka 1978; quoted, Muir 1991); average t. = 7–14 d in soils (Hartley & Kidd 1987; Herbicide Handbook 1989; quoted, Montgomery 1993); selected field t. = 7.0 d (Wauchope et al. 1992; Hornsby et al. 1996); average t. = 7–14 d (Herbicide Handbook 1989); t. ~ 5–7 d in soil (Tomlin 1994). © 2006 by Taylor & Francis Group, LLC 3486 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals 17.1.1.8 Bromacil Common Name: Bromacil Synonym: Borea, Bromax, Bromazil, Cynogan, Hyvar, Hyvarex, Krovar I or II, Nalkil, Uragan, Urox B, Uron HX, Weed Blast Chemical Name: 5-bromo-3-sec-butyl-6-methyluracil; 5-bromo-6-methyl-3-(1-methylpropyl)-2,4-(1H,3H)pyrimidinedione Uses: Herbicide applied to soil to control annual and perennial grasses, broadleaf weeds, and general vegetation on uncropped land; also used for selective weed control in apple, asparagus, cane fruit, hops, and citrus crops. CAS Registry No: 314-40-9 Molecular Formula: C9H13BrN2O2 Molecular Weight: 261.115 Melting Point (°C): 158 (Lide 2003) Boiling Point (°C): Density (g/cm3 at 20°C): 1.55 (25°C, Hartley & Kidd 1987; Herbicide Handbook 1989; Worthing & Hance 1991; Montgomery 1993) 1.59 (23°C, Tomlin 1994) 1.55 (Milne 1995) Molar Volume (cm3/mol): 193.1 (calculated-Le Bas method at normal boiling point) Dissociation Constant pKa: 9.10 (Wauchope et al. 1992; Hornsby et al. 1996) < 7.0 (Montgomery 1993) 9.27 (Tomlin 1994) Enthalpy of Fusion, .Hfus (kJ/mol): Entropy of Fusion, .Sfus (J/mol K): Fugacity Ratio at 25°C (assuming .Sfus = 56 J/mol K), F: 0.0496 (mp at 158°C) Water Solubility (g/m3 or mg/L at 25°C or as indicated): 815 (Bailey & White 1965; Khan 1980; Hartley & Kidd 1987; Montgomery 1993; Milne 1995) 815 (Melnikov 1971; Spencer 1973; Herbicide Handbook 1978; Herbicide Handbook 1989) 815 (20°C, Weber 1972; Worthing & Walker 1987, Worthing & Hance 1991) 820 (Beste & Humburg 1983; Jury et al. 1983) 1064 (shake flask-GC or LSC, Gerstl & Mingelgrin 1984; Gerstl & Helling 1987) 626, 775, 1043 (4, 25, 40°C, shake flask-LSS, Madhun et al. 1986) 700 (20–25°C, selected, Wauchope et al. 1992; Lohninger 1994; Hornsby et al. 1996) 700, 807, 1287 (at pH 7, 5, 9, Tomlin 1994) Vapor Pressure (Pa at 25°C or as indicated): 5 . 10–5 (20°C, Weber 1972; Worthing & Walker 1987) 3 . 10–5 (estimated, USEPA 1975) 0.107 (100°C, Khan 1980) 2.9 . 10–5 (Jury et al. 1983) 0.00033 (Hartley & Kidd 1987; Worthing & Hance 1991) 4 . 10–5 (20–25°C, selected, Wauchope et al. 1992) 3.3 . 10–5 (Montgomery 1993) NH N O O Br © 2006 by Taylor & Francis Group, LLC Herbicides 3487 Henry’s Law Constant (Pa·m3/mol at 25°C at 25°C or as indicated): 9.17 . 10–6 (Beste & Humburg 1983; Jury et al. 1983) 9.17 . 10–5 (calculated-P/C, Jury et al. 1984, 1987a; Jury & Ghodrati 1989) 0.0019 (20°C, selected, Suntio et al. 1988) 1.06 . 10–5 (20°C, calculated-P/C, Muir 1991) 1.06 . 10–5 (calculated-P/C, Montgomery 1993) Octanol/Water Partition Coefficient, log KOW: 2.02 (Rao & Davidson 1980) 1.33 (selected, Dao et al. 1983) 1.84 (shake flask-GC or LSC, Gerstl & Mingelgrin 1984) 1.84, 1.87, 1.90 (4, 25, 40°C, shake flask-LSS, Madhun et al. 1986) 1.85 (selected, Gerstl & Helling 1987) 2.11 selected, Magee 1991; Devillers et al. 1996) 1.84–2.04 (Montgomery 1993) 2.11 (selected, Sangster 1993) 1.87, 1.88, 1.63 (at pH 7, 5, 9, Tomlin 1994) 2.11 (recommended, Hansch et al. 1995) Bioconcentration Factor, log BCF: 0.505 (measured, Kenaga 1980) 2.27 (calculated-S, Kenaga 1980) 0.477 (calculated-KOC, Kenaga 1980) 0.51 (Pimephales promelas, Call et al. 1987) Sorption Partition Coefficient, log KOC at 25°C or as indicated: 1.86 (soil, Hamaker & Thompson 1972) 3.13 (soil, calculated as per Kenaga & Goring 1980, Kenaga 1980) 1.86 (Rao & Davidson 1980) 2.33, 1.34, 1.63 (estimated-S, calculated-S and mp, calculated-KOW, Karickhoff 1981) 1.61 (sediments average-Freundlich adsorption, Corwin & Farmer 1984) 1.41–2.46 (California lake sediments, Corwin & Farmer 1984) 1.98, 1.88 (4, 25°C, Semiahmoo soil, in µmol/kg OC, batch equilibrium method-LSS, Madhun et al. 1986) 2.11, 1.88 (4, 25°C, Adkins soil, in µmol/kg OC, Madhun et al. 1986) 1.90, 1.66, 1.75; 1.86, 1.89, 1.34 (estimated-KOW; S, Madhum et al. 1986) 1.53, 2.73 (quoted, calculated-MCI ., Gerstl & Helling 1987) 1.86 (soil, screening model calculations, Jury et al. 1987a,b; Jury & Ghodrati 1989; Carsel 1989) 2.56 (calculated-MCI ., Bahnick & Doucette 1988) 1.86, 1.80 (reported, estimated as log KOM, Magee 1991) 1.53, 1.86, 3.13 (soil, quoted values, Bottoni & Funari 1992) 1.51 (soil, 20–25°C, selected, Wauchope et al. 1992; Hornsby et al. 1996) 1.51 (Montgomery 1993) 2.09 (estimated-chemical structure, Lohninger 1994) 1.60 (quoted or calculated-QSAR MCI 1., Sabljic et al. 1995) 1.43, 1.72 (average values for sediments, soils, Delle Site 2001) 1.48, 1.46, 1.53 (soils: organic carbon OC . 0.1%, OC . 0.5%, 0.1 . OC < 0.5%, and pH 6.3–7.9, average, Delle Site 2001) 1.80, 1.72 (soils: organic carbon OC . 0.1%, OC . 0.5%, and pH . 7.3 undissociated, average, Delle Site 2001) Environmental Fate Rate Constants, k, or Half-Lives, t.: Volatilization: estimated t. ~ 10,000 d from 1 m depth of water at 20°C (Muir 1991). Photolysis: 115 ppb contaminated water in the presence of TiO2 and H2O2 photodegraded to 6 ppb by 15 h solar irradiation with complete degradation after 75 h (Muszkat et al. 1992). Oxidation: Hydrolysis: © 2006 by Taylor & Francis Group, LLC 3488 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals Biodegradation: t. = 350 d for 100 d leaching and screening test in 0–10 cm depth of soil (Rao & Davidson 1980; quoted, Jury et al. 1983, 1984, 1987a). Biotransformation: Bioconcentration, Uptake (k1) and Elimination (k2) Rate Constants: Half-Lives in the Environment: Air: Surface water: Ground water: reported t. = 150–158 and 350 d (Bottoni & Funari 1992) Sediment: Soil: t. = 7.0 months at 15°C and t. = 4.5 months at 30°C in soils (Freed & Haque 1973); rate constant k = 0.0038 d–1 with biodegradation t. = 350 d under field conditions (Rao & Davidson 1980; quoted, Jury et al. 1984); t. = 350 d from screening model calculations (Jury et al. 1987a,b; Jury & Ghodrati 1989); t. > 100 d (Willis & McDowell 1982) t. ~ 5429–46200 d in loamy sand and peat at 25–35°C as follows (Madhum & Freed 1987): t. = 46200, 12391, and 5856 d at 25, 30, and 35°C, respectively, at herbicide concn at 5 µg/kg, while t. = 18851, 9925, and 7588 d at 25, 30, and 35°C, respectively, at herbicide concn at 100 µg/kg in an Adkins loamy sand; however, the half-lives in peat. t. = 5429, 6789, and 8044 d at 25, 30, and 35°C, respectively, at herbicide concn at 5 µg/kg while t. = 6293, 5986, and 6784 d at 25, 30, and 35°C, respectively, at herbicide concn at 100 µg/kg in a Semiahoo mucky peat (Madhun & Freed 1987) selected field t. = 60 d (Wauchope et al. 1992; Hornsby et al. 1996); t. = 150–180d and 350 d (Bottoni & Funari 1992). Biota: biochemical t. = 350 d from screening model calculations (Jury et al. 1987a,b; Jury & Ghodrati 1989). © 2006 by Taylor & Francis Group, LLC Herbicides 3489 17.1.1.9 Bromoxynil Common Name: Bromoxynil Synonym: Brittox, Brominal, Brominex, Brominil, Broxynil, Buctril, Chipco crab-kleen, ENT 20852, Nu-lawn weeder, Oxytril M, Partner Chemical Name: 3,5-dibromo-4-hydroxybenzonitrile; 4-cyano-2,6-dibromophenol Uses: herbicide for post-emergence control of annual broadleaf weeds and it is often used in combination with other herbicides to extend the spectrum of control. CAS Registry No: 1689-84-5 Molecular Formula: C7H3Br2NO Molecular Weight: 276.913 Melting Point (°C): 190 (Khan 1980; Herbicide Handbook 1989; Montgomery 1993; Lide 2003) Boiling Point (°C): Density (g/cm3 at 20°C): Molar Volume (cm3/mol): 176.7 (calculated-Le Bas method at normal boiling point, this work) Dissociation Constant pKa: 4.20 (radiometer/pH meter, Cessna & Grover 1978) 4.06 (Herbicide Handbook 1989; Montgomery 1993) 4.06 (Budavari 1989; Worthing & Hance 1991) 3.86 (Tomlin 1994) Enthalpy of Fusion, .Hfus (kJ/mol): 31.80 (DSC method, Plato 1972) Entropy of Fusion, .Sfus (J/mol K): Fugacity Ratio at 25°C (assuming .Sfus = 56 J/mol K), F: 0.0241 (mp at 190°C) Water Solubility (g/m3 or mg/L at 25°C or as indicated): 130 (20–25°C, Spencer 1973) 131 (Kenaga 1980) < 200 (Khan 1980) 130 (20–25°C, Ashton & Crafts 1981) 130 (Hartley & Kidd 1987; Montgomery 1993; Tomlin 1994; Milne 1995) 130 (Worthing & Walker 1987, Worthing & Hance 1991) 130 (20–25°C, Herbicide Handbook 1989) Vapor Pressure (Pa at 25°C or as indicated): < 0.0010 (20°C, Hartley & Kidd 1987; Tomlin 1994) 0.00064 (Herbicide Handbook 1989) 0.00064 (Montgomery 1993) Henry’s Law Constant (Pa·m3/mol at 25°C or as indicated): 0.14180 (20–25°C, calculated-P/C, Montgomery 1993) 1.36 . 10–3 (calculated-P/C, this work) Octanol/Water Partition Coefficient, log KOW: 2.60 (selected, Dao et al. 1983) OH Br Br N © 2006 by Taylor & Francis Group, LLC 3490 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals < 2.00 (Herbicide Handbook 1989) < 2.00 (Montgomery 1993) Bioconcentration Factor, log BCF: 1.60 (calculated, Kenaga 1980) Sorption Partition Coefficient, log KOC: 2.48 (soil, quoted from Kenaga 1980, Bottoni & Funari 1992) 2.48 (calculated, Montgomery 1993) 2.86, 3.06 (soil, quoted exptl.; estimated-general model using molecular descriptors, Gramatica et al. 2000) Environmental Fate Rate Constants, k or Half-Lives, t.: Volatilization: Photolysis: rate constant of degradation in water, k = 1.04 . 10–3 s–1 at pH 8.3 and k = 1.08 . 10–3 s–1 at pH 11.6 (Kochany 1992). Oxidation: Hydrolysis: Biodegradation: t. . 24 h for 0.03 µg/mL to biodegrade in runoff water at 20–25°C (Brown et al. 1984; quoted, Muir 1991). Biotransformation: Bioconcentration, Uptake (k1) and Elimination (k2) Rate Constants: Half-Lives in the Environment: Air: Surface water: t. . 24 h for 0.03 µg mL–1 to biodegrade in runoff water at 20–25°C (Brown et al. 1984; quoted, Muir 1991). Ground water: reported t. = 10 d (Bottoni & Funari 1992) Sediment: Soil: t. ~ 10 d in soil (Hartley & Kidd 1987; Worthing & Hance 1991; quoted, Bottoni & Funari 1992; Montgomery 1993; Tomlin 1994);. Biota: © 2006 by Taylor & Francis Group, LLC Herbicides 3491 17.1.1.10 sec-Bumeton Common Name: sec-Bumeton Synonym: etazine, GS14254, secbumeton Chemical Name: N-ethyl-6-methoxy-N.-(1-methylpropyl)-1,3,5-triazine-2,4-diamine CAS Registry No: 26259-45-0 Uses: herbicide Molecular Formula: C10H19N5O Molecular Weight: 225.291 Melting Point (°C): 87 (Lide 2003) Boiling Point (°C): Density (g/cm3 at 20°C): 1.105 (Hartley & Kidd 1987; Worthing & Walker 1987) Molar Volume (cm3/mol): Dissociation Constant pKa: 4.4 (Worthing 1987) 4.4, 4.36 (Augustijn-Beckers et al. 1994; Hornsby et al. 1996) Enthalpy of Fusion, .Hfus (kJ/mol): Entropy of Fusion, .Sfus (J/mol K): Fugacity Ratio at 25°C (assuming .Sfus = 56 J/mol K), F: 0.246 (mp at 87°C) Water Solubility (g/m3 or mg/L at 25°C or as indicated): 620 (quoted, Kenaga & Goring 1980) 620 (Ashton & Crafts 1981) 600 (20°C, Hartley & Kidd 1987; Worthing & Walker 1987) 600 (20–25°C, selected, Augustijn-Beckers et al. 1994; Hornsby et al. 1996) Vapor Pressure (Pa at 25°C or as indicated): 9.7 . 10–4 (20°C, Ashton & Crafts 1981; Worthing & Walker 1987) 9.71 . 10–4 (20°C, Hartley & Kidd 1987) 9.7 . 10–4 (20–25°C, selected, Augustijn-Beckers et al. 1994; Hornsby et al. 1996) Henry’s Law Constant (Pa·m3/mol): Octanol/Water Partition Coefficient, log KOW: 3.20 (LOGPSTAR or CLOGP data, Sabljic et al. 1995) Octanol/Air Partition Coefficient, log KOA: Bioconcentration Factor, log BCF or log KB: 1.20 (fish, Kenaga 1980b) Sorption Partition Coefficient, log KOC: 2.54 (soil, calculated, Kenaga & Goring 1980) 2.11 (soil, calculated, Kenaga 1980b) 2.18 (soil, pH 7, Augustijn-Beckers et al. 1994; Hornsby et al. 1996) 2.78; 2.29 (soil: quoted, calculated-MCI ., Meylan et al. 1992) 2.78 (soil, calculated-MCI ., Sabljic et al. 1995) N N N NH O HN © 2006 by Taylor & Francis Group, LLC 3492 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals 2.78; 2.78, 2.55 (soil, estimated-class-specific model, estimated-general model using molecular descriptors, Gramatica et al. 2000) Environmental Fate Rate Constants, k, or Half-Lives, t.: Hydrolysis: on hydrolysis at 20°C, t. ~ 30 d at pH 1, t. = 75 d at pH 13 (Worthing & Walker 1987). Half-Lives in the Environment: Air: Surface water: on hydrolysis at 20°C, t. ~ 30 d at pH 1, t. = 75 d at pH 13 (Worthing & Walker 1987). Ground water: Sediment: Soil: field t. ~ 60 d (estimated, Augustijn-Beckers et al. 1994; Hornsby et al. 1996). Biota: © 2006 by Taylor & Francis Group, LLC Herbicides 3493 17.1.1.11 Butachlor Common Name: Butachlor Synonym: Butanex, Butanox, CP 53619, Lambast, Machete, Pillarsete Chemical Name: N-butoxymethyl-2-chloro-2.6.-diethylacetanilide; N-(butoxymethyl)-2-chloro-N-(2,6-diethylphenyl)- acetamide Uses: herbicide for pre-emergence control of most annual grasses, some broadleaf weeds, and many aquatic weeds in both seeded and transplanted rice. CAS Registry No: 23184-66-9 Molecular Formula: C17H26ClNO2 Molecular Weight: 311.847 Melting Point (°C): < –5.0 (Hartley & Kidd 1987; Worthing & Hance 1991; Tomlin 1994; Milne 1995; Lide 2003) Boiling Point (°C): 156 (at 0.5 mmHg, Ashton & Crafts 1981; Herbicide Handbook 1989; Tomlin 1994; Milne 1995) Density (g/cm3 at 20°C): 1.07 (25°C, Ashton & Crafts 1981; Hartley & Kidd 1987; Herbicide Handbook 1989; Tomlin 1994; Milne 1995) Molar Volume (cm3/mol): 387.8 (calculated-Le Bas method at normal boiling point) Dissociation Constant pKa: Enthalpy of Fusion, .Hfus (kJ/mol): Entropy of Fusion, .Sfus (J/mol K): Fugacity Ratio at 25°C (assuming .Sfus = 56 J/mol K), F: 1.0 Water Solubility (g/m3 or mg/L at 25°C or as indicated): 23 (20°C, Weber 1972; Worthing 1987) 20 (Martin & Worthing 1977) 23 (24°C, Ashton & Crafts 1981; Herbicide Handbook 1989) 20 (20°C, Hartley & Kidd 1987; Tomlin 1994; Milne 1995) 23 (24°C, Worthing & Walker 1987, Worthing & Hance 1991) 23 (20–25°C, selected, Augustijn-Beckers et al. 1994; Hornsby et al. 1996) Vapor Pressure (Pa at 25°C or as indicated): 0.0007 (20°C, Weber 1972; Worthing & Walker 1987) 0.0006 (Ashton & Crafts 1981; Herbicide Handbook 1989) 0.0006 (Hartley & Kidd 1987; Worthing & Hance 1991; Tomlin 1994) 0.0006 (20–25°C, selected, Augustijn-Beckers et al. 1994; Hornsby et al. 1996) Henry’s Law Constant (Pa·m3/mol at 25°C or as indicated): 0.00817 (20°C, calculated-P/C, Muir 1991) 0.00814 (calculated-P/C, this work) Octanol/Water Partition Coefficient, log KOW: 4.50 (quoted and recommended, Hansch et al. 1995; quoted, Sabljic et al. 1995) Bioconcentration Factor, log BCF: 2.06 (calculated-S, Kenaga 1980) 1.03, 0.756 (18, 9 µg/L concn in water; carp, 3–5 d exposure, Wang et al. 1992) N O Cl O © 2006 by Taylor & Francis Group, LLC 3494 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals 0.38, 0.845 (10, 1 µg/L concn in water; tilapia, 3–5 d exposure, Wang et al. 1992) 0.447, 0.845 (10, 1 µg/L concn in water; loach, 3–5 d exposure, Wang et al. 1992) 1.76, 2.02 (2.5, 1.25 µg/L concn in water; grass carp, 3–5 d exposure, Wang et al. 1992) 1.71, 1.90 (5, 2.5 µg/L concn in water; eel, 3–5 d exposure, Wang et al. 1992) 1.99, 2.34 (2.4, 0.4 µg/L concn in water; black silver carp, 3–5 d exposure, Wang et al. 1992) 0.041, 0.778 (100, 10 µg/L concn in water; freshwater clam, 3–5 d exposure, Wang et al. 1992) Sorption Partition Coefficient, log KOC: 2.92 (calculated-solubility, Kenaga 1980) 2.85 (20–25°C, selected, Augustijn-Beckers et al. 1994; Hornsby et al. 1996) 2.86 (soil, calculated-MCI 1., Sabljic et al. 1995) Environmental Fate Rate Constants, k, or Half-Lives, t.: Volatilization: estimated t. ~ 1049 d from 1 m depth of water at 20°C (Muir 1991). Photolysis: t. = 0.8–5.4 h in distilled water (Chen et al. 1982; quoted, Cessna & Muir 1991). Oxidation: Hydrolysis: t. > 2.5 months for 2 µg/mL to hydrolyze in phosphate buffer at pH 6 and borate buffer at pH 9 both at 25°C (Chen & Chen 1979; quoted, Muir 1991). Biodegradation: Biotransformation: Bioconcentration, Uptake (k1) and Elimination (k2) Rate Constants: Half-Lives in the Environment: Soil: persists for 6–10 wk in soil (Hartley & Kidd 1987; Tomlin 1994); t. = 4 to 8 d depending upon soil type (Herbicide Handbook 1989); persists in soil 42–70 d (Worthing & Hance 1991); selected field t. = 12 d (Augustijn-Beckers et al. 1994; Hornsby et al. 1996). © 2006 by Taylor & Francis Group, LLC Herbicides 3495 17.1.1.12 Butralin Common Name: Butralin Synonym: Amex, Butalin, Rutralin, Sector, Tamex Chemical Name: N-sec-butyl-4-tert-butyl-2,6-dinitroaniline; 4-(1,1-dimethylethyl)-N-(1-methylpropyl)-2,6-dinitrobenzenamine Uses: herbicide for pre-emergence control of annual broadleaf weeds and grasses in cotton, beans, barley, rice, soybeans, alliums, vines, ornamentals and orchards of fruit and nut trees; also to control suckers on tobacco. CAS Registry No: 33629-47-9e Molecular Formula: C14H21N3O4 Molecular Weight: 295.335 Melting Point (°C): 60 (Lide 2003) Boiling Point (°C): 134–136 (at 0.5 mmHg, Hartley & Kidd 1987; Worthing & Hance 1991; Tomlin 1994; Milne 1995) Density (g/cm3 at 20°C): Molar Volume (cm3/mol): 313.6 (calculated-Le Bas method at normal boiling point) Dissociation Constant pKa: Enthalpy of Fusion, .Hfus (kJ/mol): Entropy of Fusion, .Sfus (J/mol K): Fugacity Ratio at 25°C (assuming .Sfus = 56 J/mol K), F: 0.454 (mp at 60°C) Water Solubility (g/m3 or mg/L at 25°C or as indicated): 1.0 (Herbicide Handbook 1978) 1.0 (Khan 1980) 10 (24°C, Ashton & Crafts 1981) 1.0 (24°C, Hartley & Kidd 1987; Tomlin 1994; Milne 1995) 1.0 (24–26°C, Worthing & Walker 1987, Worthing & Hance 1991) 1.0 (Budavari 1989) Vapor Pressure (Pa at 25°C): 0.002 (Ashton & Crafts 1981) 0.0017 (Hartley & Kidd 1987; Worthing & Hance 1991; Tomlin 1994) 0.0017 (Budavari 1989) Henry’s Law Constant (Pa·m3/mol at 25°C): 0.502 (calculated-P/C, this work) Octanol/Water Partition Coefficient, log KOW: 4.54 (selected, Dao et al. 1983) 5.16 (quoted LOGPSTAR or CLOGP data, Sabljic et al. 1995) Bioconcentration Factor, log BCF: 2.79 (calculated-S, Kenaga 1980; quoted, Isensee 1991) 2.80 (calculated-KOC, Kenaga 1980) HN NO2 O2N © 2006 by Taylor & Francis Group, LLC 3496 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals Sorption Partition Coefficient, log KOC: 3.64 (calculated, Kenaga & Goring 1980; quoted, Kenaga 1980) 3.91 (soil, Kenaga & Goring 1980; quoted, Sabljic 1987; Bahnick & Doucette 1988) 3.75 (calculated-MCI ., Bahnick & Doucette 1988) 3.98 (soil, calculated-MCI 1., Sabljic et al. 1995) 3.98; 3.38 (soil, quoted exptl.; estimated-general model using molecular descriptors, Gramatica et al. 2000) Environmental Fate Rate Constants, k, or Half-Lives, t.: Volatilization: Photolysis: t. = 8 h for 25% of 2000 µg/mL to degrade in methanol under sunlight (Plimmer & Klingebiel 1974; quoted, Cessna & Muir 1991). Oxidation: Hydrolysis: Biodegradation: t. = 24 d for 0.5 µg/mL to biodegrade in soil at 20–42°C (Savage 1978; quoted, Muir 1991). Biotransformation: Bioconcentration, Uptake (k1) and Elimination (k2) Rate Constants: Half-Lives in the Environment: Soil: t. = 24 d for 0.5 µg/mL to biodegrade in soil at 20–42°C (Savage 1978; quoted, Muir 1991). © 2006 by Taylor & Francis Group, LLC Herbicides 3497 17.1.1.13 Butylate Common Name: Butylate Synonym: Butilate, diisocarb, Genate, R 1910, Sutan Chemical Name: S-ethyldiisobutylthiocarbamate; S-ethyl-bis(2-methylpropylcarbamothioate Uses: herbicide to control annual grass weeds in maize, by pre-plant soil incorporation; also to control some broadleaf weeds. CAS Registry No: 2008-41-5 Molecular Formula: C11H23NOS Molecular Weight: 217.372 Melting Point (°C): liquid Boiling Point (°C): 137.5–138 (at 21 mmHg, Hartley & Kidd 1987; Worthing & Hance 1991; Tomlin 1994; Milne 1995) 71.0 (at 10 mmHg, Herbicide Handbook 1989) Density (g/cm3 at 20°C): 0.9402 (25°C, Hartley & Kidd 1987; Herbicide Handbook 1989; Worthing & Hance 1991; Tomlin 1994) 0.9417 (Milne 1995) Molar Volume (cm3/mol): 280.9 (calculated-Le Bas method at normal boiling point, Suntio et al. 1988) Dissociation Constant pKa: Enthalpy of Fusion, .Hfus (kJ/mol): Entropy of Fusion, .Sfus (J/mol K): Fugacity Ratio at 25°C (assuming .Sfus = 56 J/mol K), F: 1.0 Water Solubility (g/m3 or mg/L at 25°C or as indicated): 45.0 (Kenaga 1980; Weber et al. 1980) 45.0 (22°C, Ashton & Crafts 1981; Hartley & Kidd 1987; Herbicide Handbook 1989) 46.0 (20°C, Worthing & Walker 1987, Worthing & Hance 1991) 44.0 (20–25°C, selected, Wauchope et al. 1992; Hornsby et al. 1996) 36.0 (20°C, Tomlin 1994) 45.0 (22°C, Milne 1995) Vapor Pressure (Pa at 25°C or as indicated): 1.73 (Ashton & Crafts 1973) 0.096 (20°C, Hartley & Graham-Bryce 1980) 1.733 (Herbicide Handbook 1983, 1989) 0.287 (20°C, GC-RT correlation, Kim 1985) 0.10 (20°C, selected, Suntio et al. 1988) 0.17 (Worthing & Hance 1991) 1.733 (20–25°C, selected, Wauchope et al. 1992; Hornsby et al. 1996) 1.73 (Tomlin 1994) Henry’s Law Constant (Pa·m3/mol at 25°C or as indicated): 0.560 (20°C, calculated-P/C, Suntio et al. 1988) Octanol/Water Partition Coefficient, log KOW: 4.15 (Worthing & Hance 1991; Tomlin 1994; Milne 1995) 4.15 (recommended, Hansch et al. 1995) 4.17, 4.01, 3.45 (RP-HPLC-RT correlation, CLOGP, calculated-S, Finizio et al. 1997) S N O © 2006 by Taylor & Francis Group, LLC 3498 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals Bioconcentration Factor, log BCF: 1.86 (calculated-S, Kenaga 1980) 3.06 (calculated-KOW as per Kenaga 1980, this work) Sorption Partition Coefficient, log KOC: 2.73 (soil, Kenaga 1980) 2.73, 4.09 (quoted values, Bottoni & Funari 1992) 2.60 (soil, 20–25°C, selected, Wauchope et al. 1992) 2.60 (estimated-chemical structure, Lohninger 1994) 2.11 (soil, calculated-MCI 1., Sabljic et al. 1995) 2.39, 2.13 (soil, estimated-class specific model, estimated-general model using molecular descriptors, Gramatica et al. 2000) Environmental Fate Rate Constants, k, or Half-Lives, t.: Half-Lives in the Environment: Air: Surface water: Ground water: reported half-lives or persistence, t. = 11–21 d (Bottoni & Funari 1992) Sediment: Soil: measured dissipation rate k = 3.6 d–1 (Nash 1983; quoted, Nash 1988); estimated dissipation rate k = 23 and 0.61 d–1 (Nash 1988); t. = 1.5–3.0 wk in several soils under crop growing conditions (Herbicide Handbook 1989); selected field t. = 13 d (Wauchope et al. 1992; quoted, Richards & Baker 1993; Hornsby et al. 1996) reported t. = 11–21 d (Bottoni & Funari 1992); soil t. = 12 d (quoted, Pait et al. 1992); t. = 1.5–10 wk in soil and water (Tomlin 1994); soil t. = 13 d (selected, Halfon et al. 1996). Biota: disappear from the stems and leaves of corn plants 7 to 14 d after application (Herbicide Handbook 1989). © 2006 by Taylor & Francis Group, LLC Herbicides 3499 17.1.1.14 Chloramben Common Name: Chloramben Synonym: ACP-M-728, Amiben, Amoben, Chlorambed, Chlorambene, M-728, NCI-C00055, Ornamental weeder, Vegaben, Vegiben Chemical Name: 3-amino-2,5-dichlorobenzoic acid Uses: pre-emergence or pre-plant herbicide used in many vegetable and field crops to control annual broadleaf weeds and grasses. CAS Registry No: 133-90-4 Molecular Formula: C7H5Cl2NO2 Molecular Weight: 206.027 Melting Point (C): 200 (Lide 2003) Boiling Point (°C): Density (g/cm3 at 20°C): Molar Volume (cm3/mol): 190.8 (calculated-Le Bas method at normal boiling point) Dissociation Constant pKa: 3.40 (Hornsby et al. 1996) Enthalpy of Fusion, .Hfus (kJ/mol): 38.91 (DSC method, Plato 1972) Entropy of Fusion, .Sfus (J/mol K): Fugacity Ratio at 25°C (assuming .Sfus = 56 J/mol K), F: 0.0192 (mp at 200°C) Water Solubility (g/m3 or mg/L at 25°C): 700 (Spencer 1973; Ashton & Crafts 1981) 700 (Martin & Worthing 1977; Herbicide Handbook 1978; 1989) 700 (Hartley & Kidd 1987; Budavari 1989; Montgomery 1993; Milne 1995) 700 (Worthing & Walker 1987, Worthing & Hance 1991; Tomlin 1994; Majewski & Capel 1995) Vapor Pressure (Pa at 25°C or as indicated): 0.933 (100°C, Segal & Sutherland 1967; Spencer 1976) 0.93 (100°C, Hartley & Kidd 1987; Worthing & Hance 1991; Tomlin 1994) 52.7 (Worthing & Walker 1987) Henry’s Law Constant (Pa·m3/mol at 25°C): 0.274 (calculated-P/C as per Worthing 1987) Octanol/Water Partition Coefficient, log KOW: 1.11 (quoted, Rao & Davidson 1980) 1.46 (selected, Dao et al. 1983) –2.64 (selected, Gerstl & Helling 1987) 1.11 (Magee 1991) 1.11 (Montgomery 1993) 1.11 (Log P database of Hansch & Leo 1987, Sangster 1993) 1.90 (CLOGPSTAR or CLOGP data, Sabljic et al. 1995) Bioconcentration Factor, log BCF: 1.18 (calculated-S, Kenaga 1980) O OH Cl NH2 Cl © 2006 by Taylor & Francis Group, LLC 3500 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals –0.097 (calculated-KOC, Kenaga 1980) Sorption Partition Coefficient, log KOC: 1.32 (soil, Harris & Warren 1964; Farmer 1976) 2.08 (soil, calculated as per Kenaga & Goring 1980, Kenaga 1980) 1.78 (calculated-MCI ., Gerstl & Helling 1987) 1.32 (reported as log KOM, Magee 1991) 2.28 (Montgomery 1993) 1.56 (selected, Lohninger 1994) 1.48 (soil, calculated-MCI 1., Sabljic et al. 1995) Environmental Fate Rate Constants, k, or Half-Lives, t.: Volatilization: Photolysis: t. = 6 h for 206 µg/mL to degrade in distilled water under sunlight (Sheets 1963; quoted, Cessna & Muir 1991); t. < 2 d for 16 µg/mL to degrade in distilled water under sunlight (Hahn et al. 1969; quoted, Cessna & Muir 1991). Oxidation: Hydrolysis: Biodegradation: t. > 70 d for 50 µg/mL to degrade in incubated soil with nutrient medium of 3 g/L (Schliebe et al. 1965; quoted, Muir 1991). Biotransformation: Bioconcentration, Uptake (k1) and Elimination (k2) Rate Constants: Half-Lives in the Environment: Soil: estimated persistence of 3 months (Kearney et al. 1969; quoted, Jury et al. 1987); t. = 36, 38, 41, and 20 d with disappearance rates: k = 0.0193, 0.0182, 0.0169 and 0.0347 d–1 at pH 4.3, 5.3, 6.5 and 7.5 (Hamaker 1972; quoted, Nash 1988); persistence in soil is of 6–8 wk (Hartley & Kidd 1987; Herbicide Handbook 1989; quoted, Montgomery 1993). © 2006 by Taylor & Francis Group, LLC Herbicides 3501 17.1.1.15 Chlorazine Common Name: Chlorazine Synonym: Chemical Name: 6-chloro-N,N,N.,N.-tetraethyl-1,3,5-triazine-2,4-diamine Uses: herbicide CAS Registry No: 580-48-3 Molecular Formula: C11H20ClN5 Molecular Weight: 257.764 Melting Point (°C): 27 (Howard 1991; Lide 2003) Boiling Point (°C): 154–156/4.0 mmHg (Howard 1991) Density (g/cm3): Acid Dissociation Constants, pKa: 1.74 (pKa of conjugate acid, Howard 1991) Molar Volume (cm3/mol): Enthalpy of Fusion, .Hfus (kJ/mol): Entropy of Fusion, .Sfus (J/mol K): Fugacity Ratio at 25°C, (assuming .Sfus = 56 J/mol K), F: 0.956 (mp at 27°C) Water Solubility (g/m3 or mg/L at 25°C or as indicated): 23.7, 22.2, 21.4 (26°C, shake flask-UV at pH 3.0, 7.0, 10.0, Ward & Weber 1968) Vapor Pressure (Pa at 25°C): Henry’s Law Constant (Pa·m3/mol at 25°C): Octanol/Water Partition Coefficient, log KOW: 3.236 (estimated, Howard 1991) Octanol/Air Partition Coefficient, log KOA: Bioconcentration Factor, log BCF or log KB: 2.033 (estimated-S, Howard 1991) Sorption Partition Coefficient, log KOC: 2.90 (calculated-S, Howard 1991) Environmental Fate Rate Constants, k, and Half-Lives, t.: Hydrolysis: may be more important at low pH (Howard 1991). Half-Lives in the Environment: Air: t. = 2.5 h for the vapor phase reaction with OH radicals (estimated, Howard 1991). N N N N N Cl © 2006 by Taylor & Francis Group, LLC 3502 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals 17.1.1.16 Chlorbromuron Common Name: Chlorbromuron Synonym: Maloran Chemical Name: 3-(4-bromo-3-chlorophenyl)-1-methoxy-1-methylurea Uses: herbicide CAS Registry No: 13360-45-7 Molecular Formula: C9H10BrClN2O2 Molecular Weight: 293.544 Melting Point (°C): 96 (Lide 2003) Boiling Point (°C): Density (g/cm3): 1.69 (Tomlin 1994) Acid Dissociation Constants, pKa: Molar Volume (cm3/mol): Enthalpy of Fusion, .Hfus (kJ/mol): Entropy of Fusion, .Sfus (J/mol K): Fugacity Ratio at 25°C, (assuming .Sfus = 56 J/mol K) F: 0.201 (mp at 96°C) Water Solubility (g/m3 or mg/L at 25°C or as indicated): 50 (Kenaga & Goring 1980, Kenaga 1980a; Ashton & Crafts 1981 35 (20°C, Spencer 1982; Worthing 1983; Hartley & Kidd 1987; Tomlin 1994) 35; 27.4 (quoted; calculated-MCI ., Patil 1994) 35 (selected, 20–25°C, Augustjin-Beckers 1994; Hornsby et al. 1996) Vapor Pressure (Pa at 25°C or as indicated): 5.33 . 10–5 (20°C, Ashton & Crafts 1981) 5.3 . 10–5 (Spencer 1982; Worthing 1983; Hartley & Kidd 1987; Tomlin 1994) 5.33 . 10–5 (selected, 20–25°C, Augustijn-Beckers et al. 1994; Hornsby et al. 1996) Henry’s Law Constant (Pa·m3/mol): Octanol/Water Partition Coefficient, log KOW: 3.06 (quoted, Rao & Davidson 1980) 3.09 (shake flask, Brigg 1981) 3.09; 3.26 (quoted lit.; calculated-MCI ., Patil 1994) 3.09 (recommended, Hansch et al. 1995) 2.86, 2.99, 3.45 (RP-HPLC-RT correlation, CLOGP, HPLC-k. correlation, Finizio et al. 1997) Octanol/Air Partition Coefficient, log KOA: Bioconcentration Factor, log BCF or log KB: 1.83, 1.40 (quoted, calculated, Kenaga 1980b) Sorption Partition Coefficient, log KOC: 2.66 (soil, Kenaga & Goring 1980) 2.66, 2.71 (quoted, calculated-KOW, Kenaga 1980b) 3.00 (mean value of 5 soils, Rao & Davidson 1980) 2.34, 2.94 (quoted, calculated-MCI ., Gerstl & Helling 1987) 2.19–3.61 (range of reported data, Augustijn-Beckers et al. 1994) HN N O O Cl Br © 2006 by Taylor & Francis Group, LLC Herbicides 3503 2.70 (estimated and recommended, soil, Augustjin-Beckers et al. 1994; Hornsby et al. 1996) 2.70 (soil, calculated-MCI 1., Sabljic et al. 1995) 2.70, 2.97 (soil, estimated-class-specific model, estimated-general model using molecular descriptors, Gramatica et al. 2000) 2.54, 2.55 (soils: organic carbon OC . 0.1%, OC . 0.5%, average, Delle Site 2001) Environmental Fate Rate Constants, k, and Half-Lives, t.: Hydrolysis: slowly hydrolyzed in neutral, slightly acidic, and slightly alkaline media (Hartley & Kidd 1987; Tomlin 1994). Half-Lives in the Environment: Soil: persists in soil > 56 d (Worthing 1983); t. = 45 d (Hartley & Kidd 1987); t. = 45–120 d (Tomlin 1994); t. = 21–45 d and 40 d (range of reported values and recommended field half-life, Augustjin-Beckers et al. 1994; Hornsby et al. 1996) © 2006 by Taylor & Francis Group, LLC 3504 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals 17.1.1.17 Chlorpropham Common Name: Chlorpropham Synonym: Beet-Kleen, Bud-nip, Chlor-IFC, Chloro-IPC, CIPC, Ebanil, ENT 18060, Fasco Wy-hoe, Furloe, Nexoval, Prevenol, Preweed, Sprout-nip, Taterpex Chemical Name: isopropyl N-(3-chlorophenyl) carbamate; isopropyl 3-chlorocarbanilate Uses: pre-emergent and post-emergent herbicide used to regulate plant growth and control weeds in carrot, onion, garlic, and other crops. CAS Registry No: 101-21-3 Molecular Formula: C10H12ClNO2 Molecular Weight: 213.661 Melting Point (°C): 41 (Lide 2003) Boiling Point (°C): 149 (at 2 mmHg, Budavari 1989) Density (g/cm3 at 20°C): 1.180 (30°C, Hartley & Kidd 1987; Herbicide Handbook 1989; Worthing & Hance 1991; Montgomery 1993; Tomlin 1994) 1.5388 (Budavari 1989) Molar Volume (cm3/mol): 232.4 (calculated-Le Bas method at normal boiling point) Enthalpy of Vaporization, .HV (kJ/mol): 88.67 (Rordorf 1989) Enthalpy of Fusion, .Hfus (kJ/mol): 20.50 (DSC method, Plato & Glasgow 1969) 16 (Rordorf 1989) Entropy of Fusion, .Sfus (J/mol K): Fugacity Ratio at 25°C (assuming .Sfus = 56 J/mol K), F: 0.697 (mp at 41°C) Water Solubility (g/m3 or mg/L at 25°C or as indicated): 0.470 (Brust 1966) 102.3 (shake flask-GC, Freed et al. 1967) 108 (20°C, Gunther et al. 1968) 89 (20°C, Weber 1972; Martin & Worthing 1977; Worthing & Walker 1987) 2.0 (Spencer 1973; quoted, Shiu et al. 1990) 88 (Martin & Worthing 1977; Herbicide Handbook 1978, 1989) 0.70 (19°C, shake flask-GC, Bowman & Sans 1979) 0.73 (20°C, shake flask-GC, Bowman & Sans 1983a,b) 88 (Khan 1980; Ashton & Crafts 1981) 80–102 (Weber et al. 1980) 89 (Hartley & Kidd 1987; Worthing & Hance 1991; Tomlin 1994) 89 (selected, Gerstl & Helling 1987; Montgomery 1993; Lohninger 1994) 2.0 (20°C, Worthing & Walker 1987) Vapor Pressure (Pa at 25°C or as indicated and reported temperature dependence equations): 0.00050 (20°C, Weber 1972; Worthing & Walker 1987) 0.00133 (extrapolated, Spencer 1976) 0.00133 (Khan 1980) 0.00133 (Ashton & Crafts 1981; Herbicide Handbook 1989) 0.00100 (20°C, selected, Suntio et al. 1988) HN O O Cl © 2006 by Taylor & Francis Group, LLC Herbicides 3505 0.012, 0.30, 5.0, 56, 470 (25, 50, 70, 100, 125°C, gas saturation-GC, Rordorf 1989) log (PS/Pa) = 16.402 – 5467.7/(T/K); measured range 44.9–140°C (solid, gas saturation-GC, Rordorf 1989) log (PL/Pa) = 13.753 – 4631.9/(T/K); measured range 44.9–140°C (liquid, gas saturation-GC, Rordorf 1989) 0.00130 (selected, Taylor & Spencer 1990) 0.00107 (20–25°C, selected, Wauchope et al. 1992; Hornsby et al. 1996) 0.00133 (estimated, Montgomery 1993) Henry’s Law Constant (Pa m3/mol at 25°C or as indicated): 0.0021 (20°C, calculated-P/C, Suntio et al. 1988) 0.0032 (20°C, calculated-P/C, Muir 1991) 0.0021 (20–25°C, calculated-P/C, Montgomery 1993) Octanol/Water Partition Coefficient, log KOW: 3.06 (Rao & Davidson 1980; Karickhoff 1981) 3.42 (selected, Dao et al. 1983; Gerstl & Helling 1987) 3.51 (shake flask, Mitsutake et al. 1986) 3.10 (selected, Suntio et al. 1988) 3.51 (recommended, Sangster 1993) 3.09 (calculated, Patil 1994) 3.51 (recommended, Hansch et al. 1995) Bioconcentration Factor, log BCF: 1.70 (calculated-S, Kenaga 1980) 1.52 (calculated-KOC, Kenaga 1980) Sorption Partition Coefficient, log KOC: 2.77 (soil, Hamaker & Thompson 1972) 2.57 (soil, calculated-S as per Kenaga & Goring 1980, Kenaga 1980) 2.85, 2.80 (estimated-S, Karickhoff 1981) 3.17, 3.08 (estimated-S and mp, Karickhoff 1981) 2.67 (estimated-KOW, Karickhoff 1981) 2.31 (calculated-MCI ., Gerstl & Helling 1987) 2.32 (calculated-MCI . and fragment contribution method, Meylan et al. 1992) 2.60 (soil, 20–25°C, estimated, Wauchope et al. 1992; Hornsby et al. 1996) 2.77, 2.91 (Montgomery 1993) 2.60 (estimated-chemical structure, Lohninger 1994) 2.53 (soil, calculated-MCI 1., Sabljic et al. 1995) 2.40, 2.05 (soil, estimated-class-specific model, estimated-general model using molecular descriptors, Gramatica et al. 2000) 2.62 (2.37–2.87) (soil: organic carbon OC . 0.5%, average, Delle Site 2001) Environmental Fate Rate Constants, k, or Half-Lives, t.: Volatilization: t. = 2220 d from 1-m depth of water at 20°C (estimated, Muir 1991). Photolysis: t. = 130 h for 4 µg/mL to degrade in distilled water under > 280 nm light (Guzik 1978; quoted, Cessna & Muir 1991) direct photolysis t. = 121 d in distilled water pH 5–7 for a mid-summer day at latitude of 40° (Wolfe et al. 1978) t.= 2.25 h for 21–76% of 80 µg/mL to degrade in distilled water under 300 nm light (Tanaka et al. 1981; quoted, Cessna & Muir 1991). Oxidation: Hydrolysis: t. > 4 months for 4274 µg/mL to hydrolyze in phosphate buffer at pH 5–9 and 20°C (El-Dib & Aly 1976; quoted, Muir 1991) k(alkaline) = 2.0 . 10–5 M–1 s–1 at 27°C, 1.9 . 10–4 M–1 s–1 at 50°C, 6.4 . 10–4 M–1 s–1 at 70°C; with t. > 1 . 104 d at pH 5, 7 and 9 (Wolfe et al. 1978) © 2006 by Taylor & Francis Group, LLC 3506 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals t. > 1 wk for 2.10 µg/mL to hydrolyze in natural waters at 67°C (Schnoor et al. 1982; quoted, Muir 1991). Biodegradation: t.(aerobic) = 10–75 d for 0.1–5.4 µg/mL to biodegrade in activated sludge (Schwartz 1967; quoted, Muir 1991) k = (3.6–6.7) . 10–10 mL cell–1 d–1 of different river water samples (Paris et al. 1978; quoted, Scow 1982) t. = 120 d by fungi Aspergillus fumigatus and t. = 2.9 d by bacteria at 28°C (Wolfe et al. 1978) k = 2.5 . 10–4 L (mg M)–1 h–1 with t. = 120 d for 2–25 µg/mL fungus Aspergillus fumigatus; k = 0.1 L (mg M)–1 h–1 with t. = 2.9 d for bacteria Pseudomonas striata to biodegrade in stream water at pH 7 and 28°C (Wolfe et al. 1978; quoted, Muir 1991) k = (1.6–1.8) . 10–8 mL cell–1 d–1 of different river water samples (Steen et al. 1979; quoted, Scow 1982) k = (2.6 ± 0.72) . 10–14 L cell–1 h–1 in North American waters (Paris et al. 1981; quoted, Battersby 1990) k = (1.3–4.9) . 10–4 L org–1 h–1 with t.(aerobic) = 190 h for 0.1–1.0 µg/mL to biodegrade in lake water at 22°C (Schnoor et al. 1982; quoted, Muir 1991) k = (1.4–4.2) . 10–13 L org–1 h–1 for 75 µg/mL to biodegrade at 28°C in natural and sediment waters (Steen et al. 1982; quoted, Muir 1991); t.(aerobic) > 4 months for 6–7 µg/mL to biodegrade in river water at 25°C (Stepp et al. 1985; quoted, Muir 1991). Biotransformation: Bioconcentration, Uptake (k1) and Elimination (k2) Rate Constants: Half-Lives in the Environment: Air: Surface water: rate constant k = 3.6–6.7 . 10–10 mL cell–1 d–1 from measurements of different river water samples (Paris et al. 1978; quoted, Scow 1982); hydrolysis t. > 1 . 104 d based on neutral and alkaline hydrolysis assuming pseudo-first order kinetics; direct photolysis t. = 121 d assuming a quantum efficiency of 1 and for a mid-summer day at altitude 40°, and biolysis t. = 120 d for 1mg/L of fungus and t. = 2.9 d for bacteria at 28°C (Wolfe et al. 1978); k = (1.6–1.8) . 10–8 mL cell–1 d–1 from measurements of different river water samples (Steen et al. 1979; quoted, Scow 1982); aerobic t. = 190 h for 0.1–1.0 µg/mL to biodegrade in lake water with biodegradation rate of (1.3–4.9) . 10–4 L org–1 h–1 at 22°C (Schnoor et al. 1982; quoted, Muir 1991); aerobic t. > 4 months for 6–7 µg mL–1 to biodegrade in river water at 25°C (Stepp et al. 1985; quoted, Muir 1991). Ground water: Sediment: aerobic half-life of 10–75 d for 0.1–5.4 µg/mL to biodegrade in activated sludge (Schwartz 1967; quoted, Muir 1991). Soil: t. = 65 and 30 d soil at 15 and 29°C, respectively (Hartley & Kidd 1987; Herbicide Handbook 1989; quoted, Montgomery 1993; Tomlin 1994); selected field t. = 30 d (Wauchope et al. 1992; Hornsby et al. 1996). Biota: © 2006 by Taylor & Francis Group, LLC Herbicides 3507 17.1.1.18 Chlorsulfuron Common Name: Chlorsulfuron Synonym: DPX 4189, Finesse, Glean, Telar Chemical Name: 2-chloro-N-(((4-methoxy-6-methyl-1,3,5-triazin-2-yl)amino)-carbonyl)-benzenesulfonamide; 1-(o-chlorophenyl)-3-(4-methoxy-6-methyl-s-triazin-2-yl)urea Uses: herbicide to control broadleaf weeds and some grass weeds. CAS Registry No: 64902-72-3 Molecular Formula: C12H12ClN5O4S Molecular Weight: 357.773 Melting Point (°C): 176 (Lide 2003) Boiling Point (°C): 192 (dec., Herbicide Handbook 1989; Montgomery 1993) Density (g/cm3 at 20°C): Molar Volume (cm3/mol): Dissociation Constant pKa: 3.6 (Herbicide Handbook 1989; Worthing & Hance 1991; Montgomery 1993; Tomlin 1994) Enthalpy of Fusion, .Hfus (kJ/mol): Entropy of Fusion, .Sfus (J/mol K): Fugacity Ratio at 25°C (assuming .Sfus = 56 J/mol K), F: 0.0330 (mp at 176°C) Water Solubility (g/m3 or mg/L at 25°C or as indicated): 300 (at pH 5, Hartley & Kidd 1987; Worthing & Hance 1991; Tomlin 1994; Milne 1995) 27900 (at pH 7, Hartley & Kidd 1987; Worthing & Hance 1991; Tomlin 1994; Milne 1995) 28000 (at pH 7 with ionic strength 0.05, Herbicide Handbook 1989) 7000 (20–25°C, at pH 7, selected, Wauchope et al. 1992; quoted, Majewski & Capel 1995) 7000 (20–25°C, at pH 7, selected, Hornsby et al. 1996) 60, 7000 (at pH 5, pH 7, Montgomery 1993) 32000 (selected, Armbrust 2000) Vapor Pressure (Pa at 25°C or as indicated): 6.10 . 10–4 (Hartley & Kidd 1987) 6.13 . 10–4 (Herbicide Handbook 1989) 3.00 . 10–9 (Worthing & Hance 1991; Tomlin 1994) 1.98 . 10–2 (20–25°C, Wauchope et al. 1992) 3.11 . 10–9 (Montgomery 1993) 6.13 . 10–4 (20–25°C, selected, Hornsby et al. 1996) Henry’s Law Constant (Pa·m3/mol at 25°C or as indicated): 3.60 . 10–11 (calculated-P/C, Montgomery 1993) 1.98 . 10–5 (20–25°C, calculated-P/C as per Wauchope et al. 1992, Majewski & Capel 1995) 6.79 . 10–6 (selected, Armbrust 2000) Octanol/Water Partition Coefficient, log KOW: –0.84, 0.17, 1.09 (pH 8.4, pH 7.1, pH 4.5, UV, Ribo 1988) –0.88, 1.05 (pH 8.4, pH 4.5, HPLC, Ribo 1988) –1.34, 0.74 (pH 7, pH 4.5, Hay 1990) N N N O NH NH O S O O Cl © 2006 by Taylor & Francis Group, LLC 3508 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals 2.20 (Grayson & Kleier 1990) –1.0 (Montgomery 1993) –0.88, 1.05, –1.34, 0.74, 2.20 (reported values, Sangster 1993) –1.00 (at pH 7, Tomlin 1994) 0.74, –1.34 (lit. values, Hansch et al. 1995) 2.14 (LOGPSTAR or CLOGP data, Sabljic et al. 1995) Bioconcentration Factor, log BCF: 0.622 (calculated-S as per Kenaga 1980, this work) Sorption Partition Coefficient, log KOC: 1.02 (Flanagan silt loam, Montgomery 1993) 1.60 (Tomlin 1994) 2.19 (calculated-MCI 1., Sabljic et al. 1995) 1.60 (at pH 7, selected, Hornsby et al. 1996) 1.56 (selected, Armbrust 2000) Environmental Fate Rate Constants, k, or Half-Lives, t.: Volatilization: Photolysis: assuming first-order kinetics, calculated t. .186 h for 33 µg/mL to degrade in distilled water, t. = 31 h for creek water, t. = 136 h for silica gel and t. = 115 h for montmorillonit under sunlight (Herrmann et al. 1985; quoted, Cessna & Muir 1991); under indoor conditions t. = 92 h in methanol, t. = 78 h in distilled water but t. = 18 h in natural creek water (Herrmann et al. 1985); reported t. = 18 h in distilled water at > 290 nm (Montgomery 1993) aqueous photolysis rate constant, k = 5.0 . 10–4 h–1 (Armbrust 2000). Oxidation: Hydrolysis: t. = 4–8 wk at 20°C and pH 5.7–7.0 (Hartley & Kidd 1987; Worthing & Hance 1991; Montgomery 1993; Tomlin 1994); stable aqueous hydrolysis rates at pH 7, 9; measured hydroxy radical rate constant for chlorsulfuron 6.9 . 1012 M–1/h (Armbrust 2000). Biodegradation: aerobic rate constant, k = 1.44 . 10–3 h–1 (Armbrust 2000). Biotransformation: Bioconcentration, Uptake (k1) and Elimination (k2) Rate Constants: Half-Lives in the Environment: Soil: hydrolysis rates will be increased by warm soil temperatures at low pH and in the presence of moisture with an average t. = 4–6 wk under growing conditions (Hartley & Kidd 1987; Herbicide Handbook 1989) t. = 4–6 wk for degradation in soil via hydrolysis followed by microbial degradation (Hartley & Kidd 1987; quoted, Montgomery 1993; Tomlin 1994); degradation rate constants: k = 0.033 d–1 at depth 0–20 cm with t. = 21 d, k = 0.0315 d–1 at depth 20–40 cm with t. = 22 d and for depth 40–60 cm with t. > 150 d (Soakwaters soil, Walker et al. 1989); degradation k = 0.0116 d–1 at depth 0–20 cm with t. = 60 d, k = 0.0120 d–1 at depth 20–40 cm with t. = 58 d, and k = 0.0076 d–1 at depth 40–60 cm with t. = 91 d (Wharf ground soil, Walker et al. 1989); degradation k = 0.0126 d–1 at depth 0–20 cm with t. = 55 d, k = 0.0073 d–1 at depth 20–40 cm with t. = 95 d, and k = 0.0056 d–1 at depth 40–60 cm with t. = 124 d (Cottage Field soil, Walker et al. 1989); degradation k = 0.0147 d–1 at depth 0–20 cm with t. = 47 d, 0.0116 d–1 at depth 20–40 cm with t. = 60 d, and k = 0.0047 d–1 at depth 40–60 cm with t. = 147 d (Hunts Mill soil, Walker et al. 1989); degradation 0.0094 d–1 (depth 0–20 cm with t. = 74 d), 0.0096 d–1 (depth 20–40 cm with t. = 72 d) and 0.0082 d–1 (depth 40–60 cm with t. = 85 d) (Bottom Barn soil, Walker et al. 1989); degradation k = 0.0141 d–1 at depth 0–20 cm with t. = 49 d, k = 0.0126 d–1 at depth 20–40 cm with t. = 55 d, and k = 0.0089 d–1 at depth 40–60 cm with t. = 78 d (Long Ashton soil, Walker et al. 1989); degradation k = 0.0144 d–1 at depth 0–20 cm with t. = 48 d, k = 0.0126 d–1 at depth 20–40 cm with t. = 55 d, and k = 0.0124 d–1 at depth 40–60 cm with t. = 56 d (Norfolk Agricultural Station soil, Walker et al. 1989) © 2006 by Taylor & Francis Group, LLC Herbicides 3509 degradation k = 0.0248 d–1 at depth 0–20 cm with t. = 28 d, k = 0.0289 d–1 at depth 20–40 cm with t. = 24 d, and k = 0.0347 d–1 at depth 40–60 cm with t. = 20 d (Norfolk Agricultural Station soil, Walker et al. 1989); selected field t. = 40 d (Hornsby et al. 1996). © 2006 by Taylor & Francis Group, LLC 3510 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals 17.1.1.19 Chlorotoluron Common Name: Chlorotoluron Synonym: C 2242, Clortokem, Deltarol, Dicuran, Highuron, Higaluron, Tolurex Chemical Name: 3-(3-chloro-p-tolyl)-1,1-dimethylurea; N.-(3-chloro-4-methylphenyl)-N,N-dimethylurea Uses: herbicide to control pre- and post-emergent annual grasses and broadleaf weeds in winter cereals, particularly wheat and barley. CAS Registry No: 15545-48-9 Molecular Formula: C10H13ClN2O Molecular Weight: 212.675 Melting Point (°C): 147 (Lide 2003) Boiling Point (°C): Density (g/cm3 at 20°C): 1.40 (Tomlin 1994) Molar Volume (cm3/mol): 192 (modified Le Bas method at normal boiling point, Spurlock & Biggar 1994) Dissociation Constant pKa: Enthalpy of Fusion, .Hfus (kJ/mol): Entropy of Fusion, .Sfus (J/mol K): Fugacity Ratio at 25°C (assuming .Sfus = 56 J/mol K), F: 0.0635 (mp at 147°C) Water Solubility (g/m3 or mg/L at 25°C or as indicated): 10.0 (20°C, Spencer 1973) 70.0 (Martin & Worthing 1977) 10.0 (20°C, Khan 1980) 70.0 (20°C, Ashton & Crafts 1981) 56.4, 80.6, 99.1 (4, 25, 40°C, shake flask-liquid scintillation spectrometer LSS, Madhun et al. 1986) 70.0 (20°C, Hartley & Kidd 1987; Worthing & Walker 1991) 90.0 (Spurlock 1992; Spurlock & Biggar 1994) 10660 (calculated, Patil 1994) 74.0 (Tomlin 1994) 49.3 (predicted-AQUAFAC, Lee et al. 1996) Vapor Pressure (Pa at 25°C or as indicated): 4.8 . 10–6 (20°C, Khan 1980) 1.7 . 10–5 (20°C, Ashton & Crafts 1981) 1.7 . 10–5 (20°C, Hartley & Kidd 1987) 1.7 . 10–5 (Tomlin 1994; selected, Halfon et al. 1996) Henry’s Law Constant (Pa·m3/mol at 25°C or as indicated): 5.17 . 10–5 (20°C, calculated-P/C, this work) Octanol/Water Partition Coefficient, log KOW: 2.41 (shake flask-UV, Briggs 1981) 2.54 (Dao et al. 1983; Spurlock 1992; Spurlock & Biggar 1994) 2.33, 2.34, 2.32 (4, 25, 40°C, shake flask-liquid scintillation spectrometer LSS, Madhun et al. 1986) 2.41 (shake flask, Mitsutake et al. 1986) 2.0 (shake flask, pH 7, Baker et al. 1992) HN N O Cl © 2006 by Taylor & Francis Group, LLC Herbicides 3511 2.241 (calculated, Evelyne et al. 1992) 2.41 (recommended, Sangster 1993) 2.25 (RP-HPLC-RT correlation, Sicbaldi & Finizio 1993) 0.26 (calculated, Patil 1994) 2.50 (Tomlin 1994) 2.41 (recommended, Hansch et al. 1995) 2.38, 2.44 (shake flask-UV, calculated-RP-HPLC-k. correlation, Liu & Qian 1995) 2.25, 2.49, 2.42 (RP-HPLC-RT correlation, ClOGP, calculated-S, Finizio et al. 1997) 2.0 (RP-HPLC-RT correlation using short ODP column, Donovan & Pescatore 2002) Bioconcentration Factor, log BCF: 1.75 (calculated-S, Kenaga 1980) 2.09, 2.16 (cuticle/water 24 h: tomato, pepper, Chaumat et al. 1991) 2.01, 2.15 (cuticle/water 24 h: box tree, pear, Chaumat et al. 1991) 1.30 (cuticle/water 24 h: vanilla, Chaumat et al. 1991) 2.09, 2.16 (cuticle/water: tomato, pepper, Evelyne et al. 1992) Sorption Partition Coefficient, log KOC: 2.62 (soil, calculated-S, Kenaga 1980) 1.78 (reported as log KOM, Briggs 1981) 2.75, 2.62 (4°C, 25°C, Semiahmoo soil, in µmol/kg OC, batch equilibrium-sorption isotherm-liquid scintillation spectrometer LSS, Madhun et al. 1986) 2.57, 2.43 (4°C, 25°C, Adkins soil, in µmol/kg OC, batch equilibrium method-LSS, Madhun et al. 1986) 2.48, 2.18; 2.54, 2.50 (estimated-KOW; solubility, Madhun et al. 1986) 2.81, 2.58 (exptl., calculated-KOW, Liu & Qian 1995) 2.02 (soil, calculated-MCI 1., Sabljic et al. 1995) 2.02; 2.05, 2.15 (soil, quoted obs.; estimated-class-specific model, estimated-general model using molecular descriptors, Gramatica et al. 2000) 2.00, 2.00 (soils: organic carbon OC . 0.1%, OC . 0.5%, average, Delle Site 2001) 2.14, 2.36 (Kishon river sediments, sorption isotherm, Chefetz et al. 2004) Environmental Fate Rate Constants, k, or Half-Lives, t.: Volatilization: Photolysis: Oxidation: Hydrolysis: calculated t. > 200 d at pH 5, 7, 9 and 30°C (Tomlin 1994). Biodegradation: Biological degradation rate followed a first order kinetics with t. = 21.6 d by raw water microflora from River Nile, t. = 13,8 d by raw water microflora + sewage (El-Dib & Abou-Waly 1998) Biotransformation: 4% of the selected 90 strains of micromycetes mostly isolated from soil-soil fungi, depleted 50% of chlorotoluron (100 mg/L) in 5-d experiment. (Vroumsia et al. 1996) Bioconcentration, Uptake (k1) and Elimination (k2) Rate Constants: Half-Lives in the Environment: Air: Surface water: Biological degradation t. = 21.6 d by raw water microflora from River Nile, t. = 13,8 d by raw water microflora + sewage (El-Dib & Abou-Waly 1998) Ground water: Sediment: Soil: t. = 4 wk in the moist silty loam at (25 ± 1)°C (Smith & Briggs 1978); t. ~ 200–4000 d in loamy sand and peat for 25–35°C as follows (Madhum & Freed 1987): t. = 4340, 904, and 381 d at 25, 30, and 35°C, respectively, at herbicide concn at 5 µg/kg, while t. = 1335, 524, and 266 d at 25, 30, and 35°C, respectively, at herbicide concn at 100 µg/kg in an Adkins loamy sand; however, the half-lives in peat. t. = 2306, 1245, and 618 d at 25, 30, and 35°C, respectively, at herbicide concn at 5 µg/kg while t. = 1949, 1024, and 582 d at 25, 30, and 35°C, respectively, at herbicide concn at 100 µg/kg in a Semiahoo mucky peat (Madhun & Freed 1987) © 2006 by Taylor & Francis Group, LLC 3512 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals degradation by microorganism in biometer systems, t. = 93 d in silty sand standard metabolism experiments, t. = 140 d corrected standard conditions, t. = 110 d in simulated outdoor conditions; t. = 40 d in silty loam standard conditions, t. = 60 d corrected standard conditions, t. = 31 d in simulated outdoor conditions; at constant soil moisture and 20°C. Degradation by microorganism in small lysimeter systems: t. = 52 d outdoor fallow, t. = 14 d outdoor barley in silty sand, and t. = 49 d outdoor fallow, t. = 38 d outdoor barley in silty loam (Rudel et al. 1993) t. = 30–40 d in soil (Tomlin 1994); t. = 135 d (selected, Halfon et al. 1996). Biota: © 2006 by Taylor & Francis Group, LLC Herbicides 3513 17.1.1.20 Cyanazine Common Name: Cyanazine Synonym: Bladex, 90DF, DW 3418, Fortrok, Fortrol, Payze, SD 15418, WL 19805 Chemical Name: 2-(4-chloro-6-ethylamino-1,3,5-triazin-2-ylamino)-2-methyl-propionitrile Uses: herbicide to control annual grasses and broadleaf weeds in cereals, cotton, maize, onions, peanuts, peas, potatoes, soybeans, sugar cane, and wheat fallow. CAS Registry No: 21725-46-2 Molecular Formula: C9H13ClN6 Molecular Weight: 240.692 Melting Point (°C): 168 (Lide 2003) Boiling Point (°C): Density (g/cm3 at 20°C): Molar Volume (cm3/mol): Dissociation Constant: 1.00 (pKa, Weber et al. 1980; Willis & McDowell 1982) 12.9 (pKb, Wauchope et al. 1992; Hornsby et al. 1996) 0.63, 1.1 (pKa, Montgomery 1993) Enthalpy of Fusion, .Hfus (kJ/mol): Entropy of Fusion, .Sfus (J/mol K): Fugacity Ratio at 25°C (assuming .Sfus = 56 J/mol K), F: 0.0395 (mp at 168°C) Water Solubility (g/m3 or mg/L at 25°C or as indicated): 171 (Melnikov 1971; Wauchope 1978; Weber et al. 1980; Ashton & Crafts 1981) 171 (Martin & Worthing 1977; Herbicide Handbook 1978; Worthing & Walker 1987, Worthing & Hance 1991; Majewski & Capel 1995) 150 (selected, Schnoor & McAvoy 1981; Schnoor 1992) 171 (Hartley & Kidd 1987; Montgomery 1993; Tomlin 1994) 160 (23°C, Herbicide Handbook 1989) 171 (Budavari 1989; Milne 1995) 170 (20–25°C, selected, Wauchope et al. 1992; Hornsby et al. 1996) 6046 (calculated, Patil 1994) 45 (calculated-group contribution fragmentation method, Kuhne et al. 1995) Vapor Pressure (Pa at 25°C or as indicated. Additional data at other temperatures designated * are compiled at the end of this section): 2.13 . 10–7 (20°C, Ashton & Crafts 1973; 1981; Spencer 1982; Herbicide Handbook 1989) 2.67 . 10–7 (20–25°C, Weber et al. 1980) 5.33 . 10–7 (selected, Schnoor & McAvoy 1981; Schnoor 1992) 1.00 . 10–5 (20°C, extrapolated from gas saturation measurement, Grayson & Fosbracey 1982) ln (P/Pa) = 25.7–10913/(T/K), temp range 65.7–92°C, (Antoine eq., gas saturation, Grayson & Fosbracey 1982) 2.00 . 10–7 (20°C, Hartley & Kidd 1987; Worthing & Hance 1991; Tomlin 1994; Majewski & Capel 1995) 5.21 . 10–6 (Worthing & Walker 1987) 1.33 . 10–6 (30°C, Herbicide Handbook 1989) 2.13 . 10–7 (20°C, Budavari 1989) 2.13 . 10–7 (20–25°C, selected, Wauchope et al. 1992; Hornsby et al. 1996) 2.13 . 10–7 (20°C, Montgomery 1993) N N N Cl NH NH N © 2006 by Taylor & Francis Group, LLC 3514 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals Henry’s Law Constant (Pa·m3/mol at 25°C or as indicated): 2816 (20–25°C, calculated-P/C, Montgomery 1993) 2.87 . 10–7 (calculated-P/C as per Worthing & Walker 1987, Majewski & Capel 1995) 3.00 . 10–7 (calculated-P/C, this work) Octanol/Water Partition Coefficient, log KOW: 2.18 (Kenaga & Goring 1980) 2.24 (shake flask-GC, Brown & Flagg 1981) 1.80, 1.66 (RP-HPLC-RT correlation, calculated, Finizio et al. 1991) 2.22 (selected, Magee 1991) 1.80, 2.24 (Montgomery 1993) 2.22 (recommended, Sangster 1993) 0.79 (calculated, Patil 1994) 2.10 (Tomlin 1994) 2.22 (recommended, Hansch et al. 1995) 2.04 (shake flask-UV, Liu & Qian 1995) 1.64, 1.29, 3.02 (RP-HPLC-RT correlation, CLOGP, calculated-S, Finizio et al. 1997) 1.70 (RP-HPLC-RT correlation using short ODP column, Donovan & Pescatore 2002) Bioconcentration Factor, log BCF: 1.53 (calculated-S, Kenaga 1980) 1.00 (calculated-KOC, Kenaga 1980) 1.48 (selected, Schnoor & McAvoy 1981; Schnoor 1992) Sorption Partition Coefficient, log KOC: 2.30 (Kenaga 1980; Kenaga & Goring 1980; Karickhoff 1981; Sabljic 1987; Bahnick & Doucette 1988) 2.41 (soil, calculated-S as per Kenaga & Goring 1980, Kenaga 1980) 2.26 (Georgia’s Hickory Hill pond sediment, Brown & Flagg 1981) 2.71, 1.75, 1.85 (estimated-S, calculated-S and mp, calculated-KOW, Karickhoff 1981) 0.48–1.48 (selected, sediment/water, Schnoor & McAvoy 1981; Schnoor 1992) 2.57, 2.26 (soil, quoted, Madhun et al. 1986) 2.36, 2.09; 2.33, 1.75 (estimated-reported KOWs; estimated-reported solubilities, Madhun et al. 1986) 2.23 (soil, screening model calculations, Jury et al. 1987b) 2.35 (calculated-MCI ., Bahnick & Doucette 1988) 2.30, 2.16 (reported, estimated as log KOM, Magee 1991) 2.23, 2.26, 2.30 (soil, quoted values, Bottoni & Funari 1992) 2.28 (soil, 20–25°C, selected, Wauchope et al. 1992; quoted, Richards & Baker 1993; Hornsby et al. 1996) 1.58–2.63 (Montgomery 1993) 2.54 (selected, Lohninger 1994) 2.05, 2.11 (exptl., calculated-KOW, Liu & Qian 1995) 2.28 (soil, calculated-MCI 1., Sabljic et al. 1995) 2.28; 2.33, 2.25 (soil, quoted obs.; estimated-class-specific model, estimated-general model using molecular descriptors, Gramatica et al. 2000) 2.14, 2.19 (soils: organic carbon OC . 0.1%, OC . 0.5%, pH 5.6–8.0, average, Delle Site 2001) Environmental Fate Rate Constants, k, or Half-Lives, t.: Volatilization: Photolysis: Oxidation: Hydrolysis: alkaline chemical hydrolysis t. > 365 d (Schnoor & McAvoy 1981; quoted, Schnoor 1992). Biodegradation: aerobic t. = 14 d for 0.06 µg/mL to degrade in pond water and t. > 28 d in pond sediment both at 10–20°C (Roberts 1974; quoted, Muir 1991). Biotransformation: Bioconcentration, Uptake (k1) and Elimination (k2) Rate Constants: © 2006 by Taylor & Francis Group, LLC Herbicides 3515 Half-Lives in the Environment: Air: Surface water: aerobic t. = 14 d for 0.06 µg/mL to degrade in pond water at 10–20°C (Roberts 1974; quoted, Muir 1991). Ground water: reported half-lives or persistence, t. = 10–29, 14 and 108 d (Bottoni & Funari 1992) Sediment: aerobic t. > 28 d for 0.06 µg/mL to slowly degrade in pond sediment at 10–20°C (Roberts 1974; quoted, Muir 1991). Soil: t. ~ 2 wk in soil (Beynon et al. 1972; quoted, Tomlin 1994); persistence of 12 months in soil (Wauchope 1978); t. = 13.5 d from screening model calculations (Jury et al. 1987b); t. = 12–15 d in sandy loam soils and t. = 20–25 d in silt and clay loam soils (Herbicide Handbook 1989; quoted, Montgomery 1993); disappearance t. = 181 d from the upper 15 cm on a clay loam Ontario soil in 1987 and t. = 90 d in 1988 with t.(calc) = 27 and 12 d, respectively (Frank et al. 1991); reported t. = 10–29 d, 13 d and 108 d (Bottoni & Funari 1992); selected field t. = 14 d (Wauchope et al. 1992; quoted, Richards & Baker 1993; Hornsby et al. 1996) soil t. = 19 d (Pait et al. 1992). Biota: biochemical t. = 13.5 d from screening model calculations (Jury et al. 1987b). TABLE 17.1.1.20.1 Reported vapor pressures of cyanazine at various temperatures Grayson & Fosbracey 1982 gas saturation-GC t/°C P/Pa 65.7 0.0016 70.0 0.0025 77.5 0.0040 85.8 0.0101 87.8 0.0096 92.0 0.0181 20 1. . 10–5 ln P = A – B/(T/K) P/Pa A 25.7 B 10913 © 2006 by Taylor & Francis Group, LLC 3516 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals FIGURE 17.1.1.20.1 Logarithm of vapor pressure versus reciprocal temperature for cyanazine. Cyanazine: vapor pressure vs. 1/T -6.0 -5.0 -4.0 -3.0 -2.0 -1.0 0.0 1.0 2.0 0.0022 0.0024 0.0026 0.0028 0.003 0.0032 0.0034 0.0036 1/(T/K) P( gol S ) aP / Grayson & Fosbracey 1982 m.p. = 168 °C © 2006 by Taylor & Francis Group, LLC Herbicides 3517 17.1.1.21 2,4-D (See also Chapter 13, Carboxylic Acids) Common Name: 2,4-D Synonym: 2,4-Dichlorophenoxyacetic acid Chemical Name: 2,4-dichlorophenoxyacetic acid Uses: post-emergence control of annual and perennial broadleaf weeds in cereals, maize, sorgum, grassland, established turf, grass seed crops, orchards, cranberries, asparagus, sugar cane, rice, forestry, and on noncropland, etc. CAS Registry No: 94-75-7 Molecular Formula: C8H6Cl2O3, Cl2C6H3OCH2COOH Molecular Weight: 221.038 Melting Point (°C): 140.5 (Hartley & Kidd 1987; Howard 1991; Tomlin 1994; Lide 2003) Boiling Point (°C): 160 (at 0.4 mmHg, Dean 1985) 215 (Neely & Blau 1985) Density (g/cm3 at 25°C): 1.565 (30°C, Neely & Blau 1985; Tomlin 1994) 1.416 (Montgomery 1993) Molar Volume (cm3/mol): 209.8 (calculated-Le Bas method at normal boiling point) Dissociation Constant, pKa: 2.73 (potentiometric method, Nelson & Faust 1969) 2.87 (spectrophotometric method, Cessna & Grover 1978) 2.80 (Reinert & Rogers 1984; selected, Wauchope et al. 1992) 2.64 (Dean 1985; Haag & Yao 1992; Lee et al. 1993) 2.61–3.31 (Howard 1991) 2.97 (Sangster 1993) 3.10 (Kollig 1993) 2.64–3.31 (Montgomery 1993) Enthalpy of Vaporization, .HV (kJ/mol): 93.89 (Rordorf 1989) Enthalpy of Fusion .Hfus (kJ/mol): 38.074 (DSC method, Plato & Glasgow 1969) 39.6 (Rordorf 1989) Entropy of Fusion, .Sfus (J/mol K): Fugacity Ratio at 25°C (assuming .Sfus = 56 J/mol K), F: 0.0736 (mp at 140.5°C) Water Solubility (g/m3 or mg/L at 25°C or as indicated): 890 (Hodgman 1952; Hamaker 1975; Verschueren 1983; Montgomery 1993) 522 (shake flask-UV, Leopold et al. 1960) 725 (Bailey & White et al. 1965) 725, 400, 900, 550 (Gunther et al. 1968) 900 (Herbicide Handbook 1974; Wauchope 1978; Kenaga 1980a,b; Kenaga & Goring 1980) 600 (20°C, Khan 1980) 620–900 (Weber et al. 1980) 470 (20–25°C, pH 5.6, Geyer et al. 1981) 633, 812 (15, 25°C, shake flask method, average values of 5 laboratories, OECD 1981) 620 (20°C, Hartley & Kidd 1983, 1987) Cl Cl O OH O © 2006 by Taylor & Francis Group, LLC 3518 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals 620 (Worthing & Walker 1983) 609 (Gerstl & Helling 1987) 400 (20°C, selected, Suntio et al. 1988) 703 (Gustafson 1989) 682 (Yalkowsky et al. 1987) 540–890(Nyholm et al. 1992) 900, 600, 890, 703, 1072 (Wauchope et al. 1992) 890 (20–25°C, selected, Wauchope et al. 1992) 311 (pH 1, Tomlin 1994) Vapor Pressure (Pa at 25°C or as indicated and reported temperature dependence equations): 8.0 . 10–5 (Hamaker 1975) 0.180–1.69 (transpiration method, Spencer 1976) 53.0 (160°C, Hartley & Kidd 1983, 1987) 8.0 . 10–5 (recommended, Neely & Blau 1985; Lyman 1985) 1.0 (20°C, selected, Suntio et al. 1988) 6.0 . 10–6 (selected, Nash 1989) 4.10 . 10–5, 2.0 . 10–3, 0.058, 1.10, 13.0 (25, 50, 70, 100, 125°C, gas saturation-GC, Rordorf 1989) log (PS/Pa) = 17.56 – 6544.1/(T/K); measured range 70.2–135°C (solid, gas saturation-GC, Rordorf 1989) log (PL/Pa) = 13.558 – 4904.6/(T/K); measured range 140–196°C (liquid, gas saturation-GC, Rordorf 1989) 0.20, 0.0032 (quoted, estimated from Henry’s law constant, Howard 1991) 5.6 . 10–5 (selected, Mackay & Stiver 1991) 1.40, 3.2 . 10–3 (quoted, estimated from HLC, Howard 1991) 1.33 . 10–5, 8.0 . 10–5, 1.07 . 10–3; 1.07 . 10–3 (20–25°C, quoted lit; selected, Wauchope et al. 1992) 0.627 (Montgomery 1993) 0.011 (Tomlin 1994) Henry’s Law Constant (Pa·m3/mol at 25°C or as indicated): 1.36 . 10–5 (calculated-P/C, Jury et al. 1983) 1.39 . 10–5 (calculated-P/C, Jury et al. 1987a, Jury & Ghodrati 1989) 0.55 (20°C, calculated-P/C, Suntio et al. 1988) 0.0015 (calculated, Nash 1989) 1.03 . 10–3 (calculated-bond contribution, Howard 1991) 6.80, 0.853 (pH 1, pH 7 at 20°C, wetted wall column-GC, Rice et al. 1997b) 1.82 . 10–7 (quoted lit., Armbrust 2000) Octanol/Water Partition Coefficient, log KOW: 2.81 (shake flask-UV, Fujita et al. 1964) 2.59 (electrometric titration, Freese et al. 1979) 1.57 (Kenaga & Goring 1980; Kenaga 1980b) 2.74 (selected, Dao et al. 1983) 2.81 (20°C, Verschueren 1983) 1.57, 4.88 (shake flask-OECD 1981 Guidelines, Geyer et al. 1984) 2.65 (shake flask, log P Database, Hansch & Leo 1987) 2.50 (OECD 1981 method, Kerler & Schonherr 1988) 2.649 (liquid/liquid-countercurrent-chromatography, Ilchmann et al. 1993) 2.81 (recommended, Sangster 1993) 1.44–4.18 (quoted lit. range, Montgomery 1993) 2.58–2.83 (pH 1, Tomlin 1994) 2.81 (selected, Hansch et al. 1995) 0.59 (RP-HPLC-RT correlation, CLOGP, Calculated-S, Finizio et al. 1997) © 2006 by Taylor & Francis Group, LLC Herbicides 3519 Octanol/Air Partition Coefficient, log KOA: Bioconcentration Factor, log BCF: 1.11, –0.097 (calculated-S, KOW, Kenaga 1980a) –2.46, 1.30 (beef fat, fish, Kenaga 1980b) 0.778, 1.94 (alga Chlorella: exptl. 24 h exposure, calculated-S, Geyer et al. 1981) 0.778 (algae, Freitag et al. 1982) < 1.00 (golden orfe, Freitag et al. 1982) 1.23 (activated sludge, Freitag et al. 1982) 0.0 (fish, microcosm conditions, Garten & Trabalka 1983;) 0.778, 1.23 (algae, calculated-KOW, Geyer et al. 1984) 1.23 (algae, Geyer et al. 1984) 1.11 (calculated, Isensee 1991) –5.00 (bluegill sunfish and channel catfish, Howard 1991) –2.70 (frog tadpoles, Howard 1991) –3.0, –2.52 (pH 7.8, seaweeds, Howard 1991) 0.778, 0.85 (quoted: alga, fish, Howard 1991) 0.0, 0.505 (catfish Ictalurus melas, water flea Daphnia magna, wet wt basis, Wang et al. 1996) Sorption Partition Coefficient, log KOC: 1.51 (Hamaker 1975) 1.30, 2.0 (quoted, calculated, Kenaga 1980a) 1.30, 2.11 (quoted, Kenaga & Goring 1980) 1.30 (quoted, Kenaga 1980b) 1.76 (quoted, average value of 3 soils, McCall et al. 1980) 2.25, 2.04, 2.35 (soil I-very strongly acid sandy soil pH 4.5–5.5, soil II-moderately or slightly acid loamy soil pH 5.6–6.5, soil III-slightly alkaline loamy soil pH 7.1–8.0, OECD 1981) 1.29 (soil, Neely & Blau 1985) 1.30 (soil, screening model calculations, Jury et al. 1987a,b; Jury & Ghodrati 1989) 1.61 (soil, quoted, Sabljic 1987) 1.75, 2.00 (quoted, calculated-MCI ., Gerstl & Helling 1987) 2.59 (HPLC-k. correlation, cyanopropyl column, mobile phase buffered to pH 3, Hodson & Williams 1988) 1.00, 1.23, 2.29 (sediment, Alfisol soil, Podzol soil, von Oepen et al. 1991) 1.30–1.78, 1.30–2.0, 1.72 (soil, quoted lit. values, Bottoni & Funari 1992) 1.30, 1.78, 1.51, 1.26, 1.72, 1.75, 1.76 (soil, quoted values, Wauchope et al. 1992) 1.30 (soil, selected, Wauchope et al. 1992) 0.68 (calculated-KOW, Kollig 1993) 1.68–2.73 (Montgomery 1993) 1.66 (calculated-QSAR MCI 1., Sabljic et al. 1995) 2.09, 1.04, 1.40, 0.778 (first generation Eurosoils ES-1, ES-2, ES-3, ES-4, shake flask/batch equilibrium- HPLC/UV, Gawlik et al. 1998, 1999) 1.65, 1.36, 1.37, 0.899 (second generation Eurosoils ES-1, ES-2, ES-3, ES-4, shake flask/batch equilibrium- HPLC/UV, Gawlik et al. 1999) 1.652 (second generation Eurosoil ES-1, HPLC-k. correlation, Gawlik et al. 2000) 1.68 (soil, quoted, Armbrust 2000) 1.79, 1.77 (soils: organic carbon OC . 0.1%, OC . 0.5%, pH 2.8–8.0, average, Delle Site 2001) 2.16, 2.13 (soils: organic carbon OC . 0.1%, OC . 0.5%, pH 2.8–5.0, average, Delle Site 2001) 1.68, 1.68 (soils: organic carbon OC . 0.1%, OC . 0.5%, pH > 5.0, average, Delle Site 2001) Environmental Fate Rate Constants, k, or Half-Lives, t.: Volatilization: volatilization from water is negligible, calculated volatilization t. = 660 d (from 1 cm) and t. = 7.1 yr (from 10 cm) from soil (Howard 1991). © 2006 by Taylor & Francis Group, LLC 3520 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals Photolysis: aqueous photolysis t. = 2–4 d when irradiated at 356 nm, t. = 50 min in water when irradiated at 254 nm and t. = 29–43 d when exposed to September sunlight (Howard 1991); aqueous photolysis rate constant, k = 2.2 . 10–3 h–1 (Armbrust 2000). Oxidation: photooxidation t. = 1.8–18 h, based on estimated rate constant for the vapor-phase reaction with hydroxyl radical in air (Howard et al. 1991) k(aq.) = (1.0–2.3) M–1 s–1 for direct reaction with ozone in water at pH 1.5–2.9 and 21 ± 1°C, with t. = 3.9 h at pH 7 (Yao & Haag 1991). k(calc) = 5.0 . 109 M–1 s–1 (Haag & Yao 1992) kOH(aq.) = 1.6 . 109 M–1 s–1 for reaction with hydroxyl radical in irradiated field water both in the laboratory and sunlit rice paddies (Mabury & Crosby 1996; quoted, Armbrust 2000); kOH(aq.) = 8.4 . 1012 M–1 h–1 at pH 5, 7, 9; measured hydroxyl radical rate constant for 2,4-D, (Armbrust 2000) Hydrolysis: no hydrolyzable groups and rate constant at neutral pH is zero (Kollig et al. 1987; selected, Howard et al. 1991); generally resistant to hydrolysis, may become important at pH > 8 (Howard 1991). Biodegradation: k = 0.7–14.0 d–1 and t. = 10 to > 50 d in clear to murky river water with lag time ranges from 6–12 d (Nesbitt & Watson 1980a); t. = 4 d in river with nutrient and suspended sediments and t. = 10 d with a lag time of 5 d for filtered river water (Nesbitt & Watson 1980b); degradation kinetics not first-order, time for 50% decomposition in six soils: Commerce 5 d, Catlin 1.5 d, Keith 3.9 d, Cecil 3.0 d, Walla-Walla 2.5 d and Fargo 8.5 d, with an average time of 4 d (McCall et al. 1981) aerobic degradation k = 0.3 . 10–3 h–1 with t. = 97.0 d for control system, k = 9.5 . 10–3 h–1 with t. = 3.1 d for metabolism, k = 16.2 . 10–3 h–1 with t. = 1.8 d for co-metabolism; anaerobic degradation k = 0.24 . 10–3 h–1 with t. = 120 d for control system, k = 0.21 . 10–3 h–1 with t. = 135 d for metabolism, k = 0.42 . 10–3 h–1 with t. = 69 d for co-metabolism, by a mixture of microorganisms from activated sludge, soil and sediment in cyclone fermentors (Liu et al. 1981) k = (3.6–28.8) . 10–6 mL cell–1 d–1 in natural water (Paris et al. 1981; quoted, Klecka 1985) k < 0.14–0.07 d–1 in river water at 25°C (Nesbitt & Watson 1980; quoted, Klecka 1985) k = (0.058 ± 0.006) d–1 in lake water at 29°C (Subba-Rao et al. 1982; quoted, Klecka 1985) k = 0.08–0.46 d–1 in soil at 25°C (McCall et al. 1981; quoted, Klecka 1985); t. (aq. aerobic) = 240–1200 h, based on unacclimated aerobic river die-away test data (Nesbitt & Watson 1980; selected, Howard et al. 1991); t. (anaerobic) = 672–4320 h, based on unacclimated aqueous screening test data (Liu et al. 1981; selected, Howard et al. 1991); k = 0.035 d–1 in die-away test, k = 0.029 d–1 in CO2 evolution test, in soil and k = 6.9 . 10–1 mL (g bacteria)–1 d–1 by activated sludge cultures (Scow 1982); t. = 18 to over 50 d in clear river water, and t. = 10 to 25 d in muddy river water with lag times of 6 to 12 d; degradation with a mixture of microorganisms from activated sludge, soil, and sediments lead to half-lives of 1.8–3.1 d under aerobic conditions and 69–135 d under anaerobic conditions (Howard 1991) k(aerobic) = 5.25 . 10–3 h–1 (Armbrust 2000). Biotransformation: Bioconcentration, Uptake (k1) and Elimination (k2) Rate Constants: k1 = 0.0092 h–1; k2 = 0.0092 h–1 (catfish Ictalurus melas, Wang et al. 1996) k1 = 0.8560 h–1; k2 = 0.2690 h–1 (Water flea Daphnia magna, Wang et al. 1996) Half-Lives in the Environment: Air: t. = 1.8–18 h, based on estimated rate constant for the reaction with OH radical (Howard et al. 1991); photooxidation t. = 23.9 h for reactions with OH radical in air (Howard 1991). Surface water: t. = 48–96 h, based on reported photolysis half-lives for aqueous solution irradiated at UV wavelength of 356 nm (Baur & Bovey 1974; selected, Howard et al. 1991); degradation t. = 14 d in sensitized, filtered and sterilized river water, based on sunlight photolysis test of 1 µg mL–1 in distilled water (Zepp et al. 1975; quoted, Cessna & Muir 1991); t. = 1.8 and 3.1 d for cometabolism and metabolism, respectively, easily degraded under aerobic conditions; t. = 69 and 135 d under anaerobic conditions (Liu et al. 1981;) © 2006 by Taylor & Francis Group, LLC Herbicides 3521 typical biodegradation t. = 10 to < 50 d with longer expected in oligotrophic waters, photolysis t. = 29–43 d for water solutions irradiated at sunlight (Howard 1991); degraded relatively slowly when incubated in natural waters or in soil/sediment suspensions, with t. ~ 6 to 170 d (Muir 1991); rate constant k(exptl) = (1.0–2.3) M–1 s–1 for direct reaction with ozone in water at pH 1.5–2.9 and 21°C, with t. = 3.9 h at pH 7 (Yao & Haag 1991); rate constant k(calc) = 5 . 109 M–1 s–1 for the reaction with hydroxyl radical in aqueous solution (Haag & Yao 1992); t. = 2–4 d when irradiated at . = 356 nm in aqueous solution (Montgomery 1993). Ground water: t. = 480–4320 h, based on estimated unacclimated aqueous aerobic and anaerobic biodegradation half-lives (Howard et al. 1991) reported t. = 4, 15, 1–35, 7–21 d (Bottoni & Funari 1992) Sediment: t. < 1 d for degradation in sediments and lake muds (Howard 1991); degraded relatively slowly when incubated in natural waters or in soil/sediment suspensions, with t. = 6 to 170 d (Muir 1991). Soil: degradation t. = 5.0 and 4.0 d in Quachita Highlands’ forest and grassland soil respectively, t. = 4 d in Gross Timbers Forest soil, average t. = 4 d in 3 soils (shake flask, Altom & Stritzke 1973); field t. = 5.2 d in Arid range (Lane et al. 1977; quoted, Nash 1983); field t. = 19 d in Dykland soil (Stewart & Gaul 1977; quoted, Nash 1983); lab. t. = 5.5 d in Naff soil (Wilson & Cheng 1978; quoted, Nash 1983); microagroecosystem t. = 11 d for granular application to bluegrass turf (Nash & Beall 1980) non-persistent in soil with t. < 20 d (Willis & McDowell 1982); microagroecosystem t. = 3 d in moist fallow soil (Nash 1983); t. = 15 d in soil (Jury et al. 1983, 1987a,b; Jury & Ghodrati 1989); persistence of one month in soil (Jury et al. 1987); t. = 240–1200 h, based on estimated unacclimated aqueous aerobic biodegradation half-life (Howard et al. 1991); biodegradation t. < 1 d to several weeks, t. = 3.9 and 11.5 d in 2 moist soils and t. = 9.4 to 254 d in the same soils under dry conditions (Howard 1991); degraded relatively slowly when incubated in natural waters or in soil/sediment suspensions, with t. = 6 to 170 d (Muir 1991); reported t. = 4,15, 1–35 and 7–21 d (Bottoni & Funari 1992); field t. = 2–16 d, with a selected value of 10 d (Wauchope et al. 1992); soil t. = 18 d (Pait et al. 1992); rate constants for Amsterdam silt loam at soil depth 0–30 cm: k = 0.0053 d–1 at 10°C, k = 0.0046 d–1 at 17°C and k = 0.0127 d–1 at 24°C with corresponding first-order t. = 7, 7, and 2 d; at soil depth 30–60 cm: k = 0.00012 d–1 at 10°C, k = 0.0044 d–1 at 17°C and k = 0.0077 d–1 at 24°C with corresponding first-order t. = 273, 8, and 4 d; and at soil depth 60–120 cm: k = 0.00005 d–1 at 10°C, k = 0.0013 d–1 at 17°C and k = 0.0022 d–1 at 24°C with corresponding first-order t. = 593, 25, and 12 d (Veeh et al. 1996). Biota: depuration t. = 13.8 h in daphnids, t. = 1.32 d in catfish (Ellgehausen et al. 1980). © 2006 by Taylor & Francis Group, LLC 3522 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals 17.1.1.22 Dalapon Common Name: Dalapon Synonym: Alatex, Basinex P, Crisapon, D-Granulat, Dawpon-Rae, Ded-Weed, Dowpon, DPA, Gramevin, Kenapon, Liropon, Proprop, Radapon Chemical Name: 2,2-dichloropropanoic acid; 2,2-dichloropropionic acid; .-dichloropropanoic acid; .,.-dichloropropionic acid Uses: selective systemic herbicide to control perennial and annual grasses on noncropland, fruits, vegetables, and some aquatic weeds. CAS Registry No: 75-99-0 Molecular Formula: C3H4Cl2O2 Molecular Weight: 1432.969 Melting Point (°C): liquid Boiling Point (°C): 185–190 (Herbicide Handbook 1989; Worthing & Hance 1991; Tomlin 1994) 98–99 (sodium salt at 20 mmHg, Budavari 1989) Density (g/cm3 at 20°C): 1.389 (Nelson & Faust 1969; quoted, Kenaga 1974; Montgomery 1993) 1.389 (22.8°C, Herbicide Handbook 1989) 1.4014 (Budavari 1989; Milne 1995) Molar Volume (cm3/mol): Dissociation Constant pKa: 1.84 (potentiometric titration, Nelson & Faust 1969; Freed 1976; Hornsby et al. 1996) 1.74 (Kenaga 1974; quoted, Howard 1991) 1.74–1.84 (Worthing & Hance 1991; Tomlin 1994) 2.06 (Yao & Haag 1991; Haag & Yao 1992) 1.84 (free acid, Montgomery 1993) Enthalpy of Fusion, .Hfus (kJ/mol): Entropy of Fusion, .Sfus (J/mol K): Fugacity Ratio at 25°C (assuming .Sfus = 56 J/mol K), F: 1.0 Water Solubility (g/m3 or mg/L at 25°C or as indicated): 900000 (Woodford & Evans 1963; Bailey & White 1965) > 800000 (Kenaga 1974) 502000 (Martin & Worthing 1977) 450000 (Weber et al. 1980; Budavari 1989) 501200 (Garten & Trabalka 1983) 431850 (selected, Gerstl & Helling 1987) 900000 (sodium salt, Worthing & Walker 1987, Worthing & Hance 1991) 500000 (Reinert 1989) 450000–900000 (Montgomery 1993) 900000 (20–25°C, selected, Hornsby et al. 1996) Vapor Pressure (Pa at 25°C or as indicated): 16.0 (calculated from high temp., Foy 1976) 1.0 . 10–5 (Worthing & Hance 1991; Tomlin 1994) 0.0 (20–25°C, selected, Hornsby et al. 1996) Henry’s Law Constant (Pa·m3/mol at 25°C): 6.50 . 10–3 (Hine & Mookerjee 1975) 0.608 (calculated, Montgomery 1993) OH O Cl Cl © 2006 by Taylor & Francis Group, LLC Herbicides 3523 4.56 . 10–3 (calculated-P/C as per Howard 1991, Majewski & Capel 1995) Octanol/Water Partition Coefficient, log KOW: 0.76 (Kenaga 1974) 0.78 (Kenaga 1980) 1.34 (selected, Dao et al. 1983) –2.76 (selected, Gerstl & Helling 1987) 1.48 (Reinert 1989) 0.78 (selected, Hansch et al. 1995) 1.47 (LOGSTAR or CLOGP data, Sabljic et al. 1995) Octanol/Air Partition Coefficient, log KOA: Bioconcentration Factor, log BCF: 0.477 (dalapon sodium salt in fish, Kenaga 1974) –0.444 (calculated-S, Kenaga 1980; quoted, Isensee 1991) 0.301 (estimated-KOW, Lyman et al. 1982; quoted, Howard 1991) Sorption Partition Coefficient, log KOC: 0.477 (soil, calculated-S as per Kenaga & Goring 1980, Kenaga 1980) 0.97 (calculated-MCI ., Gerstl & Helling 1987) 2.13 (Reinert 1989) 0.48, 2.13 (soil, quoted values, Bottoni & Funari 1992) 0.27–2.18 (calculated, Montgomery 1993) 0.40 (soil, calculated-MCI 1., Sabljic et al. 1995) 0.0 (soil, 20–25°C, selected, Hornsby et al. 1996) Environmental Fate Rate Constants, k, or Half-Lives, t.: Volatilization: Photolysis: Oxidation: photooxidation t. = 289–2893 h in air, based on an estimated rate constant for the vapor-phase reaction with hydroxyl radical in air (Atkinson 1987; quoted, Howard et al. 1991); k(aq.) = 4.6 . 108 M–1 s–1 for the reaction (photo-Fenton with reference to acetophenone) with hydroxyl radical in aqueous solutions at pH 3.4 and at 24 ± 1°C (Buxton et al. 1988; quoted, Faust & Hoigne 1990; Haag & Yao 1992) k(aq.) . 0.005 M–1 s–1 for direct reaction with ozone in water at pH 6.4 and 22°C, with a half-life of > 2 yr at pH 7 (Yao & Haag 1991). k(aq.) = (7.3 ± 0.3) . 107 M–1 s–1 for the reaction (photo-Fenton with reference to acetophenone) with hydroxyl radical in aqueous solutions at pH 3.4 and at 24 ± 1°C (Haag & Yao 1992). Hydrolysis: Biodegradation: aqueous aerobic t. = 336–1440 h, based on unacclimated aerobic soil grab sample data (Corbin & Upchurch 1967; Kaufman & Doyle 1977; quoted, Howard et al. 1991); rate constant k = 0.047 d–1 by soil incubation die-away studies (Rao & Davidson 1980; quoted, Scow 1982); aqueous anaerobic t. = 1344–5760 h, based on estimated aqueous aerobic biodegradation half-life (Howard et al. 1991). Biotransformation: Bioconcentration, Uptake (k1) and Elimination (k2) Rate Constants: Half-Lives in the Environment: Air: t. = 289–2893 h, based on an estimated rate constant for the vapor-phase reaction with hydroxyl radical in air (Atkinson 1987; quoted, Howard et al. 1991). Surface water: t. = 336–1440 h, based on estimated aqueous aerobic biodegradation half-life (Howard et al. 1991); © 2006 by Taylor & Francis Group, LLC 3524 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals measured rate constant k . 0.0005 M–1 s–1 for direct reaction with ozone in water at pH 6.4 and 22°C, with a t. . 2 yr at pH 7 (Yao & Haag 1991). Groundwater: t. = 672–2880 h, based on estimated aqueous aerobic biodegradation half-life (Howard et al. 1991). reported t. = 30 d (Bottoni & Funari 1992) Sediment: Soil: t. = 7–8 d in soil (Kaufman 1966; quoted, Kaufman 1976); persistence across 43 soils from < 2 wk to > 8 wk (Day et al. 1963; quoted, Kaufman 1976); t. = 336–1440 h, based on unacclimated aerobic soil grab sample data (Corbin & Upchurch 1967; Kaufman & Doyle 1977; quoted, Howard et al. 1991); estimated persistence of 8 months (Kearney et al. 1969; quoted, Jury et al. 1987); persistence of 8 wk in soil (Edwards 1973; quoted, Morrill et al. 1982); persistence of about 2 wk in growing season in most agricultural soils (Herbicide Handbook 1974; quoted, Kaufman 1976); estimated first-order t. = 15 d from biodegradation rate constant k = 0.047 d–1 by soil incubation die-away studies (Rao & Davidson 1980; quoted, Scow 1982); non-persistent in soil with t. < 20 d (Willis & McDowell 1982); reported half-life or persistence, 30 d (Verschuren 1983; Bottoni & Funari 1992); field t. = 30 d at 20–25°C (selected, Hornsby et al. 1996). Biota: © 2006 by Taylor & Francis Group, LLC Herbicides 3525 17.1.1.23 2,4-DB Common Name: 2,4-DB Synonym: Butoxon, Butyrac, Butyrac 118, Embutox, Legumex D Chemical Name: 4-(2,4-dichlorophenoxy)butanoic acid; 4-(2,4-dichlorophenoxy)butyric acid Uses: herbicide for post-emergence control of many annual and perennial broadleaf weeds in lucerne, clovers, undersown cereals, grassland, forage legumes, soybeans, and groundnuts. CAS Registry No: 94-82-6 Molecular Formula: C10H10Cl2O3 Molecular Weight: 249.090 Melting Point (°C): 118 (Lide 2003) Boiling Point (°C): Density (g/cm3 at 20°C): Molar Volume (cm3/mol): 254.2 (calculate-Le Bas method at normal boiling point) Dissociation Constant pKa: 5.95 (Bailey & White 1965; Que Hee et al. 1981) 4.80 (Worthing & Walker 1987; Hornsby et al. 1996) Enthalpy of Vaporization, .HV (kJ/mol): 91.29 (Rordorf 1989) Enthalpy of Fusion, .Hfus (kJ/mol): 33.6 (Rordorf 1989) Entropy of Fusion, .Sfus (J/mol K): Fugacity Ratio at 25°C (assuming .Sfus = 56 J/mol K), F: 0.122 (mp at 118°C) Water Solubility (g/m3 or mg/L at 25°C or as indicated): 82.3 (Bailey & White 1965) 53 (rm. temp., Melnikov 1971) 46 (Martin & Worthing 1977; Worthing & Walker 1987, Worthing & Hance 1991) 46 (Weber et al. 1980) 46 (Hartley & Kidd 1987; Budavari 1989;, Milne 1995) 46 (20–25°C, selected, Hornsby et al. 1996) Vapor Pressure (Pa at 25°C or as indicated and reported temperature dependence equations): negligible (Hartley & Kidd 1987) 1.0 . 10–5, 5.90 . 10–4, 0.019, 0.38, 5.20 (25, 50, 70, 100, 125°C, gas saturation-GC, Rordorf 1989) log (PS/Pa) = 17.692 – 6760.5/(T/K); measured range 80–120°C (solid, gas saturation-GC, Rordorf 1989) log (PL/Pa) = 12.682 – 4768.7/(T/K); measured range 125–196°C (liquid, gas saturation-GC, Rordorf 1989) Henry’s Law Constant (Pa·m3/mol): Octanol/Water Partition Coefficient, log KOW: 3.53 (shake flask-HPLC/UV, Jafvert et al. 1990) 3.53 (selected, Hansch et al. 1995) Octanol/Air Partition Coefficient, log KOA: Bioconcentration Factor, log BCF: 1.85 (calculated-S, Kenaga 1980) 2.21 (calculated-log KOW as per Mackay 1982, this work) Cl Cl O OH O © 2006 by Taylor & Francis Group, LLC 3526 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals Sorption Partition Coefficient, log KOC: 2.72 (soil, calculated-S, Kenaga 1980) 1.3 (organic carbon, Wauchope et al. 1991) 2.64 (20–25°C, estimated, Hornsby et al. 1996) Environmental Fate Rate Constants, k, or Half-Lives, t.: Volatilization: Photolysis: Oxidation: photooxidation t. = 6–60 h in air, based on an estimated rate constant for the vapor-phase reaction with hydroxyl radicals in air (Atkinson 1987; quoted, Howard et al. 1991). Hydrolysis: stable in distilled water for 40 d (Chau & Thomson 1978; quoted, Howard et al. 1991). Biodegradation: aqueous aerobic t. = 24–168 h, based on unacclimated soil grab sample data (Smith 1978; quoted, Howard et al. 1991); aqueous anaerobic t. = 96–672 h, based on estimated unacclimated aqueous aerobic biodegradation half-life (Howard et al. 1991). Biotransformation: Bioconcentration, Uptake (k1) and Elimination (k2) Rate Constants: Half-Lives in the Environment: Air: t. = 6–60 h, based on an estimated rate constant for the vapor-phase reaction with hydroxyl radicals in air (Atkinson 1987; Howard et al. 1991). Surface water: t. = 24–168 h, based on estimated unacclimated aqueous aerobic biodegradation half-life (Howard et al. 1991). Groundwater: t. = 48–336 h, based on estimated unacclimated aqueous aerobic biodegradation half-life (Howard et al. 1991) reported t. < 7 d (Bottoni & Funari 1992) Sediment: Soil: t. = 24–168 h, based on unacclimated soil grab sample data (Smith 1978; quoted, Howard et al. 1991) selected t. = 10 d (Wauchope et al. 1991; quoted, Dowd et al. 1993); t. < 7 d (Worthing & Hance 1991; Bottoni & Funari 1992); field t. = 5 d (20–25°C, selected, Hornsby et al. 1996). Biota: © 2006 by Taylor & Francis Group, LLC Herbicides 3527 17.1.1.24 Diallate Common Name: Diallate Synonym: Avadex, CP 15336, DATC, Pyradex Chemical Name: S-(2,3-dichloroallyl)diisopropyl(thiocarbamate); S-(2,3-dichloro-2-propenyl)bis(1-methylethyl)- carbamothioate Uses: pre-emergent and selective herbicide to control wild oats and blackgrass in barley, corn, flax, lentils, peas, potatoes, soybeans, and sugar beets. CAS Registry No: 2303-16-4 Molecular Formula: C10H17Cl2NOS Molecular Weight: 270.219 Melting Point (°C): 25–30 (Herbicide Handbook 1989; Montgomery 1993) Boiling Point (°C): 97 (at 0.15 mmHg, Herbicide Handbook 1989) 108 (at 0.25 mmHg, Herbicide Handbook 1989; Montgomery 1993) 150 (at 9 mmHg, Howard 1991; Milne 1995; Montgomery 1993) Density (g/cm3 at 20°C): 1.188 (25°C, Hartley & Kidd 1987; Montgomery 1993) Molar Volume (cm3/mol): 305.1 (calculated-Le Bas method at normal boiling point) Dissociation Constant pKa: Enthalpy of Fusion, .Hfus (kJ/mol): Entropy of Fusion, .Sfus (J/mol K): Fugacity Ratio at 25°C (assuming .Sfus = 56 J/mol K), F: Water Solubility (g/m3 or mg/L at 25°C or as indicated): 40.0 (Gunther et al. 1968) 14.0 (Ashton & Crafts 1973, 1981) 40.0 (rm. temp., Spencer 1973; Khan 1980) 40.0 (Martin & Worthing 1977; Hartley & Kidd 1987; Montgomery 1993; Milne 1995) 14.0 (Herbicide Handbook 1978; Herbicide Handbook 1989; Montgomery 1993) 68.8 (22°C, shake flask-GC, Bowman & Sans 1979, 1983a,b) 40.5 (20–25°C, shake flask-GC, Kanazawa 1981) 52.5 (Garten & Trabalka 1983) 14.0 (20–25°C, selected, Augustijn-Beckers et al. 1994; Hornsby et al. 1996) Vapor Pressure (Pa at 25°C or as indicated): 0.020 (Ashton & Crafts 1973; Herbicide Handbook 1989) 0.0117 (20°C, Hartley & Graham-Bryce 1980) 0.0337 (20°C, GC-RT correlation, Kim 1985) 0.020 (Hartley & Kidd 1987) 0.013 (20°C, selected, Suntio et al. 1988) 0.020 (20°C, Montgomery 1993) 0.020 (20–25°C, selected, Augustijn-Beckers et al. 1994; Hornsby et al. 1996) Henry’s Law Constant (Pa·m3/mol at 25°C or as indicated): 0.250 (20°C, calculated-P/C, Suntio et al. 1988) 0.385 (calculated-P/C, Howard 1991) 0.253 (20–25°C, calculated-P/C, Montgomery 1993) CClCH2S N O ClCH © 2006 by Taylor & Francis Group, LLC 3528 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals 0.108 (calculated-P/C, this work) Octanol/Water Partition Coefficient, log KOW: 5.23 (estimated, USEPA 1988; quoted, Howard 1991) 3.29 (calculated, Montgomery 1993) 3.67 (LOGPSTAR or CLOGP data, Sabljic et al. 1995) Octanol/Air Partition Coefficient, log KOA: Bioconcentration Factor, log BCF: 2.15 (calculated-S, Kenaga 1980; quoted, Howard 1991; Isensee 1991) 2.08 (calculated-KOC, Kenaga 1980) Sorption Partition Coefficient, log KOC: 3.28 (soil, Grover 1974) 2.96. 2.46, 2.59, 2.49, 2.65 (Melfort loam, Weyburn sandy loam, Regina clay, Indian Head sandy loam, Asquith loamy sand, Grover et al. 1979) 3.28 (soil, measured value, Kenaga 1980; Kenaga & Goring 1980) 3.00 (soil, calculated-S as per Kenaga & Goring 1980, Kenaga 1980) 2.77 (calculated-MCI ., Bahnick & Doucette 1988) 2.28 (Montgomery 1993) 3.52 (selected, Lohninger 1994) 2.70 (20–25°C, selected, Augustijn-Beckers et al. 1994; Hornsby et al. 1996) 3.28 (soil, calculated-MCI 1., Sabljic et al. 1995) 3.28; 3.21, 2.66 (soil, cis-isomer, quoted exptl.; estimated-class-specific model, estimated-general model using molecular descriptors, Gramatica et al. 2000) 3.28; 3.21, 2.65 (soil, trans-isomer, quoted exptl.; estimated-class-specific model, estimated-general model using molecular descriptors, Gramatica et al. 2000) Environmental Fate Rate Constants, k, or Half-Lives, t.: Volatilization: Photolysis: t. = 4 h, < 1% of 135 µg/mL to degrade in distilled water under > 300 nm light (Ruzo & Casida 1985; quoted, Cessna & Muir 1991). Oxidation: photooxidation t. = 0.58–5.8 h, based on an estimated rate constant for the vapor-phase reaction with hydroxyl radicals in air (Atkinson 1987; quoted, Howard et al. 1991). Hydrolysis: neutral hydrolysis rate constant k = (1.2 ± 0.7) . 10–5 h–1 with a calculated first-order t. = 6.6 yr at pH 7 (Ellington et al. 1987, 1988); first-order t. = 6.6 yr, based on measured first-order base catalyzed hydrolysis rate constant at pH 7 (Ellington et al. 1987; quoted, Howard et al. 1991) t. = 2400 d at pH 2, t. = 2500 d at pH 7 and t. = 32 d at pH 12 in natural waters (Capel & Larson 1995). Biodegradation: aqueous aerobic t. = 252–2160 h, based on aerobic soil die-away test data (Anderson & Domsch 1976; Smith 1970; quoted, Howard et al. 1991); aqueous anaerobic t. = 1008–8640 h, based on aerobic soil die-away test data (Anderson & Domsch 1976; Smith 1970; quoted, Howard et al. 1991) t.(aerobic) = 11 d, t.(anaerobic) = 42 d in natural waters (Capel & Larson 1995) Biotransformation: Bioconcentration, Uptake (k1) and Elimination (k2) Rate Constants: Half-Lives in the Environment: Air: t. = 0.58–5.8 h, based on an estimated rate constant for the vapor-phase reaction with hydroxyl radicals in air (Atkinson 1987; quoted, Howard et al. 1991). Surface water: t. = 252–2160 h, based on aerobic soil die-away test data (Anderson & Domsch 1976; Smith 1970; quoted, Howard et al. 1991) Biodegradation t.(aerobic) = 11 d, t.(anaerobic) = 42 d, hydrolysis t. = 2400 d at pH 2, t. = 2500 d at pH 7 and t. = 32 d at pH 12 in natural waters (Capel & Larson 1995) © 2006 by Taylor & Francis Group, LLC Herbicides 3529 Ground water: t. = 504–4320 h, based on aerobic soil die-away test data (Anderson & Domsch 1976; Smith 1970; quoted, Howard et al. 1991). Sediment: Soil: t. = 252–2160 h, based on aerobic soil die-away test data (Anderson & Domsch 1976; Smith 1970; quoted, Howard et al. 1991; Montgomery 1993); t. = 30 d (Hartley & Kidd 1987; quoted, Montgomery 1993); selected field t. = 30 d (Augustijn-Beckers et al. 1994; Hornsby et al. 1996). Biota: © 2006 by Taylor & Francis Group, LLC 3530 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals 17.1.1.25 Dicamba Common Name: Dicamba Synonym: Banex, Banvel, Banvel D, Brush buster, Dianat, MDBA, Mediben Chemical Name: 3,6-dichloro-2-methoxybenzoic acid; 3,6-dichloro-o-anisic acid Uses: systemic pre-emergent and post-emergent herbicide to control both annual and perennial broadleaf weeds. CAS Registry No: 1918-00-9 Molecular Formula: C8H6Cl2O3 Molecular Weight: 221.038 Melting Point (°C): 115 (Lide 2003) Boiling Point (°C): Density (g/cm3 at 20°C): 1.570 (25°C, Hartley & Kid 1987; Worthing & Hance 1991; Montgomery 1993; Tomlin 1994; Milne 1995) Molar Volume (cm3/mol): 207.9 (calculated-Le Bas method at normal boiling point) Dissociation Constant pKa: 1.94 (Kearney & Kaufman 1975; Spencer 1982; Lee et al. 1993) 1.90 (Cessna & Grover 1978; Weber et al. 1980; Willis & McDowell 1982; Howard 1991; Montgomery 1993; Armbrust 2000) 1.95 (Worthing & Hance 1991; Montgomery 1993; Caux et al. 1993) 1.87 (Tomlin 1994) 1.91 (Hornsby et al. 1996) Enthalpy of Vaporization, .HV (kJ/mol): 77.85 (Rordorf 1989) Enthalpy of Fusion, .Hfus (kJ/mol): 22.59 (DSC method, Plato & Glasgow 1969) 19.1 (Rordorf 1989) Entropy of Fusion, .Sfus (J/mol K): Fugacity Ratio at 25°C (assuming .Sfus = 56 J/mol K), F: 0.131 (mp at 115°C) Water Solubility (g/m3 or mg/L at 25°C or as indicated): 7900 (Freed 1966; Verschueren 1983) 4500 (Martin & Worthing 1977; quoted, Kenaga 1980; Kenaga & Goring 1980; Khan 1980; Ashton & Crafts 1981; Weber et al. 1980; Hartley & Graham-Bryce 1980) 6500 (Hartley & Kidd 1987; Herbicide Handbook 1989; Caux et al. 1993) 6500 (Worthing & Walker 1987, Worthing & Hance 1991; Montgomery 1993; Tomlin 1994; Milne 1995) 5600 (20°C, selected, Suntio et al. 1988) 4410, 221 (quoted, calculated-group contribution fragmentation method, Kuhne et al. 1995) 8310 (selected., Armbrust 2000) Vapor Pressure (Pa at 25°C or as indicated and reported temperature dependence equations): 0.00454 (Ashton & Crafts 1973; 1981) 0.00267 (Baur & Bovey 1974; Spencer 1976) 0.49 (20°C, Hartley & Graham-Bryce 1980; Khan 1980) < 0.00013 (20–25°C, Weber et al. 1980; Willis & McDowell 1982) 0.00453 (Herbicide Handbook 1983, 1989; Worthing & Hance 1991) 0.0045 (Hartley & Kidd 1987; Tomlin 1994) 0.50 (100°C, Budavari 1989) 2.90 . 10–3, 6.40 . 10–2, 0.88, 8.60, 63.0 (25, 50, 70, 100, 125°C, gas saturation-GC, Rordorf 1989) O OH O Cl Cl © 2006 by Taylor & Francis Group, LLC Herbicides 3531 log (PS/Pa) = 14.706 – 5139.1/(T/K); measured range 60.1–110°C (solid, gas saturation-GC, Rordorf 1989) log (PL/Pa) = 11.911 – 4067.0/(T/K); measured range 115–176°C (liquid, gas saturation-GC, Rordorf 1989) 0.50 (20°C, selected, Taylor & Spencer 1990) 0.0045 (20°C, Montgomery 1993) Henry’s Law Constant (Pa·m3/mol at 25°C or as indicated): 0.00012 (20°C, calculated-P/C, Suntio et al. 1988) 0.0248 (calculated-P/C, Taylor & Glotfelty 1988) 0.0918 (Suntio et al. 1988; quoted, Howard 1991; Majewski & Capel 1995) 2.2 . 10–5 (calculated-P/C, Nash 1989) 1.22 . 10–4 (20–25°C, calculated-P/C, Montgomery 1993) 0.00012, 0.000154 (20, 25°C, quoted, Caux et al. 1993) 4.46 . 10–5 (quoted lit., Armbrust 2000) Octanol/Water Partition Coefficient, log KOW: 0.477 (Rao & Davidson 1980) 2.41 (selected, Dao et al. 1983) 2.21 (shake flask, Log P Database, Hansch & Leo 1985, 1987) –1.69 (selected, Gerstl & Helling 1987) 3.01 (selected, Travis & Arms 1988) 2.46 (Reinert 1989) 2.49 (shake flask-HPLC/UV, Jafvert et al. 1990) 2.46 (EPA Environmental Fate one-liner database Version 3.04, Lee et al. 1993) 2.21 (recommended, Sangster 1993) 0.48 (Montgomery 1993) –0.80 (pH 7, Tomlin 1994) 2.21 (recommended, Hansch et al. 1995) Bioconcentration Factor, log BCF: 0.699 (calculated-S, Kenaga 1980) –2.00 (calculated-KOC, Kenaga 1980) –4.58 (beef biotransfer factor logBb, correlated-KOW, Oehler & Ivie 1980) –4.60 (milk biotransfer factor logBm, correlated-KOW, Oehler & Ivie 1980) 1.450 (estimated-KOW per Hansch & Leo 1985, Lyman et al. 1982) 0.903 (estimated-S per Suntio et al. 1988, Lyman et al. 1982) Sorption Partition Coefficient, log KOC: –0.398 (soil, quoted exptl., Kenaga 1980) 1.63 (soil, calculated-S as per Kenaga & Goring 1980, Kenaga 1980) 0.342 (av. soils/sediments, Rao & Davidson 1980) –0.40, 2.08 (quoted, calculated-MCI ., Gerstl & Helling 1987) 0.34 (soil, screening model calculations, Jury et al. 1987b) 2.67 (KOC = 470 reported, Reinert 1989) 0.643 (soil, estimated, Shirmohammadi et al. 1989) –1.00 (selected, USDA 1989; quoted, Neary et al. 1993) 0.30 (organic carbon, Wauchope et al. 1991) –0.40, 1.62, 0.18, 0.34 (soil, quoted values, Bottoni & Funari 1992) 1.50; 1.46 (soil, quoted exptl.; calculated-MCI . and fragment contribution Meylan et al. 1992) –0.40, 0.34 (Montgomery 1993) 0.30 (Tomlin 1994) 1.50 (quoted or calculated-QSAR MCI 1., Sabljic et al. 1995) 1.114 (quoted lit., Armbrust 2000) Sorption Partition Coefficient, log KOM: 2.74 (organo-clay DODMA140-SAz, sorption isotherm, Zhao et al. 1996) © 2006 by Taylor & Francis Group, LLC 3532 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals 2.57 (organo-clay DODMA-SAz, sorption isotherm-HPLC/UV, Zhao et al. 1996) 2.48 (organo-clay HDTMA-SAz, sorption isotherm-HPLC/UV, Zhao et al. 1996) 2.59 (organo-clay HDTMA-SWy, sorption isotherm-HPLC/UV, Zhao et al. 1996) Environmental Fate Rate Constants, k, or Half-Lives, t.: Volatilization: Photolysis: aqueous photolysis rate constant k = 7.5 . 10–4 h–1 (Armbrust 2000). Oxidation: photooxidation t. = 2.4–6.0 d, based on estimated rate constant for the vapor-phase reaction with hydroxyl radicals in the atmosphere (Atkinson 1985; quoted, Howard 1991); measured hydroxy radical reaction rate constant for dicamba 4.8 . 1012 M–1 /h (Armbrust 2000). Hydrolysis: t. > 133 d for 2 µg mL–1 to hydrolyze in dark sterile pond water at 37–39°C (Scifres et al. 1973; quoted, Muir 1991); stable aqueous hydrolysis rates at pH 5, 7, 9 (Armbrust 2000). Biodegradation: t. = 60 d to > 160 d for 100 µg mL–1 to degrade in pond sediment/water under lighted conditions at 20–30°C (Scifres et al. 1973; quoted, Muir 1991); under lab. conditions using nonsterile sandy loam, silty clay, or heavy clay soil, 50% of applied dicamba degraded within 2 weeks; however in sterilized (via heating) soil, over 90% of applied dicamba was recovered after 4 weeks, suggesting that microbes were responsible for the decomposition (Smith 1973; quoted, Howard 1991); t. > 25 d for 5.85 mg of labeled dicamba to plants to degrade following washoff from plants and sands in model ecosystem (derived from data of Yu et al. 1975; Muir 1991); k = 0.022 d–1 by soil incubation die-away studies (Rao & Davidson 1980; quoted, Scow 1982); rate of biodegradation in soil generally increases with temperature and soil moisture (up to 50%) and tends to be faster when the soil is slightly acidic (Herbicide Handbook 1983; quoted, Howard 1991); aerobic rate constant k = 1.60 . 10–3 h–1 (Armbrust 2000). Biotransformation: Bioconcentration, Uptake (k1) and Elimination (k2) Rate Constants: Half-Lives in the Environment: Air: t. ~ 2.42 d for reaction with hydroxyl radicals (estimated, Eisenreich et al. 1981; quoted, Caux et al. 1993 t. = 2.42–6.0 d, based on estimated rate constant for the vapor-phase reaction with hydroxyl radicals in the atmosphere (Atkinson 1985; quoted, Howard 1991). Surface water: Ground water: t. = 23.5 d determined under batch conditions at 28°C, t. = 38 d at 20°C, and t. = 151 d at 12°C and were all higher than t. ~ 13.5 d from the decrease in column effluent concentrations over time (Comfort et al. 1992); reported t. = 14–433, 201 and 25 d (Bottoni & Funari 1992) t. < 7 d in surface water (Caux et al. 1993). Sediment: Soil: estimated persistence of 2 months (Kearney et al. 1969; quoted, Jury et al. 1987a); t. = 59, 19, and 17 d with disappearance rates: k = 0.0117, 0.036 and 0.041 d–1 at pH 4.3, 5.3 and 6.5 (Hamaker 1972; quoted, Nash 1988); persistence of 2 months in soil (Edwards 1973; quoted, Morrill et al. 1982); degradation t. = 32 d and 17 d in Quachita Highlands = forest and grassland soil respectively, t. = 26 d in Gross Timbers Forest soil, average t. = 25 d in 3 soils (Altom & Stritzke 1973); first-order t. ~ 31.5 d in soil from biodegradation rate constant k = 0.022 d–1 by soil incubation die-away studies (Rao & Davidson 1980; quoted, Scow 1982); nonpersistent in soils with t. < 20 d (Willis & McDowell 1982); mean t. = 14 d under lab. conditions from review of persistence literature, while the mean t. = 8 d under field conditions (Rao & Davidson 1982; quoted, Howard 1991); non-persistent with t. < 20 d in soil (Willis & McDowell 1982); t. = 14 d from screening model calculations (Jury et al. 1987b); t. < 14 d under conditions amenable to rapid metabolism (Herbicide Handbook 1989); selected t. = 14 d (Wauchope et al. 1991; quoted, Dowd et al. 1993); t. < 14–25 d (Worthing & Hance 1991; quoted, Montgomery 1993); © 2006 by Taylor & Francis Group, LLC Herbicides 3533 reported t. = 20 d, 25 d and 14–433 d (Bottoni & Funari 1992); t. = 4–555 d with a mean t. = 24 d (Caux et al. 1993); t. < 14 d (Tomlin 1994). Biota: biochemical t. = 14 d from screening model calculations (Jury et al. 1987b); average t. = 25 d in the forest (USDA 1989; quoted, Neary et al. 1993); biological t. = 0.64 h (Caux et al. 1993). © 2006 by Taylor & Francis Group, LLC 3534 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals 17.1.1.26 Dichlobenil Common Name: Dichlobenil Synonym: Barrier 2G, Barrier 50W, Casoron, DBN, DCB, Decabane, Du-Sprex, Dyclomec, NIA 5996, Niagara 5006, Niagara 5996, Norosac Chemical Name: 2,6-dichlorobenzonitrile Uses: soil applied herbicide to control many annual and perennial broadleaf weeds. CAS Registry No: 1194-65-6 Molecular Formula: C7H3Cl2N Molecular Weight: 172.012 Melting Point (°C): 144.5 (Lide 2003) Boiling Point (°C): 270 (Verloop 1972; Khan 1980; Worthing & Hance 1991; Tomlin 1994; Milne 1995) Density (g/cm3 at 20°C): > 1.0 (Milne 1995) Molar Volume (cm3/mol): 148.9 (calculated-Le Bas method at normal boiling point) Dissociation Constant pKa: Enthalpy of Vaporization, .HV (kJ/mol): 65.74 (Rordorf 1989) Enthalpy of Fusion, .Hfus (kJ/mol): 25.94 (DSC method, Plato & Glasgow 1969) 34.33 (Verloop 1972) 24.2 (Rordorf 1989) Entropy of Fusion, .Sfus (J/mol K): Fugacity Ratio at 25°C (assuming .Sfus = 56 J/mol K), F: 0.0672 (mp at 144.5°C) Water Solubility (g/m3 or mg/L at 25°C or as indicated): 18 (20°C, Gunther et al. 1968; Weber 1972; Verloop 1972; Spencer 1982; Verschueren 1983) 25 (Gunther et al. 1968; Montgomery 1993) 18 (Martin & Worthing 1977; Herbicide Handbook 1978) 18 (Wauchope 1978; Khan 1980; Burkhard & Guth 1981) 18 (20°C, Ashton & Crafts 1981; Hartley & Kidd 1987; Herbicide Handbook 1989) 18 (20°C, Worthing & Walker 1987, Worthing & Hance 1991; Tomlin 1994) 21.2 (20–25°C, selected, Wauchope et al. 1992; Lohninger 1994; Hornsby et al. 1996) 18, 25 (20°C, 25°C, Milne 1995) Vapor Pressure (Pa at 25°C or as indicated and reported temperature dependence equations): 0.072 (20°C, effusion manometer technique, Barnsley & Rosher 1961) 0.0733 (20°C, Verloop 1972; Khan 1980; Ashton & Crafts 1981; Herbicide Handbook 1989) 0.0667 (20°C, Weber 1972; Worthing & Walker 1987) 0.0004 (20°C, Spencer 1976) 0.0666 (20°C, effusion method, Spencer 1976) 0.0733 (20–25°C, Weber et al. 1980) 0.073 (20°C, Hartley & Kidd 1987) 0.070 (20°C, selected, Suntio et al. 1988) 0.110, 1.80, 20.0, 160, 970 (25, 50, 70, 100, 125°C, gas saturation-GC, Rordorf 1989) log (PS/Pa) = 14.787 – 4698.2/(T/K); measured range 32.4–125°C (solid, gas saturation-GC, Rordorf 1989) Cl Cl N © 2006 by Taylor & Francis Group, LLC Herbicides 3535 log (PL/Pa) = 11.754 – 3434.1/(T/K); measured range 32.4–125°C (liquid, gas saturation-GC, Rordorf 1989) 0.133 (20–25°C, selected, Wauchope et al. 1992; Hornsby et al. 1996) 0.0733 (Montgomery 1993) 0.088 (20°C, gas saturation, Tomlin 1994) Henry’s Law Constant (Pa·m3/mol at 25°C or as indicated): 0.700 (20°C, volatilization rate, Burkhard & Guth 1981) 0.669 (20°C, calculated-P/C, Suntio et al. 1988) 0.637 (20°C, calculated-P/C, Muir 1991) 0.669 (20–25°C, calculated-P/C, Montgomery 1993) Octanol/Water Partition Coefficient, log KOW: 2.90 (Rao & Davidson 1980; selected, Suntio et al. 1988, Magee 1991) 2.57; 2.65 (RP-HPLC-RT correlation; shake flask, Eadsforth & Moser 1983) 3.06 (shake flask, Geyer et al. 1984) 2.94 (Hansch & Leo 1985) 1.63 (Reinert 1989) 2.98 (selected, Dao et al. 1983, Gerstl & Helling 1987) 2.90 (shake flask, Log P Database, Hansch & Leo 1987) 2.90 (recommended, Sangster 1993) 2.70 (Tomlin 1994) 2.74 (recommended, Hansch et al. 1995) 2.95 (RP-HPLC-RT correlation, Nakamura et al. 2001) 2.98 (RP-HPLC-RT correlation using short ODP column, Donovan & Pescatore 2002) Bioconcentration Factor, log BCF: 1.74 (fish in static water, Kenaga 1975; Kenaga & Goring 1980) 2.08 (calculated-S, Kenaga 1980; quoted, Isensee 1991) 1.08 (calculated-KOC, Kenaga 1980) 1.18–1.60 (fish, Freitag et al. 1982) 1.30 (algae, Freitag et al. 1982) 1.72 (estimated-S, Lyman et al. 1982; quoted, Howard 1991) 2.03–2.32 (Montgomery 1993) Sorption Partition Coefficient, log KOC at 25°C or as indicated: 2.91 (potting soil with 22% organic content, Massini 1961) 2.08 (sandy loam with 5% organic content, Massini 1961) 2.37 (soil, Hamaker & Thompson 1972–1987) 2.95 (soil, calculated-S as per Kenaga & Goring 1980, Kenaga 1980) 2.35 (Rao & Davidson 1980) 2.94 (soil, estimated-S, Lyman et al. 1982; quoted, Howard 1991) 2.37, 1.45 (quoted, calculated-MCI ., Gerstl & Helling 1987) 2.96 (Reinert 1989) 2.37; 2.31 (reported as log KOM; estimated as log KOM, Magee 1991) 2.21, 2.57–2.96 (soil, quoted values, Bottoni & Funari 1992) 2.60 (soil, 20–25°C, estimated, Wauchope et al. 1992; Hornsby et al. 1996) 2.60 (estimated-chemical structure, Lohninger 1994) 2.31 (soil, calculated-MCI 1., Sabljic et al. 1995) Environmental Fate Rate Constants, k, or Half-Lives, t.: Volatilization: t. ~ 7.4 d, based on Henry’s law constant for a model river 1-m deep with a wind velocity of 3 m/s and flowing at 1 m/s (estimated, Lyman et al. 1982; quoted, Howard 1991); t. ~ 11 d from 1 m depth of water at 20°C (estimated, Muir 1991). Photolysis: photolytic t. = 15 d in water (Tomlin 1994). © 2006 by Taylor & Francis Group, LLC 3536 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals Oxidation: photooxidation t. = 92 d in air, based on estimation for the vapor-phase reaction with hydroxyl radicals in atmosphere (Atkinson 1987; quoted, Howard 1991). Hydrolysis: Biodegradation: t. ~ 7 d for 5 µg/mL to biodegrade in sediment suspension at 30°C (Miyazaki et al. 1975; quoted, Muir 1991). Biotransformation: Bioconcentration, Uptake (k1) and Elimination (k2) Rate Constants: Half-Lives in the Environment: Air: t. = 92 d, based on estimation for the vapor-phase reaction with hydroxyl radicals in atmosphere (Atkinson 1987; quoted, Howard 1991). Surface water: Ground water: reported t. = 44–360 d (Bottoni & Funari 1992) Sediment: t. ~ 7 d for 5 µg/mL to biodegrade in sediment suspension at 30°C (Miyazaki et al. 1975; quoted, Muir 1991). Soil: estimated persistence of 4 months (Kearney et al. 1969; quoted, Jury et al. 1987); t. = 1–6 months in soil depending on soil type (Beynon & Wright 1972; Verloop 1972; quoted, Tomlin 1994); persistence of 4 months in soil (Edwards 1973; quoted, Morrill et al. 1982); persistence of 4 months (Wauchope 1978); t. = 1.5 to 12 months depending upon soil type (Herbicide Handbook 1989); selected t. = 60 d (Wauchope et al. 1992; Hornsby et al. 1996); reported t. = 45–360 d (Bottoni & Funari 1992). Biota: © 2006 by Taylor & Francis Group, LLC Herbicides 3537 17.1.1.27 Dichlorprop Common Name: Dichlorprop Synonym: Cornox RK, dichloroprop, Dikofag DP, 2,4-DP, Hedonal DP, Polymone Chemical Name: ( ± )-2-(2,4-dichlorophenoxy) propanoic acid; ( ± )-2-(2,4-dichlorophenoxy) propionic acid Uses: herbicide and growth regulator to control annual broadleaf and grass weeds; also to control aquatic weeds and chemical maintenance of embankments and roadside verges. CAS Registry No: 120-36-5 Molecular Formula: C9H8Cl2O3 Molecular Weight: 235.064 Melting Point (°C): 117.5 (Lide 2003) Boiling Point (°C): Density (g/cm3 at 20°C): 1.64 (25°C, Bailey & White 1965) 1.42 (Herbicide Handbook 1989; Tomlin 1994) Molar Volume (cm3/mol): 232.0 (calculated-Le Bas method at normal boiling point) 165.6 (calculated-density) Dissociation Constant pKa: 2.855 (Cessna & Grover 1978) 2.86 (Wauchope et al. 1992; Hornsby et al. 1996) 3.00 (Tomlin 1994) Enthalpy of Vaporization, .HV (kJ/mol): 127.9 (Rordorf 1989) Enthalpy of Fusion, .Hfus (kJ/mol): 34.31 (DSC method, Plato 1972) 30.9 (Rordorf 1989) Entropy of Fusion, .Sfus (J/mol K): Fugacity Ratio at 25°C (assuming .Sfus = 56 J/mol K), F: 0.124 (mp at 117.5°C) Water Solubility (g/m3 or mg/L at 25°C or as indicated): 350 (20°C, Woodford & Evans 1963; Spencer 1973) 350 (Martin & Worthing 1977) 350 (20°C, Hartley & Kidd 1987; Worthing & Walker 1987, 1991) 710 (28°C, Herbicide Handbook 1989) 50 (ester, 20–25°C, estimated, Wauchope et al. 1992; Lohninger 1994; Hornsby et al. 1996) Vapor Pressure (Pa at 25°C or as indicated and reported temperature dependence equations): 4.50 . 10–4 (20°C, Hartley & Kidd 1987) 2.90 . 10–7, 4.10 . 10–5, 2.8 . 10–3, 0.11, 2.80 (25, 50, 70, 100, 125°C, gas saturation-GC, Rordorf 1989) log (PS/Pa) = 21.26 – 8289.2/(T/K); measured range 95.7–118°C (solid, gas saturation-GC, Rordorf 1989) log (PL/Pa) = 17.174 – 6682.8/(T/K); measured range 120–150°C (liquid, gas saturation-GC, Rordorf 1989) 4.00 . 10–4 (20–25°C, estimated, Wauchope et al. 1992; Hornsby et al. 1996) < 1.0 . 10–5 (20°C, Tomlin 1994) Henry’s Law Constant (Pa·m3/mol at 25°C): 2.69 . 10–4 (calculated-P/C, this work) Cl Cl O OH O © 2006 by Taylor & Francis Group, LLC 3538 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals Octanol/Water Partition Coefficient, log KOW: 2.75 (RP-HPLC-k. correlation, Braumann et al. 1983) 3.43 (shake flask-GC, Ilchmann et al. 1993) 2.06 to –0.22 (pH 4–7, shake flask-LSC, Riise & Salbu 1992) 1.77 (Tomlin 1994) 3.43 (recommended, Sangster 1993; Hansch et al. 1995) Bioconcentration Factor, log BCF: 1.36 (calculated-S, Kenaga 1980) Sorption Partition Coefficient, log KOC: 2.23 (soil, calculated-S, Kenaga 1980) 3.00 (soil, 20–25°C, estimated, Wauchope et al. 1992; Lohninger 1994; Hornsby et al. 1996) 2.05, 2.07, 1.70, 1.79, 1.73 (5 soils: soil A 30.4% OC and pH 4.4, soil B14.6% OC pH 4.1, soil C/loam 3.3% OC pH 5.0, soil D/silty clay 1.3% OC pH 5.1, soil E/sand 1.4% OC pH 5.3, batch equilibrium-sorption isotherms, Riise Salbu 1992) 1.08–1.60 (Tomlin 1994) Environmental Fate Rate Constants, k, or Half-Lives, t.: Photolysis: photodegradation t. = 10 to 19 d on 3 Spanish natural dry soils; t. = 22 to 59 d on 10% peat-amened dry soils; degradation t. ~ 2–6 d on moist soils at field capacity and saturation soils for degradation at 0,1 and 2 exposures days; and t. = 16–37 d on moist soils at field capacity and saturated soils for degradation at 2,4 and 10 exposure days (Romero et al. 1998) Half-Lives in the Environment: Soil: t. = 12 d and 8 d in Quachita Highlands = forest and grassland soil, respectively, t. = 10 d in gross timbers forest soil, average t. = 10 d in 3 soils (Altom & Stritzke 1973); selected field t. = 10 d (Wauchope et al. 1992; Hornsby et al. 1996); t. ~ 8 d in soil (Tomlin 1994) photodegradation t. = 10–19 d in 3 Spanish natural dry soils, t. = 22–59 d in the 10% peat-amended dry soils; degradation t. ~ 2–6 d on moist soils at field capacity and saturation soils for degradation at 0,1 and 2 exposures days; and t. = 16–37 d on moist soils at field capacity and saturated soils for degradation at 2,4 and 10 exposure days (Romero et al. 1998) © 2006 by Taylor & Francis Group, LLC Herbicides 3539 17.1.1.28 Diclofop-methyl Common Name: Diclofop-methyl Synonym: Hoelon, dichlordiphenoprop, Hoegrass, Illoxan Chemical Name: methyl 2-[4-(2.,4.-dichlorophenoxy)-phenoxy]propanoate Uses: herbicide to control post-emergent wild oats, wild millets, and other annual grass weeds in wheat, barley, rye, red fescue, and broadleaf weeds in crops such as soybeans, sugar cane, fodder beet, flax, legumes, oilseed rape, sunflowers, clover, lucerne, groundnuts, brassicas, carrots, celery, beet root, parsnips, lettuce, spinach, potatoes, tomatoes, fennel, alliums, herbs, etc. CAS Registry No: 51338-27-3 Molecular Formula: C16H14Cl2O4 Molecular Weight: 341.186 Melting Point (°C): 40 (Lide 2003) Boiling Point (°C): 175–176 (at 0.1 mmHg, Hartley & Kidd 1987; Herbicide Handbook 1989) Density (g/cm3): 1.30 (40°C, Hartley & Kidd 1987; Worthing & Walker 1987; Herbicide Handbook 1989) 1.035 (Herbicide Handbook 1989) Acid Dissociation Constants, pKa: 3.1 (Wauchope et al. 1992; Hornsby et al. 1996) Molar Volume (cm3/mol): 349.6 (calculated-Le Bas method at normal boiling point) 329.7 (calculated-density) Dissociation Constant pKa: 3.1 (Wauchope et al. 1992; Hornsby et al. 1996) Enthalpy of Fusion, .Hfus (kJ/mol): Entropy of Fusion, .Sfus (J/mol K): Fugacity Ratio at 25°C (assuming .Sfus = 56 J/mol K), F: 0.713 (mp at 40°C) Water Solubility (g/m3 or mg/L at 25°C or as indicated): 3.0 (22°C, Hartley & Kidd 1987; Worthing & Walker 1987; Worthing & Hance 1991) 3.0 (22°C, Herbicide Handbook 1989) 0.80 (20–25°C, selected, Wauchope et al. 1992; Hornsby et al. 1996) 0.80 (20°C, pH 7, Tomlin 1994) 4.23 (Majewski & Capel 1995) 4.06 (calculated-group contribution method, Kuhne et al. 1995) 3.0 (Lohninger 1994; Milne 1995) 0.8 (selected, Halfon et al. 1996) Vapor Pressure (Pa at 25°C or as indicated): 3.44 . 10–5 (20°C, Worthing 1983, 1987; Hartley & Kidd 1987) 3.40 . 10–5 (20°C, Worthing & Walker 1987, Worthing & Hance 1991) 3.47 . 10–5, 1.6 . 10–4, 3.87 . 10–3 (20°C, 30°C, 54.3°C, Herbicide Handbook 1989) 5.91 . 10–5 (selected, Wauchope et al. 1992; Hornsby et al. 1996) 2.5 . 10–4, 7.7 . 10–3 (20°C, 50°C, Tomlin 1994) 4.80 . 10–5 (quoted, Majewski & Capel 1987) 4.7 . 10–4 (selected, Halfon et al. 1996) Cl Cl O O O O © 2006 by Taylor & Francis Group, LLC 3540 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals Henry’s Law Constant (Pa·m3/mol at 25°C): 0.00387 (calculated-P/C, Majewski & Capel 1995) 0.199 (calculated-P/C, this work) Octanol/Water Partition Coefficient, log KOW: 4.80 (shake flask, Log P Database, Hansch & Leo 1987) 4.601 (Stevens et al. 1988) 4.58 (Worthing & Hance 1991) 4.60 (shake flask, pH 7, Baker et al. 1992) 4.80 (recommended, Sangster 1993) 4.5775 (Tomlin 1994) 4.80 (recommended, Hansch et al. 1995) 5.52 (Pomona-database, Muller & Kordel 1996) 4.87 (RP-HPLC-RT correlation using short ODP column, Donovan & Pescatore 2002) Bioconcentration Factor, log BCF or log KB: 2.74 (calculated-S as per Kenaga 1980, this work) Sorption Partition Coefficient, log KOC: 4.69, 4.20 (Wauchope et al. 1992) 4.15–4.39 (soil, quoted values, Bottoni & Funari 1992) 4.20 (20–25°C, soil, recommended, Wauchope et al. 1992; Hornsby et al. 1996) 4.25 (soil, HPLC-screening method, mean value of different stationary and mobile phases, Kordel et al. 1993, 1995b) 4.15–4.39 (soil, Tomlin 1994) 4.20 (estimated-chemical structure, Lohninger 1994) 4.25; 3.61 (HPLC-screening method; calculated-PCKOC fragment method, Muller & Kordel 1996) 5.505, 5.334, 4.122, 4.737, 4.182 (first generation Eurosoils ES-1, ES-2, ES-3, ES-4, ES-5, shake flask/batch equilibrium-HPLC/UV, Gawlik et al. 1998) 4.002, 3.731, 3.453, 3.257, 3.715 (second generation Eurosoils ES-1, ES-2, ES-3, ES-4, ES-5, shake flask-batch equilibrium-HPLC/UV and HPLC-k. correlation, Gawlik et al. 2000) Environmental Fate Rate Constants, k, or Half-Lives, t.: Volatilization: Photolysis: Oxidation: Hydrolysis: Biodegradation: first-order rate constants k = –0.0883, –0.225, –0.266 h–1 in nonsterile sediment and k = –0.0158, –0.0139, –0.0134 h–1 in sterile sediment by shake-tests at Davis Bayou, k = –0.0457, –0.103, –0.120 h–1 in nonsterile water and k = –0.00233, –0.00722, –0.00785 h–1 in sterile water by shake-tests at Davis Bayou (Walker et al. 1988) t. = 10 d in sandy soils and t. ~ 30 d in sandy clay soils under aerobic conditions (Herbicide Handbook 1989) Biotransformation: Bioconcentration, Uptake (k1) and Elimination (k2) Rate Constants: Half-Lives in the Environment: Air: Surface water: t. = 363 d at 25°C and pH 5, t. = 31.7 d at pH 7 and t. = 0.52 d at pH 9 (Tomlin 1994). Ground water: reported t. = 6–9, 23–38 and 150 d (Bottoni & Funari 1992) Sediment: Soil: t. = 10 d in sandy soils and t. ~ 30 d in sandy clay soils while under anaerobic conditions, results were similar except that the very rapid cleavage of the ester bond by hydrolysis within one hour to propionic acid derivatives was experienced and within 2 d, up to 86% of the parent compound was metabolized into various free acid metabolites and up to 3.7% of phenol metabolites (Herbicide Handbook 1989); © 2006 by Taylor & Francis Group, LLC Herbicides 3541 t. = 6–9 d, 23–38 d and 150 d (Bottoni & Funari 1992); selected field t. = 30 d at pH 7.0 (Wauchope et al. 1992; Hornsby et al. 1996) V = 1–57 d and t. = 30–281 d for various soils in field trials (Tomlin 1994). t. = 30 d (selected, Halfon et al. 1996). Biota: t. = 3–7 d for wheat (Herbicide Handbook 1989) t. = 3 d in sugar beet (Tomlin 1994). © 2006 by Taylor & Francis Group, LLC 3542 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals 17.1.1.29 Dinitramine Common Name: Dinitramine Synonym: Cobex, Cobexo Chemical Name: N,N-diethyl-2,6-dinitro-4-trifluoromethyl-m-phenylenediamine Uses: herbicide for selective pre-plant soil incorporating control of many annual grass and broadleaf weeds in cotton, soybeans, peas, groundnuts, beans, sunflowers, safflowers, carrots, turnips, fennel, chicory, etc. and in transplanted tomatoes, capsicums, aubergines, and brassicas. CAS Registry No: 29091-05-2 Molecular Formula: C11H13N4O4F3 Molecular Weight: 322.241 Melting Point (°C): 98 (Lide 2003) Boiling Point (°C): Density (g/cm3 at 20°C): 1.50 (25°C, Ashton & Crafts 1981; Hartley & Kidd 1987) Molar Volume (cm3/mol): 265.7 (calculated-Le Bas method at normal boiling point) Dissociation Constant pKa: 4.5 (Haag & Yao 1992) Enthalpy of Fusion, .Hfus (kJ/mol): Entropy of Fusion, .Sfus (J/mol K): Fugacity Ratio at 25°C (assuming .Sfus = 56 J/mol K), F: 0.192 (mp at 98°C) Water Solubility (g/m3 or mg/L at 25°C or as indicated): 1.1 (Martin & Worthing 1977; Kenaga 1980; Kenaga & Goring 1980; Khan 1980; Isensee 1991) 1.0 (Wauchope 1978; Verschueren 1983) 1.0 (20°C, Ashton & Crafts 1981; Hartley & Kidd 1987) 1.1 (Worthing & Walker 1987, 1991) 1.1 (20–25°C, selected, Augustijn-Beckers et al. 1994; Hornsby et al. 1996) 1.0 (20°C, Tomlin 1994; Milne 1995) Vapor Pressure (Pa at 25°C or as indicated): 0.00048 (Khan 1980; Ashton & Crafts 1981) 0.00048 (Verschueren 1983) 0.000479 (Hartley & Kidd 1987; Worthing & Hance 1991; Tomlin 1994) 0.00040 (20°C, selected, Suntio et al. 1988) 0.00048 (20–25°C, selected, Augustijn-Beckers et al. 1994; Hornsby et al. 1996) Henry’s Law Constant (Pa·m3/mol at 25°C or as indicated): 0.160 (20°C, calculated-P/C, Suntio et al. 1988) Octanol/Water Partition Coefficient, log KOW: 4.31 (selected, Dao et al. 1983) 4.30 (Worthing & Hance 1991; Tomlin 1994) 4.30 (Milne 1995) 4.30 (recommended, Hansch et al. 1995) 3.89 (LOGPSTAR or CLOGP data, Sabljic et al. 1995) NH2 NO2 O2N N F F F © 2006 by Taylor & Francis Group, LLC Herbicides 3543 Bioconcentration Factor, log BCF: 2.77 (calculated-S, Kenaga 1980; quoted, Isensee 1991) 2.45 (calculated-KOC, Kenaga 1980) Sorption Partition Coefficient, log KOC: 3.60 (soil, Harvey 1974) 3.61 (soil, calculated-S as per Kenaga & Goring 1980, Kenaga 1980) 3.60 (20–25°C, estimated, Augustijn-Beckers et al. 1994; Hornsby et al. 1996) 3.84 (estimated-chemical structure, Lohninger 1994) 3.63 (soil, calculated-MCI 1., Sabljic et al. 1995) 3.63; 3.42 (soil, quoted exptl.; estimated-general model using molecular descriptors, Gramatica et al. 2000) Environmental Fate Rate Constants, k, or Half-Lives, t.: Volatilization: Photolysis: t. < 1 h in distilled water, river water and ocean water under sunlight (Newsom & Woods 1973; quoted, Cessna & Muir 1991). Oxidation: Hydrolysis: Biodegradation: t. = 22 d for 0.5 µg/mL to biodegrade in flooded soil with approximately 1 cm of water on top of the soil (Savage 1978; quoted, Muir 1991). Biotransformation: Bioconcentration, Uptake (k1) and Elimination (k2) Rate Constants: Half-Lives in the Environment: Soil: t. = 22 d for 0.5 µg/mL to biodegrade in flooded soil with approximately 1 cm of water on top of the soil (Savage 1978; quoted, Muir 1991); persistence of 3 months in soil (Wauchope 1978); selected field t. = 30 d (Augustijn-Beckers et al. 1994; Hornsby et al. 1996); t. = 10–66 d (Tomlin 1994). © 2006 by Taylor & Francis Group, LLC 3544 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals 17.1.1.30 Dinoseb Common Name: Dinoseb Synonym: Anatox, Aretit, Basanite, Butaphene, Caldon, Chemox, Dibutox, Dinitrall, DNBP, DN-289, DNOSAP, DNOSBP, DNSBP, Dow General, Dyanap, Dytop Chemical Name: 2-sec-butyl-4,6-dinitrophenol Uses: herbicides/insecticides; pre- or post-emergence control of broadleaf weeds in cereals, maize, lucerne, clover, trefoil, grass leys, potatoes, peas, onions, garlics, peas, leeks, soya beans, orchards, groundnuts, strawberries, vineyards and other crops; for control of strawberry runners and raspberry suckers and overwintering forms of insect pests on fruit trees; also used as a desiccant for leguminous seed crops; destruction of potato haulms; as a pre-harvest hop defoliant, etc. CAS Registry No: 88-85-7 Molecular Formula: C10H12N2O5 Molecular Weight: 240.212 Melting Point (°C): 40 (Lide 2003) Boiling Point (°C): 362 (estimated, Grain 1982) Density (g/cm3 at 20°C): 1.265 (45°C, Hartley & Kidd 1987; Herbicide Handbook 1989; Milne 1995) Molar Volume (cm3/mol): 218.0 (calculated-Le Bas method at normal boiling point) Dissociation Constant pKa: 4.62 (radiometer/pH meter, Cessna & Grover 1978; Hornsby et al. 1996) 4.61 (radiometer/pH meter, Cessna & Grover 1978) 4.62 (Worthing & Walker 1987, 1991) 4.50 (Yao & Haag 1991) Enthalpy of Fusion, .Hfus (kJ/mol): Entropy of Fusion, .Sfus (J/mol K): Fugacity Ratio at 25°C (assuming .Sfus = 56 J/mol K), F: 0.713 (mp at 40°C) Water Solubility (g/m3 or mg/L at 25°C or as indicated): 50 (Gunther 1968; Spencer 1982; Thomas 1982) 52 (Kearney & Kaufman 1975; Khan 1980) 50 (Martin & Worthing 1977; Kenaga 1980) 52 (Ashton & Crafts 1981; Herbicide Handbook 1989) 100 (rm. temp., Worthing & Walker 1983, Worthing & Hance 1991) 52 (20°C, Hartley & Kidd 1987; Milne 1995) 52 (20–25°C, selected, Hornsby et al. 1996) Vapor Pressure (Pa at 25°C or as indicated): 130 (151.5°C, Khan 1980) 133 (151.1°C, Ashton & Crafts 1981) 0.0008, 0.0067 (supercooled liquid, estimated, Grain 1982) 0.0067 (Thomas 1982) 0.0023 (30°C, Spencer 1982) 10 (20°C, selected, Suntio et al. 1988) 0.183 (60°C, Worthing & Hance 1991) 0.0067 (20–25°C, selected, Hornsby et al. 1996) OH NO2 O2N © 2006 by Taylor & Francis Group, LLC Herbicides 3545 Henry’s Law Constant (Pa·m3/mol at 25°C or as indicated): 51.1 (20°C, calculated-P/C, Suntio et al. 1988) Octanol/Water Partition Coefficient, log KOW: 3.59 (Hansch & Leo 1979) 3.69 (calculated, Zitko et al. 1976) 3.69 (Hansch & Leo 1985) 4.10 (RP-PHLC-RT correlation, Klein et al. 1988) 3.14 (shake flask/slow stirring-GC, De Bruijn et al. 1989) 3.0, 3.57 (pH 7, pH 2, shake flask, Brooke et al. 1990) 3.69 (recommended, Sangster 1993) 3.56 (recommended, Hansch et al. 1995) Bioconcentration Factor, log BCF: 1.83 (calculated-S, Kenaga 1980a; quoted, Howard 1991) 0.778 (calculated-KOC, Kenaga 1980) 1.51 (measured, Kenaga 1980; quoted, Isensee 1991) Sorption Partition Coefficient, log KOC: 2.85 (soil, Thomas 1982) 2.09 (soil, Kenaga 1980a; Kenaga & Goring 1980) 2.71 (soil, calculated-S as per Kenaga & Goring 1980, Kenaga 1980a) 3.82 (HPLC-k. correlation, cyanopropyl column, mobile phase buffered to pH 3, Hodson & Williams 1988) 2.68 (estimated as log KOM, Magee 1991) 1.80, 2.04, 2.08 (soil, literature values, Bottoni & Funari 1992) 2.70 (selected, Lohninger 1994) 2.09 (soil, calculated-MCI 1., Sabljic et al. 1995) 1.48 (soil, 20–25°C, estimated, Hornsby et al. 1996) Adsorption coefficient, Kd (L·kg–1): 6.4, 64 (homoionic K+-kaolinite, K+-montmorillonite clay minerals, Haderlein et al. 1996) Environmental Fate Rate Constants, k, or Half-Lives, t.: Volatilization: initial rate constant k = 1.1 . 10–3 h–1 and predicted rate constant k = 2.6 . 10–3 h–1 from soil with t. = 266.5 h (Thomas 1982). Photolysis: Oxidation: photooxidation t. = 12.2–122 h in air, based on estimated rate constant for the reaction with hydroxyl radical in air (Atkinson 1987; quoted, Howard et al. 1991) k(aq.) = (0.003–2) . 105 M–1 s–1 for direct reaction with ozone in water at pH 1.9–5.0 and 24 ± 1°C, with t. = 0.16 s at pH 7 (Yao & Haag 1991). k(calc) = 4 . 109 M–1 s–1 for the reaction with hydroxyl radical in aqueous solutions at 24 ± 1°C (Haag & Yao 1992). Hydrolysis: Biodegradation: aqueous aerobic t. = 1032–2952 h, based on aerobic soil mineralization data for one soil (Doyle et al. 1978; quoted, Howard et al. 1991) and aqueous anaerobic t. = 96–360 h, based on anaerobic soil dieaway test data for isopropalin (Gingerich & Zimdahl 1976; quoted, Howard et al. 1991). Biotransformation: Bioconcentration, Uptake (k1) and Elimination Constants (k2): Half-Lives in the Environment: Air: t. = 12.2–122 h, based on estimated rate constant for the reaction with hydroxyl radical in air (Atkinson 1987; quoted, Howard et al. 1991). Surface water: t. = 1032–2952 h, based on aerobic soil mineralization data for one soil (Doyle et al. 1978; quoted, Howard et al. 1991); © 2006 by Taylor & Francis Group, LLC 3546 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals measured rate constant k = (0.003–2) . 105 M–1 s–1 for direct reaction with ozone in water at pH 1.9 -5.0 and 24 ± 1°C, with t. = 0.16 s at pH 7 (Yao & Haag 1991). Ground water: t. = 96–5904 h, based on estimated unacclimated aqueous aerobic and anaerobic biodegradation half-lives (Howard et al. 1991) reported t. = 30 d (Bottoni & Funari 1992) Sediment: Soil: t. = 1032–2952 h, based on aerobic soil mineralization data for one soil (Doyle et al. 1978; quoted, Howard et al. 1991); reported t. = 30 d (Bottoni & Funari 1992); field t. = 30 d at 20–25°C (estimated, Hornsby et al. 1996). Biota: © 2006 by Taylor & Francis Group, LLC Herbicides 3547 17.1.1.31 Diphenamid Common Name: Diphenamid Synonym: Difenamide, Dimid, Dymid, Enide, Fenam, Rideon Chemical Name: N,N-dimethyldiphenylacetamide; N,N-dimethyl-.-phenyl-benzeneacetamide Uses: herbicide for pre-emergence control of annual grasses and some broadleaf weeds in cotton, sweet potatoes, tomatoes, vegetables, capsicums, okra, soybeans, groundnuts, tobacco, pome fruit, stone fruit, citrus fruit, bush fruit, strawberries, forestry nurseries, and ornamental plants, shrubs, and trees. CAS Registry No: 957-51-7 Molecular Formula: C16H17NO Molecular Weight: 239.312 Melting Point (°C): 135 (Lide 2003) Boiling Point (°C): Density (g/cm3 at 20°C): 1.17 (23.3°C, Hartley & Kidd 1987; Tomlin 1994; Milne 1995) Molar Volume (cm3/mol): 284.2 (calculated-Le Bas method at normal boiling point) Dissociation Constant pKa: Enthalpy of Fusion, .Hfus (kJ/mol): 27.405 (DSC method, Plato & Glasgow 1969) Entropy of Fusion, .Sfus (J/mol K): Fugacity Ratio at 25°C (assuming .Sfus = 56 J/mol K), F: 0.0833 (mp at 135°C) Water Solubility (g/m3 or mg/L at 25°C or as indicated): 240 (Melnikov 1971) 260 (27°C Spencer 1973, 1982; Khan 1980; Worthing & Walker 1987) 260 (Martin & Worthing 1977; Weber et al. 1980; Kenaga 1980) 260 (27°C, Hartley & Kidd 1987; Herbicide Handbook 1989; Tomlin 1994) 280 (20–25°C, selected, Hornsby et al. 1996) Vapor Pressure (Pa at 25°C or as indicated): < 1.33 . 10–4 (Weber et al. 1980) negligible (20°C, Hartley & Kidd 1987; Tomlin 1994) 4.0 . 10–6 (20–25°C, selected, Hornsby et al. 1996) Henry’s Law Constant (Pa·m3/mol at 25°C or as indicated): Octanol/Water Partition Coefficient, log KOW: Bioconcentration Factor, log BCF: 1.43 (calculated-S, Kenaga 1980) Sorption Partition Coefficient, log KOC: 2.32 (soil, calculated-S, Kenaga 1980) 2.32 (selected, Lohninger 1994) 2.32 (soil, 20–25°C, selected, Hornsby et al. 1996) O N © 2006 by Taylor & Francis Group, LLC 3548 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals Environmental Fate Rate Constants, k, or Half-Lives, t.: Photolysis: t. = 2.25 h in distilled water (Tanaka et al. 1981; quoted, Cessna & Muir 1991); Half-Lives in the Environment: Soil: estimated persistence of 8 months (Kearney et al. 1969; Edwards 1973; quoted, Morrill et al. 1982; Jury et al. 1987); persistence under warm damp conditions is ca. 3–6 months (Herbicide Handbook 1989; Tomlin 1994) field t. = 30 d at 20–25°C (selected, Hornsby et al. 1996). Biota: © 2006 by Taylor & Francis Group, LLC Herbicides 3549 17.1.1.32 Diquat Common Name: Diquat Synonym: Aquacide, Deiquat, Dextrone, Ortho, Pathclear, Preeglone, Reglone, Weedol, Weedtrine-D Chemical Name: 1,1.-ethylene-2,2.-dipyridine Uses: nonselective contact herbicide to control broadleaf weeds in fruit and vegetable crops. CAS Registry No: 2764-72-9 Molecular Formula: C12H14N2 Molecular Weight: 186.236 Melting Point (°C): 335–340 (Spencer 1982) Boiling Point (°C): Density (g/cm3 at 20°C): 1.22–1.27 (Ashton & Crafts 1981; Herbicide Handbook 1989; Montgomery 1993; Tomlin 1994) Molar Volume (cm3/mol): 230.6 (calculated-Le Bas method at normal boiling point) 149.6 (calculated-density) Dissociation Constant pKa: Enthalpy of Fusion, .Hfus (kJ/mol): Entropy of Fusion, .Sfus (J/mol K): Fugacity Ratio at 25°C (assuming .Sfus = 56 J/mol K), F: Water Solubility (g/m3 or mg/L at 25°C): 700000 (Khan 1980; Spencer 1982) 670000 (Weber et al. 1980) 700000 (Verschueren 1983) 700000 (Worthing & Hance 1991; Tomlin 1994) 700000 (Montgomery 1993) Vapor Pressure (Pa at 25°C or as indicated): < 0.00533 (Agrochemicals Handbook 1983) < 1.3 . 10–5 (Worthing & Hance 1991; Tomlin 1994) < 1.3 . 10–5 (20°C, Montgomery 1993) Henry’s Law Constant (Pa·m3/mol at 25°C or as indicated): < 6.38 . 10–9 (20–25°C, calculated-P/C, Montgomery 1993) < 3.42 . 10–9 (calculated-P/C, this work) Octanol/Water Partition Coefficient, log KOW: –3.05 (Garten & Trabalka 1983) 2.78 (Reinert 1989) –4.60 (20°C, Worthing & Hance 1991; Tomlin 1994) –4.60 (Montgomery 1993) Bioconcentration Factor, log BCF: –2.84 (calculated-S as per Kenaga 1980, this work) –5.92 (calculated-log KOW as per Mackay 1982, this work) Sorption Partition Coefficient, log KOC: 2.84 (Reinert 1989) 0.420 (calculated, Montgomery 1993) 0.425 (calculated-S as per Kenaga 1980, this work) N N © 2006 by Taylor & Francis Group, LLC 3550 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals Environmental Fate Rate Constants, k, or Half-Lives, t.: Volatilization: Photolysis: t. = 192 h for 10 µg/mL to degrade in distilled water under 240–260 nm light (Funderburk et al. 1960; quoted, Cessna & Muir 1991); t. < 5 wk for 4 µg/mL to degrade in distilled water under sunlight (Slade & Smith 1967; quoted, Cessna & Muir 1991); dry diquat photodecomposed by UV light with t. = 48 h (Funderburk & Bozarth 1967; quoted, Montgomery 1993); t. ~ 48 h when associated with aerosols (Howard 1991); t. = 3 wk for 3% of 5 µg/mL to degrade in distilled water under sunlight (Smith & Grove 1969; quoted, Cessna & Muir 1991). Oxidation: k(aq.) = 5.9 . 109 M–1 s–1 for the reaction (Fenton with reference to acetophenone) with hydroxyl radical in aqueous solutions at pH 3.1 and at 24 ± 1°C (Buxton et al. 1988; quoted, Faust & Hoigne 1990; Haag & Yao 1992) k(aq.) = (0.6 ± 0.2) M–1 s–1 for direct reaction with ozone in water at pH 3.1 and 22°C, with a half-life of 15 h at pH 7 (Yao & Haag 1991). k(aq.) = (8.0 ± 1.8) . 108 M–1 s–1 for the reaction (Fenton with reference to acetophenone) with hydroxyl radical in aqueous solutions at pH 3.1 and at 24 ± 1°C (Haag & Yao 1992). Hydrolysis: t. = 74 d under simulated sunlight at pH 7 (Montgomery 1993; Tomlin 1994). Biodegradation: t. ~ 50 d to biodegrade in lake water (Hiltibran 1972; quoted, Muir 1991); t. > 158 d for 1.5 µg/mL of infested sediment-water microcosm to biodegrade in sediment and t. ~ 2 d in water both at 25°C (derived from Simsiman & Chesters 1976; Muir 1991). Biotransformation: Bioconcentration, Uptake (k1) and Elimination (k2) Rate Constants: Half-Lives in the Environment: Air: Surface water: t. ~ 50 d to biodegrade in lake water (Hiltibran 1972; quoted, Muir 1991); t. ~ 2 d of 14C-diquat in water of a weed-infested simulated lake impoundment containing Lake Mendota sediment, the rapid disappearance is attributed to adsorption by sediments, suspended particulate matter and aquatic plants (shake flask-scintillation spectrometry, Simsiman & Chesters 1976) measured rate constant k = (0.6 ± 0.2) M–1 s–1 for direct reaction with ozone in water at pH 3.1 and 22°C, with t. = 15 h at pH 7 (Yao & Haag 1991). Ground water: Sediment: Slow microbial degradation due to tight bonding of adsorbed Diquat to the clay minerals on the sediment (shake flask-liquid scintillation spectrometry, Simsiman & Chesters 1976) t. > 158 d for 1.5 µg/mL of infested sediment-water microcosm to biodegrade (derived from results of Simsiman & Chesters 1976; Muir 1991). Soil: Biota: © 2006 by Taylor & Francis Group, LLC Herbicides 3551 17.1.1.33 Diuron Common Name: Diuron Synonym: AF 101, Cekiuron, Crisuron, Dailon, DCMU, Diater, dichlorofonidim, Di-on, Direx, DMU, Drexel, Duran, Dynex, Herbatox, Karmex, Marmer, NA 2767, Telvar, Unidron, Urox D, Vonduron Chemical Name: 3-(3,4-dichlorophenyl)-1,1-dimethylurea; N.-(3,4-dichlorophenyl)-N,N-dimethylurea Uses: pre-emergence herbicide in soils to control germinating broadleaf grasses and weeds in crops such as apples, cotton, grapes, pears, pineapple, and alfalfa; also used as sugar cane flowering depressant. CAS Registry No: 330-54-1 Molecular Formula: C9H10Cl2N2O Molecular Weight: 233.093 Melting Point (°C): 158 (Lide 2003) Boiling Point (°C): 180 (decomposes, Montgomery 1993) Density (g/cm3 at 20°C): Molar Volume (cm3/mol): 223.8 (calculated-Le Bas method at normal boiling point) 188.0 (modified Le Bas method at normal boiling point, Spurlock & Biggar 1994a) Dissociation Constant pKa: –1 to –2 (Montgomery 1993) Enthalpy of Vaporization, .HV (kJ/mol): 66.0 (Rordorf 1989) Enthalpy of Fusion, .Hfus (kJ/mol): 33.89 (DSC method, Plato & Glasgow 1969) 27.3 (Rordorf 1989) Entropy of Fusion, .Sfus (J/mol K): Fugacity Ratio at 25°C (assuming .Sfus = 56 J/mol K), F: 0.0496 (mp at 158°C) Water Solubility (g/m3 or mg/L at 25°C or as indicated): 42.0 (Gunther et al. 1968; Melnikov 1971; Spencer 1973. 1982; Khan 1980; Ashton & Crafts 1981) 42.0 (20°C, Weber 1972; Weber et al. 1980) 37.3 (shake flask-UV, Freed et al. 1976; Freed 1976) 42.0 (Martin & Worthing 1977; Hartley & Kidd 1987; Worthing & Walker 1987, Worthing & Hance 1991; Herbicide Handbook 1989; Tomlin 1994; Milne 1995) 42.4 (shake flask, Briggs 1981) 22.0 (shake flask-HPLC, Ellgehausen et al. 1981) 38.7 (generator column-HPLC/RI, Swann et al. 1983) 120 (RP-HPLC-RT correlation, Swann et al. 1983) 19.6, 40.1, 53.4 (4, 25, 40°C, shake flask-liquid scintillation spectrometer LSS, Madhun et al. 1986) 42.0 (20–25°C, selected, Wauchope et al. 1992; Hornsby et al. 1996) 40.0 (20°C, Montgomery 1993) Vapor Pressure (Pa at 25°C or as indicated and reported temperature dependence equations): 1.6 . 10–5 (estimated, Nex & Swezey 1954) 3.8 . 10–6 (20°C, Johnson & Julin 1974) 4.1 . 10–4 (50°C, Khan 1980; Ashton & Crafts 1981) < 1.3 . 10–4 (20–25°C, Weber et al. 1980) 2.5 . 10–4 (Thomas 1982) HN N O Cl Cl © 2006 by Taylor & Francis Group, LLC 3552 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals 2.1 . 10–5 (Jury et al. 1983; quoted, Taylor & Glotfelty 1988; Taylor & Spencer 1990) 3.6 . 10–4 (Jury et al. 1983; quoted, Howard 1991) 2.7 . 10–4 (selected, Nkedi-Kizza et al. 1985) 4.1 . 10–4 (50°C, Hartley & Kidd 1987; Worthing & Hance 1991; Herbicide Handbook 1989) 2.0 . 10–4 (20°C, selected, Suntio et al. 1988) 5.30 . 10–4, 1.0 . 10–2, 0.130, 1.20, 79 (25, 50, 70, 100, 125°C, gas saturation-GC, Rordorf 1989) log (PS/Pa) = 13.339 – 4953.8/(T/K); measured range 36.2–90.2°C (solid, gas saturation-GC, Rordorf 1989) log (PL/Pa) = 9.800335 – 3445.24/(T/K); measured range not specified (liquid, gas saturation-GC, Rordorf 1989) 9.2 . 10–6 (20–25°C, selected, Wauchope et al. 1992; Hornsby et al. 1996) 1.1 . 10–6 (Tomlin 1994) Henry’s Law Constant (Pa·m3/mol at 25°C or as indicated): 1.4 . 10–4 (calculated-P/C, Jury et al. 1984, 1987a,b; Jury & Ghodrati 1989) 1.2 . 10–4 (20°C, calculated-P/C, Suntio et al. 1988) 1.3 . 10–4 (calculated-P/C, Taylor & Glotfelty 1988) 0.274 (calculated-P/C, Howard 1991) 2.1 . 10–5 (20°C, calculated-P/C, Muir 1991) 1.5 . 10–4 (20–25°C, calculated-P/C, Montgomery 1993) Octanol/Water Partition Coefficient, log KOW: 2.60 (calculated-f const., Rekker 1977) 2.81 (Rao & Davidson 1980) 2.68 (shake flask-UV, Briggs 1981) 2.89 (shake flask-HPLC, Ellgehausen et al. 1981) 2.60 (Elgar 1983) 2.77 (Hansch & Leo 1985) 2.69, 2.65, 2.63 (4, 25, 40°C, shake flask-liquid scintillation spectrometer LSS, Madhun et al. 1986) 2.86 (shake flask, Mitsutake et al. 1986) 1.97–2.81 (Montgomery 1993) 2.78 (recommended, Sangster 1993) 2.45 (RP-HPLC-RT correlation, Sicbaldi & Finizio 1993) 2.80 (Aquasol Database 1994; quoted, Pinsuwan et al. 1995) 2.81 (shake flask, Spurlock & Biggar 1994a) 2.85 ± 1.70 (Tomlin 1994) 2.58, 2.73 (shake flask-UV, RP-HPLC-k. correlation, Liu & Qian 1995) 2.68 (recommended, Hansch et al. 1995) 2.45 (RP-HPLC-RT correlation, Finizio et al. 1997) Bioconcentration Factor, log BCF: 1.40 (measured, Isensee 1976) 1.88 (calculated-S, Kenaga 1980) 1.34 (calculated-KOC, Kenaga 1980) 2.16 (Pimephales promelas, Call et al. 1987) 2.41, 2.48 (cuticle/water: tomato, pepper, Chaumat et al. 1991) 2.41, 2.51 (cuticle/water: box tree, laurel, Chaumat et al. 1991) 2.55, 2.28 (cuticle/water: pear, ivy, Chaumat et al. 1991) 1.18, 1.64 (cuticle/water: cleavers, vanilla, Chaumat et al. 1991) 2.45, 2.48 (cuticle/water: tomato, pepper, Evelyne et al. 1992) Bioaccumulation Factor, log BF: –1.70 (adipose tissue in both male & female Albino rats, Hodge et al. 1967) Sorption Partition Coefficient, log KOC: 2.60 (soil, Hamaker & Thompson 1972; Farmer 1976; Hance 1976) © 2006 by Taylor & Francis Group, LLC Herbicides 3553 2.75 (soil, calculated-S as per Kenaga & Goring 1977, Kenaga 1980) 2.59 (average of 3 soils, HPLC-RT correlation, McCall et al. 1980) 2.15–2.52 (Peck et al. 1980) 2.21 (soil, converted from reported KOM multiplied 1.724, Briggs 1981) 3.06, 2.41 (estimated-S, solubility and mp, Karickhoff 1981) 1.58, 2.42 (estimated-KOW, Karickhoff 1981) 2.58 (average of 84 soils, Rao & Davidson 1982) 2.18 (soil, Thomas 1982) 2.83 (Webster soil, Nkedi-Kizza 1983) 2.49 (soil slurry method, Swann et al. 1983) 2.48 (RP-HPLC-RT correlation, Swann et al. 1983) 3.03, 2.94 (4°C, 25°C, Semiahmoo soil, batch equilibrium method-LSS, Madhun et al. 1986) 2.82, 2.68 (4°C, 25°C, Adkins soil, batch equilibrium method-LSS, Madhun et al. 1986) 2.86, 2.44, 2.48; 2.81, 2.74, 2.44 (estimated-KOW; solubility, Madhun et al. 1986) 2.50 (calculated-MCI ., Gerstl & Helling 1987) 2.58 (soil, screening model calculations, Jury et al. 1987a,b; Jury & Ghodrati 1989) 2.35, 2.57 (2 subsurface soils from Oklahoma, Bouchard & Wood 1988) 2.94, 2.68 (mucky peat soil, loam sand soil, quoted, Howard 1991) 2.18, 2.48–2.49, 2.59, 2.66 (soil, quoted values, Bottoni & funari 1992) 2.68 (soil, 20–25°C, selected, Wauchope et al. 1992; Hornsby et al. 1996) 2.21–2.87 (Montgomery 1993) 2.68 (selected, Lohninger 1994) 2.60 (Tomlin 1994) 2.70 (calculated-KOW, Liu & Qian 1995) 2.40 (soil, calculated-MCI 1., Sabljic et al. 1995) 3.07, 2.37, 2.82, 2.51, 2.96 (calculated-KOW; HPLC-screening method with different LC-columns, Szabo et al. 1999) 2.48, 2.42 (soil, estimated-class-specific model, estimated-general model using molecular descriptors, Gramatica et al. 2000) 2.44, 2.43, 2.57 (soils: organic carbon OC . 0.1%, OC . 0.5%, 0.1 . OC < 0.5%, average, Delle Site 2001) 2.78‘ (sediment: organic carbon OC . 0.5%, average, Delle Site 2001) Environmental Fate Rate Constants, k, or Half-Lives, t.: Volatilization: 2.5 . 10–3 h–1 (initial) and 5.3 . 10–4 h–1 (predicted) from soil with t. = 1307 h (Thomas 1982); the calculated t. = 1918 d due to volatilization from soil when incorporated into 1 cm of soil (Jury et al. 1983; quoted, Howard 1991). Photolysis: t. = 2.25 h for 80–84% of 40 µg/mL to degrade in distilled water under 300 nm light (Tanaka et al. 1981; quoted, Cessna & Muir 1991); in surface waters should be photolyzed within a few days (Howard 1991). Oxidation: photooxidation t. = 0.12 d in air, based on estimation for the vapor-phase reaction with hydroxyl radical in the atmosphere (Atkinson 1987; quoted, Howard 1991). Hydrolysis: t. > 4 months for 4660 µg/mL to hydrolyze in phosphate buffer at pH 5–9 and 20°C (El-Dib & Aly 1976; quoted, Muir 1991). Biodegradation: t. = 328 d for a 100 d leaching and screening test in 0–10 cm depth of soil (Rao & Davidson 1980; quoted, Jury et al. 1983, 1984, 1987a); t. = 3–10 d for 40 µg/mL to biodegrade in pond sediment of anaerobic media at 30°C (Attaway et al. 1982a quoted, Muir 1991); t. < 17 d for 40 µg/mL to biodegrade in pond sediment at 30°C (Attaway et al. 1982b; quoted, Muir 1991); 67–99% will be degraded in 10 wk under aerobic conditions by mixed cultures isolated from pond water and sediments forming 6–7 products (Ellis & Camper 1982; quoted, Howard 1991; Muir 1991); t. < 70 d at 30°C (Ellis & Camper 1982; quoted, Muir 1991; Montgomery 1993); t. ~ 5 d for 0.22 µg/mL to biodegrade in pond sediment of anaerobic media (Stepp et al. 1985; quoted, Muir 1991); t.(aerobic) ~ 20 d for 0.0005–10 µg/mL to biodegrade in filtered sewage water at 20°C (Wang et al. 1985; quoted, Muir 1991). © 2006 by Taylor & Francis Group, LLC 3554 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals Biotransformation: ~ 7% of a selection of 90 strains of micromycetes mostly isolated from soil-soil fungi, depleted over 50% of diuron (20 mg/L) in 5-d experiment (Vroumsia et al. 1996) Bioconcentration, Uptake (k1) and Elimination (k2) Rate Constants: Half-Lives in the Environment: Air: t. = 0.12 d, based on estimation for the vapor-phase reaction with hydroxyl radical in the atmosphere (Atkinson 1987; quoted, Howard 1991). Surface water: should be photolyzed within a few days (Howard 1991). Ground water: reported half-lives or persistence, t. = 20–70, 90–180, 200, and 328 d (Bottoni & Funari 1992) Sediment: t. = 3–10 d for 40 µg/mL to biodegrade in pond sediment of anaerobic media at 30°C (Attaway et al. 1982a; quoted, Muir 1991); t. < 17 d for 40 µg/mL to biodegrade in pond sediment at 30°C (Attaway et al. 1982b); t. ~ 5 d for 0.22 µg/mL to biodegrade in pond sediment of anaerobic media (Stepp et al. 1985) Soil: estimated persistence of 10 months in soil (Kearney et al. 1969; quoted, Jury et al. 1987); persistence of 8 months in soil (Edwards 1973; quoted, Morrill et al. 1982); t. = 7.0 months at 15°C and t. = 5.5 months at 30°C in soils (Freed & Haque 1973); persistence of 10 months (Wauchope 1978); rate constant k = 0.0031 d–1 with t. = 328 d under field conditions (Rao & Davidson 1980); calculated t. = 1918 d due to volatilization from soil when incorporated into 1 cm of soil (Jury et al. 1983; quoted, Howard 1991); t. ~ 200–4000 d in loamy sand and peat at 25–35°C as follows (Madhum & Freed 1987): t. = 705, 414, and 225 d at 25, 30, and 35°C, respectively, at herbicide concn at 5 µg/kg, while t. = 1392, 630, and 406 d at 25, 30, and 35°C, respectively, at herbicide concn at 100 µg/kg in an Adkins loamy sand; however, the half-lives were considerable higher in peat. t. = 3991, 2164, and 1165 d at 25, 30, and 35°C, respectively, at herbicide concn at 5 µg/kg while t. = 3416, 1832, and 896 d at 25, 30, and 35°C, respectively, at herbicide concn at 100 µg/kg in a Semiahoo mucky peat (Madhun & Freed 1987) t. = 328 d from screening model calculations (Jury et al. 1987a,b; Jury & Ghodrati 1989); reported t. = 20–70 d, 90–180 d, 200 d and 328 d (Bottoni & Funari 1992); t. = 75–102 d in 0–40 cm soil cores taken, from cultivated field, t. = 55–65 d from meadow and t. = 29–35 d from gravel track (Hassink et al. 1994); selected field t. = 90 d (Wauchope et al. 1992; Hornsby et al. 1996). Biota: biochemical t. = 328 d from screening model calculations (Jury et al. 1987a,b; Jury & Ghodrati 1989). © 2006 by Taylor & Francis Group, LLC Herbicides 3555 17.1.1.34 EPTC Common Name: EPTC Synonym: Eptam, Eradicane, FDA 1541, R 1608, Torbin Chemical Name: carbamic acid, dipropylthio-, S-ethyl ester; S-ethyldipropyl(thiocarbamate); S-ethyldipropylcarbamothioate Uses: selective systemic herbicide for pre-emergence control of perennial and annual grasses, broadleaf weeds. CAS Registry No: 759-94-4 Molecular Formula: C9H19NOS Molecular Weight: 189.318 Melting Point (°C): liquid Boiling Point (°C): 235.0 (Khan 1980; Herbicide Handbook 1989) 127.0 (at 20 mmHg, Hartley & Kidd 1987; Budavari 1989; Worthing & Hance 1991; Montgomery 1993; Tomlin 1994; Milne 1995) Density (g/cm3 at 20°C): 0.9546 (30°C, Spencer 1982; Hartley & Kidd 1987; Montgomery 1993; Tomlin 1994; Milne 1995) 0.960 (25°C, Herbicide Handbook 1989; Montgomery 1993) Molar Volume (cm3/mol): 236.5 (calculated-Le Bas method at normal boiling point) Dissociation Constant pKa: Enthalpy of Fusion, .Hfus (kJ/mol): Entropy of Fusion, .Sfus (J/mol K): Fugacity Ratio at 25°C (assuming .Sfus = 56 J/mol K), F: 1.0 Water Solubility (g/m3 or mg/L at 25°C or as indicated): 375 (shake flask-GC, Freed et al. 1967) 365 (Martin & Worthing 1977) 370 (20°C, Khan 1980; Ashton & Crafts 1981; Herbicide Handbook 1989) 370–375 (Weber et al. 1980) 375 (20°C, Spencer 1982) 370 (Beste & Humburg 1983; Jury et al. 1983, 1984) 375 (Hartley & Kidd 1987; Montgomery 1993; Tomlin 1994) 375 (24°C, Worthing & Walker 1987, Worthing & Hance 1991) 365 (20°C, Budavari 1989; Milne 1995) 344 (20–25°C, selected, Wauchope et al. 1992; Hornsby et al. 1996; Lohninger 1994) Vapor Pressure (Pa at 25°C or as indicated): 4.666 (extrapolated, Patchett et al. 1964) 20.66 (Bailey & White 1965) 1.84 (20°C, effusion method, Hamaker & Kerlinger 1971) 2.16, 2.63, 3.69, 8.266 (23, 24, 28, 40°C, Hamaker 1972) 4.532 (Khan 1980; Ashton & Crafts 1981; Herbicide Handbook 1989) 2.62 (20°C, volatilization rate, Burkhard & Guth 1981) 2.80 (Patchett et al. 1983) 0.612 (20°C, GC-RT correlation, Kim 1985) 4.70 (Hartley & Kidd 1987) 2.00 (20°C, selected, Suntio et al. 1988) 4.532 (35°C, Budavari 1989) 4.50 (Worthing & Hance 1991) O S N © 2006 by Taylor & Francis Group, LLC 3556 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals 4.532 (20–25°C, selected, Wauchope et al. 1992; Hornsby et al. 1996) 4.532 (20°C, Montgomery 1993) 0.00001 (Tomlin 1994) Henry’s Law Constant (Pa·m3/mol at 25°C or as indicated): 1.32 (20°C, volatilization rate, Burkhard & Guth 1981) 1.463 (calculated-P/C, Jury et al. 1983, 1984, 1987a,b; Jury & Ghodrati 1989) 1.02 (20°C, calculated-P/C, Suntio et al. 1988) 1.463 (calculated-P/C, Taylor & Glotfelty 1988) 1.013 (20–25°C, calculated-P/C, Montgomery 1993) 1.023 (calculated-P/C, this work) Octanol/Water Partition Coefficient, log KOW: 1.76 (selected, Dao et al. 1983) 3.21 (shake flask, Log P Database, Hansch & Leo 1987) 3.20 (Worthing & Hance 1991; Montgomery 1993; Tomlin 1994; Milne 1995) 3.21 (recommended, Sangster 1993) 3.21 (recommended, Hansch et al. 1995) 3.45 (RP-HPLC-RT correlation, Finizio et al. 1997) Bioconcentration Factor, log BCF: 1.34 (calculated-S, Kenaga 1980; quoted, Isensee 1991) 1.08 (calculated-KOC, Kenaga 1980) Sorption Partition Coefficient, log KOC: 2.38 (soil, Hamaker & Thompson 1972) 2.45 (soil, Hamaker & Thompson 1972) 2.23 (soil, calculated-S as per Kenaga & Goring 1980, Kenaga 1980) 2.58 (soil, screening model calculations, Jury et al. 1987a,b; Jury & Ghodrati 1989) 2.23–2.38, 2.45 (quoted values, Bottoni & Funari 1992) 2.30 (soil, 20–25°C, selected, Wauchope et al. 1992) 2.38 (Montgomery 1993) 2.30 (selected, Lohninger 1994) 2.45 (selected, Wienhold & Gish 1994) 2.38 (soil, calculated-MCI 1., Sabljic et al. 1995) 2.23, 1.98 (soil, estimated-class specific model, estimated-general model using molecular descriptors, Gramatica et al. 2000) 2.03, 2.00 (soils: organic carbon OC . 0.1%, OC . 0.5%, average, Delle Site 2001) Environmental Fate Rate Constants, k, or Half-Lives, t.: Volatilization: t. = 3.7 d (Jury et al. 1983). Photolysis: rate constant k = 5.2 . 10–3 s–1 for a light intensity corresponding to a 12-h average NO2 photolysis rate with a black lamp spectral distribution (Kwok et al. 1992); photodegradation t. = 14.0 and 18.5 min in water solution under irradiation with UV light at 254 nm (Abu-Qare & Duncan 2002). Oxidation: second order rate constants kOH = (3.10–3.40) . 10–11 cm3 molecule–1 s–1 for gas-phase reaction with OH radical, kNO3 = 0.92 . 10–14 cm3 molecule–1 s–1 with NO3 radical and kO3 < 1.3 . 10–19 cm3 molecule–1 s–1 with O3 at 298 K (Kwok et al. 1992); calculated lifetime of 6 h for the vapor-phase reaction with OH radical in the troposphere (Atkinson et al. 1992; Kwok et al. 1992). Hydrolysis: Biodegradation: t. = 30 d for a 100 d leaching and screening test in 0–10 cm depth of soil (Nash 1980; quoted, Jury et al. 1983, 1984, 1987a; quoted, Grover 1991). © 2006 by Taylor & Francis Group, LLC Herbicides 3557 Biotransformation: Bioconcentration, Uptake (k1) and Elimination (k2) Rate Constants: Half-Lives in the Environment: Air: calculated tropospheric lifetimes are: > 8 h due to photolysis, 5.8 d due to reaction with OH radical, 5.0 d with NO3 radical and > 125 d with O3 (Kwok et al. 1992); calculated lifetime of 6 h for the vapor-phase reaction with OH radical in the troposphere (Atkinson et al. 1992; Kwok et al. 1992). Surface water: t. = 14.0 and 18 min for elimination in water under irradiation with UV light at 254 nm (Abu-Qare & Duncan 2002). Ground water: reported half-lives or persistence, t. = 7 and 30 d (Bottoni & Funari 1992) Sediment: Soil: estimated persistence of 4 months in soil (Kearney et al. 1969; quoted, Jury et al. 1987a); t. = 30 d from screening model calculations (Jury et al. 1987a,b; Jury & Ghodrati 1989); t. ~ 1 wk in moist loam soil at 21 to 27°C (Herbicide Handbook 1974, 1989); reported t. = 7, 30 d (Bottoni & Funari 1992); selected field t. = 6 d (Wauchope et al. 1992; quoted, Richards & Baker 1993; Hornsby et al. 1996). Biota: biochemical t. = 30 d from screening model calculations (Jury et al. 1987a,b; Jury & Ghodrati 1989) © 2006 by Taylor & Francis Group, LLC 3558 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals 17.1.1.35 Ethalfluralin Common Name: Ethalfluralin Synonym: Benzenamine, Somilan, Sonalan, Sonalen Chemical Name: N-ethyl-N-(2-methyl-2-propenyl)-2.6-dinitro-(trifluoromethyl)-benzenamine CAS Registry No: 55283-68-6 Uses: herbicide Molecular Formula: C13H14F3N3O4 Molecular Weight: 333.263 Melting Point (°C): 57 (Lide 2003) Boiling Point (°C): 256 (decomposes, Hartley & Kidd 1987; Tomlin 1994; Milne 1995) Density (g/cm3 at 20°C): 1.32 (Ashton & Crafts 1981; Herbicide Handbook 1989) Molar Volume (cm3/mol): Dissociation Constant pKa: Enthalpy of Fusion, .Hfus (kJ/mol): Entropy of Fusion, .Sfus (J/mol K): Fugacity Ratio at 25°C (assuming .Sfus = 56 J/mol K), F: 0.485 (mp at 57°C) Water Solubility (g/m3 or mg/L at 25°C): 0.21 (Ashton & Crafts 1981) 0.20 (pH 7, Spencer; Hartley & Kidd 1987; Worthing & Walker 1987) 0.30 (pH 7, Herbicide Handbook 1989) 0.30 (selected, Wauchope et al. 1992; Hornsby et al. 1996) 0.30 (pH 7, Tomlin 1994; Milne 1995) 0.40 (Majewski & Capel 1995) Vapor Pressure (Pa at 25°C or as indicated): 1.10 . 10–4 (Worthing & Walker 1983, 1987; Hartley & Kidd 1987) 0.0109 (Spencer 1982; Herbicide Handbook 1989) 0.0117 (selected, Wauchope et al. 1992; Hornsby et al. 1996) 0.0117 (Tomlin 1994) 2.22 . 10–4 (20–25°C, Majewski & Capel 1995) Henry’s Law Constant (Pa·m3/mol at 25°C): 0.183 (calculated-P/C, Majewski & Capel 1995) 13 (calculated-P/C, Wolt 1997) Octanol/Water Partition Coefficient, log KOW: 5.11 (pH 7, Tomlin 1994; Milne 1995) 4.92 (quoted values; selected, Wolt 1997) Octanol/Air Partition Coefficient, log KOA: Bioconcentration Factor, log BCF or log KB: NO2 N NO2 F F F © 2006 by Taylor & Francis Group, LLC Herbicides 3559 Sorption Partition Coefficient, log KOC: 3.60 (selected, soil, Wauchope et al. 1992; Hornsby et al. 1996) 3.60–3.90 (soil, Tomlin 1994) 3.61–3.92 (soil, Wolt 1997) Environmental Fate Rate Constants, k, or Half-Lives, t.: Volatilization: Photolysis: t. = 6.3 h in aqueous phase and t. = 2 h in vapor phase (Tomlin 1994); Aqueous photolysis t. = 6.3 h in pH 5 sterile buffer solution; soil photolysis t. = 14.2 d in air-dry sandy loam soil when exposed to a xenon light source; air photolysis t. = 2 h when exposed to a light source simulating summer sunlight at 34°C (Wolt 1997). Oxidation: Hydrolysis: no hydrolysis after 33 d at pH 3, 6 and 9 (51°C, Tomlin 1994); stable in sterile, buffered solutions across a range of pH (Wolt 1997). Biodegradation:. Biotransformation: t. = 45 d for aerobic metabolism in sandy loam soils and t. = 14 d for more rapid metabolism anaerobically in the same soil (quoted, Tomlin 1994; Wolt 1997). Bioconcentration, Uptake (k1) and Elimination (k2) Rate Constants: Half-Lives in the Environment: Air: air photolysis t. = 2 h when exposed to a light source simulating summer sunlight at 34°C (Wolt 1997). Surface water: water photolysis t. = 6.3 h in pH 5 sterile buffer solution; t. = 2 d for dissipation from the water column in a pond water-sediment system under outdoor conditions (Wolt 1997). Ground water: Sediment: t. = 38 h in anaerobic pond water sediment system (Wolt 1997). Soil: reported field t. = 30–60 d, 60 d, 25–46 d; recommended t. = 60 d (Wauchope et al. 1992; Hornsby et al. 1996); t. = 45 d for aerobic metabolism in sandy loam soils and t. = 14 d for more rapid metabolism anaerobically in the same soil (Tomlin 1994); terrestrial filed dissipation t. = 4–146 d, t. = 45 d in moist aerobic soil, t. = 14 d in anaerobic soil shifted to anaerobic conditions (Wolt 1997). Biota: © 2006 by Taylor & Francis Group, LLC 3560 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals 17.1.1.36 Fenoprop Common Name: Fenoprop Synonym: Silvex, 2,4,5-TP, Kuron, Kurosal, Fruitone T Chemical Name: 2-(2,4,5-trichlorophenoxy) propionic acid CAS Registry No: 93-72-1 Uses: herbicide/growth regulator Molecular Formula: C9H7Cl3O3 Molecular Weight: 269.509 Melting Point (°C): 181.6 (Lide 2003) Boiling Point (°C): Density (g/cm3 at 20°C): Molar Volume (cm3/mol): Dissociation Constant pKa: 2.84 (Worthing 1983, 1987; Augustijn-Beckers et al. 1994) Enthalpy of Vaporization, .HV (kJ/mol): 75.75 (Rordorf 1989) Enthalpy of Fusion, .Hfus (kJ/mol): 44.6 (Rordorf 1989) Entropy of Fusion, .Sfus (J/mol K): Fugacity Ratio at 25°C (assuming .Sfus = 56 J/mol K), F: 0.0291 (mp at 181.6°C) Water Solubility (g/m3 or mg/L at 25°C): 140 (Kenaga & Goring 1980, Kenaga 1980a,b, Spencer 1982) 140 (Worthing & Walker 1983, 1987; Budavari 1989) 200 (Verschueren 1983) 176 (Hartley & Kidd 1987) 12.0 (calculated-MCI ., Patil 1994) 140 (selected, Augustijn-Beckers et al. 1994; Hornsby et al. 1996) Vapor Pressure (Pa at 25°C or as indicated and reported temperature dependence equations): 2.30 . 10–3, 4.40 . 10–2, 0.55, 4.90, 34.0 (25, 50, 70, 100, 125°C, gas saturation-GC, Rordorf 1989) log (PS/Pa) = 13.953 – 4948/(T/K); measured range 85.4–181°C (gas saturation-GC, Rordorf 1989) log (PL/Pa) = 11.727 – 3956.9/(T/K); measured range 181–211°C (gas saturation-GC, Rordorf 1989) < 1.33 . 10–6 (estimated, Augustijn-Beckers et al. 1994; Hornsby et al. 1996) Henry’s Law Constant (Pa·m3/mol): Octanol/Water Partition Coefficient, log KOW: 2.44 (Kenaga 1980a) 3.86 (estimated, Garten & Trabalka 1983) 3.13 (counter-current chromatography, Ilchmann et al. 1993) 2.75 (calculated-MCI ., Patil 1994) 3.80 (selected, Hansch et al. 1995) Octanol/Air Partition Coefficient, log KOA: Bioconcentration Factor, log BCF or log KB: 1.76 (calculated, Kenaga 1980a) 1.58, 2.23 (calculated-solubility, KOW, Kenaga 1980b) Cl Cl Cl O OH O © 2006 by Taylor & Francis Group, LLC Herbicides 3561 1.76 (fish, flowing water, Garten & Grabalka 1983) 2.35 (Isensee 1991) Sorption Partition Coefficient, log KOC: 3.41 (soil, Kenaga & Goring 1980) 2.46 (calculated-KOW, Kenaga 1980b) 1.91 (soil: calculated-MCI ., Meylan et al. 1992) 2.48 (soil, selected, Augustijn-Beckers et al. 1994; Hornsby et al. 1996) 3.28 (soil, calculated-MCI ., Sabljic et al. 1995) Environmental Fate Rate Constants, k, or Half-Lives, t.: Biodegradation: t. > 205 d for ring cleavage in soil suspensions (Verschueren 1983) Half-Lives in the Environment: Soil: persistence 47–205 d in soil (Alexander et al. 1961) degradation t. = 21 d and 14 d in Quachita Highlands’ forest and grassland soil respectively, t. = 15 d in gross timbers forest soil, average t. = 17 d in 3 soils (Altom & Stritzke 1973); t. = 5–11 d in a microagroecosystem study (Nash 1983); t. > 205 d for ring cleavage in soil suspensions (Verschueren 1983); field t. = 21 d (Augustijn-Beckers et al. 1994; Hornsby et al. 1996) © 2006 by Taylor & Francis Group, LLC 3562 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals 17.1.1.37 Fenuron Common Name: Fenuron Synonym: Dozer, Dybar, Falisilvan, Fenidim, Fenulon, Urab Chemical Name: 1,1-dimethyl-3-phenylurea; N,N-dimethyl-N.-phenylurea Uses: herbicide to control woody plants and deep-rooted perennial weeds, often used in combination with chlorpropham to extend its weed control spectrum and range of crops. CAS Registry No: 101-42-8 Molecular Formula: C9H12N2O Molecular Weight: 164.203 Melting Point (°C): 132 (Lide 2003) Boiling Point (°C): Density (g/cm3 at 20°C): 1.13 (25°C, Hartley & Kidd 1987) 1.08 (Worthing & Hance 1991; Tomlin 1994) Molar Volume (cm3/mol): 182.0 (calculated-Le Bas method at normal boiling point) 159.0 (modified Le Bas method, Spurlock & Biggar 1994a) Dissociation Constant pKa: Enthalpy of Fusion, .Hfus (kJ/mol): 24.267 (DSC method, Plato & Glasgow 1969) Entropy of Fusion, .Sfus (J/mol K): Fugacity Ratio at 25°C (assuming .Sfus = 56 J/mol K), F: 0.0892 (mp at 132°C) Water Solubility (g/m3 or mg/L at 25°C or as indicated): 2600 (Freed 1966) 2400 (Gunther et al. 1968) 3850 (Martin & Worthing 1977; Kenaga 1980; Kenaga & Goring 1980; Verschueren 1983) 3850 (Khan 1980; Weber et al. 1980; Ashton & Crafts 1981; Willis & McDowell 1982) 3700 (shake flask-HPLC, Ellgehausen et al. 1981) 3850 (Hartley & Kidd 1987; Worthing & Walker 1987, Worthing & Hance 1991; Tomlin 1994) 3000 (20°C, selected, Suntio et al. 1988) 3900 (Spurlock 1992; Spurlock & Biggar 1994b) 3850 (20–25°C, selected, Augustijn-Beckers et al. 1994; Hornsby et al. 1996) Vapor Pressure (Pa at 25°C or as indicated): 0.0213 (60°C, Khan 1980; Verschueren 1983) 0.0210 (60°C, Hartley & Kidd 1987) 0.0050 (20°C, selected, Suntio et al. 1988) 0.0210 (60°C, Worthing & Hance 1991; Tomlin 1994) 0.0267 (20–25°C, selected, Augustijn-Beckers et al. 1994; Hornsby et al. 1996) Henry’s Law Constant (Pa·m3/mol at 25°C at 25°C or as indicated): 0.00027 (20°C, calculated-P/C, Suntio et al. 1988) Octanol/Water Partition Coefficient, log KOW: 0.98 (shake flask-UV, Hansch & Anderson 1967) 1.00 (Leo et al. 1971) 1.00 (shake flask-UV, Lord et al. 1980) HN N O © 2006 by Taylor & Francis Group, LLC Herbicides 3563 0.96 (shake flask-UV, Briggs 1981; Karickhoff 1981) 0.88 (shake flask-HPLC, Ellgehausen et al. 1981) 0.62 (HPLC-k. correlation, McDuffie 1981) 0.70 (Elgar 1983) 1.18 (RP-HPLC-k. correlation, Braumann et al. 1983) 1.00 (shake flask-HPLC, Spurlock & Biggar 1994a) 0.98 (recommended, Sangster 1993) 1.18 (RP-HPLC-RT correlation, Sicbaldi & Finizio 1993) 0.98 (recommended, Hansch et al. 1995) 1.18 (RP-HPLC-RT correlation, Finizio et al. 1997) Bioconcentration Factor, log BCF: 0.778 (calculated-S, Kenaga 1980) 0.0 (calculated-KOC, Kenaga 1980) 1.34 (earthworms, Lord et al. 1980) 0.699, 0.602 (cuticle/water: tomato, pepper, Evelyne et al. 1992) Sorption Partition Coefficient, log KOC: 1.43 (soil, Hamaker & Thompson 1972) 1.67 (soil, calculated-S as per Kenaga & Goring 1980, Kenaga 1980) 0.88 (reported as log KOM, Briggs 1981) 0.61 (estimated-KOW, Karickhoff 1981) 1.80, 1.86 (estimated-S, Karickhoff 1981) 0.72, 0.84 (estimated-S and mp, Karickhoff 1981) 1.74 (calculated-MCI ., Gerstl & Helling 1987) 1.62 (20–25°C, selected, Augustijn-Beckers et al. 1994; Hornsby et al. 1996) 1.40 (soil, calculated-MCI 1., Sabljic et al. 1995) 1.40; 1.40, 1.70 (soil, quoted obs.; estimated-class-specific model, estimated-general model using molecular descriptors, Gramatica et al. 2000) 1.42, 1.41 (soils: organic carbon OC . 0.1%, OC . 0.5%, average, Delle Site 2001) Environmental Fate Rate Constants, k, or Half-Lives, t.: Biodegradation: aerobic t. . 10 d for 0.01 µg/mL to biodegrade in river water (Eichelberger & Lichtenberg 1971; quoted, Muir 1991). Half-Lives in the Environment: Air: Surface water: aerobic t. .10 d for 0.01 µg/mL to biodegrade in river water (Eichelberger & Lichtenberg 1971; quoted, Muir 1991); persistence of up to 4 weeks in river water (Eichelberger & Lichtenberg 1971). Ground water: Sediment: Soil: t. = 4.5 months at 15°C and 2.2 months at 30°C in soils (Freed & Haque 1973); persistence of 8 months in soil (Edwards 1973; quoted, Morrill et al. 1982); selected field t. = 60 d (Augustijn-Beckers et al. 1994; Hornsby et al. 1996). Biota: © 2006 by Taylor & Francis Group, LLC 3564 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals 17.1.1.38 Fluchloralin Common Name: Fluchloralin Synonym: BAS-392H, Basalin Chemical Name: N-(2-chloroethyl)-2,6-dinitro-N-propyl-4-(trifluoromethyl)benzenamine; N-(2-chloroethyl).,.,.-trifluoro- 2,6-dinitro-N-propyl-p-toluidine Uses: herbicide for pre-plant or pre-emergence control of annual grass and broadleaf weeds in cotton, groundnuts, jute, potatoes, rice soybeans, and sunflowers, etc. CAS Registry No: 33245-39-5 Molecular Formula: C12H13ClF3N3O4 Molecular Weight: 355.697 Melting Point (°C): 42 (Lide 2003) Boiling Point (°C): Density (g/cm3 at 20°C): Molar Volume (cm3/mol): 326.1 (calculated-Le Bas method at normal boiling point) Dissociation Constant pKa: Enthalpy of Fusion, .Hfus (kJ/mol): Entropy of Fusion, .Sfus (J/mol K): Fugacity Ratio at 25°C (assuming .Sfus = 56 J/mol K), F: 0.681 (mp at 42°C) Water Solubility (g/m3 or mg/L at 25°C or as indicated): 1.00 (20°C, Weber 1972; Ashton & Crafts 1981) 1.00 (Edwards 1977) < 1.0 (Martin & Worthing 1977; Herbicide Handbook 1978, 1989) 0.70 (20°C, Spencer 1982) < 1.0 (Worthing & Walker 1987, 1991; Tomlin 1994) 10 (Budavari 1989; Milne 1995) 0.90 (20–25°C, selected, Augustijn-Beckers et al. 1994; Hornsby et al. 1996) 0.50 (selected, Lohninger 1994) Vapor Pressure (Pa at 25°C or as indicated): 0.0033 (20°C, Weber 1972; Worthing & Walker 1987) 0.373 (20°C, Ashton & Crafts 1981) 0.0008, 0.0033, 0.0133, 0.533 (20, 30, 40, 50°C, gas saturation, Spencer 1982) 0.0035 (Herbicide Handbook 1983; quoted, Nash 1988) 0.0037, 0.0033 (20°C, 30°C, Herbicide Handbook 1989) 0.004 (20°C, Worthing & Hance 1991; Tomlin 1994) 0.004 (20–25°C, selected, Augustijn-Beckers et al. 1994; Hornsby et al. 1996) Henry’s Law Constant (Pa·m3/mol at 25°C or as indicated): 1.174 (20°C, calculated-P/C, Muir 1991) 1.343 calculated-P/C, this work) Octanol/Water Partition Coefficient, log KOW: 4.63 (selected, Magee 1991) N NO2 O2N F F F Cl © 2006 by Taylor & Francis Group, LLC Herbicides 3565 4.70 (CLOGPSTAR or CLOGP data, Sabljic et al. 1995) Bioconcentration Factor, log BCF: > 2.79, 2.40 (calculated-S, calculated-KOC, Kenaga 1980) Sorption Partition Coefficient, log KOC: 3.56 (soil, Harvey 1974) 3.60 (soil, Kenaga 1980) > 3.64 (soil, calculated-S as per Kenaga & Goring 1980, Kenaga 1980) 4.25 (calculated-MCI ., Bahnick & Doucette 1988) 3.56; 3.58 (reported as log KOM, estimated as log KOM, Magee 1991) 3.48 (20–25°C, estimated, Augustijn-Beckers et al. 1994; Hornsby et al. 1996) 3.80 (estimated-chemical structure, Lohninger 1994) 3.55 (soil, calculated-MCI 1., Sabljic et al. 1995) 3.55; 4.02 (soil, quoted obs.; estimated-general model using molecular descriptors, Gramatica et al. 2000) Environmental Fate Rate Constants, k, or Half-Lives, t.: Volatilization: estimated t. ~ 1 d from 1 m depth of water (20°C, Muir 1991). Photolysis: t. = 13 d for 84% of 5 µg/mL to degrade in distilled water under sunlight (Nilles & Zabik 1974; quoted, Cessna & Muir 1991); t. = 8 h for 50% of 2000 µg/mL to degrade in methanol under sunlight (Plimmer & Klingebiel 1974; quoted, Cessna & Muir 1991). Oxidation: Hydrolysis: Biodegradation: t. = 8 d for 0.5 µg/mL to biodegrade in soil at 20–42°C (Savage 1978; quoted, Muir 1991); t. = 3.6 wk for 2.0 µg/mL to biodegrade in soil at 25°C (Brewer et al. 1982; quoted, Muir 1991). Biotransformation: Bioconcentration, Uptake (k1) and Elimination (k2) Rate Constants: Half-Lives in the Environment: Soil: t. = 8 d for 0.5 µg/mL to biodegrade in soil at 20–42°C (Savage 1978; quoted, Muir 1991); t. = 1.5 d on Bosket silt loam, t. = 4 d on Sharkey clay for the first 3 to 5 days when sprayed onto soil surface, rate of loss much slower for the remainder of the 7- or 12-d sampling period with t. = 13 d on Bosket silt loam, t. = 8 d on Sharkey clay (Savage & Jordon 1980) measured dissipation rate k = 0.099–0.13 d–1 (derived from Savage & Jordan 1980, Nash 1988); field studies, t. = 12.2 wk - 1978 first study; t. = 13.0 wk -1978 second study; t. = 17.6 wk -1979, in a Crowley silt loam at Stuttgart, Arkansas (Brewer et al. 1982) Laboratory studies: t. = 28.7 wk at 4°C, 10.5 wk at 25°C for soils of field capacity moisture (27% w/w for Crowley silt loam) and t. = 20.8 wk at 4°C, t. = 8.4 wk at 25°C for flooded soil of Crowley silt loam; t. = 29.3 wk at 4°C, t. = 10.5 wk at 25°C for soil of field capacity moisture (34% w/w for Sharkey silty clay) and t. = 20.8 wk at 4°C and t. = 4.3 wk at 25°C for flooded soil, Sharkey silty clay (Brewer et al. 1982); t. = 3.6 wk for 2.0 µg/mL to biodegrade in soil at 25°C (derived form Brewer et al. 1982, Muir 1991); estimated dissipation rate k = 0.29, and 0.120 d–1 (Nash 1988); estimated field t. ~ 60 d (Augustijn-Beckers et al. 1994; Hornsby et al. 1996). © 2006 by Taylor & Francis Group, LLC 3566 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals 17.1.1.39 Fluometuron Common Name: Fluometuron Synonym: CIBA 2059, Cotoran, Cottonex, Higalcoton, Lanex, Meturon, Pakhtaran Chemical Name: 1,1-dimethyl-3-(.,.,.-trifluoro-m-tolyl)urea; N,N-dimethyl-N.-[3-(trifluoromethyl)phenyl]urea Uses: herbicide to control many annual broadleaf weeds in sugar cane and cotton. CAS Registry No: 2164-17-2 Molecular Formula: C10H11F3N2O Molecular Weight: 232.201 Melting Point (°C): 163–164.5 (Hartley & Kidd 1987; Herbicide Handbook 1989; Worthing & Hance 1991; Montgomery 1993; Tomlin 1994; Milne 1995) 164 (Lide 2003) Boiling Point (°C): Density (g/cm3 at 20°C): 1.390 (Hartley & Kidd 1987; Worthing & Hance 1991; Montgomery 1993; Tomlin 1994; Milne 1995) Molar Volume (cm3/mol): 229.7 (calculated-Le Bas method at normal boiling point) 167.1 (calculated-density) Dissociation Constant pKa: –1.00 (Sangster 1993) Enthalpy of Fusion, .Hfus (kJ/mol): 29.706 (DSC method, Plato 1972) Entropy of Fusion, .Sfus (J/mol K): Fugacity Ratio at 25°C (assuming .Sfus = 56 J/mol K), F: 0.0433 (mp at 164°C) Water Solubility (g/m3 or mg/L at 25°C or as indicated): 90 (Melnikov 1971; Spencer 1973, 1982; quoted, Wauchope 1978; Khan 1980; Weber et al. 1980) 90 (20°C, Martin & Worthing 1977; Herbicide Handbook 1978,89) 106 (shake flask-UV, Briggs 1981) 90 (Herbicide Handbook 1983) 105 (20°C, Hartley & Kidd 1987; Worthing & Walker 1987, 1991) 110 (20–25°C, selected, Wauchope et al. 1992; Hornsby et al. 1996) 80 (Montgomery 1993) 110 (Tomlin 1994) Vapor Pressure (Pa at 25°C or as indicated): 6.70 . 10–5 (20–25°C, Weber et al. 1980) 6.70 . 10–5 (Herbicide Handbook 1983) 6.70 . 10–5 (20°C, Hartley & Kidd 1987; Herbicide Handbook 1989; Montgomery 1993) 6.60 . 10–5 (20°C, Worthing & Hance 1991) 1.25 . 10–4 (20–25°C, selected, Wauchope et al. 1992; Hornsby et al. 1996) 1.25 . 10–4 (Tomlin 1994) Henry’s Law Constant (Pa·m3/mol at 25°C or as indicated): < 0.283 (20–25°C, calculated-P/C, Montgomery 1993) 1.73 . 10–4 (calculated-P/C, this work) HN N O F F F © 2006 by Taylor & Francis Group, LLC Herbicides 3567 Octanol/Water Partition Coefficient, log KOW: 1.34 (Briggs 1969) 2.42 (shake flask-UV, Briggs 1981) 1.88 (shake flask-UV, pH 5, Barak et al. 1983) 2.40 (selected, Gerstl & Helling 1987) 2.23 (Worthing & Hance 1991; Tomlin 1994; Milne 1995) 2.23, 2.38 (Montgomery 1993) 2.03 (RP-HPLC-RT correlation, Sicbaldi & Finizio 1993) 2.20 (recommended, Sangster 1993) 2.42 (recommended, Hansch et al. 1995) 2.03 (RP-HPLC-RT correlation, Finizio et al. 1997) Bioconcentration Factor, log BCF: 1.67 (calculated-S, Kenaga 1980) 0.954 (calculated-KOC, Kenaga 1980) Sorption Partition Coefficient, log KOC: 2.24 (soil, Abernethy & Davidson 1971; Davidson & McDougal 1973; Savage & Wauchope 1974; Carringer et al. 1975; Wood & Davidson 1975) 2.30 (soil, Kenaga 1980) 2.57 (soil, calculated-S as per Kenaga & Goring 1980, Kenaga 1980) 1.82 (soil, converted from reported KOM multiplied by 1.724, Briggs 1981) 2.30 (calculated-MCI ., Gerstl & Helling 1987) 2.00 (soil, 20–25°C, selected, Wauchope et al. 1992; Hornsby et al. 1996) 1.46–2.08 (Montgomery 1993) 2.00 (estimated-chemical structure, Lohninger 1994) 1.49–2.07 (Tomlin 1994) 2.00 (soil, calculated-MCI 1., Sabljic et al. 1995) 2.33; 2.66., 2.03, 2.64, 2.36, 1.94 (quoted lit., calculated-KOW; HPLC-screening method with different LC-columns, Szabo et al. 1999) 2.14, 2.51 (soil, estimated-class-specific model, estimated-general model using molecular descriptors, Gramatica et al. 2000) Environmental Fate Rate Constants, k, or Half-Lives, t.: Volatilization: Photolysis: t. = (11 ± 2 h) in 10 ppm aqueous solutions under summer sunlight of 9.1 h/d exposure and t. = (33 ± 16) h under spring sunlight of 3.7 h/d exposure (Burkhard et al. 1975). Oxidation: Hydrolysis: t. = 1.6 yr at 20°C and pH 1, t. = 2.4 yr at pH 5, and t. = 2.8 yr at pH 9 (Montgomery 1993). Biodegradation: Biotransformation: Bioconcentration, Uptake (k1) and Elimination (k2) Rate Constants: Half-Lives in the Environment: Air: Surface water: t. = 730–1010 d at pH 5–9 and 20°C in aqueous solutions (Herbicide Handbook 1989). Ground water: Sediment: Soil: measured dissipation rate k = 0.023–0.043 d–1 (Horowitz & Herzlinger 1974: quoted, Nash 1988); estimated dissipation rate k = 0.0012, and 0.011 d–1 (Nash 1988); persistence of 4 months in soil (Wauchope 1978); selected field t. = 85 d (Wauchope et al. 1992; Hornsby et al. 1996); soil t. = 30 d (Pait et al. 1992); median t. ~ 30 d in soil (Herbicide Handbook 1989; Tomlin 1994). Biota: © 2006 by Taylor & Francis Group, LLC 3568 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals 17.1.1.40 Fluorodifen Common Name: Fluorodifen Synonym: Preforan, Soyex Chemical Name: 4-nitrophenyl .,.,.-trifluoro-2-nitro-p-tolyl ether Uses: herbicide. CAS Registry No: 15457-05-3 Molecular Formula: C13H7F3N2O5 Molecular Weight: 328.200 Melting Point (°C): 94 (Spencer 1982; Milne 1995; Lide 2003) Boiling Point (°C): Density (g/cm3 at 20°C): Molar Volume (cm3/mol): 282.6 (calculated-Le Bas method at normal boiling point) Dissociation Constant pKa: Enthalpy of Fusion, .Hfus (kJ/mol): Entropy of Fusion, .Sfus (J/mol K): Fugacity Ratio at 25°C (assuming .Sfus = 56 J/mol K), F: 0.210 (mp at 94°C) Water Solubility (g/m3 or mg/L at 25°C or as indicated): 2.0 (20°C, Spencer 1973, 1982) < 2.0 (Weber et al. 1980) 2.0 (shake flask-HPLC, Ellgehausen et al. 1981) 2.0 (20°C, Worthing & Walker 1987, Worthing & Hance 1991) Vapor Pressure (Pa at 25°C or as indicated): 9.33 . 10–6 (20°C, Spencer 1982) Henry’s Law Constant (Pa·m3/mol): Octanol/Water Partition Coefficient, log KOW: 3.30 (shake flask-HPLC, Ellgehausen et al. 1980; Geyer et al. 1991) 4.40 (20 ± 2°C, shake flask-UV, Briggs 1981) 3.65 (shake flask-HPLC, Ellgehausen et al. 1981) 3.60 (HPLC-RT correlation, Nandihalli et al. 1993) 3.65 (recommended, Sangster 1993) 3.65 (recommended, Hansch et al. 1995) Bioconcentration Factor, log BCF: 2.019 (algae, log BF-bioaccumulation factor, Ellgehausen et al. 1980) 2.386 (catfish, log BF-bioaccumulation factor, Ellgehausen et al. 1980) 1.178 (daphnids, log BF-bioaccumulation factor, Ellgehausen et al. 1980) Sorption Partition Coefficient, log KOC: 3.13 (calculated-MCI ., Gerstl & Helling 1987) Environmental Fate Rate Constants, k, or Half-Lives. t.: Half-Lives in the Environment: O O2N O2N F F F © 2006 by Taylor & Francis Group, LLC Herbicides 3569 17.1.1.41 Fluridone Common Name: Fluridone Synonym: Brake, EL-171, Fluridon, Pride, Sonar Chemical Name: 1-methyl-3-phenyl-5-[3-(trifluoromethyl)phenyl] 4(1H)-pyridinone; 1-methyl-3-phenyl-5-( ., ., .-trifluorom- tolyl)-4-pyridone Uses: herbicide to control annual grass and broadleaf weeds and certain perennial species in cotton; also used to control aquatic weeds and plants in lakes, ponds, ditches, etc. CAS Registry No: 59756-60-4 Molecular Formula: C19H14F3NO Molecular Weight: 329.315 Melting Point (°C): 155 (Lide 2003) Boiling Point (°C): Density (g/cm3 at 20°C): Molar Volume (cm3/mol): 333.5 (calculated-Le Bas method at normal boiling point) Dissociation Constant: 12.3 (pKb, Wauchope et al. 1992) Enthalpy of Fusion, .Hfus (kJ/mol): Entropy of Fusion, .Sfus (J/mol K): Fugacity Ratio at 25°C (assuming .Sfus = 56 J/mol K), F: 0.0530 (mp at 155°C) Water Solubility (g/m3 or mg/L at 25°C or as indicated): 12.0 (20°C, Weber 1972; Worthing & Walker 1987) 12.0 (Kenaga 1980) 12.0 (Herbicide Handbook 1983, 1989; Budavari 1989; Milne 1995) 12.0 (Hartley & Kidd 1987; Worthing & Walker 1987, Worthing & Hance 1991) 10.0 (20–25°C, selected, Wauchope et al. 1992; Hornsby et al. 1996) 10.0 (selected, Lohninger 1994) Vapor Pressure (Pa at 25°C or as indicated): 1.31 . 10–5 (20°C, Weber 1972; Worthing & Walker 1987) 1.00 . 10–5 (Herbicide Handbook 1983) 0.013 (Hartley & Kidd 1987; Worthing & Hance 1991) 1.33 . 10–5 (Herbicide Handbook 1989) 1.33 . 10–5 (20–25°C, selected, Wauchope et al. 1992; Hornsby et al. 1996) 1.30 . 10–5 (Tomlin 1994) Henry’s Law Constant (Pa·m3/mol at 25°C or as indicated): 3.59 . 10–4 (20°C, calculated-P/C, Muir 1991) Octanol/Water Partition Coefficient, log KOW: 1.87 (Reinert 1989) 1.87 (Worthing & Hance 1991; Tomlin 1994; Milne 1995) 2.98 (shake flask, Takahashi et al. 1993; quoted, Sangster 1993) 3.16 (LOGPSTAR or CLOGP data, Sabljic et al. 1995) F F F N O © 2006 by Taylor & Francis Group, LLC 3570 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals Bioconcentration Factor, log BCF: 2.18 (calculated-S, Kenaga 1980; quoted, Isensee 1991) 0.778 (measured, West et al. 1983; quoted, Isensee 1991) Sorption Partition Coefficient, log KOC at 25°C or as indicated: 1.60 (soil, Kenaga 1980) 2.97–3.39 (pond sediment, Muir et al. 1980) 3.36, 2.95 (lake and river sediment, Muir et al. 1980) 2.94 (Reinert 1989) 2.90, 3.81, 3.03 (Norfolk sand pH 6.0, Norfold with montmorillonite pH 5.9, Norfolk sand with added organic matter pH 5.3, Reinert 1989) 3.43, 2.57, 2.43 (California soil at pH 6, 7, 7.3, Reinert 1989) 3.00 (20–25°C, selected, Wauchope et al. 1992; Hornsby et al. 1996) 3.00 (selected, Lohninger 1994) 2.85 (soil, calculated-MCI 1., Sabljic et al. 1995) Environmental Fate Rate Constants, k, or Half-Lives, t.: Volatilization: estimated t. = 10,000 d from 1 m depth of water at 20°C (Muir 1991). Photolysis: t. . 23 h to degrade in distilled water under > 290 nm light (West et al. 1979; quoted, Cessna & Muir 1991); t. . 6 h for 5 µg/mL to degrade in nonsterile pond water under sunlight (Muir & Grift 1982; quoted, Cessna & Muir 1991); t. = 27 d for 85% of 10 µg/mL to degrade in distilled water and for 85% of 10 µg/mL to degrade in lake water at pH 8.4 both under sunlight (Sanders & Mosier 1983; quoted, Cessna & Muir 1991; Howard et al. 1991) resistance to decomposition by UV light with t. = 23 h in deionized water (Herbicide Handbook 1989). Oxidation: photooxidation t. = 0.359–3.20 h, based on estimated rate constant for reaction with hydroxyl radicals (Atkinson 1987; quoted, Howard et al. 1991) and ozone (Atkinson & Carter 1984; quoted, Howard et al. 1991). Hydrolysis: t. > 113 d for 1 µg/mL to hydrolyze in pond water at 4°C (Ghassemi et al. 1981; quoted, Muir 1991); t. = 23 h in water (Tomlin 1994). Biodegradation: aqueous aerobic t. = 44–192 d, based on soil die-away test data and field study soil persistence (Banks et al. 1979; quoted, Howard et al. 1991); t. = 12 months for 5 µg/mL to biodegrade in static sediment and water, and t. . 9 months in aerobic and anaerobic sediment and water all at 25°C (Muir & Grift 1982; quoted, Muir 1991); aqueous anaerobic t. = 176 d to 2.1 yr, based on estimated unacclimated aqueous aerobic biodegradation half-life (Howard et al. 1991); microbial degradation t. > 343 d at pH 7.3 with 2.6% organic matter in a silt loam soil (Tomlin 1994). Biotransformation: Bioconcentration, Uptake (k1) and Elimination (k2) Rate Constants: k1 = 0.9–1.3 h–1 (Chironomus tentans larvae in pond sediment-water system, 96-h exposure, calculated by using first-order kinetic and concn factors, Muir et al. 1983) k1 = 0.70–5.6 h–1 (Chironomus tentans larvae in river sediment-water system, 96-h exposure, calculated by using first-order kinetic and concn factors, Muir et al. 1983) k1 = 1.7–3.40 h–1 (Chironomus tentans larvae in sediment (sand)-water system, 96-h exposure, calculated by using first-order kinetic and concn factors, Muir et al. 1983) k1 = 1.7–2.1 h–1 (Chironomus tentans larvae in sediment (sand)-water system, 96-h exposure, calculated by using initial uptake data of 0–12 h, Muir et al. 1983) k2 = 0.052 h–1 (Chironomus tentans larvae in pond sediment-water system, calculated by concentration decay curve, Muir et al. 1983) k2 = 0.118 h–1 (Chironomus tentans larvae in river water system, calculated by concentration decay curve, Muir et al. 1983) k2 = 0.055 h–1 (Chironomus tentans larvae in river sediment-water system, calculated by concentration decay curve, Muir et al. 1983) © 2006 by Taylor & Francis Group, LLC Herbicides 3571 k2 = 0.041 h–1 (Chironomus tentans larvae in sediment (sand)-water system, calculated by concentration decay curve, Muir et al. 1983) Half-Lives in the Environment: Air: t. = 0.359–3.20 h, based on estimated rate constant for reaction with hydroxyl radicals (Atkinson 1987; quoted, Howard et al. 1991) and ozone (Atkinson & Carter 1984; quoted, Howard et al. 1991). Surface water: t. ~ 21 d in water (Hartley & Kidd 1987); t. = 288–864 h, based on estimated photolysis half-life in water (Howard et al. 1991); anaerobic t. = 9 months and aerobic t. ~ 20 d (Tomlin 1994). Ground water: t. = 2112–9216 h, based on estimated unacclimated aqueous aerobic biodegradation half-life (Howard et al. 1991). Sediment: t. = 12 months for 5 µg/mL to biodegrade in static sediment and water, and t. . 9 months in aerobic and anaerobic sediment and water all at 25°C (Muir & Grift 1982; quoted, Muir 1991). Soil: measured dissipation rate k = 0.0041 d–1 (Banks et al. 1979; quoted, Nash 1988) with estimated t. = 44–192 d (Banks et al. 1979; quoted, Howard et al. 1991); estimated dissipation rate k = 0.0067 and 0.025 d–1 (Nash 1988); selected field t. = 21 d (Wauchope et al. 1992; Hornsby et al. 1996); t. ~ 90 d in the hydrosoil (Tomlin 1994). Biota: elimination t. = 13.2 h in pond sediment-water, t. = 5.9 h in river water, t. = 12.5 h in river sedimentwater, t. = 16.9 in sand-water systems (Chironomus tentans larvae, Muir et al. 1983) © 2006 by Taylor & Francis Group, LLC 3572 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals 17.1.1.42 Glyphosate Common Name: Glyphosate Synonym: Mon-0573, 0468, 2139; Polado, Roundup Chemical Name: N-(phosphoromethyl)glycine Uses: nonselective, post-emergent, broad spectrum herbicide to control annual and perennial grasses, sedges, broadleaf, and emerged aquatic weeds; also used to control insects on fruit trees. CAS Registry No: 1071-83-6 Molecular Formula: C3H8NO5P Molecular Weight: 169.074 Melting Point (°C): 230 (dec., Montgomery 1993; Milne 1995; Lide 2003) Boiling Point (°C): Density (g/cm3 at 20°C): 1.74 (Herbicide Handbook 1989; Montgomery 1993) Molar Volume (cm3/mol): Dissociation Constant pKa: 5.70 (Worthing & Hance 1991) 2.60, 5.90, 10.40 (pK1, pK2, pK3, Yao & Haag 1991; Haag & Yao 1992) 2.32, 5.86, 10.86 (pK1, pK2, pK3, Montgomery 1993; Hornsby et al. 1996) Enthalpy of Fusion, .Hfus (kJ/mol): Entropy of Fusion, .Sfus (J/mol K): Fugacity Ratio at 25°C (assuming .Sfus = 56 J/mol K), F: 0.0097 (mp at 230°C) Water Solubility (g/m3 or mg/L at 25°C): 10000 (Spencer 1973, 1982; Herbicide Handbook 1978; Ashton & Crafts 1981) 12000 (Martin & Worthing 1977; Worthing & Walker 1987, Worthing & Hance 1991; Tomlin 1994) 15700 (Herbicide Handbook 1989) 12000 (Budavari 1989; Montgomery 1993; Milne 1995) Vapor Pressure (Pa at 25°C or as indicated): 2.59 . 10–5 (45°C, Herbicide Handbook 1989) 4.00 . 10–5 (Worthing & Hance 1991) 0.001 (Montgomery 1993; quoted, Majewski & Capel 1995) negligible (Tomlin 1994) 0.0 (selected, Halfon et al. 1996) Henry’s Law Constant (Pa m3/mol at 25°C): 1.41 . 10–5 (calculated-P/C, Montgomery 1993) Octanol/Water Partition Coefficient, log KOW: –1.70 (shake flask, pH 5.3, Martin & Edgington 1981) –4.10 (shake flask, pH 2.5, Stevens et al. 1988) –3.25 (Reinert 1989) –4.59 (Worthing & Hance 1991) –1.60 (Montgomery 1993) –4.10, –1.70 (pH 2.5, pH 5.3, quoted, Sangster 1993) –1.70 (pH 5.3, selected, Hansch et al. 1995) 0.94 (RP-HPLC-RT correlation, Finizio et al. 1997) P HN OH O HO O HO © 2006 by Taylor & Francis Group, LLC Herbicides 3573 Bioconcentration Factor, log BCF: 0.477 (calculated-S, Kenaga 1980; quoted, Isensee 1991) 2.26 (calculated-KOC, Kenaga 1980) Sorption Partition Coefficient, log KOC: 3.42 (soil, Sprankle et al. 1975; Hance 1976; Nomura & Hilton 1977) 1.40 (soil, calculated-S as per Kenaga & Goring 1980, Kenaga 1980) 1.22 (selected, USDA 1989; quoted, Neary et al. 1993) –0.43 (Reinert 1989) 3.69, 3.53, 3.42 (3 agricultural soils: Houston clay loam at pH 7.5, Muskingum silt loam at pH 5.8, Sassafras sandy loam at pH 5.6, Reinert 1989) 4.38 (organic carbon, Wauchope et al. 1991) 3.43–3.69 (Montgomery 1993) Environmental Fate Rate Constants, k, or Half-Lives, t.: Volatilization: Photolysis: t. = 48 h for 0% of 168 µg/mL to degrade in distilled water under > 290 nm light (Rueppel et al. 1977; quoted, Cessna & Muir 1991); t. = 9 wk for > 90% of 2 µg/mL to degrade in distilled water under sunlight (Lund-HOie & Friestad 1986; quoted, Cessna & Muir 1991); t. = 4.0 d and 3–4 wk for aqueous solutions of 1.0 and 2000 ppm under indoor UV light (Lund-HOie & Friestad 1986; quoted, Montgomery 1993). Oxidation: k(aq.) = 7.3 . 108 M–1 s–1 for the reaction (photo-Fenton with reference to glycolic acid) with hydroxyl radical in aqueous solutions at pH 3.8 and at 24 ± 1°C (Buxton et al. 1988; quoted, Faust & Hoigne 1990; Haag & Yao 1992) k(aq.) = (0.027–8.2) . 103 M–1 s–1 for direct reaction with ozone in water at pH 1.8–7.0 and 22 ± 2°C, with a half-life of 4.0 s at pH 7 (Yao & Haag 1991). k(aq.) = (1.8 ± 0.5) . 108 M–1 s–1 for the reaction (photo-Fenton with reference to glycolic acid) with hydroxyl radical in aqueous solutions at pH 3.8 and at 24 ± 1°C (Haag & Yao 1992). Hydrolysis: t. = 7 d for 10 µg/mL to hydrolyze in sterile water + soil (Rueppel et al. 1977; quoted, Muir 1991); t. = 32 d for 25 and 250 µg/mL to hydrolyze in sterile distilled water at pH 3, 6 and 9 in the dark at 5 and 35°C (Ghassemi et al. 1981; quoted, Muir 1991) Biodegradation: t. < 28 d for 10 µg/mL to biodegrade in soil-water suspension (Rueppel et al. 1977; quoted, Muir 1991); t. > 9 wk for 2 µg/mL to biodegrade in polluted lake water (Rueppel et al. 1977; quoted, Muir 1991); rate constant k = 0.1 d–1 from soil incubation die-away studies (Rao & Davidson 1980; quoted, Scow 1982); t. = 70 d in pond water at pH 7.2, t. = 63 d in swamp water at pH 6.3 and t. = 49 d in Sphagnum bog water at pH 4.2 (Ghassemi et al. 1981; quoted, Muir 1991). Biotransformation: Bioconcentration, Uptake (k1) and Elimination (k2) Rate Constants: Half-Lives in the Environment: Air: Surface water: t. > 9 wk for 2 µg/mL to biodegrade in polluted lake water (Rueppel et al. 1977; quoted, Muir 1991); t. = 70 d in pond water at pH 7.2, t. = 63 d in swamp water at pH 6.3 and t. = 49 d in Sphagnum bog water at pH 4.2 (Ghossemi et al. 1981; quoted, Muir 1991); measured rate constant k = (0.027 - 8.2) . 103 M–1 s–1 for direct reaction with ozone in water at pH 1.8–7.0 and 22 ± 2°C, with t. = 4.0 s at pH 7 (Yao & Haag 1991). Ground water: Sediment: © 2006 by Taylor & Francis Group, LLC 3574 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals Soil: t. < 28 d for 10 µg/mL to biodegrade in soil-water suspension (Rueppel et al. 1977; quoted, Muir 1991); estimated first-order t. = 7 d from biodegradation rate constant k = 0.1 d–1 from soil incubation die-away studies (Rao & davidson 1980; quoted, Scow 1982); moderately persistent in soil with t. = 20–100 d (Willis & McDowell 1982); average t. < 60 d (Hartley & Kidd 1987; Herbicide Handbook 1989; quoted, Montgomery 1993); selected t. = 47 d (Wauchope et al. 1991; quoted, Dowd et al. 1993; Halfon et al. 1996). Biota: average t. = 60 d in the forest (USDA 1989; quoted, Neary et al. 1993). © 2006 by Taylor & Francis Group, LLC Herbicides 3575 17.1.1.43 Isopropalin Common Name: Isopropalin Synonym: EL 179, Isopropaline, Isopropalin solution, Paarlan Chemical Name: 4-isopropyl-2,6-dinitro-N,N-dipropylaniline; 4-(1-methylethyl)-2,6-dinitro-N,N-dipropylbenzenamine; 2,6-dinitro-N,N-dipropylcumidine Uses: herbicide used pre-planting and incorporated with soil preparation to control broadleaf weeds and grasses in transplanted tobacco, and in direct-seeded tomatoes and capsicums. CAS Registry No: 33820-53-0 Molecular Formula: C15H23N3O4 Molecular Weight: 309.362 Melting Point (°C): liquid Boiling Point (°C): Density (g/cm3 at 20°C): Molar Volume (cm3/mol): 361.3 (calculated-Le Bas method at normal boiling point) Dissociation Constant pKa: Enthalpy of Fusion, .Hfus (kJ/mol): Entropy of Fusion, .Sfus (J/mol K): Fugacity Ratio at 25°C (assuming .Sfus = 56 J/mol K), F: 1.0 Water Solubility (g/m3 or mg/L at 25°C or as indicated): 0.11 (Martin & Worthing 1977; Herbicide Handbook 1978) 1.10 (Ashton & Crafts 1981) 0.10 (Spencer 1982; Hartley & Kidd 1987; Budavari 1989; Milne 1955) 0.10 (Worthing & Walker 1987, Worthing & Hance 1991) 0.08 (Herbicide Handbook 1989) 0.10 (20–25°C, selected, Wauchope et al. 1992; Hornsby et al. 1996) 0.02 (predicted-AQUAFAC, Lee et al. 1996) Vapor Pressure (Pa at 25°C or as indicated): 0.0019 (30°C, Ashton & Crafts 1981) 0.0019 (30°C, Hartley & Kidd 1987) 0.0040 (25.6°C, Herbicide Handbook 1989) 0.0012 (20–25°C, selected, Wauchope et al. 1992; Hornsby et al. 1996) Henry’s Law Constant (Pa·m3/mol at 25°C): 5.34 (calculated-P/C, this work) Octanol/Water Partition Coefficient, log KOW: Bioconcentration Factor, log BCF: 3.50 (calculated-S, Kenaga 1980; quoted, Isensee 1991) 3.88 (calculated-KOC, Kenaga 1980) Sorption Partition Coefficient, log KOC: 4.88 (soil, Harvey 1974) 4.17 (soil, calculated-S as per Kenaga & Goring 1980, Kenaga 1980) 4.17–4.88 (soil, quoted values, Bottoni & Funari 1992) N NO2 O2N © 2006 by Taylor & Francis Group, LLC 3576 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals 4.00 (20–25°C, selected, Wauchope et al. 1992; Hornsby et al. 1996) 4.00 (selected, Lohninger 1994) 3.50 (soil, estimated-general model using molecular descriptors, Gramatica et al. 2000) Environmental Fate Rate Constants, k, or Half-Lives, t.: Volatilization: Photolysis: atmosphere photolysis t. = 288–864 h, based on observed photolysis on soil TLC plates under summer sunlight (Helling 1976; quoted, Howard et al. 1991) and adjusted for relative winter sunlight intensity (Lyman et al. 1982; quoted, Howard et al. 1991); aqueous photolysis t. = 288–864 h, based on observed photolysis on soil TLC plates under summer sunlight (Helling 1976; quoted, Howard et al. 1991) and adjusted for relative winter sunlight intensity (Lyman et al. 1982; quoted, Howard et al. 1991). Oxidation: photooxidation t. = 0.743–74.3 h in air, based on estimated rate constant for the vapor-phase reaction with hydroxyl radicals in air (Atkinson 1987; quoted, Howard et al. 1991). Hydrolysis: Abiotic Transformation: Degradation by abiotic reductive transformations: k = 1.71 M–1 s–1 in H2S with (mecapto)juglone (hydroquinone moiety, an abiotic reductant found in natural systems) solution at pH 6.65 (Wang & Arnold 2003) Aqueous solutions with surface-bound Fe(II) species and their furst-order rate constants as: k = 0.94 . 10–3 h–1 at pH 6.5, k = 0.36 . 10–2 h–1 at pH 7.0, k = 0.057 h–1 at pH 7.4, and k = 1.76 h–1 at pH 7.8 for aqueous ferrous ion system; k = 0.297 h–1 at pH 6.5, k = 0.586 h–1 at pH 6.7, k = 1.28 h–1 at pH 7.0, and k = 6.90 h–1 at pH 7.3 for Fe(II)/goethite system; k = 9.91 . 10–3 h–1 at pH 6.5, k = 8.45 . 10–3 h–1 at pH 7.0, k = 7.45 . 10–3 h–1 at pH 7.4 and k = 6.96 . 10–2 h–1 at pH 7.8 for Fe(II)/clay system, all with total dissolved Fe(II) = 1 mM (Wang & Arnold 2003) Biodegradation: t.(aq. aerobic) = 408–2520 h, based on aerobic soil die-away test data for one soil at 15°C and 30°C (Gingerich & Zimdahl 1976; quoted, Howard et al. 1991) t.(aq. anaerobic) = 96–360 h, based on anaerobic soil die-away test that tested one soil (Gingerich & Zimdahl 1976; quoted, Howard et al. 1991) Biotransformation: Bioconcentration, Uptake (k1) and Elimination (k2) Rate Constants: Half-Lives in the Environment: Air: t. = 0.743–74.3 h, based on estimated rate constant for the vapor-phase reaction with hydroxyl radicals in air (Atkinson 1987; quoted, Howard et al. 1991). Surface water: t. = 288–864 h, based on observed photolysis on soil TLC plates under summer sunlight (Helling 1976; quoted, Howard et al. 1991) and adjusted for relative winter sunlight intensity (Lyman et al. 1982; quoted, Howard et al. 1991). Ground water: t. = 96–5040 h, based on estimated unacclimated aqueous aerobic and anaerobic degradation half-lives (Howard et al. 1991) reported t. < 180 d (Bottoni & Funari 1992) Sediment: Soil: t. = 408–2520 h, based on aerobic soil die-away test data for one soil at 15°C and 30°C (Gingerich & Zimdahl 1976; quoted, Howard et al. 1991); selected field t. = 100 d (Wauchope et al. 1992; Hornsby et al. 1996); t. < 180 d (Bottoni & Funari 1992). Biota: © 2006 by Taylor & Francis Group, LLC Herbicides 3577 17.1.1.44 Isoproturon Common Name: Isoproturon Synonym: Alon, Arelon, CGA 18731, Gramion, Graminon, Hoe 16410, Hytane, IP 50, IP flo, Tolkan Chemical Name: 3-(4-isopropylphenyl)-1,1-dimethylurea; 3-p-cumenyl-l-1-dimethylurea Uses: herbicide used for pre- and post-emergence control of annual grasses and broadleaf weeds in spring and winter wheat (except durum wheat), spring and winter barley, winter rye, and triticale. CAS Registry No: 34123-59-6 Molecular Formula: C12H18N2O Molecular Weight: 206.284 Melting Point (°C): 155–156 (Worthing & Hance1991) 158 (Tomlin 1994) Boiling Point (°C): Density (g/cm3 at 20°C): 1.16 (Hartley & Kidd 1987; Tomlin 1994) Molar Volume (cm3/mol): 259.1 (calculated-Le Bas method at normal boiling point) Dissociation Constant pKa: Enthalpy of Fusion, .Hfus (kJ/mol): Entropy of Fusion, .Sfus (J/mol K): Fugacity Ratio at 25°C (assuming .Sfus = 56 J/mol K), F: Water Solubility (g/m3 or mg/L at 25°C or as indicated): 60 (Martin & Worthing 1977) 70 (20°C, Spencer 1982) 72 (20°C, Hartley & Kidd 1987) 55 (Worthing & Walker 1987, Worthing & Hance 1991) 55.9 (Chaumat et al. 1991) 65 (22°C, Tomlin 1994; quoted, Otto et al. 1997) 65 (20°C, selected, Traub-Eberhard et al. 1994) Vapor Pressure (Pa at 25°C or as indicated): 3.3 . 10–6 (20°C, Spencer 1982; Hartley & Kidd 1987) 3.3 . 10–6 (20°C, Worthing & Hance 1991) 3.3 . 10–6, 3.15 . 10–2, 0.172 (20, 77, 150°C, Tomlin 1994) Henry’s Law Constant (Pa·m3/mol at 25°C): 1.05 . 10–5 (calculated-P/C, Otto et al. 1997) 1.24 . 10–5 (calculated-P/C, this work) Octanol/Water Partition Coefficient, log KOW at 25°C or as indicated: 2.87 (shake flask, Log P Database, Hansch & Leo 1987) 2.25 (Worthing & Hance 1991) 2.30 (shake flask, pH 7, Baker et al. 1992) 2.537 (calculated, Evelyne et al. 1992) 2.30 (Behrendt & Bruggemann 1993) 2.87 (recommended, Sangster 1993) 2.87 (recommended, Hansch et al. 1995) HN N O © 2006 by Taylor & Francis Group, LLC 3578 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals 2.50 (pH 7, 22°C, Tomlin 1994) 2.40 (quoted Pomona-database, Muller & Kordel 1996) Bioconcentration Factor, log BCF: 1.79 (calculated-S, Kenaga 1980) 1.76, 1.82 (cuticle/water: tomato, pepper; Chaumat et al. 1991) 1.71, 1.90 (cuticle/water: box tree, pear; Chaumat et al. 1991) 1.52, 1.20 (cuticle/water: ivy, vanilla; Chaumat et al. 1991) 1.76, 1.82 (cuticle/water: tomato, pepper; Evelyne et al. 1992) Sorption Partition Coefficient, log KOC: 2.66 (soil, calculated-S, Kenaga 1980) 1.86 (soil, HPLC-screening method, mean value of different stationary and mobile phases, Kordel et al. 1993) 2.11 (soil, quoted from Kordel et al. 1993, Traub-Eberhard et al. 1994) 1.86; 2.40 (HPLC-screening method; calculated-PCKOC fragment method, Muller & Kordel 1996) 2.57, 1.71, 1.78, 1.73, 2.34 (first generation Eurosoils ES-1, ES-2, ES-3, ES-4, ES-5, shake flask/batch equilibrium- HPLC/UV, Gawlik et al. 1998, 1999) 1.86, 2.31; 2.81, 2.24, 2.83, 2.35, 1.93 (quoted lit., calculated-KOW; HPLC-screening method with different LCcolumns, Szabo et al. 1999) 2.155, 1.918, 1.790, 1.719, 2.367 (second generation Eurosoils ES-1, ES-2, ES-3, ES-4, ES-5, shake flask/batch equilibrium-HPLC/UV and HPLC-k. correlation, Gawlik et al. 1999) 2.155, 1.918, 1.790, 1.719, 2.367 (second generation Eurosoils ES-1, ES-2, ES-3, ES-4, ES-5, shake flask/batch equilibrium-HPLC/UV and HPLC-k. correlation, Gawlik et al. 2000) 1.78, 2.10 (Kishon river sediments, sorption isotherm, Chefetz et al. 2004) Environmental Fate Rate Constants, k, or Half-Lives, t.: Volatilization: Photolysis: atmosphere photolysis t. = 288–864 h, based on observed photolysis on soil TLC plates under summer sunlight (Helling 1976; quoted, Howard et al. 1991) and adjusted for relative winter sunlight intensity (Lyman et al. 1982; quoted, Howard et al. 1991); aqueous photolysis t. = 288–864 h, based on observed photolysis on soil TLC plates under summer sunlight (Helling 1976; quoted, Howard et al. 1991) and adjusted for relative winter sunlight intensity (Lyman et al. 1982; quoted, Howard et al. 1991); t. = 1.5 h for 215 µg/mL to degrade in distilled water under 254 nm light (Kulshrestha & Mukerjee 1986; quoted, Cessna & Muir 1991). Oxidation: photooxidation t. = 0.743–74.3 h in air, based on estimated rate constant for the vapor-phase reaction with hydroxyl radicals in air (Atkinson 1987; quoted, Howard et al. 1991). Hydrolysis: Biodegradation: aqueous aerobic t. = 408–2520 h, based on aerobic soil die-away test data for one soil at 15°C and 30°C (Gingerich & Zimdahl 1976; quoted, Howard et al. 1991); aqueous anaerobic t. = 96–360 h, based on anaerobic soil die-away test which tested one soil (Gingerich & Zimdahl 1976; quoted, Howard et al. 1991) Biotransformation: ~ 11% of a selection of 90 strains of micromycetes mostly isolated from soil-soil fungi, depleted over 50% of isoproturon (100 mg/L) in 5-d experiment (Vroumsia et al. 1996) Bioconcentration, Uptake (k1) and Elimination (k2) Rate Constants: Half-Lives in the Environment: Air: t. = 0.743–74.3 h, based on estimated rate constant for the vapor-phase reaction with hydroxyl radicals in air (Atkinson 1987; quoted, Howard et al. 1991). Surface water: t. = 288–864 h, based on observed photolysis on soil TLC plates under summer sunlight (Helling 1976; quoted, Howard et al. 1991) and adjusted for relative winter sunlight intensity (Lyman et al. 1982; quoted, Howard et al. 1991). Groundwater: t. = 96–5040 h, based on estimated unacclimated aqueous aerobic and anaerobic degradation halflives (Howard et al. 1991) reported half-lives or persistence, t. = 12–29 and 60–120 d (Bottoni & Funari 1992) © 2006 by Taylor & Francis Group, LLC Herbicides 3579 Sediment: Soil: t. = 408–2520 h, based on aerobic soil die-away test data for one soil at 15°C and 30°C (Gingerich & Zimdahl 1976; quoted, Howard et al. 1991); reported t. = 12–29 d and 60–120 d (Bottoni & Funari 1992); t. = 15–21 d in sandy loam, t. = 11 d in silt loam at 20°C (Traub-Eberhard et al. 1994) Degradation and mineralization t. = 16 d, 24 d and 34 d for pelosol, brown calcareous soil and brown acid soil, respectively, over 120 days under controlled laboratory conditions (Pieuchot et al. 1996) estimated t. ~ 14.6 d under conventional tillage, t. = 7.99 d under ridge tillage and t. = 12.17 d with no tillage (Otto et al. 1997). © 2006 by Taylor & Francis Group, LLC 3580 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals 17.1.1.45 Linuron Common Name: Linuron Synonym: Afalon, Cephalon, Garnitan, Herbicide 326, Hoe 2810, Linex 4L, Linorox, Linurex, Lorox, Methoxydiuron, Premalin, Scarclex, Sinuron Chemical Name: 3-(3,4-dichlorophenyl)-1-methoxy-1-methylurea; N.-(3,4-dichlorophenyl)-N-methoxy-N-methylurea Uses: selective pre-emergence and post-emergence herbicide used on a wide variety of food crops to control many annual broadleaf and grass weeds. CAS Registry No: 330-55-2 Molecular Formula: C9H10Cl2N2O2 Molecular Weight: 249.093 Melting Point (°C): 93 (Lide 2003) Boiling Point (°C): Density (g/cm3 at 20°C): Molar Volume (cm3/mol): 232.9 (calculated-Le Bas method at normal boiling point) Dissociation Constant pKa: Enthalpy of Vaporization, .HV (kJ/mol): 90.23 (Rordorf 1989) Enthalpy of Fusion, .Hfus (kJ/mol): 28.66 (DSC method, Plato & Glasgow 1969) 25.9 (Rordorf 1989) Entropy of Fusion, .Sfus (J/mol K): Fugacity Ratio at 25°C (assuming .Sfus = 56 J/mol K), F: 0.215 (mp at 93°C) Water Solubility (g/m3 or mg/L at 25°C or as indicated): 75 (Woodford & Evans 1963; Bailey & White 1965; Hartley & Graham-Bryce 1980; Kenaga 1980; Kenaga & Goring 1980; Beste & Humburg 1983) 75 (Melnikov 1971; Spencer 1973, 1982; Wauchope 1978; Khan 1980; Weber et al. 1980; Ashton & Crafts 1981; Briggs 1981) 75 (Martin & Worthing 1977; Worthing & Walker 1983, 1987; Herbicide Handbook 1978,1989) 81 (Hartley & Kidd 1987; Milne 1995) 81 (24°C, Worthing & Hance 1991) 75 (20–25°C, selected, Wauchope et al. 1992; Hornsby et al. 1996) 75–81 (Montgomery 1993) Vapor Pressure (Pa at 25°C or as indicated and reported temperature dependence equations): 0.00147 (20°C, Quellette & King 1977) 0.0012 (20°C, Hartley & Graham-Bryce 1980) 0.002 (24°C, Khan 1980) 0.002 (20–25°C, Weber et al. 1980) 0.002 (24°C, Hartley & Kidd 1987; Worthing & Hance 1991; Montgomery 1993) 0.0014 (20°C, selected, Suntio et al. 1988) 3.50 . 10–4, 1.10 . 10–2, 0.22, 2.90, 28.0 (25, 50, 70, 100, 125°C, gas saturation-GC, Rordorf 1989) log (PS/Pa) = 16.074 – 5824.2/(T/K); measured range 40.5–92 7°C (solid, gas saturation-GC, Rordorf 1989) log (PL/Pa) = 12.989 – 4713.7/(T/K); measured range 92.7–160°C (liquid, gas saturation-GC, Rordorf 1989) 0.0011 (20°C, selected, Taylor & Spencer 1990) 0.0023 (20–25°C, selected, Wauchope et al. 1992; Hornsby et al. 1996) HN N O O Cl Cl © 2006 by Taylor & Francis Group, LLC Herbicides 3581 0.0027 (selected, Halfon et al. 1996) Henry’s Law Constant (Pa·m3/mol at 25°C or as indicated): 0.0054 (20°C, calculated-P/C, Suntio et al. 1988) 0.004 (Taylor & Glotfelty 1988) 0.0062 (20–25°C, calculated-P/C, Montgomery 1993) 0.00465 (calculated-P/C, this work) Octanol/Water Partition Coefficient, log KOW: 2.19 (Briggs 1969) 3.20 (shake flask-UV, Erkell & Walum 1979) 2.76 (shake flask-UV, Briggs 1981) 3.11 (shake flask, Mitsutake et al. 1986) 2.48 (selected, Gerstl & Helling 1987) 3.00 (Worthing & Hance 1991; Milne 1995) 2.19, 3.00 (Montgomery 1993) 2.75 (RP-HPLC-RT correlation, Sicbaldi & Finizio 1993) 3.20 (recommended, Sangster 1993) 3.20 (recommended, Hansch et al. 1995) 3.18 (Pomona-database, Muller & Kordel 1996) 2.75 (RP-HPLC-RT correlation, Finizio et al. 1997) 2.72 (RP-HPLC-RT correlation, Yu et al. 1997) Bioconcentration Factor, log BCF: 1.73 (calculated-S, Kenaga 1980; quoted, Isensee 1991) 1.68 (calculated-KOC, Kenaga 1980) 1.73 (calculated, Pait et al. 1992) Sorption Partition Coefficient, log KOC: 2.91 (soil, Hamaker & Thompson 1972) 2.61 (soil, calculated-S as per Kenaga & Goring 1980, Kenaga 1980) 2.93 (average soils/sediments, Rao & Davidson 1980) 2.43 (soil, converted form reported KOM multiplied by 1.724, Briggs 1981) 2.93, 2.80, 1.80 (estimated-S, calculated-S and mp, calculated-KOW, Karickhoff 1981) 3.83 (Means & Wijayaratne 1982) 2.99, 2.58; 2.62, 2.80 (estimated-KOW, S, Madhun et al. 1986) 2.76, 2.64 (quoted, calculated-MCI ., Gerstl & Helling 1987) 2.94 (screening model calculations, Jury et al. 1987b) 2.61–2.91, 2.83, 2.93 (soil, quoted values, Bottoni & Funari 1992) 2.60 (soil, 20–25°C, selected, Wauchope et al. 1992;) 2.70–2.78 (Montgomery 1993) 2.59 (soil, HPLC-screening method, mean value from different stationary and mobile phases, Kordel et al. 1993, 1995a) 2.59 (soil, HPLC-screening method, Kordel et al. 1993, 1995b) 2.70 (soil, calculated-MCI 1., Sabljic et al. 1995) 2.59; 2.54 (HPLC-screening method; calculated-PCKOC fragment method, Muller & Kordel 1996) 3.28, 2.39, 2.46, 2.29, 3.12 (first generation Eurosoils ES-1, ES2, ES-3, ES-4, ES-5, shake flask/batch equilibrium- HPLC/UV, Gawlik et al. 1998, 1999) 2.884, 2.58, 2.45, 1.33, 3.18 (second generation Eurosoils ES-1, ES2, ES-3, ES-4, ES-5, shake flask/batch equilibrium-HPLC/UV, Gawlik et al. 1999) 2.884, 2.578, 2.450, 2.336, 3.183 (second generation Eurosoils ES-1, ES-2, ES-3, ES-4, ES-5, shake flask/batch equilibrium-HPLC/UV and HPLC-k. correlation, Gawlik et al. 2000) 2.70; 2.55, 2.61 (soil, quoted obs.; estimated-class-specific model, estimated-general model using molecular descriptors, Gramatica et al. 2000) 2.65, 2.64 (soils: organic carbon OC . 0.1%, OC . 0.5%, average, Delle Site 2001) © 2006 by Taylor & Francis Group, LLC 3582 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals 2.78 (average values for sediment OC. 0.5%, Delle Site 2001) Environmental Fate Rate Constants, k, or Half-Lives, t.: Volatilization: Photolysis: t. = 2 months for 31% of 55 µg mL–1 to degrade in distilled water under sunlight (Rosen et al. 1969; quoted, Cessna & Muir 1991); t. = 2.25 h for 67–75% of 75 µg mL–1 to degrade in distilled water under 300 nm light (Tanaka et al. 1981; quoted, Cessna & Muir 1991); atmosphere photolysis t. = 1344–4032 h, based on measured rate constant for summer sunlight photolysis in distilled water (Rosen et al. 1969; quoted, Howard et al. 1991) and adjusted to relative winter sunlight intensity (Lyman et al. 1982; quoted, Howard et al. 1991); aqueous photolysis t. = 1344–4032 h, based on measured rate constant for summer sunlight photolysis in distilled water (Rosen et al. 1969; quoted, Howard et al. 1991) and adjusted to relative winter sunlight intensity (Lyman et al. 1982; quoted, Howard et al. 1991). Oxidation: photooxidation t. = 0.49–4.90 h in air, based on an estimated rate constant for the vapor-phase reaction with hydroxyl radicals in air (Atkinson 1987; quoted, Howard et al. 1991). Hydrolysis: t. > 4 months for 4980 µg mL–1 to hydrolyze in phosphate buffer at pH 5–9 and 20°C (El-dib & Aly 1976; quoted, Muir 1991). Biodegradation: t. = 78 d in soil (Moyer et al. 1972; quoted, Means et al. 1983), t. = 87 d in soil (Hance 1974; quoted, Means et al. 1983), t. = 58 and 180 d in soil (Urosol & Hance 1974; quoted, Means et al. 1983); aqueous aerobic t. = 672–4272 h, based on soil die-away test data (Walker 1978; Walker & Zimdahl 1981; quoted, Howard et al. 1991); rate constant k = 0.0096 d–1 by soil incubation die-away studies (Rao & Davidson 1980; quoted, Scow 1982); aerobic t. . 40 d for 1 µg mL–1 to biodegrade in lake sediment and t. . 60 d for 4 µg mL–1 to biodegrade in lake sediment and water (Huber & Gemes 1981; quoted, Muir 1991); aerobic t. . 20 d for 0.22 µg mL–1 to biodegrade in pond sediment plus aerobic salts medium of 34 g L–1 (Stepp et al. 1985; quoted, Muir 1991); aqueous anaerobic t. = 2688–17088 h, based on estimated unacclimated aqueous aerobic biodegradation half-life (Howard et al. 1991) degradation rate constant k = (3.48 ± 0.156) . 10–2 d–1 with t. = 19.9 d in control soil and k = (23.2 ± 2.07) . 10–2 d–1 with t. = 2.99 d in pretreated soil in the field; k = (3.73 ± 0.208) . 10–2 d–1 with t. = 18.6 d in control soil and k = (18.8 ± 2.76) . 10–2 d–1 with t. = 3.68 d in pretreated soil once only in the laboratory (Walker & Welch 1991) Biotransformation: Bioconcentration, Uptake (k1) and Elimination (k2) Rate Constants: Half-Lives in the Environment: Air: t. = 0.49–4.90 h, based on an estimated rate constant for the vapor-phase reaction with hydroxyl radicals in air (Atkinson 1987; quoted, Howard et al. 1991). Surface water: t. = 672–4272 h, based on estimated unacclimated aqueous aerobic biodegradation half-life (Howard et al. 1991). Ground water: t. = 1344–8544 h, based on estimated unacclimated aqueous aerobic biodegradation half-life (Howard et al. 1991) reported half-lives or persistence, t. = 38–69 and 75 d (Bottoni & Funari 1992). Sediment: degradation t. = 12 d in estuarine sediment (12o/.) system (Cunningham et al. 1981; quoted, Means et al. 1983); degradation t. = 6 d in estuarine sediment (18o/.) system (Means et al. 1983). Soil: estimated persistence of 4 months (Kearney et al. 1969; Edwards 1973; quoted, Morrill et al. 1982; Jury et al. 1987a); t. = 672–4272 h, based on soil die-away test data (Walker 1978; Walker & Zimdahl 1981; quoted, Howard et al. 1991); persistence of 4 months (Wauchope 1978); © 2006 by Taylor & Francis Group, LLC Herbicides 3583 correlated t. = 57 d at pH 5.1–5.8, t. = 22 d at pH 6.3–7.0 and t. = 19 d at pH 7.7–8.2 (Boddington Barn soil, Hance 1979) and t. = 67 d at pH 4.6–5.2, t. = 53 d at pH 5.3–6.1, and t. ~ 20 d at pH 6.3–8.0 (Triangle soil, Hance 1979); estimated first-order t. = 72 d from biodegradation rate constant k = 0.0096 d–1 by soil incubation die-away studies (Rao & Davidson 1980; quoted, Scow 1982); decomposition t. = 11 d in fresh soil and t. = 12 d in air dried soil both in polyethylene bags, t. = 49 d in undisturbed cores and t. = 40 d in perfusion (Hance & Haynes 1981); moderately persistent in soil with t. = 20–100 d (Willis & McDowell 1982); t. = 2 to 5 months under field conditions (Hartley & Kidd 1987; Herbicide Handbook 1989; quoted, Montgomery 1993); t. = 75 d from screening model calculations (Jury 1987b); t. = 60, 35, 35, 30 d in plots treated, i.e., repeated application of pesticide, for the first, second, third and fourth time, respectively, in the field; in the laboratory t. reduced from 19 d to 3–7 d in a single pretreatment in moist oil at 20°C (Walker & Welch 1991) reported t. = 38–69 d and 75 d (Bottoni & Funari 1992); selected field t. = 60 d (Wauchope et al. 1992; quoted, Richards & Baker 1993; quoted, Halfon et al. 1996; Hornsby et al. 1996); soil t. = 60 d (Pait et al. 1992); soil t. = 29–67 d (Di Guardo et al. 1994). Biota: biochemical t. = 75 d from screening model calculations (Jury et al. 1987b). © 2006 by Taylor & Francis Group, LLC 3584 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals 17.1.1.46 MCPA Common Name: MCPA Synonym: Agritox, Agroxohe, Agroxone, Anicon Kombi, Bordermaster, Chiptox, Chwastox, Cornox, Ded-weed, Dicopur-M, Dicotex, Dikotes, Emcepan, Empal, Hedapur M 52, Hederax M, Herbicide M, Hedonal, Hormotuho, Kilsem, Krezone, Legumex DB, Leuna M, Leyspray, Linormone, MCP, metaxon, Methoxone, Netazol, Okultin M, Phenoxylene Plus, Raphone, Razol dock killer, Rhomenc, Rhonox, Shamrox, Seppic MMD, Trasan, Ustinex, Vacate, Verdone, Weedar, Weed-rhap, Zelan Chemical Name: (4-chloro-2-methylphenoxy)acetic acid; 4-chloro-o-tolyloxyacetic acid Uses: systemic post-emergence herbicide to control annual and perennial weeds in cereals, rice, flax, vines, peas, potatoes, asparagus, grassland and turf. CAS Registry No: 94-74-6 Molecular Formula: C9H9ClO3 Molecular Weight: 200.618 Melting Point (°C): 120 (Montgomery 1993; Milne 1995; Lide 2003) Boiling Point (°C): Density (g/cm3 at 20°C): 1.56 (25°C, Que Hee et al. 1981; Herbicide Handbook 1989; Montgomery 1993) Molar Volume (cm3/mol): 211.1 (calculated-Le Bas method at normal boiling point) Dissociation Constant pKa: 3.05 (potentiometric titration, Nelson & Faust 1969) 3.125 (Cessna & Grover 1978) 3.07 (Worthing & Hance 1991) 3.05–3.13 (Montgomery 1993) 3.12 (Hornsby et al. 1996) Enthalpy of Fusion, .Hfus (kJ/mol): Entropy of Fusion, .Sfus (J/mol K): Fugacity Ratio at 25°C (assuming .Sfus = 56 J/mol K), F: 0.117 (mp at 120°C) Water Solubility (g/m3 or mg/L at 25°C or as indicated): 1605 (shake flask-UV, Leopold et al. 1960) 1605 (Bailey & White 1965) < 1000 (Khan 1980) 630 (20°C, Melnikov 1971) 825 (Martin & Worthing 1977; Weber et al. 1980; Milne 1995) 1500 (selected, Seiber et al. 1986) 825 (room temp., Hartley & Kidd 1987; Worthing & Hance 1991) 817 (selected, Gerstl & Helling 1987) 835 (room temp., Worthing & Walker 1987) 730–825 (Montgomery 1993) Vapor Pressure (Pa at 25°C or as indicated): 7.9 . 10–4 (measured-volatilization rate, Seiber et al. 1986) 2.0 . 10–4 (20°C, Hartley & Kidd 1987) 2.0 . 10–4 (21°C, Worthing & Walker1987, 1991) 2.3 . 10–5 (20°C, Tomlin 1994) 2.0 . 10–4 (20°C, Milne 1995) 2.0 . 10–4 (selected, Halfon et al. 1996) Cl O OH O © 2006 by Taylor & Francis Group, LLC Herbicides 3585 Henry’s Law Constant (Pa·m3/mol at 25°C): 1.0 . 10–4 (calculated-P/C, Seiber et al. 1986) 4.86 . 10–4 (calculated-P/C as per Worthing & Walker 1987, Majewski & Capel 1995) < 0.010 (estimated, Mabury & Crosby 1996) 2.5 . 10–4 (calculated-P/C, this work) Octanol/Water Partition Coefficient, log KOW: 2.69 (selected, Dao et al. 1983) 2.30 (RP-HPLC-k. correlation, Braumann et al. 1983) –1.41 (selected, Gerstl & Helling 1987) –0.57 (shake flask-UV, pH 7, Stevens et al. 1988) 3.25 (countercurrent LC, Ilchmann et al. 1993) 1.37–1.43 (calculated, Montgomery 1993) –0.57, 3.25 (quoted, Sangster 1993) 2.68 (MedChem Master file or ClogP program, Sabljic et al. 1995) Bioconcentration Factor, log BCF: 1.15 (calculated-S, Kenaga 1980) Sorption Partition Coefficient, log KOC: 2.04 (soil, calculated-S, Kenaga 1980; quoted, Bottoni & Funari 1992) 1.95 (calculated-MCI ., Gerstl & Helling 1987) 2.03–2.07 (calculated, Montgomery 1993) 1.73 (calculated-QSAR MCI 1., Sabljic et al. 1995) 2.49; 1.58., 3.27, 3.17, 1.85, 2.19 (calculated-KOW; HPLC-screening method with different LC-columns, Szabo et al. 1999) Environmental Fate Rate Constants, k, or Half-Lives, t.: Volatilization: k = 9.78 . 10–7 h–1 at pH 3.5 (Seiber et al. 1986). Photolysis: t. = 71 h for < 10% of 50 µg mL–1 to degrade in NaOH solution at pH 9.8 under > 290 nm light (Soderquist & Crosby 1975; quoted, Cessna & Muir 1991); t. = 245 h for 17–98.5% of 9 µg mL–1 to degrade in distilled water under sunlight (Draper & Crosby 1984; quoted, Cessna & Muir 1991); t. = 4.6 d for 14,700 µg mL–1 to degrade in droplets of spray solution suspended in air under sunlight (Freiberg & Crosby 1986; quoted, Cessna & Muir 1991). Oxidation: degradation by ozone in dilute aqueous solutions (Benoit-Guyod et al. 1986) as follows:- t. = 9.4 min - dark with O3 in air; t. = 8.4 min - light with O3 in air, t. = 500 min - light, air only, at initial pH of 3.55; MCPA concn of 224 µM L–1, ozone input at 246 µM h–1; t. = 10.4 min - dark with O3 in air; t. = 9.0 min - light with O3 in air, at initial pH of 8.0, t. = 11.5 min - dark with O3 in air; t. = 11.3 min - light with O3 in air, at initial pH of 7.0, t. = 8.4 min - dark with O3 in air; t. = 9.4 min - light with O3 in air, at initial pH of 7.0, t. = 4.2 min - dark with O3 in air; t. = 4.2 min - light with O3 in air, t. = 150 min - light, air only, at initial pH of 8.0; MCPA concn of 5 µM L–1, ozone input at 246 µM h–1; t. = 176 min - dark with O3 in air; t. = 63 min - light with O3 in air, at initial pH of 8.0, MCPA concn of 224 µM L–1, ozone input at 4.6 µM h–1; t. = 300 min - dark with O3 in air; t. = 162 min - light with O3 in air, at initial pH of 8.0; MCPA concn of 224 µM L–1, ozone input at 0.2 µM h–1 (Benoit-Guyod et al. 1986). measured rate constant kOH(aq.) = 1.70 . 109 M–1 s–1 for reaction with hydroxyl radical, in irradiated field water both in the laboratory and sunlit rice paddies (Mabury & Crosby 1996). Hydrolysis: Biodegradation: t. > 168 h for 1 µg mL–1 to degrade in activated sludge (Schmidt 1975; quoted, Muir 1991); aerobic t. . 9 d for 1 µg mL–1 to degrade in natural water in absence of sunlight (Soderquist & Crosby 1975; quoted, Muir 1991); t. > 12 d for 0.045–0.156 µg mL–1 to degrade in water after application to model crop and washoff (Virtanen et al. 1979; quoted, Muir 1991); © 2006 by Taylor & Francis Group, LLC 3586 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals t. = 15–25 d for 10 µg mL–1 to degrade in flooded soils (Duah-Yentumi & Kuwatsuka 1980; quoted, Muir 1991); first order microbial degradation k = 0.01393 d–1 with t. = 50 d at room temp, k = 0.01687 d–1 with t. = 41 d at 35°C in sandy clay soil from Finland; k = 0.02999 d–1 with t. = 23 d at room temp, k = 0.03397 d–1 with t. = 20 d at 35°C in sandy loam soil from Bangladesh (Sattar & Paasivirta 1980) t. > 25 d for 10 µg mL–1 to degrade in flooded soils (Ursin 1985; quoted, Muir 1991). Biotransformation: Bioconcentration, Uptake (k1) and Elimination (k2) Rate Constants: Half-Lives in the Environment: Air: Surface water: dissipation t. . 4 d in rice field; t. = 17 d in dilute aqueous solution under laboratory irradiation (Soderquist & Crosby 1975); degradation t. = 4.2 - 300 min by ozone and light (UV > 300 nm) in dilute aqueous solution, depending on pH, concn of MCPA and ozone (shake flask-GC, Benoit-Guyod et al. 1986) degraded rapidly with t. = 9 d in rice paddy water held under darkened conditions (Muir 1991) field dissipation t. = 28.8 h in water (Mabury & Crosby 1996) Ground water: reported t. < 7 and t. = 20–25 d (Bottoni & Funari 1992) Sediment: t. = 80 to 400 d of MCPA at low concentrations in marine sediments (Muir 1991). Soil: degradation t. = 50 d at room temp., t. = 41 d at 35°C in Finland sandy clay soil; degradation t. = 23 d at room temp., t. = 20 d at 35°C in Bangladesh loam soil from first-order rate constant obtained by linear regression (Sattar & Paasivirta 1980); persistence of 3 months in soil (Edwards 1973; quoted, Morrill et al. 1982); t. = 25 d in flooded soils (Muir 1991); t. = 15 d (selected, Halfon et al. 1996). Biota: © 2006 by Taylor & Francis Group, LLC Herbicides 3587 17.1.1.47 MCPB Common Name: MCPB Synonym: Bexane, Can-Trol, Legumex, Thistrol, Thitrol, Trifolex, Tropotox Chemical Name: 4-(4-chloro-2-methylphenoxy)butanoic acid; 4-(4-chloro-2-methylphenoxy)-butyric acid Uses: herbicide for post-emergence control of annual and perennial broadleaf weeds in cereals, clovers, sainfoin, groundnuts, peas, etc. and also used to control broadleaf and woody weeds in forestry. CAS Registry No: 94-81-5 Molecular Formula: C11H13ClO3 Molecular Weight: 228.672 Melting Point (°C): 100 (Hartley & Kidd 1987; Worthing & Hance 1991; Tomlin 1994; Milne 1995; Lide 2003) Boiling Point (°C): > 280 (Tomlin 1994) Density (g/cm3 at 22°C): 1.254 (Tomlin 1994) Molar Volume (cm3/mol): 255.5 (calculated-Le Bas method at normal boiling point) Dissociation Constant pKa: 4.80 (potentiometric titration, Nelson & Faust 1969) 4.84 (Worthing & Hance 1991; Tomlin 1994) Enthalpy of Fusion, .Hfus (kJ/mol): 34.31 (DSC method, Plato 1972) Entropy of Fusion, .Sfus (J/mol K): Fugacity Ratio at 25°C (assuming .Sfus = 56 J/mol K), F: 0.184 (mp at 100°C) Water Solubility (g/m3 or mg/L at 25°C or as indicated): 41 (shake flask-UV, Leopold et al. 1960) 44 (rm. temp., Melnikov 1971) 44 (Bailey & White 1965; Martin & Worthing 1977; Hartley & Kidd 1987) 44 (rm. temp., Worthing & Walker 1987, Worthing & Hance 1991; Tomlin 1994; Milne 1995) Vapor Pressure (Pa at 25°C or as indicated): 5.77 . 10–5, 9.83 . 10–5 (20, 25°C, Tomlin 1994) Henry’s Law Constant (Pa·m3/mol at 25°C): 3.22 . 10–4 (calculated-P/C, this work) Octanol/Water Partition Coefficient, log KOW: 4.60 (selected, Dao et al. 1983) 3.53 (RP-HPLC-k. correlation, Braumann et al. 1983) 3.473 (countercurrent LC, Ilchmann et al. 1993) 2.79 (Tomlin 1994) 3.43 (selected, Hansch et al. 1995) Bioconcentration Factor, log BCF: 1.86 (calculated-S, Kenaga 1980) Sorption Partition Coefficient, log KOC: 2.73 (soil, calculated-S, Kenaga 1980) Cl O OH O © 2006 by Taylor & Francis Group, LLC 3588 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals Environmental Fate Rate Constants, k, or Half-Lives, t.: Half-Lives in the Environment: Soil: duration of residual activity in soil is ca. 3–4 months (Hartley & Kidd 1987; Tomlin 1994). © 2006 by Taylor & Francis Group, LLC Herbicides 3589 17.1.1.48 Mecoprop Common Name: Mecoprop Synonym: Compitox, Duplosan, Hedonal, Iso-Cornox, Kilprop, MCPP, Mecopex, Mepro, Methoxone, Propal Chemical Name: ( ± )-2-(4-chloro-2-methylphenoxy)propanoic acid; ( ± )-2-(4-chloro-o-tolyl-oxy)propionic acid Uses: herbicide for post-emergence control of broadleaf weeds in wheat, barley, rye, herbage seed crops, grassland, and under fruit trees and vines, etc. CAS Registry No: 7085-19-0 Molecular Formula: C10H11ClO3 Molecular Weight: 214.645 Melting Point (°C): 94–95 (Hartley & Kidd 1987; Herbicide Handbook 1989; Worthing & Hance 1991) Boiling Point (°C): Density (g/cm3 at 20°C): Molar Volume (cm3/mol): 233.3 (calculated-Le Bas method at normal boiling point) Dissociation Constant pKa: 3.75 (Bailey & White 1965; quoted, Que Hee et al. 1981) 3.105 (Cessna & Grover 1978) 3.78 (Worthing & Hance 1991) 3.11 (Armbrust 2000) Enthalpy of Fusion, .Hfus (kJ/mol): 28.87 (DSC method, Plato 1972) Entropy of Fusion, .Sfus (J/mol K): Fugacity Ratio at 25°C (assuming .Sfus = 56 J/mol K), F: Water Solubility (g/m3 or mg/L at 25°C or as indicated): 895 (Martin 1961; Bailey & White 1965) 891 (Bailey & White 1965) 620 (20°C, Melnikov 1971; Ashton & Crafts 1981; Herbicide Handbook 1989) 620 (Martin & Worthing 1977) 620 (20°C, Hartley & Kidd 1987; Worthing & Walker 1987, Worthing & Hance 1991) 734 (Tomlin 1994) Vapor Pressure (Pa at 25°C or as indicated): < 1.0 . 10–5 (20°C, Hartley & Kidd 1987) 3.10 . 10–4 (20°C, Worthing & Hance 1991) 0.0 (selected, Halfon et al. 1996) Henry’s Law Constant (Pa·m3/mol at 25°C): 7.43 . 10–5 (calculated-P/C, this work) 1.11 . 10–5 (quoted lit., Armbrust 2000) Octanol/Water Partition Coefficient, log KOW: 3.94 (selected, Dao et al. 1983) 2.83 (RP-HPLC-k. correlation, Braumann et al. 1983) 0.10 (Worthing & Hance 1991) 0.09; 3.126 (quoted; countercurrent LC, Ilchmann et al. 1993) 3.13 (recommended, Hansch et al. 1995) Cl O OH O © 2006 by Taylor & Francis Group, LLC 3590 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals Bioconcentration Factor, log BCF: 1.20 (calculated-S, Kenaga 1980) Sorption Partition Coefficient, log KOC: 2.11 (soil, calculated, Kenaga 1980, quoted, Bottoni & Funari 1992) 1.30 (selected, Lohninger 1994) 1.30 (quoted lit., Armburst 2000) Environmental Fate Rate Constants, k, or Half-Lives, t.: Volatilization: Photolysis: photodegradation t. < 10 -15 d on 3 Spanish natural dry soils; t. = 15–50 d on 10% peat-amened dry soils; degradation t. ~ 2–5.5 d on moist soils at field capacity and saturated soils for degradation at 0,1 and 2 exposures days; and t. = 13–32 d on moist soils at field capacity and saturated soils for degradation at 2,4 and 10 exposure days (Romero et al. 1998) Oxidation: photooxidation t. = 3.8–37.8 h in air, based on an estimated rate constant for the vapor-phase reaction with hydroxyl radicals in air (Atkinson 1987; quoted, Howard et al. 1991). Hydrolysis: stable aqueous hydrolysis rate at pH 5, 7, pH 9; measured hydroxy radical rate constant for mecoprop k = 9.0 . 1012 M–1 h–1 (Armbrust 2000) Biodegradation: aqueous aerobic t. = 168–240 h, based on aerobic soil grab sample data (Kirkland & Fryer 1972; Smith & Hayden 1981; quoted, Howard et al. 1991); aqueous anaerobic t. = 672–4320 h, based on anaerobic digest or sludge data (Battersby & Wilson 1989; quoted, Howard et al. 1991); aerobic rate constant, k = 2.89 . 10–3 h–1 (Armbrust 2000). Biotransformation: Bioconcentration, Uptake (k1) and Elimination (k2) Rate Constants: Half-Lives in the Environment: Air: t. = 3.8–37.8 h, based on an estimated rate constant for the vapor-phase reaction with hydroxyl radicals in air (Atkinson 1987; quoted, Howard et al. 1991). Surface water: t. = 168–240 h, based on estimated aqueous aerobic biodegradation half-life (Howard et al. 1991). Groundwater: t. = 336–4320 h, based on estimated aqueous aerobic and anaerobic biodegradation half-lives (Howard et al. 1991) reported t. = 8 d (Bottoni & Funari 1992). Sediment: Soil: t. = 168–240 h, based on aerobic soil grab sample data (Kirkland & Fryer 1972; Smith & Hayden 1981; quoted, Howard et al. 1991); reported t. = 8 d (Bottoni & Funari 1992); t. = 21 d (selected, Halfon et al. 1996) photodegradation t. < 10 -15 d on 3 Spanish natural dry soils; t. = 15–50 d on 10% peat-amened dry soils; degradation t. ~ 2–5.5 d on moist soils at field capacity and saturated soils for degradation at 0,1 and 2 exposures days; and t. = 13–32 d on moist soils at field capacity and saturated soils for degradation at 2,4 and 10 exposure days (Romero et al. 1998). Biota: © 2006 by Taylor & Francis Group, LLC Herbicides 3591 17.1.1.49 Metolachlor Common Name: Metolachlor Synonym: Bicep, CGA 24705, Codal, Cortoran multi, Dual, Metetilachlor, Milocep, Ontrack 8E, Pennant, Primagram, Primextra Chemical Name: 2-chloro-6.-ethyl-N-(2-methoxy-1-methylethyl)acet-o-toluidide; 2-chloro-N-(2-ethyl-6-methylphenyl)- N-(2-methoxy-1-methylethyl)acetamide Uses: pre-emergence herbicide to control most annual grasses and weeds in beans, chickpeas, corn, cotton, milo, okra, peanuts, peas, potatoes, sunflower, soybeans and some ornamentals. CAS Registry No: 51218-45-2 Molecular Formula: C15H22ClNO2 Molecular Weight: 283.795 Melting Point (°C): liquid Boiling Point (°C): 100 (at 0.001 mmHg, Herbicide Handbook 1989; Budavari 1989; Worthing & Hance 1991; Montgomery 1993; Milne 1995) Density (g/cm3 at 20°C): 1.12 (Hartley & Kidd 1987; Worthing & Hance 1991; Montgomery 1993; Milne 1995) 1.085 (Herbicide Handbook 1989) Molar Volume (cm3/mol): 340.0 (calculated-Le Bas method at normal boiling point) 258.0 (calculated-density) Dissociation Constant pKa: Enthalpy of Fusion, .Hfus (kJ/mol): Entropy of Fusion, .Sfus (J/mol K): Fugacity Ratio at 25°C (assuming .Sfus = 56 J/mol K), F: 1.0 Water Solubility (g/m3 or mg/L at 25°C or as indicated): 530 (Martin & Worthing 1977) 440 (selected, Ellgehausen et al. 1980) 520 (20°C, Ashton & Crafts 1981; Spencer 1982) 530 (shake flask-HPLC, Ellgehausen et al. 1981) 530 (20°C, Hartley & Kidd 1987; Herbicide Handbook 1989; Budavari 1989; Montgomery 1993) 530 (Hartley & Graham-Bryce 1980; Beste & Humburg 1983) 530 (20°C, Worthing & Walker 1987, Worthing & Hance 1991; Majewski & Capel 1995; Milne 1995) 488 (Tomlin 1994) 530 (20–25°C, selected, Hornsby et al. 1996) 531, 505 (supercooled liquid SL: literature derived value LDV, final adjust value FAV, Muir et al. 2004) Vapor Pressure (Pa at 25°C or as indicated and reported temperature dependence equations): 0.00170 (20°C, Hartley & Graham-Bryce 1980) 0.00173 (20°C, Ashton & Crafts 1981) 0.00173 (20°C, volatilization rate, Burkhard & Guth 1981) 0.00170 (20°C, Hartley & Kidd 1987) 0.00170 (20°C, Worthing & Walker 1987, Worthing & Hance 1991) 0.00173 (20°C, Herbicide Handbook 1989; Budavari 1989; Montgomery 1993) 4.20 . 10–3, 6.60 . 10–2, 0.70, 5.40, 33.0 (25, 50, 70, 100, 125°C, gas saturation-GC, Rordorf 1989) log (PL/Pa) = 13.115 – 4619.7/(T/K); measured range 32.5–140°C (gas saturation-GC, Rordorf 1989) 0.00420 (Tomlin 1994) N O O Cl © 2006 by Taylor & Francis Group, LLC 3592 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals 0.0023 (liquid PL, GC-RT correlation; Donovan 1996) 0.00418 (selected, Halfon et al. 1996) 0.00418 (20–25°C, selected, Hornsby et al. 1996) 0.00239, 0.0024 (supercooled liquid PL: literature derived value LDV, final adjust value FAV, Muir et al. 2004) Henry’s Law Constant (Pa·m3/mol at 25°C or as indicated. Additional data at other temperatures designated * are complied at the end of this section): 0.00092 (Hartley & Graham-Bryce 1980) 0.00093 (20°C, volatilization rate, Burkhard & Guth 1981) 0.00091 (20°C, calculated-P/C as per Worthing & Walker 1987) 0.00093 (20°C, calculated-P/C, Montgomery 1993) 0.00082 (20°C, calculated-P/C, Majewski & Capel 1995) 0.00244 (calculated-P/C, Otto et al. 1997) 0.00782 (20°C, distilled water, wetted wall column-GC, Rice et al. 1997b) 0.00110 (calculated-P/C, this work) 0.00238* (20°C, gas stripping-GC/MS, measured range 283.05–299.45 K, Feigenbrugel et al. 2004) H./(M atm–1) = (3.0 ± 0.4) . 10–11 exp[(10200 ± 1000)/(T/K)]; temp range 283–310 K (Arrhenius eq., gas stripping- GC/MS, Feigenbrugel et al. 2004) 0.0014. 0.0014 (literature derived value LDV, final adjust value FAV, Muir et al. 2004) Octanol/Water Partition Coefficient, log KOW: 3.13 (shake flask-HPLC, Ellgehausen et al. 1980; Geyer et al. 1991) 3.28 (shake flask-HPLC, Ellgehausen et al. 1981) 3.45 (Worthing & Hance 1991) 2.93, 3.45 (Montgomery 1993) 3.13, 3.28 (quoted, Sangster et al. 1993) 2.90 (Tomlin 1994) 3.45 (Milne 1995) 3.31, 2.95 (selected, calculated-f const., Pinsuwan et al. 1995) 3.13 (recommended, Hansch et al. 1995) 2.60 (RP-HPLC-RT correlation using short ODP column, Donovan & Pescatore 2002) 3.10 (literature derived value LDV, Muir et al. 2004) Octanol/Air Partition Coefficient, log KOA: 9.37 (final adjust value FAV, Muir et al. 2004) Bioconcentration Factor, log BCF: 1.813 (log BF-bioaccumulation of algae, Ellgehausen et al. 1980) 0.733 (log BF-bioaccumulation of daphnids, Ellgehausen et al. 1980; quoted, Geyer et al. 1991) 0.851 (log BF-bioaccumulation of catfish, Ellgehausen et al. 1980) 1.26 (calculated-S, Kenaga 1980) 1.15 (catfish Ictalurus melas, wet wt basis, Wang et al. 1996) Sorption Partition Coefficient, log KOC: 2.15 (soil, calculated-S, Kenaga 1980) 2.26 (soil, screening model calculations, Jury et al. 1987b) 2.00, 2.15, 2.28, 2.30 (soil, quoted values, Bottoni & Funari 1992) 2.46, 2.46 (soil, quoted exptl., calculated-MCI . and fragment contribution, Meylan et al. 1992) 2.30 (20–25°C, selected, Wauchope et al. 1992; Hornsby et al. 1996) 2.08–2.49 (Montgomery 1993; Tomlin 1994) 2.46 (soil, calculated-MCI 1., Sabljic et al. 1995) 2.43 (soil, estimated-general model using molecular descriptors, Gramatica et al. 2000) 2.28, 2.19, 2.69 (soils: organic carbon OC . 0.1%, OC . 0.5%, 0.1 . OC < 0 .5%, average, Delle Site 2001) Environmental Fate Rate Constants, k, or Half-Lives, t.: Volatilization: © 2006 by Taylor & Francis Group, LLC Herbicides 3593 Photolysis: under optimum exposure conditions to natural sunlight, t. ~ 8 d (Herbicide Handbook 1989). Oxidation ; kOH = 5.6 . 10–11 cm3 molecule–1 s–1 at 298 K in gas phase with atmospheric lifetime of 0.9 h but reduced to 0.4 h at 283 K; log kOH(aq.) = 1.2 . 1010 M–1 s–1 in aqueous phase (Feigenbrugel et al. 2004) Hydrolysis: t. > 200 d at 20°C and 1 . pH . 9 (Montgomery 1993); t.(calc) > 200 d (2 . pH . 10) (Tomlin 1994). Biodegradation: overall degradation rate constant k = 0.0154 h–1 with t. = 45.0 h in sewage sludge and rate constant k = 0.0460 d–1 with t. = 15.1 d in garden soil (Muller & Buser 1995). Biotransformation: Bioconcentration, Uptake (k1) and Elimination (k2) Rate Constants: k2 = 9.11 d–1 (catfish, Ellgehausen et al. 1980) k1 = 0.336 h–1, k2 = 0.024 h–1 (catfish Ictalurus melas, Wang et al. 1996) Half-Lives in the Environment: Air: Surface water: Ground water: reported t. = 20, 30, 42, and 47–107 d (Bottoni & Funari 1992) degradation time 500–1000 d (Tomlin 1994). Sediment: Soil: t. = 15–38 d in clay loam soils and t. = 33–100 d in sandy loam soils (Zimdahl & Clark 1982; quoted, Montgomery 1993); t. = 42 d from field t. = 3–4 wk by using lysimeters (Bowman 1990); t.(calc) = 80, 99 and 142 d for the disappearance from upper 15 cm on an Ontario clay loam soil while the decline was followed for 332, 364 and 370 d, respectively, in 1987, 1988 and 1989 (Frank et al. 1991); t. ~ 6 d in soil (Worthing & Hance 1991; quoted, Montgomery 1993); reported t. = 20, 30, 42, 47–107 d (Bottoni & Funari 1992) field t. = 90 d at 20–25°C (selected, Wauchope et al. 1992; quoted, Richards & Baker 1993; Halfon et al. 1996; Hornsby et al. 1996); soil t. = 40 d (Pait et al. 1992); soil t. = 28–46 d (Di Guardo et al. 1994); t. ~ 30 d (Tomlin 1994); degradation t. = 15.1 d in garden soil (Muller & Buser 1995); t. ~ 28.3 d under conventional tillage, t. ~ 25.61 d under ridge tillage and t. ~ 8.63 d with no tillage (Otto et al. 1997). Biota: t. = 1.15 d in catfish (Ellgehausen et al. 1980); biochemical t. = 42 d from screening model calculations (Jury et al. 1987b). TABLE 17.1.1.49.1 Reported Henry’s law constants of metolachlor at various temperatures Feigenbrugel et al. 2004 gas stripping-GC/MS t/°C H/(Pa m3/mol) t/°C H/(Pa m3/mol) 283.05 5.39 . 10!4 293.25 2.262 . 10!3 283.15 6.34 . 10!4 297.55 3.099 . 10!3 283.25 8.126 . 10!4 298.05 4.053 . 10!3 283.65 8.465 . 10!4 298.15 4.757 . 10!3 285.55 8.01 . 10!4 298.15 4.312 . 10!3 287.55 1.088 . 10!3 299.45 4.170 . 10!3 289.45 1.193 . 10!3 291.55 1.419 . 10!3 ln H.= A – B/(T/K) 293.05 2.702 . 10!3 H./(M/atm) 293.05 2.471 . 10!3 A !24.2298 293.15 2.282 .10!3 B 10200 293.15 2.227 .10!3 © 2006 by Taylor & Francis Group, LLC 3594 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals FIGURE 17.1.1.49.1 Logarithm of Henry’s law constant versus reciprocal temperature for metolachlor. Metolachlor: Henry's law constant vs. 1/T -9.0 -8.0 -7.0 -6.0 -5.0 -4.0 0.0032 0.0033 0.0034 0.0035 0.0036 1/(T/K) m. aP( / H nl 3 ) l om/ Feigenbrugel et al. 2004 Rice et al. 1997b © 2006 by Taylor & Francis Group, LLC Herbicides 3595 17.1.1.50 Metribuzin Common Name: Metribuzin Synonym: Metribuzine, Lexone, Preview, Sencor, Sencoral, Sencorer, Sencorex Chemical Name: 4-amino-6-(t-butyl)-3-(methylthio)-1,2,4-triazin-5-(4H)-one CAS Registry No: 21087-64-9 Uses: herbicide Molecular Formula: C8H14N4OS Molecular Weight: 214.288 Melting Point (°C): 126 (Lide 2003) Boiling Point (°C): 132.2 Pa (Tomlin 1994) Density (g/cm3 at 20°C): 1.31 (Hartley & Kidd 1987; Montgomery 1993; Tomlin 1994) 1.28 (Herbicide Handbook 1989) Dissociation Constant pKb: 13.0 (Wauchope et al. 1992; Hornsby et al. 1996) 1.0 (pKa, Montgomery 1993) Enthalpy of Fusion, .Hfus (kJ/mol): Entropy of Fusion, .Sfus (J/mol K): Fugacity Ratio at 25°C (assuming .Sfus = 56 J/mol K), F: 0.102 (mp at 126°C) Water Solubility (g/m3 or mg/L at 25°C or as indicated): 1220 (Kenaga & Goring 1980; Kenaga 1980b; Verschueren 1983) 1200 (20°C, Spencer 1982; Worthing & Walker 1983, 1987; Hartley & Kidd 1987) 1220 (Herbicide Handbook 1989) 1050 (20°C, Montgomery 1993; Tomlin 1994) 1220 (20–25°C, selected, Wauchope et al. 1992; Hornsby et al. 1996) 1065 (20–25°C, reported as 4.97E + 01 mol/m3, Majewski & Capel 1995) Vapor Pressure (Pa at 25°C or as indicated): < 1.3 . 10–3 (20°C, Worthing 1983, 1987; Hartley & Kidd 1987; Tomlin 1994) < 1.3 . 10–3; 2.67 . 10–2 (20°C; 60°C, Herbicide Handbook 1989) 5.8 . 10–5 (20°C, Montgomery 1993) < 1.3 . 10–3 (20–25°C, Wauchope et al. 1992; Hornsby et al. 1996) 5.89 . 10–4 (20–25°C, Majewski & Capel 1995) Henry’s Law Constant (Pa·m3/mol at 25°C): < 1.3 . 10–3 (Spencer 1982; Worthing 1987; Hartley & Kidd 1987) 1.21 . 10–5 (calculated-P/C, Montgomery 1993) 1.18 . 10–5 (calculated-P/C, Majewski & Capel 1995) Octanol/Water Partition Coefficient, log KOW: 1.60, 1.70 (quoted, Montgomery 1993) 1.58 (pH 5.6, Tomlin 1994) 1.70 (LOGPSTAR or CLOGP data, Sabljic et al. 1995) N N N NH2 O S © 2006 by Taylor & Francis Group, LLC 3596 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals Octanol/Air Partition Coefficient, log KOA: Bioconcentration Factor, log BCF or log KB: 2.46, 1.48, < 1.30 (algae, activated sludge, fish in 3-d testing, Korte et al. 1978) 1.77, 1.75 (Chlorella, calculated-solubility, Geyer et al. 1981) 1.77, 1.48, 1.04 (algae, activated sludge, Golden orfe, Geyer et al. 1982) 1.04, 0.602 (calculated-solubility, calculated-KOW, Kenaga 1980a) 1.48, 1.78, 1.0 (activated sludge, algae, Golden ide, Freitag et al. 1985) Sorption Partition Coefficient, log KOC: 1.98 (soil, Kenaga & Goring 1980) 1.98; 1.94 (quoted, calculated-KOW, Kenaga 1980b) 0.954–2.72 (soil, literature range, Wauchope et al. 1992) 1.80 (soil, estimated, Wauchope et al. 1992; Hornsby et al. 1996) 1.94–1.98, 2.18 (soil, Bottoni & Funari 1992) 1.80–2.72 (soil, Montgomery 1993) 1.78 (soil, Senseman et al. 1997) 1.71 (soil, calculated-MCI 1., Sabljic et al. 1995) 1.71; 1.68, 1.33 (soil, quoted obs.; estimated-class-specific model, estimated-general model using molecular descriptors, Gramatica et al. 2000) 2.05, 2.06, 2.04 (soils: organic carbon OC . 0.1%, OC . 0.5%, 0.1 . OC < 0.5%, average, Delle Site 2001) Environmental Fate Rate Constants, k, or Half-Lives, t.: Volatilization: Photolysis: photodecomposition in water is very rapid with t. < 1 d; on soil surface under natural sunlight conditions, t. = 14–25 d (Tomlin 1994). Oxidation: Hydrolysis: t. ~ 1 wk in pond water (Hartley & Kidd 1987; Montgomery 1993). Biodegradation: under goes microbial degradation in moist soil (Worthing 1987) Biotransformation: Bioconcentration, Uptake (k1) and Elimination (k2) Rate Constants: Half-Lives in the Environment: Air: Surface water: hydrolysis t. ~ 1 wk in pond water (Hartley & Kidd 1987; Montgomery 1993; Tomlin 1994); stable to dilute acids and alkalis, t. = 6.7 h at pH 1.2 and 37°C; t. = 569 h at pH 4, t. = 47 d at pH 7 and t. = 191 h at pH 9 for 70°C (Tomlin 1994). Ground water: reported half-life or persistence t. = 4–25, 17–301 and 56 d (Bottoni & Funari 1992). Sediment: Soil: undergoes microbial degradation in moist soil (Worthing 1983, 1987); half-life varies with soil types, t. ~ 90–115 d for Red River, Almasippi, and Stockton soils the 3 times this period for Newdale soil for normal application rates (Verschueren 1983); t. ~ 1–2 months in soil (Hartley & Kidd 1987; Tomlin 1994); t. ~ 30–60 d in various soil types varies greatly with climatic conditions, during the growing season (Herbicide Handbook 1989); t. = 9–12 d irrespective of the number of previous treatments in the field; t. = 25–40 d irrespective of the pretreatment history of the soil at 20°C in the laboratory (Walker & Welch 1992) reported t. = 23–120 d and the recommended field t. = 40 d (Wauchope et al. 1992; Hornsby et al. 1996; quoted, Senseman et al. 1997); half-lives of in two surface soil microcosms under nitrate, t. = 157 d and non-nitrate, t. = 187 and 349 d in reducing culture conditions at 16.4°C (Pavel et al. 1999). Biota: in mammals, following oral administration, 90% elimination within 96 h (Hartley & Kidd 1987). © 2006 by Taylor & Francis Group, LLC Herbicides 3597 17.1.1.51 Molinate Common Name: Molinate Synonym: Felan, Higalnate, Hydram, Jalan, Molmate, Ordram, Stauffer R 4572, Sakkimok, Yalan, Yulan Chemical Name: 1H-azepine-1-carbothioic acid, hexahydro, S-ethyl ester; ethyl 1-hexa-methyleneiminecarbothioate Uses: selective herbicide to control the germination of annual grasses and broadleaf weeds in rice crops. CAS Registry No: 2212-67-1 Molecular Formula: C9H17NOS Molecular Weight: 187.302 Melting Point (°C): < 25 (Montgomery 1993) Boiling Point (°C): 202 (at 10 mmHg, Hartley & Kidd 1987; Herbicide Handbook 1989; Worthing & Hance 1991; Milne 1995) 117 (at 10 mmHg, Montgomery 1993) Density (g/cm3 at 20°C): 1.064 (Hartley & Kidd 1987) 1.0643 (Herbicide Handbook 1989; Montgomery 1993) 1.063 (Worthing & Hance 1991; Milne 1995) Molar Volume (cm3/mol): 220.6 (calculated-Le Bas method at normal boiling point) 176.1 (calculated-density) Dissociation Constant pKa: Enthalpy of Fusion, .Hfus (kJ/mol): Entropy of Fusion, .Sfus (J/mol K): Fugacity Ratio at 25°C (assuming .Sfus = 56 J/mol K), F: 1.0 Water Solubility (g/m3 or mg/L at 25°C or as indicated): 880 (20°C, Weber 1972; Hartley & Kidd 1987; Worthing & Walker 1987; Worthing & Hance 1991) 800 (Martin & Worthing 1977) 800–912 (Weber et al. 1980) 912 (21°C, Spencer 1982) 800 (20°C, Herbicide Handbook 1983, 1989) 870 (Kanazawa 1989) 970 (20–25°C, selected, Wauchope et al. 1992; Hornsby et al. 1996; Armbrust 2000) 880 (20°C, Montgomery 1993; Tomlin 1994; Milne 1995) Vapor Pressure (Pa at 25°C or as indicated): 0.748 (20°C, Weber 1972; Worthing & Walker 1987) 0.746 (20°C, Khan 1980) 0.185 (20°C, GC-RT correlation, Kim 1985) 0.413 (Seiber et al. 1986, 1989) 0.746 (Hartley & Kidd 1987; Montgomery 1993; Tomlin 1994) 0.746 (Herbicide Handbook 1989; Worthing & Hance 1991) 0.746 (20–25°C, selected, Wauchope et al. 1992) Henry’s Law Constant (Pa·m3/mol at 25°C or as indicated): 0.097 (calculated-P/C, Seiber et al. 1986, 1989) 0.314 (20°C, calculated-P/C, Suntio et al. 1988) 0.159 (20°C, calculated-P/C as per Worthing & Walker 1987;) 0.159 (20°C, calculated-P/C, Muir 1991) N S O © 2006 by Taylor & Francis Group, LLC 3598 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals 0.095 (20°C, calculated-P/C, Sagebiel et al. 1992) 0.460 (20°C, gas-stripping method, Sagebiel et al. 1992) 0.390 (20°C, headspace-GC method, Sagebiel et al. 1992) 0.162 (calculated-P/C, Montgomery 1993) 0.145 (calculated-P/C, this work) 0.132 (quoted lit., Armbrust 2000) 0.397 (20°C, selected from literature experimentally measured data, Staudinger & Roberts 2001) log KAW = 6.527 – 3024/(T/K) (van’t Hoff eq. derived from literature data, Staudinger & Roberts 2001) Octanol/Water Partition Coefficient, log KOW: 3.21 (shake flask-GC, Kanazawa 1981) 2.88 (Worthing & Hance 1991; Tomlin 1994) 2.88 (Montgomery 1993) 3.13 (RP-HPLC-RT correlation, Saito et al. 1993) 3.26 (RP-HPLC-RT correlation, Sicbaldi & Finizio 1993) 3.21 (recommended, Sangster 1993) 2.88 (Milne 1995) 3.21 (recommended, Hansch et al. 1995) 3.25 (RP-HPLC-RT correlation, Finizio et al. 1997) Bioconcentration Factor, log BCF: 1.15 (calculated-S, Kenaga 1980; quoted, Pait et al. 1992) 1.41 (Peudorasbora parva, Kanazawa 1981) Sorption Partition Coefficient, log KOC: 2.04 (soil, calculated-S, Kenaga 1980) 1.92 (average of 2 soils, Kanazawa 1989) 1.92, 2.04 (soil, quoted values, Bottoni & Funari 1992) 1.92, 2.46 (soil, quoted exptl., calculated-MCI . and fragments contribution, Meylan et al. 1992) 2.28 (soil, 20–25°C, selected, Wauchope et al. 1992; Hornsby et al. 1996) 1.93–1.97 (Montgomery 1993) 2.28 (selected, Lohninger 1994) 1.92 (soil, calculated-MCI 1., Sabljic et al. 1995) 2.07 (soil, quoted lit., Armbrust 2000) 1.92; 2.31, 1.86 (soil, quoted exptl.; estimated-class specific model, estimated-general model using molecular descriptors, Gramatica et al. 2000) Environmental Fate Rate Constants, k, or Half-Lives, t.: Volatilization: k = 0.0150 h–1 (average of 2 runs, Seiber et al. 1986); 1.1 kg ha–1 (1st 4 day) from flooded rice fields (Seiber et al. 1986; Seiber & McChesney 1987); estimated t. = 43 d from 1 m depth of water at 20°C (Muir 1991). Photolysis: t. = 7–10 d for 8–10 µg mL–1 to degrade in distilled water under > 290 nm light (Soderquist et al. 1977; quoted, Cessna & Muir 1991); t. = 96 h for < 5% of 0.2 µg mL–1 to degrade in distilled water under sunlight (Deuel et al. 1978; quoted, Cessna & Muir 1991); t. = 245 h for 2–54% of 10 µg mL–1 to degrade in distilled water under sunlight (Draper & Crosby 1984; quoted, Cessna & Muir 1991). Oxidation: calculated life-time of 6 h for the vapor-phase reaction with OH radicals in the troposphere (Atkinson et al. 1992; Kwok et al. 1992); measured rate constant for reaction with hydroxyl radical, k(aq.) = 0.85 . 109 M–1·s–1 in irradiated field water both in the laboratory and sunlit rice paddies (Mabury & Crosby 1996); measured hydroxy radical reaction rate constant for molinate k = 7.7 . 1012 M–1 h–1 (Armbrust 2000). Hydrolysis: t. > 10 d in aqueous buffer at pH 5–9 in the dark (Soderquist et al. 1977; quoted, Muir 1991); stable aqueous hydrolysis rate at pH 5, 7, 9 (Armbrust 2000). © 2006 by Taylor & Francis Group, LLC Herbicides 3599 Biodegradation: t. ~16 d for 0.2 µg mL–1 to biodegrade in flooded soils (Deuel et al. 1978; quoted, Muir 1991); t. = 10 wk for 4.2 µg mL–1 to biodegrade in flooded soil and t. < 2 wk in water both at 21–26°C (Thomas & Holt 1980; quoted, Muir 1991); aerobic rate constant, k = 2.22 . 10–3 h–1 (Armbrust 2000). Biotransformation: Bioconcentration, Uptake (k1) and Elimination (k2) Rate Constants: Half-Lives in the Environment: Air: calculated lifetime of 6 h for the vapor-phase reaction with OH radicals in the troposphere (Atkinson et al. 1992; Kwok et al. 1992). Surface water: t. = 84 h from dissipation from flooded rice fields (Seiber & McChesney 1987; quoted, Seiber et al. 1989). Ground water: reported half-lives or persistence, t. = 3–14, 8–25 and 40–160 d (Bottoni & Funari 1992) Sediment: Soil: persistence of 2 months in soil (Wauchope 1978); t. ~ 3 wk in moist loam soils at 21–27°C (Herbicide Handbook 1989); selected field t. = 21 d (Wauchope et al. 1992; quoted, Halfon et al. 1996; Hornsby et al. 1996); soil t. = 21 d (Pait et al. 1992); reported t. = 3–14 d, 8–25 d and 40–160 d (Bottoni & Funari 1992). Biota: © 2006 by Taylor & Francis Group, LLC 3600 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals 17.1.1.52 Monolinuron Common Name: Monolinuron Synonym: Afesin, Aresin, Arresin, Hoe 02747 Chemical Name: 3-(4-chlorophenyl)-1-methoxy-1-methylurea; N.-(4-chlorophenyl)-N-methoxy-N-methylurea Uses: herbicide for pre- or post-emergence control of annual broadleaf weeds and annual grasses in asparagus, berry fruit, cereals, maize, field beans, vines, leeks, onions, potatoes, herbs, lucerne, flowers, ornamental shrubs and trees, etc. CAS Registry No: 1746-81-2 Molecular Formula: C9H11ClN2O2 Molecular Weight: 214.648 Melting Point (°C): 77 (Lide 2003) Boiling Point (°C): Density (g/cm3 at 20°C): Molar Volume (cm3/mol): 224.0 (calculated-Le Bas method at normal boiling point) Dissociation Constant pKa: Enthalpy of Fusion, .Hfus (kJ/mol): Entropy of Fusion, .Sfus (J/mol K): Fugacity Ratio at 25°C (assuming .Sfus = 56 J/mol K), F: 0.309 (mp at 77°C) Water Solubility (g/m3 or mg/L at 25°C or as indicated): 735 (20°C, Melnikov 1971) 735 (Spencer 1973, 1982) 580 (Martin & Worthing 1977; Khan 1980) 735 (Worthing & Walker 1983, 1987, Hartley & Kidd 1987; Worthing & Hance 1991; Tomlin 1994) 735 (20–25°C, selected, Augustijn-Beckers et al. 1994; Hornsby et al. 1996) Vapor Pressure (Pa at 25°C or as indicated): 0.02 (22°C, Khan 1980; Hartley & Kidd 1987) 0.0015 (20°C, Spencer 1982) 6.40 (65°C, Worthing & Hance 1991) 0.02 (20–25°C, selected, Augustijn-Beckers et al. 1994; Hornsby et al. 1996) 0.0013, 0.10 (20°C, 50°C, Tomlin 1994) Henry’s Law Constant (Pa·m3/mol at 25°C): 0.0058 (calculated-P/C, this work) Octanol/Water Partition Coefficient, log KOW: 1.60 (Briggs 1969) 2.30 (shake flask-UV, Briggs 1981) 1.60 (selected, Dao et al. 1983) 1.99 (RP-HPLC-k. correlation, Braumann et al. 1983) 2.22 (shake flask, Mitsutake et al.1986) 2.20 (Worthing & Hance 1991; Tomlin 1994) 2.16 (RP-HPLC-RT correlation, Sicbaldi & Finizio 1993) 2.30 (recommended, Sangster 1993) 2.30 (recommended, Hansch et al. 1995) 2.31 (Pomona-database, Muller & Kordel 1996) HN N O O Cl © 2006 by Taylor & Francis Group, LLC Herbicides 3601 2.16 (RP-HPLC-RT correlation, Finizio et al. 1997) Bioconcentration Factor, log BCF: 1.23; 1.00 (calculated-S, calculated-KOC, Kenaga 1980) 1.85 (activated sludge, Freitag et al. 1982, 1984, 1985) 1.52, < 1.0 (algae, golden orfe, Freitag et al. 1982) 1.60, 1.30 (algae, golden ide, Freitag et al. 1985) Sorption Partition Coefficient, log KOC: 2.30 (soil, Hamaker & Thompson 1972) 2.11 (soil, calculated-S as per Kenaga & Goring 1980, Kenaga 1980) 1.60 (reported as log KOM, Briggs 1981) 2.36, 2.08, 1.21 (estimated-S, calculated-S and mp, calculated-KOW, Karickhoff 1981) 2.40–2.70 (soil, Worthing & Hance 1991) 2.26–2.30, 2.40–2.70 (soil, quoted values, Bottoni & Funari 1992) 1.78 (soil, HPLC-screening method, mean value of different stationary and mobile phases, Kordel et al. 1993, 1995b) 2.30 (20–25°C, estimated, Augustijn-Beckers et al. 1994; Hornsby et al. 1996) 2.10 (soil, calculated-MCI 1., Sabljic et al. 1995) 1.78; 2.33 (HPLC-screening method; calculated-PCKOC fragment method, Muller & Kordel 1996) 2.44, 1.50, 1.71, 1.754, 2.45 (first generation Eurosoils ES-1, ES2, ES-3, ES-4, ES-5, shake flask/batch equilibrium- HPLC/UV, Gawlik et al. 1998, 1999) 2.05, 1.72, 1.695, 1.825, 2.407 (second generation Eurosoils ES-1, ES2, ES-3, ES-4, ES-5, shake flask/batch equilibrium-HPLC/UV, Gawlik et al. 1999) 2.050, 1.721, 1.695, 1.825, 2.407 (second generation Eurosoils ES-1, ES-2, ES-3, ES-4, ES-5, shake flask-batch equilibrium-HPLC/UV and HPLC-k. correlation, Gawlik et al. 2000) 2.10; 2.04, 2.31 (soil, quoted obs.; estimated-class-specific model, estimated-general model using molecular descriptors, Gramatica et al. 2000) 1.88, 1.88 (soils: organic carbon OC . 0.1%, OC . 0.5%, average, Delle Site 2001) Environmental Fate Rate Constants, k, or Half-Lives, t.: Photolysis: t. = 23 h for 66% of 286 µg/mL to degrade in distilled water under > 300 nm light (Kotzias et al. 1974; quoted, Cessna & Muir 1991). Half-Lives in the Environment: Air: Surface water: Ground water: reported half-lives or persistence, t. = 45–60 d (Bottoni & Funari 1992) Sediment: Soil: reported t. = 45–60 d (Worthing & Hance 1991); estimated field t. = 60 d (Augustijn-Beckers et al. 1994; Hornsby et al. 1996). Biota: © 2006 by Taylor & Francis Group, LLC 3602 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals 17.1.1.53 Monuron Common Name: Monuron Synonym: Chlorfenidim, CMU, Karmex, Lirobetarex, Monurex, Monurox, Rosuran, Telvar, Urox Chemical Name: N.-(4-chlorophenyl)-N-N-dimethylurea; 1,1-dimethyl-3-(p-chlorophenyl)urea Uses: herbicide; also as sugar cane flowering suppressant. CAS Registry No: 150-68-5 Molecular Formula: C9H11ClN2O Molecular Weight: 198.648 Melting Point (°C): 170.5 (Kuhne et al. 1995; Lide 2003) Boiling Point (°C): 185–200 (decomposes, Montgomery 1993) Density (g/cm3 at 20°C): 1.27 (Spencer 1982; Hartley & Kidd 1987; Montgomery 1993) Molar Volume (cm3/mol): 202.9 (calculated-Le Bas method at normal boiling point) 173.0 (modified Le Bas method, Spurlock & Biggar 1994a) Dissociation Constant pKa: Enthalpy of Fusion, .Hfus (kJ/mol): Entropy of Fusion, .Sfus (J/mol K): Fugacity Ratio at 25°C (assuming .Sfus = 56 J/mol K), F: 0.0374 (mp at 170.5°C) Water Solubility (g/m3 or mg/L at 25°C or as indicated): 203 (Freed 1966) 230 (Gunther et al. 1968; Sanborn et al. 1977; Khan 1980; Ashton & Crafts 1981) 262 (shake flask-UV, Hurle & Freed 1972) 230 (20°C, Weber 1972; Worthing & Walker 1987) 230 (Martin & Worthing 1977; Hartley & Kidd 1987) 200 (shake flask-HPLC, Ellgehausen et al. 1981) 200 (20°C, selected, Suntio et al. 1988) 275 (Spurlock 1992; Spurlock & Biggar 1994b) 230 (at pH 6.26, Montgomery 1993) 230 (20–25°C, selected, Augustijn-Beckers et al. 1994; Hornsby et al. 1996) Vapor Pressure (Pa at 25°C or as indicated and reported temperature dependence equations. Additional data at other temperatures designated * are compiled at the end of this section): 7.60 . 10–5, 1.2 . 10–5 (25, 27°C, Nex & Swezey 1954) 6.67 . 10–5 (Bailey & White 1965) 6.72 . 10–5 (20°C, Weber 1972; Worthing & Walker 1987) 6.67 . 10–5 (Ashton & Crafts 1973, 1981; Khan 1980) 5.33 . 10–5* (30.35°C, Knudsen effusion, measured range 303.5–379.1 K, Wiedemann 1972) log (P/mmHg) = 13.3052 – 5988.39/(T/K); temp range 303.5–379.1 K (Antoine eq., effusion, Wiedemann 1972) 6.70 . 10–5 (OECD 1981) 2.30 . 10–5 (calculated, Jury et al. 1983) 6.00 . 10–5 (Hartley & Kidd 1987) 6.67 . 10–5 (Budavari 1989) 2.30 . 10–5 (selected, Taylor & Spencer 1990) 6.00 . 10–5 (20°C, Montgomery 1993) 6.67 . 10–5 (20–25°C, selected, Augustijn-Beckers et al. 1994; Hornsby et al. 1996) HN N O Cl © 2006 by Taylor & Francis Group, LLC Herbicides 3603 Henry’s Law Constant (Pa·m3/mol at 25°C or as indicated): 5.80 . 10–5 (20°C, volatilization rate, Burkhard & Guth 1981) 1.88 . 10–5 (calculated-P/C, Jury et al. 1984, 1987a; Jury & Ghodrati 1989) 3.00 . 10–3 (20°C, calculated-P/C, Suntio et al. 1988) 1.91 . 10–5 (calculated-P/C, Taylor & Glotfelty 1988) 5.60 . 10–5 (20°C, calculated-P/C, Muir 1991) 3.00 . 10–3 (20°C, calculated-P/C, Montgomery 1993) 6.60 . 10–5 (calculated-P/C, this work) Octanol/Water Partition Coefficient, log KOW: 1.46 (Briggs 1969) 1.66 (calculated-fragment const., Rekker 1977) 1.80 (shake flask-UV, Erkell & Walum 1979) 2.08 (selected, Ellgehausen et al. 1980; Geyer et al. 1991) 2.12 (Rao & Davidson 1980) 1.98 (shake flask-UV, Briggs 1981) 2.08 (shake flask, Ellgehausen et al. 1980) 1.66 (shake flask, Ellgehausen et al. 1981) 1.86 (selected, Dao et al. 1983; Gerstl & Helling 1987) 1.91 (RP-HPLC-k. correlation Braumann et al. 1983) 1.80 (selected, Suntio et al. 1988) 2.12 (shake flask-HPLC, Spurlock 1992; Spurlock & Biggar 1994b) 1.46, 2.12 (Montgomery 1993) 1.86 (RP-HPLC-RT correlation, Sicbaldi & Finizio 1993) 1.94 (recommended, Sangster 1993) 1.89; 1.88 (shake flask-UV; RP-HPLC-k. correlation, Liu & Qian 1995) 1.94 (recommended, Hansch et al. 1995) 1.99 (Pomona-database, Muller & Kordel 1996) 1.86 (RP-HPLC-RT correlation, Finizio et al. 1997) Bioconcentration Factor, log BCF: 1.786 (log BF bioaccumulation factor for algae, Ellgehausen et al. 1980) 0.32 (log BF bioaccumulation factor for daphnids, Ellgehausen et al. 1980) 0.245 (log BF bioaccumulation factor for daphnids, Ellgehausen et al. 1980) 1.46 (calculated-S, Kenaga 1980) 0.699 (calculated-KOC, Kenaga 1980) 0.0 (Triaenodes tardus, Belluck & Felsot 1981) 1.58, 1.67 (cuticle/water: tomato, pepper; Evelyne et al. 1992) Sorption Partition Coefficient, log KOC: 2.00 (soil, Hamaker & Thompson 1972) 2.34 (soil, calculated-S as per Kenaga & Goring 1980, Kenaga 1980) 2.26 (av. of 18 soils, Rao & Davidson 1980) 1.70 (soil, converted from reported KOM, multiplied by 1,724, Briggs 1981) 2.58, 1.51 (estimated-S, calculated-S and mp, Karickhoff 1981) 1.07, 1.73 2.58 (estimated-KOW, Karickhoff 1981) 2.03, 1.85; 2.17, 1.52 (estimated-KOWs; solubilities, Madhun et al. 1986) 1.99; 2.12 (quoted; calculated-MCI ., Gerstl & Helling 1987) 2.26 (screening model calculations, Jury et al. 1987a,b; Jury & Ghoodrati 1989) 1.99, 2.33 (Montgomery 1993) 2.18 (20–25°C, estimated, Augustijn-Beckers et al. 1994; Hornsby et al. 1996) 1.99 (soil, HPLC-screening method, mean value from different stationary and mobile phases, Kordel et al. 1993, 1995a,b) 2.29 (calculated-KOW, Liu & Qian 1995) 1.95 (soil, calculated-MCI 1., Sabljic et al. 1995) © 2006 by Taylor & Francis Group, LLC 3604 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals 1.99; 1.92 (HPLC-screening method; calculated-PCKOC fragment method, Muller & Kordel 1996) 2.58, 1.77, 1.85, 1.77, 2.41 (first generation Eurosoils ES-1, ES2, ES-3, ES-4, ES-5, shake flask/batch equilibrium- HPLC/UV, Gawlik et al. 1998, 1999) 2.14, 2.018, 1.79, 1.764, 2.243 (second generation Eurosoils ES-1, ES2, ES-3, ES-4, ES-5, shake flask/batch equilibrium-HPLC/UV, Gawlik et al. 1999) 2.141, 2.018, 1.793, 1.764, 2.243 (second generation Eurosoils ES-1, ES-2, ES-3, ES-4, ES-5, shake flask/batch equilibrium-HPLC/UV and HPLC-k. correlation, Gawlik et al. 2000) 1.95; 1.96, 2.13 (soil, quoted obs.; estimated-class-specific model, estimated-general model using molecular descriptors, Gramatica et al. 2000) 1.80, 1.80 (soils: organic carbon OC . 0.1%, OC . 0.5%, average, Delle Site 2001) Environmental Fate Rate Constants, k, or Half-Lives, t.: Volatilization: Photolysis: t. = 14 d for 6% of 200 µg mL–1 to degrade in distilled water under sunlight (Crosby & Tang 1969; quoted, Cessna & Muir 1991); t. = 2.25 h for 44% of 200 µg mL–1 to degrade in distilled water under 300 nm light (Tanaka et al. 1977; quoted, Cessna & Muir 1991); t. = 2.25 s for 75% of 100 µg mL–1 to degrade in 0.2% Triton X-100 aqueous solution under 300 nm light (Tanaka et al. 1981; quoted, Cessna & Muir 1991); t. = 2.25 h for > 70% of 200 µg mL–1 to degrade in aqueous solutions of nonionic surfactants at concns. in excess of critical micelle concn. under 300 nm light (Tanaka et al. 1979; quoted, Cessna & Muir 1991); t. = 45 h for 69% of 165 µg mL–1 to degrade in distilled water under > 280 nm light (Tanaka et al. 1982; quoted, Cessna & Muir 1991). Oxidation: Hydrolysis: t. > 4 months for 3974 µg mL–1 to hydrolyze in phosphate buffer at pH 5–9 and 20°C (El-Dib & Aly 1976; quoted, Muir 1991). Biodegradation: aerobic t. . 7 d for 0.01 µg mL–1 to biodegrade in river water (Eichelberger & Lichtenberg 1971; quoted, Muir 1991); t. = 166 d for a 100 d leaching and screening test in 0–10 cm depth of soil (Jury et al. 1983, 1984, 1987a,b; Jury & Ghodrati 1989); aerobic t. . 10–15 d for 0.0005–10 µg mL–1 to biodegrade in filtered sewage water at 20°C (Wang et al. 1985; quoted, Muir 1991). Biotransformation: Bioconcentration, Uptake (k1) and Elimination (k2) Rate Constants: k2 = 21.05 d–1 (catfish, Ellgehausen et al. 1980) Half-Lives in the Environment: Air: Surface water: persistence of up to 8 wk in river water (Eichelberger & Lichtenberg 1971). Ground water: Sediment: Soil: t. = 5.0 months at 15°C and 4.1 months at 30°C in soils (Freed & Haque 1973); reported t. = 166 d from screening model calculations (Jury et al. 1987a,b; Jury & Ghodrati 1989; quoted, Montgomery 1993); estimated field t. = 170 d (Augustijn-Beckers et al. 1994; Hornsby et al. 1996). Biota: t. = 0.45 d in catfish (Ellgehausen et al. 1980); biochemical t. = 166 d from screening model calculations (Jury et al. 1987a,b; Jury & Ghodrati 1989). © 2006 by Taylor & Francis Group, LLC Herbicides 3605 TABLE 17.1.1.53.1 Reported vapor pressures of monuron at various temperatures Wiedemann 1972 Knudsen effusion T/K P/Pa T/K P/Pa 303.5 5.33 . 10!5 358.7 0.0536 316.0 2.44 . 10!4 360.2 0.0561 329.8 2.16 . 10!3 379.1 0.399 330.6 1.53 . 10!3 330.6 2.22 . 10!3 log P = A – B/(T/K) 338.8 7.05 . 10!3 P/mmHg 341.4 9.45 . 10!3 A 13.3952 345.7 0.0105 B 5988.39 349.5 0.0204 357.0 0.0529 .Hsubl/(kJ mol–1) = 114.6 FIGURE 17.1.1.53.1 Logarithm of vapor pressure versus reciprocal temperature for monuron. Monuron: vapor pressure vs. 1/T -6.0 -5.0 -4.0 -3.0 -2.0 -1.0 0.0 1.0 2.0 0.0022 0.0024 0.0026 0.0028 0.003 0.0032 0.0034 0.0036 1/(T/K) P( gol S ) aP/ Wiedemann 1972 m.p. = 170.5 °C © 2006 by Taylor & Francis Group, LLC 3606 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals 17.1.1.54 Napropamide Common Name: Napropamide Synonym: Devrinol Chemical Name: 2-(.-naphthloxy)-N,N-diethylpropionamide CAS Registry No: 15299-99-7 Uses: herbicide Molecular Formula: C17H21NO2 Molecular Weight: 271.355 Melting Point (°C): 75 (Worthing & Walker 1987; Lide 2003) Density (g/cm3 at 20°C): Molar Volume (cm3/mol): Dissociation Constant pKa: 2.93 (Woodburn et al. 1993) Enthalpy of Fusion, .Hfus (kJ/mol): Entropy of Fusion, .Sfus (J/mol K): Fugacity Ratio at 25°C (assuming .Sfus = 56 J/mol K), F: 0.323 (mp at 75°C) Water Solubility (g/m3 or mg/L at 25°C or as indicated): 69 (shake flask-LSC or GC, Gerstl & Mingelgrin 1984) 73 (20°C, Spencer 1982; Hartley & Kidd 1987; Worthing & Walker 1987; Herbicide Handbook 1989; Montgomery 1993; Tomlin 1994) 74 (20–25°C, selected, Wauchope et al. 1992; Hornsby et al. 1996) Vapor Pressure (Pa at 25°C or as indicated): 2.67 . 10–4 (Spencer 1982) 5.3 . 10–4 (Herbicide Handbook 1989) 5.3 . 10–4 (Hartley & Kidd 1987; Worthing & Walker 1987; Montgomery 1993; Tomlin 1994) 2.27 . 10–5 (20–25°C, selected, Wauchope et al. 1992; Hornsby et al. 1996) 1.67 . 10–3 (20–25°C, Majewski & Capel 1995) Henry’s Law Constant (Pa·m3/mol at 25°C or as indicated): 0.00294 (calculated-P/C, Montgomery 1993) 0.00197 (20–25°C, Majewski & Capel 1995) Octanol/Water Partition Coefficient, log KOW: 3.08 (shake flask-GC or LSC, Gerstl & Mingelgrin 1984) 3.36 (Montgomery 1993) 3.30 (Tomlin 1994) 3.36 (recommended, Hansch et al. 1995) Octanol/Air Partition Coefficient, log KOA: Bioconcentration Factor, log BCF or log KB: Sorption Partition Coefficient, log KOC: 2.04–3.09 (various soils, Mingelgrin & Gestl 1983) 2.82, 3.56 (soil: quoted, calculated-MCI ., Gerstl & Helling 1987) O N O © 2006 by Taylor & Francis Group, LLC Herbicides 3607 2.62 (soil, average of log KOC values, Gerstl 1990) 3.52–4.29; 3.72 at pH 2, 3.35 at pH 6 (Dead sea sediment, Gestl & Kilger 1990) 2.62–3.54; 3.54 at pH 2, 3.40 at pH 6 (Kinnert F sediment, Gestl & Kilger 1990) 2.71–3.62; 3.62 at pH 2, 3.27 at pH 6 (Kinnert G sediment, Gestl & Kilger 1990) 2.40–3.31; 3.31 at pH 2, 3.20 at pH 5 (Oxford soil, Gestl & Kilger 1990) 2.39–3.15; 3.15 at pH 2, 2.88 at pH 6 (Malkiya soil, Gestl & Kilger 1990) 2.28–3.29; 3.29 at pH 2, 3.09 at pH 5 (Neve Ya’ar soil, Gestl & Kilger 1990) 2.85 (soil, Wauchope et al. 1992; Hornsby et al. 1996) 2.29–3.99 (soil/sediment, literature range, Montgomery 1993) 2.83 (soil, Montgomery 1993) 2.62 (soil, calculated-MCI ., Sabljic et al. 1995) 2.58, 2.58, 2.61 (soils: organic carbon OC . 0.1%, OC . 0.5%, 0.1 . OC < 0.5%, average, Delle Site 2001) 2.80 (sediment: organic carbon OC . 0.5%, average, Delle Site 2001) Environmental Fate Rate Constants, k, or Half-Lives, t.: Volatilization: very little loss occurred by volatilization from soil surface (Herbicide Handbook 1989). Photolysis: under condition of high sunlight intensity in the summer, t. ~ 4 d on the soil surface (Herbicide Handbook 1989); decomposed by sunlight, t. = 25.7 min. (Tomlin 1994). Oxidation: Hydrolysis: stable to hydrolysis between pH 4 and 10 at 40°C (Hartley & Kidd 1987; Worthing 1987; Tomlin 1994). Biodegradation: slowly broken down by microorganisms in soil, in pure culture, a soil fungus metabolizes rapidly with t. = 2 wk (Herbicide Handbook 1989). Biotransformation: rapidly metabolized in plants to water-soluble metabolites (Tomlin 1994). Bioconcentration, Uptake (k1) and Elimination (k2) Rate Constants: Half-Lives in the Environment: Air: Surface water: Ground water: decomposed by sunlight, t. = 25.7 min. (Montgomery 1993; Tomlin 1994). Sediment: Soil: t. ~ 55 d in the plots treated for the first time whereas t. = 6–12 d in pre-treated plots that had previously been sprayed with napropamide in the field; t. = 25–40 d irrespective of the pre-treatment history of the soil in the laboratory at 20°C (Walker & Welch 1992) t. ~ 8–12 wk (Hartley & Kidd 1987; Tomlin 1994); field t. = 70 d (Wauchope et al. 1992; Hornsby et al. 1996); moist loam or sandy-loam soils at 79–90°C, t. = 8–12 wk (Montgomery 1993). Biota: rapidly metabolized in plants to water-soluble metabolites (Tomlin 1994). © 2006 by Taylor & Francis Group, LLC 3608 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals 17.1.1.55 Neburon Common Name: Neburon Synonym: Kloben, Neburea, Neburex Chemical Name: 1-butyl-3-(3,4-dichlorophenyl)-1-methylurea; N-butyl-N.(3,4-dichloro-phenyl)-N-methylurea Uses: pre-emergence herbicide to control grasses and broadleaf weeds in peas, beans, lucerne, garlic, beets, cereals, strawberries, ornamentals and forestry. CAS Registry No: 555-37-3 Molecular Formula: C12H16Cl2N2O Molecular Weight: 275.174 Melting Point (°C): 102–103 (Khan 1980; Spencer 1982; Worthing & Hance 1991; Tomlin 1994) 101.5–103 (Montgomery 1993) Boiling Point (°C): Density (g/cm3 at 20°C): Molar Volume (cm3/mol): 236.0 (modified Le Bas method at normal boiling point, Spurlock & Biggar 1994a) Dissociation Constant pKa: Enthalpy of Vaporization, .HV (kJ/mol): 96.91 (Rordorf 1989) Enthalpy of Fusion, .Hfus (kJ/mol): 29.71 (DSC method, Plato & Glasgow 1969) 26.9 (Rordorf 1989) Entropy of Fusion, .Sfus (J/mol K): Fugacity Ratio at 25°C (assuming .Sfus = 56 J/mol K), F: Water Solubility (g/m3 or mg/L at 25°C or as indicated): 4.8 (24°C, Bailey & White 1965; Melnikov 1971) 4.8 (Martin & Worthing 1977) 4.8 (28°C, Khan 1980) 5.0 (Hartley & Kidd 1987; Tomlin 1994) 4.8 (24°C, Worthing & Walker 1987, Worthing & Hance 1991; Montgomery 1993) 5.2 (Spurlock 1992; Spurlock & Biggar 1994b) 5.0 (20–25°C, selected, Augustijn-Beckers et al. 1994; selected, Hornsby et al. 1996) 4.67, 9.99 (quoted, calculated-group contribution fragmentation method, Kuhne et al. 1995) Vapor Pressure (Pa at 25°C or as indicated and reported temperature dependence equations): 6.30 . 10–6, 4.10 . 10–4, 0.015, 0.33, 4.90 (25, 50, 70, 100, 125°C, gas saturation-GC, Rordorf 1989) log (PS/Pa) = 18.272 – 6999.1/(T/K); measured range 50–103°C (solid, gas saturation-GC, Rordorf 1989) log (PL/Pa) = 13.285 – 5062.2/(T/K); measured range 105–140°C (liquid, gas saturation-GC, Rordorf 1989) Henry’s Law Constant (Pa·m3/mol at 25°C): Octanol/Water Partition Coefficient, log KOW: 4.59 (selected, Dao et al. 1983; Gerstl & Helling 1987) 4.31 (RP-HPLC-k. correlation, Braumann et al. 1983) 4.22 (Spurlock 1992; Spurlock & Biggar 1994b) 3.80 (selected, Sangster 1993) 3.80 (calculated, Montgomery 1993) HN N O Cl Cl © 2006 by Taylor & Francis Group, LLC Herbicides 3609 4.10 (shake flask-UV, Liu & Qian 1995) 3.99 (RP-HPLC-k. correlation, Liu & Qian 1995) 3.80 (recommended, Hansch et al. 1995) 3.40, 4.02, 4.13 (RP-HPLC-RT correlation, CLOGP, calculated-S, Finizio et al. 1997) Bioconcentration Factor, log BCF: 2.41 (calculated-S, Kenaga 1980; quoted, Isensee 1991) 1.85, 2.18 (calculated-S, KOC, Kenaga 1980) Sorption Partition Coefficient, log KOC: 3.36 (soil, Hamaker & Thompson 1972) 3.26, 2.72 (soil, calculated-S, Kenaga 1980) 3.49 (average of soils/sediments, Rao & Davidson 1980) 3.36, 3.23 (quoted, calculated-MCI ., Gerstl & Helling 1987) 2.95 (soil, calculated-. and fragment contribution, Meylan et al. 1992) 3.49 (Montgomery 1993) 3.40 (20–25°C, selected, Augustijn-Beckers et al. 1994; Hornsby et al. 1996) 3.40 (selected, Lohninger 1994) 3.60 (calculated-KOW, Liu & Qian 1995) 3.140 (soil, calculated-MCI 1., Sabljic et al. 1995) 3.40; 2.86, 2.69 (soil, quoted exptl.; estimated-class-specific model, estimated-general model using molecular descriptors, Gramatica et al. 2000) Environmental Fate Rate Constants, k, or Half-Lives, t.: Hydrolysis: t. > 4 months for 5500 µg/mL to hydrolyze in phosphate buffer at pH 5–9 and 20°C (El-dib & Aly 1976; quoted, Muir 1991). Half-Lives in the Environment: Soil: residual activity in soil is limited to approximately 3–4 months (Hartley & Kidd 1987; quoted, Montgomery 1993); selected field t. = 120 d (Augustijn-Beckers et al. 1994; Hornsby et al. 1996). © 2006 by Taylor & Francis Group, LLC 3610 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals 17.1.1.56 Nitralin Common Name: Nitralin Synonym: Planavin Chemical Name: 4-(methylsulfonyl)-2,6-dinitro-N,N-dipropylbenzamine CAS Registry No: 4726-14-1 Uses: herbicide Molecular Formula: C13H19N3O6S Molecular Weight: 345.371 Melting Point (°C): 150 (Lide 2003) Boiling Point (°C): Density (g/cm3 at 20°C): 1.39 (Hartley & Kidd 1987) Molar Volume (cm3/mol): Dissociation Constant pKa: Enthalpy of Fusion, .Hfus (kJ/mol): Entropy of Fusion, .Sfus (J/mol K): Fugacity Ratio at 25°C (assuming .Sfus = 56 J/mol K), F: 0.0594 (mp at 150°C) Water Solubility (g/m3 or mg/L at 25°C): 0.60 (Melnikov 1971; Kenaga & Goring 1980; Kenaga 1980b; Isensee 1991) 0.60 (Ashton & Crafts 1981; Hartley & Kidd 1987; Worthing & Walker 1987) Vapor Pressure (Pa at 25°C): 0.240 (Ashton & Crafts 1981) 2.0 . 10–5 (Hartley & Kidd 1987) Henry’s Law Constant (Pa·m3/mol): Octanol/Water Partition Coefficient, log KOW: 6.73 (calculated-MCI ., Patil 1994) 2.81 (LOGPSTAR or CLOGP data, Sabljic et al. 1995) Octanol/Air Partition Coefficient, log KOA: Bioconcentration Factor, log BCF or log KB: 2.90, 1.76 (calculated-solubility, KOW, Kenaga 1980b) Sorption Partition Coefficient, log KOC: 2.98 (Kenaga & Goring 1980) 3.76 (calculated, Kenaga 1980a) 2.92 (soil, calculated-MCI ., Sabljic et al. 1995) 2.92; 3.28 (soil, quoted obs.; estimated-general model using molecular descriptors, Gramatica et al. 2000) Environmental Fate Rate Constants, k, or Half-Lives, t.: Biotransformation: Degradation by abiotic reductive transformations: k = 3.44 M–1 s–1 in H2S with (mecapto)juglone (hydroquinone moiety, an abiotic reductant found in natural systems) solution at pH 6.65 (Wang & Arnold 2003) Aqueous solutions with surface-bound Fe(II) species and their furst-order rate constants as: N NO2 O2N S O O © 2006 by Taylor & Francis Group, LLC Herbicides 3611 k = 0.44 . 10–3 h–1 at pH 6.5, k = 0.68 . 10–2 h–1 at pH 7.0, k = 0.133 h–1 at pH 7.4, and k = 1.96 h–1 at pH 7.8 for aqueous ferrous ion system; k = 0.580 h–1 at pH 6.5, k = 1.15 h–1 at pH 6.7, k = 6.06 h–1 at pH 7.0, and k = 20.9 h–1 at pH 7.3 for Fe(II)/goethite system; k = 2.54 . 10–3 h–1 at pH 6.5, k = 1.83 . 10–3 h–1 at pH 7.0, k = 4.13 . 10–3 h–1 at pH 7.4 and k = 7.70 . 10–3 h–1 at pH 7.8 for Fe(II)/clay system, all with total dissolved Fe(II) = 1 mM(Wang & Arnold 2003) Half-Lives in the Environment: Air: Surface water: Ground water: Sediment: Soil: t. ~ 30–54 d in dry soil (Hartley & Kidd 1987) Biota: in mammals, following oral administration, degradation and elimination occur within a few days (Hartley & Kidd 1987). © 2006 by Taylor & Francis Group, LLC 3612 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals 17.1.1.57 Nitrofen Common Name: Nitrofen Synonym: nitrophen Tok, Tokkron Chemical Name: 2,4-dichloro-1-(4-nitrophenoxy)benzene CAS Registry No: 1836-75-5 Uses: herbicide Molecular Formula: C12H7Cl2NO3 Molecular Weight: 284.095 Melting Point (°C): 70 (Lide 2003) Boiling Point (°C): 180–190/0.25 mmHg (Hartley & Kidd 1987) Density (g/cm3 at 20°C): Molar Volume (cm3/mol): Dissociation Constant pKa: Enthalpy of Vaporization, .HV (kJ/mol): 93.66 (Rordorf 1989) Enthalpy of Fusion, .Hfus (kJ/mol): 22,7 (Rordorf 1989) Entropy of Fusion, .Sfus (J/mol K): Fugacity Ratio at 25°C (assuming .Sfus = 56 J/mol K), F: 0.362 (mp at 70°C) Water Solubility (g/m3 or mg/L at 25°C or as indicated): 1.0 (Kenaga 1980b) ~1.0 (Spencer 1982) 0.7–1.2 (22°C, Worthing 1987) ~1 (room temp., Hartley & Kidd 1987) 1.0 (20–25°C, selected, Augustijn-Beckers et al. 1994; Hornsby et a;. 1996) Vapor Pressure (Pa at 25°C or as indicated and reported temperature dependence equations.): 1.07 . 10–3 (40°C, Spencer 1982) 1.06 . 10–3 (40°C, Worthing 1987; Hartley & Kidd 1987) 1.30 . 10–4, 4.50 . 10–3, 0.091, 1.20, 12.0 (25, 50, 70, 100, 125°C, gas saturation-GC, Rordorf 1989) log (PS/Pa) = 15.867 – 5886.5/(T/K); measured range 50–70.2°C (solid, gas saturation-GC, Rordorf 1989) log (PL/Pa) = 13.022 – 4892.8/(T/K); measured range 72.7–140°C (liquid, gas saturation-GC, Rordorf 1989) 1.33 . 10–5 (20–25°C, selected, Augustijn-Beckers et al. 1994; Hornsby et al. 1996) Henry’s Law Constant (Pa·m3/mol): Octanol/Water Partition Coefficient, log KOW: 3.09 (Rao & Davidson 1980) Octanol/Air Partition Coefficient, log KOA: Bioconcentration Factor, log BCF or log KB: 2.79 (fish, Kenaga 1980b) Sorption Partition Coefficient, log KOC: 3.64 (soil, calculated, Kenaga 1980b) 3.01, 3.64, 4.18, 4.05 (quoted literature values, Augustijn-Beckers et al. 1994) 4.0 (soil, Augustijn-Beckers et al. 1994; Hornsby et al. 1996) O O2N Cl Cl © 2006 by Taylor & Francis Group, LLC Herbicides 3613 Environmental Fate Rate Constants, k, or Half-Lives, t.: Half-Lives in the Environment: Soil: reported field t. = 3 to 25 d and the recommended field t. = 30 d (Augustijn-Beckers et al. 1994; Hornsby et al. 1996). © 2006 by Taylor & Francis Group, LLC 3614 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals 17.1.1.58 Norflurazon Common Name: Norflurazon Synonym: Zorial, Solicam, Evital, Telok Chemical Name: 4-chloro-5-(methylamino)-2[3-(trifluoromethyl)phenyl]-3-(2H)-pyridazinone CAS Registry No: 27314-13-2 Uses: herbicide Molecular Formula: C12H9ClF3N3O Molecular Weight: 303.666 Melting Point (°C): 184 (Lide 2003) Boiling Point (°C): Density (g/cm3 at 20°C): Molar Volume (cm3/mol): Dissociation Constant pKa: Enthalpy of Fusion, .Hfus (kJ/mol): Entropy of Fusion, .Sfus (J/mol K): Fugacity Ratio at 25°C (assuming .Sfus = 56 J/mol K), F: 0.0275 (mp at 184°C) Water Solubility (g/m3 or mg/L at 25°C or as indicated): 28 (Kenaga & Goring 1980; Kenaga 1980b; Gerstl & Helling 1987; Isensee 1991) 28 (Ashton & Crafts 1981; Worthing & Walker 1987; Herbicide Handbook 1989; Tomlin 1994) 40 (Spencer 1982) 28 (23°C, Hartley & Kidd 1987) 28 (20–25°C, selected, Wauchope et al. 1992; Hornsby et al. 1996; quoted, Senseman et al. 1997) Vapor Pressure (Pa at 25°C or as indicated): 2.7 . 10–6 (20°C, Ashton & Crafts 1981; Spencer 1982) 2.8 . 10–6 (20°C, Worthing & Walker 1987; Tomlin 1994) 2.7 . 10–6, 3.3 . 10–5, 3.3 . 10–4, 1.6 . 10–3, 1.3 . 10–2 (20, 40, 60, 80, 100°C, Herbicide Handbook 1989) 9.24 . 10–5 (20–25°C, Majewski & Capel 1995) Henry’s Law Constant (Pa·m3/mol at 25°C or as indicated): 3.04 . 10–5 (20–25°C, Majewski & Capel 1995) Octanol/Water Partition Coefficient, log KOW: 2.30 (22°C, shake flask-UV, Braumann & Grimme 1981) 2.52 (shake flask, Takahashi et al. 1993) 2.45 (pH 6.5, Tomlin 1994) 2.30 (recommended, Hansch et al. 1995) 2.30 (LOGPSTAR or CLOGP data, Sabljic et al. 1995) 2.60 (RP-HPLC-RT correlation using short ODP column, Donovan & Pescatore 2002) Octanol/Air Partition Coefficient, log KOA: Bioconcentration Factor, log BCF or log KB: 1.97 (fish, calculated-solubility, Kenaga 1980b; Isensee 1991) N N Cl HN O F F F © 2006 by Taylor & Francis Group, LLC Herbicides 3615 Sorption Partition Coefficient, log KOC: 3.28 (soil, Kenaga & Goring 1980) 2.85 (calculated-solubility, Kenaga 1980b) 3.28, 3.07 (soil: quoted, calculated-MCI ., Gerstl & Helling 1987) 2.85 (soil, Wauchope et al. 1992; Hornsby et al. 1996) 3.02, 2.64, 3.02, 2.46 2.59 (sandy loam, Mississippi loam, Mississippi sediment, Keaton sandy loam, Biggs clay, Tomlin 1994) 3.75 (calculated-MCI ., Meylan et al. 1992) 3.28 (soil, calculated-MCI ., Sabljic et al. 1995) 2.78 (soil, Senseman et al. 1997) Environmental Fate Rate Constants, or Half-Lives, t.: Volatilization: dissipated in soil by photodegradation and volatilization, t. = 45–180 d (Tomlin 1994) Photolysis: rapidly degraded by sunlight (Worthing 1987; Tomlin 1994) dissipated in soil by photodegradation and volatilization, t. = 45–180 d (Tomlin 1994) Oxidation: Hydrolysis: Biodegradation: Biotransformation: Bioconcentration, Uptake (k1) and Elimination (k2) Rate Constants: Half-Lives in the Environment: Air: Surface water: t. = 3.4 and 1.9 d reported in the absence and presence of 20 ppm H2O2 (quoted, Massad et al. 2004) Ground water: Sediment: Soil: the average t. = 45–130 d residues in soil from the Delta and Southeast depending on clay and organic content (Herbicide Handbook 1989) field t. ~ 30 d (estimated, Wauchope et al. 1992; Hornsby et al. 1996) dissipated in soil by photodegradation and volatilization, t. = 45–180 d (Tomlin 1994) soil t. = 90 d (Senseman et al. 1997) Biota: © 2006 by Taylor & Francis Group, LLC 3616 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals 17.1.1.59 Oryzalin Common Name: Oryzalin Synonym: Dirimal, EL 119, Rycelan, Rycelon, Ryzelan, Surflan Chemical Name: 4-(dipropylamino)-3,5-dinitrobenzene-sulfonamide; 3,5-dinitro-N4, N4-dipropylsulfanilamide Uses: herbicide for pre-emergence control of many annual grasses and broadleaf weeds in cotton, fruit trees, vines, nut trees, soybeans, groundnuts, oilseed rape, sunflowers, lucerne, peas, sweet potatoes, mint, ornamentals and also used in noncrop areas. CAS Registry No: 19044-88-3 Molecular Formula: C12H18N4O6S Molecular Weight: 346.359 Melting Point (°C): 141 (Lide 2003) Boiling Point (°C): 265 (dec. Tomlin 1994) Density (g/cm3 at 20°C): Molar Volume (cm3/mol): 351.1 (calculated-Le Bas method at normal boiling point) Dissociation Constant pKa: 9.40 (Worthing & Hance 1991; Tomlin 1994) 8.60 (Wauchope et al. 1992; Hornsby et al. 1996) Enthalpy of Fusion, .Hfus (kJ/mol): Entropy of Fusion, .Sfus (J/mol K): Fugacity Ratio at 25°C (assuming .Sfus = 56 J/mol K), F: 0.0728 (mp at 141°C) Water Solubility (g/m3 or mg/L at 25°C or as indicated): 2.4 (Martin & Worthing 1977; Spencer 1982; Ashton & Crafts 1981) 2.6 (Weber et al. 1980) 2.5 (Hartley & Kidd 1987; Budavari 1989; Milne 1995) 2.4 (Worthing & Walker 1987, Worthing & Hance 1991) 2.6 (Herbicide Handbook 1989; Tomlin 1994) 2.5 (20–25°C, selected, Wauchope et al. 1992; Hornsby et al. 1996) 3.5 (calculated-group contribution fragmentation method, Kuhne et al. 1995) Vapor Pressure (Pa at 25°C or as indicated): < 1.33 . 10–5 (30°C, Ashton & Crafts 1981) < 1.30 . 10–5 (30°C, Hartley & Kidd 1987) < 1.33 . 10–6 (Herbicide Handbook 1989; Tomlin 1994) < 1.33 . 10–5 (30°C, Budavari 1989) < 1.30 . 10–6 (Worthing & Hance 1991) < 1.30 . 10–6 (20–25°C, selected, Wauchope et al. 1992; Hornsby et al. 1996) Henry’s Law Constant (Pa·m3/mol at 25°C): 0.000188 (calculated-P/C, this work) Octanol/Water Partition Coefficient, log KOW: 4.13 (selected, Dao et al. 1983) 3.73 (Worthing & Hance 1991) N NO2 O2N S O O NH2 © 2006 by Taylor & Francis Group, LLC Herbicides 3617 3.72 (pH 7, Tomlin 1994) 3.73 (Milne 1995) 3.73 (selected, Hansch et al. 1995) 2.79 (MedChem master file or ClogP program, Sabljic et al. 1995) Bioconcentration Factor, log BCF: 2.58 (calculated-S, Kenaga 1980) Sorption Partition Coefficient, log KOC: 3.43 (soil, calculated-S, Kenaga 1980) 2.78 (soil, 20–25°C, selected, Wauchope et al. 1992; Hornsby et al. 1996) 2.78 (estimated-chemical structure, Lohninger 1994) 2.85–3.04 (Tomlin 1994) 3.40 (quoted or calculated-QSAR MCI 1., Sabljic et al. 1995) 3.40; 3.18 (soil, quoted obs.; estimated-general model using molecular descriptors, Gramatica et al. 2000) Environmental Fate Rate Constants, k, or Half-Lives, t.: Biodegradation: in soil, microbial degradation occurs rapidly, t. = 2.1 months for aerobic and t. = 10 d for anaerobic metabolism (Tomlin 1994). Half-Lives in the Environment: Soil: selected field t. = 20 d (Wauchope et al. 1992; Hornsby et al. 1996); t. = 2.1 months for aerobic degradation and t. = 10 d for anaerobic degradation (Tomlin 1994). © 2006 by Taylor & Francis Group, LLC 3618 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals 17.1.1.60 Pebulate Common Name: Pebulate Synonym: PEBC, R-2061, Stauffer 2061, Tillam, Timmam-6-E Chemical Name: S-propyl butylethyl(thiocarbamate); S-propyl butylethylcarbamothioate Uses: selective pre-emergence herbicide to control annual grasses and broadleaf weeds in tomatoes, sugar beet, and tobacco. CAS Registry No: 1114-71-2 Molecular Formula: C10H21NOS Molecular Weight: 203.345 Melting Point (°C): liquid Boiling Point (°C): 142 (at 20 mmHg, Hartley & Kidd 1987; Budavari 1989; Montgomery 1993; Milne 1995) 142 (at 21 mmHg, Herbicide Handbook 1989) Density (g/cm3 at 20°C): 0.956 (Hartley & Kidd 1987; Worthing & Hance 1991; Tomlin 1994; Milne 1995) 0.9555 (Herbicide Handbook 1989; Montgomery 1993) Molar Volume (cm3/mol): 258.7 (calculated-Le Bas method at normal boiling point) Dissociation Constant pKa: Enthalpy of Fusion, .Hfus (kJ/mol): Entropy of Fusion, .Sfus (J/mol K): Fugacity Ratio at 25°C (assuming .Sfus = 56 J/mol K), F: 1.0 Water Solubility (g/m3 or mg/L at 25°C or as indicated): 92 (21°C, Woodford & Evans 1963) 92 (21°C, Spencer 1973, 1982) 60 (Herbicide Handbook 1978, 1989; quoted, Kenaga 1980; Kenaga & Goring 1980) 60 (Ashton & Crafts 1973, 1981) 60 (20°C, Khan 1980; Hartley & Kidd 1987; Tomlin 1994; Montgomery 1993; Milne 1995) 60 (20°C, Worthing & Walker 1987, Worthing & Hance 1991) 100 (20–25°C, selected, Wauchope et al. 1992; Hornsby et al. 1996) Vapor Pressure (Pa at 25°C or as indicated): 4.67 (Ashton & Crafts 1973, 1981; Herbicide Handbook 1989) 3.60 (20°C, Hartley& Graham-Bryce 1980) 9.06 (30°C, Khan 1980) 0.216 (20°C, GC-RT correlation, Kim 1985) 9.00 (30°C, Hartley & Kidd 1987; Tomlin 1994) 3.50 (20°C, selected, Suntio et al. 1988) 4.70 (Worthing & Hance 1991; Tomlin 1994) 1.186 (20–25°C, selected, Wauchope et al. 1992; Hornsby et al. 1996) 9.064 (20°C, Montgomery 1993) Henry’s Law Constant (Pa·m3/mol at 25°C or as indicated): 11.67 (20°C, calculated-P/C, Suntio et al. 1988) 11.65 (20°C, calculated-P/C, Montgomery 1993) Octanol/Water Partition Coefficient, log KOW: 3.78 (selected, Magee 1991) 3.84 (Worthing & Hance 1991; Montgomery 1993; Milne 1995) S N O © 2006 by Taylor & Francis Group, LLC Herbicides 3619 3.83 (Tomlin 1994) 3.84 (selected, Hansch et al. 1995) 4.19, 3.74, 3.27 (RP-HPLC, CLOGP, calculated-S, Finizio et al. 1997) Bioconcentration Factor, log BCF: 1.79 (calculated-S, Kenaga 1980) 1.54 (calculated-KOC, Kenaga 1980) Sorption Partition Coefficient, log KOC: 2.80 (soil, Hamaker & Thompson 1972) 2.66 (soil, calculated-S as per Kenaga & Goring 1980, Kenaga 1980) 2.80 (reported as log KOM, Magee 1991) 2.65 (estimated as log KOM, Magee 1991) 2.63 (soil, 20–25°C, selected, Wauchope et al. 1992; Hornsby et al. 1996) 2.80 (Montgomery 1993) 2.63 (selected, Lohninger 1994) 2.80 (quoted or calculated-QSAR MCI 1., Sabljic et al. 1995) 2.48, 2.10 (soil, estimated-class-specific model, estimated-general model using molecular descriptors, Gramatica et al. 2000) Environmental Fate Rate Constants, k, or Half-Lives, t.: Biodegradation: in soil, microbial degradation t. = 2–3 wk (Tomlin 1994). Half-Lives in the Environment: Air: Surface water: t. = 11 d, at pH 4 and pH 10, t. = 12 d at pH 7 (40°C, Tomlin 1994). Ground water: Sediment: Soil: t. ~ 2 wk in moist loam soil at 21–27°C (Herbicide Handbook 1989; Montgomery 1993); selected field t. = 14 d (Wauchope et al. 1992; Hornsby et al. 1996); t. = 2–3 wk (Tomlin 1994);. Biota: © 2006 by Taylor & Francis Group, LLC 3620 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals 17.1.1.61 Pendimethalin Common Name: Pendimethalin Synonym: penoxalin Chemical Name: N-(1-ethylpropyl-3,4-dimethyl-2,6-dinitrobenzenamine CAS Registry No: 40487-42-1 Uses: herbicide Molecular Formula: C13H19N3O4 Molecular Weight: 281.308 Melting Point (°C): 56 (Lide 2003) Boiling Point (°C): 330 (Ashton & Crafts 1981; Herbicide Handbook 1989) decomposes on heating (Hartley & Kidd 1987; Tomlin 1994) Density (g/cm3 at 25°C): 1.19 (Ashton & Crafts 1981; Montgomery 19993; Tomlin 1994) 1.12 (Hartley & Kidd 1987) 1.17 (Herbicide Handbook 1989) Molar Volume (cm3/mol): Dissociation Constant pKa: Enthalpy of Fusion, .Hfus (kJ/mol): Entropy of Fusion, .Sfus (J/mol K): Fugacity Ratio at 25°C (assuming .Sfus = 56 J/mol K), F: 0.496 (mp at 56°C) Water Solubility (g/m3 or mg/L at 25°C or as indicated): 0.50 (23°C, Ashton & Crafts 1981) 0.30 (20°C, Hartley & Kidd 1987; Worthing & Walker 1987; Montgomery 1993; Tomlin 1994) 0.275 (Herbicide Handbook 1989) 0.275 (20–25°C, selected, Wauchope et al. 1992; Hornsby et al. 1996) 0.61 (20–25°C, Majewski & Capel 1995) Vapor Pressure (Pa at 25°C or as indicated): 0.004 (Ashton & Crafts 1981; Herbicide Handbook 1989) 0.004 (Hartley & Kidd 1987; Worthing & Walker 1987; Tomlin 1994) 1.25 . 10–3 (20–25°C, selected, Wauchope et al. 1992; Hornsby et al. 1996) 0.004 (Montgomery 1993) 8.16 . 10–3 (20–25°C, Majewski & Capel 1995) 0.00123; 0.00776 (liquid PL, GC-RT correlation; quoted lit., Donovan 1996) Henry’s Law Constant (Pa·m3/mol at 25°C or as indicated): 0.0867 (Montgomery 1993) 3.75 (20–25, calculated-P/C, Majewski & Capel 1995) Octanol/Water Partition Coefficient, log KOW: 5.18 (Montgomery 1993) 5.18 (Tomlin 1994) 5.24 (RP-HPLC-RT correlation using short ODP column, Donovan & Pescatore 2002) HN NO2 O2N © 2006 by Taylor & Francis Group, LLC Herbicides 3621 Octanol/Air Partition Coefficient, log KOA: Bioconcentration Factor, log BCF or log KB: Sorption Partition Coefficient, log KOC: 2.95 (soil, Wauchope et al. 1992; Hornsby et al. 1996) 4.20 (soil, Bottoni & Funari 1992) 4.14, 4.47 (loam, pH 7, pH 6.5, quoted, Montgomery 1993) 3.81 (sand, pH 7.6, Montgomery 1993) 4.07, 4.14 (sandy loam pH 6.4, silty loam, pH 7.0, Montgomery 1993) 1.48–2.93 (soil, Montgomery 1993) 3.70 (soil, Senseman et al. 1997) 3.14 (soil, estimated-general model using molecular descriptors, Gramatica et al. 2000) Environmental Fate Rate Constants, k, or Half-Lives, t.: Volatilization: Photolysis: slowly decomposed by light (Hartley & Kidd 1987; Tomlin 1994). Oxidation: Hydrolysis: t. < 21 d (Montgomery 1993). Biodegradation: observed t. = 33 d, 45 d, 52 d and 67 d in flooded and nonflooded conditions in nonsterile and sterile soils, respectively, in the study of degradation of pendimethalin under the influence of soil moisture and microbial activity in a sandy loam soil, in both nonsterile nonflooded and flooded soil, degradation followed first-order kinetics. (Kulshrestha & Singh 1992; quoted, Montgomery 1993). Biotransformation: Degradation by abiotic reductive transformations: k = 1.25 M–1 s–1 in H2S with (mecapto)juglone (hydroquinone moiety, an abiotic reductant found in natural systems) solution at pH 6.65 (Wang & Arnold 2003) Aqueous solutions with surface-bound Fe(II) species and their first-order rate constants as: k = 0.50 . 10–3 h–1 at pH 6.5, k = 0.27 . 10–2 h–1 at pH 7.0, k = 0.093 h–1 at pH 7.4, and k = 0.81 h–1 at pH 7.8 for aqueous ferrous ion system; k = 0.216 h–1 at pH 6.5, k = 0.274 h–1 at pH 6.7, k = 0.918 h–1 at pH 7.0, and k = 2.10 h–1 at pH 7.3 for Fe(II)/goethite system; k = 3.81 . 10–3 h–1 at pH 6.5, k = 2.66 . 10–3 h–1 at pH 7.0, k = 1.13 . 10–2 h–1 at pH 7.4 and k = 1.74 . 10–2 h–1 at pH 7.8 for Fe(II)/clay system, all with total dissolved Fe(II) = 1 mM (Wang & Arnold 2003) Bioconcentration, Uptake (k1) and Elimination (k2) Rate Constants: Half-Lives in the Environment: Air: Surface water: t. < 21 d in water (Tomlin 1994). Ground water: reported t. = 30–90 d (Bottoni & Funari 1992) Sediment: Soil: t. = 98 and 409 d at 30 and 10°C in a sandy loam soil with 75% moisture (Walker & Bond 1977) t. = 4 d on Bosket silt loam, t. = 6 d on Sharkey clay for the first 3 to 5 days when sprayed onto soil surface, rate of loss much slower for the remainder of the 7- or 12-d sampling period with t. = 18 d on Bosket silt loam, t. = 27 d on Sharkey clay (Savage & Jordon 1980) t. = 58–63 d in IARI sandy loam soil under Indian tropical climate (Kulshrestha & Yaduraju 1987) t. = 30–90 d or persistence (Bottoni & Funari 1992) t. = 66.9 d in sterile, t. = 52.2 d in nonsterile non-flooded sandy loam soil; t. = 44.9 d in sterile and 33.4 d in nonsterile flooded sandy loam soil in the study of degradation under the influence of soil moisture and microbial activity (Kulshrestha & Singh 1992; quoted, Montgomery 1993) reported field t. = 8–480 d, recommended t. = 90 d (Wauchope et al 1992; Hornsby et al. 1996); soil t. = 90 d (Senseman et al. 1997). Biota: t. = 3–4 months (quoted, Hartley & Kidd 1987; Tomlin 1994) © 2006 by Taylor & Francis Group, LLC 3622 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals 17.1.1.62 Picloram Common Name: Picloram Synonym: Amdon, ATCP, Borolin, Grazon, K-Pin, Tordon Chemical Name: 4-amino-3,5,6-trichloropicolinic acid; 4-amino-3,5,6-trichloro-2-pyridinecarboxylic acid Uses: systemic herbicide to control most broadleaf weeds on grassland and noncropland. CAS Registry No: 1918-02-1 Molecular Formula: C6H3Cl3N2O2 Molecular Weight: 241.459 Melting Point (°C): 218.5 (Lide 2003) Boiling Point (°C): Density (g/cm3 at 20°C): Molar Volume (cm3/mol): 204.2 (calculated-Le Bas method at normal boiling point, Suntio et al. 1988) Dissociation Constant pKa: 3.43, 3.42, 3.39, 3.36 (10, 20, 30. 40°C, Cheung & Biggar 1974) 1.90 (Weber et al. 1980; Willis & McDowell 1982) 3.60 (Windholz 1983; quoted, Howard 1991; Yao & Haag 1991; Haag & Yao 1992; Montgomery 1993) 2.3 (22°C, Worthing & Hance 1991; Montgomery 1993; Tomlin 1994) 1.94 (Hornsby et al. 1996) Enthalpy of Fusion, .Hfus (kJ/mol): Entropy of Fusion, .Sfus (J/mol K): Fugacity Ratio at 25°C (assuming .Sfus = 56 J/mol K), F: 0.0126 (mp at 218.5°C) Water Solubility (g/m3 or mg/L at 25°C or as indicated and reported temperature dependence equations. Additional data at other temperatures designated * are compiled at the end of this section): 430 (Bailey & White 1965; Freed 1966; Khan 1980; Weber et al. 1980; Ashton & Crafts 1981; Spencer 1982) 546* (20°C, shake flask-IR, measured range 10–40°C, pH 2.8, distilled water, Cheung & Biggar 1974) 73.65* (20°C, shake flask-IR, measured range 10–40°C at pH 0.2, Cheung & Biggar 1974) 62.7* (20°C, shake flask-IR, measured range 10v40°C at pH 1.1, Cheung & Biggar 1974) 137* (20°C, shake flask-IR, measured range 10–40°C at pH 2.0, Cheung & Biggar 1974) 19560* (20°C, shake flask-IR, measured range 10–40°C at pH 4.2, Cheung & Biggar 1974) 74593* (20°C, shake flask-IR, measured range 10–40°C at pH 4.7, Cheung & Biggar 1974) 430 (Martin & Worthing 1977, Worthing & Hance 1991; quoted, Kenaga 1980; Kenaga & Goring 1980; Isensee 1991; Howard 1991) 430 (Hartley & Graham-Bryce 1980; Taylor & Glotfelty 1988) 430 (Hartley & Kidd 1987; Herbicide Handbook 1989; Tomlin 1994; Milne 1995) 400–430 (Montgomery 1993) Vapor Pressure (Pa at 25°C or as indicated): 7.30 . 10–7 (20°C, Hartley & Graham-Bryce 1980) 8.20 . 10–5 (35°C, Khan 1980; Ashton & Crafts 1981; Hartley & Kidd 1987; Herbicide Handbook 1989) 8.26 . 10–5 (20–25°C, Weber et al. 1980; Willis & McDowell 1982) 9.70 . 10–9 (Dobbs & Cull 1982; quoted, Howard 1991) 7.30 . 10–6 (20°C, quoted from Hartlet & Graham-Bryce 1980, Dobbs et al. 1984) 6.00 . 10–5 (20°C, selected, Suntio et al. 1988) 1.40 . 10–4 (45°C, Herbicide Handbook 1989) N OH O Cl NH2 Cl Cl © 2006 by Taylor & Francis Group, LLC Herbicides 3623 4.50 . 10–8 (quoted, Nash 1989) 7.40 . 10–7 (20°C, selected, Taylor & Spencer 1990) 8.20 . 10–5 (35°C, Worthing & Hance 1991; Montgomery 1993; Tomlin 1994) Henry’s Law Constant (Pa m3/mol at 25°C or as indicated): 3.40 . 10–5 (20°C, calculated-P/C, Suntio et al. 1988; quoted, Mabury & Crosby 1996) 4.20 . 10–7 (calculated-P/C, Taylor & Glotfelty 1988) 2.50 . 10–5 (calculated-P/C, Nash 1989) 4.10 . 10–6 (calculated-P/C, Howard 1991) 3.40 . 10–5 (20–35°C, calculated-P/C, Montgomery 1993) 3.17 . 10–5 (calculated-P/C, this work) Octanol/Water Partition Coefficient, log KOW: 0.30 (Kenaga 1975) 0.63 (selected, Dao et al. 1983) 0.30 (Hansch & Leo 1985; Hansch et al. 1995;) –3.47 (selected, Gerstl & Helling 1987) 1.166 (calculated as per Broto et al. 1984, Karcher & Devillers 1990) 0.26, 0.30 (quoted, Sangster 1993) 1.87 (LOGPSTAR or CLOGP data, Sabljic et al. 1995) Bioconcentration Factor, log BCF: –1.70 (fish in static water, quoted from Dow Chemical data, Kenaga & Goring 1980) 1.30 (calculated-S, Kenaga 1980; quoted, Isensee 1991) –0.222 (calculated-KOC, Kenaga 1980) 0.0 (estimated-KOW, Lyman et al. 1982; quoted, Howard 1991) 1.49 (fish in flowing water, Garten & Trabalka 1983; quoted, Howard 1991) Sorption Partition Coefficient, log KOC: 1.23 (soil, Hamaker & Thompson 1972) 1.10 (average in soil, Hamaker & Thompson 1972) 1.10 (average in soil, Reinhold et al. 1979) 1.23 (Kenaga & Goring 1980; quoted, Bahnick & Doucette 1988) 2.20 (soil, calculated-S as per Kenaga & Goring 1980, Kenaga 1980) 1.41 (av. of 26 soils, Rao & Davidson 1980) 1.40 (soil, Rao & Davidson 1982) 1.31, 1.05, 1.34, 1.0, 1.26. 1.10, 1.05 (Catlin soil, Commerce soil, Fargo soil, Holdredge soil, Norfolk soil, Kawkawlin soil, Walla-Walla soil, McCall & Agin 1985; quoted, Brusseau & Rao 1989) 2.11 (calculated-MCI ., Gerstl & Helling 1987) 1.68 (screening model calculations, Jury et al. 1987b) 1.47 (calculated-MCI ., Bahnick & Doucette 1988) 1.88 (Nash 1989) 1.23 (reported as log KOM, Magee 1991) 1.20 (organic carbon, Wauchope et al. 1991) 1.11, 1.41, 1.68 (soil, quoted values, Bottoni & Funari 1992) 1.41 (Montgomery 1993) 1.30 (soil, calculated-QSAR MCI 1., Sabljic et al. 1995) 1.55, 1.39, 2.38 (soils: organic carbon OC . 0.1%, OC . 0.5%, 0.1 . OC < 0.5%, and pH 2.0–10.5, average, Delle Site 2001) 3.07, 2.96, 3.30 (soils: organic carbon OC . 0.1%, OC . 0.5%, 0.1 . OC < 0.5%, and pH . 2.0 undissociated, average, Delle Site 2001) 1.80, 1.76 (soils: organic carbon OC . 0.1%, OC . 0.5%, pH 4.2–5.9, average, Delle Site 2001) 1.12, 2.02, 1.93 (soils: organic carbon OC . 0.1%, OC . 0.5%, 0.1 . OC < 0.5%, pH . 6.0, dissociated, average, Delle Site 2001) © 2006 by Taylor & Francis Group, LLC 3624 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals Environmental Fate Rate Constants, k, or Half-Lives, t.: Volatilization: Photolysis: t. = 200 h for 40% of 4,840 µg/mL to degrade in dilute NaOH solution under sunlight (Hall et 1968; quoted, Cessna & Muir 1991); t. = 2.3 d to 9.58 d direct photolysis by sunlight under various conditions, at depths of 2.54 cm-3.65 m at various times of the year; one result at 3.65 m during Sept.-Oct. gave t. = 41.3 d; distilled water and canal water gave essentially the same results in one set of experiments (Hedlund & Youngson 1972; quoted, Cessna & Muir 1991; Howard 1991); t. = 72 h for 99% of 548 µg mL–1 to degrade in Na salt solution under 300–380 nm light (Mosier & Guenzi 1973; quoted, Cessna & Muir 1991); t. = 0.5 h for 38% of 265 µg mL–1 to degrade in distilled water under 254 nm light (Glass 1975; quoted, Cessna & Muir 1991); t. = 2.2 d for < 2.4 µg mL–1 L to degrade in distilled water under sunlight (Skurlatov et al. 1983; quoted, Cessna & Muir 1991); t. = 16 h in surface water estimated from direct midday sunlight photolysis in mid-summer at 40°N (Zepp 1991). Oxidation: photooxidation: t. = 12.21 d in air, based on estimated rate constant for the reaction with photochemically produced hydroxyl radical in the atmosphere (GEMS 1986; quoted, Howard 1991) k = 5.9 . 109 M–1 s–1 for the reaction (Fenton with reference to acetophenone) with hydroxyl radical in aqueous solutions at pH 2.1–3.7 and at 24 ± 1°C (Buxton et al. 1988; quoted, Haag & Yao 1992) k(aq.) = (50–150) M–1 s–1 for direct reaction with ozone in water at pH 1.5–4.9 and 21 ± 1°C, with t. = 4.0 min at pH 7 (Yao & Haag 1991). k(aq.) = (3.4 ± 0.3) . 109 M–1 s–1 for the reaction (Fenton with reference to acetophenone) with hydroxyl radicals in aqueous solutions at pH 2.1–3.7 and at 24 ± 1°C (Haag & Yao 1992) k(aq.) = 1.3 . 109 M–1 s–1 for reaction with hydroxyl radical, in irradiated field water both in the laboratory and sunlit rice paddies (Mabury & Crosby 1996). Hydrolysis: Biodegradation: t. = 128–144 h in mixture of 5 g soil and 1–4 mL water, t. = 90–1000 h in mixture of 1 mL water with 0.25–10 g soil, (Hance 1969; quoted, Howard 1991); t. > 15 months for 0.07, 0.72 and 10 µg mL–1 to biodegrade in groundwater (Weidner 1974; quoted, Muir 1991); k = 0.0073 d–1 by soil incubation die-away test studies (Rao & Davidson 1980; quoted, Scow 1982); biochemical t. = 100 d from screening model calculations (Jury et al. 1987b); t. = 30–300 d, degraded slowly by soil microorganisms (Tomlin 1994). Biotransformation: Bioconcentration, Uptake (k1) and Elimination (k2) Rate Constants: Half-Lives in the Environment: Air: t. = 12.21 d, based on estimated rate constant for the vapor-phase reaction with photochemically produced hydroxyl radicals in the atmosphere (GEMS 1986; quoted, Howard 1991). Surface water: t. = 2.6 d decomposed by UV irradiation (Tomlin 1994); measured rate constant k = (50 - 150) M–1 s–1 for direct reaction with ozone in water at pH 1.5–4.9 and 21°C, with t. = 4.0 min at pH 7 (Yao & Haag 1991). Ground water: t. > 15 months for 0.07, 0.72 and 10 µg/mL to biodegrade in ground water (Weidner 1974; quoted, Muir 1991); measured rate constant k . 0.005 M–1 s–1 for direct reaction with ozone in water at pH 2 and 21°C, with t. . 80 d at pH 7 (Yao & Haag 1991) reported t. = 30–330, 138, 180 and 206 d (Bottoni & Funari 1992). Sediment: Soil: estimated persistence of 18 months (Kearney et al. 1969; Edwards 1973; quoted, Morrill et al. 1982; Jury et al. 1987b); persistent in soils with t. > 5 yr (Alexander 1973; quoted, Howard 1991); estimated first-order t. = 95 d in soil from biodegradation rate constant k = 0.0073 d–1 by soil incubation die-away test studies (Rao & Davidson 1980; quoted, Scow 1982); © 2006 by Taylor & Francis Group, LLC Herbicides 3625 persistent in soil with t. > 100 d (Willis & McDowell 1982); t. = 100 d from screening model calculations (Jury et al. 1987b); selected t. = 90 d (Wauchope et al. 1991; quoted, Dowd et al. 1993); reported t. = 30–330 d, 18 d, 180 d and 206 d (Bottoni & Funari 1992); t. = 3–330 d (Tomlin 1994). Biota: biochemical t. = 100 d from screening model calculations (Jury et al. 1987b); average t. = 60 d in the forest (USDA 1989; quoted, Neary et al. 1993). TABLE 17.1.1.62.1 Reported aqueous solubilities of picloram at various temperatures Cheung & Biggar 1974 shake flask-IR spec. t/°C S/g·m–3 S/g·m–3 S/g·m–3 S/g·m–3 S/g·m–3 S/g·m–3 pH 0.20 pH 1.10 pH 2.0 pH 2.8 pH 4.2 pH 4.7 10 43.95 39.12 89.11 475 22240 84446 20 73.65 62.78 136.92 545.74 19560 74953 30 119.5 108.9 205.3 683.4 21395 82248 40 214.9 199 316.3 704.5 21371 78240 .Hsol/(kJ mol–1) 38.49 38.91 31.38 12.97 0 0 © 2006 by Taylor & Francis Group, LLC 3626 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals 17.1.1.63 Profluralin Common Name: Profluralin Synonym: CGA 10832, Pregard, Tolban Chemical Name: N-(cyclopropylmethyl)-2,6-dinitro-N-propyl-4-trifluoromethylaniline; N-(cyclopropylmethyl)- 2,6-dinitro-N-propyl-4-(trifluoromethyl) benzenamine Uses: herbicide for pre-planting by soil incorporation to control annual and perennial broadleaf and grass weeds in cotton, soybeans, brassicas, capsicums, tomatoes and other crops. CAS Registry No: 26399-36-0 Molecular Formula: C14H16F3N3O4 Molecular Weight: 347.290 Melting Point (°C): 34 (Lide 2003) Boiling Point (°C): Density (g/cm3 at 20°C): 1.45 (25°C, Ashton & Crafts 1981) 1.38 (Hartley & Kidd 1987; Worthing & Hance 1991) Molar Volume (cm3/mol): 304.7 (calculated-Le Bas method at normal boiling point) Dissociation Constant pKa: Enthalpy of Fusion, .Hfus (kJ/mol): Entropy of Fusion, .Sfus (J/mol K): Fugacity Ratio at 25°C (assuming .Sfus = 56 J/mol K), F: 0.816 (mp at 34°C) Water Solubility (g/m3 or mg/L at 25°C or as indicated): 0.10 (20°C, Weber 1972) 0.10 (Spencer 1973, 1982; Wauchope 1978; Kenaga 1980) 0.10 (27°C, Ashton & Crafts 1973, 1981) 0.10 (shake flask-HPLC, Ellgehausen et al. 1981) 0.10 (20°C, Hartley & Kidd 1987; Milne 1995) 0.10 (20°C, Worthing & Walker 1987, Worthing & Hance 1991) 0.10 (20–25°C, selected, Augustijn-Beckers et al. 1994; Hornsby et al. 1996) Vapor Pressure (Pa at 25°C or as indicated): 0.0092 (20°C, Weber 1972; Worthing & Walker 1987) 0.0092 (20°C, Ashton & Crafts 1973, 1981) 0.0084 (20°C, Hartley & Kidd 1987) 0.0084 (20°C, Worthing & Hance 1991) 0.0084 (20–25°C, selected, Augustijn-Beckers et al. 1994; Hornsby et al. 1996) Henry’s Law Constant (Pa·m3/mol at 25°C or as indicated): 39.07 (20°C, calculated-P/C, Suntio et al. 1988) 31.91 (20°C, calculated-P/C, Muir 1991) Octanol/Water Partition Coefficient, log KOW: 5.16 (selected, Dao et al. 1983) 6.34 (shake flask-HPLC/UV, Ellgehausen et al. 1981) 6.34 (recommended, Sangster 1993) NO2 F F F O2N N © 2006 by Taylor & Francis Group, LLC Herbicides 3627 4.46 (calculated-fragment const., Pinsuwan et al. 1995) 6.34 (recommended, Hansch et al. 1995) 5.08 (LOGPSTAR or CLOGP data, Sabljic et al. 1995) Bioconcentration Factor, log BCF: 3.35 (calculated-S, Kenaga 1980; quoted, Isensee 1991) 2.83 (calculated-KOC, Kenaga 1980) Sorption Partition Coefficient, log KOC: 3.93 (soil, exptl., Kenaga 1980) 4.19 (soil, calculated-S as per Kenaga & Goring 1980, Kenaga 1980) 3.83 (estimated as log KOM, Magee 1991) 3.93 (soil, quoted exptl., Meylan et al. 1992) 4.26 (soil, calculated-MCI . and fragment contribution, Meylan et al. 1992) 4.00 (20–25°C, estimated, Augustijn-Beckers et al. 1994; Hornsby et al. 1996) 4.16 (selected, Lohninger 1994) 4.01 (soil, calculated-QSAR MCI 1., Sabljic et al. 1995) 3.87 (soil, estimated-general model using molecular descriptors, Gramatica et al. 2000) Environmental Fate Rate Constants, k, or Half-Lives, t.: Volatilization: estimated t. ~ 1.2 d from 1 m depth of water at 20°C (Muir 1991). Photolysis: Oxidation: Hydrolysis: Biodegradation: t. = 12 d for 0.5 µg mL–1 to biodegrade in flooded soils at 20–42°C (Savage 1978; quoted, Muir 1991); Degradation t. < 1 month in three soils, Goldsborol loamy sand, Cecil loamy sand Drummer clay loam treated with 1 ppm profluralin) for 4 month under aerobic conditions, no degradation in sterile controls. (shake flask-TLC, Camper et al. 1980) t. < 1 month for 1 µg/mL to biodegrade in flooded soils at 25°C (derived from results of Camper et al. 1980, Muir 1991); biodegradation t. < 20 d in water and sediment with flooded soils and terrestrial-aquatic model ecosystems (Miur 1991). Biotransformation: Bioconcentration, Uptake (k1) and Elimination (k2) Rate Constants: Half-Lives in the Environment: Air: Surface water: biodegradation t. < 20 d in water and sediment with flooded soils and terrestrial-aquatic model ecosystems (Muir 1991). Ground water: Sediment: biodegradation t. < 20 d in water and sediment with flooded soils and terrestrial-aquatic model ecosystems (Muir 1991). Soil: t. = 12 d for 0.5 µg mL–1 to biodegrade in flooded soils at 20–42°C (Savage 1978, Muir 1991) persistence of 12 months in soil (Wauchope 1978); aerobic and anaerobic degradation t. < 1 month in 3 flooded soils at 25°C (Camper et al. 1980); field studies, t. = 10.9 wk - 1978 first study; t. = 10.1 wk -1978 second study; t. = 11.5 wk -1979, in a Crowley silt loam at Stuttgart, Arkansas (Brewer et al. 1982) laboratory studies: t. = 19.9 wk at 4°C, t. = 6.7 wk at 25°C for soil of field capacity moisture (27% w/w for Crowley silt loam), t. = 20.4 wk at 4°C, t. = 4.8 wk at 25°C for flooded soils, Crowley silt loam; and t. = 25.8 wk at 4°C, t. = 8.6 wk at 25°C for soil of field capacity moisture (34% w/w for Sharkey silty clay), t. = 21.3 wk at 4°C and t. = 6.2 wk at 25°C for flooded soils, Sharkey silty clay (Brewer et al. 1982); selected field t. = 110 d (Augustijn-Beckers et al. 1994; Hornsby et al. 1996). Biota: © 2006 by Taylor & Francis Group, LLC 3628 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals 17.1.1.64 Prometon Common Name: Prometon Synonym: G 31435, Gesafram, Gesagram, Methoxypropazine, Ontracic 800, Ontrack, Pramitol, Prometone Chemical Name: 6-methoxy-N,N.-bis(methylethyl)-1,3,5-triazine-2,4-diamine; 2,4-bis(isopropylamino)-6-methoxy- 1,3,5-triazine Uses: nonselective pre-emergence and post-emergence herbicide to control most annual and broadleaf weeds, grasses, and brush weeds on noncropland. CAS Registry No: 1610-18-0 Molecular Formula: C10H19N5O Molecular Weight: 225.291 Melting Point (°C): 91.5 (Lide 2003) Boiling Point (°C): Density (g/cm3 at 20°C): 1.088 (Hartley & Kidd 1987; Worthing & Hance 1991; Montgomery 1993) Molar Volume (cm3/mol): 280.2 (calculated-Le Bas method at normal boiling point) Dissociation Constant: 4.28 (pKa, Weber 1970; quoted, Bintein & Devillers 1994) 4.30 (pKa, 21°C, Worthing & Hance 1991; Montgomery 1993) 9.73 (pKb, Wauchope et al. 1992; Hornsby et al. 1996) 9.7 (21°C, pKb, Tomlin 1994) Enthalpy of Vaporization, .HV (kJ/mol): 90.77 (Rordorf 1989) Enthalpy of Fusion, .Hfus (kJ/mol): 22.175 (DSC method, Plato & Glasgow 1969) 21.6 (Rordorf 1989) Entropy of Fusion, .Sfus (J/mol K): Fugacity Ratio at 25°C (assuming .Sfus = 56 J/mol K), F: 0.223 (mp at 91.5°C) Water Solubility (g/m3 or mg/L at 25°C or as indicated): 750 (20°C, Bailey & White 1965; Ashton & Crafts 1981; Herbicide Handbook 1989) 1000, 678, 669 (26°C, pH 3.0, 7.0, 10.0, shake flask-UV, Ward & Weber 1968) 750 (Martin & Worthing 1977; Herbicide Handbook 1978) 677 (Weber et al. 1980) 620 (20°C, Spencer 1982) 750 (20°C, Verschueren 1983) 750 (20°C, Hartley & Kidd 1987; Montgomery 1993) 620 (20°C, Worthing & Walker 1987, 1991; Tomlin 1994) 720 (20–25°C, selected, Wauchope et al. 1992; Hornsby et al. 1996) Vapor Pressure (Pa at 25°C or as indicated and reported temperature dependence equations.): 3.07 . 10–4 (20°C, extrapolated-Antoine eq. from gas saturation-GC measurements, measured range 50–130°C, Friedrich & Stammbach 1964) (See figure at the end of this section.) log (P/mmHg) = 11.911 – 4933/(T/K), temp range 50–130°C (gas saturation-GC, data presented in Antoine eq., Friedrich & Stammbach 1964) N N N HN NH O © 2006 by Taylor & Francis Group, LLC Herbicides 3629 0.00030 (20°C, Khan 1980) 0.00031 (20°C, Ashton & Crafts 1981; Worthing & Hance 1991) 0.00083 (Jury et al. 1984; selected, Spencer et al. 1988; Spencer & Cliath 1990; Taylor & Spencer 1990) 0.00031 (20°C, Hartley & Kidd 1987) 0.00031, 0.00105 (20°C, 30°C, Herbicide Handbook 1989) 1.0 . 10–3, 3.30 . 10–2, 0.65, 8.60, 82 (25, 50, 70, 100, 125°C, gas saturation-GC, Rordorf 1989) log (PS/Pa) = 16.525 – 5817.4/(T/K); measured range 32.1–89.3°C (gas saturation-GC, Rordorf 1989) log (PL/Pa) = 13.617 – 4741.7/(T/K); measured range 92.3–140°C (gas saturation-GC, Rordorf 1989) 0.00103 (20–25°C, selected, Wauchope et al. 1992; Hornsby et al. 1996) 0.00031 (20°C, Montgomery 1993) 0.000306 (20°C, Tomlin 1994) Henry’s Law Constant (Pa·m3/mol at 25°C or as indicated): 2.50 . 10–4 (calculated-P/C, Jury et al. 1984; Spencer et al. 1988; Spencer & Cliath 1990) 9.02 . 10–5 (20°C, calculated-P/C, Montgomery 1993) 9.01 . 10–5 (calculated-P/C, this work) Octanol/Water Partition Coefficient, log KOW: 1.94 (selected, Dao et al. 1983) 1.94 (Gerstl & Helling 1987) 2.99 (RP-HPLC-RT correlation, Finizio et al. 1991; quoted, Sangster 1993) 2.85 (selected, Magee 1991) 2.55 (shake flask-UV, Liu & Qian 1995) 2.69, 2.99 (Montgomery 1993) 2.99 (recommended, Hansch et al. 1995) 2.82 (RP-HPLC-RT correlation, Finizio et al. 1997) Bioconcentration Factor, log BCF: 1.18 (calculated-S, Kenaga 1980; quoted, Isensee 1991) 1.28 (calculated-KOC, Kenaga 1980) Sorption Partition Coefficient, log KOC: 2.54 (soil, Hamaker & Thompson 1972; Kenaga 1980; Kenaga & Goring 1980) 2.04 (soil, calculated-S as per Kenaga & Goring 1980, Kenaga 1980) 2.61 (Jury et al. 1984; quoted, Spencer & Cliath 1990) 2.40 (calculated-MCI ., Gerstl & Helling) 2.48 (Spencer et al. 1988) 2.35 (estimated as log KOM, Magee 1991) 2.20 (soil, calculated-MCI . and fragment contribution, Meylan et al. 1992) 2.18 (soil, 20–25°C, selected, Wauchope et al. 1992; Hornsby et al. 1996) 1.92–2.24 (Montgomery 1993) 2.77 (selected, Lohninger 1994) 2.39 (calculated-KOW, Liu & Qian 1995) 2.50 (soil, calculated-MCI 1., Sabljic et al. 1995) 2.60; 2.70, 2.68 (soil, quoted obs.; estimated-class-specific model, estimated-general model using molecular descriptors, Gramatica et al. 2000) 2.47, 2.50 (soils: organic carbon OC . 0.1%, OC . 0.5%, pH 4.3–7.1, average, Delle Site 2001) 2.81, 2.65, 2.53 (soils with organic carbon OC . 0.5% at: pH 4.3–4.9, pH 5.0–5.9, pH- 6.0, average, Delle Site 2001) Environmental Fate Rate Constants, or Half-Lives, t.: Volatilization: estimated t. ~ 100 d (Spencer & Cliath 1990). Photolysis: t. = 2.25 h for 1% of 100 µg mL–1 to degrade in distilled water under 300 nm light (Tanaka et al. 1981; quoted, Cessna & Muir 1991). Oxidation: © 2006 by Taylor & Francis Group, LLC 3630 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals Hydrolysis: Biodegradation: Biotransformation: Bioconcentration, Uptake (k1) and Elimination (k2) Rate Constants: Half-Lives in the Environment: Soil: selected field t. = 500 d (Wauchope et al. 1992; Hornsby et al. 1996). FIGURE 17.1.1.64.1 Logarithm of vapor pressure versus reciprocal temperature for prometon. Prometon: vapor pressure vs. 1/T -5.0 -4.0 -3.0 -2.0 -1.0 0.0 1.0 2.0 3.0 0.0022 0.0024 0.0026 0.0028 0.003 0.0032 0.0034 0.0036 1/(T/K) P( gol S ) aP/ Friedrich & Stammbach 1964 (50 to 130 °C) Friedrich & Stammbach 1964 (extrapolated) m.p. = 91.5 °C © 2006 by Taylor & Francis Group, LLC Herbicides 3631 17.1.1.65 Prometryn Common Name: Prometryn Synonym: Caparol, Cotton-Pro, Gesagard, G-34161, Mercasin, Mercazin, Polisin, Primatol, Prometrex, Prometrin, Selectin, Sesagard, Uvon Chemical Name: N,N.-bis(1-methylethyl)-6-(methylthio)-1,3,5-triazine-2,4-diamine; 2,4-bis(isopropylamino)-6-(methylthio)- 1,3,5-triazine Uses: selective herbicide to control many annual grass and broadleaf weeds in celery, cotton and peas. CAS Registry No: 7287-19-6 Molecular Formula: C10H19N5S Molecular Weight: 241.357 Melting Point (°C): 119 (Lide 2003) Boiling Point (°C): Density (g/cm3 at 20°C): 1.157 (Hartley & Kidd 1987; Worthing & Hance 1991; Montgomery 1993; Milne 1995) Molar Volume (cm3/mol): 299.7 (calculated-Le Bas method at normal boiling point) Dissociation Constant: 4.05 (pKa, Weber 1970; Pacakova et al. 1988; Somasundaram et al. 1991; Bintein & Devillers 1994) 4.10 (pKa, 21°C, Weber et al. 1980; Willis & McDowell 1982; Worthing & Hance 1991) 9.95 (pKb, Wauchope et al. 1992; Hornsby et al. 1996) 4.05 (pKa, 21°C, Montgomery 1993) Enthalpy of Vaporization, .HV (kJ/mol): 96.43 (Rordorf 1989) Enthalpy of Fusion, .Hfus (kJ/mol): 26.36 (DSC method, Plato & Glasgow 1969) 25.4 (Rordorf 1989) Entropy of Fusion, .Sfus (J/mol K): Fugacity Ratio at 25°C (assuming .Sfus = 56 J/mol K), F: 0.120 (mp at 119°C) Water Solubility (g/m3 or mg/L at 25°C or as indicated): 48 (20°C, Woodford & Evans 1963) 48 (20°C, Bailey & White 1965; Ashton & Crafts 1973, 1981; Khan 1980) 206, 40.3, 41.8 (26°C, shake flask-UV at pH 3.0, 7.0, 10.0, Ward & Weber 1968) 48 (Martin & Worthing 1977; Herbicide Handbook 1978) 40 (Weber et al. 1980) 48 (20°C, Hartley & Kidd 1987; Herbicide Handbook 1989; Montgomery 1993; Milne 1995) 33 (20°C, Worthing & Walker 1987, Worthing & Hance 1991) 33 (20–25°C, selected, Wauchope et al. 1992; Hornsby et al. 1996) 33 (Tomlin 1994; selected, Lohninger 1994) 241 (calculated-group contribution method, Kuhne et al. 1995) Vapor Pressure (Pa at 25°C or as indicated and reported temperature dependence equations.): 1.33 . 10–4 (20°C, extrapolated-Antoine eq. from gas saturation-GC measurements, measured range 50–130°C, Friedrich & Stammbach 1964) (See figure at the end of this section.) log (P/mmHg) = 11.911 – 4933/(T/K), temp range 50–130°C (gas saturation-GC, data presented in Antoine eq., Friedrich & Stammbach 1964) N N N HN NH S © 2006 by Taylor & Francis Group, LLC 3632 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals 0.00028 (from Friedrich & Stammbach 1964; Jury et al. 1983; 1984; Spencer & Cliath 1990) 0.00013 (20°C, Ashton & Crafts 1973, 1981) 0.00013 (20–25°C, Weber et al. 1980) 0.00028 (quoted, Jury et al. 1984; Spencer & Cliath 1990) 0.00013 (20°C, Hartley & Kidd 1987; Worthing & Hance 1991; Montgomery 1993) 0.00010 (20°C, selected, Suntio et al. 1988) 0.00013, 0.00053 (20, 30°C, Herbicide Handbook 1989) 1.60 . 10–4, 6.70 . 10–3, 0.16, 2.50, 28.0 (25, 50, 70, 100, 125°C, gas saturation-GC, Rordorf 1989) log (PS/Pa) = 17.063 – 6215.6/(T/K); measured range 32.4–117°C (gas saturation-GC, Rordorf 1989) log (PL/Pa) = 14.013 – 5037.2/(T/K); measured range 129–140°C (gas saturation-GC, Rordorf 1989) 0.00017 (20–25°C, selected, Wauchope et al. 1992; Hornsby et al. 1996) 0.000169 (Tomlin 1994) Henry’s Law Constant (Pa·m3/mol at 25°C or as indicated): 0.00139 (calculated-P/C, Jury et al. 1984; quoted, Spencer & Cliath 1990) 0.00139 (calculated-P/C, Jury et al. 1987a,b; Jury & Ghodrati 1989) 0.00050 (20°C, calculated-P/C, Suntio et al. 1988; quoted, Majewski & Capel 1995) 0.00050 (20°C, calculated-P/C, Montgomery 1993) Octanol/Water Partition Coefficient, log KOW: 2.99 (selected, Dao et al. 1983) 1.91 (RP-HPLC-k. correlation, Braumann et al. 1983) 3.46 (selected, Yoshioka et al. 1986) 3.51 (shake flask, Mitsutake et al. 1986) 2.99 (Gerstl & Helling 1987) 3.34 (RP-HPLC-RT correlation, Finizio et al. 1991) 3.43 (selected, Magee 1991) 3.34 (Worthing & Hance 1991; Milne 1995) 3.34, 3.46 (Montgomery 1993) 3.51 (recommended, Sangster 1993) 2.93 (RP-HPLC-k. correlation, Liu & Qian 1995) 3.51 (recommended, Hansch et al. 1995) 3.35 (Pomona-database, Muller & Kordel 1996) 3.25 (RP-HPLC-RT correlation, Finizio et al. 1997) 2.99 (RP-HPLC-RT correlation using short ODP column, Donovan & Pescatore 2002) Bioconcentration Factor, log BCF: 1.85, 1.67 (calculated-S, KOC, Kenaga 1980) Sorption Partition Coefficient, log KOC: 2.91 (soil, Hamaker & Thompson 1972; Kenaga 1980; Kenaga & Goring 1980) 2.72 (soil, calculated-S as per Kenaga & Goring 1980, Kenaga 1980) 2.79 (Rao & Davidson 1980) 3.17 (calculated-MCI ., Gerstl & Helling) 2.78 (screening model calculations, Jury et al. 1987a,b; Jury & Ghodrati 1989) 2.75 (estimated as log KOM, Magee 1991) 2.72–2.91, 2.79, 2.83 (soil, quoted values, Bottoni & Funari 1992) 2.60 (soil, 20–25°C, selected, Wauchope et al. 1992; Hornsby et al. 1996) 2.38 (soil, HPLC-screening method, mean value from different stationary and mobile phases, Kordel et al. 1993, 1995b) 2.28–2.79 (Montgomery 1993) 3.15 (estimated-chemical structure, Lohninger 1994) 2.60 (soil, Tomlin 1994) 2.63 (calculated-KOW, Liu & Qian 1995) 2.85 (soil, calculated-QSAR MCI 1., Sabljic et al. 1995) © 2006 by Taylor & Francis Group, LLC Herbicides 3633 2.38; 2.84 (HPLC-screening method; calculated-PCKOC fragment method, Muller & Kordel 1996) 3.54, 1.595, 1.968, 1.77, 2.67 (first generation Eurosoils ES-1, ES-2, ES-3, ES-4, ES-5, shake flask/batch equilibrium-HPLC/UV, Gawlik et al. 1998) 3.24, 2.16, 2.86, 2.59, 2.53 (calculated-KOW; HPLC-screening method with different LC-columns, Szabo et al. 1999) 2.544, 2.635, 2.484, 1.816, 2.933 (second generation Eurosoils ES-1, ES-2, ES-3, ES-4, ES-5, shake flask/batch equilibrium-HPLC/UV and HPLC-k. correlation, Gawlik et al. 2000) 2.85, 2.89 (soil, estimated-class-specific model, estimated-general model using molecular descriptors, Gramatica et al. 2000) Environmental Fate Rate Constants, k, or Half-Lives, t.: Volatilization: t. = 60 d (Jury et al. 1984). Photolysis: Oxidation: Hydrolysis: t. = 22 d in 0.1 N hydrochloric acid solution, t. = 500 yr at pH 7 in distilled water and t. = 30 yr in 0.01 sodium hydroxide solution all at 25°C (Montgomery 1993). Biodegradation: t. = 60 d (Wauchope 1978); t. = 60 d for a 100 d leaching and screening test in 0–10 cm depth of soil (Jury et al. 1987a,b; Jury & Ghodrati 1989); soil microbial degradation t. = 70 d (Tomlin 1994). Biotransformation: Bioconcentration, Uptake (k1) and Elimination (k2) Rate Constants: Half-Lives in the Environment: Air: Surface water: completely decomposed when exposed to UV light for 3 h (Montgomery 1993). Ground water: reported half-lives or persistence, t. = 40–70, 60 and 94 d (Bottoni & Funari 1992) Sediment: Soil: estimated persistence of 3 months (Kearney et al. 1969; Edwards 1973; quoted, Morrill et al. 1982; Jury et al. 1987a,b; Jury & Ghodrati 1989); t. ~ 6 months to biodegrade in flooded soils (Plimmer et al. 1970; quoted, Muir 1991); persistence of 2 months in soil (Wauchope 1978); reported t. = 40–70 d, 60 d and 94 d (Bottoni & Funari 1992); selected field t. = 60 d (Wauchope et al. 1992; Hornsby et al. 1996); t. = 70 d for microbial degradation in soil (Tomlin 1994). Biota: biochemical t. = 60 d from screening model calculations (Jury et al. 1987a,b; Jury & Ghodrati 1989). FIGURE 17.1.1.65.1 Logarithm of vapor pressure versus reciprocal temperature for prometryn. Prometryn: vapor pressure vs. 1/T -5.0 -4.0 -3.0 -2.0 -1.0 0.0 1.0 2.0 3.0 0.0022 0.0024 0.0026 0.0028 0.003 0.0032 0.0034 0.0036 1/(T/K) P( gol S ) aP/ Friedrich & Stammbach 1964 (50 to 130 °C) Friedrich & Stammbach 1964 (extrapolated) m.p. = 119 °C © 2006 by Taylor & Francis Group, LLC 3634 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals 17.1.1.66 Pronamide Common Name: Pronamide Synonym: Kerb, Promamide, Propyzamide, RH-315 Chemical Name: 3,5-dichloro-N-(1,1-dimethylpropynyl)benzamide Uses: herbicide. CAS Registry No: 23950-58-5 Molecular Formula: C12H11Cl2NO Molecular Weight: 256.127 Melting Point (°C): 155 (Lide 2003) Boiling Point (°C): 321 Density (g/cm3 at 20°C): Molar Volume (cm3/mol): 270.4 (calculated-Le Bas method at normal boiling point) Dissociation Constant pKa: Enthalpy of Fusion, .Hfus (kJ/mol): Entropy of Fusion, .Sfus (J/mol K): Fugacity Ratio at 25°C (assuming .Sfus = 56 J/mol K), F: 0.0530 (mp at 155°C) Water Solubility (g/m3 or mg/L at 25°C or as indicated): 15 (Martin & Worthing 1977; Herbicide Handbook 1978, 1983; Worthing & Walker 1987) 15 (15°C, Khan 1980) 15 (Ashton & Crafts 1981) 15 (24°C, Herbicide Handbook 1989) 15 (20–25°C, selected, Wauchope et al. 1992; Hornsby et al. 1996) 15 (Tomlin 1994; Milne 1995) Vapor Pressure (Pa at 25°C or as indicated): 0.0113 (Khan 1980) 0.0113 (Ashton & Crafts 1981; Herbicide Handbook 1989) 0.0536 (Dixon & Rissman 1985; quoted, Howard 1991) 0.227 (Worthing & Walker 1987) 0.0113 (20–25°C, selected, Wauchope et al. 1992; Hornsby et al. 1996) 0.000058 (Tomlin 1994) Henry’s Law Constant (Pa·m3/mol at 25°C): 0.912 (Dixon & Rissman 1985) 0.193 (calculated-P/C as per Worthing & Walker 1987, Majewski & Capel 1995) 0.188 (calculated-P/C, this work) Octanol/Water Partition Coefficient, log KOW: 3.26 (estimated, Lyman et al. 1982; quoted, Howard 1991) 3.36 (selected, Magee 1991) 3.26 (selected, Dao et al. 1983) 2.95 (estimated-QSAR and SPARC, Kollig et al. 1993) 3.09–3.28 (Tomlin 1994; Milne 1995) 3.87 (LOGPSTAR or CLOGP data, Sabljic et al. 1995) Cl Cl O HN © 2006 by Taylor & Francis Group, LLC Herbicides 3635 Bioconcentration Factor, log BCF: 2.13 (calculated-S, Kenaga 1980) 1.00 (calculated-KOC, Kenaga 1980) 2.25 (estimated-KOW, Lyman et al. 1982; quoted, Howard 1991) 2.13 (estimated-S, Lyman et al. 1982; quoted, Howard 1991) Sorption Partition Coefficient, log KOC: 2.30 (soil, Leistra et al. 1974; Carlson et al.) 2.30 (measured for single soil, Kenaga 1980) 3.00 (soil, calculated-S as per Kenaga & Goring 1980, Kenaga 1980) 2.99 (soil, estimated-S, Lyman et al. 1982; quoted, Howard 1991) 2.30; 2.42 (reported as log KOM, estimated as log KOM, Magee 1991) 2.30; 3.20 (soil, quoted; calculated-MCI . and fragment contribution, Meylan et al. 1992) 2.90 (soil, 20–25°C, selected, Wauchope et al. 1992; Hornsby et al. 1996) 2.63 (estimated-QSAR and SPARC, Kollig 1993) 2.54 (selected, Lohninger 1994) 2.31 (soil, calculated-QSAR MCI 1., Sabljic et al. 1995) Environmental Fate Rate Constants, k, or Half-Lives, t.: Volatilization: based on a Henry’s law constant of 0.9118 Pa·m3/mol, t. ~ 6.6 d from a river 1-m deep flowing 1 m/s with a wind velocity of 3 m/s (estimated, Lyman et al. 1982; quoted, Howard 1991). Photolysis: degraded photolytically on soil thin films, t. = 13–57 d in artificial sunlight (Tomlin 1994). Oxidation: photooxidation t. = 4.2 h in air, based on an estimated rate constant for the vapor-phase reaction with photochemically produced hydroxyl radicals in the atmosphere (Atkinson 1985; quoted, Howard 1991). Hydrolysis: neutral hydrolysis rate constant k < 1.5 . 10–5 h–1 with a calculated t. > 700 d in neutral solution and with faster hydrolysis rates in acidic and basic solutions to be expected (Ellington et al. 1987, 1988; quoted, Howard 1991). Biodegradation: depending on soil and climatic conditions, the degradation t. = 10 to 112 d, but a t. = 40 d may be more common under field conditions (Walker 1976,78; Zandvoort et al. 1979; quoted, Howard 1991). Biotransformation: second-order rate constant k = 5 . 10–14 L/organisms·h with an estimated t. ~ 580 d for microbial degradation in natural water (Steen & Collette 1989; quoted, Howard 1991). Bioconcentration, Uptake (k1) and Elimination (k2) Rate Constants: Half-Lives in the Environment: Air: t. = 4.2 h, based on an estimated rate constant for the vapor-phase reaction with photochemically produced hydroxyl radicals in the atmosphere (Atkinson 1985; quoted, Howard 1991). Surface water: Ground water: Sediment: Soil: depending on soil and climatic conditions, the degradation t. = 10 to 112 d, but a t. = 40 d may be more common under field conditions (Walker 1976, 1978; Zandvoort et al. 1979; quoted, Howard 1991); selected field t. = 60 d (Wauchope et al. 1992; Hornsby et al. 1996); degraded photolytically on soil thin films, t. = 13–57 d in artificial sunlight (Tomlin 1994). Biota: © 2006 by Taylor & Francis Group, LLC 3636 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals 17.1.1.67 Propachlor Common Name: Propachlor Synonym: Albrass, Bexton, CIPA, CP 31393, Niticid, Propachlore, Prolex, Ramrod, Satecid Chemical Name: 2-chloro-N-(1-methylethyl)-N-phenylacetamide; 2-chloro-N-isopropyl-acetanilide Uses: selective pre-emergence herbicide to control most annual grasses and some broadleaf weeds in brassicas, corn, cotton, flax, leeks, maize, milo, onions, peas, roses, ornamental trees and shrubs, soybeans, and sugar cane. CAS Registry No: 1918-16-7 Molecular Formula: C11H14ClNO Molecular Weight: 211.688 Melting Point (°C): 77 (Herbicide Handbook 1989; Worthing & Hance 1991; Tomlin 1994; Milne 1995; Lide 2003) Boiling Point (°C): 110 (at 0.03 mmHg, Ashton & Crafts 1981; Hartley & Kidd 1987; Herbicide Handbook 1989; Worthing & Hance 1991; Montgomery 1993; Milne 1995) Density (g/cm3 at 20°C): 1.13 (25°C, Ashton & Crafts 1981) 1.242 (25°C, Hartley & Kidd 1987; Worthing & Hance 1991; Montgomery 1993; Tomlin 1994; Milne 1995) 1.134 (25°C, Herbicide Handbook 1989) Molar Volume (cm3/mol): 231.6 (calculated-Le Bas method at normal boiling point) Dissociation Constant pKa: Enthalpy of Fusion, .Hfus (kJ/mol): 27.614 (DSC method, Plato 1972) Entropy of Fusion, .Sfus (J/mol K): Fugacity Ratio at 25°C (assuming .Sfus = 56 J/mol K), F: 0.309 (mp at 77°C) Water Solubility (g/m3 or mg/L at 25°C or as indicated): 700 (Melnikov 1971; Khan 1980) 614 (20°C, Weber 1972) 693 (Spencer 1973, 1982) 580 (20°C, Ashton & Crafts 1973) 580 (Martin & Worthing 1977; Herbicide Handbook 1978) 839 (generator column-HPLC-RI, Swann et al. 1983) 2300 (HPLC-RT correlation, Swann et al. 1983) 613 (Hartley & Kidd 1987; Worthing & Walker 1987, Herbicide Handbook 1989 Worthing & Hance 1991; Tomlin 1994; Milne 1995) 613 (20–25°C, selected, Wauchope et al. 1992; Hornsby et al. 1996) 613–700 (Montgomery 1993) Vapor Pressure (Pa at 25°C or as indicated): 0.032 (20–25°C, Weber et al. 1980) 0.0307 (24°C, Beestman & Demming 1974) 0.0307 (Ashton & Crafts 1981; Herbicide Handbook 1989) 0.03 (Hartley & Kidd 1987) 0.03 (20°C, selected, Suntio et al. 1988) 0.0306 (Worthing & Hanc