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 10987654321 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. Reprinted material is quoted with permission, and sources are indicated. A wide variety of references are listed. Reasonable efforts have been made to publish reliable data and information, but the author and the publisher cannot assume responsibility for the validity of all materials or for the consequences of their use. No part of this book may be reprinted, reproduced, transmitted, or utilized in any form by any electronic, mechanical, or other means, now known or hereafter invented, including photocopying, microfilming, and recording, or in any information storage or retrieval system, without written permission from the publishers. For permission to photocopy or use material electronically from this work, please access www.copyright.com (http://www.copyright.com/) or contact the Copyright Clearance Center, Inc. (CCC) 222 Rosewood Drive, Danvers, MA 01923, 978-750-8400. CCC is a not-for-profit organization that provides licenses and registration for a variety of users. 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 chemical- to-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 commer- cialization 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 2259 10 Ethers CONTENTS 10.1 List of Chemicals and Data Compilations . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2262 10.1.1 Aliphatic ethers . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2262 10.1.1.1 Dimethyl ether (Methyl ether) . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2262 10.1.1.2 Diethyl ether (Ethyl ether) . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2266 10.1.1.3 Methyl t-butyl ether (MTBE) . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2271 10.1.1.4 Di-n-propyl ether . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2276 10.1.1.5 Di-isopropyl ether . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2280 10.1.1.6 Butyl ethyl ether . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2285 10.1.1.7 Di-n-butyl ether . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2289 10.1.1.8 1,2-Propylene oxide . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2293 10.1.1.9 Furan . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2297 10.1.1.10 2-Methylfuran . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2301 10.1.1.11 Tetrahydrofuran . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2303 10.1.1.12 Tetrahydropyran . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2307 10.1.1.13 1,4-Dioxane . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2309 10.1.2 Halogenated ethers . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2313 10.1.2.1 Epichlorohydrin . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2313 10.1.2.2 Chloromethyl methyl ether . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2315 10.1.2.3 Bis(chloromethyl)ether . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2317 10.1.2.4 Bis(2-chloroethyl)ether . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2319 10.1.2.5 Bis(2-chloroisopropyl)ether . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2322 10.1.2.6 2-Chloroethyl vinyl ether . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2325 10.1.2.7 Bis(2-chloroethoxy)methane . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2327 10.1.3 Aromatic ethers . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2329 10.1.3.1 Anisole (Methoxybenzene) . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2329 10.1.3.2 2-Chloroanisole . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2334 10.1.3.3 3-Chloroanisole . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2335 10.1.3.4 4-Chloroanisole . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2336 10.1.3.5 2,3-Dichloroanisole . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2337 10.1.3.6 2,6-Dichloroanisole . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2338 10.1.3.7 2,3,4-Trichloroanisole . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2339 10.1.3.8 2,4,6-Trichloroanisole . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2340 10.1.3.9 2,3,4,5-Tetrachloroanisole . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2341 10.1.3.10 2,3,5,6-Tetrachloroanisole . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2342 10.1.3.11 Veratrole (1,2-Dimethoxybenzene) . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2343 10.1.3.12 4,5-Dichloroveratrole . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2345 10.1.3.13 3,4,5-Trichloroveratrole . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2346 10.1.3.14 Tetrachloroveratrole . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2347 10.1.3.15 Phenetole . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2348 10.1.3.16 Benzyl ethyl ether . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2351 © 2006 by Taylor & Francis Group, LLC © 2006 by Taylor & Francis Group, LLC 2260 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals 10.1.3.17 Styrene oxide . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2353 10.1.3.18 Diphenyl ether . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2355 10.1.4 Polychlorinated diphenyl ethers (PCDEs) . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2359 10.1.4.1 2-Chlorodiphenyl ether (PCDE-1) . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2359 10.1.4.2 4-Chlorodiphenyl ether . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2360 10.1.4.3 2,4-Dichlorodiphenyl ether (PCDE-8) . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2362 10.1.4.4 2,6-Dichlorodiphenyl ether (PCDE-10) . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2363 10.1.4.5 2,4,4′-Trichlorodiphenyl ether (PCDE-28) . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2364 10.1.4.6 2,4,5-Trichlorodiphenyl ether (PCDE-29) . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2365 10.1.4.7 2,4′,5-Trichlorodiphenyl ether (PCDE-31) . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2367 10.1.4.8 2,2′,4,4′-Tetrachlorodiphenyl ether (PCDE-47) . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2368 10.1.4.9 2,3′,4,4′-Tetrachlorodiphenyl ether (PCDE-66) . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2369 10.1.4.10 2,4,4′,5-Tetrachlorodiphenyl ether (PCDE-74) . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2370 10.1.4.11 3,3′,4,4′-Tetrachlorodiphenyl ether (PCDE-77) . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2371 10.1.4.12 2,2′,3,4,4′-Pentachlorodiphenyl ether (PCDE-85) . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2373 10.1.4.13 2,2′,4,4′,5-Pentachlorodiphenyl ether (PCDE-99) . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2374 10.1.4.14 2,2′,4,4′,6-Pentachlorodiphenyl ether (PCDE-100) . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2376 10.1.4.15 2,2′,4,5,5′-Pentachlorodiphenyl ether (PCDE-101) . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2378 10.1.4.16 2,3,3′,4,4′-Pentachlorodiphenyl ether (PCDE-105) . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2379 10.1.4.17 3,3′,4,4′,5-Pentachlorodiphenyl ether (PCDE-126) . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2380 10.1.4.18 2,2′,3,3′,4,4′-Hexachlorodiphenyl ether (PCDE-128) . . . . . . . . . . . . . . . . . . . . . . . . . . . 2381 10.1.4.19 2,2′,3,4,4′,5-Hexachlorodiphenyl ether (PCDE-137) . . . . . . . . . . . . . . . . . . . . . . . . . . . 2382 10.1.4.20 2,2′,3,4,4′,5′ -Hexachlorodiphenyl ether (PCDE-138) . . . . . . . . . . . . . . . . . . . . . . . . . . . 2384 10.1.4.21 2,2′,3,4,4′,6′-Hexachlorodiphenyl ether (PCDE-140) . . . . . . . . . . . . . . . . . . . . . . . . . . . 2385 10.1.4.22 2,2′,4,4′,5,5′-Hexachlorodiphenyl ether (PCDE-153) . . . . . . . . . . . . . . . . . . . . . . . . . . . 2386 10.1.4.23 2,2′,4,4′,5,6′-Hexachlorodiphenyl ether (PCDE-154) . . . . . . . . . . . . . . . . . . . . . . . . . . . 2388 10.1.4.24 2,3′,4,4′,5,5′-Hexachlorodiphenyl ether (PCDE-167) . . . . . . . . . . . . . . . . . . . . . . . . . . . 2390 10.1.4.25 2,2′,3,4,4′,5,5′-Heptachlorodiphenyl ether (PCDE-180) . . . . . . . . . . . . . . . . . . . . . . . . . 2392 10.1.4.26 2,2′,3,4,4′,5,6′-Heptachlorodiphenyl ether (PCDE-182) . . . . . . . . . . . . . . . . . . . . . . . . . 2394 10.1.4.27 2,2′,3,4,4′,6,6′-Heptachlorodiphenyl ether (PCDE-184) . . . . . . . . . . . . . . . . . . . . . . . . . 2395 10.1.4.28 2,2′,3,3′,4,4′,5,5′-Octachlorodiphenyl ether (PCDE-194) . . . . . . . . . . . . . . . . . . . . . . . . 2396 10.1.4.29 2,2′,3,3′,4,4′,5,6′-Octachlorodiphenyl ether (PCDE-196) . . . . . . . . . . . . . . . . . . . . . . . . 2397 10.1.4.30 2,2′,3,3′,4,4′,6,6′-Octachlorodiphenyl ether (PCDE-197) . . . . . . . . . . . . . . . . . . . . . . . . 2398 10.1.4.31 2,2′,3,3′,4,4′,5,5′,6-Nonachlorodiphenyl ether (PCDE-206) . . . . . . . . . . . . . . . . . . . . . . 2399 10.1.4.32 Decachlorodiphenyl ether (PCDE-209) . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2400 10.1.5 Brominated diphenyl ethers . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2401 10.1.5.1 2-Bromodiphenyl ether (BDE-1) . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2401 10.1.5.2 3-Bromodiphenyl ether (BDE-2) . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2402 10.1.5.3 4-Bromodiphenyl ether (BDE-3) . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2403 10.1.5.4 2,4-Dibromodiphenyl ether (BDE-7) . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2405 10.1.5.5 2,4′-Dibromodiphenyl ether (BDE-9) . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2406 10.1.5.6 2,6-Dibromodiphenyl ether (BDE-10) . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2407 10.1.5.7 3,4-Dibromodiphenyl ether (BDE-12) . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2408 10.1.5.8 3,4′-Dibromodiphenyl ether (BDE-13) . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2409 10.1.5.9 4,4′-Dibromodiphenyl ether (BDE-15) . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2410 10.1.5.10 2,2′,4-Tribromodiphenyl ether (BDE-17) . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2412 10.1.5.11 2,4,4′-Tribromodiphenyl ether (BDE-28) . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2414 10.1.5.12 2,4,6-Tribromodiphenyl ether (BDE-30) . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2417 10.1.5.13 2,4′,6-Tribromodiphenyl ether (BDE-32) . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2418 10.1.5.14 2′,3,4-Tribromodiphenyl ether (BDE-33) . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2419 10.1.5.15 3,3′,4-Tribromodiphenyl ether (BDE-35) . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2420 10.1.5.16 3,4,4′-Tribromodiphenyl ether (BDE-37) . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2421 10.1.5.17 2,2′,4,4′-Tetrabromodiphenyl ether (BDE-47) . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2422 10.1.5.18 2,3′,4,4′-Tetrabromodiphenyl ether (BDE-66) . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2425 10.1.5.19 2,3′,4,6-Tetrabromodiphenyl ether (BDE-69) . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2427 © 2006 by Taylor & Francis Group, LLC © 2006 by Taylor & Francis Group, LLC Ethers 2261 10.1.5.20 3,3′,4,4′-Tetrabromodiphenyl ether (BDE-77) . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2428 10.1.5.21 2,2′,3,3′,4-Pentabromodiphenyl ether (BDE-82) . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2430 10.1.5.22 2,2′,3,4,4′-Pentabromodiphenyl ether (BDE-85) . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2431 10.1.5.23 2,2′,4,4′,5-Pentabromodiphenyl ether (BDE-99) . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2433 10.1.5.24 2,2′,4,4′,6-Pentabromodiphenyl ether (BDE-100) . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2436 10.1.5.25 2,3,4,4′,6-Pentabromodiphenyl ether (BDE-115) . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2439 10.1.5.26 3,3′,4,4′,5-Pentabromodiphenyl ether (BDE-126) . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2440 10.1.5.27 2,3,3′,4,4′,5′-Hexabromodiphenyl ether (BDE-138) . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2442 10.1.5.28. 2,2′,4,4′,5,5′-Hexabromodiphenyl ether (BDE-153) . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2443 10.1.5.29 2,2′,4,4′,5,6′-Hexabromodiphenyl ether (BDE-154) . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2446 10.1.5.30 2,3,3′,4,4′,5-Hexabromodiphenyl ether (BDE-156) . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2448 10.1.5.31 2,2′,3,4,5,5′,6-Heptabromodiphenyl ether (BDE-183) . . . . . . . . . . . . . . . . . . . . . . . . . . 2450 10.1.5.32 2′,3,3′,4,4′,5,6-Heptabromodiphenyl ether (BDE-190) . . . . . . . . . . . . . . . . . . . . . . . . . . 2452 10.1.5.33 Decabromodiphenyl ether (BDE-209) . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2453 10.2 Summary Tables and QSPR Plots . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2455 10.3 References . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2463 © 2006 by Taylor & Francis Group, LLC © 2006 by Taylor & Francis Group, LLC [...]...2262 10.1 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals LIST OF CHEMICALS AND DATA COMPILATIONS 10.1.1 10.1.1.1 ALIPHATIC ETHERS Dimethyl ether (Methyl ether) O Common Name: Dimethyl ether Synonym: methyl ether, oxapropane, oxybismethane Chemical Name: dimethyl ether, methyl ether, CAS Registry No: 115-10-6 Molecular Formula:C2H6O, CH3OCH3 Molecular... Biodegradation: Biotransformation: Bioconcentration, Uptake (k1) and Elimination (k2) Rate Constants or Half-Lives: Half-Lives in the Environment: Air: disappearance t½ < 0.24 h from air) for the reaction with OH radical (Darnall et al 1976) © 2006 by Taylor & Francis Group, LLC © 2006 by Taylor & Francis Group, LLC 2278 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals TABLE... & Francis Group, LLC © 2006 by Taylor & Francis Group, LLC 2282 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals Biodegradation: Biotransformation: Bioconcentration, Uptake (k1) and Elimination (k2) Rate Constants or Half-Lives: Half-Lives in the Environment: Air: disappearance t½ < 0.24 h from air for the reaction with OH radical (USEPA 1974; quoted, Darnall et... Francis Group, LLC © 2006 by Taylor & Francis Group, LLC 2264 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals kOH* = 2.86 × 10–12 cm3 molecule–1 s–1 at 298 K, measured range 263–351 K (relative rate method, DeMore & Bayes 1999) Hydrolysis: Biodegradation: Biotransformation: Bioconcentration, Uptake (k1) and Elimination (k2) Rate Constants or Half-Lives: Half-Lives... 0.0038 1/(T/K) FIGURE 10.1.1.3.1 Logarithm of mole fraction solubility (ln x) versus reciprocal temperature for methyl t-butyl ether (MTBE) © 2006 by Taylor & Francis Group, LLC © 2006 by Taylor & Francis Group, LLC 2274 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals TABLE 10.1.1.3.2 Reported vapor pressures of methyl tert-butyl ether (MTBE) at various temperatures... 0.0037 0.0038 1/(T/K) FIGURE 10.1.1.3.3 Logarithm of Henry’s law constant versus reciprocal temperature for methyl t-butyl ether (MTBE) © 2006 by Taylor & Francis Group, LLC © 2006 by Taylor & Francis Group, LLC 2276 10.1.1.4 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals Di-n-propyl ether O Common Name: Di-n-propyl ether Synonym: 4-oxaheptane, 1,1′-oxibispropane,... 0.0062 0.007 0.0078 0.0086 1/(T/K) FIGURE 10.1.1.1.1 Logarithm of vapor pressure versus reciprocal temperature for dimethyl ether © 2006 by Taylor & Francis Group, LLC © 2006 by Taylor & Francis Group, LLC 2266 10.1.1.2 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals Diethyl ether (Ethyl ether) O Common Name: Diethyl ether Synonym: ether, ethyl ether, ethoxyethane,... Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals 8.0 Diethyl ether: vapor pressure vs 1/T Taylor & Smith 1922 Kobe et al 1956 Ambrose et al 1972 Stull 1947 7.0 S log(P /Pa) 6.0 5.0 4.0 3.0 2.0 1.0 m.p = -116.2 °C b.p = 34.5 °C 0.0 0.002 0.0028 0.0036 0.0044 0.0052 0.006 0.0068 1/(T/K) FIGURE 10.1.1.2.2 Logarithm of vapor pressure versus reciprocal temperature for. .. text 2284 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals 8.0 Diisopropyl ether: vapor pressure vs 1/T experimental data Stull 1947 7.0 S log(P /Pa) 6.0 5.0 4.0 3.0 2.0 1.0 m.p = -85.4 °C b.p = 68.4 °C 0.0 0.0026 0.003 0.0034 0.0038 0.0042 0.0046 0.005 0.0054 0.0058 1/(T/K) FIGURE 10.1.1.5.2 Logarithm of vapor pressure versus reciprocal temperature for di-isopropyl... 2000) Octanol/Water Partition Coefficient, log KOW: 2.03 (shake flask-GC, Hansch & Anderson 1967) 2.03 (recommended, Sangster 1989) 2.03 (recommended, Hansch et al 1995) © 2006 by Taylor & Francis Group, LLC © 2006 by Taylor & Francis Group, LLC 2286 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals Octanol/Air Partition Coefficient, log KOA: 3.89 (head-space GC, Abraham . Francis Group, LLC 2262 Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals 10.1 LIST OF CHEMICALS AND DATA COMPILATIONS 10.1.1. T&F Informa plc. Boca Raton London New York Physical-Chemical Properties and Environmental Fate for Organic Chemicals Volume I Introduction and Hydrocarbons Donald