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The Chemistry
of PCB's

0. Hutzinger
Director and Professor
Environmental Chemistry and
Toxicology Laboratory
University of Amsterdam
Amsterdam, The Netherlands

S. Safe
Director and Professor
Environmental Biochemistry Unit
University of Guelph
Guelph, Ontario

V. Zitko
Fisheries and Marine Service
St. Andrews, New Brunswick

Boca Raton London New York

CRC Press is an imprint of the

Taylor & Francis Group, an informa business
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© 1974 by CRC Press, Inc.

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 PREFACE
In the last few years polychlorinated biphenyls A considerable amount of information included
(PCB's) have attained the dubious honor of sur- in this book had not been published when the
passing the chlorinated insecticides as the most manuscript was written. Although some of this
talked-about organochlorine pollutants. information comes from our own laboratories, we
have to acknowledge the help of many scientists
Research on various aspects of the PCB prob- who have generously supplied us with their un-
lem has grown and continues to grow with published data. It is a great pleasure to thank the
remarkable intensity. Opinions on the importance following colleagues for this courtesy: Drs. M.
of these ubiquitously distributed industrial com- Bolgar, E. J. Bonelli, G. W. Bowes, R. H. DeVos,
pounds, however, still vary greatly. The authors do R. Edwards, W. Ernst, V. H. Freed, A.M. Gardner,
not wish to enter this discussion. The main aim of A. V. Holden, W. D. Jamieson, S. Jensen, W. Klein,
this book is to present a comprehensive summary J. B. Knight, F. Korte, R. A. Lidgett, L. L. Miller,
of the chemistry of chlorobiphenyls. Included are D. R. Osborne, I. Pomerantz, L. 0. Ruzo, D. L.
the nomenclature, composition of technical mix- Stalling, J. D. Stewart, G. Sundstrom, A. C. Tas,
tures, syntheses of individual chlorobiphenyls, G. M. Telling, P.R. WallnOfer, and R. G. Webb.
chemical reactions, photochemical and metabolic We would like to express our appreciation to
alterations, and spectroscopic properties. Different Dr. K. L. Loening of Chemical Abstracts Service
methods of PCB analysis are presented and evalu- for advice with nomenclature and the Monsanto
ated in a separate chapter. Toxicological and Company for supplying samples and information.
general biological effects are frequently referred to Thanks are also due to CRC Press for their cooper-
but are not a proper topic for this book. ation; particularly for allowing us to submit the
Certain areas of PCB research are developed last chapter (Recent Developments) months after
further than others. For example, almost half of the original manuscript.
the 209 possible chlorobiphenyls have been Part of the contribution by one of us (0.
synthesized and properly described using a variety Hutzinger) was written while on sabbatical leave
of methods. Much is to be learned, on the other at the Institute of Ecological Chemistry. This
hand, on the metabolism of chlorobiphenyls and author would like to express his thanks for the
other routes of degradation, including photo- hospitality extended to him and also gratefully
chemical, and the complex PCB mixtures will acknowledge financial support from the Alexander
continue to challenge analytical chemists. In yet von Humboldt-Stiftung.
other areas, for example toxicological significance The literature for this book was covered, as it
and exact environmental impact, our knowledge is was available to the authors, until the end of
only fragmentary at the moment. 1973.
 THE AUTHORS

Otto Hutzinger is Professor and Director of the Environmental Chemistry and Toxicology Laboratory,
University of Amsterdam, The Netherlands. He holds an lng. Chern. degree from the Institute of
Chemical Technology in Vienna, Austria, and M.Sc. and Ph.D. degrees from the University of
Saskatchewan, Canada. He is presently a Senior Fellow of the Alexander von Humboldt Foundation at
the Institute of Ecological Chemistry, Technical University of Munich, Germany. His research interests
are the chemistry of pollutant compounds, particularly pesticides and industrial chemicals, and the
application of mass spectrometry to these studies. He is author or co-author of over 160 scientific
publications.

Stephen Safe is Associate Professor in the Department of Chemistry at the University of Guelph,
Guelph, Ontario. He holds B.Sc. and M.Sc. degrees from Queen's University, Canada, and a D.Phil.
from Oxford University. His work includes research in the chemistry and metabolism of pesticides and
pollutants, the application of mass spectrometry in environmental and other fields, and the bio-
chemistry and toxicology of pollutants. He is author or co-author of over 140 scientific papers.

Vladimir Zitko is the Leader of the Toxicology Section of the Fisheries and Marine Service, Biological
Station, St. Andrews, New Brunswick. He holds Ing. Chern. and C.Sc. (Ph.D.) degrees from the Slovak
Academy of Sciences, Bratislava, Czechoslovakia. His experience includes work in physical,
carbohydrate, and lipid chemistries. He is au thor or co-author of approximately 80 scientific
publications.
 TABLE OF CONTENTS

Chapter 1
Introduction .1
Historical and Literature .1
Toxicology of PCB's .1
Nomenclature .3
References .5

Chapter 2
Commercial PCB Preparations: Properties and Compositions .7
Introduction . ........... .7
General Information and Properties of PCB .7
Use of PCB . . . . . . . . . .7
Production Figures for PCB .7
Preparation and Properties of PCB .8
Chemical Composition of PCB Mixtures 22
References . . . . . . . . . . . . . . 39

Chapter 3
Synthesis of Chlorobiphenyls . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 41
Methods for the Synthesis of Chlorobiphenyls . . . . . . . . . . . . . . . . . . . . . . 41
1. Formation of Chlorobiphenyls by Phenylation of Aromatic Substrates (Usually Involving Free
Radical Mechanisms) . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 41
2. Formation of Chlorobiphenyls by Other Aryl Condensation Reactions . . . . . . . . 44
3. Formation of Chlorobiphenyls by Direct Substitution on the Preformed Biphenyl System 48
Tables Describing Known Chlorobiphenyls . . . . . 52
Methods for the Synthesis of Labeled Chlorobiphenyls 63
Chlorobiphenyls Labeled with Carbon-14 . . . . 63
Chlorobiphenyls Labeled with Chlorine-36 . . . . 64
Chlorobiphenyls Labeled with Deuterium and Tritium 64
References . . . . . . . . . . . . . . . . . . . . . . 67

Chapter 4
Other Biphenyl Syntheses . ............................ 71
Newer Synthesis of the Biphenyl Ring System . . . . . . . . . . . . . . . . . . . 71
Biphenyls Via Aryl Grignard Reagents or Aryl Lithium Compounds and Cyclic Ketones 71
Biphenyls by Coupling of Aromatic Compounds with Thallium (III) Acetate . . . . . 71
Biphenyls by Oxidation of Aromatic Compounds with Lead Tetraacetate in Trifluoroacetic Acid 71
Biphenyls by Oxidative Decomposition of N-phenyl-N' (tri-n-butylstannyl) hydrazines 72
Biphenyls from Acyclic Cross-conjugated Dienamines and Aromatic Acid Chlorides Ti
Biphenyls by Reaction of Acetylenes with a-methylene Carbonyl Compounds . 72
Biphenyls via Intermediate Iron Complexes . . . . . . . . . . . . . . . . . 73
Biphenyls from Aryl Halides and Bis (1,5-cyclooctadiene) Nickel (O) . . . . . . 73
Biphenyls by Photolysis of N-phenylsulfonyldimethyl Sulfoximine and Aromatic Bromo and Iodo
Compounds . . . . . . . . . . . . . . . . . . . . . . 73
Biphenyls from Aromatic Sulfur Compounds and Raney-Nickel 74
Biphenyls by Nucleophilic Aromatic Substitution 74
Biphenyls from Sulfonamides . . . . . . . . . . . . . 74
Biphenyls by Rearrangement of N ,0-Diarylhydroxylamines 75
Biphenyls by Photochemical Synthesis from Phenols . 76
Biphenyls from o-Bromobenzoates and Phloroglucinol 76
 Biphenyls by Oxidative Coupling . . . . . . . . . . . . . . . . . . . 76
Biphenyls by the Reduction of Diazonium Salts . . . . . . . . . . . . . 77
Biphenyls by the Condensation of Phenols or Diazonium Salts with Quinones 77
Synthesis of Chlorobiphenylamines (Aminochlorobiphenyls) . . . . . . . . . 77
1. Chlorobiphenylamines by Chlorination of Biphenylamines and Chlorobiphenylamines 78
2. Chlorobiphenylamines by Reduction of Chloronitrobiphenyls ...... 78
3. Benzidine Rearrangement of Chlorohydroazobenzenes and Related Reactions 78
4. Chlorobiphenylamines from Biphenylpolyamines ( -NH 2 ~ Cl) . . . . . . 79
5. Chlorobiphenylamines from Phenylhydroxylamine and Chlorobenzene 79
6. Chlorobiphenylamines by Condensation of Aminochlorobenzenediazonium Compounds with
Copper . . . . . . . . . . . . . . . . . . . . . . . . . 79
7. Chlorobiphenylamines by Hofmann Degradation of Carboxamides 80
8. Chlorobiphenylamines by Reduction of Azo Compounds 80
9. Chlorobiphenylamines from Polychlorobiphenyls and Ammonia 80
List of Chlorobiphenylamines (Aminochlorobiphenyls) Described in the Literature 80
Synthesis of Chlorobiphenylols (Chlorohydroxybiphenyls, Chlorophenylphenols) 80
1. Chlorobiphenylols from Chlorobiphenylamines Via Diazonium Salts (NH 2 ~ OH) 92
2. Chlorobiphenylols by Chlorination of Hydroxybiphenyls .......... 92
3. Chlorobiphenylols by Arylation Reaction (Decomposition of Diazonium Salts in Aromatic
Substrate) . . . . . . . . . . . . . . . . . .· . . . . . . . . . . . . . . 92
4. Chlorobiphenylols by Decarboxylation of Chlorohydroxybiphenylcarboxylic Acids 93
5. Chlorobiphenylols by the Action of Alkali of Sodium Methoxide on Chlorobiphenyls 93
6. Chlorobiphenylols by Isomerization Reaction . . . . . . . . . . . . . . . . . 94
7. Chlorobiphenylols from Aminobiphenylols Via Diazonium Salts (NH 2 ~ Cl) 94
8. Chlorobiphenylols by Photochemical or Thermal Reaction ofChlorobenzene-2-diazo-1-oxides in
Benzene . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 94
9. Chlorobiphenylols by Condensation of Chlorobenzene-2-diazo-1-oxides and Subsequent Reduc-
tion . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 94
10. Chlorobiphenylols by Coupling Diazonium Salts with Quinones and Reduction 94
11. Chlorobiphenylols by Condensation of Chlorophenols with Benzoyl Peroxide 95
12. Chlorobiphenylols by Electrochemical Oxidation of Chlorobiphenyls 95
13. Chlorobiphenylols by Hydroxylation of Chlorobiphenyls ....... 95
14. Chlorobiphenylols from Chlorobiphenyls Via Organothallium Compounds 95
15. Chlorobiphenylols by the lnlman Reaction ............. 96
16. Chlorobiphenylols by the Decomposition of Aryl-sulfonylchlorides in Aromatic Substrate 96
List of Chlorobiphenylols (Chlorohydroxybiphenyls) Described in the Literature 96
References . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1 09

Chapter 5
Chemical Reactions of Chlorobiphenyls . 113
Oxidation . 113
Reduction . 113
Chlorination . 113
Nitration . . 114
Reaction with Alkoxide . 115
Reaction with Amines . . 115
Nucleophilic Displacement of Chlorine . 115
Reaction with Thiolate Anion . 116
Organometallic Derivatives . 116
Isomerization Reactions . 116
Color and Related Reactions . 116
 Cyclizations of 2- and 2,2'-Substituted Biphenyls . . . . . 117
Formation of Diabenzofuran and Related Compounds . 117
References . . . . . . . . . . . . . . . . . . . . . . . 117

Chapter 6
Photodegradation of Chlorobiphenyls . 119
Introduction ........ . 119
Conditions of Irradiation . 120
Choice of Irradiation Sources . 120
Physical State of the Irradiated Compound Laboratory Models for Natural Conditions . 120
Theoretical Aspects . .................. . 122
Correlation of Absorption Spectra to Photochemical Activity . 122
Mechanism of Photochemical Degradation . 123
Photosensitization and Quenching . . . . . 123
Photoproducts Formed from Chlorobiphenyls . 123
Reductive Dechlorination . . . . . . . . 123
Isomerization, Condensation, and Chlorination . 125
Formation of Products Containing Oxygen . 126
Formation of Polymeric Products . 129
References . . . . . . . . . . . . . . . . . . 130

Chapter 7
Metabolism of Chlorobiphenyls . . . . . . . . . . 133
Introduction ............... . 133
Metabolic Change of Chlorobiphenyls by Animals . 133
Studies with Technical PCB Mixtures . 133
Studies with Individual Chlorobiphenyls . 138
Studies with Related Compounds . . . . 142
Metabolic Change of Chlorobiphenyls by Microorganisms . 143
Studies Involving Mixed Microbial Populations . 143
Studies Involving Pure Culture . 144
References . . . . . . . . . . . . . . . . . . . 148

Chapter 8
Mass Spectrometry of Chlorobiphenyls . 1 51
Mass Spectra of Individual Chlorobiphenyls . 151
Mass Spectra of Commercial Aroclor Samples . 161
Mass Spectra of Photolysis and Metabolic Products of Chlorobiphenyls . 162
Application of Chemical Ionization Mass Spectrometry to the Analysis of Chlorobiphenyls . 164
Mass Spectra of Chlorohydroxybiphenyls . . . 164
Plasma Chromatography of Chlorobiphenyls . 168
References . . . . . . . . . . . . . . . . . . . 170

Chapter 9
Nuclear Magnetic Resonance Spectroscopy of Chlorobiphenyls . . . . . . . 1 71
Proton Magnetic Resonance (PMR) Spectra of Individual Chlorobiphenyls . 171
PMR Spectra of Commercial Aroclors . . . . . 173
PMR Spectra of Hydroxylated Chlorobiphenyls . 173
References . . . . . . . . . . . . . . . . . . 188

Chapter 10
tntraviolet Spectroscopy of Chlorobiphenyls ........................ 189
 Chlorinated Biphenyls with Less than Two Chlorine Atoms Ortho to the Ph-Ph Bond . 189
Chlorinated Biphenyls with Two or More Chlorine Atoms Ortho to the Ph-Ph Bond . 191
References . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 193

Chapter 11
Infrared Spectrometry of Chlorobiphenyls . 195
References . . . . . . . . . . . . . . 196

Chapter 12
Determination of PCB's . ............. . 197
Sampling . . . . . . . . . . . . . . . . . . . . 197
Precautions Against Contamination in the Laboratory . 198
Extraction of PCB's . 199
Air . . . . . . . . . . . . . . 199
Water . . . . . . . . . . . . . 199
Soil, Sediment, Sludge, and Paper . 199
Biological Samples . 200
Cleanup of Extracts ..... . 201
Sulfuric Acid Cleanup . . . . 202
Microscale Alkali Treatment . 202
Low Temperature Precipitation of Lipids . 202
Acetonitrile Partitioning . . . 202
Chromatography on Alumina . . . . . . 203
Chromatography on Florisil . .... . 203
Separation of PCB's from Chlorinated Hydrocarbon Pesticides and Other Chlorinated Compounds 204
Thin-layer Chromatography of PCB's . 206
Confirmation of PCB's . . . . . . . 207
Quantitation of PCB's ...... . 210
Determination of Chlorobiphenylols . 213
Levels of PCB's in the Environment . 215
References . . . . . . . . . . . . . . 218

Chapter 13
Recent Developments . 221
A. Synthesis . 221
References . . . . . . 223
B. Photo- and Radiochemical Reactions . 223
References . . . 225
C. Metabolism . 226
References . . . 227
D. Mass Spectrometry . 228
1. Chlorobiphenyls (PCB's) . 228
2. Chlorobiphenylols (Hydroxylated PCB Metabolites) . 229
References . . . . . . . . . . . . . . . . 232
E. Nuclear Magnetic Resonance Spectroscopy . 232
References . . . . . . . . . . . . . . . . 238
F. illtraviolet and Luminescence Spectroscopy . 238
References . 242
G. Analysis . . . . . . . . . . . . . . . . 243
References . . . . . . . . . . . . . . . . 248
H. Occurrence, Levels, and Accumulation in the Environment . 249
References 0 oo 0 0 251
I. Biological Effects 0 252
References 0 252
Index o 0 o 0 o 0 0 253
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