Handbook on Biodegradation and Biological Treatment of Hazardous Organic Compounds

463 Pages·1998·10.198 MB·English

by  Martin H. van Agteren, Sytze Keuning, Dick B. Janssen (auth.)

HANDBOOKON BIODEGRADATION-ANDBIOLOGICALTREATMENTOF
HAZARDOUSORGANICCONWOUNDS
ENVIRONMENT & CHEMISTRY
VOLUME2
Thetitlespublishedinthisseriesarelistedattheendofthisvolume.
Handbook on Biodegradation and
Biological Treatment of
Hazardous Organic Compounds
by
Martin H. van Agteren
UniversityofGroningen,
DepartmentofBiochemistry.
GroningenBiomolecularSciences andBiotechnologyInstitute.
FacultyofNaturalSciences.
Groningen,TheNetherlands
SytzeKeuning
BioclearEnvironmentalBiotechnology,
Groningen, TheNetherlands
and
DickB.Janssen
University ofGroningen,
DepartmentofBiochemistry,
Groningen BiomolecularSciencesandBiotechnologyInstitute,
FacultyofNaturalSciences,
Groningen, TheNetherlands
Springer-Science+BusinessMedia, B.V.
A C.I.P. Catalogue record for this book is available from the Library of Congress.
ISBN 978-90-481-5010-6 ISBN 978-94-015-9062-4 (eBook)
DOI 10.1007/978-94-015-9062-4
Printed on acid-free paper
All Rights Reserved
© 1998 Springer Science+Business Media Dordrecht
Originally published by Kluwer Academic Publishers in 1998.
Softcover reprint of the hardcover I st edition 1998
No part of the material protected by this copyright notice may be reproduced or
utilized in any form or by any means, electronic or mechanical,
including photocopying, recording or by any information storage and
retrieval system, without written permission from the copyright owner
Contents
Preface
vii
Chapter 1
Introduction 3
Biodegradation and biological treatment 4
- Biodegradation 4
- Aerobic degradation oforganic compounds 4
- Anaerobic degradation ofpollutants 5
- Cometabolic transformation ofpollutants 7
- Prerequisites for biodegradation and biological treatment 8
The objective of this book 9
Chapter structure and contents 10
Further reading 11
Chapter 2
Aliphatic compounds 13
2.1 Acrolein 15
2.2 Acrylonitrile 19
2.3 Diethylamine 25
2.4 Dimethylamine 29
2.5 Hydrazine 35
2.6 Ethene and ethylene oxide 39
2.7 Propylene oxide 45
2.8 Formaldehyde 51
2.9 Mineral oil 57
Summary 65
References 67
Chapter 3
Halogenated aliphatic compounds 77
3.I Chloromethanes 79
3.2 Chloroethenes 93
3.3 Chloroethanes and related compounds 111
3.4 Chloropropanes, -propenes and related compounds 127
3.5 Methyl bromide and 1,2-dibromoethane 137
3.6 Chlorofluorocarbons 143
3.7 Bis(2-chloroisopropyl)ether and related chloroethers 147
3.8 2-Chloro- and hexachloro-1,3-butadiene 151
3.9 Hexachlorocyclohexane 155
Summary 165
References 167
v
Chapter 4
Aromatic compounds 189
4.1Benzene 191
4.2Benzidine 203
4.3Biphenyl 207
4.4 Ethylbenzene 213
4.5Phenol 219
4.6Isopropylbenzene 229
4.7Styrene 235
4.8Toluene 243
4.9Xylene 257
4.10 Diethylhexyl phthalate 265
Summary 271
References 273
Chapter 5
Polyaromatic hydrocarbons (PADs) 287
5.1 PAHs with two fused aromatic rings 289
5.2 PAHs with three fused aromatic rings 307
5.3PAHs with four fused aromatic rings 321
5.4 PAHs with five or more fused aromatic rings 331
Summary 339
References 341
Chapter 6
Chlorinated aromaticcompounds 351
6.1Chloroanilines 353
6.2Chlorobenzenes 363
6.3 Chlorophenols 379
6.4 Chloronitrobenzenes 405
6.5 Chloronitrotoluenes 411
6.6 Chlorotoluenes 413
6.7Chlorotoluidines 419
6.8Dichlorobenzidines 423
6.9Monochloronaphthalenes 425
6.10Polychlorinated biphenyls and terphenyls 429
6.11Chlorinated dibenzo-p-dioxins and dibenzofurans 441
Summary 449
References 451
Chapter 7
Synonyms 475
Abbreviations 481
Glossary 483
Index 489
vi
Preface
The introductionof syntheticorganic chemicalsintotheenvironmentduring thelastfew
decades has given rise to major concern about the ecotoxicological effects and ultimate
fate of these compounds. The pollutantsthat are considered to be most hazardous because
of their intrinsic toxicity, high exposure level, or recalcitrant behavior in the environment
have been placed on blacklists and other policy priority lists. The fate of synthetic
compounds that enter the environment is mainly determined by their rate of
biodegradation, which therefore also has a major effect on the degree of bioaccumulation
and the risk of ecotoxicological effects. The degree and rate of biodegradation is also of
critical importance for the feasibility of biological techniques to clean up contaminated
sites and waste streams. The biodegradation of xenobiotics has thus been the subject of
numerousstudies, which resulted in thousandsofpublicationsinscientificjournals, books,
and conference proceedings. These studies led to a deeper understanding of the diversity
of biodegradation processes. As a result, it has become possible to enhance the rate of
degradation of recalcitrant pollutants during biological treatment and to design completely
newtreatment processes.
At present, much work is being done to expand the range of pollutants to which
biodegradationcan be applied, and to make treatment techniquesless expensiveand better
applicable for waste streams which are difficult to handle. In order to achieve these
objectives, one needs information about the chemical and physical properties of the
contaminants, and about the possibilities for biodegradation under a variety of
environmental conditions. Insight into biodegradation processes and the physiology of the
organisms involved isessential for selectingtreatment strategies.
Theobjective of this book isto present informationabout thebiodegradation of a range
of important synthetic chemicals. Microbial-degradation pathways are presented and the
consequencesfor applicabilityintreatment systemsare discussed. The book is intendedfor
use by engineers, chemists, microbiologists, toxicologists, and environmental scientists
who are involved in the development, introduction, operation or evaluation of biological
treatmentsystems. The figures and tablesinthebook shouldleadto a better understanding
of degradation routes and indicate under which conditions specific microorganisms or
consortiacanbe used to degrade a selectedcompound.
Althoughabriefintroduction aboutthe generalprinciples ofbiodegradation processesis
given, the text assumes that the reader has a basic knowledge of microbiology and bio
degradation in general.
The compilation of this book has been funded by Senter as part of the Innovative
Research Programme Environmental Biotechnologyunder contract 1MB93012. We thank
the members of the advisory committee Dr. Ir. J. Bovendeur, and Ir. E. Krowinkel for
their helpful support throughout this project. We also acknowledge our colleaguesTjibbe
Bosma, Margriet Derix, Inez Dinkla, Wim de Koning, Jeffrey Lutje Spelberg, Astrid
Mars, Wouter Noordman, Ton Schoot Uiterkamp, and Johan van Hylckama Vlieg for
reviewingchapters of thisbook.
Martin H. vanAgteren
Dick B. Janssen
Sytze Keuning
vii
Acknowledgement
Thisstudy has beensubsidisedbytheInnovationOriented Research Programme(lOP) on
Environmental Biotechnology.The lOP Programme is managed by Senter. Senteris the
executive agency of the Ministry of Economic Affairs that manages and implements
programmes and schemes which increase thecompetitivepower of the Dutch Economy,
foster internationalcooperationandpromotesustainable development. Ithasmadeitsmark
particularlyinthe fieldsoftechnology,energy andenvironment.
EnTEr
(;)1
1
Chapter
Introduction