Environmental Degradation and Transformation of Organic Chemicals (2007)(en)(710s) PDF
Preview Environmental Degradation and Transformation of Organic Chemicals (2007)(en)(710s)
Environmental Degradation and Transformation of Organic Chemicals CCRRCC__77224411__FFmm..iinndddd ii 66//2211//22000077 11::1122::3311 PPMM CCRRCC__77224411__FFmm..iinndddd iiii 66//2211//22000077 11::1122::3322 PPMM Environmental Degradation and Transformation of Organic Chemicals Alasdair H. Neilson Ann-Sofie Allard and Boca Raton London New York CRC Press is an imprint of the Taylor & Francis Group, an informa business CCRRCC__77224411__FFmm..iinndddd iiiiii 66//2211//22000077 11::1122::3322 PPMM CRC Press Taylor & Francis Group 6000 Broken Sound Parkway NW, Suite 300 Boca Raton, FL 33487-2742 © 2008 by Taylor & Francis Group, LLC CRC Press is an imprint of Taylor & Francis Group, an Informa business 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: 0-8493-7241-0 (Hardcover) International Standard Book Number-13: 978-0-8493-7241-4 (Hardcover) 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. 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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 Neilson, Alasdair H. Environmental degradation and transformation of organic chemicals / Alasdair H. Neilson and Ann-Sofie Allard. p. cm. Rev. ed. of: Organic chemicals. c2000. Includes bibliographical references and index. ISBN 978-0-8493-7241-4 (alk. paper) 1. Aquatic organisms--Effect of water pollution on. 2. Organic water pollutants--Environmental aspects. I. Allard, Ann-Sofie. II. Neilson, Alasdair H. Organic chemicals. III. Title. QH545.W3N45 2008 577’.14--dc22 2007012219 Visit the Taylor & Francis Web site at http://www.taylorandfrancis.com and the CRC Press Web site at http://www.crcpress.com CCRRCC__77224411__FFmm..iinndddd iivv 66//2211//22000077 11::1122::3322 PPMM Contents Preface ............................................................................................................................................xix Acknowledgments ........................................................................................................................xxiii Authors ...........................................................................................................................................xxv SECTION I Degradation and Transformation Processes Chapter 1 Abiotic Reactions .........................................................................................................3 Introduction ........................................................................................................................................3 Photochemical Reactions in Aqueous and Terrestrial Environments ...............................................3 The Diversity of Photochemical Transformations .............................................................................4 The Role of Hydroxyl Radicals ..............................................................................................4 Illustrative Examples of Photochemical Transformations in Aqueous Solutions ..................5 Hydroxyl Radicals in the Destruction of Contaminants ....................................................................9 Fenton’s Reagent .....................................................................................................................9 Polyoxometalates (Heteropolyacids) .....................................................................................10 Photolytic Degradation on TiO ...........................................................................................10 2 Other Photochemically Induced Reactions......................................................................................11 The Role of Humic Matter: Singlet Dioxygen .................................................................................12 Interactions between Photochemical and Other Reactions .............................................................13 Reactions in the Troposphere...........................................................................................................14 Survey of Reactions ..............................................................................................................15 Survey of Reactants ..............................................................................................................17 Aliphatic Hydrocarbons .............................................................................................17 Aromatic Hydrocarbons.............................................................................................17 Biogenic Terpenes ......................................................................................................17 Reentry of Tropospheric Transformation Products .........................................................................18 Halogenated Alkanes and Alkenes .......................................................................................18 Arenes and Nitroarenes ........................................................................................................20 Alkylated Arenes ..................................................................................................................21 Sulfi des and Disulfi des .........................................................................................................21 Chemically Mediated Transformations ...........................................................................................22 Hydrolysis .............................................................................................................................22 Reductive Displacement: Dehalogenation and Desulfurization ...........................................25 Reductive Dehalogenation ...............................................................................................................25 Zero-Valent Metals ...............................................................................................................25 Chromous Chloride ..............................................................................................................26 Porphyrins and Corrins ........................................................................................................26 Thiol Reductants ..............................................................................................................................27 Reductive Desulfurization ...............................................................................................................28 Reductions Other than Dehalogenation ................................................................................28 Nucleophilic Reactions .........................................................................................................29 v CCRRCC__77224411__FFmm..iinndddd vv 66//2211//22000077 11::1122::3322 PPMM vi Contents Oxidations .............................................................................................................................30 Anodic Oxidation .......................................................................................................30 Ozone ......................................................................................................................30 Hydrogen Peroxide .....................................................................................................32 Manganese Dioxide ...................................................................................................32 Sulfate Radicals .........................................................................................................32 Halogenation .........................................................................................................................32 Thermal Reactions ................................................................................................................34 Gas Phase ...................................................................................................................34 In Water ......................................................................................................................36 Electrocatalytic Reactions ....................................................................................................37 References ........................................................................................................................................38 Chapter 2 Biotic Reactions..........................................................................................................51 Part 1 Microbial Reactions ..............................................................................................................51 Introduction ..........................................................................................................................51 Defi nitions—Degradation and Transformation ....................................................................51 Biodegradation of Enantiomers ............................................................................................54 Sequential Microbial and Chemical Reactions ....................................................................55 The Spectrum of Organisms .................................................................................................57 Bacteria in Their Natural Habitats .............................................................................57 Marine and Oligotrophic Bacteria .............................................................................58 Lithotrophic Bacteria .................................................................................................60 Phototrophic Organisms ............................................................................................61 Aerobic and Facultatively Anaerobic Bacteria ..........................................................62 Bacterial Metabolism of C Compounds: Methanotrophs, Methylotrophs, 1 and Related Organisms ..............................................................................................69 Methane Monooxygenase and Related Systems ........................................................69 Anaerobic Bacteria ...............................................................................................................72 Clostridia ....................................................................................................................73 Anaerobic Sulfate-Reducing Bacteria .......................................................................73 Other Anaerobic Bacteria ..........................................................................................73 Organisms from Extreme Environments ..............................................................................74 Psychrophiles .............................................................................................................74 Thermophiles .............................................................................................................75 Alkaliphiles ................................................................................................................75 Halophiles ..................................................................................................................75 Eukaryotic Microorganisms: Fungi and Yeasts ...................................................................75 Metabolism by Fungi .................................................................................................75 Metabolism by Yeasts ................................................................................................77 References .............................................................................................................................78 Part 2 Reactions Mediated by Higher Organisms ...........................................................................91 Introduction ..........................................................................................................................91 Metabolism by Fish ..............................................................................................................93 Metabolism by Other Organisms..........................................................................................95 Mussels ......................................................................................................................95 Insects ...................................................................................................................................96 Invertebrates .........................................................................................................................96 Isopods ......................................................................................................................97 Oligochaetes ...............................................................................................................97 Polychaetes .................................................................................................................97 CCRRCC__77224411__FFmm..iinndddd vvii 66//2211//22000077 11::1122::3322 PPMM Contents vii Higher Plants ........................................................................................................................97 Other Organisms ...................................................................................................................99 References ...........................................................................................................................100 Chapter 3 Mechanistic Aspects ................................................................................................103 Part 1 Introduction of Oxygen .......................................................................................................103 Monooxygenation ...............................................................................................................103 Hydroxylation of Alkanes ........................................................................................103 Epoxidation of Alkenes ...........................................................................................104 Cycloalkanone Monooxygenases .............................................................................105 Monooxygenation of Aromatic Compounds ............................................................106 Reactions of Aromatic Hydrocarbons .....................................................................107 Reactions of Hydroxybenzoates and Related Compounds ......................................108 Monooxygenation of Phenols ...................................................................................110 Cytochrome P450 Systems .................................................................................................113 Prokaryotic Organisms ............................................................................................114 Eukaryotic Organisms .............................................................................................116 Dioxygenation .....................................................................................................................118 Dioxygenases Involved in Dihydroxylation of Arenes ............................................118 Ring-Fission Dioxygenases ......................................................................................123 Incorporation of Oxygen from Water: Oxidoreductases and Hydratases ...........................129 Oxidoreductases .......................................................................................................129 Hydratases ................................................................................................................130 Oxidases, Peroxidases, and Haloperoxidases .....................................................................131 Oxidases ...................................................................................................................131 Peroxidases ..............................................................................................................133 Haloperoxidases .......................................................................................................134 References ...........................................................................................................................135 Part 2 Electron Acceptors Other than Oxygen ..............................................................................147 Introduction ........................................................................................................................147 Oxyanions: Nitrate, Sulfate, Chlorate, Selenate, and Arsenate ..........................................148 Nitrate and Related Compounds ..............................................................................148 Sulfate and Related Compounds ..............................................................................150 Chlorate and Perchlorate ..........................................................................................150 Selenate and Arsenate ..............................................................................................151 Metal Cations and Oxyanions ............................................................................................152 V(V), Mn(IV), Fe(III), Tc(VII), and U(VI) .............................................................152 Humic Acid and Anthraquinone-2,6-Disulfonate in Redox Systems .....................................................................................................154 Dehalorespiration................................................................................................................156 Alkane Sulfonates as Terminal Electron Acceptors ...........................................................156 Nitroalkanes as Electron Acceptor .....................................................................................156 References ...........................................................................................................................157 Part 3 Reductases and Related Enzymes .......................................................................................162 Reduction of Nitroarenes ....................................................................................................162 Nitrate Ester Reductase ......................................................................................................162 Enones (α, β-Unsaturated Ketones) and Related Reductases .............................................163 Aerobic Conditions ..................................................................................................163 Anaerobic Conditions ..............................................................................................163 Azo Reductase ....................................................................................................................163 CCRRCC__77224411__FFmm..iinndddd vviiii 66//2211//22000077 11::1122::3333 PPMM viii Contents Aldehyde Oxidoreductases .................................................................................................164 F -Dependent (Desazatetrahydrofolate) Reductases ........................................................164 420 Other Carbocyclic Aromatic Compounds ..........................................................................164 Reduction of Carbocyclic Rings ..............................................................................164 Dehydroxylation .......................................................................................................165 Reduction of Azaarene Rings ..................................................................................165 Metal Cations and Oxyanions ............................................................................................165 References ...........................................................................................................................166 Part 4 Microbial Reactions to Chemical Stress .............................................................................168 Introduction ........................................................................................................................168 Hydrocarbon Tolerance ............................................................................................168 Antibiotic Resistance ...............................................................................................170 Resistance to Metals and Metalloids ..................................................................................172 Reduction .................................................................................................................172 Methylation ..............................................................................................................173 Effl ux Systems .........................................................................................................175 Chlorophenol Tolerance ...........................................................................................176 Resistance to High Acidity ......................................................................................176 References ...........................................................................................................................177 Part 5 Enzymes Containing Manganese, Iron, Nickel, Copper, Molybdenum, Tungsten, and Vanadium .....................................................................................................181 Manganese ..........................................................................................................................181 Iron ..................................................................................................................................181 Nickel ..................................................................................................................................182 Copper.................................................................................................................................184 Molybdenum .......................................................................................................................185 Molybdopterin Oxidoreductases ..............................................................................185 Tungsten ..............................................................................................................................187 Vanadium ............................................................................................................................188 References ...........................................................................................................................188 Chapter 4 Determinants and Interactions .................................................................................193 Single Substrates: Several Organisms ...........................................................................................193 Cometabolism and Related Phenomena.........................................................................................195 Induction of Catabolic Enzymes ....................................................................................................195 Pre-Exposure to an Analog Substrate ................................................................................195 Enzyme Induction by Growth on Structurally Unrelated Compounds ..............................197 Role of Readily Degraded Substrates ............................................................................................198 Physical Parameters .......................................................................................................................200 Temperature ........................................................................................................................200 Oxygen Concentration ........................................................................................................201 Anaerobic Bacteria ..................................................................................................202 Aerobic and Facultatively Anaerobic Organisms ....................................................202 Redox Potential ...................................................................................................................205 Association of Bacteria with Particulate Material: “Free” and “Bound” Substrates .............................................................................................................205 Biological Mechanisms for Association with Organic Components of Soil and Sediment ...........................................................................................................206 Aging ..................................................................................................................................208 CCRRCC__77224411__FFmm..iinndddd vviiiiii 66//2211//22000077 11::1122::3333 PPMM Contents ix Substrate Concentration, Transport into Cells, and Toxicity .........................................................210 Utilization of Low Substrate Concentrations .....................................................................211 Existence of Threshold Concentrations ..............................................................................212 Strategies Used by Cells for Substrates with Low or Negligible Water Solubility ............213 Transport Mechanisms .......................................................................................................214 Pre-Exposure: Pristine and Contaminated Environments .............................................................215 Rates of Metabolic Reaction ..........................................................................................................218 Kinetic Aspects ...................................................................................................................218 Metabolic Aspects: Nutrients.........................................................................................................219 Regulation and Toxic Metabolites .................................................................................................220 Regulation ...........................................................................................................................220 Toxic or Inhibitory Metabolites ..........................................................................................222 Catabolic Plasmids .........................................................................................................................224 References ......................................................................................................................................227 SECTION II Experimental Procedures Chapter 5 General Experimental Procedures ...........................................................................245 Introduction ....................................................................................................................................245 Abiotic Reactions ................................................................................................................245 Microbial Reactions ............................................................................................................246 Storage of Samples .............................................................................................................247 Determination of Ready Biodegradability .........................................................................247 The Inoculum ...........................................................................................................248 Concentration of the Substrate .................................................................................248 Endpoints .................................................................................................................248 Design of Experiments on Inherent Biodegradability ........................................................248 Metabolic Limitations ..............................................................................................248 Application to Marine Systems................................................................................249 Isolation and Elective Enrichment ...........................................................................249 General Procedures ..................................................................................................250 Basal Media .............................................................................................................252 Mineral Media .........................................................................................................252 Trace Elements .........................................................................................................253 Control of pH ...........................................................................................................254 Vitamins ...................................................................................................................254 Sterilization ..............................................................................................................254 Metal Concentration in Metabolism ........................................................................254 Redox Potential of Media ........................................................................................256 Organic Substrates ..............................................................................................................256 Toxic Compounds ....................................................................................................256 Volatile Compounds .................................................................................................257 Solid Media .........................................................................................................................257 Growth at the Expense of Alternative Substrates ...............................................................258 Techniques for Anaerobic Bacteria ....................................................................................258 Design of Experiments on Biodegradation and Biotransformation ...................................259 Pure Cultures and Stable Consortia ....................................................................................259 Cell Growth at the Expense of the Xenobiotic ...................................................................260 CCRRCC__77224411__FFmm..iinndddd iixx 66//2211//22000077 11::1122::3344 PPMM
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