2nd Edition

Organic Chemicals in the Environment Mechanisms of Degradation and Transformation, Second Edition

    1048 Pages 415 B/W Illustrations
    by CRC Press

    1047 Pages 415 B/W Illustrations
    by CRC Press

    Addressing the persistent environmental threat of organic chemicals with a fresh approach to degradation and transformation processes, Organic Chemicals in the Environment: Mechanisms of Degradation and Transformation, Second Edition  examines a wide range of compounds as well as abiotic and microbiological reactions mediated by microorganisms. The book emphasizes the pathways used and the broad classes of enzymes involved. It provides an overview of experimental procedures with detailed coverage of the organic compounds that are considered to be xenobiotics.

    The book begins by providing a broad perspective on abiotic and biotic reactions, including the significance of a range of environmental determinants. The following chapters briefly introduce experimental procedures and emphasize those procedures for establishing the structure of metabolites using isotopes and physical methods. Next, the authors outline details of biochemical reactions involved in the biodegradation of the major groups of aliphatic, carbocyclic aromatic, and heterocyclic compounds. They end with coverage of bioremediation that has attracted increasing concern because of the hazard presented by the disposal of unwanted chemicals or by-products from their manufacture.

    Broad and comprehensive, this book provides a cohesive treatment of the subject. It contains an extensive set of literature references and numerous illustrative figures. The authors use a mechanistic approach with emphasis on the pathways, and the principles that emerge provide a guide not only for specific compounds but also for those having a more remote structural resemblance.

    Degradation and Transformation Processes
    Abiotic Reactions: An Outline
    Introduction
    Photochemical Reactions in Aqueous and Terrestrial Environments
    The Diversity of Photochemical Transformations
    Hydroxyl Radicals in the Destruction of Contaminants
    Other Photochemically Induced Reactions
    The Role of Humic Matter: Singlet Dioxygen
    Interactions between Photochemical and Other Reactions
    Reactions in the Troposphere
    Reentry of Tropospheric Transformation Products
    Chemically Mediated Transformations
    Reductive Dehalogenation
    Thiol and Sulfide Reductants
    Sonication
    References

    Biotic Reactions: An Outline of Reactions and Organisms
    Microbial Reactions
    Introduction
    Definitions: Degradation and Transformation
    Biodegradation of Enantiomers: Racemization
    Sequential Microbial and Chemical Reactions
    The Spectrum of Organisms
    Microbial Metabolism of CCompounds
    Anaerobic Bacteria
    Organisms from Extreme Environments: Extremophiles
    Eukaryotic Microorganisms
    References
    Reactions Mediated by Other Biota
    Aquatic and Terrestrial Biota
    Metabolism by Fish
    Metabolism by Other Organisms
    References
    Plants and Their Microbial Interactions
    Introduction
    Primary Roles of Plants
    Secondary Role of Plants
    Plant Metabolites as Antagonists
    Group
    Group II Phytoalexins
    Roles of Bacteria Including Biocontrol Agents
    Plant Endophytes
    Microorganisms with Activity as Biocontrol Agents
    Siderophores in Plants: Roles of Iron
    The Role of Mycorrhizal and Other Fungi
    Conclusions
    References

    Mechanisms
    Oxidation, Dehydrogenation, and Reduction
    Introduction
    Monooxygenation
    References
    Dioxygenation
    References
    Oxidases, Peroxidases, and Haloperoxidases
    References
    Incorporation of Oxygen from Water: Hydrolases, Oxidoreductases, and Hydratases
    References
    Electron Acceptors Other than Oxygen
    References
    Dehydrogenation
    References
    Reductases and Related Enzymes
    References
    Non-Redox Reactions
    Pyridoxal-'-Phosphate (PLP)-Dependent Reactions
    References
    Glutathione-Dependent Reactions
    References
    Corrinoid-Dependent Reactions
    References
    Free-Radical Reactions
    References
    Coenzyme A: Ligase, Transferase, Synthetase
    References
    Metalloenzymes
    Enzymes Containing Manganese, Iron, Cobalt, Copper, Zinc, Molybdenum, Tungsten, and Vanadium
    References

    Interactions
    Environmental Stress
    Adaptation to Stress
    Physical Stress
    References
    Chemical Stress
    Enzymatic Covalent Modification of Antibiotic: Range of Reactions
    Efflux Systems
    References
    Metabolic Interactions
    Single Substrates: Several Organisms
    Cometabolism and Related Phenomena
    Induction of Catabolic Enzymes
    Role of Readily Degraded Substrates
    Association of Bacteria with Particulate Material: "Free" and "Bound" Substrates
    Substrate Concentration, Transport into Cells, and Toxicity
    Preexposure: Pristine and Contaminated Environments
    Rates of Metabolic Reaction
    Metabolic Aspects: Nutrients
    Regulation and Toxic Metabolites
    Catabolic Plasmids
    References

    Experimental Procedures
    Experimental Procedures

    General
    Introduction
    Abiotic Reactions
    Microbial Reactions
    Storage of Samples
    Determination of Ready Biodegradability
    Design of Experiments on Inherent Biodegradability
    Organic Substrates
    Techniques for Anaerobic Bacteria
    Design of Experiments on Biodegradation and Biotransformation
    Pure Cultures and Stable Consortia
    Cell Growth at the Expense of the Xenobiotic
    Stable Enrichment Cultures
    Use of Dense Cell Suspensions
    Use of Immobilized Cells
    Application of Continuous Culture Procedures
    Simultaneous Presence of Two Substrates
    Use of Unenriched Cultures: Undefined Natural Consortia
    Microcosm Experiments
    Experiments in Models of Natural Aquatic Systems
    Evaluation of Degradation Using Metabolites
    Experimental Problems: Water Solubility, Volatility, Sampling, and Association of the Substrate with Microbial Cells
    References
    Study of Microbial Populations
    Introduction
    Analysis of Degradative Populations
    Procedures Directed to Populations for the Degradation of Specific Contaminants
    Application to Populations of Specific Groups of Organisms
    Nonspecific Examination of Natural Populations
    References

    Procedures for Elucidation of Metabolic Pathways
    Introduction
    Application of Natural and Synthetic Isotopes
    Carbon (C and C)
    Sulfur (S) and Chlorine (Cl)
    Hydrogen (H) and Oxygen (O)
    Other Isotopes
    Isotope Effects and Stable Isotope Fractionation
    References
    Stable Isotope Probes and Stable Isotope Fractionation
    Experimental Procedures
    Expression of Results
    Stable Isotope Probes
    Application to Processes
    Application to Biodegradation
    Stable Isotope Fractionation
    References
    Physical Methods of Structure Determination
    Nuclear Magnetic Resonance
    References
    Electron Paramagnetic Resonance
    References
    X-Ray Crystallographic Analysis
    Acetylene Hydratase
    Triesterase
    Dehydrogenases
    Quinoprotein Amine Oxidase
    Dehalogenases
    Atypical Dehydratases
    Arsenite Oxidase
    Methyl Coenzyme M Reductase
    Urease
    Hydrogenase
    ß-Lactamases
    Alkylsulfatase
    Dioxygenases
    Superoxide Dismutase
    Formyl-CoA Transferase
    PLP-Independent Racemases
    References

    Pathways and Mechanisms of Degradation and Transformation
    Aliphatic Compounds

    Alkanes
    References
    Cycloalkanes: Including Terpenoids and Steroids
    References
    Alkenes and Alkynes
    References
    Alkanols, Alkanones, Alkanoates, Amides
    References
    Alkylamines and Amino Acids
    Amino Acids
    References
    Alkanes, Cycloalkanes, and Related Compounds with Chlorine, Bromine, or Iodine Substituents
    Chlorinated, Brominated, and Iodinated Alkanes, Alkenes, and Alkanoates
    References
    Fluorinated Aliphatic Compounds
    References

    Carbocyclic Aromatic Compounds without Halogen Substituents
    Monocyclic Aromatic Hydrocarbons
    Introduction: Bacteria
    Monocyclic Arenes
    Fungi
    References
    Polycyclic Aromatic Hydrocarbons
    Introduction
    Aerobic Reactions Carried Out by Bacteria
    PAHs with Three or More Rings
    Anaerobic Degradations Carried Out by Bacteria
    Fungal Transformations
    Yeasts and Algae
    White-Rot Fungi
    References
    Aromatic Carboxylates, Carboxaldehydes, and Related Compounds
    Introduction
    Benzoates
    Hydroxybenzoates and Related Compounds
    Mechanisms for Fission of Oxygenated Rings
    Aerobic Reduction of Arene Carboxylates
    Arenes with an Oxygenated Cor CSide Chain
    Aldehydes
    References
    Nonhalogenated Phenols and Anilines
    Phenols
    Alkylated Phenols: Degradation of Methylcatechols
    Polyhydric Phenols
    Anaerobic Degradation
    References

    Halogenated Arenes and Carboxylates with Chlorine, Bromine, or Iodine Substituents
    Arenes and Carboxylated Arenes with Halogen, Sulfonate, Nitro, and Azo Substituents
    Aerobic Degradation
    Anaerobic Conditions
    Polychlorinated Biphenyls
    Polybrominated Biphenyls and Diphenylmethanes
    Mechanisms for the Ring Fission of Substituted Catechols
    Halogenated Phenylacetates
    References
    Halogenated (Chlorine, Bromine, and Iodine) Phenols and Anilines
    Phenols
    O- and S-methylation
    Fungi and Yeasts
    Anilines
    References
    Fluorinated Hydrocarbons, Carboxylates, Phenols, and Anilines
    Fluorinated Aromatic Hydrocarbons
    Fluorobenzoates
    -Fluorocinnamate
    Difluorobenzoates
    Fluorinated Phenols
    Aromatic Trifluoromethyl Compounds
    References

    Arene Sulfonates

    References
    Aromatic Compounds with Nitro Substituents
    Nitroarenes
    Nitrobenzoates
    Nitrophenols
    References
    Azoarenes
    References

    Heterocyclic Aromatic Compounds
    Azaarenes
    Five-Membered Monocyclic Aza, Oxa, and Thiaarenes
    Aerobic Conditions
    Indole and -Alkylindoles
    Carbazole
    Purines
    Triazines
    References
    Oxaarenes
    Aerobic Conditions
    Fungal Reactions
    References
    Thiaarenes: Benzothiophenes, Dibenzothiophenes, and Benzothiazole
    Benzothiophene and Dibenzothiophene
    Benzothiazole
    References

    Miscellaneous Compounds
    Carboxylate, Sulfate, Phosphate, and Nitrate Esters
    Carboxylates
    Sulfates
    Phosphates
    Nitrates
    References
    Ethers and Sulfides
    Aliphatic and Benzylic Ethers
    Aryl Ethers
    References
    Sulfides, Disulfides, and Related Compounds
    References
    Aliphatic Nitramines and Nitroalkanes
    Nitramines
    Nitroalkanes
    References
    Aliphatic Phosphonates and Sulfonates
    Introduction
    Phosphonates
    Sulfonates
    Boronates
    References
    Degradation of Organic Compounds of Metals and Metalloids
    Tin
    Lead
    Mercury
    Arsenic
    References
    Index

    Biography

    Alasdair H. Neilson was Principal Scientist until retirement from IVL Swedish Environmental Research Institute in Stockholm. He studied chemistry at the University of Glasgow and took his Ph.D. in organic chemistry in Alexander Todd's laboratory at Cambridge University. He carried out further research at Cambridge University in organic chemistry, and in theoretical chemistry with Charles Coulson at Oxford University. He held academic positions in the universities of Glasgow and Sussex, and obtained industrial experience in the pharmaceutical industry. He consolidated his experience by turning to research in microbiology during a prolonged stay with Roger Stanier and Mike Doudoroff at the University of California, Berkeley. His interests have ranged widely and included studies on nitrogen fixation, carbon and nitrogen metabolism in algae, and various aspects of environmental science including biodegradation and biotransformation, chemical and microbiological reactions in contaminated sediments, and ecotoxicology. With his group of collaborators, these studies have resulted in publications in Applied and Environmental Microbiology, Journal of Chromatography, Environmental Science & Technology, and Ecotoxicology & Environmental Safety, and in chapters contributed to several volumes of The Handbook of Environmental Chemistry. He is a member of the American Chemical Society, the American Society for Microbiology, the American Society of Crystallography, and the American Association for the Advancement of Science (AAAS).





    Ann-Sofie Allard studied as a chemical microbiologist and is currently a Senior Microbiologist at IVL Swedish Environmental Research Institute in Stockholm. She has carried out research on a wide range of water quality issues including the distribution of Yersinia enterocolitica in Swedish freshwater systems, and processes for the removal of hormone disrupters. She has carried out extensive studies on the biodegradation and biotransformation of organic contaminants, and in ecotoxicology, and she has implemented independent studies on the uptake and metabolism of organic contaminants and metals in higher plants in the context of bioremediation. Her studies have been published in Applied and Environmental Microbiology, International Biodeterioration and Biodegradation, Environmental Chemistry and Ecotoxicology, and Journal of Environmental Science and Health, and in chapters contributed to several volumes of The Handbook of Environmental Chemistry. She is a member of the American Chemical Society.

    "Now in its second edition, this large work is packed with useful and pertinent information concerning the potential fate of chemicals that have made their way, usually unintentionally, into the surrounding biosphere. … As usual with such books, the layout is neat and the print easy to read. Many chemical schemes and copious references after (and within) each chapter add to the work. Good quality paper, firm binding and an overall solid construction ensure that this book will remain durable for many years. For anyone with an interest in xenobiotics and environmental issues this book certainly is a useful reference source."
    —Steve Mitchell, Faculty of Medicine, Imperial College London, UK, 2013

    Praise for the First Edition:
    Broad and comprehensive, this book provides a cohesive treatment of the subject. It contains an extensive set of literature references and numerous illustrative figures.
    —J. Albaigés, CID-CSIC, Journal of Environmental Analytical Chemistry, Feb. 2008