Transformation Products of Emerging Contaminants in the Environment

EditorsDimitra A. Lambropoulou Department of Chemistry, Aristotle University of Thessaloniki, GreeceLeo M. L. Nollet Emeritus, Faculty of Applied Engineering Sciences, University College Ghent, Belgium

• Preface xiiiList of Contributors xvVOLUME 1PART I GENERAL CONSIDERATIONS 11 Classifying the Transformation Products (TPs) of Emerging Contaminants (ECs) for Prioritizing Research into their Impact on the Environment and Human Health 3Jacek Namiesnik, Lidia Wolska, Radosaw Czernych, Grazyna Gaeziowska and Monia Cieszynska1.1 Introduction 31.2 Emerging Contaminants – Emerging Problem 51.3 Transformation Products of ECs 411.4 Minimizing Environmental Risk of ECs and their TPs 431.5 Concluding Remarks and Future Perspectives 45References 492 Transformation Products of Emerging Organic Compounds as Future Groundwater and Drinking Water Contaminants 65Marianne E. Stuart and Dan J. Lapworth2.1 Introduction 652.2 Sources and Pathways of Emerging Contaminants to Groundwater 662.3 Persistence in the Groundwater Environment 682.4 Emerging Contaminants and their Transformation Products in Groundwater 692.5 Toxicity and Risk Assessment 762.6 Conclusions 78References 79PART II TRANSFORMATION PROCESSES AND TREATMENT STRATEGIES 873 Phototransformation Processes of Emerging Contaminants in Surface Water 89Davide Vione and Serge Chiron3.1 Introduction 893.2 Direct Photolysis and Sensitised Reactions in the Transformation of Emerging Contaminants 903.3 The Case of Photonitration 1043.4 Towards the Modelling of Phototransformation Kinetics in Surface Water 106References 1184 Transformation Products of Emerging Contaminants upon Reaction with Conventional Water Disinfection Oxidants 123Jose Benito Quintana, Rosario Rodil and Isaac Rodr©¥guez4.1 Introduction 1234.2 Analytical Methodology for Transformation Products Identification 1244.3 Factors Influencing the Kinetics of Chlorination 1314.4 Overview of Typical Reaction Mechanisms During Free Chlorine Treatments 1354.5 Review of Current Knowledge of Emerging Pollutant Reactions with Free Chlorine 1384.6 Other Disinfection Agents 1504.7 Conclusions and Outlook 155References 1555 Approaches to Water andWastewater Treatment for Removal of Emerging Contaminants: Ongoing Research and Recommendations for Future Work 161Sixto Malato, P. Fernandez-Ibanez, I. Oller, L. Prieto-Rodriguez, S. Miralles-Cuevas and Alejandro Cabrera-Reina5.1 Introduction 1615.2 Ozonation 1635.3 Membrane Processes 1655.4 Membrane Bioreactors (MBR) 1675.5 AOPs Including Solar AOPs 169References 1756 Transformation Products of Emerging Contaminants Formed during Advanced Oxidation Processes 179Ioannis K. Konstantinou, Dimitra A. Lambropoulou and Maria Antonopoulou6.1 Introduction 1796.2 Pesticides 1806.3 Phthalate Esters 2036.4 Pharmaceutical Compounds 2046.5 Others 2156.6 Conclusion 217Acknowledgments 218References 2187 Enzymatic Reactors Applied for the Biotransformation of Endocrine Disrupting Chemicals 229J.M. Lema, M.T. Moreira, G. Eibes, T. Lu-Chau, L. Lloret, R. Taboada, A. Arca-Ramos and G. Feijoo7.1 Endocrine Disrupting Chemicals 2297.2 White-Rot Fungi and Their Lignin Modifying Enzymes 2347.3 Enzymatic Reactors 2387.4 Determination of Transformation Products from the Enzymatic Treatment of EDCs 248References 2558 Biologically Mediated Chiral Inversion of Emerging Contaminants 261Stuart J. Khan8.1 Introduction 2618.3 Changes in Enantiomeric Composition During Biological Transformation Processes 2688.4 Evidence for Biologically Mediated Chiral Inversion 2718.5 Implications and Priorities for Future Research 274References 274PART III ANALYTICAL STRATEGIES 2819 Quality Issues in Water Sampling, Sample Pre-Treatment and Monitoring 283Sara Bogialli, Stefano Polesello and Sara Valsecchi9.1 Introduction 2839.2 Monitoring of Transformation Products in Water Bodies 2849.3 Sample Representativeness and Stability Issues 2879.4 Identification of Transformation Products and Legislative Requirements 2929.5 Conclusions 297References 29810 Transformation Products of Emerging Contaminants: Analytical Challenges and Future Needs 303B. Zonja, J. Acena, A. Jelic, M. Petrovic, S. Perez and D. Barcelo10.1 Introduction 30310.2 Generation, Detection and Identification of Transformation Products at Lab Scale: An Analytical Challenge 30510.3 Quantitative Analysis of TPs in the Environment 31110.4 Evaluation of the Toxicity of TPs 31810.5 Conclusions and Future Needs 319Acknowledgments 320References 32011 Advanced Mass Spectrometry-Based Techniques for the Identification and Structure Elucidation of Transformation Products of Emerging Contaminants 325Paola Calza and Fabbri Debora11.1 Introduction 32511.2 Potential and Differences Among the Different MS Systems for Determining Unknown Compounds 32611.3 How to Proceed in the Structural Attribution 33011.4 Accurate Mass Screening and Identification of Emerging Contaminants in Environmental Samples: Some Cases Studied 33411.5 Conclusions 345References 34612 Applications of NMR Techniques for the Identification and Structure Elucidation of Emerging Organic and Other Xenobiotic Organic Contaminants 351Alfred Preiss and Markus Godejohann12.1 Introduction 35112.2 Basic Techniques 35312.3 Applications 35912.4 Conclusions 377List of Abbreviations 377References 378Index 385 VOLUME 2PART IV OCCURRENCE, FATE AND EFFECTS IN THE ENVIRONMENT: AN OVERVIEW OF MAJOR CLASSES 38513 Transformation Products of Pesticides in the Environment: Analysis and Occurrence 387Ana Aguera Lopez, Marya del Mar Gomez Ramos, and Amadeo R. Fernandez-Alba13.1 Introduction 38713.2 Transformation of Pesticides in the Environment 38813.3 Analytical Techniques Used in the Identification and Analysis of TPs 40813.4 Occurrence of Pesticide TPs in the Environment 41813.5 Concluding Remarks 419Acknowledgments 420References 42014 Metabolites and Transformation Products of Pharmaceuticals in the Aquatic Environment as Contaminants of Emerging Concern 425I. Michael, M.I. Vasquez, E. Hapeshi, T. Haddad, E. Baginska, K. Kummerer, and D. Fatta-Kassinos14.1 Introduction 42514.2 Human Metabolites in the Aquatic Environment 42714.3 Biotransformation Products in the Aquatic Environment 43014.4 Transformation of Pharmaceuticals During Photolysis and Advanced Oxidation Processes 43714.5 Conclusions and Outlook 458Acknowledgments 459References 45915 Transformation Products of Personal Care Products: UV Filters Case Studies 471Kristina Pestotnik, Tina Kosjek, and Ester Heath15.1 Introduction 47115.2 Main Physico-Chemical Parameters of UV Filters and their Influence on Environmental Behaviour 47315.3 Occurrence of UV Filter Residues 47715.4 Fate of UV Filter Residues 47915.5 Analytical Methods for Identification of Transformation Products 49015.6 Effects and Toxicity of UV Filters and their Transformation Products in the Environment 49515.7 Conclusions and Future Strategies 498Acknowledgements 499Abbreviations 499References 50116 Transformation Products of Illicit Drugs 505Dimitra A. Lambropoulou and Eleni Evgenidou16.1 Introduction 50516.2 Fate and Treatment of IDs and Their Metabolites/TPs 50716.3 Analytical Methods and Detection 51516.4 Occurrence of IDs and their Metabolites/TPs in the Environment 51916.5 Ecotoxicity of IDs and Their Metabolites/TPs 52516.5.1 Sewage Epidemiology 52616.6 Concluding Remarks 527References 52717 Transformation Products of Artificial Sweeteners 537Marco Scheurer, Heinz-Jurgen Brauch, and Frank Thomas Lange17.1 Introduction 53717.2 Processes Leading to the Formation of Artificial Sweetener Transformation Products 53917.3 Summary and Conclusions 551References 55218 Transformation Products of Brominated Flame Retardants (BFRs) 557Alin C. Dirtu, Alin C. Ionas, Govindan Malarvannan, and Adrian Covaci18.1 Introduction 55718.2 Transformation Products of PBDEs 55818.3 Transformation Products of HBCDs 56918.4 Transformation Products of TBBPA 57318.5 Transformation Products of NBFRs 57818.6 Concluding Remarks and Future Perspectives 580Acknowledgements 580References 58119 Transformation Products of Alkylphenols 589Montserrat Cortina-Puig, Gabino Bolyvar-Subirats, Carlos Barata, and Silvia Lacorte19.1 Alkylphenols: Types, Properties and Uses 58919.2 Transformation of Alkylphenols and Identification of Transformation Products 59219.3 Occurrence of Alkylphenol Transformation Products in the Environment 60319.4 Risks and Effects of Alkylphenols and their Transformation Products in the Environment 61019.5 Conclusions 615Acknowledgments 616References 61620 Biotic and Abiotic Transformation Processes of Benzotriazoles: Possible Pathways and Products 625Dimitra Voutsa20.1 Introduction 62520.2 Biotic Degradation Processes 62720.3 Abiotic Transformation Processes 63120.4 Future Research Needs 634References 63421 Identification (Quantitative Determination and Detection) and Fate of Transformation Products of Rocket Fuel 1,1-Dimethylhydrazine 639Bulat Kenessov, Lars Carlsen21.1 Introduction/Background 63921.2 Identification of Transformation Products of 1,1-Dimethylhydrazine 64021.3 Distribution and Fate of Transformation Products of 1,1-Dimethylhydrazine in Soil at Fall Sites 64621.4 Analytical Methods Applied in the Monitoring 64721.5 Conclusion 656References 65722 Assessment of the Occurrence and Fate of Transformation Products of Endocrine Disrupting Compounds EDCs in the Environment 661Vasiliki Boti, Vasilios Sakkas, and Triantafyllos Albanis22.1 Introduction 66122.2 Endocrine Disrupting Compounds (EDCs) of Concern 66222.3 Environmental Fate and Transformation of EDCs 66422.4 Analytical Methodology 66622.5 Occurrence and Endocrine Disruption Effects of the TPs of Selected EDCs 67222.6 Future Needs –Recommendations 680References 68123 Transformation Products of Hazardous Cyanobacterial Metabolites in Water 687Anastasia Hiskia, Theodoros M. Triantis, Maria G. Antoniou, Armah A. de la Cruz, Kevin O'Shea, Weihua Song, Theodora Fotiou, Triantafyllos Kaloudis, Xuexiang He, Joel Andersen, and Dionysios D. Dionysiou23.1 Introduction 68823.2 Cyanobacterial Secondary Metabolites 68823.3 Transformation Products of Cyanobacterial Metabolites in Water 69423.4 Research Gaps, Recent Trends and Future Needs 710References 711PART V GLOBAL SPACIALITY AND ENVIRONMENTAL STATUS OF TRANSFORMATION PRODUCTS IN THE ENVIRONMENT 72124 Occurrence of Transformation Products of Emerging Contaminants in Water Resources 723Carlos GonScalves, Maria A.D. de Sousa, and Maria de Fatima Alpendurada24.1 Brief Introduction on the Sources of Transformation Products of Emerging Contaminants 72324.2 Transformation Products in Natural Waters: From Contamination Sources to Drinking Water Production 72524.3 Wastewaters as a Major Source of Transformation Products 74424.4 Origin and Presence of Transformation Products in Drinking Water 75024.5 Ubiquity and Regio-Specificity of Transformation Products 75224.6 Transformation Products of Emerging Contaminants: Fate and Behavior 75324.7 Conclusions 756References 75825 Occurrence of Transformation Products of Emerging Contaminants in Water Resources of the United States 763Imma Ferrer and E. Michael Thurman25.1 Introduction: Emerging Contaminants 76325.2 State-of-the-Art Techniques for the Identification of Emerging Contaminants and Their Transformation Products 76425.3 Use of Accurate Mass Tools for the Identification of Emerging Contaminants 76825.4 Occurrence of Transformation Products in Environmental Waters in the US 779References 78226 Spatial Modeling for Elucidation of Perfluorinated Compound Sources and Fate in a Watershed 787Yasuyuki Zushi and Shigeki Masunaga26.1 Introduction 78726.2 Source Identification of PFCs Using GIS 79226.3 Spatial Distribution of PFOS and PFOA Contributed by Nonpoint Sources 79826.4 Conclusion 804Acknowledgments 805References 80527 Global Distribution of Polyfluoroalkyl and Perfluoroalkyl Substances and their Transformation Products in Environmental Solids 809Holly Lee and Scott A. Mabury27.1 Introduction 80927.2 Global Contamination of PFASs in Environmental Solid Matrices 81327.3 Fate of PFASs in Environmental Solids 82127.4 Uptake into Vegetation 82727.5 Summary and Future Outlook 829References 830PART VI RISK ASSESSMENT, MANAGEMENT AND REGULATORY FRAMEWORK 83928 Toxicity and Risk of Transformation Products of Emerging Contaminants for Aquatic Organisms: Pharmaceutical Case Studies 841Marina DellaGreca, Marina Isidori, Fabio Temussi28.1 Introduction 84128.2 Photolysis in the Environment: Pharmaceutical Case Studies 84428.3 Effect-Driven Approach 84428.4 Exposure-Driven Approach 85328.5 Conclusion 867References 86829 Quantitative Structure–Activity Relationship/Quantitative Structure– Toxicity Relationship (QSAR/QSTR) Modeling as Tools for Assessing Effects and Predicting Risks of Transformation Products of Emerging Contaminants 871Lars Carlsen and Bulat Kenessov29.1 Introduction 87129.2 The Toolbox 87329.3 Environmental Behavior 87629.4 Ecotoxicological Effect 87929.5 Effects on Humans 88029.6 Conclusions 885References 88530 Steps Toward a Regulatory Framework for Transformation Products in Water 889Maria D. Hernando Guil, Maria J. Martýnez-Bueno, Laura Duran, Jose M. Navas and Amadeo R. Fernandez-Alba30.1 Introduction 88930.2 Scientific Advances and Technical Knowledge of Transformation Products. Relevant Cases of Study 89130.3 Toxicological Considerations in Assessing Mixtures of Chemicals and Significance of Transformation Products in EU Regulations. Interaction Between Regulatory Frameworks 906References 90831 NORMAN Association: A Network Approach to Scientific Collaboration on Emerging Contaminants and their Transformation Products in Europe 915Jaroslav Slobodnik and Valeria Dulio31.1 Introduction 91531.2 The NORMAN Network as a Science-to-Policy Interface 91731.3 Effect-Directed Analysis for Identification of Relevant Emerging Contaminants and their Transformation Products in Complex Environmental Samples 92131.4 Quality Control Aspects 92431.5 Conclusions 925Acknowledgements 926References 926PART VII OUTLOOK 92932 Outlook 93132.1 General Remarks 93132.2 Gaps, Recommendations and Future Needs 933Index 937