Transformation products of emerging contaminants in the environment : analysis, processes, occurrence, effects and risks. Volume 2

Content: Preface xiii     List of Contributors xv     VOLUME 1     PART I GENERAL CONSIDERATIONS 1     1 Classifying the Transformation Products (TPs) of Emerging Contaminants (ECs) for Prioritizing Research into their Impact on the Environment and Human Health 3  Jacek Namiesnik, Lidia Wolska, Radosaw Czernych, Grazyna Gaeziowska and Monia Cieszynska     1.1 Introduction 3     1.2 Emerging Contaminants     Emerging Problem 5     1.3 Transformation Products of ECs 41     1.4 Minimizing Environmental Risk of ECs and their TPs 43     1.5 Concluding Remarks and Future Perspectives 45     References 49     2 Transformation Products of Emerging Organic Compounds as Future Groundwater and Drinking Water Contaminants 65  Marianne E. Stuart and Dan J. Lapworth     2.1 Introduction 65     2.2 Sources and Pathways of Emerging Contaminants to Groundwater 66     2.3 Persistence in the Groundwater Environment 68     2.4 Emerging Contaminants and their Transformation Products in Groundwater 69     2.5 Toxicity and Risk Assessment 76     2.6 Conclusions 78     References 79     PART II TRANSFORMATION PROCESSES AND TREATMENT STRATEGIES 87     3 Phototransformation Processes of Emerging Contaminants in Surface Water 89  Davide Vione and Serge Chiron     3.1 Introduction 89     3.2 Direct Photolysis and Sensitised Reactions in the Transformation of Emerging Contaminants 90     3.3 The Case of Photonitration 104     3.4 Towards the Modelling of Phototransformation Kinetics in Surface Water 106     References 118     4 Transformation Products of Emerging Contaminants upon Reaction with Conventional Water Disinfection Oxidants 123  Jose Benito Quintana, Rosario Rodil and Isaac Rodr(c)[yen]guez     4.1 Introduction 123     4.2 Analytical Methodology for Transformation Products Identification 124     4.3 Factors Influencing the Kinetics of Chlorination 131     4.4 Overview of Typical Reaction Mechanisms During Free Chlorine Treatments 135     4.5 Review of Current Knowledge of Emerging Pollutant Reactions with Free Chlorine 138     4.6 Other Disinfection Agents 150     4.7 Conclusions and Outlook 155     References 155     5 Approaches to Water andWastewater Treatment for Removal of Emerging Contaminants: Ongoing Research and Recommendations for Future Work 161  Sixto Malato, P. Fernandez-Ibanez, I. Oller, L. Prieto-Rodriguez, S. Miralles-Cuevas and Alejandro Cabrera-Reina     5.1 Introduction 161     5.2 Ozonation 163     5.3 Membrane Processes 165     5.4 Membrane Bioreactors (MBR) 167     5.5 AOPs Including Solar AOPs 169     References 175     6 Transformation Products of Emerging Contaminants Formed during Advanced Oxidation Processes 179  Ioannis K. Konstantinou, Dimitra A. Lambropoulou and Maria Antonopoulou     6.1 Introduction 179     6.2 Pesticides 180     6.3 Phthalate Esters 203     6.4 Pharmaceutical Compounds 204     6.5 Others 215     6.6 Conclusion 217     Acknowledgments 218     References 218     7 Enzymatic Reactors Applied for the Biotransformation of Endocrine Disrupting Chemicals 229  J.M. Lema, M.T. Moreira, G. Eibes, T. Lu-Chau, L. Lloret, R. Taboada, A. Arca-Ramos and G. Feijoo     7.1 Endocrine Disrupting Chemicals 229     7.2 White-Rot Fungi and Their Lignin Modifying Enzymes 234     7.3 Enzymatic Reactors 238     7.4 Determination of Transformation Products from the Enzymatic Treatment of EDCs 248     References 255     8 Biologically Mediated Chiral Inversion of Emerging Contaminants 261  Stuart J. Khan     8.1 Introduction 261     8.3 Changes in Enantiomeric Composition During Biological Transformation Processes 268     8.4 Evidence for Biologically Mediated Chiral Inversion 271     8.5 Implications and Priorities for Future Research 274     References 274     PART III ANALYTICAL STRATEGIES 281     9 Quality Issues in Water Sampling, Sample Pre-Treatment and Monitoring 283  Sara Bogialli, Stefano Polesello and Sara Valsecchi     9.1 Introduction 283     9.2 Monitoring of Transformation Products in Water Bodies 284     9.3 Sample Representativeness and Stability Issues 287     9.4 Identification of Transformation Products and Legislative Requirements 292     9.5 Conclusions 297     References 298     10 Transformation Products of Emerging Contaminants: Analytical Challenges and Future Needs 303  B. Zonja, J. Acena, A. Jelic, M. Petrovic, S. Perez and D. Barcelo     10.1 Introduction 303     10.2 Generation, Detection and Identification of Transformation Products at Lab Scale: An Analytical Challenge 305     10.3 Quantitative Analysis of TPs in the Environment 311     10.4 Evaluation of the Toxicity of TPs 318     10.5 Conclusions and Future Needs 319     Acknowledgments 320     References 320     11 Advanced Mass Spectrometry-Based Techniques for the Identification and Structure Elucidation of Transformation Products of Emerging Contaminants 325  Paola Calza and Fabbri Debora     11.1 Introduction 325     11.2 Potential and Differences Among the Different MS Systems for Determining Unknown Compounds 326     11.3 How to Proceed in the Structural Attribution 330     11.4 Accurate Mass Screening and Identification of Emerging Contaminants in Environmental Samples: Some Cases Studied 334     11.5 Conclusions 345     References 346     12 Applications of NMR Techniques for the Identification and Structure Elucidation of Emerging Organic and Other Xenobiotic Organic Contaminants 351  Alfred Preiss and Markus Godejohann     12.1 Introduction 351     12.2 Basic Techniques 353     12.3 Applications 359     12.4 Conclusions 377     List of Abbreviations 377     References 378     Index 385         VOLUME 2     PART IV OCCURRENCE, FATE AND EFFECTS IN THE ENVIRONMENT: AN OVERVIEW OF MAJOR CLASSES 385     13 Transformation Products of Pesticides in the Environment: Analysis and Occurrence 387  Ana Aguera Lopez, Marya del Mar Gomez Ramos, and Amadeo R. Fernandez-Alba     13.1 Introduction 387     13.2 Transformation of Pesticides in the Environment 388     13.3 Analytical Techniques Used in the Identification and Analysis of TPs 408     13.4 Occurrence of Pesticide TPs in the Environment 418     13.5 Concluding Remarks 419     Acknowledgments 420     References 420     14 Metabolites and Transformation Products of Pharmaceuticals in the Aquatic Environment as Contaminants of Emerging Concern 425  I. Michael, M.I. Vasquez, E. Hapeshi, T. Haddad, E. Baginska, K. Kummerer, and D. Fatta-Kassinos     14.1 Introduction 425     14.2 Human Metabolites in the Aquatic Environment 427     14.3 Biotransformation Products in the Aquatic Environment 430     14.4 Transformation of Pharmaceuticals During Photolysis and Advanced Oxidation Processes 437     14.5 Conclusions and Outlook 458     Acknowledgments 459     References 459     15 Transformation Products of Personal Care Products: UV Filters Case Studies 471  Kristina Pestotnik, Tina Kosjek, and Ester Heath     15.1 Introduction 471     15.2 Main Physico-Chemical Parameters of UV Filters and their Influence on Environmental Behaviour 473     15.3 Occurrence of UV Filter Residues 477     15.4 Fate of UV Filter Residues 479     15.5 Analytical Methods for Identification of Transformation Products 490     15.6 Effects and Toxicity of UV Filters and their Transformation Products in the Environment 495     15.7 Conclusions and Future Strategies 498     Acknowledgements 499     Abbreviations 499     References 501     16 Transformation Products of Illicit Drugs 505  Dimitra A. Lambropoulou and Eleni Evgenidou     16.1 Introduction 505     16.2 Fate and Treatment of IDs and Their Metabolites/TPs 507     16.3 Analytical Methods and Detection 515     16.4 Occurrence of IDs and their Metabolites/TPs in the Environment 519     16.5 Ecotoxicity of IDs and Their Metabolites/TPs 525     16.5.1 Sewage Epidemiology 526     16.6 Concluding Remarks 527     References 527     17 Transformation Products of Artificial Sweeteners 537  Marco Scheurer, Heinz-Jurgen Brauch, and Frank Thomas Lange     17.1 Introduction 537     17.2 Processes Leading to the Formation of Artificial Sweetener Transformation Products 539     17.3 Summary and Conclusions 551     References 552     18 Transformation Products of Brominated Flame Retardants (BFRs) 557  Alin C. Dirtu, Alin C. Ionas, Govindan Malarvannan, and Adrian Covaci     18.1 Introduction 557     18.2 Transformation Products of PBDEs 558     18.3 Transformation Products of HBCDs 569     18.4 Transformation Products of TBBPA 573     18.5 Transformation Products of NBFRs 578     18.6 Concluding Remarks and Future Perspectives 580     Acknowledgements 580     References 581     19 Transformation Products of Alkylphenols 589  Montserrat Cortina-Puig, Gabino Bolyvar-Subirats, Carlos Barata, and Silvia Lacorte     19.1 Alkylphenols: Types, Properties and Uses 589     19.2 Transformation of Alkylphenols and Identification of Transformation Products 592     19.3 Occurrence of Alkylphenol Transformation Products in the Environment 603     19.4 Risks and Effects of Alkylphenols and their Transformation Products in the Environment 610     19.5 Conclusions 615     Acknowledgments 616     References 616     20 Biotic and Abiotic Transformation Processes of Benzotriazoles: Possible Pathways and Products 625  Dimitra Voutsa     20.1 Introduction 625     20.2 Biotic Degradation Processes 627     20.3 Abiotic Transformation Processes 631     20.4 Future Research Needs 634     References 634     21 Identification (Quantitative Determination and Detection) and Fate of Transformation Products of Rocket Fuel 1,1-Dimethylhydrazine 639  Bulat Kenessov, Lars Carlsen     21.1 Introduction/Background 639     21.2 Identification of Transformation Products of 1,1-Dimethylhydrazine 640     21.3 Distribution and Fate of Transformation Products of 1,1-Dimethylhydrazine in Soil at Fall Sites 646     21.4 Analytical Methods Applied in the Monitoring 647     21.5 Conclusion 656     References 657     22 Assessment of the Occurrence and Fate of Transformation Products of Endocrine Disrupting Compounds EDCs in the Environment 661  Vasiliki Boti, Vasilios Sakkas, and Triantafyllos Albanis     22.1 Introduction 661     22.2 Endocrine Disrupting Compounds (EDCs) of Concern 662     22.3 Environmental Fate and Transformation of EDCs 664     22.4 Analytical Methodology 666     22.5 Occurrence and Endocrine Disruption Effects of the TPs of Selected EDCs 672     22.6 Future Needs    Recommendations 680     References 681     23 Transformation Products of Hazardous Cyanobacterial Metabolites in Water 687  Anastasia 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. Dionysiou     23.1 Introduction 688     23.2 Cyanobacterial Secondary Metabolites 688     23.3 Transformation Products of Cyanobacterial Metabolites in Water 694     23.4 Research Gaps, Recent Trends and Future Needs 710     References 711     PART V GLOBAL SPACIALITY AND ENVIRONMENTAL STATUS OF TRANSFORMATION PRODUCTS IN THE ENVIRONMENT 721     24 Occurrence of Transformation Products of Emerging Contaminants in Water Resources 723  Carlos GonScalves, Maria A.D. de Sousa, and Maria de Fatima Alpendurada     24.1 Brief Introduction on the Sources of Transformation Products of Emerging Contaminants 723     24.2 Transformation Products in Natural Waters: From Contamination Sources to Drinking Water Production 725     24.3 Wastewaters as a Major Source of Transformation Products 744     24.4 Origin and Presence of Transformation Products in Drinking Water 750     24.5 Ubiquity and Regio-Specificity of Transformation Products 752     24.6 Transformation Products of Emerging Contaminants: Fate and Behavior 753     24.7 Conclusions 756     References 758     25 Occurrence of Transformation Products of Emerging Contaminants in Water Resources of the United States 763  Imma Ferrer and E. Michael Thurman     25.1 Introduction: Emerging Contaminants 763     25.2 State-of-the-Art Techniques for the Identification of Emerging Contaminants and Their Transformation Products 764     25.3 Use of Accurate Mass Tools for the Identification of Emerging Contaminants 768     25.4 Occurrence of Transformation Products in Environmental Waters in the US 779     References 782     26 Spatial Modeling for Elucidation of Perfluorinated Compound Sources and Fate in a Watershed 787  Yasuyuki Zushi and Shigeki Masunaga     26.1 Introduction 787     26.2 Source Identification of PFCs Using GIS 792     26.3 Spatial Distribution of PFOS and PFOA Contributed by Nonpoint Sources 798     26.4 Conclusion 804     Acknowledgments 805     References 805     27 Global Distribution of Polyfluoroalkyl and Perfluoroalkyl Substances and their Transformation Products in Environmental Solids 809  Holly Lee and Scott A. Mabury     27.1 Introduction 809     27.2 Global Contamination of PFASs in Environmental Solid Matrices 813     27.3 Fate of PFASs in Environmental Solids 821     27.4 Uptake into Vegetation 827     27.5 Summary and Future Outlook 829     References 830     PART VI RISK ASSESSMENT, MANAGEMENT AND REGULATORY FRAMEWORK 839     28 Toxicity and Risk of Transformation Products of Emerging Contaminants for Aquatic Organisms: Pharmaceutical Case Studies 841  Marina DellaGreca, Marina Isidori, Fabio Temussi     28.1 Introduction 841     28.2 Photolysis in the Environment: Pharmaceutical Case Studies 844     28.3 Effect-Driven Approach 844     28.4 Exposure-Driven Approach 853     28.5 Conclusion 867     References 868     29 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 871  Lars Carlsen and Bulat Kenessov     29.1 Introduction 871     29.2 The Toolbox 873     29.3 Environmental Behavior 876     29.4 Ecotoxicological Effect 879     29.5 Effects on Humans 880     29.6 Conclusions 885     References 885     30 Steps Toward a Regulatory Framework for Transformation Products in Water 889  Maria D. Hernando Guil, Maria J. Martynez-Bueno, Laura Duran, Jose M. Navas and Amadeo R. Fernandez-Alba     30.1 Introduction 889     30.2 Scientific Advances and Technical Knowledge of Transformation Products. Relevant Cases of Study 891     30.3 Toxicological Considerations in Assessing Mixtures of Chemicals and Significance of Transformation Products in EU Regulations. Interaction Between Regulatory Frameworks 906     References 908     31 NORMAN Association: A Network Approach to Scientific Collaboration on Emerging Contaminants and their Transformation Products in Europe 915  Jaroslav Slobodnik and Valeria Dulio     31.1 Introduction 915     31.2 The NORMAN Network as a Science-to-Policy Interface 917     31.3 Effect-Directed Analysis for Identification of Relevant Emerging Contaminants and their Transformation Products in Complex Environmental Samples 921     31.4 Quality Control Aspects 924     31.5 Conclusions 925     Acknowledgements 926     References 926     PART VII OUTLOOK 929     32 Outlook 931     32.1 General Remarks 931     32.2 Gaps, Recommendations and Future Needs 933     Index 937