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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 3Jacek 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 65Marianne 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 89Davide 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 123Jose Benito Quintana, Rosario Rodil and Isaac Rodr©¥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 161Sixto 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 179Ioannis 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 229J.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 261Stuart 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 283Sara 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 303B. 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 325Paola 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 351Alfred 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 387Ana 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 425I. 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 471Kristina 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 505Dimitra 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 537Marco 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) 557Alin 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 589Montserrat 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 625Dimitra 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 639Bulat 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 661Vasiliki 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 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. 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 723Carlos 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 763Imma 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 787Yasuyuki 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 809Holly 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 841Marina 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 871Lars 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 889Maria D. Hernando Guil, Maria J. Martýnez-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 915Jaroslav 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
List of Contributors
Jaume Aceña, Department of Environmental Chemistry, IDAEA-CSIC, Spain
Ana Agüera López, Department of Chemistry and Physics, University of Almería, and CIESOL (Solar Energy Research Center), Joint Centre of the University of Almería-CIEMAT, Spain
Triantafyllos Albanis, Laboratory of Analytical Chemistry, Department of Chemistry, University of Ioannina, Greece
Joel Andersen, School of Energy, Environmental Biological and Medical Engineering, University of Cincinnati, USA
Maria G. Antoniou, Department of Environmental Science and Technology, Cyprus University of Technology, Cyprus
Maria Antonopoulou, Department of Environmental and Natural Resources Management, University of Patras, Greece
Adriana Arca-Ramos, Department of Chemical Engineering, University of Santiago de Compostela, Spain
Ewelina Baginska, Institute of Environmental Chemistry, Faculty for Sustainability, Leuphana University, Germany
Carlos Barata, Department of Environmental Chemistry, IDAEA-CSIC, Spain
Damià Barceló, Water and Soil Quality Research Group, IDAEA-CSIC, and Catalan Institute for Water Research (ICRA), Cientific and Technologic Park of Girona University, Spain
Sara Bogialli, Department of Chemistry, University of Padua, Italy
Gabino Bolívar-Subirats, Department of Environmental Chemistry, IDAEA-CSIC, Spain
Vasiliki Boti, Laboratory of Analytical Chemistry, Department of Chemistry, University of Ioannina, Greece
Heinz-Jürgen Brauch, DVGW Water Technology Center, Germany
Alejandro Cabrera-Reina, Department of Chemical Engineering, University of Almería, and CIESOL, Joint Centre of the University of Almería-CIEMAT, Spain
Paola Calza, Dipartimento di Chimica, Università di Torino, Italy
Lars Carlsen, Awareness Center, Denmark
Serge Chiron, UMR HydroSciences 5569, France
Monia Cieszyska, Department of Environmental Toxicology, Faculty of Health Sciences, Medical University of Gdansk, Poland
Montserrat Cortina-Puig, Escola Universitària Salesiana de Sarrià, Spain
Adrian Covaci, Toxicological Center, University of Antwerp, Belgium
Radosław Czernych, Department of Environmental Toxicology, Faculty of Health Sciences, Medical University of Gdansk, Poland
Maria de Fátima Alpendurada, IAREN – Water Institute of the Northern Region, and Faculty of Pharmacy, University of Porto, Portugal
Armah A. de la Cruz, Office of Research and Development, U.S. Environmental Protection Agency, USA
Maria A.D. de Sousa, IAREN – Water Institute of the Northern Region, and Department of Bromatology and Hydrology, Faculty of Pharmacy, University of Porto, Portugal
María del Mar Gómez Ramos, European Union Reference Laboratory (EURL), Department of Chemistry and Physics, University of Almería, Spain
Marina DellaGreca, Department of Chemical Sciences, University Federico II, Italy
Dionysios D. Dionysiou, School of Energy, Environmental Biological and Medical Engineering, University of Cincinnati, USA
Alin C. Dirtu, Toxicological Center, University of Antwerp, Belgium
Valeria Dulio, INERIS, National Institute for the Environment and Industrial Risks, France
Laura Duran, Parque Científico Tecnológico, University of Alcalá, Spain
Gemma Eibes, Department of Chemical Engineering, University of Santiago de Compostela, Spain
Eleni Evgenidou, Department of Chemistry, Aristotle University of Thessaloniki, Greece
Debora Fabbri, Dipartimento di Chimica, Università di Torino, Italy
Despo Fatta-Kassinos, Department of Civil and Environmental Engineering, and NIREAS, International Water Research Centre, University of Cyprus, Cyprus
Gumersindo Feijoo, Department of Chemical Engineering, University of Santiago de Compostela, Spain
Amadeo R. Fernández-Alba, Department of Chemistry and Physics, University of Almería, and CIESOL (Solar Energy Research Center), Joint Centre of the University of Almería-CIEMAT, and European Union Reference Laboratory (EURL), Department of Chemistry and Physics, University of Almería, Spain
Pilar Fernández-Ibáñez, Plataforma Solar de Almería (CIEMAT), and CIESOL, Joint Centre of the University of Almería-CIEMAT, Spain
Imma Ferrer, Center for Environmental Mass Spectrometry, University of Colorado, USA
Theodora Fotiou, Institute of Advanced Materials, Physicochemical Processes, Nanotechnology and Microsystems, National Center for Scientific Research “Demokritos”, Greece
Grayna Gałziowska, Department of Environmental Toxicology, Faculty of Health Sciences, Medical University of Gdansk, Poland
Markus Godejohann, Bruker BioSpin, Germany
Carlos Gonçalves, IAREN – Water Institute of the Northern Region, Portugal
Tarek Haddad, Institute of Environmental Chemistry, Faculty for Sustainability, Leuphana University, Germany
Evroula Hapeshi, Department of Civil and Environmental Engineering, and NIREAS, International Water Research Centre, University of Cyprus, Cyprus
Xuexiang He, School of Energy, Environmental Biological and Medical Engineering, University of Cincinnati, USA
Ester Heath, “Jožef Stefan” Institute, Department of Environmental Sciences, and “Jožef Stefan” International Postgraduate School, Slovenia
Maria D. Hernando Guil, Spanish National Institute for Agricultural and Food Research and Technology, INIA, Spain
Anastasia Hiskia, Institute of Advanced Materials, Physicochemical Processes, Nanotechnology and Microsystems, National Center for Scientific Research “Demokritos”, Greece
Alin C. Ionas, Toxicological Center, University of Antwerp, Belgium
Marina Isidori, Department of Environmental, Biological and Pharmaceutical Sciences and Technologies, Seconda Università di Napoli, Italy
Aleksandra Jelic, Department of Environmental Chemistry, IDAEA-CSIC, Spain
Triantafyllos Kaloudis, Athens Water Supply and Sewerage Company (EYDAP SA), Organic Micropollutants Laboratory, Greece
Bulat Kenessov, Center of Physical Chemical Methods of Research and Analysis, al-Farabi Kazakh National University, Kazakhstan
Stuart J. Khan, UNSW Water Research Centre, School of Civil & Environmental Engineering, University of New South Wales, Australia
Ioannis K. Konstantinou, Department of Environmental and Natural Resources Management, University of Patras, Greece
Tina Kosjek, “Jožef Stefan” Institute, Department of Environmental Sciences, Slovenia
Klaus Kümmerer, Institute of Environmental Chemistry, Faculty for Sustainability, Leuphana University, Germany
Silvia Lacorte, Department of Environmental Chemistry, IDAEA-CSIC, Spain
Dimitra A. Lambropoulou, Environmental Pollution Control Laboratory, Department of Chemistry, Aristotle University of Thessaloniki, Greece
Dan J. Lapworth, British Geological Survey, UK
Holly Lee, Department of Chemistry, University of Toronto, Canada
Juan M. Lema Rodicio, Department of Chemical Engineering, University of Santiago de Compostela, Spain
Lucía Lloret, Department of Chemical Engineering, University of Santiago de Compostela, Spain
Thelmo A. Lu-Chau, Department of Chemical Engineering, University of Santiago de Compostela, Spain
Scott A. Mabury, Department of Chemistry, University of Toronto, Canada
Govindan Malarvannan, Toxicological Center, University of Antwerp, Belgium
Sixto Malato, Plataforma Solar de Almería (CIEMAT), and CIESOL, Joint Centre of the University of Almería-CIEMAT, Spain
Maria J. Martínez-Bueno, Department of Hydrogeology and Analytical Chemistry, University of Almería, Spain
Shigeki Masunaga, Graduate School of Environment and Information Sciences, Yokohama National University, Japan
Irene Michael, Department of Civil and Environmental Engineering, and NIREAS, International Water Research Centre, University of Cyprus, Cyprus
Sara Miralles-Cuevas, Plataforma Solar de Almería (CIEMAT), and CIESOL, Joint Centre of the University of Almería-CIEMAT, Spain
Ma Teresa Moreira, Department of Chemical Engineering, University of Santiago de Compostela, Spain
Jacek Namienik, Department of Analytical Chemistry, Faculty of Chemistry, Gdansk University of Technology, Poland
José M. Navas, Department of Hydrogeology and Analytical Chemistry, University of Almería, Spain
Leo M.L....
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