ISBN-10:
1118339592
ISBN-13:
9781118339596
Pub. Date:
03/10/2014
Publisher:
Wiley
Transformation Products of Emerging Contaminants in the Environment: Analysis, Processes, Occurrence, Effects and Risks / Edition 1

Transformation Products of Emerging Contaminants in the Environment: Analysis, Processes, Occurrence, Effects and Risks / Edition 1

by Dimitra A. Lambropoulou, Leo M. L. Nollet

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Product Details

ISBN-13: 9781118339596
Publisher: Wiley
Publication date: 03/10/2014
Pages: 964
Product dimensions: 7.30(w) x 10.20(h) x 2.50(d)

About the Author

Editors

Dimitra A. Lambropoulou Department of Chemistry, Aristotle University of Thessaloniki, Greece

Leo M. L. Nollet Emeritus, Faculty of Applied Engineering Sciences, University College Ghent, Belgium

Table of Contents

Preface xiii

List of Contributors xv

VOLUME 1

PART I GENERAL CONSIDERATIONS 1

1 Classifying the Transformation Products (TPs) of EmergingContaminants (ECs) for Prioritizing Research into their Impact onthe Environment and Human Health 3
Jacek Namiesnik, Lidia Wolska, Radosaw Czernych, GrazynaGaeziowska 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 asFuture 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 Groundwater66

2.3 Persistence in the Groundwater Environment 68

2.4 Emerging Contaminants and their Transformation Products inGroundwater 69

2.5 Toxicity and Risk Assessment 76

2.6 Conclusions 78

References 79

PART II TRANSFORMATION PROCESSES AND TREATMENT STRATEGIES87

3 Phototransformation Processes of Emerging Contaminants inSurface Water 89
Davide Vione and Serge Chiron

3.1 Introduction 89

3.2 Direct Photolysis and Sensitised Reactions in theTransformation of Emerging Contaminants 90

3.3 The Case of Photonitration 104

3.4 Towards the Modelling of Phototransformation Kinetics inSurface Water 106

References 118

4 Transformation Products of Emerging Contaminants upon Reactionwith Conventional Water Disinfection Oxidants 123
Jose Benito Quintana, Rosario Rodil and IsaacRodríguez

4.1 Introduction 123

4.2 Analytical Methodology for Transformation ProductsIdentification 124

4.3 Factors Influencing the Kinetics of Chlorination 131

4.4 Overview of Typical Reaction Mechanisms During Free ChlorineTreatments 135

4.5 Review of Current Knowledge of Emerging Pollutant Reactionswith 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 ofEmerging Contaminants: Ongoing Research and Recommendations forFuture Work 161
Sixto Malato, P. Fernandez-Ibanez, I. Oller, L.Prieto-Rodriguez, S. Miralles-Cuevas and AlejandroCabrera-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 duringAdvanced Oxidation Processes 179
Ioannis K. Konstantinou, Dimitra A. Lambropoulou and MariaAntonopoulou

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 ofEndocrine 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 EnzymaticTreatment of EDCs 248

References 255

8 Biologically Mediated Chiral Inversion of EmergingContaminants 261
Stuart J. Khan

8.1 Introduction 261

8.3 Changes in Enantiomeric Composition During BiologicalTransformation 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 andMonitoring 283
Sara Bogialli, Stefano Polesello and Sara Valsecchi

9.1 Introduction 283

9.2 Monitoring of Transformation Products in Water Bodies284

9.3 Sample Representativeness and Stability Issues 287

9.4 Identification of Transformation Products and LegislativeRequirements 292

9.5 Conclusions 297

References 298

10 Transformation Products of Emerging Contaminants: AnalyticalChallenges 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 TransformationProducts 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 theIdentification and Structure Elucidation of Transformation Productsof Emerging Contaminants 325
Paola Calza and Fabbri Debora

11.1 Introduction 325

11.2 Potential and Differences Among the Different MS Systemsfor Determining Unknown Compounds 326

11.3 How to Proceed in the Structural Attribution 330

11.4 Accurate Mass Screening and Identification of EmergingContaminants in Environmental Samples: Some Cases Studied 334

11.5 Conclusions 345

References 346

12 Applications of NMR Techniques for the Identification andStructure Elucidation of Emerging Organic and Other XenobioticOrganic 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 andAnalysis 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 inthe Aquatic Environment as Contaminants of Emerging Concern425
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 Environment430

14.4 Transformation of Pharmaceuticals During Photolysis andAdvanced Oxidation Processes 437

14.5 Conclusions and Outlook 458

Acknowledgments 459

References 459

15 Transformation Products of Personal Care Products: UV FiltersCase Studies 471
Kristina Pestotnik, Tina Kosjek, and Ester Heath

15.1 Introduction 471

15.2 Main Physico-Chemical Parameters of UV Filters and theirInfluence 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 TransformationProducts 490

15.6 Effects and Toxicity of UV Filters and their TransformationProducts 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 theEnvironment 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 ThomasLange

17.1 Introduction 537

17.2 Processes Leading to the Formation of Artificial SweetenerTransformation 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 AdrianCovaci

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 ofTransformation Products 592

19.3 Occurrence of Alkylphenol Transformation Products in theEnvironment 603

19.4 Risks and Effects of Alkylphenols and their TransformationProducts in the Environment 610

19.5 Conclusions 615

Acknowledgments 616

References 616

20 Biotic and Abiotic Transformation Processes ofBenzotriazoles: 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) andFate of Transformation Products of Rocket Fuel1,1-Dimethylhydrazine 639
Bulat Kenessov, Lars Carlsen

21.1 Introduction/Background 639

21.2 Identification of Transformation Products of1,1-Dimethylhydrazine 640

21.3 Distribution and Fate of Transformation Products of1,1-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 TransformationProducts of Endocrine Disrupting Compounds EDCs in the Environment661
Vasiliki Boti, Vasilios Sakkas, and TriantafyllosAlbanis

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 ofSelected EDCs 672

22.6 Future Needs –Recommendations 680

References 681

23 Transformation Products of Hazardous CyanobacterialMetabolites 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 DionysiosD. Dionysiou

23.1 Introduction 688

23.2 Cyanobacterial Secondary Metabolites 688

23.3 Transformation Products of Cyanobacterial Metabolites inWater 694

23.4 Research Gaps, Recent Trends and Future Needs 710

References 711

PART V GLOBAL SPACIALITY AND ENVIRONMENTAL STATUS OFTRANSFORMATION PRODUCTS IN THE ENVIRONMENT 721

24 Occurrence of Transformation Products of EmergingContaminants in Water Resources 723
Carlos GonScalves, Maria A.D. de Sousa, and Maria de FatimaAlpendurada

24.1 Brief Introduction on the Sources of TransformationProducts of Emerging Contaminants 723

24.2 Transformation Products in Natural Waters: FromContamination Sources to Drinking Water Production 725

24.3 Wastewaters as a Major Source of Transformation Products744

24.4 Origin and Presence of Transformation Products in DrinkingWater 750

24.5 Ubiquity and Regio-Specificity of Transformation Products752

24.6 Transformation Products of Emerging Contaminants: Fate andBehavior 753

24.7 Conclusions 756

References 758

25 Occurrence of Transformation Products of EmergingContaminants 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 ofEmerging Contaminants and Their Transformation Products 764

25.3 Use of Accurate Mass Tools for the Identification ofEmerging Contaminants 768

25.4 Occurrence of Transformation Products in EnvironmentalWaters in the US 779

References 782

26 Spatial Modeling for Elucidation of Perfluorinated CompoundSources 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 byNonpoint Sources 798

26.4 Conclusion 804

Acknowledgments 805

References 805

27 Global Distribution of Polyfluoroalkyl and PerfluoroalkylSubstances and their Transformation Products in EnvironmentalSolids 809
Holly Lee and Scott A. Mabury

27.1 Introduction 809

27.2 Global Contamination of PFASs in Environmental SolidMatrices 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 FRAMEWORK839

28 Toxicity and Risk of Transformation Products of EmergingContaminants for Aquatic Organisms: Pharmaceutical Case Studies841
Marina DellaGreca, Marina Isidori, Fabio Temussi

28.1 Introduction 841

28.2 Photolysis in the Environment: Pharmaceutical Case Studies844

28.3 Effect-Driven Approach 844

28.4 Exposure-Driven Approach 853

28.5 Conclusion 867

References 868

29 Quantitative Structure–ActivityRelationship/Quantitative Structure– Toxicity Relationship(QSAR/QSTR) Modeling as Tools for Assessing Effects and PredictingRisks 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 TransformationProducts in Water 889
Maria D. Hernando Guil, Maria J. Martínez-Bueno, LauraDuran, Jose M. Navas and Amadeo R. Fernandez-Alba

30.1 Introduction 889

30.2 Scientific Advances and Technical Knowledge ofTransformation Products. Relevant Cases of Study 891

30.3 Toxicological Considerations in Assessing Mixtures ofChemicals and Significance of Transformation Products in EURegulations. Interaction Between Regulatory Frameworks 906

References 908

31 NORMAN Association: A Network Approach to ScientificCollaboration on Emerging Contaminants and their TransformationProducts 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 RelevantEmerging Contaminants and their Transformation Products in ComplexEnvironmental 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

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