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T WO

VOLUM E

SE T

Tran

sformation

Produ

cts of Em

erging

Con

tamin

ants in

the E

nviron

men

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Editors

Lambropoulou

Nollet

Transformation Products of Emerging Contaminants in the Environment

Analysis, Processes, Occurrence,

Effects and Risks

Editors

Dimitra A. Lambropoulou

Leo M. L. Nollet

T WO VO LU M E SE TT WO VOLUM E SE TTransformation Products of Emerging Contaminants in the EnvironmentAnalysis, Processes, Occurrence, Effects and Risks

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

Over the last 15 years, the focus of chemical pollution has shifted fromconventional pollutants to so-called “emerging” or “new” unregulatedcontaminants. These include pharmaceuticals and personal care products, hormones, UV fi lters, perfl uorinated compounds, poylybrominated fl ameretardants (BFRs), pesticides, plasticizers, artifi cial sweeteners, illicit drugs, and endocrine disruptor compounds (EDCs). Despite the increasing numberof published studies covering emerging contaminants, we know almostnothing about the effects of their transformation products and/or metabolites.

This two-volume set provides a unique collection of research on transformationproducts, their occurrence, fate and risks in the environment. It contains32 chapters, organised into 7 parts, each with a distinct focus:

• General Considerations • Transformation Processes and Treatment Strategies • Analytical Strategies • Occurrence, Fate and Effects in the Environment • Global Speciality and Environmental Status • Risk Assessment, Management and Regulatory Framework • OutlookTransformation Products of Emerging Contaminants in the Environment is a valuable resource for researchers and industry professionals in environmentalchemistry, analytical chemistry, ecotoxicology, environmental sciences, and hydrology, as well as environmental consultants and regulatory bodies.

RED BOX RULES ARE FOR PROOF STAGE ONLY. DELETE BEFORE FINAL PRINTING.

Transformation Products of Emerging

Contaminants in the Environment

Transformation Products of EmergingContaminants in the Environment

Analysis, Processes, Occurrence,Effects and Risks

EDITED BY

DIMITRA A. LAMBROPOULOU AND LEOM. L. NOLLET

This edit ion first published 2014

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Library of Congress Cataloging-in-Publication Data

Transformation products of emerging contaminants in the environment :

analysis, processes, occurrence, effects and risks / edited by Leo M.L. Nollet

and Dimitra A. Lambropoulou.

pages cm

Includes index.

ISBN 978-1-118-33959-6 (cloth)

1. Chemicals–Environmental aspects. 2. Speciation (Chemistry) 3.

Pollutants–Biodegradation. 4. Environmental chemistry. I. Nollet, Leo M.

L., 1948- editor. II. Lambropoulou, Dimitra A., editor.

TD196.C45T728 2014

363.73804–dc232013022173

A catalogue record for this book is available from the British Library.

ISBN:9781118339596 (13 digits)

Set in 10/12 pt Times by Thomson Digital, Noida, India

http://www.wiley.com

I would also like to offer my heartfelt thanks to my co-editor Leo,

who generously shared his distinguished expertise with me,while

serving as peer respondent during this editorship. I’m really

touched by his kind words and thoughts and I feel very grateful

for this wonderful collaboration. I am very happy to look

forward to working with him again.

Dimitra A. Lambropoulou

For a fine collaboration during the redaction period of this book

I like to thank my co-editor Dimitra. I hope she will continue to

be a well appreciated scientist. I hope we will able cooperate in a

number of future projects.

Leo M.L. Nollet

Contents

Preface xxi

List of Contributors xxiii

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 Namie�snik, Lidia Wolska, Radosław Czernych, Gra _zyna Gałęzowskaand Monika Cieszy�nska

1.1 Introduction 3

1.2 Emerging Contaminants – Emerging Problem 5

1.2.1 Veterinary and Human Antibiotics 6

1.2.2 Human Drugs 6

1.2.3 Industrial and Household Wastewater Products 8

1.2.4 Sex and Steroidal Hormones 40

1.3 Transformation Products of ECs 41

1.3.1 Veterinary and Human Antibiotics 41

1.3.2 Human Drugs 41

1.3.3 Industrial and Household Wastewater Products 42

1.3.4 Sex and Steroidal Hormones 42

1.4 Minimizing Environmental Risk of ECs and their TPs 43

1.4.1 Designing a Risk Minimization Strategy 43

1.4.2 Results of the Prioritization Procedure 45

1.5 Concluding Remarks and Future Perspectives 45

References 49

2 Transformation Products of Emerging Organic Compoundsas 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

2.4.1 Pesticides 69

2.4.2 Pharmaceuticals 71

2.4.3 Personal Care Products and Synthetic Musks 73

2.4.4 Caffeine and Nicotine 73

2.4.5 Alkylphenols and Other Endocrine Disruptors 73

2.4.6 Disinfection By-Products 74

2.4.7 Brominated and Fluorinated Compounds 75

2.4.8 Triazoles 75

2.4.9 Naphthenic Acids 76

2.4.10 Explosive Residues 76

2.4.11 Algal Toxins 76

2.5 Toxicity and Risk Assessment 76

2.6 Conclusions 78

References 79

PART II TRANSFORMATION PROCESSES AND TREATMENTSTRATEGIES 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

3.2.1 Direct Photolysis 90

3.2.2 Reaction with �OH 96

3.2.3 Reaction with CO3�� 100

3.2.4 Reaction with 3CDOM� 1023.2.5 Reaction with 1O2 103

3.3 The Case of Photonitration 104

3.4 Towards the Modelling of Phototransformation Kinetics in Surface Water 106

3.4.1 Surface-Water Absorption Spectrum 108

3.4.2 Reaction with �OH 108

3.4.3 Direct Photolysis 111

3.4.4 Reaction with CO3�� 112

3.4.5 Reaction with 1O2 113

3.4.6 Reaction with 3CDOM� 1143.4.7 Photochemical Transformation of Organic Pollutants 114

3.4.8 Photo-Transformation of Intermediates 117

References 118

4 Transformation Products of Emerging Contaminants upon Reaction

with Conventional Water Disinfection Oxidants 123

Jos�e Benito Quintana, Rosario Rodil and Isaac Rodr�ıguez

4.1 Introduction 123

4.2 Analytical Methodology for Transformation Products Identification 124

4.2.1 GC-MS-Based Approaches 125

4.2.2 LC-MS-Based Approaches 128

4.3 Factors Influencing the Kinetics of Chlorination 131

4.4 Overview of Typical Reaction Mechanisms During Free

Chlorine Treatments 135

viii Contents

4.5 Review of Current Knowledge of Emerging Pollutant Reactions

with Free Chlorine 138


4.5.2 Androgenic and Estrogenic Steroidal Compounds 146

4.5.3 Substances of Abuse 147

4.5.4 Bisphenol A and Nonylphenol 147

4.5.5 Bactericides: Triclosan and Parabens 147

4.5.6 UV Filters 148

4.5.7 Antioxidants 148

4.5.8 Cyanotoxins 149

4.6 Other Disinfection Agents 150

4.6.1 Chlorine Dioxide 150

4.6.2 Chloramination 152

4.6.3 Permanganate and Ferrate 153

4.7 Conclusions and Outlook 155

References 155

5 Approaches to Water and Wastewater Treatment for Removal of

Emerging Contaminants: Ongoing Research and Recommendations

for Future Work 161

Sixto Malato, Pilar Fern�andez-Ib�a~nez, Isabel Oller, Lucia Prieto-Rodriguez,Sara Miralles-Cuevas and Alejandro Cabrera-Reina


5.2 Ozonation 163

5.3 Membrane Processes 165

5.4 Membrane Bioreactors (MBR) 167

5.5 AOPs Including Solar AOPs 169

5.5.1 Solar Driven Advanced Oxidation Processes 170

5.5.2 Different Approaches for Treating ECs by Solar AOPs 172

References 175

6 Transformation Products of Emerging Contaminants Formed during

Advanced Oxidation Processes 179

Ioannis K. Konstantinou, Maria Antonopoulou and Dimitra A. Lambropoulou


6.2 Pesticides 180

6.2.1 Organophosphorus Insecticides 180

6.2.2 Anilide Herbicides (ANHs) 183

6.2.3 Phenylurea Herbicides (PUHs) 187

6.2.4 Neonicotinoid Insecticides (NCIs) 198

6.2.5 Glyphosate Herbicide 203

6.3 Phthalate Esters 203

6.4 Pharmaceutical Compounds 204

6.4.1 Fibrates 205

6.4.2 b-Blockers 211

6.5 Others 215

6.5.1 Bisphenol A 215

6.5.2 Triclosan 216

Contents ix

6.6 Conclusions 217

Acknowledgments 218

References 218

7 Enzymatic Reactors Applied for the Biotransformation of Endocrine

Disrupting Chemicals 229

Juan M. Lema Rodicio, Ma Teresa Moreira, Gemma Eibes, Thelmo A. Lu-Chau,

Luc�ıa Lloret, Roberto Taboada, Adriana Arca-Ramos and Gumersindo Feijoo

7.1 Endocrine Disrupting Chemicals 229

7.1.1 Sources and Fate 230

7.1.2 Physicochemical Properties and Ecotoxicity of Endocrine

Disrupting Chemicals 231

7.1.3 Estrogenic Activity 231

7.1.4 Methods for the Removal of EDCs 234

7.2 White-Rot Fungi and Their Lignin Modifying Enzymes 234

7.2.1 Characteristics of the White-Rot Fungi 234

7.2.2 Lignin-Modifying Enzymes and Their Mediators 234

7.3 Enzymatic Reactors 238

7.3.1 Free Enzymes 238

7.3.2 Immobilized Enzymes 243

7.4 Determination of Transformation Products from the Enzymatic

Treatment of EDCs 248

7.4.1 Analytical Techniques 248

7.4.2 Transformation Products Detected in Enzymatic Treatments 249

References 255

8 Biologically Mediated Chiral Inversion of Emerging Contaminants 261

Stuart J. Khan


8.1.1 Nomenclature 261

8.1.2 Enantiomeric Fraction 262

8.1.3 Chiral Emerging Contaminants 262

8.2 Enantiospecific Analytical Methods 264

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


9.2 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

x Contents

9.4.1 Basic Principles 292

9.4.2 Quality Control in Qualitative Analysis of TPs 294

9.4.3 Applications 296

9.5 Conclusions 297

References 298

10 Transformation Products of Emerging Contaminants: Analytical Challenges

and Future Needs 303

Bozo Zonja, Jaume Ace~na, Aleksandra Jelic, Mira Petrovic,Sandra P�erez Solsona and Dami�a Barcel�o


10.2 Generation, Detection and Identification of Transformation Products

at Lab Scale: An Analytical Challenge 305

10.2.1 Detection of Transformation Products with GC-MS and LC-MS 306

10.2.2 Identification of Transformation Products 309

10.3 Quantitative Analysis of TPs in the Environment 311

10.3.1 Sample Preparation 312

10.3.2 Determination of TPs in the Environment with High

and Low Resolution Mass Spectrometric Techniques 313

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 Debora Fabbri


11.2 Potential and Differences Among the Different MS Systems

for Determining Unknown Compounds 326

11.2.1 GC-MS versus LC-MS 326

11.2.2 Capability and Potential of Instrumentation: The Right Analyzer 327

11.3 How to Proceed in the Structural Attribution 330

11.3.1 Kind of Analysis to be Performed 330

11.3.2 Strategies of Accurate Mass Screening for (non)Target

Compounds and Unknowns: Elementary Composition Assignment 333

11.3.3 Structural Attribution by MSn 333

11.3.4 Limitation 334

11.4 Accurate Mass Screening and Identification of Emerging Contaminants

in Environmental Samples: Some Cases Studied 334

11.4.1 The Spectra Library: GC-MS Approach 334

11.4.2 LC-MS2 (QqQ) Identification of Fluoxetine Transformation Products 335

11.4.3 Identification of Unknown with LTQ Orbitrap 336

11.4.4 Focus on the Same Pollutant Studied with Different Analyzers:

The Case of Diclofenac 340

11.4.5 The Use of FTICR-MS for Photodecomposition Transformation

Products of Two Pesticides 340

Contents xi

11.4.6 Combined Approach 344

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


12.2 Basic Techniques 353

12.2.1 Sample Enrichment and Clean-up 353

12.2.2 Tube NMR 354

12.2.3 Hyphenated NMRTechniques 356

12.3 Applications 359

12.3.1 EOCs and XOCs: Identification of the Transformation Products 359

12.3.2 Identification of Disinfection By-Products 367

12.3.3 Direct Analysis of XOCs and EOCs in Environmental Samples 373

12.3.4 Other Topics 376


List of Abbreviations 377

References 378

VOLUME 2

PART IV OCCURRENCE, FATE AND EFFECTS IN THE ENVIRONMENT:

AN OVERVIEW OFMAJOR CLASSES 385

13 Transformation Products of Pesticides in the Environment: Analysis and

Occurrence 387

Ana Ag€uera L�opez, Mar�ıa del Mar G�omez and Amadeo R. Fern�andez-Alba


13.2 Transformation of Pesticides in the Environment 388

13.3 Analytical Techniques Used in the Identification and Analysis of TPs 397

13.3.1 Sample Preparation and Preconcentration 397

13.3.2 Analytical Determination 403

13.4 Occurrence of Pesticide TPs in the Environment 407

13.5 Concluding Remarks 408

Acknowledgments 408

References 409

14 Metabolites and Transformation Products of Pharmaceuticals in the

Aquatic Environment as Contaminants of Emerging Concern 413

Irene Michael, Marlen Ines Vasquez, Evroula Hapeshi, Tarek Haddad,

Ewelina Baginska, Klaus K€ummerer and Despo Fatta-Kassinos


xii Contents

14.2 Human Metabolites in the Aquatic Environment 415

14.3 Biotransformation Products in the Aquatic Environment 418

14.4 Transformation of Pharmaceuticals During Photolysis and Advanced

Oxidation Processes 425

14.4.1 Photolysis 425

14.4.2 Advanced Oxidation Processes (AOPs) 439

14.5 Conclusions and Outlook 446

Acknowledgments 447

References 447

15 Transformation Products of Personal Care Products: UV Filters Case Studies 459

Kristina Pestotnik, Tina Kosjek and Ester Heath


15.2 Main Physico-Chemical Parameters of UV Filters and their Influence

on Environmental Behaviour 461

15.3 Occurrence of UV Filter Residues 465

15.3.1 UV Filters 465

15.3.2 UV Filter Transformation Products 467

15.4 Fate of UV Filter Residues 467

15.4.1 Abiotic Processes 467

15.4.2 Biotic Processes 475

15.5 Analytical Methods for Identification of Transformation Products 478

15.6 Effects and Toxicity of UV Filters and their Transformation

Products in the Environment 483

15.6.1 Ecotoxicity 483

15.6.2 Estrogenic Activity 483

15.6.3 Toxicity of Transformation Products 485

15.7 Conclusions and Future Strategies 486

Acknowledgments 487

Abbreviations 487

References 489

16 Transformation Products of Illicit Drugs 493

Dimitra A. Lambropoulou and Eleni Evgenidou


16.1.1 What are “Illicit Drugs?” 494

16.2 Fate and Treatment of IDs and Their Metabolites/TPs 495

16.2.1 Environmental Fate of IDs and Their Metabolites/TPs 495

16.2.2 Treatment Studies of IDs and Their Metabolites/TPs 497

16.3 Analytical Methods and Detection 503

16.3.1 Sampling and Storage 503

16.3.2 Analytical Methods and Detection 504

16.4 Occurrence of IDs and their Metabolites/TPs in the Environment 507

16.4.1 Wastewaters 507

16.4.2 Surface Waters 512

16.4.3 Groundwater and Drinking Water 512

16.4.4 Air 513

Contents xiii

16.5 Ecotoxicity of IDs and Their Metabolites/TPs 513

16.5.1 Sewage Epidemiology 514

16.6 Concluding Remarks 515

References 515

17 Transformation Products of Artificial Sweeteners 525

Marco Scheurer, Heinz-J€urgen Brauch and Frank Thomas Lange


17.2 Processes Leading to the Formation of Artificial Sweetener

Transformation Products 527

17.2.1 Metabolism in Mammals Including Man 527

17.2.2 Abiotic Transformation 531

17.2.3 Biodegradation 536

17.2.4 Saccharin and its Transformation Products from

Agricultural Sources 537

17.3 Summary and Conclusions 539

References 540

18 Transformation Products of Brominated Flame Retardants (BFRs) 545

Alin C. Dirtu, Alin C. Ionas, Govindan Malarvannan and Adrian Covaci


18.2 Transformation Products of PBDEs 546

18.2.1 Degradation of PBDEs in Abiotic Matrices 546

18.2.2 Biotransformation Pathways for PBDEs 553

18.3 Transformation Products of HBCDs 557

18.3.1 Degradation of HBCDs in Abiotic Matrices 557

18.3.2 Biotransformation Pathways for HBCDs 559

18.4 Transformation Products of TBBPA 561

18.4.1 Degradation of TBBPA in Abiotic Matrices 561

18.4.2 Biotransformation Pathways for TBBPA 563

18.5 Transformation Products of NBFRs 566

18.5.1 Decabromodiphenyl Ethane (DBDPE) 566

18.5.2 1,2-Bis(2,4,6-tribromophenoxy)ethane (BTBPE) 566

18.5.3 2-Ethylhexyl2,3,4,5-tetrabromobenzoate (TBB) and

Di(2-ethylhexyl)tetrabromophthalate (TBPH) 567

18.6 Concluding Remarks and Future Perspectives 568

Acknowledgments 568

References 569

19 Transformation Products of Alkylphenols 577

Montserrat Cortina-Puig, Gabino Bol�ıvar-Subirats, Carlos Barata and Silvia Lacorte

19.1 Alkylphenols: Types, Properties and Uses 577

19.2 Transformation of Alkylphenols and Identification of Transformation Products 580

19.2.1 Biodegradation 580

19.2.2 Photodegradation 587

19.2.3 Sonolysis 590

19.3 Occurrence of Alkylphenol Transformation Products in the Environment 591

xiv Contents

19.3.1 Water 591

19.3.2 Air 595

19.3.3 Soil/Sediments 596

19.3.4 Biota 597

19.4 Risks and Effects of Alkylphenols and their Transformation

Products in the Environment 598

19.4.1 Toxicological Effects 598

19.4.2 Risk Assessment 600


Acknowledgments 604

References 604

20 Biotic and Abiotic Transformation Processes of Benzotriazoles: Possible

Pathways and Products 613

Dimitra Voutsa


20.2 Biotic Degradation Processes 615

20.3 Abiotic Transformation Processes 619

20.3.1 Photochemical Transformation 619

20.3.2 Chemical Oxidation Processes 620

20.4 Future Research Needs 622

References 622

21 Identification (Quantitative Determination and Detection) and Fate

of Transformation Products of Rocket Fuel 1,1-Dimethylhydrazine 627

Bulat Kenessov and Lars Carlsen

21.1 Introduction/Background 627

21.2 Identification of Transformation Products of 1,1-Dimethylhydrazine 628

21.2.1 Laboratory Experiments 628

21.2.2 Examination of Fall Sites 630

21.2.3 Possible Mechanisms of Formation of the Main


21.3 Distribution and Fate of Transformation Products of 1,1-Dimethylhydrazine

in Soil at Fall Sites 634

21.4 Analytical Methods Applied in the Monitoring 635

21.4.1 Methods of Quantitative Determination 636

21.4.2 Systematic Approach to the Control of TPs of 1,1-Dimethylhydrazine 641

21.5 Conclusion 644

References 645

22 Assessment of the Occurrence and Fate of Transformation Products

of Endocrine Disrupting Compounds EDCs in the Environment 649

Vasiliki Boti, Vasilios Sakkas and Triantafyllos Albanis


22.2 Endocrine Disrupting Compounds (EDCs) of Concern 650

22.2.1 Definitions and Regulatory Issues 650

22.2.2 Mechanisms of Endocrine Disruption 652

Contents xv

22.3 Environmental Fate and Transformation of EDCs 652

22.4 Analytical Methodology 654

22.5 Occurrence and Endocrine Disruption Effects of the TPs of Selected EDCs 660

22.5.1 Pesticides 660

22.5.2 Industrial Chemicals 664

22.5.3 Synthetic and Natural Steroids 667

22.6 Future Needs –Recommendations 668

References 669

23 Transformation Products of Hazardous Cyanobacterial Metabolites in Water 675

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


23.2 Cyanobacterial Secondary Metabolites 676

23.2.1 Hazardous Cyanobacterial Metabolites: Cyanotoxins 676

23.2.2 Taste and Odor Compounds: Geosmin and 2-Methylisoborneol 681

23.3 Transformation Products of Cyanobacterial Metabolites in Water 682

23.3.1 Fate of Cyanobacterial Metabolites in the Environment 682

23.3.2 Chemical Oxidation 687

23.3.3 Advanced Oxidation Processes 692

23.4 Research Gaps, Recent Trends and Future Needs 698

References 699

PART V GLOBAL SPACIALITY AND ENVIRONMENTAL STATUS

OF TRANSFORMATION PRODUCTS IN THE ENVIRONMENT 709

24 Occurrence of Transformation Products of Emerging Contaminants in

Water Resources 711

Carlos GonScalves, Maria A.D. Sousa and Maria de F�atima Alpendurada24.1 Brief Introduction on the Sources of Transformation Products


24.2 Transformation Products in Natural Waters: From Contamination Sources

to Drinking Water Production 713

24.3 Wastewaters as a Major Source of Transformation Products 732

24.4 Origin and Presence of Transformation Products in Drinking Water 738

24.5 Ubiquity and Regio-Specificity of Transformation Products 740

24.6 Transformation Products of Emerging Contaminants: Fate and Behavior 741


References 746

25 Occurrence of Transformation Products of Emerging Contaminants in Water

Resources of the United States 751

Imma Ferrer and E. Michael Thurman

25.1 Introduction: Emerging Contaminants 751

25.2 State-of-the-Art Techniques for the Identification of Emerging

Contaminants and Their Transformation Products 752

xvi Contents

25.2.1 Liquid Chromatography/Tandem mass Spectrometry

(LC/MS-MS) for the Analysis of Target Compounds. EPA

Method 1694 753

25.2.2 Liquid Chromatography/Time-of-Flight/Mass Spectrometry

(LC/TOF-MS) for the Analysis of Non-target Compounds 755

25.2.3 Liquid Chromatography/Quadrupole-Time-of-Flight/Mass

Spectrometry (LC/Q-TOF-MS) for Structural Elucidation of

Unknown Compounds and Transformation Products 755

25.3 Use of Accurate Mass Tools for the Identification of Emerging

Contaminants 756

25.3.1 Molecular Features 756

25.3.2 Accurate Mass Databases 758

25.3.3 Accurate Mass Filters and Isotopic Mass Defect 762

25.3.4 Accurate Mass Profiling 765

25.4 Occurrence of Transformation Products in Environmental Waters in the US 767

References 770

26 Spatial Modeling for Elucidation of Perfluorinated Compound Sources

and Fate in a Watershed 775

Yasuyuki Zushi and Shigeki Masunaga


26.1.1 Transformation Products of PFCs 775

26.1.2 History, Regulation and Pollution of PFCs 779

26.2 Source Identification of PFCs Using GIS 780

26.2.1 Study Area and Dataset 780

26.2.2 Method of GIS-based Source Identification 782

26.2.3 Results and Discussion 783

26.3 Spatial Distribution of PFOS and PFOA Contributed by Nonpoint Sources 786

26.3.1 Method for Spatial Prediction with Fine Scale; Use of the Digital

Elevation Model (DEM) and Land-Use Regression (LUR) Model 786

26.3.2 Results and Discussion 787

26.4 Conclusion 792

Acknowledgments 793

References 793

27 Global Distribution of Polyfluoroalkyl and Perfluoroalkyl Substances

and their Transformation Products in Environmental Solids 797

Holly Lee and Scott A. Mabury


27.2 Global Contamination of PFASs in Environmental Solid Matrices 801

27.2.1 Sediments 801

27.2.2 Temporal Trends in Sediment Cores 803

27.2.3 Wastewater Treatment Plant Sludge 804

27.2.4 Soils 806

27.2.5 Case Study: Contamination of Agricultural Farmlands

in Decatur, Alabama 807

27.3 Fate of PFASs in Environmental Solids 809

Contents xvii

27.3.1 Sorption 810

27.3.2 Leaching to Surface Waters and Groundwater 812

27.3.3 Biodegradation in WWTP Media and Soils 812

27.4 Uptake into Vegetation 815

27.5 Summary and Future Outlook 817

References 818

PART VI RISK ASSESSMENT, MANAGEMENT AND REGULATORY

FRAMEWORK 827

28 Toxicity and Risk of Transformation Products of Emerging Contaminants for

Aquatic Organisms: Pharmaceutical Case Studies 829

Marina DellaGreca, Marina Isidori and Fabio Temussi


28.2 Photolysis in the Environment: Pharmaceutical Case Studies 830

28.3 Effect-Driven Approach 830

28.3.1 Amiloride 832

28.3.2 Chlorpromazine 834

28.3.3 Diclofenac 835

28.3.4 Dipyrone 836

28.3.5 Propranolol 837

28.3.6 Ranitidine and Tramadol 838

28.3.7 Spiramycin 839

28.3.8 Discussion 840

28.4 Exposure-Driven Approach 841

28.4.1 Amlodipine 841

28.4.2 Estrone 848

28.4.3 Furosemide 849

28.4.4 Naproxen 850

28.4.5 Prednisone, Prednisolone, and Dexamethasone 851

28.4.6 Ranitidine 851

28.4.7 Tamoxifen 853

28.4.8 Discussion 854

28.5 Conclusion 855

References 856

29 Quantitative Structure–Activity Relationship/QuantitativeStructure–Toxicity Relationship (QSAR/QSTR) Modeling as Tools for

Assessing Effects and Predicting Risks of Transformation Products


Lars Carlsen and Bulat Kenessov


29.2 The Toolbox 861

29.2.1 EPI Suite 862

29.2.2 PASSOnline 863

29.2.3 ADME/Tox Boxes 863

29.2.4 Partial Order Ranking 863

xviii Contents

29.3 Environmental Behavior 864

29.3.1 EPI Suite Results 864

29.4 Ecotoxicological Effect 867

29.4.1 ECOSAR Results 867

29.5 Effects on Humans 868

29.5.1 Predictions of Selected Biological Activities 868

29.5.2 Organ-Specific Adverse Health Effects 870


References 873

30 Steps Toward a Regulatory Framework for Transformation

Products in Water 877

Maria D. Hernando Guil, Maria J. Mart�ınez-Bueno, Laura Duran,Jos�e M. Navas and Amadeo R. Fern�andez-Alba


30.2 Scientific Advances and Technical Knowledge of Transformation

Products. Relevant Cases of Study 879

30.2.1 Polar Pesticides 879

30.2.2 Biocides 881


30.2.4 Industrial Chemicals 891

30.3 Toxicological Considerations in Assessing Mixtures of Chemicals

and Significance of Transformation Products in EU Regulations.

Interaction Between Regulatory Frameworks 894

References 896

31 NORMAN Association: A Network Approach to Scientific Collaboration on

Emerging Contaminants and their Transformation Products in Europe 903

Jaroslav Slobodnik and Valeria Dulio


31.1.1 Major Challenges 904

31.2 The NORMAN Network as a Science-to-Policy Interface 905

31.2.1 Prioritisation of Emerging Contaminants and their


31.2.2 Transformation Products and Mixture Toxicity 907

31.2.3 Transformation Products 907

31.2.4 Mixtures 908

31.2.5 Toxicity Profiling 909

31.3 Effect-Directed Analysis for Identification of Relevant Emerging

Contaminants and their Transformation Products in Complex

Environmental Samples 909

31.3.1 Publications 911

31.3.2 Databases 911

31.3.3 International Projects 912

31.4 Quality Control Aspects 912

31.4.1 Method Validation 912

31.4.2 Interlaboratory Studies 912

Contents xix


Acknowledgments 914

References 914

PART VII OUTLOOK 917

32 Outlook 919

Dimitra A. Lambropoulou and Leo M. L. Nollet

32.1 General Remarks 919

32.2 Gaps, Recommendations and Future Needs 921

32.2.1 Elucidation, Detection, Quantification, and Environmental

Occurrence 921

32.2.2 Environmental Fate and Transformation 922

32.2.3 Health Effects, Risk Assessment, and Prioritization 922

32.2.4 Remediation Approaches 923

Index 925

xx Contents

Preface

Over the last 15 years, the focus of chemical pollution has definitely shifted from conven-

tional “priority” pollutants, to so-called “emerging” or “new” unregulated contaminants.

Concerns during this period about the potential health and ecological impacts of exposure to

emerging contaminants (ECs) have led to the establishment of new, multi-stakeholder

research and testing initiatives, committees, expert groups, newsletters, databases, etc.,

throughout the world. Up to date, despite these actions, the term “emerging contaminants”

remains problematic and sometimes it is difficult to determine which chemicals should or

should not be classified as ECs, because they represent a changing reality, dependent on per-

spective as well as timing. In general, ECs are a structurally diverse and heterogeneous group

of chemical compounds, which have widely varying fate properties and adverse effects on

environmental ecosystems and can be classified into the following categories:

� “new” ECs, which are chemicals that are recently manufactured and suddenly appeareverywhere, and therefore, are not currently covered by existing regulations or legislation

� “old” ECs, which are the ones that were actually around for several decades, but simply werenot under regular investigation or for which analytical methods did not exist until recently.

� “ECs within complex mixtures”, such as industrial effluents, oil residues, hospital efflu-ent, etc. of which either the mixture itself or newly identified (subgroups) of components

within may be considered ECs.

In recent years, research in all branches of science and technology has been carried out on

occurrence, fate and risks of ECs in the environment. Nowadays, their occurrence has been

documented worldwide in various compartments of the water cycle including both natural

and technical aquatic systems impacted by wastewater discharges and waste disposal sites

and it has become a hot topic for environmental analytical chemists.

Despite the increasing number of published studies covering EC input, occurrence, fate

and effects, there is still a lack of understanding and knowledge about these substances in

the aquatic environment. Even more, we know almost nothing about the impacts of the envi-

ronmental exposure to trace concentrations of their transformation products (TPs) and/or

metabolites, but the detection of TPs in the environment is worrying. TPs of ECs in aquatic

environments are still rarely considered in water quality and chemical risk assessment,

although they have been found in concentrations that are of concern. Since many different

TPs can potentially be formed in the environment and analytical standards are typically lack-

ing for these compounds, knowledge on the prevalence of TPs in aquatic environments is

fragmentary.

In this view, this book intends to gather, specify, synthesize and advance existing knowl-

edge of the most important TPs of the major groups of ECs with potential concern to human

health and the environment. The topics covered range from the sources of TPs of ECs and

their environmental behaviour, to their occurrence and impacts on engineering systems and

natural environment, to risk assessment and management, to the technologies and strategies

available for control. The objective was to give as much information as possible on TPs of

the most potent ECs categories, which nowadays are the most commonly studied and moni-

tored, like for example, TPs of pharmaceuticals and personal care products (PPCPs), hor-

mones, UV filters, perfluorinated compounds, poylybrominated flame retardants (BFRs),

pesticides, plasticizers, alkyl phenols, benzotriazoles, artificial sweeteners, illicit drugs, algal

toxins, endocrine disruptor compounds (EDCs) etc.

The book is divided into 7 sections and 32 chapters, each with a distinct focus organized

into two volumes..

In volume 1, the first section with 2 chapters covers general aspects regarding the TPs. In

the first chapter the reader finds a classification of the TPs of ECs into their impact on

the environment and human health. Chapter 2 deals with the role of TPs of ECs as future

groundwater and drinking water contaminants.

The second section (chapters 3 to 8) focuses on the fate of TPs in the environment and

treatment strategies.

In volume 2 the third section with 4 chapters (chapters 9 to 12) is about analytical strate-

gies for identification and structure elucidation. Analytical challenges such as sampling and

sample preparation as well as MS and NMR techniques for structure elucidation of TPs, are

comprehensively discussed.

The fourth section (chapters 13 to 23) is dedicated to the occurrence, fate and effects of

TPs in various compartments of the environment by focusing on specific classes of ECs.

The fifth and sixth sections (each 4 chapters) cover subjects related to global spaciality

and environmental status of TPs in the environment, and risk assessment, management and

regulatory framework of TPs.

Finally, in chapter 32 (section 7), we summarize and synthesize the major findings and

conclusions, and try to predict future trends of discovery, occurrence, fate and risks of TPs

of ECs in the environment.

This book would be helpful in multifarious ways to analysts, environmental chemists, toxicol-

ogists, hydrologists, environment scientists and technologists, engineers, risk assessors, manag-

ers of industries, water treatment consultants, firms engaged in water treatment and policy

makers. In addition to professionals, anyone with a keen interest in the covered fields, as well as

teachers and students at the undergraduate and postgraduate level, would be able to use some of

the materials presented here to gain new insights and reach new perspectives in their fields.

We hope that most readers will approach this book with knowledge of one or more of the

technical areas covered, and hope that after reading this book, they will fill comfortable to

discuss and work with experts in all subject areas.

We would like to take this opportunity to express our gratitude to Ms. Rebecca Stubbs, Ms.

Emma Strickland and Ms. Sarah Tilley as well as their team at John Wiley and Sons, Ltd

Publisher, who strongly support the idea and helped make this book a reality.

Last but not least, we would like to warmly thank all authors for their excellent contribu-

tions to this book which have resulted in an outstanding and superior book.

We hope this book will help to keep the environment more green.

Science is organized knowledge. Wisdom is organized life.

Immanuel Kant

April 2013

Dimitra A. Lambropoulou and Leo M.L. Nollet

xxii Preface

List of Contributors

Jaume Ace~na, Department of Environmental Chemistry, IDAEA-CSIC, Spain

Ana Ag€uera L�opez, Department of Chemistry and Physics, University of Almer�ıa, andCIESOL (Solar Energy Research Center), Joint Centre of the University of Almer�ıa-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 Barcel�o, Water and Soil Quality Research Group, IDAEA-CSIC, and CatalanInstitute for Water Research (ICRA), Cientific and Technologic Park of Girona University,

Spain

Sara Bogialli, Department of Chemistry, University of Padua, Italy

Gabino Bol�ıvar-Subirats, Department of Environmental Chemistry, IDAEA-CSIC, Spain

Vasiliki Boti, Laboratory of Analytical Chemistry, Department of Chemistry, University of

Ioannina, Greece

Heinz-J€urgen Brauch, DVGWWater Technology Center, Germany

Alejandro Cabrera-Reina, Department of Chemical Engineering, University of Almer�ıa,and CIESOL, Joint Centre of the University of Almer�ıa-CIEMAT, Spain

Paola Calza, Dipartimento di Chimica, Universit�a di Torino, Italy

Lars Carlsen, Awareness Center, Denmark

Serge Chiron, UMR HydroSciences 5569, France

Monia Cieszy�nska, Department of Environmental Toxicology, Faculty of Health Sciences,Medical University of Gdansk, Poland

Montserrat Cortina-Puig, Escola Universit�aria Salesiana de Sarri�a, 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 F�atima Alpendurada, IAREN – Water Institute of the Northern Region, andFaculty 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

Mar�ıa del Mar G�omez Ramos, European Union Reference Laboratory (EURL), Depart-ment of Chemistry and Physics, University of Almer�ıa, 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 Cient�ıfico Tecnol�ogico, University of Alcal�a, 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, Universit�a 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. Fern�andez-Alba, Department of Chemistry and Physics, University of Almer�ıa,and CIESOL (Solar Energy Research Center), Joint Centre of the University of Almer�ıa-CIEMAT, and European Union Reference Laboratory (EURL), Department of Chemistry

and Physics, University of Almer�ıa, Spain

Pilar Fern�andez-Ib�a~nez, Plataforma Solar de Almer�ıa (CIEMAT), and CIESOL, JointCentre of the University of Almer�ıa-CIEMAT, Spain

Imma Ferrer, Center for Environmental Mass Spectrometry, University of Colorado, USA

xxiv List of Contributors

Theodora Fotiou, Institute of Advanced Materials, Physicochemical Processes, Nano-

technology and Microsystems, National Center for Scientific Research “Demokritos”,

Greece

Gra _zyna Gałęziowska, Department of Environmental Toxicology, Faculty of HealthSciences, Medical University of Gdansk, Poland

Markus Godejohann, Bruker BioSpin, Germany

Carlos GonScalves, 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,


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 Researchand Technology, INIA, Spain

Anastasia Hiskia, Institute of Advanced Materials, Physicochemical Processes, Nano-

technology 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 Universit�a 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 K€ummerer, Institute of Environmental Chemistry, Faculty for Sustainability,Leuphana University, Germany

Silvia Lacorte, Department of Environmental Chemistry, IDAEA-CSIC, Spain

List of Contributors xxv

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

Lucı́a 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 Almer�ıa (CIEMAT), and CIESOL, Joint Centre of theUniversity of Almer�ıa-CIEMAT, Spain

Maria J. Mart�ınez-Bueno, Department of Hydrogeology and Analytical Chemistry,University of Almer�ıa, Spain

Shigeki Masunaga, Graduate School of Environment and Information Sciences, Yokohama

National University, Japan

Irene Michael, Department of Civil and Environmental Engineering, and NIREAS, Interna-

tional Water Research Centre, University of Cyprus, Cyprus

Sara Miralles-Cuevas, Plataforma Solar de Almer�ıa (CIEMAT), and CIESOL, Joint Centreof the University of Almer�ıa-CIEMAT, Spain

Mª Teresa Moreira, Department of Chemical Engineering, University of Santiago de

Compostela, Spain

Jacek Namie�snik, Department of Analytical Chemistry, Faculty of Chemistry, GdanskUniversity of Technology, Poland

Jos�e M. Navas, Department of Hydrogeology and Analytical Chemistry, University ofAlmer�ıa, Spain

Leo M.L. Nollet, University College Ghent, Belgium

Isabel Oller, Plataforma Solar de Almer�ıa (CIEMAT), and CIESOL, Joint Centre of theUniversity of Almer�ıa-CIEMAT, Spain

Kevin O’Shea, Department of Chemistry and Biochemistry, Florida International

University, USA

Sandra P�erez Solsona, Department of Environmental Chemistry, IDAEA-CSIC, Spain

Kristina Pestotnik, “Jožef Stefan” Institute, Department of Environmental Sciences,

Ecological Engineering Institute Ltd, and “Jožef Stefan” International Postgraduate School,

Slovenia

xxvi List of Contributors

Mira Petrovic, Catalan Institute for Water Research (ICRA), Cientific and Technologic

Park of Girona University, and Instituci�o Catalana de Recerca i EstudisAvanScats(ICREA), Spain

Alfred Preiss, Fraunhofer Institute for Toxicology and Experimental Medicine, Germany

Lucia Prieto-Rodriguez, Plataforma Solar de Almer�ıa (CIEMAT), and CIESOL, JointCentre of the University of Almer�ıa-CIEMAT, Spain

Stefano Polesello,Water Research Institute, IRSA-CNR, Italy

Jos�e Benito Quintana, Department of Analytical Chemistry, Nutrition and FoodSciences, IIAA – Institute for Food Analysis and Research, University of Santiago de

Compostela, Spain

Rosario Rodil, Department of Analytical Chemistry, Nutrition and Food Sciences, IIAA

– Institute for Food Analysis and Research, University of Santiago de Compostela, Spain

Isaac Rodr�ıguez, Department of Analytical Chemistry, Nutrition and Food Sciences,IIAA – Institute for Food Analysis and Research, University of Santiago de Compostela,

Spain

Vasilios Sakkas, Laboratory of Analytical Chemistry, Department of Chemistry, University

of Ioannina, Greece

Marco Scheurer, DVGWWater Technology Center, Germany

Jaroslav Slobodnik, Environmental Institute, Slovak Republic

Weihua Song, Department of Environmental Science & Engineering, Fudan University, PR

China

Marianne E. Stuart, British Geological Survey, UK

Roberto Taboada, Department of Chemical Engineering, University of Santiago de

Compostela, Spain

Fabio Temussi, Department of Chemical Sciences, University Federico II, Italy

Frank Thomas Lange, DVGWWater Technology Center, Germany

E. Michael Thurman, Center for Environmental Mass Spectrometry, University of

Colorado, USA

Theodoros M. Triantis, Institute of Advanced Materials, Physicochemical Processes, Nano-

technology and Microsystems, National Center for Scientific Research “Demokritos”, Greece

Sara Valsecchi,Water Research Institute, IRSA-CNR, Italy

Marlen Ines Vasquez, Department of Civil and Environmental Engineering, and NIREAS,


Davide Vione, Dipartimento di Chimica Analitica, Universit�a degli Studi di Torino, Italy

Dimitra Voutsa, Environmental Pollution Control Laboratory, Department of Chemistry,

Aristotle University of Thessaloniki, Greece

List of Contributors xxvii

Lidia Wolska, Department of Analytical Chemistry, Faculty of Chemistry, Gdansk University

of Technology, and Department of Environmental Toxicology, Faculty of Health

Sciences, Medical University of Gdansk, Poland

Bozo Zonja, Department of Environmental Chemistry, IDAEA-CSIC, Spain

Yasuyuki Zushi, Center for Environmental Measurement, Organochemical Measurement

Laboratory, National Institute for Environmental Studies, Japan

xxviii List of Contributors

201 x 261mm · 2014. 2. 10. · leo m. l. nollet emeritus, faculty of applied engineering sciences,...

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