Table of Contents

Title Page

Epigraph

Abbreviations

Glossary

Preface

Acknowledgment

Chapter 1: Introduction

1.1 Chemistry and Development
1.2 Pollution and Contamination
1.3 Chemical Pollutants
1.4 Pollutants in the Environment
1.5 Concept of Emerging Pollutants
1.6 Historical Background of Emerging Pollutants
1.7 Classification of Emerging Pollutants
1.8 Regulations and Normatives
References

Chapter 2: Occurrence and Removal of Environmental Pollutants

2.1 Introduction
2.2 Pollutants in the Atmosphere
2.3 Pollutants in Ground and Surface Waters: Quality Parameters
2.4 Pollutants in the Ground and Soil
2.5 Sources of Emerging Pollutants or CECs
2.6 Treatment of CECs
2.7 Toxicity of CECs
References

Chapter 3: Detection and Analysis of Chemical Pollutants

3.1 Introduction
3.2 Sample Preparation
3.3 Analytical Methods for Identifying EPs
References

Chapter 4: Overview of Pharmaceutical Products as Emerging Pollutants

4.1 Introduction
4.2 Therapeutic Classes of PCs Detected in the Environment
4.3 Sources of PCs in the Environment
4.4 Detection and Analysis of PCs in the Environment
4.5 Occurrence of PCs in the Environment
4.6 Ecotoxicological Aspects of PCs on Environment
4.7 Removal of PCs
4.8 Conclusions
References

Chapter 5: Therapeutic Classes of PCs in the Environment

5.1 Introduction
5.2 Antibiotics (ABs)
5.3 Estrogens and Hormonal Compounds
5.7 Antiepileptic Drugs
5.8 $c05-math-125$ -Blockers/Diuretics
5.9 Lipid Regulators
5.10 $c05-math-157$ -Sympathomimetic Drugs
5.11 Antidiabetic Drugs
5.12 X-Ray Contrast Drugs: Diagnostic Agents
5.13 Cytostatic PCs: Antineoplastics
5.14 Veterinary Drugs: Anthelmintics
References

Chapter 6: Illegal Drugs, Occurrence, and Fate in Environment

6.1 Introduction
6.2 What is an Illicit Drug?
6.3 Classes of Illicit Drugs
6.4 Analytical Methods for Detecting of Illicit Drugs
6.5 Illicit Drugs in the Environmental Compartments
6.6 Estimation of Drug Consumption in Communities (Sewage-Based Epidemiology)
References

Chapter 7: Pesticides as Pollutants

7.1 Introduction
7.2 Classification of Pesticides
7.3 Organic Pesticides
7.4 Pesticides in the Environment
7.5 An Example of National Survey: Pesticides in Italy
7.6 An Example of Pesticides in the Environment: Neonicotinoid Insecticides
References

Chapter 8: Lifestyle Products as Emerging Pollutants

8.1 Introduction
8.2 Stimulants
8.3 Food Additives
8.4 Classes of Food Additives
8.5 Food Additives as Emerging Organic Contaminants
8.6 Antioxidants in the Environment
8.7 Artificial Sweeteners in the Environment
References

Chapter 9: Industrial Chemicals as Emerging Pollutant

9.1 Introduction
9.2 Perfluorinated Alkyl Substances (PFASs)
9.3 Plasticizers
9.4 Flame Retardants
9.5 Brominated Flame Retardants (BFRs)
9.6 Polychlorinated Alkanes (C₁₀−C₁₃)
9.7 Organophosphate Flame Retardants (OPFRs)
9.8 Corrosion Inhibitors: Benzothiazoles and Benzotriazoles
9.9 Polycyclic Aromatic Hydrocarbons (PAHs)
9.10 Volatile Organic Compounds (VOCs)
9.11 Other Industrial Chemicals
References

Chapter 10: Surfactants in the Environment

10.1 Introduction
10.2 Structure and Classification
10.3 Nonionic Surfactants
10.4 Anionic Surfactants
10.5 Cationic Surfactants
10.6 Amphoteric Surfactants
10.7 Alkoxylated Polysiloxanes
10.8 Fluorosurfactants
10.9 Toxicological Aspects (Environmental Impact) of Surfactants
10.10 Environmental Occurrence of the Surfactants
10.11 Biodegradation of Surfactants
References

Chapter 11: Personal-Care Products

11.1 Introduction
11.2 Musks: Fragrances
11.3 Biocides
11.4 Sunscreen Agents: UV Filters
11.5 Insect Repellents: N,N-diethyl-m-toluamide (DEET)
11.6 Other PCPs
References

Chapter 12: Water Disinfectant By-Products

12.1 Introduction
12.2 Wastewater Treatments
12.3 Disinfection Methods
12.4 Water DPBs
12.5 Methods of Analysis of DBPs
12.6 Disinfection By-Products (DBPs) in Drinking Water
12.7 Disinfection By-Products in Swimming Pools
12.8 Changes in Oxidation/Disinfection Strategies
12.9 Toxicological Studies on DBPs
12.10 Regulations/Guidelines of DBPs in Drinking Water
References

Chapter 13: Other Contaminants of Emerging Concern

13.1 Introduction
13.2 Nanotechnology as a Pollution Source
13.3 Microplastics (MPs)
13.4 Toxic Elements and Elemental Species
13.6 Microorganisms
13.7 Contaminants on the Horizon: Ionic Liquids and Prions
References

InChI Key for the Most Relevant Compounds in this Book

Index

End User License Agreement

List of Illustrations

Chapter 1: Introduction

Figure 1.1 POP global migration processes. (Data taken from Ref. [6].)
Figure 1.2 Timeline of EPA regulations and lists of contaminants.

Chapter 2: Occurrence and Removal of Environmental Pollutants

Figure 2.1 Main routes and sources of CECs.
Figure 2.2 Main migration processes to soil.
Figure 2.3 Scheme with different types of filtrations, displaying the sizes of well-known items.
Figure 2.4 Scheme of a generic urban water cycle. Dotted lines indicate untreated water release
Figure 2.5 Scheme of the impact of CECs on the environment and in humans.

Chapter 3: Detection and Analysis of Chemical Pollutants

Figure 3.1 Schematic representation of the DLLME method [8].
Figure 3.2 Application of VALLME percentage (%) in different sample sources.
Figure 3.3 Single-drop microextraction (SDME) procedures. (a) Direct immersion (DI) and (b) headspace (HS).
Figure 3.4 Schematic representation of the MSPD method [15].
Figure 3.5 Analytical methods for biological and environmental samples [20].

Chapter 4: Overview of Pharmaceutical Products as Emerging Pollutants

Figure 4.1 Global PCs sales during the 2013–2015 period by region.⁶
Figure 4.2 Principal contamination routes of PCs.
Figure 4.3 Chemical structure of some acidic drugs.
Figure 4.4 Relative percentage of therapeutic classes detected in the environment [208].

Chapter 5: Therapeutic Classes of PCs in the Environment

Figure 5.1 Timeline of the discovery of ABs.
Figure 5.2 Abundance of ABs.
Figure 5.3 Chemical structure of aminoglycosides gentamicin and streptomycin.
Figure 5.4 Chemical structure of common ansamycins.
Figure 5.5 Chemical structure of tetracyclines.
Figure 5.6 Chemical structure of penicillins ( $c05-math-008$ -lactams).
Figure 5.7 Chemical structure of cesphalosporins.
Figure 5.8 Chemical structure of chloramphenicol.
Figure 5.9 Chemical structure of cyclic peptides polymyxin B1 and B2.
Figure 5.10 Chemical structure of glycopeptide vancomycin.
Figure 5.11 Chemical structure of imidazoles.
Figure 5.12 Chemical structure of lincosamide lincomycin.
Figure 5.13 Chemical structure of lipopeptide daptomycin.
Figure 5.14 Chemical structure of erythromycin (macrolides).
Figure 5.15 Chemical structure of mitomycin C.
Figure 5.16 Chemical structure of nitrofurans.
Figure 5.17 Chemical structure of oxazolidinones linezolid and tedizolid.
Figure 5.18 Chemical structure of polyene amphotericin B.
Figure 5.19 Chemical structure of polyether calcimycin.
Figure 5.20 Chemical structure of polypeptide bacitracin.
Figure 5.21 Chemical structure of quinolone ciprofloxacin.
Figure 5.22 Chemical structure of quinoxaline carbadox.
Figure 5.23 Chemical structure of streptogramin pristinamycin IA.
Figure 5.24 Chemical structure of sulfanilamide.
Figure 5.25 Chemical structure of trimethoprim.
Figure 5.26 Chemical structure of Sulfadiazine.
Figure 5.27 Chemical structure of some steroids and hormones.
Figure 5.28 Scheme of the potential endocrine disrupting PCs [114].
Figure 5.29 Chemical structure of paracetamol and acetylsalicylic acid.
Figure 5.30 Chemical structure of most common NSAIDs.
Figure 5.31 Structure of some benzodiazepine drugs.
Figure 5.32 Structure of selected psychotropic drugs.
Figure 5.33 Structure of selected psychotropic drugs.
Figure 5.34 Structure of carbamazepine.
Figure 5.35 Structure of some $c05-math-131$ -blockers.
Figure 5.36 Main structure of statins.
Figure 5.37 Chemical structure of some sympathomimetic $c05-math-158$ agonist drugs.
Figure 5.38 Chemical structure of metformin.
Figure 5.39 Structure of triiodobenzoic derivatives used as X-ray contrast drugs.
Figure 5.40 Chemical structure of some antineoplastic drugs.
Figure 5.41 Chemical structure of some commercially available anthelmintic benzimidazoles (I).
Figure 5.42 Chemical structure of some commercially available anthelmintics diphenylsulfides (II) and imidazothiazole (III) groups.
Figure 5.43 Chemical structure of some commercially available anthelmintics hexahydropyrazine (IV).
Figure 5.44 Chemical structure of some commercially available anthelmintics macrocyclic lactone (V) group.
Figure 5.45 Chemical structure of anthelmintics salicylanilide (VI) and tetrahydropyrimidine (VII) groups).
Figure 5.46 Chemical structure of niclofolan (NIF).

Chapter 6: Illegal Drugs, Occurrence, and Fate in Environment

Figure 6.1 Chemical structure of main opiate-type substances.
Figure 6.2 Chemical structure of main opiate metabolites.
Figure 6.3 Structure of the parent compound cocaine and its metabolites.
Figure 6.4 Chemical structure of main amphetamine-type substances (ATS).
Figure 6.5 Chemical structure of some precursors and by-products in illicit drug manufacture.
Figure 6.6 Chemical structure of main hallucinogen substances.
Figure 6.7 Chemical structure of main cannabinoids substances.
Figure 6.8 Chemical structure of main illicit substances.

Chapter 7: Pesticides as Pollutants

Figure 7.1 Chemical structure of the “dirty dozen” POPs.
Figure 7.2 General structure of several families of organophosphorus pesticides.
Figure 7.3 Structure of the most common organophosphorus pesticides.
Figure 7.4 Chemical structure of carbamate and common carbamate pesticides.
Figure 7.5 Chemical structure of the two classes of thiocarbamates.
Figure 7.6 Chemical structure of some commercial thiocarbamates.
Figure 7.7 Chemical structure of some dithiocarbamate fungicides.
Figure 7.8 Chemical structure of natural pyrethrins.
Figure 7.9 Chemical structure of 1 $c07-math-011$ and 2 $c07-math-012$ generation of synthetic pyrethroids.
Figure 7.10 Chemical structure of some phenoxide herbicides.
Figure 7.11 Chemical structure of triazine group of pesticides.
Figure 7.12 Chemical structure of main uracil and urea herbicides.
Figure 7.13 Chemical structure of main imidazole pesticides.
Figure 7.14 Chemical structure of main benzimidazoles.
Figure 7.15 Chemical structure of main triazoles fungicides.
Figure 7.16 Chemical structure of main morpholine fungicides.
Figure 7.17 Chemical structure of paraquat and diquat dibromide.
Figure 7.18 Chemical structure of amide fungicides.
Figure 7.19 Chemical structure of neonicotinoid insecticides.
Figure 7.20 Chemical structure of pyridazine herbicides.
Figure 7.21 Chemical structure of pyridazinone herbicides.
Figure 7.22 Chemical structure of nitrile herbicides.
Figure 7.23 Chemical structure of dinitroaniline herbicides.
Figure 7.24 Chemical structure of pyridine herbicides.
Figure 7.25 Chemical structure of pyrimidine herbicides.
Figure 7.26 Examples of pesticide degradation reactions in different compartments.

Chapter 8: Lifestyle Products as Emerging Pollutants

Figure 8.1 Structure of some central nervous system stimulants.
Figure 8.2 Structure of the main artificial sweeteners.

Chapter 9: Industrial Chemicals as Emerging Pollutant

Figure 9.1 Structure of nonylphenol and bisphenol A and F.
Figure 9.2 Structure of most common phthalates.
Figure 9.3 General biodegradation pathway for phthalate esters in the environment. Data taken from Ref. [90]
Figure 9.4 Chemical structure of N-alkylmethylbenzenesulfonamides
Figure 9.5 Total volume of flame-retardant world production.⁷
Figure 9.6 Structure of some polybrominated compounds.
Figure 9.7 Relative amounts of FRs used in different sectors. Data taken from Ref. [128]
Figure 9.8 Structure of the most common TBBPA derivatives.
Figure 9.9 Structure of the most common organophosphate flame retardants (OPFRs).
Figure 9.10 Chemical structure of benzotriazole (BT) and derivatives.
Figure 9.11 Chemical structure of benzothiazole and derivatives.
Figure 9.12 The 16 priority pollutant PAHslisted by USEPA.
Figure 9.13 Structure of the most common siloxanes (cyclic and linear).

Chapter 10: Surfactants in the Environment

Figure 10.1 Most commonly observed geometrical shapes of surfactant micelles in aqueous solution.
Figure 10.2 Structure of the tail in surfactants.
Figure 10.3 Scheme of the head type in surfactants.
Figure 10.4 Surfactant sales in the EU in 2014.²
Figure 10.5 General formula of fatty alcohol polyglycol ethers.
Figure 10.6 Chemical structure of an AEO nonionic surfactant.
Figure 10.7 Structure of EO/PO block polymers.
Figure 10.8 Structure of two major alkylphenol polyglycol ethers.
Figure 10.9 Structure of 4-NP and its derivatives.
Figure 10.10 Structure of alkanolamides.
Figure 10.11 Structure of ethoxylated fatty acids.
Figure 10.12 Chemical structure of glycol and glycerol esters.
Figure 10.13 Structure of alkyl polyglucosides.
Figure 10.14 Structure of sorbitans and their ester-based emulsifiers.
Figure 10.15 Chemical structure of sucrose esters.
Figure 10.16 Chemical structure of glycol and glycerol esters.
Figure 10.17 Chemical structure of ethoxylated sorbitan fatty acid esters.
Figure 10.18 Chemical structure of ethoxylated pentaerythritol ester.
Figure 10.19 Chemical structure of polyglycerol monooleate.
Figure 10.20 Chemical structure of alkyl dimethylamine oxide.
Figure 10.21 Structure of carboxylic acid derivatives salts.
Figure 10.22 Chemical structure of an ether carboxilate salt.
Figure 10.23 Chemical structure of sodium lauryl sulfate (SLS).
Figure 10.24 Chemical structure of alcohol ethoxy sulfates (AEOSs) anionic surfactants.
Figure 10.25 Chemical structure of alkyl sulfonates.
Figure 10.26 Chemical structure of sodium alkylbenzene sulfonates (LAS).
Figure 10.27 Chemical structure of sulfosuccinates.
Figure 10.28 Chemical structure of sulfo fatty acid esters.
Figure 10.29 Chemical structure of acylamino alkane sulfonates.
Figure 10.30 Chemical structure of alkyl phosphates and alkyl ether phosphates.
Figure 10.31 Chemical structure of sodium acylglutamates.
Figure 10.32 Chemical structure of sodium acyl polypeptide.
Figure 10.33 Chemical structure of salts of acylamino acids.
Figure 10.34 Structure of cationic surfactants (alkyl amine salts).
Figure 10.35 Structure of tetraalkyl(-aryl) amonium salt.
Figure 10.36 Structure of heterocyclic amonium salts.
Figure 10.37 Structure of different ethoxylated alkyl amines.
Figure 10.38 Structure of esterified quaternaries.
Figure 10.39 Structure of different acyl ethylenediamines.
Figure 10.40 Structure of different N-alkyl amino acids.
Figure 10.41 Structure of different alkyl betaines.
Figure 10.42 Structure of different polydimethyl siloxane. A denotes a hydrophilic group such as polyoxyethylene, amines, etc.
Figure 10.43 Examples of the structure of some fluorosurfactants.

Chapter 11: Personal-Care Products

Figure 11.1 Main chemical structure of different types of musks.
Figure 11.2 Timeline of the discovery of musks.
Figure 11.3 Structure of triclosan and triclocarban.
Figure 11.4 Structure of chrorophene and dichlorophene.
Figure 11.5 Chemical structure of seven alkyl esters of p-hydroxybenzoic acid (parabens), with the ester O − C bond in bold.
Figure 11.6 Chemical structure of benzophenone-3 and derivatives.
Figure 11.7 Structure of main benzylidene camphor derivatives.
Figure 11.8 Structure of main UV filters.
Figure 11.9 Metabolic pathways of benzophenone-3 in rats.
Figure 11.10 Metabolic pathway of 4-MBC in vivo.
Figure 11.11 Structure of N,N-diethyl-m-toluamide (DEET).

Chapter 12: Water Disinfectant By-Products

Figure 12.1 Chemical structure of sodium dichloroisocyanurate.
Figure 12.2 Relative amounts of ozone and chlorinated DBPs in drinking water.
Figure 12.3 Structure of mutagen-X (MX) and analogs.
Figure 12.4 MX ring opening equilibrium reaction (pH driven).
Figure 12.5 Examples of DNPH and DMNTH derivatization reactions for carbonyl compounds to yield hydrazone products.

Chapter 13: Other Contaminants of Emerging Concern

Figure 13.1 Scheme of the structure of a single-walled carbon nanotube (SWCNT).
Figure 13.2 Environmental risk of MPs in freshwater.
Figure 13.3 Human sources of atmospheric Hg production. Data taken from Ref. [80]
Figure 13.4 Structure of some mycotoxins, including ergot alkaloids.
Figure 13.5 Structure of some phytoplankton toxins.
Figure 13.6 Structure of some toxins in vegetable foodstuffs.

List of Tables

Chapter 1: Introduction

Table 1.1 Example of emissions of natural and human origin.^a
Table 1.2 Representative list of EPs
Table 1.3 Toxicological guideline values established by EFSA and JECFA.^a,b

Chapter 2: Occurrence and Removal of Environmental Pollutants

Table 2.1 Conductivity of some water types and watery solutions.^a
Table 2.2 Brief characterization of the water-goodness classes.^a
Table 2.3 Organic wastewater compounds detected in 20 public supply wells on Cape Cod, Massachusetts.^a,b

Chapter 3: Detection and Analysis of Chemical Pollutants

Table 3.1 SPME fibre coatings classification and preparation procedures [12]

Chapter 4: Overview of Pharmaceutical Products as Emerging Pollutants

Table 4.1 Detected PCs concentration (ng L $c04-math-034$ ) in the waters of the Ter river (N Spain) in three sampling campaigns.^{a ,b}
Table 4.2 Concentration (ng L $c04-math-046$ ) of some PCs in different water types and regions
Table 4.3 Concentration of selected drugs and TPs in groundwater
Table 4.4 The 13 PCs detected in seawater in southwestern Taiwan.^a
Table 4.5 Global comparison of CEC concentrations (ng L $c04-math-065$ ) in seawater.^a
Table 4.6 Concentration of selected PCs found in soil in different countries.^a
Table 4.7 Toxic and ecological effects of PCs on organisms.^a
Table 4.8 Concentration (ng L $c04-math-094$ ) of PCs in the influent and effluent of WWTP and in the inlet and outlet of the UV treatment.^a

Chapter 5: Therapeutic Classes of PCs in the Environment

Table 5.1 Classes and codes of anatomic therapeutic
Table 5.2 Range and typical concentrations (ng L $c05-math-001$ ) detected for main PC classes.^a,b
Table 5.3 Evolution of resistance to antibiotics.^a
Table 5.4 Maximum concentrations (ng L $c05-math-034$ ) of hormones in different types of water in various locations.^a
Table 5.5 Reported detection limit of different analytical methods for various EDCs in water samples.^a
Table 5.6 Concentrations of anti-inflammatory drugs and metabolites in STP effluents as well as rivers and streams.^a
Table 5.7 Minima and maxima concentrations of $c05-math-146$ -blockers measured in influent and effluent of WWTPs.^a
Table 5.8 Concentrations of lipid regulators and metabolites in STP effluents as well as rivers and streams.^a
Table 5.9 Concentrations of $c05-math-160$ -blockers, $c05-math-161$ -sympathomimetics, and other drugs in STP effluents as well as in rivers and streams.^a
Table 5.10 Physicochemical properties of selected anthelmintics.^a

Chapter 6: Illegal Drugs, Occurrence, and Fate in Environment

Table 6.1 Levels of illicit drugs (ng L $c06-math-023$ ) in untreated wastewater influents of several European countries.^a
Table 6.2 Levels of illicit drugs (ng L $c06-math-032$ ) in treated wastewater effluents of several European countries.^a
Table 6.3 Levels of illicit drugs (ng L $c06-math-047$ ) in surface water of several European countries.^a
Table 6.4 Concentration (ng L $c06-math-052$ ) of selected emerging organic contaminants in southwestern Taiwan.^{a , b}

Chapter 7: Pesticides as Pollutants

Table 7.1 Classification of pesticides according to their use.^a
Table 7.2 Pesticides classified according to target pests and action.^a
Table 7.3 WHO classification of pesticides by hazard
Table 7.4 List of the “dirty dozen” POP compounds and use/source
Table 7.5 Physicochemical properties of neonicotinoid insecticides.^a
Table 7.6 Concentration of pesticides in drinking water regulated by EPA.^a
Table 7.7 Concentration (ng L $c07-math-025$ ) of selected pesticide TPs found in groundwater.^a
Table 7.8 Itailian rivers, lakes, and regional groundwaters (GW) where pesticides have been investigated.^a
Table 7.9 Maximum concentration of most detected pesticides in both surface water and groundwater.^a

Chapter 8: Lifestyle Products as Emerging Pollutants

Table 8.1 Locations and concentrations of caffeine in seawater.^a
Table 8.2 AccepTable daily intake (ADI) values of some food additives.^a
Table 8.3 Concentration levels of preservatives in foods.^a
Table 8.4 Reported concentrations of selected artificial sweeteners in the environment

Chapter 9: Industrial Chemicals as Emerging Pollutant

Table 9.1 Relevant industrial chemicals
Table 9.2 Standard and guideline values ( $c09-math-006$ g L $c09-math-007$ ) established for industrial chemicals for groundwater.^a
Table 9.3 Use of phthalates (according to risk assessment of NTP CERHR, modified).^a
Table 9.4 Physicochemical properties for the most common phthalate esters.^a
Table Figure 9.6 Use of penta- (PeBDE), octa- (OBDE), and deca-bromodiphenyl ethers (DeBDE) in resins, polymers, and substrates.^a
Table 9.5 Nomenclature for PBDEs, chemical formula, and number of isomer congeners
Table 9.7 Composition of commercial PBDEs.^a
Table 9.8 Physicochemical properties of some PBDEs.^a
Table 9.9 Standard, guideline, and concentration values ( $c09-math-329$ g L $c09-math-330$ ) found in groundwater for industrial chemicals

Chapter 10: Surfactants in the Environment

Table 10.1 Some examples of major commercial and industrial surfactants.^a
Table 10.2 Screening tests (anerobic biodegradability) of anionic surfactants

Chapter 11: Personal-Care Products

Table 11.1 Concentration ranges (ng $c011-math-024$ ) of parabens detected in surface water
Table 11.2 DEET concentration in different water types in countries

Chapter 12: Water Disinfectant By-Products

Table 12.1 Examples of halogenated DBPs reported for chlorination
Table 12.2 Examples of DBPs reported for Cl₂ and O₃
Table 12.3 Examples of non-halogenated DBPs
Table 12.4 Reported chloroform levels in different media
Table 12.5 TCAA concentration in different media (water sources)
Table 12.6 Total THM regulatory limits in different countries and regions.^a

Chapter 13: Other Contaminants of Emerging Concern

Table 13.1 Toxic elements emissions from different industrial sectors.^a
Table 13.2 Physical and biological half-lives of several radionuclides.^a
Table 13.3 Mold fungi that form mycotoxins, and their main substrates.^a
Table 13.4 Content ( $c013-math-160$ g kg $c013-math-161$ ) of aflatoxin B $c013-math-162$ in some foods with mold.^a
Table 13.5 Key phytoplankton toxins and their occurrence

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Abbreviations

α-E2	17α-estradiol
2,3,7,8-TCDD	2,3,7,8-tetrachlorodibenzo-p-dioxin
4-NP	4-nonylphenol
4-OP	4-t-octylphenol
610P	di-(n-hexyl, n-octyl, n-decyl) phthalate
AB	antibiotic
ABS	acrylonitrile butadiene styrene
ACR	acute to chronic ratio
ADI	acceptable daily intake
AEO	alcohol ethoxylate
AOP	advanced oxidation process
APEO	alkylphenol ethoxylate
API	active pharmaceutical ingredient
ATS	amphetamine-type substance
AV	acute (toxicity) value
AWQC	ambient water quality criteria
BBP	butyl benzyl phthalate
BDE	brominated diphenylether
BFR	brominated flame retardant
BHA	butylated hydroxyanisole
BHT	butylated hydroxytoluene
BOD	biochemical oxygen demand
BOP	butyl 2-ethylhexyl phthalate
BPA	bisphenol A
BPF	bisphenol F
BSTFA	N,O-bis-(trimethylsilyl)-trifluoroacetamide
BTBPE	1,2-bis(2,4,6-tribromophenoxy)ethane
BW	body weight
CBZ	carbamezapene
CCC	criterion continuous concentration
CDC	center of disease control and prevention
CEC	contaminants of emerging concern
CI	chemical ionization
CMC	criterion maximum concentration
CNT	carbon nanotube
COD	chemical oxygen demand
CV	chronic (toxicity) value
CWA	Clean Water Act
D711P	di-(heptyl, nonyl, undecyl) phthalate
DAP	diallyl phthalate
DBDPE	decabromodiphenyl ethane
DBP	disinfection by-product
DDT	1,1,1-trichloro-2,2-bis(p-chlorophenyl)ethane
DEET	N,N-dimethyl-m-toluamide
DEHP	di-2-ethylhexyl phthalate
DEP	diethyl phthalate
DES	diethylstilbestrol
DHP	di-iso-hexyl phthalate
DIBP	di-iso-butyl phthalate
DIDP	di-iso-decyl phthalate
DINP	di-iso-nonyl phthalate
DIOP	di-iso-octyl phthalate
DLLME	dispersive liquid-liquid microextraction
DMP	dimethyl phthalate
DnBP	di-n-butyl phthalate
DnHP	di-n-hexyl phthalate
DnOP	di-n-octyl phthalate
DOC	dissolved organic carbon
DPP	di-n-propyl phthalate
DTDP	ditridecyl phthalate
DUP	diundecyl phthalate
DWEL	drinking-water equivalent level
DWT	drinking-water treatment
DWTP	drinking-water treatment plant
E1	estrone
E2	17β-estradiol
E3	estriol
ECHA	European Chemicals Agency
EDA	effect-directed analysis
EDC	endocrine disrupting chemical
EDDP	2-ethylidene-1,5-dimethyl-3,3-diphenylpyrrolidine
EDSS	environmental decision support system
EDTA	ethylenediaminetetraacetic acid
EE2	17α-ethynylestradiol
EFSA	European Food Safety Authority
ELISA	enzyme linked immuno sorbent assay
ELS	early life-stage (toxicity test)
ENM	engineered nanomaterial
EP	emerging pollutant
EPA	Environmental Protection Agency
ESI	electrospray ionization
EU	European Union
FACR	final acute to chronic ratio
FAO	food and agriculture organization of the United Nations
FAV	final acute value
FDA	food and drugs administration
GAC	granular activated carbon
GC-MS/MS	tandem gas chromatography-mass spectrometry/mass spectrometry
GC/MS	gas chromatography/mass spectrometry
GC	gas chromatography
GMAV	genus mean acute value
GMCV	genus mean chronic value
HAA	haloacetic acid
HAN	haloacetonitrile
HBB	hexabromobenzene
HBCDD	hexabromocyclododecane
HBRC	hawke's bay regional council
HHCB	galaxolide
HLB	hydrophilic-lipophilic balance
HPG	hypothalamic-pituitary-gonadal (axis)
HPLC	high-performance liquid chromatography
HPT	hypothalamic-pituitary-thyroid (axis)
HRMS	high-resolution mass spectrometry
HTLC	high-temperature liquid chromatography
ID	illicit drug
iodo-THMs	iodo-trihalomethane
IR	infrared
IUPAC	International Union of Pure and Applied Chemistry
JECFA	joint FAO/WHO expert committee on food additives
LAS	linear alkylbenzene sulfonate
LAU	large animal unit
LC-MS/MS	tandem liquid chromatography mass spectrometry/mass spectrometry
LC/MS	liquid chromatography/mass spectrometry
LC	liquid chromatography
LIT	linear ion trap
LLE	liquid–liquid extraction
LOAEL	lowest-observed-adverse-effect level
LOD	limits of detection
LOEC	lowest observed effect concentration
LOQ	limits of quantification
MAE	microwave-assisted extraction
MAR	managed aquifer recharge
MAV	minimum acceptable value
MDMA	3,4-methylenedioxymethamphetamine
MDR	minimum data requirement
MF	microfiltration
MfE	ministry for the environment
MIW SIG	micropollutants in water special interest group
MOA	mode of action
MOE	margin of exposure
MP	microplastic
MS	mass spectrometry
MS/MS	tandem mass spectrometry
MSPD	matrix solid-phase dispersion
MTBE	methyl tert-butyl ether
MTD	minimum therapeutic dose
NBBSA	N-butylbenzenesulfonamide
ND	not detected
NDMA	N-nitrosodimethylamine
NER	non-extractable residue
NF	nanofiltration
NM	nanomaterial
NMR	nuclear magnetic resonance
NOAEL	no-observed-adverse-effect level
NOEC	no-observed-effect concentration
NOM	natural organic matter (present in mg L⁻¹ level)
NP	nanoparticle
NPEO	nonylphenol ethoxylate
NPE1	nonylphenol monoethoxylate
NPE2	nonylphenol diethoxylate
NSAID	non-steroidal anti-inflammatory drug
OECD	organization for economic development and cooperation
OPE	octylphenol ethoxylate
OPPT	Office for Pollution Prevention and Toxics
P2P	phenyl-2-propanone
PAH	polycyclic aromatic hydrocarbon
PBB	polybrominated biphenyl
PBDE	polybrominated diphenyl ether
PBT	persistent, bioaccumulative and toxic
PC	pharmaceutical
PCA	polychloro-n-alkane
PCB	polychlorinated biphenyl
PCE	tetrachloroethene
PCP	personal care product
PEG	polyethylene glycol
PET	polyethylene terephthalate
PFAS	perfluorinated alkyl substance
PFC	perfluorinated compound
PFCA	perfluorocarboxylic acid
PFOA	perfluorooctanoic acid
PFOS	perfluorooctane sulfonate
PFR	phosphorus flame retardants
PFSA	perfluorosulfonate acid
PM	particulate matter
PNEC	predicted no effect concentration
PoD	point of departure
POP	persistent organic pollutant
PPG	polypropylene glycol
PUB	public utilities board (Singapore)
PVC	polyvinyl chloride
REACH	registration, evaluation, authorisation and restriction of chemical substances
RMA	resource management act
RO	reverse osmosis
SAICM	strategic approach to international chemicals management
SBE	sewage-based epidemiology
SDME	single-drop microextraction
SDWA	Safe Drinking Water Act
SETAC-AU	Australasian society for ecotoxicology
SF	sand filtration
SIM	selected ion monitoring
SMAV	species mean acute value
SOA	secondary organic aerosol
SPE	solid-phase extraction
SPME	solid-phase microextraction
STP	sewage treatment plant
SWCNT	single-walled carbon nanotube
TBBPA	3,3′ ,5,5′-tetrabromobisphenol A
TBEP	tris(2-butoxyethyl) phosphate
TBT	tributyltin
TCE	trichloroethene
TCEP	tris(2-chloroethyl) phosphate
TCPP	tris(chloropropyl) phosphate
TCS	triclosan
TDCPP	tris(1,3-dichloroisopropyl)phosphate
TDI	tolerable daily intake
TEF	toxic equivalency factor
TEP	triethyl phosphate
THM	trihalomethane
TLC	thin-layer chromatography
TMS	trimethylsilyl
TNT	trinitrotoluene
TOF	time-of-flight
TP	transformation product
UF	ultrafiltration
UHPLC	ultra-HPLC
UNEP	United Nations Environment Programme
UPLC	ultraperformance liquid chromatography
U.S.	United States
USEPA	United States Environmental Protection Agency
USGS	U.S. Geological Survey
UV	ultraviolet
VOC	volatile organic compound
VTG	vitellogenin
WHO	World Health Organization
WQC	water quality criteria
WSH	water, sanitation, hygiene and health unit (WHO)
WW	wet weight
WWTP	wastewater treatment plant

Glossary

aerosol	colloid of fine particles of solid or liquid droplets suspended in a gas.
alkaloid	group of naturally occurring chemical compounds nitrogen-containing bases. Many of them produce physiological effects on humans and other animals.
antibiotics	medications that fight bacterial infections, inhibiting or stopping bacterial growth.
antimicrobials	biochemicals that kill or inhibit the growth of microorganisms including bacteria and fungi.
biochemical oxygen demand	a measurement of the amount of dissolved oxygen using aerobic microorganisms.
biocide	chemical substance or microorganism intended to destroy, deter, and render harmless, or exert a controlling effect on any harmful organism by chemical or biological means.
biodegradation	transformation of materials or molecules by bacteria, fungi, or other biological means.
biofiltration	filtration technique using a bioreactor containing living material to remove pollutants by biological degradation.
biomarker	is a measurable indicator of some biological state or condition. The term is also occasionally used to refer to a substance the presence of which indicates the existence of a living organism. They can be related to exposure or to toxic effects of environmental chemicals.
bioreactor	any manufactured or engineered device or system that contains living organisms such as bacteria or yeast.
biosolid	organic wastewater solids recovered from a sewage treatment that can be reused after suitable sewage sludge treatment.
contaminant	any physical, chemical, biological, or radiological substance or matter with an adverse effect on air, water, and soil.
corrosion	chemical reaction between refined metals and the surrounding environment, which converts them into a more chemically stable form, such as oxides, hydroxides, or sulfides and leads to their deterioration.
depressant drug	chemical compound that lowers neurotransmission levels, which is to depress or reduce arousal or stimulation in the brain.
detergent metabolites	chemical compounds formed when detergents are broken down by wastewater treatment or environmental degradation.
diffuse pollution	pollution that may be produced from widespread activities with no single discrete source.
disinfectants	a chemical agent used on non-living surfaces to destroy, neutralize, or inhibit the growth of disease-causing microorganisms.
disinfection by-products	chemical substances resulting from the interaction of organic matter in water with disinfection agents such as chlorine.
ecotoxicity	ability of a chemical or physical agent to affect ecosystems.
effluent	wastewater, treated or untreated, that flows out of a treatment plant, sewer, or industrial point source, such as a pipe. Generally refers to wastes discharged into surface waters.
endocrine disruptor	molecule that interferes with the endocrine system of living organisms and produces adverse developmental, reproductive, neurological, and immune effects.
ergotism	the effect of long-term ergot poisoning, traditionally due to the ingestion of the ergot alkaloids produced by the Claviceps purpurea fungus that infects rye and other cereals.
estrogenic compounds	natural or synthetic chemicals that can elicit an estrogenic response.
eutrophication	nutrient enrichment in bodies of water.
flame retardant	chemical added to several manufactured materials, which is able to inhibit or delay the spread of fire by suppressing the reactions produced in the flame or by forming a protective layer on the surface of the treated material.
fragrances	chemical substances that impart a sweet or pleasant odor.
global distillation	mechanism for transportation of persistent organic pollutants from warmer to colder regions by successive evaporation–deposition processes.
hepatotoxicity	damage of the liver parenchyma.
immision	effect of pollutants. The term “immission” means to send in. It denotes the external impact on something.
InChIKey	the IUPAC International Chemical Identifier is a unique text code assigned to a chemical substance, designed to facilitate searches in dabatases and the web.
insect repellents	chemical substances applied to skin or other surfaces to discourage insects from coming into contact with the surface.
LD₅₀	dose of a substance, in mg kg⁻¹, with a lethal effect on half the test animals to whom it is fed.
liquid–liquid extraction	separation process based on the different distribution of the components of a mixture between two immiscible liquid phases.
manure	organic matter, principally derived from excrement of animals except in the case of green manure. They are used as organic fertilizer in agriculture.
metabolites	products and intermediates of metabolism, produced when the body breaks drugs down. Traces of drugs consumed will end up in the sewer network either unchanged or as a mixture of metabolites. The term metabolite is usually restricted to small molecules.
microfiltration	membrane filtration process that uses membranes with pore sizes from 0.1–10 micrometers.
musk	term derived from the Sanskrit word “muska-s,” which means “testicle,” and refers to the fragrant of the apocrine glands of the male musk deer (Moschus moschiferus).
nanofiltration	membrane filtration process that uses membranes with pore sizes from 1–10 nanometers.
nanomaterial	materials where a single unit is sized in one, two, or three dimensions from 1–1,000 nanometers.
nanotechnology	study and application of extremely small size materials applicable in fields, such as chemistry, biology, physics, medicine, materials science, and engineering.
no observed effect concentration	the highest tested concentration of an effluent or a toxicant at which no adverse effects are observed on the aquatic test organisms at a specific time of observation.
nonylphenols	are classified within the organic compounds called alkylphenols. They are used in manufacturing surfactants, detergents, emulsifiers, solubilizers, pesticides, antioxidants, and lubricating oil additives.
organophosphorous compound	organic molecule containing phosphorous.
persistent organic compound	compound resistant to environmental degradation that adversely affects human health and the environment, and can accumulate and pass from species through the food chain.
pesticide	generic term for all plant-protection chemicals and biocides.
population	all individuals of a type within a specific area, which can be crossed among each other and therefore have a common genetic complement.
pharmaceuticals	chemical substances used in the prevention or treatment of physiological conditions.
plasticizer	chemical additives that increase the plasticity or fluidity of a material.
pollutant	any substance or energy introduced into the environment that produces undesired toxic effects.
poly aromatic hydrocarbons (PAHs)	a large group of chemical substances usually found in the environment as a result of incomplete burning of carbon-containing materials such as fossil fuels, wood, and garbage.
priority pollutant	regulate chemical pollutant.
reproductive hormones	a group of chemical substances, usually steroids, whose purpose is to stimulate certain reproductive functions.
semipermeable membrane	biological or synthetic membrane that allows certain molecules or ions to pass through it by diffusion.
size exclusion chromatography	a mixture of molecules in solution are separated by their size, and in some cases molecular weight through a gel.
solid-phase extraction	sample preparation procedure in which analytes are dissolved or suspended in a liquid phase and separated from other compounds using solid supports, usually contained in a cartridge-type device.
solvents	chemical solutions, other than water, capable of dissolving another substance.
steroids	a large group of fat-soluble organic compounds with a characteristic molecular structure, which includes many natural and synthetic hormones.
stimulant drugs	substances that temporarily increase alertness and energy in living organisms.
surfactant	chemical substance that lowers the surface tension between two liquids or between a liquid and a solid.
sweetener	natural or synthetic compounds that taste sweet.
teratogenic	triggering deformities.
toxin	is a poisonous substance produced within living cells or organisms; synthetic toxic substances created by artificial processes are thus excluded.
ultrafiltration	filtration through a semipermeable membrane forced by pressure or concentration gradients.
volatile organic compound	organic molecule with a high vapor pressure and a great tendency to evaporate.
xenobiotics	artificially manufactured substances, foreign matter in the biosphere.

Preface

The so-called contaminants of emerging concern, CECs, are defined as a group of substances, mostly organic compounds, that have been detected in water, soil, and air in very small concentrations, but are not yet subjected to restrictions of any kind. Despite the lack of any current regulation, special concerns have grown around them because of their potential effects on ecosystems and living organisms upon long-term exposition. Most of these compounds have been undetectable with conventional analytic tests for many years, but the development of more sensitive procedures has helped identifying them in water bodies, soils, and even fluids and tissues of vegetables and animals. Many of them remain in the environment after conventional waste treatment, as it happens in waste urban waters. Their chemical structure is of diverse origin, in many cases being related to common human activities such as personal hygiene, agriculture, livestock, and use of medical and pharmaceutical products, household or industrial goods, among others.

Terms such as constituents of CECs, microconstituents, trace organic pollutants, and other similar terminologies are often used in the literature for these classes of chemicals, which are here to stay and require proper attention. Our aim with this book is to describe the main families of such compounds, their characteristics, origin, fate, and detection methods and the state of the art related to emerging pollutants.

Granada, April 2017

J. Isac-García

F.G. Calvo-Flores

J.A. Dobado

Origin, Structure and Properties