Authors
Dr. Francisco G. Calvo-Flores
University of Granada
Department of Organic Chemistry
Severo Ochoa s/n
18071 Granada
Spain
Dr Joaquín Isac-García
University of Granada
Department of Organic Chemistry
Severo Ochoa s/n
18071 Granada
Spain
Dr. José A. Dobado
University of Granada
Department of Organic Chemistry
Severo Ochoa s/n
18071 Granada
Spain
Cover: Photo courtesy of Laura Bustos-Sánchez
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Print ISBN: 978-3-527-33876-4
ePDF ISBN: 978-3-527-69123-4
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All substances are poisons; there is none which is not a poison. The right dose differentiates a poison and a remedy.
This early observation concerning the toxicity of chemicals was made by Paracelsus (1493–1541) and it serves as a good starting point for the discussion on micropollutants.
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 |
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. |
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
Finally, we would like to give our special thanks to Dr Francisco J. Martín Martínez for his revision of part of this work, to Mr David Nesbitt for his invaluable work on the revision of the English version of the manuscript, and to Mrs Laura Bustos-Sánchez for creating the front cover photo.