APPENDIX 1 NOMENCLATUREOFORGANOHALOGENS

Assigning unique names to the tens of thousands of organic compounds in existence is a massive undertaking and requires that very strict procedures be followed. To those unfamiliar with the conventions of nomenclature, the cumbersome names of organic chemieals seem indecipherable but these conventions have been carefully formulated for sirnplicity and efficiency and so a basic understanding is quite easily achieved. Of the several nomenclature systerns in use today, the IUPACsystem is probably the most widely accepted. IUPAC nomenclature of any given structure frrst requires the identification of the parent compound of which the compound under study can be considered a derivative. The names and attachment positions of the various subgroups are then worked out and prefixed with the parent name. The diagrams presented below are in the style used by chemists; neither carbon nor hydrogen atoms are shown. The lines of the diagram run between carbon atorns, or between carbon and another atom or group of atoms. Hydrogen atoms are not represented at all; a carbon atom can make four chernical bonds and where fewer than four are shown, it is assumed that hydrogen atoms fill the remaining places. As examples, Figure A1.1 represents the molecule CHCl=CH2 and Figure A1.2 represents a six-carbon chain, CH3-CHCl-CHrCHF-CH2-

CHJ.

Details and examples of the classification of the organohalogens according to these rules are described below. For the purposes of explanation it is convenient to divide the organohalogens into two groups: the aliphatic and aromatic halogentated hydrocarbons.

Al.l Aliphatic hydrocarbons

Aliphatic compounds do not contain any conjugated ring structures; they may, however, be cyclical (alicyclic hydrocarbons). The aliphatic hydrocarbons consist of three classes; the alkanes, the alkenes and the alkynes. The alkanes are fully saturated; that is, all the carbon atoms are joined by single bonds rather than multiple bonds. The name of an alkane is made up of two parts; the first designates the length of the carbon chain and the second is characteristic of the class of hydrocarbon ( -ane in this case ). The alkanes are therefore named as follows:

No. of carbons Name No. of carbons Name 1 methane 9 nonane 2 ethane 10 decane 3 propane 11 undecane 4 butane 12 dodecane 5 pentane 13 tridecane 6 hexane 14 tetradecane 7 heptane 15 pentadecane 8 octane 16 hexadecane

406 Chlorine and the Environment

The alkenes have at least one carbon-carbon double bond in their structure. They may be distinguished from the alkanes by names ending in -ene rather than -ane (Figure Al.l).

Cl~ Figure A.l.l: Chloroethene (vinyl chloride).

Alkynes contain a carbon-carbon triple bond; their namesend in -yne.

A 1.1.1 SUBSTITUTED ALIPHA TIC COMPOUNDS

The parent name of a substituted aliphatic compound depends on the Iongest unbranched chain of carbon atoms as described above. The positions of the subgroups are then numbered along that chain so that the lowest possible numbers are used. Positions of multiple carbon-carbon bonds are also indicated in this way. Where there are two or more of the same subgroup, commas are used to separate the position numbers (locants). Locants are separated from the subgroup names by hyphens (Figures A1.2- A1.4).

F

Cl Figure Al.2: 2-chloro-4-fluorohexane (not 3-jluoro-5-chlorohexane).

Br

Figure Al.3: 2-bromo-but-1-ene.

Nomenclature of Organahalogens 407

Cl

Figure A 1.4: 1,1, 1-Trichloroethane.

For alicyclic compounds there is no need to specify the position of a single subgroup (e.g. chlorocyclohexane), but where there is more than one substituent on the ring the one with the highest priority (usually the heaviest) is taken tobe number 1 and all the others are numbered from there. Again, the direction of the numbering is such that the lowest possible numbers are used (Figures Al.S- Al.7).

Figure A1.5: Chlorocyclohexane.

Figure A 1. 6: 1-Chloro4-ethyl-2-methylcyclohexane.

408 Chlorine and the Environment

Cl Cl

Figure Al. 7: Hexachlorocyclohexane (HCH). Also incorrectly named benzene hexachloride (BHC).

Al.l.2 FUNCTIONAL GROUPS

Functional groups are chemical subgroups which, although they may contain carbon and hydrogen, also contain other elements. Some functional groups are correctly named only as preftxes to the parent name (Figure Al.8). The halogens are examples, as are the following subgroups:

Formula -ClO -Cl02 -Cl03 -OR

PrefixName chlorosyl chloryl

perchloryl R-oxy

/o~c~0 Figure Al.8: 1-Chlorosyl-3-methoxypropane.

Some functional groups can also be named as suffixes. For example, compounds containing an -OH group may be referred to either as hydroxy- compounds or as alcohols, in which case the -e at the end of the name is replaced by -ol (Figure A 1.9).

Br ~OH

Figure AJ.9: 1-Bromoethan-2-ol (or 1-bromo-2-hydroxyethane).

Nomenclature of Organahalogens 409

Some of the principal functional groups and their corresponding prefixes and suffixes are listed below (it should be noted that halogens as a group are denoted by the Ietter X; similarly R (above) represents an unspecified hydrocarbon chain.)

Formula Suffix Name Prefix Name cations -onium -onio anions -ate, -ide -ato, -ido -COOH -oic acid carboxy -COOH -carboxylic acid carboxy -COX -oyl ( -yl) halide haloformyl -COX -carbonyl halide haloformyl

-CONH2 -amide, carbamoyl -CONH2 -carboxamide carbamoyl

-CONHCO -imide -CHO -al OXO

-CHO -carbaldehyde formyl >C=O -one OXO

>C=S -thione thioxo -OH -ol hydroxy -NHz -amine amino =NH -imine -imino

In the above list 'C'indicates that the carbon is not included in the prefix or suffix name, but in the parent name. The compounds are listed in order of priority. Where a compound contains more than one functional group, the one of highest priority is indicated by the suffix, and the other by prefixes.

A1.2 Aromatic hydrocarbons

These are based on the benzene ring. The siruplest aromatic compounds are named as derivatives ofbenzene (Figures Al.lO & Al.ll).

Figure Al.JO: Benzene.

410 Chlorine and the Environment

Cl

Cl Cl

Figure A 1.11: H exachlorobenzene.

However, when the benzene ring is a substituent of another parent compound, it is referred to as phenyl. As with alicyclic aliphatic compounds, the positions on a phenyl ring are numbered from the substituent of highest priority, using the lowest numbers possible (Figures Al.12 & Al.13).

Cl

Figure A.12: 2-Ch/oro-4-pheny/butane.

Cl

F Cl

Figure A 1.13: 1 ,2-Dichloro-4-jluorobenzene (not 1,5-dichloro-4-jluorobenzene).

For di-substituted phenyl rings, the terrns ortho (o), meta (m) and para (p) are used to indicate subgroups at the 1,2-, 1,3- and 1,4- positions respective1y.

Phenolsarephenyl alcohols (Figures Al.14 & A1.15). The locant ofthe -OH group is designated as 1.

Nornene/ature of Organahalogens 411

Cl OH

Figure A 1.14: 3-Chlorophenol ( or m-chlorophenol).

Cl Cl

HO Cl

Cl Cl

Figure A1.15: Pentachlorophenol.

Application of the basic rules described above allows the naming of quite complex structures, eg DDT. DDT stands for dichlorodiphenyltrichloroethane. The full systematic name is: 1,1, 1-trichloro-2,2-bis(p-chlorophenyl)ethane. From this it can be deduced that the parent compound is ethane. Onto this .are added three chlorines at the first carbon and two p-chlorophenyl groups at the second carbon. Thus the structure of DDT (Figure Al.16) is:

Cl

Cl--t---CI

Cl Cl

Figure A1.16: DDT.

412 Chlorine and the Environment

A1.3 Isomers, Stereoisomers and congeners

Isomersare compounds with the same stoichiometric formulae (i.e. the same numbers of carbon, hydrogen, chlorine etc atoms in one molecule) but whose atoms are not joined at the same positions, eg 1,1,1-trichloroethane and 1,1,2-trichloroethane.

Stereoisomers have the same constituent atoms bonded together at the same positions. They vary only in the three-dimensional arrangement of these bonds in relation to one another. Stereoisomersare indicated by such preflxes as (R), (S), cis, trans, (E) or (Z). Consideration of the conventions for the nomenclature of Stereoisomers is not thought to be necessary in this general discussion; details can be found in the IUPAC rules.

Congeners are members of a group of closely related compounds such as the chlorophenols or dioxins. The basic structure of the compound is constant but the number and position of the halogenated substituents varies.

A1.4 Trivialand unsystematic names

Due to the cumbersome names of some compounds, and for historical reasons, there are a !arge number of terms which are still widely used and recognised, although not correct in the strictest sense.

Trivial name Systematic Name vinyl chloride 1-chloroethene

vinylidene chloride 1,1-dich1oroethene methylene halide dihalomethane

formic methanoic acetic ethanoic

ethylene ethene acetylene ethyne

haloform (e.g. chloroform) trihalomethane styrene phenylethene

phosgene carbonyl chloride epichlorohydrin 1-chloro-2,3-epoxypropane

toluene methyl benzene Table A.l: Some common chemieals and their systematic names.

Al.S More complex structures

It is not the intention to explain here the methods for naming the more complex organic structures such as polynuclear or heterocyclic systems. lndeed, under most circumstances it is preferable to refer to the pesticides by trivial or trade names since the full name becomes cumbersome. Chlordane and heptachlor are included here as examples (Figures A1.17 & Al.18); others may be found in Chapters 10.

Nomenclature of Organohalogens 413

Cl

Cl

Figure A 1. 1 7: Chlordane.

Figure A 1. 18: Heptachlor.

APPENDIX 2 RELATIVE PROPERTIES OF THE HALOGENS

Fluorine Chlorine Bromine lodine Astatine

Symbol F Cl Br I At Atomic number 9 17 35 53 85 Atomic weight 18.998 35.453 79.904 126.905 (210) Valence e· 2s22p5 3s23p5 4s24p5 6s26p5 7s27p5

mp, oc -220 -101 -7.3 114

bp, oc -188 -34 58.8 184

density 1.81 gl' 1 3.21 g1'1 3.12 g cm·3 4.94 g cm-3

Atomic volume 12.8 14.5 23.5 25.7 Atomic radius, pm 64 99 114 133 Ionradius (-I) 136 181 195 216 Pauling EN 4.0 3.0 2.8 2.5 2.1 Std potential (a) +2.87 +1.36 +1.07 +0.615 +0.3

Oxidation numbers -I -I to +7 -I to +7 -I to +7

Ionisation energy 1680 1254 1139 1113 897

Isolated by Moisson Scheele Balard Courlais CMS

Date of isolation 1886 1774 1826 1811 1940

rpw pure 0 2 02F2 (el) None (i) None (i) None (i) rpw H20 HF, Oz. 03 HCI& HBr& Hl & HOl

HOC! HOBr rpwN2 None None None None

rpw H2 HF HCI HBr HI Colour of element Pale Yellow- Dark red Black

yellow green

Energiesand heats are in kJ/mol; atomic weight in parentheses isthat ofthe most

stable isotope; rpw = reaction product with; a = standard electrode potential for reaction X2 + 2 e- 7 2X- (reaction F2 + H2 7 2HF); CMS = Corson, McKenzie and Segn?; i = indicates oxides, etc., made by indirect methods; el = electric discharge.

After Kotz, lohn C. & Purce/1, Keith F. (1987) Chemistry & Chemica/ Reactivity, CBS College Publishing, USA. pp 848-856.

APPENDIX 3 SI UNITS AND CONVERSION FACTORS

A3.1 SI concentration units

kilogram kg 1x103g 1000g gram g 1g 1g milligram mg 1x1 0"3g 0.001g microgram J.!g lxl0-6g 0.000001g nanogram ng lxl0-9~ 0.000000001g picogram pg 1xl0"1 g 0.000000000001g femtogram fg lx10-15g 0.000000000000001 g attogram ag 1x10-18g 0.000000000000000001g

parts per million ppm mg/kg J.!glg mg/1 J.lg/ml parts per billion ppb J.lglkg ng/g J.lg/1 ng/ml parts per trillion ppt nglkg pg/g ng/1 pg/ml parts per quadrillion ppq pg/kg fg/g pg/1 fg/ml

A3.2 Conversion factors

Length centimetre in eh centimetre in eh

2.54 1 1 0.39 kilometre mile kilometre mile

1.61 1 1 0.62 metre yard metre yard

0.9144 1 1 1.094 Weight/Mass

metric tonne million US lbs metric tonne million US lbs 454 1 1 0.0022

gramme ounce (imp) gramme ounce (lmp) 28.35 1 1 0.04

kilogramme lb kilogramme pound (Imp) 0.45 1 1 2.20

metric tonne ton (long) metric tonne ton (long) 1.016 1 1 0.9842

Volume

litre pint litre pint (imp) 0.568 1 1 1.76

litre gallon litre gallon (imp)

4.55 1 1 0.22

Acyl: a term for carboxylic radicals RCO, R being aliphatic. Adduct: the addition product of a reaction between chemicals.

GLOSSARY

Adrenal cortex: the adrenal glands' outer part, which secretes corticosteroids etc. Aetiology: investigation of the causation of a disease or disorder. Agent Orange: a mixture of 2,4-D and 2,4,5-T herbicides, used extensively by the US army to destroy tree cover during the Vietnam War. Agonist: a substance initiating a physiological response when combined with an enzyme receptor. Ah receptor: aryl hydrocarbon receptor. Alopecia: hair loss. Analogue: compound with molecular structure closely similar to that of another. Androgen: any of a group of male sex hormones, incl. testosterone, involved in developing and maintaining male sexual characteristics. Aneuploidy: a condition (e.g. Down's syndrome) where less or more than a complete set of chromosomes is found in each cell of an individual. Angiosarcoma: malignant tumour containing many fine blood vessels. Antagonist: a substance that partially or entirely opposes the action of another. Arthralgia: pain in a joint. Aryl: a term for aromatic monovalent hydrocarbon groups. Ataxia: loss of control of movements. ATP-ase: any of a group of enzymes that can synthesise A TP from ADP and phosphate using energy derived from a proton gradient across a membrane, and can hydrolyse ATP to pump protons across the membrane. Basal cell: cell in lowest part of a stratified tissue e.g. epidermis, from which that tissue is renewed. Bioaccumulation: accumulation of a compound in an animal through absorption from its diet. Bioconcentration: accumulation of a compound in an organism through absorption from its immediate environment. Biomagnification: an increase in a compound's concentration in organisms with increasing trophic Ievel. Blepharitis: inflammation of the eyelids. Captive production: use of an industrial chemical at the site of its production. Catechol: 1 ,2-hydroxybenzene. Precursor of adrenaline and guaiacol. Catechloamine: any catechol-derived compound ( e.g. adrenalin, dopamine ). Chelate: a compound (usually organometallic) in which a Iigand bonds to a central atom at two or more points. Chloracne: skin disease resembling severe acne, caused by exposure to chlorinated chemicals, particularly dioxins. Chlorinolysis: breaking up of a substance by reaction with chlorine. Cholinergic: ( of nerve fibres) secreting acetylcholine as a transmitter substance. Cis-, trans-: referring to the position of a substituent adjacent to a carbon-carbon double bond. Clastogenic: giving rise to or inducing disruption or breakages, as of chromosomes.

420 Chlorine and the Environment

Congener: member of a group of compounds having the same carbon skeleton, but with differing numbers and positions of substituent chlorine atoms. Corticosteroid: any of a group of steroid hormones produced in the adrenal cortex. Corticotrophin: hormone secreted by the pituitary gland and stimulating the adrenal cortex. Cyanogen: C2N2; poisonous gasintermediate in manufacture ofmany fertilisers. Cyanosis: bluish discoloration of skin caused by presence of oxygen-deficient blood. Cytochrome P-450: specialised electron transporting protein, involved in hydroxylation reactions. Cytogenetics: study of inheritance in relation to the structure and function of cells. Depuration: process of purification. Dicofol: 2,2,2-trichloro-1, 1-bis( 4-chlorophenyl)-ethanol, a pesticide. Dicotyledon: any flowering plant whose embryo bears two leaves. Disproportionation: a reaction in which a single compound is both oxidised and reduced. Dopamine: an amine present in the body as a neurotransmitter and precursor of adrenalin and other substances. Dyscrasias: any disordered condition ofthe body, esp. ofits fluids. Dyspnea: difficult or laboured breathing. Elastomer: material, usually synthetic, having elastic properties akin to rubber. Emphysema: enlargement oflung air sacs causing breathlessness. Enantiomer: an optical isomer; a mirror-image of another isomer, that rotates plain polarised light in the opposite direction. Only one of a pair of enantiomers is biologically active in certain cellular processes. Endocrine: ( of a gland) secreting directly into the blood. Endogenous: growing or originating from within. Endometriosis: appearance ofthe womb's membrane lining outside the womb. Endoplasmic reticulum: network of membranaus tubules within a eukaryotic cell's cytoplasm, continuous with the nuclear membrane and usually having ribosomes attached. Eosinophilic: readily stained by the rose-coloured dye eosin. Epifauna: bottom-dwelling aquatic animals. Epinephrine: adrenalin. Epithelial: ofthe tissue forming the outer layer ofthe body surface and lining the alimentary canal and other hollow structures. Epizootie: epidemic in an animal population. Epoxide: compound containing an oxygen atom bonded in triangular arrangement to two carbon atoms. Erythemal: sunburning. Ester: compound formed from an alcohol and an acid. Eukaryote: organism consisting of a cell or cells in which the genetic material is DNA in the form of chromosomes contained within a distinct nucleus. Exogenous: growing or originating from outside. Flavonoid: any of a group of compounds, including many water-soluble plant pigments, which contain a C6-C3-C6 skeleton, the C6 parts forming benzene rings, and often form oxygen-containing rings.

Glossary 421

Freon: any of a group ofhalogenated hydrocarhons containing fluorine, chlorine and

sometimes hromine, used in aerosols, refrigerants etc. Friedet-Crafts reaction: reaction of halogenoalkanes or acyl halides with aromatic hydrocarhons in the presence of anhydrous aluminium chloride, yielding alkyl suhstituted henzene hydrocarhons and aromatic ketones. Glomerulsclerosis: fihrosis and scarring within kidney leading to inadequate renal function. Glucocorticoid: a steroid endocrine secretion produced hy the adrenal cortex,

influencing the metaholism of carhohydrates and proteins. Glucuronic acid: HOOC(CHOH)4CHO. Widely distrihuted in plant and animal

tissues in complex polysaccharides. Precursor ofxylose. Participates in elimination of

lipophilic xenohiotics hy conjugating with an added or revealed functional group to

allow excretion in urine. Glutathione: a tripeptide, glu-cys-gly, found in many tissues esp. red hlood cells

where it acts as a huffer for haemogluhin, exists in reduced or oxidised form and acts as a coenzyme in certain redox reactions. Glycol: a diol (alcohol containing two hydroxyl groups on each molecule), esp.

ethylene glycol. Haematin: hluish-hlack derivative ofhaemoglohin, formed hy removal ofthe protein

part and oxidation of the iron atom. Haematuria: hlood in urine. Haemapoietic: hlood-forming. Haemolytic anaemia: any of a group of acute or chronic anaemias characterised hy

shortened survival and inadequate replacement of red hlood cells. Henry's Law: the amount of a gas ahsorhed hy a given volume of a liquid at a given

temperature is directly proportional to the pressure of the gas. Hepatocyte: a liver cell. Hepatomegaly: enlargement ofthe liver. Histopathology: microscopical anatomy of diseased tissues. Homologue: a compound in a series having the same functional group hut differing in

composition hy a fixed group of atoms. Humoral immunity: immune responses involving antihoclies in hody fluids as distinct

from cells. Hygroscopic: tending to ahsorh moisture from the air. Hyperadrenocorticism: condition characterised hy ahnormally increased secretion of

adrenocortical hormones. Hyperbilirubinemia: excess ofthe hile pigment hiliruhin in the hlood.

Hyperkeratosis: overgrowth ofthe homy layer ofthe skin. Hyperplasia: enlargement of an organ or tissue from increased production of cells.

Hypophysis: pituitary gland. IgM: high molecular weight immunoglohulin, the first antihoclies to he synthesised

and released after a primary antigenic stimulation. Interstitial: (hiol.) ofthe spaces hetween cells. Intraepithelial: occurring within sheet oftightly-hound cells lining extemal and

intemal surfaces ( e.g. epidermis, mucous memhrane surfaces, gut, duct and gland

linings) ofmulticellular organisms. lschaemic: reducing hlood supply to part ofthe body.

422 Chlorine and the Environment

lsocyanate: compounds containing the group CNO. Precursors for polyurethane resins. Isomer: a compound with the same chemical formula as another, but with a different position of atoms. Keratoconjunctivitis: inflammation or comea and conjunctiva. Kow: octanol water partition coefficient. Leutenising hormone: glycoprotein hormone secreted by the anterior pituitary gland, prompting female ovulation and menstruation cycles and androgen secretion in males. Lewis acid: any substance accepting an electron pair as an acid, e.g. in a complex­forming reaction.; need not be a conventional acid. Lymphoreticulosarcoma: malignant tumour/s ofthe lymphoid and/or reticulo­endothelial systems. Malonic acid: metabolic poison occurring as a metabolism end product in some plants, which blocks cellular respiration. Mass spectrometry: analytical technique involving detection of charged molecular fragments. Melanin: a dark brown to black pigment occurring the skin, hair and the iris of the eyes and is responsible for the tanning of sun-exposed skin. Melanoma: a usually malignant tumour ofthe melanin-forming cells, usually in the skin. Mercapturic acid: a cysteine conjugate of an aromatic compound formed initially as a glutathione conjugate in the liver and excreted in urine. Mesothelioma: benign or malignant tumour derived from mesothelial tissue (peritoneum, pleura or pericardium). Meta-substitution: substitution of the 1- and 3- positions of a benzene ring. Methaemoglobinaemia: blood disorder, causing blueness and breath shortage in human sufferers, where haemoglobin is oxidised to methaemoglobin, which is incapable of carrying oxygen. Microsomal: of the fraction of tiny sub-cellular particles produced during differential centrifugation and consisting mainly of membranes and ribosomes from the endoplasmic reticulum (q.v.). Mitochondria: organelles found in most eukaryotic (q.v.) cells, containing enzymes for respiration and energy production. Mitosis: cell division. Monocotyledon: any flowering plant whose embryo bears a single leaf. Mordant: a fixative for dyes or stains in the textile industry. Moribillivirus: measles-like virus (includes agents ofmeasles, canine distemper and rinderpest). Myeloma: a malignant tumour ofthe hone marrow. Necrosis: tissue death caused by disease or injury. Nematode: slender, unsegmented, parasitic or free-living worm ofphylum Nematoda; roundworm. Nephrosis: kidney disease characterised by degenerative lesions ofrenal tubules. Neuritis: nerve inflammation. Neuropathy: disease or dysfunction of one or more peripheral nerves, typically causing numbness or weakness.

Glossary 423

Non-Hodgkin's Iymphoma: any of a group of malignant tumours arising from lymphoid components of the immune system and characterised by painless enlargement of one or more peripherallymph nodes. Norepinephrine: noradrenaline, a hormone released by adrenal medulla and sympathetic nerve endings as a neurotransmitter. Oedema: excess ofwatery fluid in the cavities or tissues ofthe body. Osophageal: ofthe gullet. Ortho-substitution: substitution of the 1- and 2- positions of a benzene ring. Para-substitution: substitution of the 1- and 4- positions of a benzene ring. Pediculocide: louse killer. Periphyton: plants and animals adhering to parts of rooted aquatic plants. Peroxisome: an organelle of eukaryote cells located near mitochondria and chloroplasts and apparently involved in cellular respiration. Pheromone: chemical substance secreted and released by an animal for detection and response by another, usually ofthe same species. Phosphazene: (PNR2)n. Cyclic or chain compound containing altemating P and N atoms with two substituents on the P atoms. Phosphonates: the ions arising from phosphonic acid (H3P03).

Photolysis: decomposition or dissociation of molecules by the action oflight. Phytotoxic: poisonous to plants. Pineal melatonin: hormone thought to inhibit reproductive activities and be involved in control of circadian rhythms, secreted by the pineal gland on the forebrain. Pleural: of the membrane lining the ehest and extending to cover the lung surface. Polyol: containing more than one hydroxyl group. Polyuria: excessive secretion ofurine. Porphyria: abnormal metabolism of porphyrin pigments and their excretion in urine. Porphyria cutanea tarda: disturbance of porphyrin metabolism, brought on by disease or environmental factors, characterised by cutaneous photosensitivity and consequent scarring, hyperpigmentation and altered hair growth; hepatic enzyme activity is reduced. Proteinurea: presence of proteins in the urine. Pruritus: severe itching of the skin. Pterygium: encroachment onto the comea from the side of a thickened, vascular, wing-shaped area ofthe conjunctiva. Pyrethroid: a group of chemieals ofnatural and synthetic origin, including pyrethrum, many of which have insecticidal properties. Pyrolysis: chemical decomposition brought about by heat. Raynaud's phenomenon: constriction ofblood supply to digits producing a white fing er or toe, often in response to cold, when appearing as a symptom of disease. Receptor: molecular structure within or on surface of cell characterised by ( a) selective binding of a particular substance and (b) a specific physiological response that accompanies binding. Retinoid: pertaining to retinol (vitamin A) and related compounds. Retinol: an isoprenoid alcohol, is important for vision and for animal growth and reproduction. Sarcoma: malignant tumour of connective or other non-epithelial tissue.

424 Chlorine and the Environment

Sclera: the eyeball's tough outer coat, white in humans; it is continuous with the comea and, posteriorly, the outer sheath ofthe optic nerve. Sequestrant: agent taking part in sequestration, the process of forming co-ordination complexes of an ion in solution. Sequestration often involves formation of chelate complexes and may be used to prevent chemical effects of an ion without removing it from solution or to supply ions in a protected form. Shikimic acid: aromatic carboxylic acid, intermediate in synthesis of aromatic amino acids in microorganisms. Sinter: substance caused by coalescence from powder into solid by heating. Sizing: use of size (a gelatinous solution for stiffening or glazing textiles, etc.). Squamous: relating to scales on animals or plants. Stuffing box: a box packed with material, to allow the working of an axle while remaining airtight. Substrate: the substance on which another one acts; the surface or material on which any particular organism grows. Superfund: popular name for the U.S. Comprehensive Environmental Response, Compensation and Liability Act (1980). Surfactant: substance which reduces surface tension. Synapse: ajunction oftwo nerve cells, consisting ofa minnte gap across which impulsespass by diffusion of a neurotransmitter. T4: thyroxine; major hormone produced by thyroid gland, transported in blood serum; regulatory function incl. control of cell metabolism rates and CNS maturation. T -cell: a lymphocytic white corpuscle of a type produced or processed by the thymus gland and active in the immune response. Teratogen: agent or factor causing malformation of an embryo. Thermolysis: decomposition by heat action. Toluene: methylbenzene. Xylene: dimethylbenzene. Yucheng: 1978 poisoning incident in Taiwan, caused by contamination of cooking oil withPCBs. Yusho: 1968 poisoning incident in Japan, caused by contamination of cooking oil with PCBs.

2,4,5-T: 2,4,5-trichlorophenoxyacetic acid; herbicide 2,4-D: 2,4-dichlorophenoxyacetic acid; herbicide ACTH: adrenocorticotrophic hormone ADI: acceptable daily intake ADT: air dried tonne (metric) AHH: aryl hydrocarbon hydroxylase AOC: assimilable organic carbon AOX: adsorbable organic halogen APR: Association of Postconsumer Plastics Recyclers

ABBREVIATIONS

ASMO: Working group on Assessment and Monitaring (OSPAR Convention) ATP: adenosine triphosphate, energy source within cells BAF: bioaccumulation factor BATNEEC: Best Available Technology Not Entailing Excessive Cost BCC: basal cell carcinoma BCF: bioconcentration factor BCPS: bis( 4-chlorophenyl)sulphone BGA: Bundesgesundheitsamt, German Federal Health Office BHC: benzene hexachloride, incorrect name for HCH (hexachlorocyclohexane) BOF: basic oxygen furnace c.: circa, approximately CDC: Centers for Disease Control (US) CERCLA: Comprehensive Environmental Response, Compensation And Liability Act, 1980 (US) CFC: chlorofluorcarbon CNS: central nervous system COD: chemica1 oxygen demand CPVC: chlorinated PVC DBCP: dibromochloropropane DBP: dibutyl phthalate DBP: disinfection byproduct DDD: 1, 1-dichloro-2,2-bis( 4-chlorophenyl)ethane, metabolite of DDT DDE: 2,2-dis(p-chlorophenyl)-1,1-dichloroethylene, metabolite ofDDT DDT: dichlorodiphenyltrichloroethane (insecticide) DEHA: diethylhexyladipate DEHP: diethylhexyl phthalate DHHS: Department of Health and Human Services (US) DIFF: Working Group on Diffuse Sources (OSPAR Convention) DNA: deoxyribonucleic acid DOA: dioctyladipate DTPA: pentetic acid; N,N-Bis{2-[bis(carboxymethyl)-amino]ethyl]glycine DYNAMEC: Dynamic selection and prioritisation mechanism (OSPAR Convention) EA: Environment Agency (UK) EAF: electric arc furnace EC: European Communit)' or European Commission

426 Chlorine and the Environment

EC50: effective concentration for 50% of the test population ECB: European Chemical Bureau ECF: eiemental chlorine free ECG: electrocardiogram ECU: European Currency Unit EDB: ethylene dibromide EDC: ethylene dichloride EDTA: edetic acid; N,N'-1,2-ethanediylbis[N-(carboxymethy/)glycine] EEA: European Environment Agency EEC: European Economic Community EINECS: European Inventory of Existing Commercial Substances EOCI: Extractable organochlorines EOX: extractable organic halogen EPA: Environmental Protection Agency EROD: 7-ethoxyresofurin-o-deethylase, hepatic enzyme EU: European Union FAO: Food and Agriculture Organisation (United Nations) FDA: Food and Drug Administration (US) FRG: Federal Republic ofGermany FSH: follicle stimulating hormone GABA: gamma-arninobutyric acid GC/MS: gas chromatography/mass spectrometry GC: gas chromatography GDP: Gross Domestic Product GLEMEDS: Great Lakes Embryo Mortality, Edema And Deformity Syndrome GWP: global warrning potential HCB: hexachlorobenzene HCBD: hexachlorobutadiene HCFC: hydrochlorofluorocarbon HCH: hexachlorocyclohexane HDPE: high density polyethylene HELCOM: Helsinki Commission- Baltic Marine Environment Proteerion Commission HEOD: dieldrin (1,2,3,4,10,10-hexachloro-6,7-epoxy-1,4,4a,5,6,7,8,8a-octahydro­endo-l ,4-exo-5 ,8-dimethanonaphthalene) HFC: hydrofluorocarbon HHC: halogenated hydrocarbon HMIP: Her Majesty's Inspectorate ofPollution (UK) HpCDD: heptachlorodibenzo-p-dioxin HPVC: high production volume chemical HSE: Health and Safety Executive (UK) HxCDD: hexachlorodibenzo-p-dioxin HxCDF: hexachlorodibenzofuran HxCN: hexachloronaphthalene IARC: International Agency for Research on Cancer ICMESA: Industrie Chimiche Meda Societa Azionaria, Seveso, Italy ICRCL: Interdepartmental Committee on the Redevelopment of Contaminated Land

(UK) IJC: International Joint Commission (US/Canada) IPCS: International Programme on Chemical Safety (WHO) IPPC: Integrated Pollution Prevention and Control (EC) ITEQ: International Toxic Equivalents IUPAC: International Union ofPure and Applied Chemistry IVM: integrated vector management Kow: octanol/water partitioning coefficient kt: kilotonne (= one thousand tonnes) LBS: Land-based Sources Protocol (Barcelona Convention) LC: London Convention 1972 (on waste dumping at sea) LC5o: lethat concentration for 50% of test population LD50: lethat dose for 50% of test population LDPE: low density polyethylene LH: leutenising horrnone LMM: lentigo maligna melanoma LRTAP: Long Range Transport of Atmospheric Pollutants LS: liquid steel MAFF: Ministry of Agriculture, Fisheries and Food (UK) MCL: maximum contaminant level MFO: mixed function oxidase MMC: Ministerial Meeting ofthe OSPAR Commission MPL: maximum perrnissible level MSW: municipal solid waste ND: not detected

Abbreviations 427

NIEHS: National Institute ofEnvironmental Health Seiences (US) NM: nodular melanorna NMSC: non-melanoma skin cancer NOEC: no observed effect concentration NOEL: no observed effect Ievel NPL: National Priority List (US) NRA: National Rivers Authority (UK) NRC: National Research Council (US) NTP: National Toxicology Programme (US) OCDD: octachlorodibenzo-p-dioxin ODP: ozone depletion potential OECD: Organisation for Economic Cooperation and Development OSHA: Occupational Safety and Health Administration (US) P AH: polynuclear aromatic hydrocarbon P ARCOM: Paris Commission PBB: polybrominated biphenyl PBDE: polybromimated diphenyl ether PCB: polychlorinated biphenyl PCDD: polychlorinated dibenzo-p-dioxin PCDE: polychlorinated diphenyl ether PCDF: polychlorinated dibenzofuran PCDPS: polychlorodiphenyl sulphide

428 Chlorine and the Environment

PCE: perchloroethylene, tetrachloroethene PCN: polychlorinated naphthalene PCP: pentachlorophenol PCQ: polychlorinated quaterphenyl PCT: polychlorinated terphenyl PCT A: polychlorothianthrene PeCDD: pentachlorodibenzo-p-dioxin PeCDF: pentachlorodibenzofuran (also PnCDF) PEL: permissible exposure limit (US) PERIPERC: perchloroethylene, tetrachloroethene PET: polyethylene terephthalate PIC: Prior Informed Consent PIC: product of incomplete combustion PMMA: polymethyl methacrylate PnCDF: pentachlorodibenzofuran (also PeCDF) PnCN: pentachloronaphthalene POP: persistent organic poilutaut PPS: poly(phenylene sulphide) resin PRAM: Working group on Programmesand Measures (OSPAR Convention) PRPs: Potentially Responsihle Parties (US) PVC: polyvinyl chloride RCRA: Resource Conservation Recovery Act (US) RNA: ribonucleic acid SARA: Superfund Amendments and Reauthorisation Act 1986 (US) SCC: squamous cell carcinoma SMR: standardised mortality ratio SSM: superficial spreading melanoma TCDD: tetrachlorodibenzo-p-dioxin TCDF: tetrachlorodibenzofuran TCE: trichloroethene TCF: totally chlorine free TCP: 2,4,5-trichlorophenol TDI: tolerable daily intake TEF: Toxicity Equivalence Factor TEQ: Toxic Equivalent THM: trihalomethane TIE: toxicity identification evaluation TOC: total organic carbon TOSCA: Toxic Substauces Control Act (US) TOX: total organic halogen tpa: tonnes per annum TRI: Toxics release inventory TT3, TT4: total triiodothyronine, thyroxine (thyroid hormones) TUR: Toxics use reduction UN: United Nations UNECE: United Nations Economic Council For Europe UNEP: United Nations Environment Programme

USEP A: United States Environmental Protection Agency UV: ultra-violet VC: vinyl chloride, also known as VCM, vinylchloridemonomer VCM: vinyl chloride monomer; another name for vinyl chloride VDC: 1, 1-Dichloroethene, vinylidene chloride VETF: Virtual Elimination Task Force (US/Canadian IJC) VOC: volatile organic compounds WHO: W orld Health Organisation WWF: World-Wide Fund for Nature

Abbreviations 429