Halogenated Aliphatic Hydrocarbons

Large amounts of halogenated hydrocarbons (HHCs), including vinyl halides, are produced in massive amounts in the USA (Table 2). These HHCs can include alkyl halides, namely haloalkanes, haloalkenes, and haloalkynes. Some of the unsaturated aliphatic and ali-cyclic HHCs are used (Table 2) as industrial solvents, others as chemical intermediates (vinyl chloride, phosgene, hexachlorocyclopentadiene, chlorohydrins, etc.) in the synthesis of other economical compounds. Still others are used in the manufacture of various important HHCs, such as chlorinated paraffins (C10 to C30 chain length), chlorofluorocarbons (banned), hexachlorobutadiene, halothane anesthetics, insecticidal aliphatic and alicyclic cyclodienes, Toxaphene, mirex, kepone, hexachlorocyclohexanes, chlorinated pyrethroids, and Chlorpyriphos.

Various HHCs, especially saturated ones, are used as intermediates for nonhalogenated products (polyur-ethanes, polycarbonates), epichlorohydrin in resins, chlorohydrin for synthesis of propylene oxide, and for specialty chemicals, such as Grignard's reagent, Freidel-Crafts reaction. Phosgene (COCl) is extensively used on-site - 80% in producing isocyanates and di-isocyanates for synthesis of polyurethane (>2 million metric tons yr-1 globally), 10% in polycarbonate plastics (0.2 million metric tons yr_1 globally). The remaining phosgene is used in other chemicals, such as herbicides, pharmaceuticals, specialty chemicals, etc. Vinyl chloride (about 12 million tons used annually in USA) is used in PVC, the most abundantly used polymer. Other products include polyvinylidene chloride and chlorobutyl rubber. Saturated HHCs are used in metal-cleaning, fire-extinguishing compounds, rubber, plastic, paint and varnish, healthcare, textile, etc., as well as in agriculture (soil fungicides, insecticides).

Perfluoroacetic acids (PFAs), perfluorooctanoic acid, and perchlorooctone sulfonate have broad-spectrum industrial and consumer applications in surfactants, coatings (fabrics, upholstery, carpets, paper products), firefighting foam, and pesticides.

Table 1 Some abundantly used HHCs and their ecosystem health and concerns

Name

Uses

Effect(s)/system(s)

Human exposure

Aliphatic HHCs Acetyl chloride Bis(2-chloroisopropyl) ether Bis(chloromethyl) ether

Bromodichloromethane Bromoform

Carbon tetrachloride

Chlorinated paraffins

2-Chloro-1,3-butadiene Chloroform

Chloromethyl methyl ether

3-Chloro-2-methyl-1-propane (and allyl bromide, tetrachloroethylene) 2,3'-Dichloro-1,4-dioxane 1,1-Dichloroethane

Dichloroethyl ether Dimethyl carbamoyl chloride Ethylene dichloride Hexachloro-1,3-butadiene

Hexachloroethane

Methyl bromide Methyl chloride

Methylene chloride

1.1.1-Trichloroethane

1.1.2-Trichloroethane Trichloroethylene

In pharmaceutical and pesticide manufacture Solvents

In industry and in laboratory, an alkylating agent in the manufacture of polymers. As solvent of polymerization reactions, in the preparation of ion-exchange resin. Intermediate for organic synthesis

As a solvent, flame retardant, floating agent, rubber vulcanizing, mineral separation, chemical synthesis Specialty process solvent, in semiconductors, metal recovery, cables, as a catalyst, azeotropic drying agent for wet spark plugs, soap fragrance, extracting oils

As plasticizers in plastics, in paints, as metal lubricant, in adhesives, as fire retardants Manufacture of artificial rubber In synthesis of fluorochemicals and fluoro polymers, in dry cleaning, as a rubber solvent

In the chemical industry for synthesis of organic chemicals Insecticidal fumigants

Solvent, paints and varnish remover, in rubber cement, insecticide sprays, fire extinguishers, gasoline, high-vacuum rubber, ore-flotation, plastic and fabric spreading, produces vinyl chloride on thermal cracking

Paints, varnish and finishing remover Solvent, intermediate in lubricants and rubber, fumigant

Degreasing metals, in pyrotechnics, explosive and military

In degreasing wool, sterilizing food, extracting oils An intermediate in HHCs, in silicone industry, as a methylating agent, solvent and diluent for butyl rubber, foaming agent for plastics, in thermo-equipment fluids As a solvent, in paint stripping, extracting coffee and other chemicals from natural food, in manufacture of plastics, pharmaceuticals, in cleaning of metals, degreasing, in aerosols, adhesives Restricted production and use, major industrial solvent, cleaning plastic mold, cold metal cleaning, coolant, lubricant for cutting oils, solvent for dyes, cleaning agent, in textile spotting fluid

In degreasing and dry cleaning, solvent, paint thinner, extracting caffeine, dental anesthetic, insecticide (fumigant)

Occupational Occupational

Rat/mouse, NMC, causes tumors in liver

Rat/mouse liver, NMC, causes tumors, SC, HW, PTP SHC, HW, PTP

CP, HW, PTP, causes tumors in liver

70 000 workers exposed

ACP, HW, PTP, causes tumors in liver CP, HS, HW, PTP, mouse liver, NMC, causes tumors in liver

Table 1 (Continued)

Name

Uses

Effect(s)/system(s)

Human exposure

1 ',1,2'2-Tetrachloroethane

CP, HW, PTP

Tetrachloroethylene

A solvent in cleaning cloths and metals, for degreasing

CP, HW, PTP, causes

tumors in liver

Vinyl cyclohexene dioxide

AC

Vinylidene chloride

C, HS, HW, PTP

Vinyl chloride

Synthesis of PVC

HC, HW, PTP

Aromatic HHCs

Benzoyl chloride

Textile and dye industries as a fastness compound

Benzyl chloride

Intermediate in benzoil compounds (benzal chloride,

AC, HS, HW

benzyl alcohol, and benzaldehyde), manufacture of

quaternary ammonium chloride, plastics, dyes,

synthetic tannins, pharmaceuticals, perfumes, and

resins

CCIU

C, HS, HW, PTP

Chlorambem

Formulation or application of this pre-emergence

CP

Workers

herbicide

involved in the

manufacture

Chlorambucil

Drug against cancer

HC, AC, HS

Chlorobenzenes

In synthesis of chloroanilide herbicides, bacteriocides

Chloronaphthalenes

Heat transformer media, solvents, lubricant, dielectric

fluid, electric insulation

Chloroprene

In the production of artificial rubber

C

2500 workers

Dichlorobenzene

Intermediate in polyphenylene insecticide for termites

(fumigant), disinfectant

Epichlorohydrin

APC, HS, HW

Hexachlorobenzene

Fungicide, intermediate for dye and

C

hexafluorobenzene, synthetic rubber, plasticizer in

PVC, military pyrotechnic, electrodes

Hexachlorophene

Topical anti-infective agent, detergent, antibacterial

soaps, surgical scrubs, hospital equipment,

fungicide

Lindane

C(N,P), HS, HW, PTP,

mouse liver, NMC

Monochlorobenzene

In synthesis of nitrochlorobenzene as a dye

intermediate, solvent

O-Nitrochlorobenzene

APC

P-Nitrochlorobenzene

PCBs (polychlorinated

AC, HS, HW, PTP, rat/

biphenyls)

mouse liver, NMC

P-Chlorobenzyl chloride

C, HS

Pentachloronitrobenzene

APC, HW

Picloram

CP

TCDD

AC, HW, PTP, rat liver,

lungs, NMC

Trichlorobenzene

Heat transformer media, transformer fluid, and solvent

Pesticides

Aldrin

Pesticide manufacture, formulator and applicators

C, HS, HW, PTP

In air, water, and

food

Allyl chloride

In the manufacture of epichlorophydrin and glycerol

HS

5000 workers

Chlordecone

Processing or formulating pesticides, control

C, HS, HW

600 workers

rootborers on bananas, wireworm control in tobacco

and ants

Chlorobenzilate

Rat liver, NMC

p-Chlorobenzotrichloride

Pesticide manufacture

AC

Chlorodane

Broad-spectrum insecticide for homes, gardens, and

CP, HS, HW

soil insects

Chloronaphazine

Treatment of leukemia and related cancer

HC, HS

DDT

ASC, HS, HW, PTP

DDVP

C, HS, HW, PTP

Human

Name Uses Effect(s)/system(s) exposure

Table 1 (Continued)

Human

Name Uses Effect(s)/system(s) exposure

1,2-Dibromo-

Stomach, mammary

3-chloropropane

gland

1,2-Dibromoethane

Subcutaneous,

stomach, blood

vessels, lungs

3,3'-Dichlorobenzidine and

AC, HW, PTP

salts

P, P'-Dichlorodiphenyl

1,2-Dichloroethane

Subcutaneous,

stomach, blood

vessels, mammary

gland

Dichloroethylene

Mouse liver, NMC

Dieldrin

Mouse liver, NMC

HCB

C, HW, PTP

HHC

C, HW, PTP

(hexachlorocyclohexane)

Heptachlore

C, HS, HW, PTP

4,4'-Methylene-

C, HW

bis(2-chloroaniline)

Mirex

C, HS, HW

Phenazopyridine

C

hydrochloride

2,4,5-T

C, HS, HW

TDE

C, HW, PTP

Toxaphene

C, HS, HW, PTP

Trichlorophenyl

SC, HW, HS, PTP

C, human carcinogen; AC, animal carcinogen; SC, suspected human carcinogen, PTP, USEPA's toxicity priority pollutant; HW, hazardous waste (USEPA).

C, human carcinogen; AC, animal carcinogen; SC, suspected human carcinogen, PTP, USEPA's toxicity priority pollutant; HW, hazardous waste (USEPA).

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