헥사클로로벤젠 C화학적 특성, 용도, 생산
개요
Hexachlorobenzene is a white crystalline solid. This compound does not occur naturally.
It is formed as a by-product during the manufacture of chemicals used as solvents
(substances used to dissolve other substances), other chlorine-containing compounds,
and pesticides. Small amounts of hexachlorobenzene can also be produced during combustion
processes such as burning of city wastes. It may also be produced as a by-product
in waste streams of chlor-alkali and wood-preserving plants. Hexachlorobenzene
was widely used as a pesticide until 1965. It was also used to make fireworks, ammunition,
and synthetic rubber.
화학적 성질
Hexachlorobenzene is a solid, crystallizing in nee dles.
용도
Hexachlorobenzene is used as a fungicideand as an intermediate in organic synthesis.
정의
hexachlorobenzene: A colourlesscrystalline compound, C
6Cl
6; m.p.227°C. It is made by the chlorinationof benzene with an iron(III) chloridecatalyst or by treating hexachlorocyclohexanewith chlorine in hexachloroethane.It is used to preservewood and dress seeds, and in themanufacture of hexafluorobenzene.
일반 설명
A white crystalline substance. Insoluble in water and denser than water. Contact may irritate skin, eyes and mucous membranes. May be toxic by ingestion. Used to make other chemicals.
공기와 물의 반응
HEXACHLOROBENZENE is sensitive to moisture. Insoluble in water.
반응 프로필
HEXACHLOROBENZENE reacts violently with dimethylformamide. .
위험도
Possible carcinogen. Toxic by ingestion.
Combustible.
건강위험
The acute oral and inhalation toxicity ofhexachlorobenzene is low in test animals.Repeated ingestion of this compound mayproduce porphyria hepatica (increased for mation and excretion of porphyrin) causedby disturbances in liver metabolism. The oralLD50 value in rabbits is 2600 mg/kg; theinhalation LC50 value from a single exposureis 1800 mg/m
3 (NIOSH 1986). The occupa tional health hazard from inhalation shouldbe very low because of its very low vaporpressure (0.00001 torr).
Hexachlorobenzene causes cancer in ani mals. Oral administration of this compoundfor 18 weeks to 2 years caused tumors inthe liver, kidney, thyroid, and blood in rats,mice, and hamsters. It is a suspected humancarcinogen, evidence of which occurs to alimited extent.
화재위험
Noncombustible solid; very low reactiv ity. Reaction with dimethyl formamide is
reported to be violent at temperatures above
65°C (149°F) (NFPA 1997).
잠재적 노출
Hexachlorobenzene was used as a fun gicide; an additive for pyrotechnic compositions; and as
wood preservative. It was used widely as a pesticide to pro tect seeds of onions and sorghum, wheat, and other grains
against fungus until 1965. This material was used to make
fireworks; ammunition for military uses; synthetic rubber;
as a porosity controller in the manufacture of electrodes; as
an intermediate in dye manufacture; in organic synthesis. It
is formed as a by-product of making other chemicals; in
the waste streams of chloralkali and wood-preserving
plants; and when burning municipal waste. Currently, there
are no commercial uses of hexachlorobenzene in the United
States.
Carcinogenicity
Hexachlorobenzene is reasonably anticipated to be a human carcinogen based on sufficient evidence of carcinogenicity from studies in experimental animals.
신진 대사 경로
With the incubation of rat liver microsomes,
hexachlorobenzene is metabolized to give
pentachlorophenol and tetrachlorohydroquinone, and,
in addition, a considerable amount of covalent binding
to protein is detected (250 pM pentachlorophenol,
17 pM tetrachlorohydroquinone, and 11 pM
tetrachlorobenzoquinone covalent binding in an
incubation containing 50 μM hexachlorobenzene).
신진 대사
Sensitized photolysis of HCB at wavelengths greater
than 285 nm in acetonitrile/water containing acetone gave
dechlorinated products: pentachlorobenzene (78) (71%),
1,2,3,4-tetrachlorobenzene (79) (0.6%), 1,2,3,5-tetrachlorobenzene
(80) (2.2%), and 1,2,4,5- tetrachlorobenzene
(81) (3.7%). Without acetone, products included
pentachlorobenzene (78) (76.8%), 1,2,3,5-tetrachlorobenzene
(80) (1.2%), 1,2,4,5- tetrachlorobenzene (81) (1.7%),
and 1,2,4-trichlorobenzene (82) (0.2%) (105).
Irradiation of hexachlorobenzene in methanol solution
at wavelengths greater than 260 nm gave a
mixture of reductively dechlorinated products (pentachlorobenzene
and a tetrachlorobenzene, probably 80)
and pentachlorobenzyl alcohol 83, and also a tetrachlorodi(
hydroxymethyl)benzene (106). A similar product
mixture was obtained by exposing a methanolic solution of
hexachlorobenzene inmethanol to sunlight outdoors. After
15 days, only 30% of hexachlorobenzene was recovered.
Photolysis rates were enhanced by the addition of sensitizers
(diphenylamine, tryptophane, and naturally occurring
organic substances), but no products were identified.
In an anaerobic sewage sludge, hexachlorobenzene was
reductively dechlorinated and the principal product was
1,3,5-trichlorobenzene (84). Pentachlorobenzene, 1,2,3,5-
tetrachlorobenzene, and dichlorobenzenes were also identified
(107). In activated sludge, 1.5% of hexachlorobenzene
was mineralized as carbon dioxide after 5 days.
운송 방법
UN2729 Hexachlorobenzene, Hazard Class: 6.1;
Labels: 6.1-Poisonous materials.
Purification Methods
Crystallise hexachlorobenzene repeatedly from *benzene. Dry it under vacuum over P2O5. [Beilstein 5 H 205, 5 IV 670.]
비 호환성
Reacts violently with oxidizers; dimethyl
formamide above 65 ℃.
폐기물 처리
Incineration is most effective
@ 1300 ℃ and 0.25 seconds. Consult with environmental
regulatory agencies for guidance on acceptable disposal
practices. Generators of waste containing this contaminant
(≥100 kg/mo) must conform to EPA regulations governing
storage, transportation, treatment, and waste disposal.
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