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헥사클로로벤젠

헥사클로로벤젠
헥사클로로벤젠 구조식 이미지
카스 번호:
118-74-1
한글명:
헥사클로로벤젠
동의어(한글):
헥사클로로벤젠;벤젠, 1,2,3,4,5,6-헥사클로로-;벤젠, 헥사클로로-;벤젠헥사클로라이드;퍼클로로벤젠;펜타클로로페닐 클로라이드
상품명:
HEXACHLOROBENZENE
동의어(영문):
HCB;granox;hexacb;Amatin;HCB(R);NO BUNT;Sanocid;Smut-Go;granoxnm;hexac.b.
CBNumber:
CB4149734
분자식:
C6Cl6
포뮬러 무게:
284.78
MOL 파일:
118-74-1.mol

헥사클로로벤젠 속성

녹는점
227-229 °C(lit.)
끓는 점
323-326 °C(lit.)
밀도
1.5691
증기압
1.45 x l0-3 Pa (20 °C)
굴절률
1.5691 (estimate)
인화점
11 °C
저장 조건
APPROX 4°C
물리적 상태
neat
수용성
Practically insoluble in water
Merck
13,4696
BRN
1912585
Henry's Law Constant
6.11 at 25 °C (continuous flow sparger, Sproule et al., 1991)
노출 한도
No exposure limit has been set for this com pound. Carcinogenicity: Animal Sufficient Evidence, Human Limited Evidence (IARC).
안정성
Stable. Incompatible with strong oxidizing agents.
InChIKey
CKAPSXZOOQJIBF-UHFFFAOYSA-N
CAS 데이터베이스
118-74-1(CAS DataBase Reference)
IARC
2B (Vol. Sup 7, 79) 2001
EPA
Hexachlorobenzene (118-74-1)
안전
  • 위험 및 안전 성명
  • 위험 및 사전주의 사항 (GHS)
위험품 표기 T,N,Xn,F,Xi
위험 카페고리 넘버 45-48/25-50/53-67-65-62-51/53-48/20-38-11-39/23/24/25-23/24/25-66-36/38-36
안전지침서 53-45-60-61-62-36/37-33-29-16-9-26
유엔번호(UN No.) UN 2729 6.1/PG 3
WGK 독일 3
RTECS 번호 DA2975000
위험 등급 6.1(b)
포장분류 III
유해 물질 데이터 118-74-1(Hazardous Substances Data)
독성 LC50 for ?ve freshwater species 0.05-0.2 mg/L (Hartley and Kidd, 1987); acute oral LD50 for rats 10,000 mg/kg (RTECS, 1985).
중점관리물질 필터링 별표2-36
그림문자(GHS):
신호 어: Danger
유해·위험 문구:
암호 유해·위험 문구 위험 등급 범주 신호 어 그림 문자 P- 코드
H225 고인화성 액체 및 증기 인화성 액체 구분 2 위험 P210,P233, P240, P241, P242, P243,P280, P303+ P361+P353, P370+P378,P403+P235, P501
H319 눈에 심한 자극을 일으킴 심한 눈 손상 또는 자극성 물질 구분 2A 경고 P264, P280, P305+P351+P338,P337+P313P
H336 졸음 또는 현기증을 일으킬 수 있음 특정표적장기 독성 물질(1회 노출);마취작용 구분 3 경고 P261, P271, P304+P340, P312,P403+P233, P405, P501
H350 암을 일으킬 수 있음 (노출되어도 암을 일으키지 않는다는 결정적인 증거가 있는 노출경로가 있다면 노출경로 기재) 발암성 물질 구분 1A, 1B 위험
H372 장기간 또는 반복 노출되면 장기(또는, 영향을 받은 알려진 모든 장기를 명시)에 손상을 일으킴 특정 표적장기 독성 - 반복 노출 구분 1 위험 P260, P264, P270, P314, P501
H410 장기적 영향에 의해 수생생물에 매우 유독함 수생 환경유해성 물질 - 만성 구분 1 경고 P273, P391, P501
H411 장기적 영향에 의해 수생생물에 유독함 수생 환경유해성 물질 - 만성 구분 2
예방조치문구:
P201 사용 전 취급 설명서를 확보하시오.
P210 열·스파크·화염·고열로부터 멀리하시오 - 금연 하시오.
P273 환경으로 배출하지 마시오.
P280 보호장갑/보호의/보안경/안면보호구를 착용하시오.
P308+P313 노출 또는 접촉이 우려되면 의학적인 조치· 조언를 구하시오.
P501 ...에 내용물 / 용기를 폐기 하시오.

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

white powder

화학적 성질

Hexachlorobenzene is a solid, crystallizing in nee dles.

용도

Seed fungicide

용도

In organic syntheses. Formerly as agricultural fungicide.

용도

Hexachlorobenzene is used as a fungicideand as an intermediate in organic synthesis.

용도

No commercial uses of hexachlorobenzene as an end product in the United States were identified (ATSDR 2002). Previously, it was used as a seed-treatment fungicide for onions, sorghum, wheat, and other grains (IARC 1979). All registered pesticide uses in the United States were voluntarily cancelled in 1984 (ATSDR 2002). Hexachlorobenzene was also used as a chemical intermediate in dye manufacturing, in the synthesis of other organic chemicals, and in the production of pyrotechnic compositions for the military. It was used as a raw material for synthetic rubber, as a plasticizer for polyvinyl chloride, as a porosity controller in the manufacture of electrodes, and as a wood preservative (IARC 1979, ATSDR 2002).

정의

ChEBI: A member of the class of chlorobenzenes that is benzene in which all of the hydrogens are replaced by chlorines. An agricultural fungicide introduced in the mid-1940s and formerly used as a seed treatment, its use has been banned since 1984 under the Stock olm Convention on Persistent Organic Pollutants.

정의

hexachlorobenzene: A colourlesscrystalline compound, C6Cl6; 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.

Synthesis Reference(s)

Journal of the American Chemical Society, 69, p. 3146, 1947 DOI: 10.1021/ja01204a507

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

Harmful by dust inhalation or if swallowed. Irritating to eyes, skin and mucous membranes. Prolonged periods of ingestion may cause cutaneous porphyria.

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/m3 (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.

Source

Hexachlorobenzene may enter the environment from incomplete combustion of chlorinated compounds including mirex, kepone, chlorobenzenes, pentachlorophenol, PVC, polychlorinated biphenyls, and chlorinated solvents (Ahling et al., 1978; Dellinger et al., 1991). In addition, hexachlorobenzene may enter the environment as a reaction by-product in the production of carbon tetrachloride, dichloroethylene, hexachlorobutadiene, trichloroethylene, tetrachloroethylene, pentachloronitrobenzene, and vinyl chloride monomer (quoted, Verschueren, 1983).

환경귀착

Biological. Reductive monodechlorination occurred in an anaerobic sewage sludge yielding principally 1,3,5-trichlorobenzene. Other compounds identified included pentachlorobenzene, 1,2,3,5-tetrachlorobenzene and dichlorobenzenes (Fathepure et al., 1988). In activated sludge, only 1.5% of the applied hexachlorobenzene mineralized to carbon dioxide after 5 days (Freitag et al., 1985). In a 5-day experiment, 14C-labeled hexachlorobenzene applied to soil-water suspensions under aerobic and anaerobic conditions gave 14CO2 yields of 0.4 and 0.2%, respectively (Scheunert et al., 1987).
When hexachlorobenzene was statically incubated in the dark at 25°C with yeast extract and settled domestic wastewater inoculum, no signi?cant biodegradation was observed. At a concentration of 5 mg/L, percent losses after 7, 14, 21 and 28-day incubation
Groundwater. According to the U.S. EPA (1986) hexachlorobenzene has a high potential to leach to groundwater.
Photolytic. Solid hexachlorobenzene exposed to arti?cial sunlight for 5 months photolyzed at a very slow rate with no decomposition products identified (Plimmer and Klingebiel, 1976). The sunlight irradiation of hexachlorobenzene (20 g) in a 100 mL borosilicate glass-stoppered Erlenmeyer ?ask for 56 days yielded 64 ppm pentachlorobiphenyl (Uyeta et al., 1976). A carbon dioxide yield <0.1% was observed when hexachlorobenzene adsorbed on silica gel was irradiated with light (λ >290 nm) for 17 hours (Freitag et al., 1985).
Irradiation (λ ≥285 nm) of hexachlorobenzene (1.1–1.2 mM/L) in an acetonitrile-water mixture containing acetone (concentration = 0.553 mM/L) as a sensitizer gave the following products (% yield): pentachlorobenzene (71.0), 1,2,3,4-tetrachlorobenzene (0.6)

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.

Solubility in organics

In millimole fraction at 25 °C: 2.62 in n-hexane, 3.14 in n-heptane, 3.71 in n-octane, 4.10 in nnonane, 4.60 in n-decane, 6.81 in n-hexadecane, 2.95 in cyclohexane, 3.87 in methylcyclohexane, 2.52 in 2,2,4-trimethylpentane, 4.71 in tert-butylcyclohexane, 4.40 in dibutyl ether, 3.20 in methyl tert-butyl ether, 5.92 in tetrahydrofuran, 3.97 in 1,4-dioxane, 0.0902 in methanol, 0.236 in ethanol, 0.398 in 1-propanol, 0.298 in 2-propanol, 0.667 in 1-butanol, 0.521 in 2- butanol, 0.533 in 2-methyl-1-propanol, 0.517 in 2-methyl-2-propanol, 1.03 in 1-pentanol, 0.860 in 2-propanol, 0.770 in 3-methyl-1-butanol, 1.20 on 2-methyl-2-butanol, 1.44 in 1-hexanol, 1.40 in 2-methyl-1-pentanol, 1.43 in 4-methyl-2-pentanol, 1.90 in 1-heptanol, 2.38 in 1-octanol, 1.74 in 2-ethyl-1-hexanol, 3.80 in 1-decanol, 0.920 in cyclopentanol, 3.65 in butyl acetate, 2.11 in ethyl acetate, 1.48 in methyl acetate, 2.86 in 1,2-dichloroethane, 3.83 in 1-chlorobutane, 5.08 in 1-chlorohexane, 6.06 in 1-chlorooctane, 6.10 in chlorocyclohexane (De Fina et al., 2000)

Solubility in water

In millimole fraction at 25 °C: 2.62 in n-hexane, 3.14 in n-heptane, 3.71 in n-octane, 4.10 in nnonane, 4.60 in n-decane, 6.81 in n-hexadecane, 2.95 in cyclohexane, 3.87 in methylcyclohexane, 2.52 in 2,2,4-trimethylpentane, 4.71 in tert-butylcyclohexane, 4.40 in dibutyl ether, 3.20 in methyl tert-butyl ether, 5.92 in tetrahydrofuran, 3.97 in 1,4-dioxane, 0.0902 in methanol, 0.236 in ethanol, 0.398 in 1-propanol, 0.298 in 2-propanol, 0.667 in 1-butanol, 0.521 in 2- butanol, 0.533 in 2-methyl-1-propanol, 0.517 in 2-methyl-2-propanol, 1.03 in 1-pentanol, 0.860 in 2-propanol, 0.770 in 3-methyl-1-butanol, 1.20 on 2-methyl-2-butanol, 1.44 in 1-hexanol, 1.40 in 2-methyl-1-pentanol, 1.43 in 4-methyl-2-pentanol, 1.90 in 1-heptanol, 2.38 in 1-octanol, 1.74 in 2-ethyl-1-hexanol, 3.80 in 1-decanol, 0.920 in cyclopentanol, 3.65 in butyl acetate, 2.11 in ethyl acetate, 1.48 in methyl acetate, 2.86 in 1,2-dichloroethane, 3.83 in 1-chlorobutane, 5.08 in 1-chlorohexane, 6.06 in 1-chlorooctane, 6.10 in chlorocyclohexane (De Fina et al., 2000)

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.]

Degradation

Hexachlorobenzene is very stable and is unreactive toward acids and bases.
Photolysis is very slow and in artificial sunlight, solid HCB photodecomposed after 5 months. In sunlight, 20 g of HCB contained in a borosilicate flask gave a concentration of 64 mg kg-1 of pentachlorobiphenyl after 56 days (Uyeta et al., 1976).
Sensitised photolysis of HCB in an acetonitrile/water mixture containing acetone at wavelengths greater than 285 nm gave the following products: pentachlorobenzene (2) (71%), 1,2,3,4-tetrachlorobenzene (3) (0.6%), 1,2,3,5-tetrachlorobenzene (4) (2.2%) and 1,2,4,5-tetrachlorobenzene (5) (3.7%). In the absence of acetone, products identified included 2 (76.8%), 4 (1.2%), 5 (1.7%) and 1,2,4-trichlorobenzene (6) (0.2%) (Choudhry and Hutzinger, 1984) (see Scheme 1).

Toxicity evaluation

There are no reports of avian casualties, although raptors found dead in The Netherlands had substantial levels of HCB in their livers along with cyclodiene and DDE residues (33). The same authors reported porphyria in quail following a 3-month dosing period with 20-ppm HCB. Product registrations in Canada at the time allowed up to 1000 ppm on various cereal seeds. In the early 1970s, levels in the range of 3–4 ppm (fresh weight basis) were seen in eggs of fish-eating birds of the Great Lakes and likely contributed to the high levels of embryonic mortality seen (34). However, because HCB is also an intermediate in the manufacture of several chemicals, industrial pollution rather than use of the chemical on farm fields could have been the source of the contamination.

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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