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클로로벤젠

클로로벤젠
클로로벤젠 구조식 이미지
카스 번호:
108-90-7
한글명:
클로로벤젠
동의어(한글):
클로로벤젠;모노클로로벤졸;벤젠,클로로;테트로신SP;모노클로로벤젠;벤젠염화물;페닐염화물;벤젠 염화물;벤젠, 클로로;테트로신 SP;페닐 염화물
상품명:
Chlorobenzene
동의어(영문):
cp27;NSC 8433;U.N. 1134;orobenzene;NCI-C54886;tetrosinsp;Abluton T30;Chlorbenzen;Chlorbenzol;Chlorbenzene
CBNumber:
CB7249002
분자식:
C6H5Cl
포뮬러 무게:
112.56
MOL 파일:
108-90-7.mol

클로로벤젠 속성

녹는점
-45 °C (lit.)
끓는 점
132 °C (lit.)
밀도
1.106 g/mL at 25 °C (lit.)
증기 밀도
3.86 (vs air)
증기압
11.8 mm Hg ( 25 °C)
굴절률
n20/D 1.524(lit.)
인화점
75 °F
저장 조건
2-8°C
용해도
water: soluble0.207 g/L at 20°C
물리적 상태
Liquid
색상
APHA: ≤30
상대극성
0.188
냄새
Almond like odour
폭발한계
1.3-11%(V)
수용성
0.4 g/L (20 ºC)
어는점
-45.6℃
최대 파장(λmax)
λ: 288 nm Amax: 1.0
λ: 290 nm Amax: 0.40
λ: 300 nm Amax: 0.05
λ: 325 nm Amax: 0.04
λ: 360-400 nm Amax: 0.01
Merck
14,2121
BRN
605632
Henry's Law Constant
1.11, 1.54, 1.81, 2.80, and 3.79 at 2.0, 6.0, 10.0, 18.0, and 25.0 °C, respectively (EPICS-SPME, Dewulf et al., 1999)(x 10-3 atm?m3/mol)
노출 한도
TLV-TWA 75 ppm (~345 mg/m3) (ACGIH, MSHA, OSHA, and NIOSH); IDLH 2400 ppm.
안정성
Stable. Incompatible with oxidizing agents. Flammable. Attacks some types of plastics, rubber and coatings.
CAS 데이터베이스
108-90-7(CAS DataBase Reference)
NIST
Benzene, chloro-(108-90-7)
EPA
Chlorobenzene (108-90-7)
안전
  • 위험 및 안전 성명
  • 위험 및 사전주의 사항 (GHS)
위험품 표기 Xn,N,T,F
위험 카페고리 넘버 10-20-51/53-40-39/23/24/25-23/24/25-11
안전지침서 24/25-61-36/37-45-16-7
유엔번호(UN No.) UN 1134 3/PG 3
WGK 독일 2
RTECS 번호 CZ0175000
F 고인화성물질 3-10
자연 발화 온도 590 °C
TSCA Yes
위험 등급 3
포장분류 III
HS 번호 29039190
유해 물질 데이터 108-90-7(Hazardous Substances Data)
독성 LD50 orally in Rabbit: 2000 - 4000 mg/kg
기존화학 물질 KE-25489
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
H226 인화성 액체 및 증기 인화성 액체 구분 3 경고
H301 삼키면 유독함 급성 독성 물질 - 경구 구분 3 위험 P264, P270, P301+P310, P321, P330,P405, P501
H311 피부와 접촉하면 유독함 급성 독성 물질 - 경피 구분 3 위험 P280, P302+P352, P312, P322, P361,P363, P405, P501
H315 피부에 자극을 일으킴 피부부식성 또는 자극성물질 구분 2 경고 P264, P280, P302+P352, P321,P332+P313, P362
H319 눈에 심한 자극을 일으킴 심한 눈 손상 또는 자극성 물질 구분 2A 경고 P264, P280, P305+P351+P338,P337+P313P
H331 흡입하면 유독함 급성 독성 물질 흡입 구분 3 위험 P261, P271, P304+P340, P311, P321,P403+P233, P405, P501
H332 흡입하면 유해함 급성 독성 물질 흡입 구분 4 경고 P261, P271, P304+P340, P312
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
H341 유전적인 결함을 일으킬 것으로 의심됨 (노출되어도 생식세포 유전독성을 일으키지 않는다는 결정적인 증거가 있는 노출경로가 있다면 노출경로 기재) 생식세포 변이원성 물질 구분 2 경고 P201,P202, P281, P308+P313, P405,P501
H351 암을 일으킬 것으로 의심됨 (노출되어도 암을 일으키지 않는다는 결정적인 증거가 있는 노출경로가 있다면 노출경로 기재) 발암성 물질 구분 2 경고 P201, P202, P281, P308+P313, P405,P501
H370 장기(또는, 영향을 받은 알려진 모든 장기를 명시)에 손상을 일으킴(노출되어도 특정 표적장기 독성을 일으키지 않는다는 결정적인 노출경로가 있다면 노출경로를 기재) 특정 표적장기 독성 - 1회 노출 구분 1 위험 P260, P264, P270, P307+P311, P321,P405, P501
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
H373 장기간 또는 반복 노출되면 장기(또는, 영향을 받은 알려진 모든 장기를 명시)에 손상을 일으킬 수 있음 특정 표적장기 독성 - 반복 노출 구분 2 경고 P260, 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.
P202 모든 안전 조치 문구를 읽고 이해하기 전에는 취급하지 마시오.
P210 열·스파크·화염·고열로부터 멀리하시오 - 금연 하시오.
P233 용기를 단단히 밀폐하시오. 용기는 환기가 잘 되는 곳에 단단히 밀폐하여 보관하시오.
P240 용기와 수용설비를 접지 및 접합시키시오.
P260 분진·흄·가스·미스트·증기·...·스프레이를 흡입하지 마시오.
P261 분진·흄·가스·미스트·증기·...·스프레이의 흡입을 피하시오.
P264 취급 후에는 손을 철저히 씻으시오.
P264 취급 후에는 손을 철저히 씻으시오.
P270 이 제품을 사용할 때에는 먹거나, 마시거나 흡연하지 마시오.
P271 옥외 또는 환기가 잘 되는 곳에서만 취급하시오.
P273 환경으로 배출하지 마시오.
P280 보호장갑/보호의/보안경/안면보호구를 착용하시오.
P281 요구되는 개인 보호구를 착용하시오
P311 의료기관(의사)의 진찰을 받으시오.
P391 누출물을 모으시오.
P301+P310 삼켰다면 즉시 의료기관(의사)의 진찰을 받으시오.
P303+P361+P353 피부(또는 머리카락)에 묻으면 오염된 모든 의복은 벗거나 제거하시오 피부를 물로 씻으시오/샤워하시오.
P304+P340 흡입하면 신선한 공기가 있는 곳으로 옮기고 호흡하기 쉬운 자세로 안정을 취하시오.
P308+P313 노출 또는 접촉이 우려되면 의학적인 조치· 조언를 구하시오.
P370+P378 화재 시 불을 끄기 위해 (Section 5. 폭발, 화재시 대처방법의 적절한 소화제)을(를) 사용하시오.
P403+P233 용기는 환기가 잘 되는 곳에 단단히 밀폐하여 저장하시오.
NFPA 704
3
3 0

클로로벤젠 C화학적 특성, 용도, 생산

물성

클로로벤젠(chlorobenzene, 화학식: C6H5Cl) 는 벤젠의 염화물이며 페닐기 에 염소가 붙어있으므로 Ph-Cl 로 표시되기도 한다. 물에는 녹지 않고, 대부분의 유기용매와 임의의 비율로 섞인다. 철의 존재하에 벤젠을 염소화하여 얻는다.

개요

클로로벤젠은 상온에서 독특한 냄새가 나는 무색의 액체 상태를 유지하는 방향족성 화합물로,5개의 수소 원자와 6개의 탄소 원자, 그리고 1개의 염소 원자로 구성되어 있습니다.여기서 방향족성(Aromaticity) 화합물이란 탄소 화합물이 불포화 결합이나,홀전자쌍 등에 의해 평면 고리 모양으로 결합되어 매우 안정화 되어 있는 성질을 가진 화합물을 말합니다.

용도

클로로 벤젠은 특정 살충제 제조에 한번 사용되었습니다., 가장 주목할만한 것은 chloral (trichloroacetaldehyde), 그러나이 응용 프로그램은 ddt의 사용이 감소함에 따라 감소했습니다. 클로로 벤젠의 주요 용도는 제초제와 같은 필수품의 생산에서 중간체로서, 물감, 고무. 클로로 벤젠은 또한 많은 산업 분야뿐만 아니라 실험실에서도 고비 점용제로 사용됩니다. 클로로 벤젠을 대규모로 니트로 화하여 2- 및 4- 니트로 클로로 벤젠의 혼합물을 수득한다, 이는 분별 결정화 후 증류에 의해 분리 될 수있다.

독성

클로로벤젠은 공기 중에서 약 3.5일, 물 속에서 하루, 그리고 토양에서 수 개월간 존재할 수 있으며,오염된 토양과 접촉하거나, 물을 마시거나, 오염된 공기를 호흡해 노출될 수 있습니다. 일반적으로 오염된 공기를 통해 체내로 들어온 클로로벤젠은 폐와 비뇨계를 통해 배출되지만,피부에 반복적으로 노출되면 탈지 작용으로 피부염을 일으킬 수 있으며, 급성으로 노출 시 기침 같은 작은 증상만 나타나지만 만성 흡입시 폐나 간, 신장에 손상을 줄 수 있기 때문에 주의가 팔요합니다.

개요

Chlorobenzene production has been declining since its peak in 1969, and is likely to continue declining due to the substitution of more environmentally friendly chemicals. Chlorobenzene is produced by chlorination of benzene in the presence of a catalyst, and is produced as an end product in the reductive chlorination of di- and trichlorobenzenes. This compound is extensively used in the manufacture of phenol, aniline, and DDT; as a solvent for paints; and as a heat transfer medium. It is also occasionally used in the dry cleaning industry.
Chlorobenzene’s production and use as a chemical intermediate, solvent, and heat transfer medium may result in its release to the environment through various waste streams. If released to air, chlorobenzene will exist solely as a vapor in the atmosphere. Photochemically produced hydroxyl radicals will ultimately degrade vapor-phase chlorobenzene in less than 24 h. Exposure of chlorobenzene to direct sunlight (absorbs at >290 nm) will cause photolysis. Occupational exposure to chlorobenzene may occur through inhalation and dermal contact with this compound at workplaces where chlorobenzene is produced or used. Monitoring data indicate that the general population may be exposed to chlorobenzene via inhalation of ambient air, ingestion of food and drinking water, and dermal contact with this compound.

화학적 성질

colourless liquid, Chlorination of benzene in the presence of a catalyst (FeCl3 or AICI3) yields chlorobenzene as the first product. Substitution with a second CI yields ortho, para, or meta dichlorobenzene, Eventually all the hydrogens can be substituted to give hexachlorobenzene, C6C16. In the presence ofultraviolet light, the chlorinationofbenzene yields benzene hexachloride, C6H6C~, a derivative ofcyclohexane.

화학적 성질

Chlorobenzene, also called monochlorobenzene, is a monocyclic aromatic compound. It is a colorless liquid with an aromatic almond-like odor and is manufactured for use as a solvent, is used in the production of other chemicals (pesticides), and in making certain other chemicals, rubber, dyes and grease solvents. It is used as a feedstock to produce ortho- and para- nitrochlorobenzenes and aniline; as a solvent for paints; and as a heat transfer medium. In the past,Chlorobenzene was used as an intermediate in phenol and DDT production. Chlorobenzene enters the environment from industrial and municipal discharges. Another potential source is the formation and emission of Chlorobenzene as a product of incomplete combustion in waste incinerators.
Chlorobenzene is moderately soluble in water; up to 1,000 milligrams will mix with a liter of water. Chlorobenzene is slightly persistent in water, with a half-life of between 2 to 20 days. Chlorobenzene persists in soil (several months), in air (3.5 days), and water (less than 1 day).
When heated to decomposition this compound emits toxic fumes of hydrogen chloride gas, CO and CO2. Common synonyms are Monochlorobenzene, Benzene Chloride, and Chlorobenzol. It is incompatible with strong oxidizing agents and dimethyl sulfoxide.
Chlorobenzene (also best known as monochlorobenzene or MCB) is a flammable liquid. Companies also use MCB to make adhesives, paints, paint removers, polishes, dyes, and drugs. In the past companies have used MCB to make phenol and related chemicals, pesticides (like DDT), and aniline.
Chlorobenzene can evaporate when exposed to air. It dissolves slightly when mixed with water. Effects of chlorobenzene on human health and the environment depend on how much chlorobenzene is present and the length and frequency of exposure. Effects also depend on the health of a person or the condition of the environment when exposure occurs.

물리적 성질

Clear, colorless, flammable liquid with a sweet almond, medicinal or mothball-like odor. An odor threshold concentration of 210 ppbv was reported by Leonardos et al. (1969). At 40 °C, the lowest concentration at which an odor was detected was 190 μg/L. At 25 °C, the lowest concentration at which a taste was detected was 190 μg/L (Young et al., 1996). The average least detectable odor threshold concentration in water at 60 °C was 0.08 mg/L (Alexander et al., 1982). Cometto-Mu?iz and Cain (1994) reported an average nasal pungency threshold concentration of 10,553 ppmv.

용도

Monochlorobenzene is used commercially as a solvent and to produce phenol and nitrochlorobenzenes.

용도

Chlorobenzene is used as a solvent for paints,as a heat transfer medium, and in the manu facture of phenol and aniline.

용도

Chlorobenzene is a halogenated benzene used in chemical toxicity QSAR research for agricultural pollution.

정의

ChEBI: The simplest member of the class of monochlorobenzenes, that is benzene in which a single hydrogen has been substituted by a chlorine.

정의

A colorless liquid made by the catalytic reaction of chlorine with benzene. It can be converted to phenol by reaction with sodium hydroxide under extreme conditions (300°C and 200 atmospheres pressure). It is also used in the manufacture of other organic compounds.

Synthesis Reference(s)

Journal of the American Chemical Society, 74, p. 6297, 1952 DOI: 10.1021/ja01144a523
Tetrahedron Letters, 23, p. 371, 1982 DOI: 10.1016/S0040-4039(00)86833-1

일반 설명

A colorless to clear, yellowish liquid with a sweet almond-like odor. Flash point 84°F. Practically insoluble in water and somewhat denser than water (9.2 lb / gal). Vapors heavier than air. Used to make pesticides, dyes, and other chemicals.

공기와 물의 반응

Highly flammable. Insoluble in water.

반응 프로필

Chlorobenzene undergoes a sometimes explosive reaction with powdered sodium or phosphorus trichloride + sodium. May react violently with dimethyl sulfoxide. Reacts vigorously with oxidizing agents. Attacks some forms of plastic, rubber and coatings. Forms a shock sensitive solvated salt with silver perchlorate. .

위험도

A possible carcinogen. Avoid inhalation and skin contact. Moderate fire risk. Explosive limits 1.8–9.6%.

건강위험

Irritating to skin, eyes and mucous membranes. Repeated exposure of skin may cause dermatitis due to defatting action. Chronic inhalation of vapors or mist may result in damage to lungs, liver, and kidneys. Acute vapor exposures can cause symptoms ranging from coughing to transient anesthesia and central nervous system depression.
Limited information is available on the acute (short-term) effects of chlorobenzene. Acute inhalation exposure of animals to chlorobenzene produced narcosis, restlessness, tremors, and muscle spasms. Chronic (long-term) exposure of humans to chlorobenzene affects the central nervous system (CNS). Signs of neurotoxicity in humans include numbness, cyanosis, hyperesthesia (increased sensation), and muscle spasms. No information is available on the carcinogenic effects of chlorobenzene in humans. EPA has classified chlorobenzene as a Group D, not classifiable as to human carcinogenicity.

화재위험

Flammable liquid; flash point (closed cup) 29°C (84°F); vapor pressure 8.8 torr at 20°C (68°F); autoignition temperature 638°C (1180°F).
Chlorobenzene vapors form explosive mixtures with air within the range 1.3-7.1% by volume in air. Dimethyl sulfoxide decom poses violently in contact with chloroben zene (NFPA 1997). Many metal perchlorates, such as those of silver and mercury, may form shock-sensitive solvated perchlorates that may explode on impact.

Safety Profile

Suspected carcinogen. Moderately toxic by ingestion and intraperitoneal routes. Experimental teratogenic and reproductive effects. Mutation data reported. Strong narcotic with slight irritant qualities. Dichlorobenzols are strongly narcotic. Little is known of the effects of repeated exposures at lower concentrations, but it may cause hdney and liver damage. The industrial illnesses reported may possibly be due to nitrobenzol. Dangerous fire hazard when exposed to heat or flame. Moderate explosion hazard when exposed to heat or flame. Potentially explosive reaction with powdered sodium or phosphorus trichloride + sodtum. Violent reaction with AgClO4. Reacts vigorously with oxidizers. See also CHLORINATED HYDROCARBONS, AROMATIC. To fight fire, use foam, CO2, dry chemical, water to blanket fire. Associated with EPA Superfund sites

잠재적 노출

Chlorobenzene is used in the manufacture of aniline, phenol, and chloronitrobenzene; as an intermediate in the manufacture of dyestuffs and many pesticides, as a solvent; and emulsifier.

Carcinogenicity

Chlorobenzene was not mutagenic in a variety of bacterial and yeast assays. Existing data suggest that genotoxicity may not be an area of concern for chlorobenzene exposure in humans.

환경귀착

Biological. In activated sludge, 31.5% of the applied chlorobenzene mineralized to carbon dioxide after 5 d (Freitag et al., 1985). A mixed culture of soil bacteria or a Pseudomonas sp. transformed chlorobenzene to chlorophenol (Ballschiter and Scholz, 1980). Pure microbial cultures isolated from soil hydroxylated chlorobenzene to 2- and 4-chlorophenol (Smith and Rosazza, 1974). Chlorobenzene was statically incubated in the dark at 25 °C with yeast extract and settled domestic wastewater inoculum. At a concentration of 5 mg/L, biodegradation yields at the end of 1 and 2 wk were 89 and 100%, respectively. At a concentration of 10 mg/L, significant degradation with gradual adaptation was observed.Complete degradation was not observed until after the 3rd week of incubation (Tabak et al.,1981).
https://www.epa.gov

운송 방법

UN1134 Chlorobenzene, Hazard Class: 3; Labels: 3-Flammable liquid.

Purification Methods

The main impurities are likely to be chlorinated impurities originally present in the *benzene used in the synthesis of chlorobenzene, and also unchlorinated hydrocarbons. A common purification procedure is to wash it several times with conc H2SO4 then with aqueous NaHCO3 or Na2CO3, and water, followed by drying with CaCl2, K2CO3 or CaSO4, then with P2O5, and distilling. It can also be dried with Linde 4A molecular sieve. Passage through, and storage over, activated alumina has been used to obtain low conductance material. [Flaherty & Stern J Am Chem Soc 80 1034 1958, Beilstein 5 H 199, 5 IV 640.]

Toxicity evaluation

In the ambient atmosphere, chlorobenzene will exist as a vapor, and will be degraded by reaction with photochemically produced hydroxyl radicals, with an estimated half-life of 21 days. It can be removed from the air by rain. Photolysis halflives of 4–18 h were measured in aqueous media. If released to soil, chlorobenzene is expected to have very high to moderate mobility based on a Koc range of 4.8–313. Moist soil surfaces will favor volatilization based upon Henry’s Law constant of 3.11×103 atm-cu m mol-1. Chlorobenzene may volatilize from dry soil surfaces as well. If released into water, chlorobenzene may adsorb to suspended solids and sediment based on the Koc values. Volatilization from water surfaces is expected to be an important fate process based on this compound’s Henry’s Law constant. Estimated volatilization half-lives for a model river and model lake are 3.4 h and 4.3 days, respectively. Reported bioconcentration in aquatic organisms is low to high, provided the compound is not metabolized by the organism. Hydrolysis is not expected to be an important environmental fate process since this compound lacks functional groups that hydrolyze under environmental conditions. Biodegradation results are variable based on soil type and microbial diversity. In river water, the biodegradation half-life was reported to be 150 and 75 days in the sediment.

비 호환성

Reacts violently with strong oxidizers; dimethyl sulfoxide; sodium powder; silver perchlorate; causing fire and explosion hazard. Attacks some plastics, rubber, and coatings. Decomposes on heating, producing phosgene and hydrogen chloride fumes.

폐기물 처리

Incineration, preferably after mixing with another combustible fuel; care must be exercised to assure complete combustion to prevent the formation of phosgene; an acid scrubber is necessary to remove the halo acids produced.

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