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벤조(a)피렌

벤조(a)피렌
벤조(a)피렌 구조식 이미지
카스 번호:
50-32-8
한글명:
벤조(a)피렌
동의어(한글):
벤조(a)피렌;벤조피렌;벤조피렌
상품명:
BENZO[A]PYRENE
동의어(영문):
BP;BAP;HPA1S;3,4-BP;NSC 21914;HP2ALPHA2;Benzpyrene;BENZOPYRENE;BENZ[A]PYRENE;Benzo(a)pyren
CBNumber:
CB3696680
분자식:
C20H12
포뮬러 무게:
252.31
MOL 파일:
50-32-8.mol

벤조(a)피렌 속성

녹는점
177-180°C
끓는 점
495°C
밀도
1.1549 (estimate)
증기압
2.4 at 25 °C (McVeety and Hites, 1988)
굴절률
1.8530 (estimate)
인화점
495°C
저장 조건
APPROX 4°C
용해도
Soluble in benzene, toluene, and xylene; sparingly soluble in ethanol and methanol (Windholz et al., 1983)
산도 계수 (pKa)
>15 (Christensen et al., 1975)
물리적 상태
Crystalline
색상
Pale yellow/green/orange
수용성
Soluble in benzene, toluene, and xylene. Sparingly soluble in alcohol, methanol. Insoluble in water
Merck
14,1103
BRN
1911333
Henry's Law Constant
7.35 at 25 °C (thermodynamic method-GC/UV spectrophotometry, Altschuh et al., 1999)(x 10-10 mmHg at 25 °C):
안정성
Stable. Incompatible with strong oxidizing agents.
InChIKey
FMMWHPNWAFZXNH-UHFFFAOYSA-N
CAS 데이터베이스
50-32-8(CAS DataBase Reference)
안전
  • 위험 및 안전 성명
  • 위험 및 사전주의 사항 (GHS)
위험품 표기 T,N,F
위험 카페고리 넘버 45-46-50/53-60-61-43-67-66-36-11-65-38-52/53-36/37/38
안전지침서 45-53-61-60-26-62-16
유엔번호(UN No.) 2811
WGK 독일 3
RTECS 번호 DJ3675000
TSCA Yes
위험 등급 6.1
포장분류 III
HS 번호 29029090
독성 LD50 for mice (intraperitoneal) 232 mg/kg (Salamone, 1981).
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
H304 삼켜서 기도로 유입되면 치명적일 수 있음 흡인 유해성물질 구분 1 위험
H315 피부에 자극을 일으킴 피부부식성 또는 자극성물질 구분 2 경고 P264, P280, P302+P352, P321,P332+P313, P362
H317 알레르기성 피부 반응을 일으킬 수 있음 피부 과민성 물질 구분 1 경고 P261, P272, P280, P302+P352,P333+P313, P321, P363, 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
H340 유전적인 결함을 일으킬 수 있음 (노출되어도 생식세포 유전독성을 일으키지 않는다는 결정적인 증거가 있는 노출경로가 있다면 노출경로 기재) 생식세포 변이원성 물질 구분 1A, 1B 위험
H350 암을 일으킬 수 있음 (노출되어도 암을 일으키지 않는다는 결정적인 증거가 있는 노출경로가 있다면 노출경로 기재) 발암성 물질 구분 1A, 1B 위험
H360 태아 또는 생식능력에 손상을 일으킬 수 있음 생식독성 물질 구분 1A, 1B 위험
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
H400 수생생물에 매우 유독함 수생 환경유해성 물질 - 급성 구분 1 경고 P273, P391, P501
H410 장기적 영향에 의해 수생생물에 매우 유독함 수생 환경유해성 물질 - 만성 구분 1 경고 P273, P391, P501
H412 장기적 영향에 의해 수생생물에 유해함 수생 환경유해성 물질 - 만성 구분 3 P273, P501
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.
P260 분진·흄·가스·미스트·증기·...·스프레이를 흡입하지 마시오.
P261 분진·흄·가스·미스트·증기·...·스프레이의 흡입을 피하시오.
P272 작업장 밖으로 오염된 의복을 반출하지 마시오.
P273 환경으로 배출하지 마시오.
P280 보호장갑/보호의/보안경/안면보호구를 착용하시오.
P391 누출물을 모으시오.
P301+P310 삼켰다면 즉시 의료기관(의사)의 진찰을 받으시오.
P308+P313 노출 또는 접촉이 우려되면 의학적인 조치· 조언를 구하시오.
P405 밀봉하여 저장하시오.
P501 ...에 내용물 / 용기를 폐기 하시오.

벤조(a)피렌 C화학적 특성, 용도, 생산

물성

벤조피렌(Benzo[a]pyrene, C20H12)은 다환방향족탄화수소(PAHs, polycyclic aromatic hydrocarbons) 그룹에 속하는 황색의 결정성 고체이며, 300-600℃사이 온도에서 불완전연소 생성되는 물질로서 에탄올 및 메탄올에 드물게 용해되고 벤젠, 톨루엔, 크실렌 및 에테르에 용해된다. 보통은 안정하나 빛과 공기 중에 분해되며 유기 용매 안의 B(a)P 용액은 공기와 빛에서 어두워지고 천천히 산화된다.

존재

300-600℃사이 온도에서 불완전연소 생성되기 때문에 오염원은 매우 다양하며 주로 콜타르, 자동차배출가스(특히 디젤엔진), 담배연기, 숯불구이 식품, 목재 연소 시에 발생한다.

개요

유전변이성과 발암성을 가지는 5개의 링 구조의 다환성 방향족 탄화수소로서 300~600℃의 온도 사이에서의 불완전연소에 의해 생성된다. 벤조피렌은 잔류기간이 길고 독성도 강하여 더욱 문제화되고 있는데 내분비계장애물질이면서 발암가능물질로서 주로 콜타르, 자동차배출가스(특히 디젤엔진), 담배연기에 존재한다.

용도

최근에는 탄 토스트 내에 유의적인 수준의 Benzo [a]pyrene이 발견되었다. 환경오염 등으로 인해 농산물, 어패류 등 조리·가공하지 않은 식품에도 벤조피렌이 존재하고 식품의 조리·가공 시 식품의 주성분인 탄수화물, 단백질, 지질 등이 분해되어 생성되기도 한다.

화학적 성질

yellow crystals or powder [found in cigarette smoke,

화학적 성질

B(a)P, is yellowish needles, crystals or powder. Odorless. PAHs are compounds containing multiple benzene rings and are also called polynuclear aromatic hydrocarbons.

물리적 성질

Odorless, yellow, orthorhombic or monoclinic crystals from ethanol. Solution in concentrated sulfuric acid is orange-red and fluoresces green under exposure to UV light (quoted, Keith and Walters, 1992).

용도

Benzopyrene is a polyaromatic hydrocarbon (PAH) found in coal tar. Benzopyrene is a known carcinogen. The metbolism of Benzopyrene results in diol epoxides that react and bind to DNA forming adducts which in turns leads to mutations and eventually cancer.

정의

ChEBI: An ortho- and peri-fused polycyclic arene consisting of five fused benzene rings.

정의

A cyclic aromatic hydrocarbon with a structure consisting of five fused benzene rings. It occurs in coal tar and tobacco smoke and has strong carcinogenic properties.

정의

benzopyrene: A crystalline aromatichydrocarbon, C20H12; m.p.179°C. It is found in coal tar and ishighly carcinogenic.

정의

benzpyrene: A pale yellow solid,C20H12, m.p. 179°C, whose moleculesconsist of five fused benzene rings. Itoccurs in tars from coal and tobaccosmoke and is a carcinogen.

일반 설명

A liquid. Presents a threat to the environment. Immediate steps should be taken to limits its spread to the environment. Easily penetrates the soil and contaminates groundwater or nearby waterways.

공기와 물의 반응

Insoluble in water.

반응 프로필

BENZO[A]PYRENE undergoes photo-oxidation after irradiation in indoor sunlight or by fluorescent light in organic solvents. Incompatible with strong oxidizing agents including various electrophiles, peroxides, nitrogen oxides and sulfur oxides. Oxidized by ozone, chromic acid and chlorinating agents. Readily undergoes nitration and halogenation. Hydrogenation occurs with platinum oxide .

위험도

Highly toxic, confirmed carcinogen by inhalation.

건강위험

The acute oral toxicity of benzo[a]pyrene islow. This may be due to the poor absorption of this compound by the gastrointestinal tract.The lethal dose in mice from intraperitonealadministration is reported as 500 mg/kg(NIOSH 1986).
Animal studies show sufficient evidence ofits carcinogenicity by all routes of exposureaffecting a variety of tissues, which includethe lungs, skin, liver, kidney, and blood.
Dasenbrock et al. (1996) have investigatedthe carcinogenic potency of carbon particles,diesel soot and benzo[a]pyrene in rats fromrepeated intracheal administration in a 16-week study. A total dose of 15 mg purebenzo[a]pyrene caused lung tumor in theexperimental animals at a rate similar tothat caused by diesel soot and carbon blackparticles.
Lodovici et al. (1998) measured the levelsof PAHs and benzo[a]pyrenediol epoxideDNA adduct in autoptic lung samples ofsmokers and non-smokers. Benzo[a]pyrenediol epoxide resulting from metabolic activation of benzo[a]pyrene binds to DNA to forman adduct, the levels of which can be used as abiomarker to evaluate the exposure of humansto benzo(a)pyrene.
Benz[a]pyrene exhibited teratogeniceffects in test species. It is a mutagen.It showed positive in a histidine rever-sion–Ames test, cell transform mouse embryotest, and in in vitro sister chromatid exchange(SCE)–human lymphocytes..

화재위험

Literature sources indicate that BENZO[A]PYRENE is nonflammable.

Toxicology

benzo[a]pyrene (BP) is a reasonably potent contact carcinogen, and therefore has been subjected to extensive carcinogenic testing. A diet containing 25 ppm of benzo[a]pyrene (BP) fed to mice for 140 days produced leukemia and lung adenomas in addition to stomach tumors. Skin tumors developed in over 60% of the rats treated topically with approximately 10 mg of benzo[a]pyrene three times per week. The incidence of skin tumors dropped to about 20% when treatment was about 3 mg  3 per week. Above the 10 mg range, however, the incidence of skin tumors increased dramatically to nearly 100%. benzo[a]pyrene (BP) is also carcinogenic when administered orally. In one experiment, weekly doses of greater than 10 mg administered for 10 weeks induced stomach cancers, although no stomach cancers were produced at the dose of 10 mg or less. At 100 mg doses, nearly 79% of the animals had developed stomach tumors by the completion of the experiment. When 15 ppm of benzo[a]pyrene (BP) in feed was orally administered to mice, production of leukemia, lung adenomas, and stomach tumors were observed after 140 days.

잠재적 노출

Benzopyrene (BP) is a PAH that has no commercial-scale production. B(a)P is produced in the United States by one chemical company and distributed by several specialty chemical companies in quantities from 100 mg to 5 g for research purposes. Although not manufactured in great quantity, B(a)P is a by-product of combustion. It is estimated that 1.8 million pounds per year are released from stationary sources, with 96% coming from: (1) coal refuse piles, outcrops, and abandoned coal mines; (2) residential external combustion of bituminous coal; (3) coke manufacture; and (4) residential external combustion of anthracite coal. Human exposure to B(a)P can occur from its presence as a by-product of chemical production. The number of persons exposed is not known. Persons working at airports in tarring operations; refuse incinerator operations; power plants, and coke manufacturers, may be exposed to higher B(a)P levels than the general population. Scientists involved in cancer research or in sampling toxic materials may also be occupationally exposed. The general population may be exposed to B(a)P from air pollution, cigarette smoke, and food sources. B(a) P has been detected in cigarette smoke at levels ranging from 0.2 to 12.2:g per 100 cigarettes. B(a)P has been detected at low levels in foods ranging from 0.1 to 50 ppb.

Source

MCLG: zero; MCL: 0.2 μg/L (U.S. EPA, 2000).
Identified in Kuwait and South Louisiana crude oils at concentrations of 2.8 and 0.75 ppm, respectively (Pancirov and Brown, 1975). Emitted to the environment from coke production, coal refuse and forest fires, motor vehicle exhaust, and heat and power (utility) generation (Suess, 1976). Benzo[a]pyrene is produced from combustion of tobacco and fuels. It is also a component of gasoline (133–143 μg/L), fresh motor oil (20 to 100 g/kg), used motor oil (83.2 to 242.4 mg/kg), asphalt (≤0.0027 wt %), coal tar pitch (≤1.25 wt %), cigarette smoke (25 μg/1,000 cigarettes), and gasoline exhaust (quoted, Verschueren, 1983). Detected in asphalt fumes at an average concentration of 14.72 ng/m3 (Wang et al., 2001). Benzo[a]pyrene was also detected in liquid paraffin at an average concentration of 25 μg/kg (Nakagawa et al., 1978).
Benzo[a]pyrene was reported in a variety of foodstuffs including raw and cooked meat (ND to 12 ppb), fish (0.3–6.9 ppb), vegetables oils (ND-4), fruits (ND to 6.2 ppb) (quoted, Verschueren, 1983).
The concentration of benzo[a]pyrene in coal tar and the maximum concentration reported in groundwater at a mid-Atlantic coal tar site were 3,600 and 0.0058 mg/L, respectively (Mackay and Gschwend, 2001). Based on laboratory analysis of 7 coal tar samples, benzo[a]pyrene concentrations ranged from 500 to 6,400 ppm (EPRI, 1990). In three high-temperature coal tars, benzo[a]pyrene concentrations ranged from 5,300 to 7,600 mg/kg (Lehmann et al., 1984). Benzo[a]pyrene was identified in a U.S. commercial creosote at an approximate concentration of 0.3% (Black, 1982). Nine commercially available creosote samples contained benzo[a]pyrene at concentrations ranging from 2 to 160 mg/kg (Kohler et al., 2000).
Identified in high-temperature coal tar pitches used in roofing operations at concentrations ranging from 4,290 to 13,200 mg/kg (Arrendale and Rogers, 1981; Malaiyandi et al., 1982). Lee et al. (1992a) equilibrated 8 coal tars with distilled water at 25 °C. The maximum concentration of benzo[a]pyrene observed in the aqueous phase was 1 μg/L.
Schauer et al. (2001) measured organic compound emission rates for volatile organic compounds, gas-phase semi-volatile organic compounds, and particle phase organic compounds from the residential (fireplace) combustion of pine, oak, and eucalyptus. The particle-phase emission rates of benzo[a]pyrene were 0.712 mg/kg of pine burned, 0.245 mg/kg of oak burned, and 0.301 mg/kg of eucalyptus burned.
Particle-phase tailpipe emission rates from gasoline-powered automobiles with and without catalytic converters were 0.021 and 41.0 μg/km, respectively (Schauer et al., 2002).
Under atmospheric conditions, a low rank coal (0.5–1 mm particle size) from Spain was burned in a fluidized bed reactor at seven different temperatures (50 °C increments) beginning at 650 °C. The combustion experiment was also conducted at different amounts of excess oxygen (5 to 40%) and different flow rates (700 to 1,100 L/h). At 20% excess oxygen and a flow rate of 860 L/h, the amount of benzo[a]pyrene emitted ranged from 39.4 ng/kg at 650 °C to 690.7 ng/kg at 850 °C. The greatest amount of PAHs emitted were observed at 750 °C (Mastral et al., 1999).

환경귀착

Biological. Benzo[a]pyrene was biooxidized by Beijerinckia B836 to cis-9,10-dihydroxy- 9,10-dihydrobenzo[a]pyrene. Under nonenzymatic conditions, this metabolite monodehydroxylated to form 9-hydroxybenzo[a]pyrene (quoted, Verschueren, 1983). Under aerobic conditions, Cunninghanella elegans degraded benzo[a]pyrene to trans-7,8-dihydroxy-7,8-dihydrobenzo[ a]pyrene (Kobayashi and Rittman, 1982), 3-hydroxybenzo[a]pyrene, 9-hydroxybenzo[ a]pyrene, and vicinal dihydrols including trans-9,10-dihydroxy-9,10-dihydrobenzo[a]pyrene (Cerniglia and Gibson, 1980; Gibson et al., 1975). The microorganisms Candida lipolytica and Saccharomyces cerevisiae oxidized benzo[a]pyrene to trans-7,8-dihydroxy-7,8-dihydrobenzo[ a]pyrene, 3- and 9-hydroxybenzo[a]pyrene (Cerniglia and Crow, 1980; Wiseman et al., 1978) whereas 3-hydroxybenzo[a]pyrene was the main degradation product by the microbe Neurospora crassa (Lin and Kapoor, 1979).
Soil. Lu et al. (1977) studied the degradation of benzo[a]pyrene in a model ecosystem containing Drummer silty clay loam. Samples were incubated at 27.6 °C for 1, 2, and 4 wk before extraction with acetone for TLC analysis. After 4 wk, only 8.05% of benzo[a]pyrene degraded forming one polar compound and two unidentified compounds. The reported half-lives for benzo[a]pyrene in a Kidman sandy loam and McLaurin sandy loam are 309 and 229 d, respectively (Park et al., 1990).
Surface Water. In a 5-m deep surface water body, the calculated half-lives for direct photochemical transformation at 40 °N latitude, in the midsummer during midday were 3.2 and 13 d with and without sediment-water partitioning, respectively (Zepp and Schlotzhauer, 1979). The volatilization half-life of benzo[a]pyrene from surface water (1 m deep, water velocity 0.5 m/sec, wind velocity 1 m/sec) using experimentally determined Henry’s law constants is estimated to be 1,500 h (Southworth, 1979).
Photolytic. Coated glass fibers exposed to air containing 100–200 ppb ozone yielded benzo[a]pyrene-4,5-oxide. At 200 ppb ozone, conversion yields of 50 and 80% were observed after 1 and 4 h, respectively (Pitts et al., 1990). In a similar study, kiln-fired glass fiber filters were coated with a mg of benzo[a]pyrene and exposed to oxygen containing 2 ppm ozone for 1 h. Degradation products identified using LC-atmospheric pressure chemical ionization-MS were benzo[a]pyrene-1,6-dione, benzo[a]pyrene-3,6-dione, benzo[a]pyrene-6,12-dione, benzo[a]pyrene- 4,5-dione, and 4-oxabenzo[d,e,f]chrysene-5-one (Letzel et al., 1999). Free radical oxidation and photolysis of benzo[a]pyrene at a wavelength of 366 nm yielded the following tentatively identified products: benzo[a]pyrene-1,6-quinone, benzo[a]pyrene-3,6-quinone, and benzo[a]pyrene- 6,12-quinone (Smith et al., 1978).
Chemical/Physical. Ozonolysis to benzo[a]pyrene-1,6-quinone or benzo[a]pyrene-3,6-quinone followed by additional oxidation to benzanthrone dicarboxylic anhydride was reported (IARC, 1983).

Purification Methods

A solution of 250mg of benzo[a]pyrene in 100mL of *benzene is diluted with an equal volume of hexane, then passed through a column of alumina, Ca(OH)2 and Celite (3:1:1). The adsorbed material is developed with a 2:3 *benzene/hexane mixture. (It showed as an intensely fluorescent zone.) The main zone is eluted with 3:1 acetone/EtOH, and is transferred into 1:1 *benzene-hexane by adding H2O. The solution is washed, dried with Na2SO4, evaporated and crystallised from *benzene by the addition of MeOH [Lijinsky & Zechmeister J Am Chem Soc 75 5495 1953]. Alternatively it can be chromatographed on activated alumina, eluted with a cyclohexane-*benzene mixture containing up to 8% *benzene, and the solvent evaporated under reduced pressure [Cahnmann Anal Chem 27 1235 1955], and crystallised from EtOH [Nithipatikom & McGown Anal Chem 58 3145 1986]. [Beilstein 5 III 2517, 5 IV 2687.] CARCINOGENIC.

비 호환성

Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides, nitrogen dioxide and ozone.

폐기물 처리

Incineration in admixture with a flammable solvent.

벤조(a)피렌 준비 용품 및 원자재

원자재

준비 용품


벤조(a)피렌 공급 업체

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