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아크릴로나이트릴

아크릴로나이트릴
아크릴로나이트릴 구조식 이미지
카스 번호:
107-13-1
한글명:
아크릴로나이트릴
동의어(한글):
아크릴로니트릴;벤PROPENENITRILE;비닐시아나이드;시아노에틸렌;아크릴론;크랍아크릴;2-프로펜니트릴;아크릴로나이트릴;프로펜니트릴;아크릴로니트릴모노모(ACRYLONITRILE,AN)
상품명:
Acrylonitrile
동의어(영문):
VCN;ent54;tl314;ENT 54;TL 314;Ventox;Acritet;Acrylon;CH2CHCN;NSC 6362
CBNumber:
CB8764818
분자식:
C3H3N
포뮬러 무게:
53.06
MOL 파일:
107-13-1.mol

아크릴로나이트릴 속성

녹는점
-83.5 °C
끓는 점
77.3 °C
밀도
0.806 g/mL at 20 °C
증기 밀도
1.83 (vs air)
증기압
86 mm Hg ( 20 °C)
굴절률
n20/D 1.391(lit.)
인화점
32 °F
저장 조건
2-8°C
용해도
73g/l
물리적 상태
Liquid
색상
Clear
냄새
Mild pyridine-like odor at 2 to 22 ppm
수소이온지수(pH)
6.0-7.5 (50g/l, H2O, 20℃)
폭발한계
2.8-28%(V)
수용성
Soluble. 7.45 g/100 mL
감도
Light Sensitive
Merck
14,131
BRN
605310
Henry's Law Constant
1.30 at 30.00 °C (headspace-GC, Hovorka et al., 2002)
노출 한도
NIOSH REL: TWA 1 ppm, 15-min C 1 ppm, IDLH 85 ppm; OSHA PEL: TWA 2 ppm, 15-min C 10 ppm; ACGIH TLV: TWA 2 ppm.
CAS 데이터베이스
107-13-1(CAS DataBase Reference)
NIST
2-Propenenitrile(107-13-1)
EPA
2-Propenenitrile(107-13-1)
안전
  • 위험 및 안전 성명
  • 위험 및 사전주의 사항 (GHS)
위험품 표기 F,T,N,Xn
위험 카페고리 넘버 45-11-23/24/25-37/38-41-43-51/53-39/23/24/25-62-63
안전지침서 53-9-16-45-61-36/37
유엔번호(UN No.) UN 1093 3/PG 1
WGK 독일 3
RTECS 번호 AT5250000
F 고인화성물질 8
자연 발화 온도 481 °C
TSCA Yes
위험 등급 3
포장분류 I
HS 번호 29261000
유해 물질 데이터 107-13-1(Hazardous Substances Data)
독성 LD50 orally in rats: 0.093 g/kg (Smyth, Carpenter)
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
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
H317 알레르기성 피부 반응을 일으킬 수 있음 피부 과민성 물질 구분 1 경고 P261, P272, P280, P302+P352,P333+P313, P321, P363, P501
H318 눈에 심한 손상을 일으킴 심한 눈 손상 또는 자극성 물질 구분 1 위험 P280, P305+P351+P338, P310
H331 흡입하면 유독함 급성 독성 물질 흡입 구분 3 위험 P261, P271, P304+P340, P311, P321,P403+P233, P405, P501
H335 호흡 자극성을 일으킬 수 있음 특정 표적장기 독성 - 1회 노출;호흡기계 자극 구분 3 경고
H350 암을 일으킬 수 있음 (노출되어도 암을 일으키지 않는다는 결정적인 증거가 있는 노출경로가 있다면 노출경로 기재) 발암성 물질 구분 1A, 1B 위험
H361 태아 또는 생식능력에 손상을 일으킬 것으로 의심됨 생식독성 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
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.
P260 분진·흄·가스·미스트·증기·...·스프레이를 흡입하지 마시오.
P261 분진·흄·가스·미스트·증기·...·스프레이의 흡입을 피하시오.
P273 환경으로 배출하지 마시오.
P280 보호장갑/보호의/보안경/안면보호구를 착용하시오.
P311 의료기관(의사)의 진찰을 받으시오.
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.
P305+P351+P338 눈에 묻으면 몇 분간 물로 조심해서 씻으시오. 가능하면 콘택트렌즈를 제거하시오. 계속 씻으시오.
P308+P313 노출 또는 접촉이 우려되면 의학적인 조치· 조언를 구하시오.
P405 밀봉하여 저장하시오.
P403+P233 용기는 환기가 잘 되는 곳에 단단히 밀폐하여 저장하시오.

아크릴로나이트릴 MSDS


Cyanoethylene

아크릴로나이트릴 C화학적 특성, 용도, 생산

용도

제품의 권고 용도와 사용상의 제한 본 제품은 실험실 및 연구용 시약 외의 용도로는 사용할 수 없음 다.

안전성

가.눈에 들어갔을 때 많은 양의 물이나 생리식염수로 15분 이상 눈을 세척하고 즉시 의사
의 치료를 받을 것.
나.피부에 접촉했을 때 오염된 의복 및 신발을 즉시 벗고 15분 이상 다량의 물과 비누로 씻
을 것.
다.흡입했을 때 노출로부터 환자를 즉시 신선한 공기가 있는 곳으로 옮기고 호흡정
지 및 곤란시 인공호흡 실시 및 의사의 치료를 받을 것.
라.먹었을 때 구토를 하지 않도록 하고 즉시 의사의 치료를 받을 것.
마.기타 의사의 주의사항 섭취의 경우 위 세척을 고려할 것.
흡입의 경우에는 산소의 공급을 고려할 것.
의료인력이 해당물질에 대해 인지하고 보호조치를 취하도록 할 것.

화학적 성질

Acrylonitrile is a colorless, flammable liquid. Its vapors may explode when exposed to an open flame. Acrylonitrile does not occur naturally. It is produced in very large amounts by several chemical industries in the United States and its requirement and demand has increased in recent years. The largest users of acrylonitrile are chemical industries that make acrylic and modacrylic fi bers, high impact acrylonitrile-butadiene-styrene (ABS) plastics. Acrylonitrile is also used in business machines, luggage, and construction material, in the manufacturing of styrene-acrylonitrile (SAN) plastics for automotive and household goods, and in packaging material. Adiponitrile is used to make nylon, dyes, drugs, and pesticides.

화학적 성질

The electronegativity of the cyanide group of acrylonitrile produces charge polarization and electron delocalization of the conjugated double bond.
Because of the electron deficiency of the ?-carbon, acrylonitrile readily adds to nucleophiles (RXH) by cyanoethylation.
This Michael addition reaction occurs almost quantitatively with alcohols, phenols, sulfhydryls, and amines with or without a catalyst (Rails 1959). The double bond with the partial positive charge on the ?-carbon is susceptible to oxidation reactions. The triple nitrile bond is susceptible to acid- or base-catalyzed hydrolysis to yield carboxylic acids.

물리적 성질

Clear, colorless to pale yellow-brown, watery, volatile liquid with a sweet, irritating or pungent odor resembling peach pits, onions, or garlic. Evaporates quickly when spilled. Turns dark on exposure to air. Odor threshold concentrations of 1.6 and 8.8 ppmv were reported by Stalker (1973) and Nagata and Takeuchi (1990), respectively.

용도

Acrylonitrile is used in the production of acrylic fibers, resins, and surface coating; as an intermediate in the production of pharmaceuticals and dyes; as a polymer modifier; and as a fumigant. It may occur in fire-effluent gases because of pyrolyses of polyacrylonitrile materials. Acrylonitrile was found to be released from the acrylonitrile–styrene copolymer and acrylonitrile–styrene–butadiene copolymer bottles when these bottles were filled with food-simulating solvents such as water, 4% acetic acid, 20% ethanol, and heptane and stored for 10 days to 5 months (Nakazawa et al. 1984). The release was greater with increasing temperature and was attributable to the residual acrylonitrile monomer in the polymeric materials.

용도

Manufacture of acrylic fibers. In the plastics, surface coatings, and adhesives industries. As a chemical intermediate in the synthesis of antioxidants, pharmaceuticals, dyes, surface-active agents, etc. In organic synthesis to introduce a cyanoethyl group. As a modifier for natural polymers. As a pesticide fumigant for stored grain. Experimentally to induce adrenal hemorrhagic necrosis in rats.

정의

ChEBI: A nitrile that is hydrogen cyanide in which the hydrogen has been replaced by an ethenyl group.

정의

A synthetic fiber that consists of a copolymer of 1-cyanoethene (acrylonitrile, vinyl cyanide) and ethenyl ethanoate (vinyl acetate).

생산 방법

Acrylonitrile can be prepared by several methods (HSDB 1988). Ethylene oxide is reacted with hydrogen cyanide to form ethylene cyanohydrin (?-hydroxypropionitrile), which is then dehydrated in the presence of a catalyst to form acrylonitrile. A somewhat similar synthesis involves the treatment of ethylene chlorohydrin with sodium cyanide to form ethylene cyanohydrin. Another method involves the partial oxidation of natural gas to acetylene which is then reacted with hydrogen cyanide to form acrylonitrile. Acrylonitrile also can be synthesized from propylene, oxygen and ammonia with either bismuth phosphomolybdate or a uranium- based compound as a catalyst (Hawley 1987).
Acrylonitrile is the most extensively produced aliphatic nitrile, ranking 39th on the list of high-volume chemicals produced in the USA in 1987. In 1985, U.S. production of acrylonitrile was 1.17 million tons (HSDB 1989).
Technical grade acrylonitrile is greater than 99% pure with the major impurities being water (present to a maximum of 0.5%), acetone, acetonitrile, acetaldehyde, iron, peroxides, and hydrogen cyanide (USEPA 1983). Polymerization grade acrylonitrile can contain the following impurities or additives: dimethylformamide, hydrogen peroxide, hydroxyanisole, methyl aery late, phenyl ether-biphenyl mixture, sodium metabisulfite, sulfur dioxide, sulfuric acid and titanium dioxide (USEPA 1980).

공기와 물의 반응

Highly flammable. Soluble in water.

반응 프로필

ACRYLONITRILE produces poisonous hydrogen cyanide gas on contact with strong acids or when heated to decomposition. Reacts violently with strong oxidizing agents (dibenzoyl peroxide, di-tert-butylperoxide, bromine) [Sax, 9th ed., p. 61]. Rapidly ignites in air and forms explosive mixtures with air. Polymerizes violently in the presence of strong bases or acids. Underwent a runaway reaction culminating in an explosion on contact with a small amount of bromine or solid silver nitrate [Bretherick, 5th ed., 1995, p. 404].

건강위험

Acrylonitrile is classified as moderately toxic by acute exposure through oral intake, skin contact, and inhalation. Symptoms of exposure include weakness, lightheadedness, diarrhea, nausea, and vomiting. Acrylonitrile is severely irritating to the eyes and mildly irritating to the skin; prolonged contact with the skin can lead to burns.
Acrylonitrile is mutagenic in bacterial and mammalian cell cultures and embryotoxic/ teratogenic in rats at levels that produce maternal toxicity. Acrylonitrile is carcinogenic in rats and is regulated by OSHA as a carcinogen (29 CFR 1910.1045). Acrylonitrile is listed in IARC Group 2A ("probable human carcinogen") and is classified as a "select carcinogen" under the criteria of the OSHA Laboratory Standard.

건강위험

Acrylonitrile is a highly toxic compound, an irritant to the eyes and skin, mutagenic, teratogenic, and causes cancer in test animals.
Acrylonitrile is a moderate to severe acute toxicant via inhalation, oral intake, dermal absorption, and skin contact. Inhalation of this compound can cause asphyxia and headache. Firefighters exposed to acrylonitrile have reported chest pains, headache, shortness of breath, lightheadedness, coughing, and peeling of skin from their lips and hands (Donohue 1983). These symptoms were manifested a few hours after exposure and persisted for a few days. Inhalation of 110 ppm for 4 hours was lethal to dogs. In humans, inhalation of about 500 ppm for an hour could be dangerous. The toxicity symptoms in humans from inhaling high concentrations of acrylonitrile were somnolence, diarrhea, nausea, and vomiting (ACGIH 1986).
Ingestion and absorption of acrylonitrile through the skin exhibited similar toxic symptoms: headache, lightheadedness, sneezing, weakness, nausea, and vomiting. In humans, the symptoms were nonspecific but related to the central nervous system, respiratory tract, gastrointestinal tract, and skin. Severe intoxication can cause loss of consciousness, convulsions, respiratory arrest, and death (Buchter and Peter 1984).
Investigating the acute and subacute toxicity of acrylonitrile, Knobloch et al. (1971) reported that the compound caused congestion in all types of organs and damage to the central nervous system, lungs, liver, and kidneys. A dose of 50 mg/kg/day given intraperitoneally to adult rats for 3 weeks resulted in body weight loss, leukocytosis, and functional disturbances and degeneration of the liver and kidneys. There was also light damage to the neuronal cells of the brain stem and cortex.
LD50 value, oral (mice): 27 mg/kg
LD50 value, subcutaneous (mice): 34 mg/kg
The lethal effect of acrylonitrile increased in rats when coadministered with organic solvents (Gut et al. 1981), although the latter decreased the formation of cyanide. Metabolic cyanide formation was found to play only a minor role in the inhalation toxicity of acrylonitrile (Peter and Bolt 1985). This was in contrast to the toxicity of methylacrylonitrile, where the observed clinical symptoms suggest a metabolically formed cyanide.
Combination of styrene and acrylonitrile enhanced the renal toxicity of the former in male rats (Normandeau et al. 1984). The lethal effect of acrylonitrile increased with hypoxia or the condition of inadequate supply of oxygen to the tissues (Jaeger and Cote 1982).
Acrylonitrile is a mild skin irritant. It caused severe irritation in rabbits’ eyes. Inhalation and oral and intraperitoneal dosages exhibited birth defects in rats and hamsters. Abnormalities in the central nervous system, as well as cytological changes and postimplantation mortality were the symptoms observed. Acrylonitrile is a mutagen. It tested positive in TRP reversion and histidine reversion–Ames tests. This compound caused cancer in test species. Inhalation and ingestion of this compound produced cancers in the brain, gastrointestinal tract, and skin in rats. An oral dose that was carcinogenic to rats was determined to be 18,000 mg/kg given over 52 weeks (NIOSH 1986).
Acrylonitrile is metabolized via two competing pathways: (1) glutathione conjugation leading to its detoxication and (2) oxidative pathways forming cyanoethylene oxide, a genotoxic epoxide. Thier et al. (2000) have postulated that there was much higher impact of the oxidative metabolism of acrylonitrile in humans than in the rodents. The authors recommend a combination of Nacetylcysteine with sodium thiosulfate for antidote therapy against acute intoxications.
Two independent studies on the oncogenicity of acrylonitrile in rats from oral dosing through drinking water were carried out recently (Quast 2002; Johannsen and Levinska 2002). Quast (2002) reported nontumorous and tumorous lesions in a number of tissues in rats from 2-year exposure. He observed a statistically significant increased incidence of tumors in the central nervous system, forestomach, tongue, small intestine and mammary gland at dose levels ranging between 3 to 25 mg/kg. A no-observed adverse-effect level (NOAEL) could not be determined in this study for toxicity or oncogenicity of acrylonitrile in either sex. Johannsen and Levinska (2002) also observed treatment-related tumors of the central nervous system (brain, spinal cord), ear canal and the gastrointestinal tract, and in females only, the mammary gland (intubation only). The degree of severity of forestomach hyperplasia increased in all high dose groups of animals.
Leonard et al. (1999) investigated mutagenicity, carcinogenicity and teratogenicity of acrylonitrile. Tests for mutagenicity in bacteria have been positive, however, those on chromosome aberrations in vivo were negative. Their studies indicated that the mutagenic effects on man depended on the conditions of exposure. While carcinogenicity of acrylonitrile in human could not be confirmed, the animal data established its carcinogenic potential, however, with certain limitations with respect to the species and the type of tumor. Acrylonitrile was found to be teratogenic in rats and hamsters, manifesting foetal/embryonic toxicity at high doses.
A review of epidemiological studies do not support any adequate evidence of lung cancer from inhalation of acrylonitrile in humans (Sakurai 2000) and therefore, the current occupational exposure limits of 2 ppm reported in such epidemiological studies seemed to be appropriate.

화재위험

Highly flammable liquid (NFPA rating = 3). Vapor forms explosive mixtures with air at concentrations of 3 to 17% (by volume). Hazardous gases produced in fire include hydrogen cyanide, carbon monoxide, and oxides of nitrogen. Carbon dioxide or dry chemical extinguishers should be used to fight acrylonitrile fires.

화재위험

Materials are too dangerous to health to expose fire fighters. A few whiffs of vapor could cause death or vapor or liquid could be fatal on penetrating the fire fighter's normal full protective clothing. The normal full protective clothing and breathing apparatus available to the average fire department will not provide adequate protection against inhalation or skin contact with these materials. Explosion hazard is moderate. Acrylonitrile is flammable and explosive at normal room temperatures. Can react violently with strong acids, amines, strong alkalis. Vapors may travel considerable distance to source of ignition and flash back. Dilute solutions are also hazardous (flash point of a solution of 2 percent in water is 70F). When heated or burned, toxic hydrogen cyanide gas and oxides of nitrogen are formed. Avoid strong acids, amines, alkalis. Incompatible with strong oxidizers (especially bromine) copper and copper alloys. Unstable, moderate hazard is possible when Acrylonitrile is exposed to flames, strong acids, amines and alkalis. May polymerize spontaneously in the container, particularly in absence of oxygen or on exposure to visible light. If polymerization occurs in containers, there is a possibility of violent rupture.

인화성 및 폭발성

Highly flammable liquid (NFPA rating = 3). Vapor forms explosive mixtures with air at concentrations of 3 to 17% (by volume). Hazardous gases produced in fire include hydrogen cyanide, carbon monoxide, and oxides of nitrogen. Carbon dioxide or dry chemical extinguishers should be used to fight acrylonitrile fires.

화학 반응

Reactivity with Water No reaction; Reactivity with Common Materials: Attacks copper and copper alloys; these metals should not be used. Penetrates leather, so contaminated leather shoes and gloves should be destroyed. Attacks aluminum in high concentrations; Stability During Transport: Stable; Neutralizing Agents for Acids and Caustics: Not pertinent; Polymerization: May occur spontaneously in absence of oxygen or on exposure to visible light or excessive heat, violently in the presence of alkali. Pure ACN is subject to polymerization with rapid pressure development. The commercial product is inhibited and not subject to this reaction; Inhibitor of Polymerization: Methylhydroquinone (35-45 ppm).

공업 용도

Acrylonitrile is used in the manufacture of acrylic fibers; in plastics, surface coatings, and adhesives industries; as a chemical intermediate in the synthesis of anti-oxidants, pharmaceuticals, dyes, surface-active agents, etc.; and in organic synthesis to introduce a cyanoethyl group. It is used as a modifier for natural polymers, and as a pesticide fumigant for stored grain (Hawley 1987; Windholz et al 1983; HSDB 1989).
Other uses for acrylonitrile includes the cyanoethylation of natural fibers such as cotton, cellulose, and polysaccharides and the production of acrylonitrilecontaining plastics, particularly styrene-acrylonitrile (SAN) and acrylonitrilebutadiene styrene (ABS) co-polymers. Acrylonitrile is also used in the manufacture of various resins, elastomers, and latexes and has a limited use as a fumigant.
The major source of human exposure to acrylonitrile monomer and its release into the environment is during its manufacture, polymerization, or molding to acrylonitrile-based polymers. Disposal of acrylonitrile polymers by burning results in release of additional acrylonitrile monomer. Residual amounts of acrylonitrile monomer also are released from fabrics, such as underwear made of polyacrylonitrile fibers, and acrylonitrile polymer plastics in furniture. The public may also be exposed to acrylonitrile by ingestion of food products containing leached residual acrylonitrile monomer from packaging materials, such as 'Saran Wrap' (Anon. 1977a,b). Cigarette smoke has been shown by gas Chromatographie analysis to contain aliphatic nitriles including acrylonitrile, propionitrile, and methacrylonitrile (Izard and Testa 1968).

색상 색인 번호

Acrylonitrile is a raw material used extensively in industry, mainly for acrylic and modacrylic fibers, acrylonitrile-butadiene-styrene and styrene-acrylonitrile resins, adiponitrile used in nylon’s synthesis, for nitrile rubber, and plastics. It is also used as an insecticide. This very toxic and irritant substance is also a sensitizer and caused both irritant and allergic contact dermatitis in a production manufacturer.

Safety Profile

Confirmed human carcinogen with experimental carcinogenic, neoplastigenic, and tumorigenic data. Poison by inhalation, ingestion, skin contact, and other routes. Human systemic effects by inhalation and skin contact: conjunctiva irritation, somnolence, general anesthesia, cyanosis, and diarrhea. An experimental teratogen. Other experimental reproductive effects. Human mutation data reported. Dangerous fire hazard when exposed to heat, flame, or oxiduers. Moderate explosion hazard when exposed to flame. Can react vigorously with oxidizing materials (see also CYANIDE). Acrylonitrile closely resembles hydrocyanic acid in its toxic action. By inhibiting the respiratory enzymes of tissue, it renders the tissue cells incapable of oxygen absorption. Poisoning is acute; there is little evidence of cumulative action on repeated exposure. Exposure to low concentration is followed by flushing of the face and increased salivation; further exposure results in irritation of the eyes and nose, photophobia, deepened respiration. If exposure continues, shallow respiration, nauseanausea, vomiting, weakness, an oppressive feeling in the chest, and occasionally headache and diarrhea are other complaints. Several cases of mild jaundice accompanied by mild anemia and leucocytosis have been reported. Urinalysis is generally negative, except for an increase in bile pigment. Serum and bile thocyanates are raised. See also HYDROCYANIC ACID. Unstable and easily oxidued. Explosive polymerization may occur on storage with silver nitrate. Potentially explosive reactions with benzyltrimethylammonium hydroxide + pyrrole, tetrahydrocarbazole + benzyltrimethylammonium hydroxide. Violent reactions with strong acids (e.g., nitric or sulfuric), strong bases, azoisobutyronitrile, dibenzoyl peroxide, ditert-butylperoxide, or bromine. Incompatible with AgNO3 and amines. To fight fire, use CO2, dry chemical, or alcohol foam. When heated to decomposition it emits toxic fumes of NOx and CN-. See also NITRILES and CYANIDE.

잠재적 노출

Acrylonitrile is used in the manufacture of synthetic fibers, polymers, acrylostyrene plastics, acrylonitrile butadiene styrene plastics, nitrile rubbers, chemicals, and adhesives. It is also used as a pesticide. In the past, this chemical was used as a room fumigant and pediculicide (an agent used to destroy lice).

환경귀착

Biological. Degradation by the microorganism Nocardia rhodochrous yielded ammonium ion and propionic acid, the latter being oxidized to carbon dioxide and water (DiGeronimo and Antoine, 1976). When 5 and 10 mg/L of acrylonitrile were statically incubated in the dark at 25°C with yeast extract and settled domestic wastewater inoculum, complete degradation was observed after 7 days (Tabak et al., 1981)
Photolytic. In an aqueous solution at 50°C, UV light photooxidized acrylonitrile to carbon dioxide. After 24 hours, the concentration of acrylonitrile was reduced 24.2% (Knoevenagel and Himmelreich, 1976)
Chemical/Physical. Ozonolysis of acrylonitrile in the liquid phase yielded formaldehyde and the tentatively identified compounds glyoxal, an epoxide of acrylonitrile and acetamide (Munshi et al., 1989). In the gas phase, cyanoethylene oxide was
The hydrolysis rate constant for acrylonitrile at pH 2.87 and 68°C was determined to be 6.4 × 10–3/hour, resulting in a half-life of 4.5 days. At 68.0°C and pH 7.19, no hydrolysis/disappearance was observed after 2 days. However, when the pH was raised to 10.76, the hydrolysis half-life was calculated to be 1.7 hours (Ellington et al., 1986)Acrylonitrile hydrolyzes to acrylamide which undergoes further hydrolysis forming acrylic acid and ammonia (Kollig, 1993)

신진 대사

Extensive metabolic studies have been reported which explain in part, the bioactivation and degradation of acrylonitrile. Increased blood and urine concentrations of thiocyanate in animals were reported after acrylonitrile administration (Giacosa 1883). Brieger et al (1952), found that acute acrylonitrile exposure also produced increased blood concentrations of cyanomethemoglobin. In dogs (which are particularly susceptible to acrylonitrile toxicity), the concentration of cyanomethemoglobin increased with length of exposure, so that by the end of the lethal exposure period most of the methemoglobin present was converted to cyanomethemoglobin.
Acrylonitrile, clearly, is capable of liberating cyanide under biological conditions. However, the percentage of the total urinary excretion of thiocyanate after acrylonitrile administration ranges from 4 to 25% of the administrated dose (Ahmed and Patel 1981; Brieger et al 1952; Benes and Cerna 1959; Farooqui and Ahmed 1981; Paulet et al 1966).
Gut et al (1975) found that the conversion of acrylonitrile to cyanide was dependent on the route of administration and decreased in the following order: oral > intraperitoneal > subcutaneous > intravenous. Thus, the more slowly acrylonitrile enters the system (oral administration), the more extensively it is converted to cyanide. This suggests that conversion of acrylonitrile to cyanide involves saturable metabolic processes.
Ahmed and Patel (1981) studied the metabolism of acrylonitrile to cyanide in both rats and mice. In rats, early signs of acrylonitrile toxicity were cholinomimetic, which were different from the central nervous system disturbances observed after giving potassium cyanide. However, in mice, the only signs of acrylonitrile toxicity were central nervous system effects; these were identical to those seen after giving potassium cyanide. Treatment of rats and mice with phenobarbital, Aroclor 1254, or fasting increased blood cyanide concentrations, whereas treatment with cobaltous chloride or SKF 525A resulted in decreased blood cyanide concentrations. The data previously cited indicates species differences in acrylonitrile toxicity and metabolism which suggest that acrylonitrile is metabolized to cyanide by a mixed-function oxidase (mfo) enzyme system.
In vitro, the metabolism of acrylonitrile to cyanide was localized in the microsomal fraction of rat liver and required NADPH and O2 (Abreu and Ahmed 1979, 1980; Ahmed and Abreu 1982). Metabolism of acrylonitrile was increased in microsomes obtained from phenobarbital, Aroclor 1254, and 3-methylcholanthrene treated rats and decreased after cobaltous chloride treatment. Addition of SKF 525A or carbon monoxide to the incubation mixture inhibited acrylonitrile metabolism. Addition of the epoxide hydrolase inhibitor, 1,1,1-trichloropropane 2,3-oxide, decreased the formation of cyanide from acrylonitrile. The addition of glutathione (GSH), cysteine, D-penicillamine, or 2-mercaptoethanol enhanced the release of cyanide by a cytochrome P-450-dependent mfo system.
Earlier investigators believed that the aliphatic nitriles, including acrylonitrile, might be direct inhibitors of cytochrome c oxidase. The in vitro studies in our laboratory (Ahmed et al 1980; Ahmed and Farooqui 1982), and studies by Willhite and Smith (1981), and Nerudova et al (1981) showed no inhibition of cytochrome c oxidase by nitriles. Nerudova et al (1981) reported that the administration of lethal (100 mg/kg) or sublethal doses (40 mg/kg =LD50) of acrylonitrile to mice inhibited cytochrome c oxidase in liver and brain. In rats, after giving LD50 doses of acrylonitrile, a 50% inhibition of cytochrome c oxidase in liver, kidney and brain was observed by Ahmed and Farooqui (1982). Nerudova et al (1981) suggested that after the administration of a lethal, as well as LD50, dose of acrylonitrile, cyanide is present in the organism in a concentration that produces a 50% inhibition of cytochrome c oxidase.

저장

Work with acrylonitrile should be conducted in a fume hood to prevent exposure by inhalation, and splash goggles and impermeable gloves should be worn at all times to prevent eye and skin contact. Acrylonitrile should be used only in areas free of ignition sources. Containers of acrylonitrile should be stored in secondary containers in the dark in areas separate from oxidizers and bases.

운송 방법

UN1093 Acrylonitrile, stabilized, Hazard Class 3; Labels: 3 Flammable liquids, 6.1-Poisonous materials

Purification Methods

Wash acrylonitrile with dilute H2SO4 or dilute H3PO4, then with dilute Na2CO3 and water. Dry it with Na2SO4, CaCl2 or (better) by shaking with molecular sieves. Fractionally distil it under N2. It can be stabilised by adding 10ppm tert-butyl catechol. Immediately before use, the stabilizer can be removed by passage through a column of activated alumina (or by washing with 1% NaOH solution if traces of water are permissible in the final material), followed by distillation. Alternatively, shake it with 10% (w/v) NaOH to extract inhibitor, and then wash it in turn with 10% H2SO4, 20% Na2CO3 and distilled water. Dry for 24hours over CaCl2 and fractionally distil under N2 taking fraction boiling at 75.0-75.5oC (at 734mm). Store it with 10ppm tert-butyl catechol. Acrylonitrile is distilled off when required. [Burton et al. J Chem Soc, Faraday Trans 1 75 1050 1979, Beilstein 2 IV 1473.]

비 호환성

May form explosive mixture with air. Reacts violently with strong acids; strong alkalis; bromine, and tetrahydrocarbazole. Copper, copper alloys, ammonia, and amines may cause breakdown to poisonous products. Unless inhibited (usually with methylhydroquinone), acrylonitrile may polymerize spontaneously. It may also polymerize on contact with oxygen, heat, strong light, peroxides, and concentrated or heated alkalis. Reacts with oxidizers, acids, bromine, amines. Attacks copper and copper alloys. Attacks aluminum in high concentrations. Heat and flame may cause release of poisonous cyanide gas and nitrogen oxides

폐기물 처리

Consult with environmental regulatory agencies for guidance on acceptable disposal practices. Generators of waste containing this contaminant (≥100 kg/mo) must conform with EPA regulations governing storage, transportation, treatment, and waste disposal. Incineration with provision for nitrogen oxides removal from effluent gases by scrubbers or afterburners. A chemical disposal method has also been suggested involving treatment with alcoholic NaOH; the alcohol is evaporatedand calcium hypochlorite added; after 24 hours the product is flushed to the sewer with large volumes of water. Recovery of acrylonitrile from acrylonitrile process effluents is an alternative to disposal.

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