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アクリロニトリル 化学構造式
アクリロニトリル;2-プロペンニトリル;ベントックス;プロペンニトリル;アクリロン;フミグレイン;アクリテト;ビニルシアニド;シアノエチレン;カルバクリル;アクリル酸ニトリル;アクリロニトリル CRM4040-A;アクリルニトリル;アクリロニトリル CRM4040‐B;アクリロニトリル STANDARD;アクリロニトリル 溶液;アクリロニトリル Standard, 10 mg/mL in MeOH;アクリロニトリル Standard, 100 µg/mL in MeOH;アクリロニトリル, 10 mg/mL in Water;アクリロニトリル, 1000 µg/mL in MeOH
VCN;ent54;tl314;ENT 54;TL 314;Ventox;Acritet;Acrylon;CH2CHCN;NSC 6362
MOL File:

アクリロニトリル 物理性質

融点 :
-83 °C (lit.)
沸点 :
77 °C (lit.)
比重(密度) :
0.806 g/mL at 20 °C
1.83 (vs air)
86 mm Hg ( 20 °C)
屈折率 :
n20/D 1.391(lit.)
闪点 :
32 °F
貯蔵温度 :
外見 :
6.0-7.5 (50g/l, H2O, 20℃)
臭い (Odor):
Mild pyridine-like odor at 2 to 22 ppm
臭気閾値(Odor Threshold):
爆発限界(explosive limit):
水溶解度 :
Soluble. 7.45 g/100 mL
Sensitive :
Light Sensitive
Merck :
Henry's Law Constant:
1.30 at 30.00 °C (headspace-GC, Hovorka et al., 2002)
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 データベース:
107-13-1(CAS DataBase Reference)
2B (Vol. 71) 1999
Acrylonitrile (107-13-1)
  • リスクと安全性に関する声明
  • 危険有害性情報のコード(GHS)
主な危険性  F,T,N,Xn
Rフレーズ  45-11-23/24/25-37/38-41-43-51/53-39/23/24/25-62-63
Sフレーズ  53-9-16-45-61-36/37
RIDADR  UN 1093 3/PG 1
WGK Germany  3
RTECS 番号 AT5250000
自然発火温度 481 °C
国連危険物分類  3
容器等級  I
HSコード  29261000
有毒物質データの 107-13-1(Hazardous Substances Data)
毒性 LD50 orally in rats: 0.093 g/kg (Smyth, Carpenter)
消防法 危険物第4類第一石油類(非水溶性)
化審法 (2)-1513 優先評価化学物質
安衛法 特化則 特定化学物質(特定第2類) 変異原性物質
PRTR法 第一種指定化学物質
毒劇物取締法 劇物
注意喚起語 Danger
コード 危険有害性情報 危険有害性クラス 区分 注意喚起語 シンボル P コード
H225 引火性の高い液体および蒸気 引火性液体 2 危険 P210,P233, P240, P241, P242, P243,P280, P303+ P361+P353, P370+P378,P403+P235, P501
H301 飲み込むと有毒 急性毒性、経口 3 危険 P264, P270, P301+P310, P321, P330,P405, P501
H311 皮膚に接触すると有毒 急性毒性、経皮 3 危険 P280, P302+P352, P312, P322, P361,P363, P405, P501
H315 皮膚刺激 皮膚腐食性/刺激性 2 警告 P264, P280, P302+P352, P321,P332+P313, P362
H317 アレルギー性皮膚反応を起こすおそれ 感作性、皮膚 1 警告 P261, P272, P280, P302+P352,P333+P313, P321, P363, P501
H318 重篤な眼の損傷 眼に対する重篤な損傷性/眼刺激 性 1 危険 P280, P305+P351+P338, P310
H331 吸入すると有毒 急性毒性、吸入 3 危険 P261, P271, P304+P340, P311, P321,P403+P233, P405, P501
H335 呼吸器への刺激のおそれ 特定標的臓器毒性、単回暴露; 気道刺激性 3 警告
H350 発がんのおそれ 発がん性 1A, 1B 危険
H361 生殖能または胎児への悪影響のおそれの疑い 生殖毒性 2 警告 P201, P202, P281, P308+P313, P405,P501
H370 臓器の障害 特定標的臓器有害性、単回暴露 1 危険 P260, P264, P270, P307+P311, P321,P405, P501
H411 長期的影響により水生生物に毒性 水生環境有害性、慢性毒性 2
P201 使用前に取扱説明書を入手すること。
P210 熱/火花/裸火/高温のもののような着火源から遠ざ けること。-禁煙。
P260 粉じん/煙/ガス/ミスト/蒸気/スプレーを吸入しないこ と。
P261 粉じん/煙/ガス/ミスト/蒸気/スプレーの吸入を避ける こと。
P273 環境への放出を避けること。
P280 保護手袋/保護衣/保護眼鏡/保護面を着用するこ と。
P301+P310 飲み込んだ場合:直ちに医師に連絡すること。
P303+P361+P353 皮膚(または髪)に付着した場合:直ちに汚染された衣 類をすべて脱ぐこと/取り除くこと。皮膚を流水/シャワー で洗うこと。
P305+P351+P338 眼に入った場合:水で数分間注意深く洗うこと。次にコ ンタクトレンズを着用していて容易に外せる場合は外す こと。その後も洗浄を続けること。
P311 医師に連絡すること。
P405 施錠して保管すること。

アクリロニトリル 価格 もっと(32)

メーカー 製品番号 製品説明 CAS番号 包装 価格 更新時間 購入
富士フイルム和光純薬株式会社(wako) W01W0101-0078 アクリロニトリル 97.0+% (Capillary GC)
Acrylonitrile 97.0+% (Capillary GC)
107-13-1 25mL ¥1550 2021-03-23 購入
富士フイルム和光純薬株式会社(wako) W01S24NMIJCRM4040-B アクリロニトリル
107-13-1 15mL ¥26860 2021-03-23 購入
東京化成工業 A0146 アクリロニトリル >99.0%(GC)
Acrylonitrile (stabilized with MEHQ) >99.0%(GC)
107-13-1 25mL ¥1600 2021-03-23 購入
東京化成工業 A0146 アクリロニトリル >99.0%(GC)
Acrylonitrile (stabilized with MEHQ) >99.0%(GC)
107-13-1 500mL ¥2500 2021-03-23 購入
関東化学株式会社(KANTO) 01082-01 アクリロニトリル >98.0%(GC)
Acrylonitrile >98.0%(GC)
107-13-1 500mL ¥2400 2021-03-23 購入

アクリロニトリル MSDS


アクリロニトリル 化学特性,用途語,生産方法


無色~わずかにうすい黄色, 澄明の液体


水に可溶 (9.3g/100g水, 20℃), ほとんどの有機溶剤に易溶。エタノール及びアセトンに極めて溶けやすく、水にやや溶けやすい。


C3H3N(53.06).CH2=CHCN.工業的に,初期にはアセチレンと青酸の反応で合成されたが,ソハイオ法の出現以来,すべてプロペンのアンモ酸化反応によって合成されるようになった."触媒としては,まずモリブデン酸ビスマス,またはリンモリブデン酸ビスマスが用いられたが,その後,多くの改良触媒が開発されている.特異臭をもつ無色の液体.融点-83 ℃,沸点77.3 ℃.d200.8060.n20D 1.3911.多くの有機溶剤に易溶.蒸気は有毒性で,空気中20 ppm 以上は危険である.アクリル系合成繊維の単量体として工業的に大量に使用され,またブタジエンと共重合して合成ゴムNBR,ブタジエン,スチレンと共重合してABS樹脂が製造される.このほか,各種の高分子原料,有機合成原料として使用される.[CAS 107-13-1]


合成繊維?アクリロニトリル-ブタジエン-スチレン(ABS)樹脂?アクリロニトリル-スチレン(AS)樹脂原料,合成ゴム (ニトリルゴム)樹脂原料、塗料?繊維樹脂加工?化粧品原料?合成糊料合成原料、アクリルアミド(紙力増強剤,凝集剤)重合原料、NITE初期リスク評価書;合成繊維?合成ゴム?プラスチック原料、アクリルアミド?アジポニトリル原料、SRI:CHEMICAL ECONOMICS HANDBOOK;合成繊維?合成ゴム?プラスチック原料 (化学工業日報社)


Acrylonitrile is very toxic and irritant but is also a sensitizer. It caused both irritant and allergic contact dermatitis in a production manufacture.


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.


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.


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.


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.


Acrylonitrile is a raw material used for synthesis of many synthetic fibers such as Dralon and acrylic fibers. It is also used as an insecticide.


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.


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


Acrylonitrile is produced in commercial quantities almost exclusively by the vapor-phase catalytic propylene ammoxidation process developed by Sohio.
C3H6 + NH3 + 2/3O2???→ C3H3N +3 H2O
Acrylonitrile must be stored in tightly closed containers in cool, dry, well-ventilated areas away from heat, sources of ignition, and incompatible chemicals. Storage vessels, such as steel drums, must be protected against physical damage, with outside detached storage preferred. Storage tanks and equipment used for transferring acrylonitrile should be electrically grounded to reduce the possibility of static spark-initiated fire or explosion. Acrylonitrile is regulated in the workplace by OSHA (29 CFR 1910).


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


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).


Highly flammable. Soluble in water.


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].


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.


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.


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.


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).


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).


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.

Biochem/physiol Actions

An industrial carcinogen that is a multisite carcinogen in rats and possibly carcinogenic to humans.


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).


Acrylonitrile is reasonably anticipated to be a human carcinogenbased on sufficient evidence of carcinogenicity from studies in experimental animals.


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)


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.


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.


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


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.]

Toxicity evaluation

Acrylonitrile is both readily volatile in air and highly soluble in water. These characteristics determine the behavior of acrylonitrile in the environment. The principal pathway leading to the degradation of acrylonitrile in air is photooxidation, mainly by reaction with hydroxyl radicals (OH). Acrylonitrile may also be oxidized by other atmospheric components such as ozone and oxygen. Very little is known about the nonbiologically mediated transformation of acrylonitrile in water. It is oxidized by strong oxidants such as chlorine used to disinfect water. Acrylonitrile is readily degraded by aerobic microorganisms in water.


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


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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