107-13-1

Name	Acrylonitrile
CAS	107-13-1
EINECS(EC#)	203-466-5
Molecular Formula	C3H3N
MDL Number	MFCD00001927
Molecular Weight	53.06
MOL File	107-13-1.mol

Chemical Properties

Description	Acrylonitrile is a colourless, flammable liquid. Its vapours 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 are increasing in recent years. Acrylonitrile is a heavily produced, unsaturated nitrile. It is used to make other chemicals such as plastics, synthetic rubber, and acrylic fibres. It has been used as a pesticide fumigant in the past; however, all pesticide uses have been discontinued. This compound is a major chemical intermediate used in creating products such as pharmaceuticals, antioxidants, and dyes, as well as in organic synthesis. The largest users of acrylonitrile are chemical industries that make acrylic and modacrylic fibres and high-impact ABS plastics. Acrylonitrile is also used in business machines, luggage, construction material, and manufacturing of styrene-acrylonitrile (SAN) plastics for automotive, household goods, and packaging material. Adiponitrile is used to make nylon, dyes, drugs, and pesticides. less more
Appearance	Acrylonitrile is a highly flammable, clear, colorless or light yellowish liquid. Irritating, faint garlicor onion-like odor. Its odor threshold is 17 ppm; odor can only be detected above the PEL
Melting point	-83.5 °C
Boiling point	77.3 °C
density	0.806 g/mL at 20 °C
vapor density	1.83 (vs air)
vapor pressure	86 mm Hg ( 20 °C)
refractive index	n20/D 1.391(lit.)
Fp	32 °F
storage temp.	2-8°C
solubility	73g/l
form	Liquid
color	Clear
Odor	Mild pyridine-like odor at 2 to 22 ppm
PH	6.0-7.5 (50g/l, H2O, 20℃)
explosive limit	2.8-28%(V)
Odor Threshold	8.8ppm
Water Solubility	Soluble. 7.45 g/100 mL
Sensitive	Light Sensitive
Merck	14,131
BRN	605310
Henry's Law Constant	1.30 at 30.00 °C (headspace-GC, Hovorka et al., 2002)
Dielectric constant	33.009999999999998
Exposure limits	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.
Contact allergens	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. less more
LogP	0.017 at 21℃
CAS DataBase Reference	107-13-1(CAS DataBase Reference)
IARC	2B (Vol. 71) 1999
NIST Chemistry Reference	2-Propenenitrile(107-13-1)
EPA Substance Registry System	107-13-1(EPA Substance)

Safety Data

Hazard Codes	F,T,N
Risk Statements	R45:May cause cancer. R11:Highly Flammable. R23/24/25:Toxic by inhalation, in contact with skin and if swallowed . R37/38:Irritating to respiratory system and skin . R41:Risk of serious damage to eyes. R43:May cause sensitization by skin contact. R51/53:Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment . R39/23/24/25:Toxic: danger of very serious irreversible effects through inhalation, in contact with skin and if swallowed . less more
Safety Statements	S53:Avoid exposure-obtain special instruction before use . S9:Keep container in a well-ventilated place . S16:Keep away from sources of ignition-No smoking . S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) . S61:Avoid release to the environment. Refer to special instructions safety data sheet . S36/37:Wear suitable protective clothing and gloves . less more
RIDADR	UN 1093 3/PG 1
WGK Germany	3
RTECS	AT5250000
F	8
Autoignition Temperature	481 °C
TSCA	Yes
HazardClass	3
PackingGroup	I
HS Code	29261000
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. less more
Hazardous Substances Data	107-13-1(Hazardous Substances Data)
Toxicity	LD50 orally in rats: 0.093 g/kg (Smyth, Carpenter) less more
IDLA	60 ppm

Raw materials And Preparation Products

Hazard Information

Chemical Properties

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.

Definition

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

Reactivity Profile

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].

Air & Water Reactions

Highly flammable. Soluble in water.

Health Hazard

ACRYLONITRILE, INHIBITED is classified as very toxic. Probable oral lethal dose for human is 50-500 mg/kg (between 1 teaspoon and 1 oz.) for a 70 kg (150 lb.) person. Irritant skin dose--500 mg. Toxic concentrations have been reported at 16 ppm/20 min. Acute toxicity is similar to that due to cyanide poisoning, and the level of cyanide ion in blood is related to the level of poisoning. Inhalation or ingestion results in collapse and death due to tissue anoxia (lack of oxygen) and cardiac arrest (heart failure).

Potential Exposure

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).

Fire Hazard

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, INHIBITED 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, INHIBITED 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.

First aid

If this chemical gets into the eyes, remove any contact lenses at once and irrigate immediately for at least 15 minutes, occasionally lifting upper and lower lids. Seek medical attention immediately. If this chemical contacts the skin, remove contaminated clothing and wash immediately with soap and water. Seek medical attention immediately. If this chemical has been inhaled, remove from exposure, begin rescue breathing (using universal precautions, including resuscitation mask) if breathing has stopped and CPR if heart action has stopped. Transfer promptly to a medical facility. When this chemical has been swallowed, get medical attention. Give large quantities of water and induce vomiting. Do not make an unconscious person vomit. Medical observation is recommended for 24 to 48 hours after breathing overexposure, as pulmonary edema may be delayed. Use amyl nitrate capsules if symptoms develop. All area employees should be trained regularly in emergency measures for cyanide poisoning and in CPR. A cyanide antidote kit should be kept in the immediate work area and must be rapidly available. Kit ingredients should be replaced every 1 2 years to ensure freshness. Persons trained in the use of this kit; oxygen use, and CPR must be quickly available.

Shipping

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

Incompatibilities

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

Waste Disposal

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.

Physical properties

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 ppm_v were reported by Stalker (1973) and Nagata and Takeuchi (1990), respectively.

Production Methods

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).

Production Methods

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).

Flammability and Explosibility

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.

Chemical Reactivity

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).

Industrial uses

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).

Biochem/physiol Actions

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

Carcinogenicity

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

Environmental Fate

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)

Metabolism

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.

storage

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.

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.]

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.

Material Safety Data Sheet(MSDS)

Questions And Answer

Description
Acrylonitrile is a colourless, flammable liquid. Its vapours 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 are increasing in recent years. Acrylonitrile is a heavily produced, unsaturated nitrile. It is used to make other chemicals such as plastics, synthetic rubber, and acrylic fibres. It has been used as a pesticide fumigant in the past; however, all pesticide uses have been discontinued. This compound is a major chemical intermediate used in creating products such as pharmaceuticals, antioxidants, and dyes, as well as in organic synthesis. The largest users of acrylonitrile are chemical industries that make acrylic and modacrylic fibres and high-impact ABS plastics. Acrylonitrile is also used in business machines, luggage, construction material, and manufacturing of styrene-acrylonitrile (SAN) plastics for automotive, household goods, and packaging material. Adiponitrile is used to make nylon, dyes, drugs, and pesticides.

Acrylonitrile-3D-balls;
Usage History
On the eve of World War II, it was discovered that acrylonitrile copolymer can improve the oil resistance and solvent resistance of synthetic rubber and people began to be taken it seriously. During the war, it was developed in Germany of the manufacturing process through epoxidation of ethylene, followed by addition with hydrogen cyanide to produce cyanide ethanol, and finally dehydration. It was later developed of addition of hydrogen cyanide to acetylene under the catalysis of cuprous chloride. After 1960, it had been developed of new production process in the Ohio standard oil company, using propylene as raw material for ammoxidation reaction to obtain it. This process has led to great changes in industrial production. Owing to the availability of raw materials and the reduction in the cost, there is a sudden surge in production of acrylonitrile. In 1983, the world's annual output reached 3 million tons, of which the production amount of Ohio standard oil can account for 90%.
Acrylonitrile is easy to undergo polymerization, being able to produce polyacrylonitrile fiber (under the trade name of acrylic or bulk). Its short fiber is similar to wool, also known as artificial wool. It feels soft by hand with excellent elasticity. It can co-polymerize with vinyl acetate to generate synthetic fibers (under the commercial name of Austrian Lun). In 1950, it was first put into industrial production by the United States DuPont. The majority of acrylonitrile is used for synthetic fiber with the amount accounting for about 40~60% of the total. With copolymerization with butadiene copolymerization, it can generate oil-resistant nitrile rubber. Acrylonitrile dimerization and hydrogenation can be lead to adiponitrile, with then hydrogenation being able to obtain hexamethylene diamine, which is one of the raw materials of polyamide (nylon 66). The co-polymer of acrylonitrile and butadiene, styrene terpolymer is a high-quality engineering plastics, referred to as ABS resin.;
Chemical properties
Acrylonitrile is a clear, colorless to pale-yellow liquid with molecular formula C3H3N and molecular weight of 53.06. The yellowing color is upon exposure to light and indicate photo-alteration to saturate derivate. It is practically odorless, or with a very slight odor that may be describe as sweet, irritating, unpleasant, onion or garlic-like or pungent. Odor can only be detected above PEL. Boiling point of 77.3°C and melting point of −82 °C. The specific gravity is 0.8004 @ 25 deg C, pH is from 6.0 to 7.5 (5% aqueous solution), vapor density of 1.8 (Air=1), Vapor pressure 109 mm Hg @ 25°C. The Henry law constant is 1.38×10−4 atm cu m/mole @ 25°C.;
Food fumigants
In 1941~1942, the German Degesch Gesellsch company recommended to use acrylonitrile as a food fumigant.
Toxicity: acrylonitrile is of great toxicity to human with comparable toxicity as hydrocyanic acid. Acrylonitrile is highly toxic to insects, and is the most toxic in the main fumigant for controlling various stored grain pests.
Acrylonitrile is used alone or in combination with carbon tetrachloride and has no effect on the germination of many vegetables, grains and flower seeds, but has some damage to maize seeds. The mixture of acrylonitrile and carbon tetrachloride can be used to control the vast majority of stored cereals pests. The results showed that acrylonitrile and carbon tetrachloride, when formulated into mixture in a ratio of 1:1, can be used to control the Phthorimaea operculella Zell occurring in potato under storage without damaging the tubers.
Usage method: Because acrylonitrile and carbon tetrachloride are of high boiling point, upon atmospheric fumigation, in order to be quickly evaporated, it was developed of a simple method which uses cotton cord core to pass through the shallow iron disk bottom. During the beginning of the fumigation, inject a liquid fumigant into the dish and then blow the air through the fan to the cotton core until the evaporation is complete.;
Uses
Acrylonitrile is primarily used in the manufacture of acrylic and modacrylic fibers. It is also used as a raw material in the manufacture of plastics (acrylonitrile-butadiene-styrene and styrene-acrylonitrile resins), adiponitrile, acrylamide, and nitrile rubbers and barrier resins. A mixture of acrylonitrile and carbon tetrachloride was used as a pesticide in the past; however, all pesticide uses have stopped. Acrylonitrile is a commercially important industrial chemical that has been used extensively since 1940s with the rapid expansion of the petrochemical industry.
The production of ABS and SAN resins consumes the second largest quantity of acrylonitrile. The ABS resins are produced by grafting acrylonitrile and styrene onto polybutadiene or a styrene–butadiene copolymer and contain about 25 wt% acrylonitrile. These products are used to make components for automotive and recreational vehicles, pipe fittings, and appliances. The SAN resins are styrene–acrylonitrile copolymers containing 25–30 wt% of acrylonitrile. The superior clarity of SAN resin allows it to be used in automobile instrument panels, for instrument lenses and for houseware items (Langvardt, 1985; Brazdil, 1991).;

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