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Acrylonitrile

Unsaturated nitrile compounds Usage History Chemical properties Food fumigants The main purpose and role of acrylonitrile Chemical properties Uses Production method
Acrylonitrile
Acrylonitrile structure
CAS No.
107-13-1
Chemical Name:
Acrylonitrile
Synonyms
VCN;ent54;tl314;ENT 54;TL 314;Ventox;Acritet;Acrylon;CH2CHCN;NSC 6362
CBNumber:
CB8764818
Molecular Formula:
C3H3N
Formula Weight:
53.06
MOL File:
107-13-1.mol

Acrylonitrile Properties

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.)
Flash point:
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)
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)
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.
CAS DataBase Reference
107-13-1(CAS DataBase Reference)
NIST Chemistry Reference
2-Propenenitrile(107-13-1)
EPA Substance Registry System
2-Propenenitrile(107-13-1)
SAFETY
  • Risk and Safety Statements
  • Hazard and Precautionary Statements (GHS)
  • NFPA
Hazard Codes  F,T,N,Xn
Risk Statements  45-11-23/24/25-37/38-41-43-51/53-39/23/24/25-62-63
Safety Statements  53-9-16-45-61-36/37
RIDADR  UN 1093 3/PG 1
WGK Germany  3
RTECS  AT5250000
8
Autoignition Temperature 481 °C
TSCA  Yes
HazardClass  3
PackingGroup  I
HS Code  29261000
Hazardous Substances Data 107-13-1(Hazardous Substances Data)
Toxicity LD50 orally in rats: 0.093 g/kg (Smyth, Carpenter)
Symbol(GHS):
Signal word: Danger
Hazard statements:
Code Hazard statements Hazard class Category Signal word Pictogram P-Codes
H225 Highly Flammable liquid and vapour Flammable liquids Category 2 Danger P210,P233, P240, P241, P242, P243,P280, P303+ P361+P353, P370+P378,P403+P235, P501
H301 Toxic if swalloed Acute toxicity,oral Category 3 Danger P264, P270, P301+P310, P321, P330,P405, P501
H311 Toxic in contact with skin Acute toxicity,dermal Category 3 Danger P280, P302+P352, P312, P322, P361,P363, P405, P501
H315 Causes skin irritation Skin corrosion/irritation Category 2 Warning P264, P280, P302+P352, P321,P332+P313, P362
H317 May cause an allergic skin reaction Sensitisation, Skin Category 1 Warning P261, P272, P280, P302+P352,P333+P313, P321, P363, P501
H318 Causes serious eye damage Serious eye damage/eye irritation Category 1 Danger P280, P305+P351+P338, P310
H331 Toxic if inhaled Acute toxicity,inhalation Category 3 Danger P261, P271, P304+P340, P311, P321,P403+P233, P405, P501
H335 May cause respiratory irritation Specific target organ toxicity, single exposure;Respiratory tract irritation Category 3 Warning
H350 May cause cancer Carcinogenicity Category 1A, 1B Danger
H361 Suspected of damaging fertility or the unborn child Reproductive toxicity Category 2 Warning P201, P202, P281, P308+P313, P405,P501
H370 Causes damage to organs Specific target organ toxicity, single exposure Category 1 Danger P260, P264, P270, P307+P311, P321,P405, P501
H411 Toxic to aquatic life with long lasting effects Hazardous to the aquatic environment, long-term hazard Category 2
Precautionary statements:
P201 Obtain special instructions before use.
P210 Keep away from heat/sparks/open flames/hot surfaces. — No smoking.
P260 Do not breathe dust/fume/gas/mist/vapours/spray.
P261 Avoid breathing dust/fume/gas/mist/vapours/spray.
P273 Avoid release to the environment.
P280 Wear protective gloves/protective clothing/eye protection/face protection.
P311 Call a POISON CENTER or doctor/physician.
P301+P310 IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P303+P361+P353 IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
P308+P313 IF exposed or concerned: Get medical advice/attention.
P405 Store locked up.
P403+P233 Store in a well-ventilated place. Keep container tightly closed.

NFPA 704

Diamond Hazard Value Description
3
4 2
Health   4 Very short exposure could cause death or major residual injury (e.g. hydrogen cyanide, phosgene, methyl isocyanate, hydrofluoric acid)
Flammability   3 Liquids and solids (including finely divided suspended solids) that can be ignited under almost all ambient temperature conditions . Liquids having a flash point below 22.8 °C (73 °F) and having a boiling point at or above 37.8 °C (100 °F) or having a flash point between 22.8 and 37.8 °C (73 and 100 °F). (e.g. gasoline, acetone)
Instability   2 Undergoes violent chemical change at elevated temperatures and pressures, reacts violently with water, or may form explosive mixtures with water (e.g. white phosphorus, potassium, sodium)
Special  

(NFPA, 2010)

Acrylonitrile price More Price(14)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 110213 Acrylonitrile ≥99%, contains 35-45 ppm monomethyl ether hydroquinone as inhibitor 107-13-1 1l $45.1 2018-11-13 Buy
Sigma-Aldrich 110213 Acrylonitrile ≥99%, contains 35-45 ppm monomethyl ether hydroquinone as inhibitor 107-13-1 2l $59.2 2018-11-13 Buy
Alfa Aesar A13058 Acrylonitrile, 99+%, stab. with ca 40ppm 4-methoxyphenol 107-13-1 100ml $15.3 2018-11-13 Buy
Alfa Aesar A13058 Acrylonitrile, 99+%, stab. with ca 40ppm 4-methoxyphenol 107-13-1 500ml $24 2018-11-13 Buy
Sigma-Aldrich 110213 Acrylonitrile ≥99%, contains 35-45 ppm monomethyl ether hydroquinone as inhibitor 107-13-1 5ml $29.9 2018-11-13 Buy

Acrylonitrile Chemical Properties,Uses,Production

Unsaturated nitrile compounds

Acrylonitrile is also known as cyanoethylene, 2-acrylonitrile, vinyl nitrile, grain fumigants, Ventox, Acritet, being a kind of unsaturated nitrile compound. It was first synthesized by C. Moureu in 1893. Its molecular formula is C3H3N and structural formula is CH2 = CHCN. It appears as colorless flammable liquid, being volatile, explosive and flammable. It has slightly special smell with sweetness. The relative molecular mass is 53.06. The relative density is 0.8060. Melting point:-83.55 °C; Boiling point: 77.3 to 77.4°C, 64.7°C (66.661 103 Pa), 45.5°C (33.331 103 Pa), 3.6°C (13.331 103 Pa), 8.7°C (6.666 103 Pa). Flash point:-5 °C. Flash point: 0 °C. Refractive index: 1.3911. Viscosity: 0.34mPa • s (25 ℃). Soluble in water: 0 °C 7.2, 10 °C: 7.25, 20 °C: 7.35, 30 °C: 7.60, 40 °C: 7.80, 50 °C: 8.3, 60 °C: 9.0, 70 °C: 9.8, 80 °C: 10.8; It is soluble in acetone, ethanol, benzene, carbon tetrachloride, ethyl acetate, methanol, ethyl ether and so on.
It can form azeotropic mixture with water with the content of 88%, azeotropic point of 71 ℃; it can form azeotropic mixture with benzene with the content of 47%, azeotropic point of 73.3 ℃; it can form azeotropic mixture with carbon tetrachloride with the content of 21 %, azeotropic point of 66.2 ℃;
It can form azeotropic mixture with methanol with the content of 39%, azeotropic point 61.4 ℃. Its vapor and air can form an explosive mixture, with the explosive limit at 25 ℃ being 3.05%~17.0% (volume fraction). The molecular structure of Acrylonitrile contains double bonds and cyano bonds, being chemically active. Its double bonds can undergo self-polymerization and copolymerization with other compounds, diene addition, reduction, halogenation and reaction with nucleophilic agents; the cyano group can undergo hydration, hydrolysis, alcoholysis and condensation. This product is easy to form a white powder upon polymerization. This product has toxic vapor with a large number of inhalation being able to cause nausea, headache and other symptoms. It can also cause poisoning upon invading the skin. After poisoning, the use of drugs for hydrocyanic acid detoxification such as amyl nitrite and sodium thiosulfate is often ineffective; indicating that it is not only the decomposition of hydrocyanic acid that is toxic, but also acrylonitrile itself is toxic! Mice intravenous LD50:15mg/kg, Rat oral LD50: 93mg/kg. The maximum allowable concentration of the workplace is 20 × 10-6. The antidote for this product includes sodium thiosulfate, L-cysteine and methionine.
The above information is edited by Tongtong from Chemicalbook.

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 has very active chemical nature with its molecule containing cyano, carbon-carbon double bond, being able to participate in a variety of reactions:

(1) Figure 1 shows the reaction of acrylonitrile.

(2) Figure 2 shows the reaction of acrylonitrile double bond.
(3) Cyanoethylation reaction: it can have reaction with alcohols, phenols, amines, ketones, aldehydes, nitromethane, diethyl malonate, introducing cyanoethyl group into the molecule. The general formula is as follows: R-H + CH2 = CHCN → R-CH2CH2CN.
(4) Polymerization: acrylonitrile is prone to have polymerization, being a monomer of polyacrylonitrile. It can copolymerize with vinyl chloride to generate dinell fiber, and copolymerize with butadiene to produce butadiene-acrylonitrile rubber. Acrylonitrile is the raw materials of polyacrylamide and polypropylene.

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.
Polyacrylonitrile
Polyacrylonitrile is also known as "acrylic." being a copolymer originated from the copolymerization of acrylonitrile, methyl acrylate and itaconic acid. Its chemical formula is (CH2 = CH-CN) n, being a white powder with the proportion of 1.14 to 1.16. It is almost insoluble in water, fat, weak acid, weak base as well as saliva, gastric liquid. It is soluble in the aqueous solution of dimethyl formamide, dimethyl sulfoxide and inorganic salts (ZnCl2, NaSCN, etc.) and nitric acid. Polyacrylonitrile suitable for making fiber has a molecular weight between 2.05 million and 2.08 million and can be softened and decomposed at 230 °C.
Features: excellent performance, soft, light, warm, and wool close to the "synthetic wool," said. It has high elastic modulus, excellent shape retention, excellent light fastness and radiation resistance, being able to be used in a short time at 180~200 ℃. It has high acid and solvent stability but has poor abrasion resistance and fatigue resistance. It is widely used to replace wool and can be blended with wool, cotton and viscose fiber, making wool fabric, cotton fabric, knitted fabrics, carpets, etc., being especially suitable for outdoor fabric system, and taking advantage of its thermal flexibility to make soft thermal bulk yarn. After the polyacrylonitrile is subject to heat treatment to produce semiconductor fiber, followed by further undergoing high-temperature treatment at 1,000-1,500 °C can lead to high-modulus carbon fiber for producing ablative composite material for artificial satellite or missile shell.
Polyacrylonitrile belongs to low toxicity class. For rats, neither a single oral dose of 2,000~3,000mg/kg nor the inhalation of a concentration of 2,500~3,000 mg /m3 can cause poisoning. It has accumulation property. Polyacrylonitrile fiber is relatively coarse, hard and brittle easy to be broken, similar to glass fiber, being able to produce mechanical stimulation to the skin and mucous membranes, so the spinning worker in contact with polyacrylonitrile fiber can get skin itching and rash. Skin patch test has found no chemical stimulation and sensitization. PRECAUTIONS: Reduce the oligomeric dust through revolutionize the technology; sealing; apply extraction ventilation, and enhance personal protection. Supply iodine and vitamin C-rich foods.

The main purpose and role of acrylonitrile

(1) acrylonitrile can be used for the manufacture of acrylonitrile fiber and carbon fiber; used in the production of sodium L-glutamate (i.e. MSG), acrylate (raw materials of organic synthesis and paint), methine glutaronitrile (ABS modifier, the raw material of 2-methyl-1,5-diamine), α, α-dichloropropionic acid and α, α, β-trichloropropionic acid (used as the raw materials of herbicide), succinonitrile (the raw materials of succinate and 1,2-Butanediol), pimelic acid (for the production of plasticizers, plant growth regulators and pharmaceutical raw materials) and other derivatives.
(2) Important raw materials of organic synthesis for the production of dyes, antioxidants, surfactants and so on.
(3) monomers for synthesis, mainly used in the manufacture of synthetic fibers (acrylic); copolymerization with butadiene can produce oil, cold-resistant nitrile rubber; copolymerization with butadiene and styrene can produce three-way engineering plastics (ABS resin); control of acrylonitrile hydrolysis conditions, under the action of copper as the catalyst, we can obtain acrylamide; after polymerization of acrylamide, we can obtain polyacrylamide, which is an important industrial raw materials.
(4) Acrylonitrile can undergo full hydrolysis under the action sulfuric acid, being able to lead to acrylic acid; electrolytic hydrogenation can obtain adiponitrile, and used for further preparation of hexamethylene diamine (nylon 66 raw materials); for pesticides (livestock anthelmintic) Pharmaceutical raw materials; for grain fumigants.
(5) Acrylonitrile is an excellent aprotic polar solvent.

Chemical properties

It appears as colorless volatile liquid with sweet taste and being slightly foul. It is soluble in acetone, benzene, carbon tetrachloride, ether, ethanol and other organic solvents. Slightly soluble in water

Uses

1.   It can be used for the synthesis of polyacrylonitrile, nylon 66, acrylonitrile-butadiene rubber, ABS resin, polyacrylamide, acrylic esters, also used as a grain smoked agent
2.  Acrylonitrile is the intermediate of fungicide bromothalonil, Propamocarb, Pesticide Chlorpyrifos and the intermediate of insecticidal bisultap, cartap. It can also be prepared for the production of methyl chrysanthemum pyrethroid, being also the intermediate of the insecticides chlorfenapyr.
3.   Acrylonitrile is an important monomer for synthetic fibers, synthetic rubbers and synthetic resins. Acrylonitrile is made from acrylic fiber (acrylic) with its performance being quite similar to wool, also called (synthetic wool). The copolymerization of acrylonitrile and butadiene can lead to nitrile rubber, having excellent oil resistance, cold resistance, wear resistance, and electrical insulation properties, and being stable under the action of most chemical solvents, sunlight and heat. Copolymerization of acrylonitrile and butadiene, styrene can lead to ABS resin with light property, cold-resistant, good impact resistance and so on. Acrylonitrile hydrolysis can lead to acrylamide and acrylic acid and its esters. They are important organic chemical raw materials, acrylonitrile can also be made of adiponitrile through electrolytic hydrogenation coupling system; from adiponitrile hydrogenation, and we can also obtain hexamethylenediamine which is the raw materials of nylon 6. It can be used to make water repellent and adhesive, also used in other organic synthesis and pharmaceutical industry, and as a cereal fumigant. In addition, the product is also a non-proton polar solvent.
4.  t can be used as a standard substance for chromatographic analysis. It is also used for the manufacture of rubber, plastics, organic synthesis and pesticides.
5.   For calibration of instruments and devices; evaluation methods; work standards; quality assurance/quality control;

Production method

1. Cyanide ethanol method: Ethylene oxide is reacted with hydrogen cyanide in the presence of water and trimethylamine to generate cyanoethanol, and then take magnesium carbonate as catalyst in 200-280 °C for dehydration to obtain acrylonitrile with a yield of about 75%. The acrylonitrile produced with this method has high purity. However, the toxicity of hydrocyanic acid is high with the cost being high as well.
2 Acetylene; acetylene is reacted with hydrocyanic acid under 80-90 °C under the catalysis of cuprous chloride-potassium chloride-sodium chloride dilute hydrochloric acid solution to obtain acrylonitrile. This method is simple with good yield which can be up to 97% if calculated on hydrogen Cyanic acid. But there are many side effects with the product being more difficult to refine and the toxicity being also large. Moreover, the price of acetylene raw material is higher than propylene, being lagged behind the ammoxidation of propylene in the technical and economic aspects.
Before 1960, this method is the major way of production of acrylonitrile around the world.
3. Ammonia-ammoxidation method; take propylene, ammonia, air and water as raw materials, add them into the ebullated bed or fixed-bed reactor according to a certain ratio; under the action of the phosphorus molybdenum bismuth or antimony iron-based catalyst using silica gel as the carrier and 400-500 ℃ as well as normal pressure, they will react to form acrylonitrile.
And then through the neutralization tower, use dilute sulfuric acid to remove unreacted ammonia, and then absorb acrylonitrile gas using water by the absorption tower to form aqueous solution. The aqueous solution is sent through the extraction tower to separate out the acetonitrile. Remove the hydrogen cyanide in the dehydrocyanic acid tower, further go through dehydration and rectification to derive acrylonitrile products with the one-way yield of up to 75%. The by-products include acetonitrile, hydrocyanic acid and ammonium sulfate. This method is of the most industrial production value at present.
Its preparation method mainly uses the propylene ammoxidation method; take the propylene, the ammonia and the oxygen in the air as the raw material; carry out the reaction in the presence of catalyst; the catalyst mainly consists of the phosphorus, molybdenum, bismuth compound with the mole ratio of propylene, ammonia and air being (1 to 1.2): (1.8 to 2.3); the reaction temperature is 400 to 500 ℃, the reaction pressure is normal pressure, and the reactor is a fluidized bed. The reaction equation:
CH2 = CH2-CH3 + NH3 + 3/2O2 → CH2 = CH-CN + 3H2O
The reaction yield of acrylonitrile is 60% to 75%.

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.

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.

Chemical Properties

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

Chemical Properties

clear liquid

Chemical Properties

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.

Uses

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.

Uses

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.

Uses

Grain fumigant.

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).

Definition

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

Definition

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

Air & Water Reactions

Highly flammable. Soluble in water.

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].

Health Hazard

Acrylonitrile 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).

Health Hazard

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.

Health Hazard

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.

Health Hazard

Two cases of death following acute acrylonitrile exposure are known (Grunske 1949). Both involved children, one treated with acrylonitrile for scalp lice, the second sleeping in a room fumigated with acrylonitrile.
Industry has taken extreme care to minimize the human occupational exposure, including the use of enclosed processing and delivery systems and the wearing of special suits, gloves, boots, and respirators by workers cleaning out reactors (Mallette 1943; Wilson 1944). However, during World War II some workmen were exposed during the handling of acrylonitrile (Wilson and McCormick 1949). All exposed individuals complained of nasal irritation and an ‘oppressive feeling’ in the upper respiratory passages. Other signs and symptoms included nausea, vomiting, weakness, headaches, fatigue, and diarrhea. Several developed jaundice, a low-grade anemia, and leukocytosis. Contact of the skin with acrylonitrile causes erythema, swelling, blisters, and itching (Dudley and Neal 1942). Khromov (1974) found dermatitis, eczema and urticaria to be common symptomatology in acrylonitrile workers.
A Japanese epidemiological study of 576 acrylonitrile workers concluded that increasing duration of exposure to acrylonitrile coincided with increases in the incidence of both subjective complaints and abnormal liver function values (Sakurai and Kusimoto 1972; Sakurai et al 1978). In a Yugoslavian study, examinations of 20 workers at an acrylic fiber plant (with acrylonitrile air conditions ranging from 3 to 20 mg/m3 or 1.5 to 9 p.p.m.) showed an abnormally large proportion of the workers with high irritability, alcohol intolerance, headaches,neurasthenic syndrome, poor appetite, and fatigue (Orusev and Popovski 1973).
In the U.S.A. the threshold limit value for acrylonitrile has remained, until recently, at the 20 p.p.m. (43.5 mg/m3) level proposed in 1945 (Schaffer 1975). In contrast, the maximum allowable level in the U.S.S.R. was set at 0.2 p.p.m. (0.4 mg/m3) (Fassett 1963). The emergency standard level for industrial exposure to acrylonitrile in the U.S.A. was set in January 1978 by OSHA at 2 p.p.m. averaged over an 8 h period. In 1975, Dow Chemical Company and other American manufacturers concluded that, based on their experience, no liver dysfunction or chronic illness of any kind could be linked to occupational exposure to acrylonitrile (Schaffer 1975).

Fire Hazard

Flash Point (°F): 30 ℃; 31 ℃; Flammable Limits in Air (%): 3.05-17.0; Fire Extinguishing Agents: Dry chemical, alcohol foam, carbon dioxide; Fire Extinguishing Agents Not To Be Used: Water or foam may cause frothing; Special Hazards of Combustion Products: When heated or burned, ACN may evolve toxic hydrogen cyanide gas and oxides of nitrogen; Behavior in Fire: Vapor is heavier than air and may travel a considerable distance to a source of ignition and flash back. May polymerize and explode; Ignition Temperature (°F): 898; Electrical Hazard: Class I, Group D; Burning Rate: Data not available.

Fire Hazard

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.

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 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.

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).

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.

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.

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).

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.

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.

Shipping

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.]

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.

Acrylonitrile Preparation Products And Raw materials

Raw materials

Preparation Products


Acrylonitrile Suppliers

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Acrylonitrile Spectrum


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