Acrylonitrile

From Free net encyclopedia

</table> Acrylonitrile (C H₂=C H-C≡N), is a pungent smelling, extremely flammable organic liquid. It is also known as cyanoethylene (cyanoethene) or vinyl cyanide. Its IUPAC name is 2-propene nitrile.

**Properties**
General
Image:Acrylonitrile-skeletal.png
Name	Acrylonitrile
Chemical formula	C₃H₃N
Appearance	Colourless to pale yellow liquid
Physical
Formula weight	53.06 amu
Melting point	189 K (-84 °C)
Boiling point	350 K (77 °C)
Density	0.8 ×10³ kg/m³
Solubility	7 g/100 mL at 20 °C
Thermochemistry
Δ_fH⁰_liquid	kJ/mol
S⁰_{liquid, 1 bar}	J/mol·K
Safety
Flammability	Extremely flammable and highly reactive. Gives off toxic fumes whilst burning.
Ingestion	Headache, excitement, fatigue, nausea, vomiting, stupor, and coma.
Inhalation	Headache, dizziness, unconsciousness and coma. High concentrations may be fatal.
Skin	Irritation. Can be absorbed through skin. Repeated exposures cause sensitization.
Eyes	Severe irritation, pain and blurred vision.
More info	Hazardous Chemical Database
SI units were used where possible. Unless otherwise stated, standard conditions were used. Disclaimer and references </font>

1 Uses
2 Production
3 Safety
4 External links

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Uses

Acrylonitrile is used principally as a precursor monomer in the manufacture of synthetic polymers, especially polyacrylonitrile, acrylic fibers, nylon, and synthetic rubber. Small amounts are also used as a fumigant. Acrylonitrile and derivatives such as 2-chloro-acrylonitrile are dienophiles in Diels-Alder reactions.

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Production

Most industrial acrylonitrile is produced through the Sohio process, the catalytic ammoxidation of propylene:

CH₃-CH=CH₂ + NH₃ + 1.5 O₂ → CH₂=CH-C≡N + 3 H₂O

World annual production in 2001 was 4 million tonnes, with just under half of that coming from the United States.

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Safety

Acrylonitrile is highly flammable, and can be easily ignited from a spark, or spontaneously on contact with certain oxidizers. Unless chemical stabilizers called "inhibitors" are added, it may also undergo explosive polymerization when heated, on contact with strong alkalis, or when exposed to ultraviolet light. The burning material releases fumes of hydrogen cyanide and oxides of nitrogen. Store in a well ventilated flammable material store away from incompatible materials, and avoid sparks.

The material is also toxic. Contact with skin or the eyes produces severe irritation. Inhalation or prolonged skin contact can produce confusion, unconsciousness, and death. Acrylonitrile is classified as a possible human carcinogen (IARC group 2B). Wear approved safety goggles, gloves and respirator during handling.

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