acrylonitrile

Acrylonitrile
IUPAC name	Ethenylnitrile
Systematic name	2-propenenitrile
Other names	cyanoethene, vinylcyanide
Identifiers
CAS number	107-13-1 Y
PubChem	7855
SMILES	N#C\C=C
InChI	1/C3H3N/c1-2-3-4/h2H,1H2
InChI key	NLHHRLWOUZZQLW-UHFFFAOYAG
ChemSpider ID	7567
Properties
Molecular formula	C3H3N
Molar mass	53.06 g mol−1
Appearance	Colourless liquid
Density	0.81 g/cm3
Melting point	-84 °C(189 K)
Boiling point	77 °C (350 K)
Solubility in water	7 g/100 mL at 20 °C
Hazards
MSDS	ICSC 0092
Main hazards	flammable, reactive, toxic
Related compounds
Related compounds	acrylic acid, acrolein
Y (what is this?)  (verify) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Acrylonitrile is the chemical compound with the formula CH₂CHCN. This pungent-smelling colorless liquid often appears yellow due to impurities. It is an important monomer for the manufacture of useful plastics. In terms of its molecular structure, it consists of a vinyl group linked to a nitrile.

Uses

Acrylonitrile is used principally as a monomer in the manufacture of synthetic polymers, especially polyacrylonitrile which comprises acrylic fibers. Acrylic fibers are, among other uses, precursor for well-known carbon-fiber. It is also a component of synthetic rubber. Dimerization of acrylonitrile affords adiponitrile, used in the synthesis of certain Nylons. Small amounts are also used as a fumigant. Acrylonitrile and derivatives such as 2-chloro-acrylonitrile are dienophiles in Diels-Alder reactions. Acrylonitrile is also a precursor in the industrial manufacture of acrylamide and acrylic acid.

Production

Acrylonitrile is probably the nitrile manufactured on the largest scale. Most industrial acrylonitrile is produced through the Sohio process, the catalytic ammoxidation of propylene:

2CH₃-CH=CH₂ + 2NH₃ + 3O₂ → 2CH₂=CH-C≡N + 6H₂O

World annual production in 2001 was 4 million tonnes and in 2005 6 million tonnes, with just under half of that coming from the United States. A significant byproduct is acetonitrile; this process is the main source of acetonitrile.

In 1996 the Sohio acrylonitrile process was designated an ACS National Historical Chemical Landmark in recognition of the innovative single-step method of production that made acrylonitrile available for chemical manufacturing worldwide.[1]

Health Effects

Acrylonitrile is highly flammable and toxic. It undergoes explosive polymerization. The burning material releases fumes of hydrogen cyanide and oxides of nitrogen. The International Agency for Research on Cancer (IARC) concluded that there is inadequate evidence in humans for the carcinogenicity of acrylonitrile, but classified it as a Class 2B carcinogen (possibly carcinogenic). ^[1] Acrylonitrile increases cancer in high dose tests in male and female rats and mice. ^[2]

References

1. ^ IARC evaluation of Acrylonitrile
2. ^ Animal Test Result on Acrylonitrile in the Carcinogenic Potency Database

External links

• National Pollutant Inventory - Acrylonitrile
• Comparing Possible Cancer Hazards from Human Exposures to Rodent Carcinogens