5942. Methacrylonitrile

Nomenclature

CAS number: 126-98-7
2-Methyl-2-propenenitrile; 2-cyano-1-propene; isobutenenitrile; isopropene cyanide; isopropenylnitrile; α-methylacrylonitrile.
C4H5N; mol wt 67.09.
C 71.61%, H 7.51%, N 20.88%.

Description and references

Prepd by vapor-phase catalytic oxidation of methallylamine: Peters et al., Ind. Eng. Chem. 40, 2046 (1948) DOI; US 2375016 (1945 to Shell); by the dehydration of methacrylamide: Kung, US 2373190 (1945 to Goodrich); from isopropylene oxide and ammonia: Spillane, Kayser, US 2557703 (1951 to Allied Chem.). Toxicity study: Smyth et al., Am. Ind. Hyg. Assoc. J. 23, 95 (1962) PubMed.

Chemical structure

Properties

Liquid. d420 0.8001; d430 0.7896. mp 35.8°. bp760 90.3°. nD20 1.4007; nD30 1.3954. Flash pt, open cup: 55°F (13°C). Viscosity (20°): 0.392 cP. Surface tension at 20°, 24.4 dynes/cm. Flammable; poisonous. Soly in water at 20° = 2.57 wt-%, at 50° = 2.69 wt-%. Soly of water in methacrylonitrile at 20° = 1.62 wt-%, at 50° = 2.83 wt-%. Misc with acetone, octane, toluene at 20-25°. LD50 orally in rats: 0.25 ml/kg (Smyth).

Caution

Potential symptoms of overexposure are irritation of eyes, skin; lacrimation. See NIOSH Pocket Guide to Chemical Hazards (DHHS/NIOSH 97-140, 1997) p 198.

Use

In prepn of homopolymers and copolymers; as an intermediate in the prepn of acids, amides, amines, esters, nitriles.