2963. Diacetone Acrylamide

Nomenclature

CAS number: 2873-97-4
N-(1,1-Dimethyl-3-oxobutyl)-2-propenamide; N-(1,1-dimethyl-3-oxobutyl)acrylamide; N-[2-(2-methyl-4-oxopentyl)]acrylamide.
C9H15NO2; mol wt 169.22.
C 63.88%, H 8.93%, N 8.28%, O 18.91%.

Description and references

Highly reactive vinyl monomer. Prepd by the reaction of acrylonitrile with acetone in presence of conc sulfuric acid: Coleman et al., J. Polym. Sci. 3A, 1601 (1965); Coleman, US 3277056 (1966 to Lubrizol). Toxicity data: K. Hashimoto et al., Arch. Toxicol. 47, 179 (1981). Review: idem, “N-Oxoalkylacrylamides” in Encyclopedia of Polymer Science and Technology vol. 15, N. M. Bikales, Exec. Ed. (Wiley-Interscience, New York, 1971) pp 353-364.

Chemical structure

Properties

White crystalline solid, mp 57-58°. bp0.1-0.3 93-100°; bp8 120°. Hygroscopic. Has long shelf life; shows no polymerization on prolonged storage. A 50% neutral water soln is stable at pH 7.5-7.7 for up to six months. Similar to acrylic esters in polymerization behavior. Forms high mol wt polymers in bulk, solution, or emulsion. Esp suitable for electropolymerization. LD50 orally in mice: 7.7 mmol/kg (Hashimoto).

Use

In the manufacture of coatings, laminates, sealers, adhesives, lubricating oils.