129. Acrylamide

Nomenclature

CAS number: 79-06-1
2-Propenamide.
C3H5NO; mol wt 71.08.
C 50.69%, H 7.09%, N 19.71%, O 22.51%.

Description and references

Prepd from acrylonitrile by treatment with H2SO4 or HCl: Bayer, Angew. Chem. 61, 240 (1949); Weisgerber, US 2535245 (1950 to Hercules). Reviews: Carpenter, Davis, J. Appl. Chem. 7, 671 (1957); C. E. Habermann in Kirk-Othmer Encyclopedia of Chemical Technology vol. 1 (John Wiley & Sons, New York, 4th ed., 1991) pp 251-266. Toxicity: R. E. Peterson, N. K. Sheth, Toxicol. Appl. Pharmacol. 33, 142 (1975). Review of carcinogenic risk: IARC Monographs 60, 389-433 (1994). Identification in cooked carbohydrate-rich foods: E. Tareke et al., J. Agric. Food Chem. 50, 4998 (2002). Proposed formation from asparagine, q.v., during cooking: D. S. Mottram et al., Nature 419, 448 (2002); R. H. Stadler et al., ibid. 449.

Chemical structure

Properties

Monomer, flake-like crystals from benzene. Poisonous. d430 1.122. mp 84.5°. bp2 87°; bp5 103°; bp25 125°. Solubilities in g/100 ml solvent at 30°: water 215.5; methanol 155; ethanol 86.2; acetone 63.1; ethyl acetate 12.6; chloroform 2.66; benzene 0.346; heptane 0.0068. The solid may be stored in a cool, dark place. Readily polymerizes at the mp or under uv light. Commercial solns of the monomer may be stabilized with hydroquinone, tert-butylpyrocatechol, N-phenyl-2-naphthylamine or other antioxidants. LD50 i.p. in mice: 170 mg/kg (Peterson, Sheth).

Derivative

Polymer.

Description and references

Various forms, sol and insol in water, are obtained by heating with various polymerization catalysts: C. E. Schildknecht, Vinyl and Related Polymers (Wiley, New York, 1952) pp 314-322; D. Lipp, J. Kozakiewicz in Kirk-Othmer Encyclopedia of Chemical Technology vol. 1 (John Wiley & Sons, New York, 4th ed., 1991) pp 266-287.

Caution

Potential symptoms of overexposure to the monomer are ataxia, numbness of limbs, paresthesia; muscle weakness; absence of deep tendon reflex; sweating of hands; fatigue, lethargy; irritation of eyes and skin; reproductive effects. See NIOSH Pocket Guide to Chemical Hazards (DHHS/NIOSH 97-140, 1997) p 6. Readily absorbed through intact skin from aqueous solutions. See Clinical Toxicology of Commercial Products, R. E. Gosselin et al., Eds. (Williams & Wilkins, Baltimore, 5th ed., 1984) Section II, p 409. This substance is reasonably anticipated to be a human carcinogen: Report on Carcinogens, Eleventh Edition (PB2005-104914, 2004) p III-4.

Use

Monomer as chemical intermediate in production of polyacrylamides; in synthesis of dyes; in copolymers for contact lenses; in construction of dam foundations, tunnels and sewers. Polymers as additives for water treatment, enhanced oil recovery, flocculants, papermaking aids, thickeners, soil conditioning agents, sewage and waste treatment, ore processing, permanent-press fabrics.