Acrylamide

Title: Acrylamide
CAS Registry Number: 79-06-1
CAS Name: 2-Propenamide
Molecular Formula: C3H5NO
Molecular Weight: 71.08
Percent Composition: C 50.69%, H 7.09%, N 19.71%, O 22.51%
Line Formula: CH2=CHCONH2
Literature 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.
Properties: Monomer, flake-like crystals from benzene. 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).
Melting point: mp 84.5°
Boiling point: bp2 87°; bp5 103°; bp25 125°
Density: d430 1.122
Toxicity data: LD50 i.p. in mice: 170 mg/kg (Peterson, Sheth)
Derivative Type: Polymer
Literature 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.
Acrylic Acid Acrylonitrile Actaplanins Actarit Actimid

Acrylamide
Acrylamide-2D-skeletal.png Acrylamide-MW-2000-3D-balls.png
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Identifiers
CAS number 79-06-1 YesY
PubChem 6579
ChemSpider 6331 YesY
UNII 20R035KLCI YesY
KEGG C01659 YesY
ChEBI CHEBI:28619 YesY
ChEMBL CHEMBL348107 YesY
Jmol-3D images Image 1
Image 2
Properties
Molecular formula C3H5NO
Molar mass 71.08 g mol−1
Density 1.13 g/cm3
Melting point 84.5 °C; 184.1 °F; 357.6 K
Boiling point – (polymerization)
Solubility in water 2.04 kg/L (25 °C)
Hazards
MSDS ICSC 0091
GHS pictograms GHS-pictogram-skull.svgGHS-pictogram-silhouete.svg[1]
GHS hazard statements H301, H312, H315, H317, H319, H332, H340, H350, H361, H372[1]
GHS precautionary statements P201, P280, P301+310, P305+351+338, P308+313[1]
EU Index 616-003-00-0
EU classification Toxic (T)
Carc. Cat. 2
Muta. Cat. 2
Repr. Cat. 3
R-phrases R45, R46, R20/21,
R25, R36/38, R43,
R48/23/24/25, R62
S-phrases S53, S45
NFPA 704
NFPA 704.svg
2
3
2
Autoignition temperature 424 °C; 795 °F; 697 K
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Acrylamide (or acrylic amide) is a chemical compound with the chemical formula C3H5NO. Its IUPAC name is prop-2-enamide. It is a white odourless crystalline solid, soluble in water, ethanol, ether, and chloroform. Acrylamide decomposes in the presence of acids, bases, oxidizing agents, iron, and iron salts. It decomposes non-thermally to form ammonia, and thermal decomposition produces carbon monoxide, carbon dioxide, and oxides of nitrogen.

Acrylamide is prepared on an industrial scale by the hydrolysis of acrylonitrile by nitrile hydratase.

Most acrylamide is used to synthesize polyacrylamides, which find many uses as water-soluble thickeners. These include use in wastewater treatment, gel electrophoresis (SDS-PAGE), papermaking, ore processing, tertiary oil recovery, and the manufacture of permanent press fabrics. Some acrylamide is used in the manufacture of dyes and the manufacture of other monomers.

Acrylamide is a known lethal neurotoxin (median lethal dose in rabbit = 150 mg/kg) and animal carcinogen. Its discovery in some cooked starchy foods in 2002 prompted concerns about the carcinogenicity of those foods.