66. Acetone

Nomenclature

CAS number: 67-64-1
2-Propanone; dimethylformaldehyde; dimethyl ketone; β-ketopropane; pyroacetic ether.
C3H6O; mol wt 58.08.
C 62.04%, H 10.41%, O 27.55%.

Description and references

Obtained by fermentation (by-product of butyl alcohol manufacture) or by chemical synthesis from isopropanol (as chief product); from cumene (by-product in phenol manufacture); from propane (by-product of oxidation-cracking); Faith, Keyes & Clark's Industrial Chemicals, F. A. Lowenheim, M. K. Moran, Eds. (Wiley-Interscience, New York, 4th ed., 1975) pp 21-25. Toxicity: Smyth et al., Ind. Hyg. J. 23, 95 (1962). Review: W. L. Howard in Kirk-Othmer Encyclopedia of Chemical Technology vol. 1 (Wiley-Interscience, New York, 5th ed., 2004) pp 160-177. Review of toxicology and human exposure: Toxicological Profile for Acetone (PB95-100095, 1994) 276 pp; of use in chemical ionization MS: S. Prabhakar, M. Vairamani, Mass Spectrom. Rev. 16, 259-281 (1997) DOI.

Chemical structure

Properties

Volatile liquid; characteristic odor; pungent, sweetish taste. Flammable. d2525 0.788. bp 56.5°. mp 94°. nD20 1.3591. Flash pt, closed cup: 0°F (18°C). Miscible with water, alcohol, DMF, chloroform, ether, most volatile oils. LD50 in rats: 10.7 ml/kg orally (Smyth).

Caution

Potential symptoms of overexposure are irritation of eyes, nose and throat; headache, dizziness, CNS depression; dermatitis. See NIOSH Pocket Guide to Chemical Hazards (DHHS/NIOSH 97-140, 1997) p 2.

Use

Solvent for fats, oils, waxes, resins, rubber, plastics, lacquers, varnishes, rubber cements. Versatile reagent in organic synthesis. Manuf of coatings, plastics, pharmaceuticals and cosmetics. In production of other solvents and intermediates including: methyl isobutyl ketone, mesityl oxide, acetic acid (ketene process), diacetone alcohol, bisphenol A, methyl methacrylate, explosives, rayon, photographic films, isoprene. In storing acetylene gas (takes up about 24 times its vol of the gas). In extraction of various principles from animal and plant substances; in paint and varnish removers; purifying paraffin; hardening and dehydrating tissues. Analytical uses in liquid chromatography; cleaning glassware. Pharmaceutic aid (solvent).