Chloroacetone is a liquid, a chemical compound with the formula . Regulated for its potential as a tear gas, it is primarily a chemical intermediate in commerce.
Properties At STP it is a colorless liquid with a pungent odor. On exposure to light, it turns to a dark yellow-amber color. It was used as a tear gas in World War I.
Synthesis Chloroacetone may be synthesized from the reaction between chlorine and diketene, or by the chlorination of acetone.
Applications Chloroacetone is primarily an intermediate in chemical manufacture. In the early 2000s, it was used to make dye couplers for colour film photography. In the pharmaceutical industry, it is a precursor to phenoxyacetone.
It is also used in the Feist-Benary synthesis of furans:
Purification Chloroacetone purchased from commercial suppliers contains 5% impurities including mesityl oxide, which is not removed by distillation. Mesityl oxide can be oxidized using acidified KMnO4 to form a diol (followed by separation with ether), which is removed on subsequent distillation.Phys. Chem. Chem. Phys., 2000,2, 237-245
Transportation regulations Transportation of unstabilized chloroacetone has been banned in the United States by the US Department of Transportation. Stabilized chloroacetone is in hazard class 6.1 (Poison Inhalation Hazard). Its UN number is 1695.
See also Bromoacetone Dichloroacetone Fluoroacetone Hexachloroacetone Use of poison gas in World War I
References
External links The Halogenation of Carbonyls