Chloroacetone


Chloroacetone is a chemical compound with the formula 3CCH2. At STP it is a colourless liquid with a pungent odour. On exposure to light, it turns to a dark yellow-amber colour. 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 used to make dye couplers for colour photography, and is an intermediate in chemical manufacturing. It is also used in the Feist-Benary synthesis of furans.
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, which is removed on subsequent distillation.

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. Its UN number is 1695.