Chloroacetone is a

chemical compound A chemical compound is a chemical substance composed of many identical molecules (or molecular entities) containing atoms from more than one chemical element held together by chemical bonds. A molecule consisting of atoms of only one ele ...

with the formula . 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 Tear gas, also known as a lachrymator agent or lachrymator (), sometimes colloquially known as "mace" after the early commercial aerosol, is a chemical weapon that stimulates the nerves of the lacrimal gland in the eye to produce tears. In ...

World War I World War I (28 July 1914 11 November 1918), often abbreviated as WWI, was List of wars and anthropogenic disasters by death toll, one of the deadliest global conflicts in history. Belligerents included much of Europe, the Russian Empire, ...

Synthesis

Chloroacetone may be synthesized from the reaction between

chlorine Chlorine is a chemical element with the symbol Cl and atomic number 17. The second-lightest of the halogens, it appears between fluorine and bromine in the periodic table and its properties are mostly intermediate between them. Chlorine is ...

and diketene, or by the chlorination of

acetone Acetone (2-propanone or dimethyl ketone), is an organic compound with the formula . It is the simplest and smallest ketone (). It is a colorless, highly volatile and flammable liquid with a characteristic pungent odour. Acetone is miscible wi ...

Applications

Chloroacetone is used to make dye couplers for colour

photography Photography is the visual art, art, application, and practice of creating durable images by recording light, either electronically by means of an image sensor, or chemically by means of a light-sensitive material such as photographic film. It i ...

, and is an intermediate in chemical manufacturing. It is also used in the Feist-Benary synthesis of furans. *Reaction of phenoxide with chloroacetone gives phenoxyacetone, which is used to make a wide variety of different pharmaceuticals. A catalytic amount of potassium iodide is also necessary to facilitate a Finkelstein reaction.

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 The United States Department of Transportation (USDOT or DOT) is one of the executive departments of the U.S. federal government. It is headed by the secretary of transportation, who reports directly to the President of the United States an ...

. Stabilized chloroacetone is in hazard class 6.1 (Poison Inhalation Hazard). Its

UN number A UN number (United Nations number) is a four-digit number that identifies hazardous materials, and articles (such as explosives, flammable liquids, oxidizers, toxic liquids, etc.) in the framework of international trade and transport. Some ha ...

is 1695.

References

External links