Chloroacetone Explained

Chloroacetone is a chemical compound with the formula . At STP it is a colorless liquid with a pungent odor.^[1] On exposure to light, it turns to a dark yellow-amber color.^[2] It was used as a tear gas in World War I.^[3]

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.^[4] It is also used in the Feist-Benary synthesis of furans.^[5]

• Reaction of phenoxide with chloroacetone gives phenoxyacetone,^[6] 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.^[7]

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

External links

• The Halogenation of Carbonyls

Notes and References

1. Web site: Occupational Safety and Health Guideline for Chloroacetone . 2008-06-06 . U.S. Department of Labor - Occupational Safety & Health Administration . https://web.archive.org/web/20130503155817/http://www.osha.gov/SLTC/healthguidelines/chloroacetone/recognition.html . 2013-05-03 . dead .
2. Web site: CHLOROACETONE . 2008-06-06 . International Programme on Chemical Safety.
3. Book: Haber, Ludwig Fritz . 1986 . The Poisonous Cloud: Chemical Warfare in the First World War . Oxford University Press . 0-19-858142-4 .
4. Book: Hathaway . Gloria J. . Proctor . Nick H. . 2004 . Proctor and Hughes' Chemical Hazards of the Workplace . 5 . Wiley-Interscience . 143–144 . 978-0-471-26883-3 . 2009-04-16.
5. Book: Li . Jie-Jack . Corey . E. J. . 2004 . Name Reactions in Heterocyclic Chemistry . Wiley-Interscience . 160 . 978-0-471-30215-5 . 2009-04-16.
6. Hurd. Charles D.. Perletz. Percy. Aryloxyacetones1. Journal of the American Chemical Society. 68. 1. 1946. 38–40. 0002-7863. 10.1021/ja01205a012.
7. Phys. Chem. Chem. Phys., 2000,2, 237-245