Chloroacetone

Chloroacetone is a chemical compound with the formula CH3COCH2Cl. At STP it is a colourless liquid with a pungent odour.[3] On exposure to light, it turns to a dark yellow-amber colour.[4] It was used as a tear gas in World War I.[5]

Chloroacetone
Names
IUPAC name
Chloropropanone
Other names
Acetonyl chloride, chloropropanone, 1-chloro-2-propanone, monochloroacetone, 1-chloro-2-ketopropane, 1-chloro-2-oxypropane
UN 1695
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.001.056
EC Number
  • 201-161-1
RTECS number
  • UC0700000
UNII
Properties
C3H5ClO
Molar mass 92.52 g·mol−1
Appearance Colorless liquid, oxidizes to amber
Density 1.123 g/cm3
Melting point −44.5 °C (−48.1 °F; 228.7 K)
Boiling point 119 °C (246 °F; 392 K)
10 g/100 mL at 20 °C
Solubility miscible with alcohol, ether, chloroform
Vapor pressure 1.5 kPa
-50.9·10−6 cm3/mol
2.36
Hazards
Flash point 35 °C (95 °F; 308 K)
610 °C (1,130 °F; 883 K)
Explosive limits 3.4% - ?[1]
Lethal dose or concentration (LD, LC):
100 mg/kg (rats, oral)[2]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

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.[2] It is also used in the Feist-Benary synthesis of furans.[6]

  • Reaction of phenoxide with chloroacetone gives phenoxyacetone,[7] 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.[8]

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.

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See also

References
  1. "ICSC:NENG0760 International Chemical Safety Cards (WHO/IPCS/ILO) CDC/NIOSH". Center for Disease Control. 2006-10-11. Retrieved 2009-04-17.
  2. Hathaway, Gloria J.; Proctor, Nick H. (2004). Proctor and Hughes' Chemical Hazards of the Workplace (5 ed.). Wiley-Interscience. pp. 143–144. ISBN 978-0-471-26883-3. Retrieved 2009-04-16.
  3. "Occupational Safety and Health Guideline for Chloroacetone". U.S. Department of Labor - Occupational Safety & Health Administration. Archived from the original on 2013-05-03. Retrieved 2008-06-06. External link in |publisher= (help)
  4. "CHLOROACETONE". International Programme on Chemical Safety. Retrieved 2008-06-06. External link in |publisher= (help)
  5. Haber, Ludwig Fritz (1986). The Poisonous Cloud: Chemical Warfare in the First World War. Oxford University press. ISBN 0-19-858142-4.
  6. Li, Jie-Jack; Corey, E. J. (2004). Name Reactions in Heterocyclic Chemistry. Wiley-Interscience. p. 160. ISBN 978-0-471-30215-5. Retrieved 2009-04-16.
  7. Hurd, Charles D.; Perletz, Percy (1946). "Aryloxyacetones1". Journal of the American Chemical Society. 68 (1): 38–40. doi:10.1021/ja01205a012. ISSN 0002-7863.
  8. Phys. Chem. Chem. Phys., 2000,2, 237-245
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