Chloroacetone

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Chloroacetone
Chloroacetone 2D skeletal.svg
Chloroacetone-3D-balls.png
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
78-95-5 YesY
ChEBI CHEBI:47220 YesY
ChemSpider 6323 YesY
EC number 201-161-1
Jmol-3D images Image
PubChem 6571
RTECS number UC0700000
UNII 60ZTR74268 YesY
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 in alcohol, ether, chloroform
Vapor pressure 1.5 kPa
Dipole moment 2.36
Hazards
Flash point 35 °C (95 °F; 308 K)
610 °C (1,130 °F; 883 K)
Explosive limits 3.4% - ?[1]
100 mg/kg (rats, oral)[2]
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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Infobox references

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]

Synthesis[edit]

Chloroacetone may be synthesized from the reaction between chlorine and diketene, or by the chlorination of acetone.

Applications[edit]

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]

FeistBenarysynthesis.gif

Purification[edit]

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[edit]

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[edit]

References[edit]

  1. ^ "ICSC:NENG0760 International Chemical Safety Cards (WHO/IPCS/ILO) CDC/NIOSH". Center for Disease Control. 2006-10-11. Retrieved 2009-04-17. 
  2. ^ a b 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. Retrieved 2008-06-06. 
  4. ^ "CHLOROACETONE". International Programme on Chemical Safety. Retrieved 2008-06-06. 
  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. ^ Phys. Chem. Chem. Phys., 2000,2, 237-245

External links[edit]