Hydroxyacetone

Chemical compound From Wikipedia, the free encyclopedia

Hydroxyacetone, also known as acetol, is the organic chemical with the formula CH3C(O)CH2OH. It consists of a primary alcohol substituent on acetone. It is an α-hydroxyketone, also called a ketol, and is the simplest hydroxy ketone structure. It is a colorless, distillable liquid.

Quick facts Names, Identifiers ...
Hydroxyacetone
Names
Preferred IUPAC name
1-Hydroxyacetone
Systematic IUPAC name
1-Hydroxypropan-2-one
Other names
1-Hydroxy-2-propanone
Acetomethyl alcohol
Acetol
Identifiers
3D model (JSmol)
605368
ChemSpider
ECHA InfoCard 100.003.750 Edit this at Wikidata
EC Number
  • 204-124-8
UNII
  • InChI=1S/C3H6O2/c1-3(5)2-4/h4H,2H2,1H3
    Key: XLSMFKSTNGKWQX-UHFFFAOYSA-N
  • CC(=O)CO
Properties
C3H6O2
Molar mass 74.079 g·mol−1
Appearance Colorless liquid
Odor Sweet
Density 1.059 g/cm3[1]
Melting point −17 °C (1 °F; 256 K)
Boiling point 145–146 °C (293–295 °F; 418–419 K)
Vapor pressure 7.5 hPa at 20 °C[2]
1.415[1]
Hazards
GHS labelling:
H226[2]
Flash point 56 °C (closed cup)[2]
Explosive limits Upper limit: 14.9%(V)
Lower limit: 3%(V)[2]
Lethal dose or concentration (LD, LC):
2200 mg/kg (rat, oral)[3]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Preparation

It is produced commercially by dehydration of glycerol.[4]

Hydroxyacetone is commercially available, but it also may be synthesized on a laboratory scale by a substitution reaction on bromoacetone.[5]

Reactions

It undergoes rapid polymerization, including forming a hemiacetal cyclic dimer. Under alkaline conditions, it undergoes a rapid aldol condensation.

Hydroxyacetone can be produced by degradation of various sugars. In foods, it is formed by the Maillard reaction. It reacts further to form other compounds with various aromas.[6] As such it finds some use as a flavoring.

See also

  • Acyloin, the simplest secondary α-hydroxy ketone.

References

External links

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