Hydroxyacetone

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).

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.

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

  1. ^ a b Nodzu, Ryuzaburo (1935). "On the Action of Phosphate Upon Hexoses. I. The Formation of Acetol From Glucose in Acidic Solution of Potassium Phosphate". Bull. Chem. Soc. Jpn. 10 (3): 122–130. doi:10.1246/bcsj.10.122.
  2. ^ a b c d Sigma-Aldrich Co., Hydroxyacetone. Retrieved on 2 July 2015.
  3. ^ Smyth, H. F. Jr; Carpenter, C. P. (January 1948). "Further experience with the range finding test in the industrial toxicology laboratory". The Journal of Industrial Hygiene and Toxicology. 30 (1): 63–8. PMID 18895731.
  4. ^ Carl J. Sullivan, Anja Kuenz, Klaus‐Dieter Vorlop (2018). "Propanediols". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a22_163.pub2. ISBN 978-3527306732.{{cite encyclopedia}}: CS1 maint: multiple names: authors list (link)
  5. ^ Levene, P. A.; Walti, A. (1930). "Acetol". Org. Synth. 10: 1. doi:10.15227/orgsyn.010.0001.
  6. ^ Nursten, Harry E. (1998). "The Mechanism of Formation of 3-Methylcyclopent-2-en-2-olone". In O'Brien, J.; Nursten, H. E.; Crabbe, M. J.; Ames, J. M. (eds.). The Maillard Reaction in Foods and Medicine. Elsevier. pp. 65–68. ISBN 9781845698447.