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)
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| 605368 | |
| ChemSpider | |
| ECHA InfoCard | Lua error in Module:Wikidata at line 880: attempt to index field 'wikibase' (a nil value). Lua error in Module:Wikidata at line 880: attempt to index field 'wikibase' (a nil value).Lua error in Module:EditAtWikidata at line 29: attempt to index field 'wikibase' (a nil value). |
| EC Number |
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| E number | Lua error in Module:Wikidata at line 880: attempt to index field 'wikibase' (a nil value). |
PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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| 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] |
Refractive index (nD)
|
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): | |
LD50 (median dose)
|
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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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
[edit | edit source]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
[edit | edit source]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
[edit | edit source]- Acyloin, the simplest secondary α-hydroxy ketone.
References
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- ^ a b c d Sigma-Aldrich Co., Hydroxyacetone. Retrieved on 2 July 2015.
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External links
[edit | edit source]- Error creating thumbnail: File missing Media related to Lua error in Module:Commons_link at line 62: attempt to index field 'wikibase' (a nil value). at Wikimedia Commons
