Hydroxyacetone
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| Names | |
|---|---|
| Preferred IUPAC name
1-Hydroxyacetone | |
| Systematic IUPAC name
1-Hydroxypropan-2-one | |
| Other names
1-Hydroxy-2-propanone
Acetomethyl alcohol Acetol | |
| Identifiers | |
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3D model (JSmol)
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| 605368 | |
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PubChem CID
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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 | |
| 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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Template:Chembox Footer/trackingTemplate:Short description
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
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- ^ a b Page Module:Citation/CS1/styles.css has no content.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.
- ^ a b c d Sigma-Aldrich Co., Hydroxyacetone. Retrieved on 2 July 2015.
- ^ Page Module:Citation/CS1/styles.css has no content.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.
- ^ Script error: No such module "Template wrapper".
- ^ Page Module:Citation/CS1/styles.css has no content.Levene, P. A.; Walti, A. (1930). "Acetol". Org. Synth. 10: 1. doi:10.15227/orgsyn.010.0001.
- ^ Page Module:Citation/CS1/styles.css has no content.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.
External links
- Page Template:Sister-inline/styles.css has no content.Script error: No such module "Sister project logo". Media related to Script error: No such module "Commons link". at Wikimedia Commons
