hydroxyacetone
{{Chembox
| ImageFile = Acetols.svg
| ImageSize = 150px
| ImageAlt =
| PIN = 1-Hydroxyacetone
| SystematicName = 1-Hydroxypropan-2-one
| OtherNames = 1-Hydroxy-2-propanone
Acetomethyl alcohol
Acetol
| Section1 = {{Chembox Identifiers
| CASNo = 116-09-6
| PubChem = 8299
| EC_number = 204-124-8
| Beilstein = 605368
| ChemSpiderID = 21106125
| UNII = 7I7YM0835W
| SMILES = CC(=O)CO
| InChI = 1S/C3H6O2/c1-3(5)2-4/h4H,2H2,1H3
| InChIKey = XLSMFKSTNGKWQX-UHFFFAOYSA-N
}}
| Section2 = {{Chembox Properties
| C=3 | H=6 | O=2
| Appearance = Colorless liquid
| Odour = Sweet
| Density = 1.059 g/cm3{{cite journal|last1=Nodzu|first1=Ryuzaburo|title=On the Action of Phosphate Upon Hexoses. I. The Formation of Acetol From Glucose in Acidic Solution of Potassium Phosphate|journal=Bull. Chem. Soc. Jpn.|date=1935|volume=10|issue=3|pages=122–130|doi=10.1246/bcsj.10.122|doi-access=free}}
| MeltingPtC = −17
| BoilingPtC = 145–146
| VaporPressure = 7.5 hPa at 20 °C
| Solubility =
}}
| Section3 = {{Chembox Hazards
| MainHazards =
| HPhrases = {{H-phrases|226}}{{Sigma-Aldrich|id=W446207|name=Hydroxyacetone|accessdate=2 July 2015}}
| FlashPt = 56 °C (closed cup)
| AutoignitionPt =
| ExploLimits = Upper limit: 14.9%(V)
Lower limit: 3%(V)
}}
}}
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.{{Ullmann|title=Propanediols|author=Carl J. Sullivan, Anja Kuenz, Klaus‐Dieter Vorlop|year=2018|doi=10.1002/14356007.a22_163.pub2}}
Hydroxyacetone is commercially available, but it also may be synthesized on a laboratory scale by a substitution reaction on bromoacetone.{{cite journal|journal=Org. Synth.|last1= Levene|first1= P. A.|last2= Walti|first2= A. | title = Acetol | year = 1930 | volume = 10 | page = 1|doi=10.15227/orgsyn.010.0001}}
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.{{cite book |title= The Maillard Reaction in Foods and Medicine |editor1-first= J. |editor1-last= O'Brien |editor2-first= H. E. |editor2-last= Nursten |editor3-first= M. J. |editor3-last= Crabbe |editor4-first= J. M. |editor4-last= Ames |publisher= Elsevier |year= 1998 |isbn= 9781845698447 |chapter= The Mechanism of Formation of 3-Methylcyclopent-2-en-2-olone |first1= Harry E. |last1= Nursten |pages= 65–68 }} As such it finds some use as a flavoring.
See also
- Acyloin, the simplest secondary α-hydroxy ketone.
References
{{reflist}}
External links
- {{Commonscatinline}}