Hydroxyacetone

Structural formula
General
Surname	Hydroxyacetone
other names	Acetol 1-hydroxy-2-propanone Acetyl carbinol 2-oxopropanol Acetone alcohol
Molecular formula	C 3 H 6 O 2
Brief description	oily colorless liquid with a strange smell
External identifiers / databases
CAS number 116-09-6 EC number 204-124-8 ECHA InfoCard 100.003.750 PubChem 8299 Wikidata Q20236702
properties
Molar mass	74.08 g mol −1
Physical state	liquid
density	1.08 g cm −3 (20 ° C)
Melting point	−17 ° C
boiling point	147 ° C (decomposition)
Vapor pressure	7.5 hPa (20 ° C)
solubility	miscible with water
Refractive index	1.425 (20 ° C)
safety instructions
GHS labeling of hazardous substances Caution H and P phrases H: 226 P: 210
Toxicological data	2200 mg kg −1 ( LD 50 ,  rat ,  oral )
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C

Hydroxyacetone is a chemical compound from the group of ketones and is the simplest hydroxyketone .

Extraction and presentation

Hydroxyacetone can be obtained by reacting bromoacetone with potassium hydroxide and ethyl formate in methanolic solution. It is also formed in the troposphere by oxidation from isoprene . It is also produced in food during cooking.

properties

Hydroxyacetone is a hygroscopic oily colorless liquid with a strange odor that is miscible with water. It decomposes when heated above 147 ° C.

use

Hydroxyacetone is an important intermediate in the manufacture of polyols, acrolein, dyes and skin tanning agents. Asymmetric reduction in the presence of a microbial cell catalyst yields ( R ) -1,2-propanediol. It also serves as a component for Mannich and Aldol reactions.

safety instructions

The vapors of hydroxyacetone can form an explosive mixture with air ( flash point 56 ° C, ignition temperature 280 ° C).

Individual evidence

1. ↑ ^{a b c d e f g h i j k l} Entry on hydroxyacetone in the GESTIS substance database of the IFA , accessed on April 15, 2017(JavaScript required) .
2. ↑ ^{a b} Data sheet Hydroxyacetone, contains ≤500 ppm sodium carbonate as stabilizer, technical grade, 90% from Sigma-Aldrich , accessed on April 15, 2017 ( PDF ).
3. ↑ ^{a b} Amit Arora: Carbohodrates And Proteins . Discovery Publishing House, 2006, ISBN 978-81-8356-178-5 , pp. 139 ( limited preview in Google Book search).
4. ↑ Hans Peter Latscha, Uli Kazmaier, Helmut Klein: Organic Chemistry Chemistry Basic Knowledge II . Springer-Verlag, 2008, ISBN 978-3-540-77107-4 , pp. 219 ( limited preview in Google Book search).
5. ↑ Jack Calvert, Abdelwahid Mellouki, John Orlando, Michael Pilling, Timothy Wallington: Mechanisms of Atmospheric Oxidation of the Oxygenates . Oxford University Press, 2011, ISBN 978-0-19-987747-8 , pp. 691 ( limited preview in Google Book search).
6. ^ Encyclopedia of Meat Sciences . Elsevier, 2014, ISBN 978-0-12-384734-8 , pp. 394 ( limited preview in Google Book search).
7. ↑ Data sheet Hydroxyacetone, 95% at AlfaAesar, accessed on April 15, 2017 ( PDF )(JavaScript required) .