Diacetone alcohol

Structural formula
General
Surname	Diacetone alcohol
other names	4-hydroxy-4-methyl-2-pentanone ( IUPAC ) 4-hydroxy-4-methylpentan-2-one
Molecular formula	C 6 H 12 O 2
Brief description	colorless liquid with a sweet odor
External identifiers / databases
CAS number 123-42-2 EC number 204-626-7 ECHA InfoCard 100.004.207 PubChem 31256 ChemSpider 13838151 Wikidata Q421486
properties
Molar mass	116.16 g mol −1
Physical state	liquid
density	0.93 g cm −3
Melting point	−47 ° C
boiling point	166 ° C
Vapor pressure	2.86 h Pa (30 ° C)
solubility	miscible with water
Refractive index	1.4213 (20 ° C)
safety instructions
GHS hazard labeling from  Regulation (EC) No. 1272/2008 (CLP) , expanded if necessary Caution H and P phrases H: 226-319 P: 210-305 + 351 + 338
MAK	DFG / Switzerland: 20 ml m −3 or 96 mg m −3
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

Diacetone alcohol (DAA) is an organic compound and belongs to the group of hydroxy ketones . The basic substance is a colorless liquid with a slightly sweet odor.

Manufacturing

DAA is produced from acetone by allowing two acetone molecules to dimerize in an aldol reaction under the influence of basic reagents .

Production of diacetone alcohol by the aldol reaction of two acetone molecules.

In the laboratory, the representation is often done using a Soxhlet sleeve over calcium hydroxide . Diacetone alcohol is always formed from acetone during chromatography on aluminum oxide.

use

It is used as a solvent z. B. used for natural and synthetic resin paints and for dyes. As a solvent, it is not particularly stable over the long term if the typically sweet smell is gradually covered by a dull-smelling component (mesityl oxide).

Production of mesityl oxide from diacetone alcohol.

Diacetone alcohol is a precursor for mesityl oxide and methyl isobutyl ketone production.

Importance as a complex ligand

Some complexes are known which contain DAA as ligands , e.g. B. the polymeric complexes

[CoCl ₂ DAA] _n ,

[FeCl ₂ DAA] _n ,

[ZnCl ₂ DAA] or also

[MnBr ₂ (DAA) ₂ ] and

[Mn (DAA) ₃ ] ²⁺ [MnI ₄ ] ²⁻ · DAA

Individual evidence

1. ↑ ^{a b c d e f g h i} Entry on diacetone alcohol in the GESTIS substance database of the IFA , accessed on February 1, 2016(JavaScript required) .
2. ↑ David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Physical Constants of Organic Compounds, pp. 3-138.
3. ↑ Entry on 4-hydroxy-4-methylpentan-2-one in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on February 1, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .
4. ↑ Swiss Accident Insurance Fund (Suva): Limit values ​​- current MAK and BAT values (search for 123-42-2 or diacetone alcohol ), accessed on November 2, 2015.
5. ↑ Alfred Hoffman, J. Am. Chem. Soc. 31 , 1909 , 722.

Web links

• Oliver Schneider, Ernst Gerstner u. a .: Diacetone alcohol as a complex ligand. The crystal structures of [MnBr ₂ {O = C (Me) CH ₂ -C (Me) ₂ OH} ₂ ] and [M {O = C (Me) CH ₂ -C (Me) ₂ OH} ₂ ] [MCl ₄ ] with M = Fe, Co and Zn. In: Journal for inorganic and general chemistry. 625, 1999, p. 1101, doi : 10.1002 / (SICI) 1521-3749 (199907) 625: 7 <1101 :: AID-ZAAC1101> 3.0.CO; 2-E .
• Oliver Schneider, Ernst Gerstner u. a .: The crystal structure of the diacetone alcohol complex [Mn (DAA) ₃ ] ²⁺ [MnI ₄ ] ²⁻  - DAA. In: Journal of Inorganic and General Chemistry. 626, 2000, p. 827, doi : 10.1002 / (SICI) 1521-3749 (200004) 626: 4 <827 :: AID-ZAAC827> 3.0.CO; 2-N .