Diacetone alcohol
Structural formula | |||||||||||||||||||
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General | |||||||||||||||||||
Surname | Diacetone alcohol | ||||||||||||||||||
other names |
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Molecular formula | C 6 H 12 O 2 | ||||||||||||||||||
Brief description |
colorless liquid with a sweet odor |
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properties | |||||||||||||||||||
Molar mass | 116.16 g mol −1 | ||||||||||||||||||
Physical state |
liquid |
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density |
0.93 g cm −3 |
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Melting point |
−47 ° C |
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boiling point |
166 ° C |
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Vapor pressure |
2.86 h Pa (30 ° C) |
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solubility |
miscible with water |
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Refractive index |
1.4213 (20 ° C) |
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safety instructions | |||||||||||||||||||
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MAK |
DFG / Switzerland: 20 ml m −3 or 96 mg m −3 |
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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 .
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).
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
- ↑ 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) .
- ↑ 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.
- ↑ 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 .
- ↑ 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.
- ↑ 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 .