Chemistry:Diacetone alcohol
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| Names | |
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| Preferred IUPAC name
4-Hydroxy-4-methylpentan-2-one | |
| Other names
4-Hydroxy-4-methyl-2-pentanone; 4-Hydroxy-2-keto-4-methylpentane; Diacetone alcohol
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| Identifiers | |
3D model (JSmol)
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| 1740440 | |
| ChEBI | |
| ChemSpider | |
| EC Number |
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PubChem CID
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| RTECS number |
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| UNII | |
| UN number | 1148 |
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| Properties | |
| C6H12O2 | |
| Molar mass | 116.160 g·mol−1 |
| Appearance | Colorless liquid |
| Odor | Odorless |
| Density | 0.938 g/cm3 |
| Melting point | −47 °C (−53 °F; 226 K) |
| Boiling point | 166 °C (331 °F; 439 K) |
| moderate | |
| Solubility | most organic solvents |
Refractive index (nD)
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1.4235 |
| Hazards | |
| Main hazards | Flammable |
| GHS pictograms |  
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| GHS Signal word | Warning |
| H226, H319, H335 | |
| P210, P233, P240, P241, P242, P243, P261, P264, P271, P280, P303+361+353, P304+340, P305+351+338, P312, P337+313, P370+378, P403+233, P403+235, P405, P501 | |
| Flash point | 52 °C; 125 °F; 325 K |
| Explosive limits | 1.8–6.9%[1] |
| Lethal dose or concentration (LD, LC): | |
LD50 (median dose)
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4000 mg/kg (oral, rat) 4653 mg/kg (oral, rabbit) 3950 mg/kg (oral, mouse)[2] |
| NIOSH (US health exposure limits): | |
PEL (Permissible)
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TWA 50 ppm (240 mg/m3)[1] |
| Related compounds | |
Related compounds
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Acetone methyl isobutyl ketone |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
 verify (what is   ?)
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| Infobox references | |
Diacetone alcohol is an organic compound with the formula CH3C(O)CH2C(OH)(CH3)2, sometimes called DAA. This colorless liquid is a common synthetic intermediate used for the preparation of other compounds, and is also used as a solvent.[3]
Synthesis and reactions
First identified by Heintz,[4] one standard laboratory preparation of DAA entails the Ba(OH)2-catalyzed condensation of two molecules of acetone.[5]
It undergoes dehydration to give the α,β-unsaturated ketone called mesityl oxide.[6] Hydrogenation of diacetone alcohol gives hexylene glycol. Condensation with urea give "diacetone-monourea", i.e. the heterocycle 3,4-dihydro- 4,4,6-trimethyl-2(1H)-pyrimidone.[3]
Uses
Diacetone alcohol is used in cellulose ester lacquers,[3] particularly of the brushing type, where it produces brilliant gloss and hard film and where its lack of odor is desirable. It is used in lacquer thinners, dopes, wood stains, wood preservatives and printing pastes; in coating compositions for paper and textiles; permanent markers;[7] in making artificial silk and leather; in imitation gold leaf; in celluloid cements; as a preservative for animal tissue; in metal cleaning compounds; in the manufacture of photographic film; and in hydraulic brake fluids, where it is usually mixed with an equal volume of castor oil.
Safety
The -1">50 (oral, rats) is 4 g/kg.[3]
References
- ↑ 1.0 1.1 1.2 NIOSH Pocket Guide to Chemical Hazards. "#0178". National Institute for Occupational Safety and Health (NIOSH). https://www.cdc.gov/niosh/npg/npgd0178.html.
- ↑ "Diacetone alcohol". Immediately Dangerous to Life and Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH). https://www.cdc.gov/niosh/idlh/123422.html.
- ↑ 3.0 3.1 3.2 3.3 Sifniades, Stylianos; Levy, Alan B. (2000). "Acetone". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a01_079. ISBN 3527306730.
- ↑ Heintz, Ann. 169, 114 (1873)
- ↑ Conant, J. B.; Tuttle, N. (1921). "Diacetone Alcohol". Organic Syntheses 1: 45. doi:10.15227/orgsyn.001.0045.
- ↑ Conant, J. B.; Tuttle, N. (1921). "Mesityl Oxide". Organic Syntheses 1: 53. doi:10.15227/orgsyn.001.0053.
- ↑ Sharpie Chisel Tip Permanent Marker at the Consumer Product Information Database
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