Diacetone alcohol
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| Diacetone alcohol | |
|---|---|
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| General | |
| Systematic name | 4-Hydroxy-4-methyl-2-pentanone |
| Other names | 4-Hydroxy-4-methylpentan-2-one 2-Pentanone, 4-hydroxy-4-methyl 4-Hydroxy-2-keto-4-methylpentane Diacetone alcohol |
| Molecular formula | C6H12O2 |
| SMILES | ? |
| Molar mass | 116.16 g/mol |
| Appearance | colorless liquid |
| CAS number | [123-42-2] |
| Properties | |
| Density and phase | 0.938 g/cm3 |
| Solubility in water | moderate |
| Other solvents | organic solvents |
| Melting point | -47 °C |
| Boiling point | 166 °C |
| Viscosity | ? cP at ? °C |
| Structure | |
| Dipole moment | ? D |
| Hazards | |
| MSDS | External MSDS |
| Main hazards | flammable |
| NFPA 704 | |
| Flash point | ? °C |
| R/S statement | R: 36 S: 24/25 |
| RTECS number | SA9100000 |
| Supplementary data page | |
| Structure and properties |
n = 1.423 |
| Thermodynamic data |
Phase behaviour Solid, liquid, gas |
| Spectral data | UV, IR, NMR, MS |
| Related compounds | |
| Related compounds | Methyl isobutyl ketone acetone |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references |
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Diacetone alcohol is a chemical compound with the formula CH3C(O)CH2C(OH)(CH3)2. This liquid is common synthetic intermediate used for the preparation of other compounds.
[edit] Synthesis
First identified by Heintz[1], its preparation entails the Ba(OH)2-catalyzed condensation of two molecules of acetone[2] It undergoes dehydration to give the α,β-unsaturated ketone, mesityl oxide:[3] Hydrogenation of mesityl oxide gives the industrial solvent methyl isobutyl ketone (“MIBK”).
[edit] References
- ^ Heintz, Ann. 169, 114 (1873)
- ^ Conant, J. B.; Tuttle, N. Diacetone Alcohol, Organic Syntheses, Collected Volume 1, p.199 (1941); Vol. 1, p.45, (1921).
- ^ Conant, J. B.; Tuttle, N. Mesityl Oxide, Organic Syntheses, Collected Volume 1, p. 345 (1941).
