Diacetone alcohol
From Wikipedia, the free encyclopedia
| Diacetone alcohol | |
|---|---|
 |
|
| IUPAC name | 4-Hydroxy-4-methyl-pentan-2-one |
| Other names | 2-Pentanone, 4-hydroxy-4-methyl; 4-Hydroxy-2-keto-4-methylpentane; Diacetone alcohol |
| Identifiers | |
| CAS number | [123-42-2] |
| RTECS number | SA9100000 |
| SMILES | CC(=O)CC(C)(C)O |
| Properties | |
| Molecular formula | C6H12O2 |
| Molar mass | 116.16 g/mol |
| Appearance | Colorless liquid |
| Density | 0.938 g/mL |
| Melting point |
- 47 °C |
| Boiling point |
166 °C |
| Solubility in water | moderate |
| Solubility | most organic solvents |
| Hazards | |
| Main hazards | Flammable |
| R-phrases | R36 |
| S-phrases | S24/25 |
| Related compounds | |
| Related compounds | Acetone, methyl isobutyl ketone |
| 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.
It is a natural ingredient of Sleepy grass (Achnatherum robustum).
[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. (1941). "Diacetone Alcohol". Org. Synth.; Coll. Vol. 1: 199.
- ^ Conant, J. B.; Tuttle, N. (1941). "Mesityl Oxide". Org. Synth.; Coll. Vol. 1: 345.
