Phorone
Chemical compound
From Wikipedia, the free encyclopedia
Phorone, or diisopropylidene acetone, is a yellow crystalline substance with a geranium odor, with formula C9H14O or ((CH3)2C=CH)2C=O.
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| Names | |
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| Preferred IUPAC name
2,6-Dimethylhepta-2,5-dien-4-one | |
| Other names
Phorone Diisopropylidene acetone | |
| Identifiers | |
3D model (JSmol) |
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| ChemSpider | |
| ECHA InfoCard | 100.007.261 |
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| UNII | |
| UN number | 1993 |
CompTox Dashboard (EPA) |
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| Properties | |
| ((CH3)2C=CH)2C=O | |
| Molar mass | 138.210 g·mol−1 |
| Appearance | Yellow crystals |
| Odor | Geranium |
| Density | 0.885 g/cm3 |
| Melting point | 28 °C (82 °F; 301 K) |
| Boiling point | 198 to 199 °C (388 to 390 °F; 471 to 472 K) |
| Hazards | |
| Flash point | 79 °C (174 °F; 352 K) |
| Safety data sheet (SDS) | External MSDS |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Preparation
It was first obtained in 1837 in impure form by the French chemist Auguste Laurent, who called it "camphoryle".[1] In 1849, the French chemist Charles Frédéric Gerhardt and his student Jean Pierre Liès-Bodart prepared it in a pure state and named it "phorone".[2] On both occasions it was produced by ketonization through the dry distillation of the calcium salt of camphoric acid.[3][4]
- CaC10H14O4 → C9H14O + CaCO3
It is now typically obtained by the acid-catalysed twofold aldol condensation of three molecules of acetone. Mesityl oxide is obtained as an intermediate and can be isolated.[5]
Crude phorone can be purified by repeated recrystallization from ethanol or ether, in which it is soluble.
Reactions
Phorone can condense with ammonia to form triacetone amine.