Phorone
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Template:Chembox image cellTemplate:Chembox AllOtherNamesTemplate:Chembox headerbarTemplate:Chembox IndexlistTemplate:Chembox JmolTemplate:Chembox ChEMBLTemplate:Chembox ECHATemplate:Chembox E numberTemplate:Chembox IUPHAR ligandTemplate:Chembox UNIITemplate:Chembox CompToxTemplate:Chembox headerbarTemplate:Chembox headerbarTemplate:Chembox SDSTemplate:Chembox Datapage checkTemplate:Chembox Footer| Template:Longitem | Template:Unbulleted list |
| ChEBI | Template:Unbulleted list |
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| UN number | 1993 |
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| Template:Longitem | Template:Chem2 |
| Molar mass | Template:Chem molar mass |
| Appearance | Yellow crystals |
| Odor | Geranium |
| Density | 0.885 g/cm3 |
| Melting point | Template:Chembox CalcTemperatures |
| Boiling point | Template:Chembox CalcTemperatures |
| Flash point | Template:Chembox CalcTemperatures |
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Phorone, or diisopropylidene acetone, is a yellow crystalline substance with a geranium odor, with formula Template:Chem2 or Template:Chem2.
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]
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.
See also
References
- Merck Index, 11th Edition, 7307.
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- ↑ Script error: No such module "Citation/CS1".; see "Camphoryle", pp. 329–330.
- ↑ See:
- Gerhardt, Charles (1849) Comptes rendus des travaux de chimie (Paris, France: Masson, 1849), p. 385. (in French)
- Script error: No such module "Citation/CS1". From p. 293: "Dieses Oel, welches Gerhardt und Lies-Bodart mit dem Namen Phoron bezeichnen, … " (This oil, which Gerhardt and Liès-Bodart designate by the name "phorone", … )
- ↑ Watts, Henry, A Dictionary of Chemistry and the Allied Branches of Other Sciences (London, England: Longmans, Green, and Co., 1863), vol. 1, "Camphorone", p. 733.
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