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Phorone

Chemical compound From Wikipedia, the free encyclopedia

Phorone
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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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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]

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Crude phorone can be purified by repeated recrystallization from ethanol or ether, in which it is soluble.

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Reactions

Phorone can condense with ammonia to form triacetone amine.

See also

References

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