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Phorone, or diisopropylidene acetone, is a yellow crystalline substance with a
Crude phorone can be purified by repeated recrystallization from ethanol or ether, in which it is soluble.
International Chemical Safety Cards
Ketones Alkene derivatives
geranium
''Geranium'' is a genus of 422 species of annual, biennial, and perennial plants that are commonly known as geraniums or cranesbills. They are found throughout the temperate regions of the world and the mountains of the tropics, but mostly i ...
odor, with formula or .
Preparation
It was first obtained in 1837 in impure form by the French chemist Auguste Laurent, who called it "camphoryle". In 1849, the French chemistCharles Frédéric Gerhardt
Charles Frédéric Gerhardt (21 August 1816 – 19 August 1856) was a French chemist, born in Alsace and active in Paris, Montpellier, and his native Strasbourg.
Biography
He was born in Strasbourg, which is where he attended the gymnasium (a ...
and his student Jean Pierre Liès-Bodart prepared it in a pure state and named it "phorone". On both occasions it was produced by ketonization through the dry distillation of the calcium salt of camphoric acid.
:
It is now typically obtained by the acid-catalysed twofold aldol condensation
An aldol condensation is a condensation reaction in organic chemistry in which two carbonyl moieties (of aldehydes or ketones) react to form a β-hydroxyaldehyde or β-hydroxyketone (an aldol reaction), and this is then followed by dehydration ...
of three molecules of acetone
Acetone (2-propanone or dimethyl ketone), is an organic compound with the formula . It is the simplest and smallest ketone (). It is a colorless, highly volatile and flammable liquid with a characteristic pungent odour.
Acetone is miscible wi ...
. Mesityl oxide
Mesityl oxide is a α,β-unsaturated ketone with the formula CH3C(O)CH=C(CH3)2. This compound is a colorless, volatile liquid with a honey-like odor.
Synthesis
It is prepared by the aldol condensation of acetone to give diacetone alcohol, which ...
is obtained as an intermediate and can be isolated.
Crude phorone can be purified by repeated recrystallization from ethanol or ether, in which it is soluble.
Reactions
Phorone can condense withammonia
Ammonia is an inorganic compound of nitrogen and hydrogen with the formula . A stable binary hydride, and the simplest pnictogen hydride, ammonia is a colourless gas with a distinct pungent smell. Biologically, it is a common nitrogeno ...
to form triacetone amine
Triacetonamine is an organic compound with the formula OC(CH2CMe2)2NH (where Me = CH3). It is a colorless or white solid that melts near room temperature. The compound is an intermediate in the preparation of 2,2,6,6-tetramethylpiperidine, a s ...
.
See also
*Isophorone
Isophorone is an α,β-unsaturated cyclic ketone. It is a colorless liquid with a characteristic peppermint-like odor, although commercial samples can appear yellowish. Used as a solvent and as a precursor to polymers, it is produced on a large ...
References
*''Merck Index'', 11th Edition, 7307. {{reflistExternal links
International Chemical Safety Cards
Ketones Alkene derivatives