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Phorone, or diisopropylidene acetone, is a yellow crystalline substance with a geranium odor, with
Crude phorone can be purified by repeated recrystallization from ethanol or ether, in which it is soluble.
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Ketones Alkene derivatives
formula
In science, a formula is a concise way of expressing information symbolically, as in a mathematical formula or a ''chemical formula''. The informal use of the term ''formula'' in science refers to the general construct of a relationship betwee ...
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 (an ...
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
In organic chemistry, ketonic decarboxylation (also known as decarboxylative ketonization) is a type of organic reaction and a decarboxylation converting two equivalents of a carboxylic acid () to a symmetric ketone () by the application of heat w ...
through the dry distillation of the calcium salt of camphoric acid
Camphoric acid, C10 H16 O4 or in Latin form Acidum camphoricum, is a white crystallisable substance obtained from the oxidation of camphor. It exists in three optically different forms; the dextrorotatory one is obtained by the oxidation of dext ...
.
:
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 to ...
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 miscib ...
. Mesityl oxide
Mesityl oxide is a Carbonyl#.CE.B1.2C.CE.B2-Unsaturated_carbonyl_compounds, 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 c ...
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 nitrogenous was ...
to form triacetone amine.
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