Phorone Explained

Phorone, or diisopropylidene acetone, is a yellow crystalline substance with a geranium odor, with formula or .

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

• Isophorone

References

• Merck Index, 11th Edition, 7307.

External links

• International Chemical Safety Cards

Notes and References

1. Laurent. Auguste. Sur les acides pinique et sylvique, et sur le camphoryle. Annales de Chimie et de Physique. 1837. 65. 324–332. 2nd series. On pinic and sylvic acids, and on camphoryl. French.

   see "Camphoryle", pp. 329–330.

2. See:
   • Gerhardt, Charles (1849) Comptes rendus des travaux de chimie (Paris, France: Masson, 1849), p. 385. (in French)
   • Gerhardt. Liès-Bodart. Trockne Destillation des camphorsauren Kalks. Annalen der Chemie und Pharmacie. 1849. 72. 3. 293–294. Dry distillation of calcium camphorate. German. 10.1002/jlac.18490720327. 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", …)
3. 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.
4. Book: Kekulé. August. Lehrbuch der organischen Chemie. 1866. 463. German. 2nd vol.. Erlangen, (Germany). Ferdinand Enke. Textbook of organic chemistry.
5. Encyclopedia: Hardo Siegel . Manfred Eggersdorfer . Ketones. Ullmann's Encyclopedia of Industrial Chemistry. 2005. Wiley-VCH. Weinheim. 10.1002/14356007.a15_077. 978-3-527-30673-2.