Phorone

Phorone, or diisopropylidene acetone, is a yellow crystalline substance with a geranium odor, with formula C9H14O or ((CH3)2C=CH)2C=O.

Phorone
Names
Preferred IUPAC name
2,6-Dimethylhepta-2,5-dien-4-one
Other names
Phorone
Diisopropylidene acetone
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.007.261
EC Number
  • 207-986-3
RTECS number
  • MI5500000
UNII
UN number 1993
  • InChI=1S/C9H14O/c1-7(2)5-9(10)6-8(3)4/h5-6H,1-4H3 ☒N
    Key: MTZWHHIREPJPTG-UHFFFAOYSA-N ☒N
  • InChI=1/C9H14O/c1-7(2)5-9(10)6-8(3)4/h5-6H,1-4H3
    Key: MTZWHHIREPJPTG-UHFFFAOYAY
  • O=C(C=C(C)C)C=C(C)C
Properties
((CH3)2C=CH)2C=O
Molar mass 138.210 g·mol−1
Appearance Yellow crystals
Odor Geranium
Density 0.885 g/cm3
Melting point 28 °C (82 °F; 301 K)
Boiling point 198 to 199 °C (388 to 390 °F; 471 to 472 K)
Hazards
Flash point 79 °C (174 °F; 352 K)
Safety data sheet (SDS) External MSDS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

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]

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.
  1. Laurent, Auguste (1837). "Sur les acides pinique et sylvique, et sur le camphoryle" [On pinic and sylvic acids, and on camphoryl]. Annales de Chimie et de Physique. 2nd series (in French). 65: 324–332.; 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 (1849). "Trockne Destillation des camphorsauren Kalks" [Dry distillation of calcium camphorate]. Annalen der Chemie und Pharmacie (in German). 72 (3): 293–294. doi: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. Kekulé, August (1866). Lehrbuch der organischen Chemie [Textbook of organic chemistry] (in German). Vol. 2nd vol. Erlangen, (Germany): Ferdinand Enke. p. 463.
  5. Hardo Siegel; Manfred Eggersdorfer (2005). "Ketones". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a15_077. ISBN 978-3-527-30673-2.
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