Phorone

Phorone
Names
	Preferred IUPAC name 2,6-Dimethylhepta-2,5-dien-4-one
	Other names Phorone; Diisopropylidene acetone
Identifiers
CAS Number	504-20-1 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:35572;
ChEMBL	ChEMBL2766015;
ChemSpider	10007 ;
ECHA InfoCard	100.007.261
EC Number	207-986-3;
PubChem CID	10438;
RTECS number	MI5500000;
UNII	8F20OEI0MV ;
UN number	1993
CompTox Dashboard (EPA)	DTXSID1021584 ;
	InChI InChI=1S/C9H14O/c1-7(2)5-9(10)6-8(3)4/h5-6H,1-4H3 Key: MTZWHHIREPJPTG-UHFFFAOYSA-N ; InChI=1/C9H14O/c1-7(2)5-9(10)6-8(3)4/h5-6H,1-4H3 Key: MTZWHHIREPJPTG-UHFFFAOYAY;
	SMILES O=C(C=C(C)C)C=C(C)C;
Properties
Chemical formula	((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). verify (what is ?) Infobox references

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

Preparation[edit]

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[edit]

Phorone can condense with ammonia to form triacetone amine.

References[edit]

Merck Index, 11th Edition, 7307.

^ 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.
^
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", … )
^ 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.
^ Kekulé, August (1866). Lehrbuch der organischen Chemie [Textbook of organic chemistry] (in German). Vol. 2nd vol. Erlangen, (Germany): Ferdinand Enke. p. 463.
^ 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.

External links[edit]

International Chemical Safety Cards

[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] Gerhardt, Charles (1849) Comptes rendus des travaux de chimie (Paris, France: Masson, 1849), p. 385. (in French)

[4] 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.

[Ullmann-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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Preparation[edit]

Reactions[edit]

See also[edit]

References[edit]

External links[edit]