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

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

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.

References

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

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.

[1]

[2]

[3]

[4]

[5]

Preparation

Reactions

See also

References

External links