View source for Phorone

{{Short description|Chemical compound}}
{{chembox
|Verifiedfields = changed
|Watchedfields = changed
|verifiedrevid = 406340788
|Name = Phorone
|ImageFile = Phorone.png
|PIN = 2,6-Dimethylhepta-2,5-dien-4-one
|OtherNames = Phorone<br />Diisopropylidene acetone
|Section1={{Chembox Identifiers
|CASNo_Ref = {{cascite|correct|??}}
|CASNo = 504-20-1
|ChEBI = 35572
|ChEMBL = 2766015
|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
|ChemSpiderID = 10007
|EINECS = 207-986-3
|PubChem = 10438
|RTECS = MI5500000
|UNNumber = 1993
|UNII_Ref = {{fdacite|correct|FDA}}
|UNII = 8F20OEI0MV
|SMILES = O=C(C=C(C)C)C=C(C)C
|InChI = 1/C9H14O/c1-7(2)5-9(10)6-8(3)4/h5-6H,1-4H3
|InChIKey = MTZWHHIREPJPTG-UHFFFAOYAY
|StdInChI_Ref = {{stdinchicite|changed|chemspider}}
|StdInChI = 1S/C9H14O/c1-7(2)5-9(10)6-8(3)4/h5-6H,1-4H3
|StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
|StdInChIKey = MTZWHHIREPJPTG-UHFFFAOYSA-N
}}
|Section2={{Chembox Properties
|Formula = {{chem2|((CH3)2C\dCH)2C\dO}}
|C=9|H=14|O=1
|Appearance = Yellow crystals
|Odor = Geranium
|Density = 0.885 g/cm<sup>3</sup>
|MeltingPtC = 28
|BoilingPtC = 198 to 199
}}
|Section3={{Chembox Hazards
|ExternalSDS = [http://www.inchem.org/documents/icsc/icsc/eics1157.htm External MSDS]
|FlashPtC = 79
}}
}}
'''Phorone''', or '''diisopropylidene acetone''', is a yellow crystalline substance with a [[Pelargonium|geranium]] odor, with [[chemical formula|formula]] {{chem2|C9H14O}} or {{chem2|((CH3)2C\dCH)2C\dO}}.
==Preparation==
It was first obtained in 1837 in impure form by the French chemist [[Auguste Laurent]], who called it "camphoryle".<ref>{{cite journal|last1=Laurent|first1=Auguste|title=Sur les acides pinique et sylvique, et sur le camphoryle|journal=Annales de Chimie et de Physique|date=1837|volume=65|pages=324–332|url=https://babel.hathitrust.org/cgi/pt?id=hvd.hx3dx3;view=1up;seq=328|series=2nd series|trans-title=On pinic and sylvic acids, and on camphoryl|language=French}}; see "Camphoryle", pp. 329–330.</ref> 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".<ref>See:
* Gerhardt, Charles (1849) ''Comptes rendus des travaux de chimie'' (Paris, France: Masson, 1849), p. 385. (in French)
* {{cite journal|last1=Gerhardt|last2=Liès-Bodart|title=Trockne Destillation des camphorsauren Kalks|journal=Annalen der Chemie und Pharmacie|date=1849|volume=72|issue=3|pages=293–294|url=https://babel.hathitrust.org/cgi/pt?id=mdp.39015026322084;view=1up;seq=673|trans-title=Dry distillation of calcium camphorate|language=German|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", … )</ref> On both occasions it was produced by [[ketonization]] through the dry distillation of the calcium salt of [[camphoric acid]].<ref>Watts, Henry, ''A Dictionary of Chemistry and the Allied Branches of Other Sciences'' (London, England: Longmans, Green, and Co., 1863), vol. 1, "Camphorone", [https://babel.hathitrust.org/cgi/pt?id=nyp.33433079412726;view=1up;seq=753 p. 733.]</ref><ref>{{cite book|last1=Kekulé|first1=August|title=Lehrbuch der organischen Chemie|date=1866|page=463|url=https://books.google.com/books?id=XJlPAAAAYAAJ&pg=PA463|language=German|volume=2nd vol.|place=Erlangen, (Germany)|publisher=Ferdinand Enke|trans-title=Textbook of organic chemistry}}</ref>
:{{chem2|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.<ref name=Ullmann>{{cite encyclopedia|author=Hardo Siegel |author2=Manfred Eggersdorfer |title=Ketones|encyclopedia=Ullmann's Encyclopedia of Industrial Chemistry|year=2005|publisher=Wiley-VCH|place=Weinheim|doi=10.1002/14356007.a15_077|isbn=978-3-527-30673-2}}</ref>
[[File:Phoron formation.svg|frameless|600px|center]]
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'''.
{{reflist}}
==External links==
*[https://web.archive.org/web/20050209125437/http://www.itcilo.it/english/actrav/telearn/osh/ic/504201.htm International Chemical Safety Cards]
[[Category:Ketones]]
[[Category:Alkene derivatives]]