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{{Short description|Chemical compound}} |
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{{chembox |
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{{chembox |
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| Name = Phorone |
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|Watchedfields = changed |
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| ImageFile = Phorone.png |
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|verifiedrevid = 406340788 |
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<!-- | ImageSize = 180px --> |
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|Name = Phorone |
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| ImageName = |
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|ImageFile = Phorone.png |
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| IUPACName = 2,6-Dimethyl-2,5-heptadien-4-one |
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|PIN = 2,6-Dimethylhepta-2,5-dien-4-one |
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| OtherNames = Phorone<br />Diisopropylidene acetone |
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|OtherNames = Phorone<br />Diisopropylidene acetone |
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| Section1 = {{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| CASNo = 504-20-1 |
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|CASNo_Ref = {{cascite|correct|??}} |
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| SMILES = O=C(C=C(C)C)C=C(C)C |
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|CASNo = 504-20-1 |
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}} |
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|ChEBI = 35572 |
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| Section2 = {{Chembox Properties |
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|ChEMBL = 2766015 |
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| Formula = C<sub>9</sub>H<sub>14</sub>O<sub></sub> |
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|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| MolarMass = 138.20 g/mol |
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|ChemSpiderID = 10007 |
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| Density = 0.885 g/cm<sup>3</sup> |
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|EINECS = 207-986-3 |
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| MeltingPt = 28 °C |
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|PubChem = 10438 |
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| BoilingPt = 198-199 °C |
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|RTECS = MI5500000 |
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}} |
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|UNNumber = 1993 |
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| Section7 = {{Chembox Hazards |
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|UNII_Ref = {{fdacite|correct|FDA}} |
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| ExternalMSDS = }} |
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|UNII = 8F20OEI0MV |
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| FlashPt = 79°C |
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|SMILES = O=C(C=C(C)C)C=C(C)C |
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|InChI = 1/C9H14O/c1-7(2)5-9(10)6-8(3)4/h5-6H,1-4H3 |
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|InChIKey = MTZWHHIREPJPTG-UHFFFAOYAY |
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|StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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|StdInChI = 1S/C9H14O/c1-7(2)5-9(10)6-8(3)4/h5-6H,1-4H3 |
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|StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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|StdInChIKey = MTZWHHIREPJPTG-UHFFFAOYSA-N |
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}} |
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}} |
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|Section2={{Chembox Properties |
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|Formula = {{chem2|((CH3)2C\dCH)2C\dO}} |
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|C=9|H=14|O=1 |
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|Appearance = Yellow crystals |
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|Odor = Geranium |
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|Density = 0.885 g/cm<sup>3</sup> |
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|MeltingPtC = 28 |
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|BoilingPtC = 198 to 199 |
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}} |
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|Section3={{Chembox Hazards |
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|ExternalSDS = |
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|FlashPtC = 79 |
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}} |
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'''Phorone''', or '''diisopropylidene acetone''', is a yellow crystalline substance with a ] odor, with ] {{chem2|C9H14O}} or {{chem2|((CH3)2C\dCH)2C\dO}}. |
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==Preparation== |
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'''Phorone''', or diisopropylidene acetone, is a yellow crystalline substance with a ] odor. It is a ] product of ]. It can also be obtained from certain ] compounds. |
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It was first obtained in 1837 in impure form by the French chemist ], 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 ] and his student Jean Pierre Liès-Bodart prepared it in a pure state and named it "phorone".<ref>See: |
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* Gerhardt, Charles (1849) ''Comptes rendus des travaux de chimie'' (Paris, France: Masson, 1849), p. 385. (in French) |
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* {{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 ] through the dry distillation of the calcium salt of ].<ref>Watts, Henry, ''A Dictionary of Chemistry and the Allied Branches of Other Sciences'' (London, England: Longmans, Green, and Co., 1863), vol. 1, "Camphorone", </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> |
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:{{chem2|CaC10H14O4 → C9H14O + CaCO3}} |
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combustible when exposed to heat or flame |
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It is now typically obtained by the acid-catalysed twofold ] of three molecules of ]. ] 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> |
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] |
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Crude phorone can be purified by repeated recrystallization from ethanol or ether, in which it is soluble. |
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==Reactions== |
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Phorone can condense with ] to form ]. |
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==See also== |
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==See also== |
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==External links== |
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