cyclododecanone
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| ImageFile = Cyclododecanon.png
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| PIN = Cyclododecanone
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|Section1={{Chembox Identifiers
| CASNo = 830-13-7
| CASNo_Ref = {{cascite|correct|CAS}}
| UNII = WL053118A9
| UNII_Ref = {{fdacite|correct|FDA}}
| PubChem = 13246
| ChemSpiderID = 12690
| SMILES = C1CCCCCC(=O)CCCCC1
| StdInChI = 1S/C12H22O/c13-12-10-8-6-4-2-1-3-5-7-9-11-12/h1-11H2
| StdInChIKey = SXVPOSFURRDKBO-UHFFFAOYSA-N }}
|Section2={{Chembox Properties
| C=12|H=22|O=1
| Appearance = white solid
| Density =
| MeltingPtC = 60.8
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|Section3={{Chembox Hazards
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Cyclododecanone is an organic compound with the formula (CH2)11CO. It is a cyclic ketone that exists as a white solid at room temperature. Like its smaller analogs but unlike the larger ones, it has a camphor-like odor.{{Cite book |last=Richter |first=Victor von |url=https://books.google.com/books?id=lKcEAAAAMAAJ&q=C12+camphor |title=Organic Chemistry, Or, Chemistry of the Carbon Compounds: The alicyclic compounds and natural products |date=1934 |publisher=Elsevier |language=en}}
History and synthesis
It was first obtained by Ružička et al. in 1926 by ketonic decarboxylation.{{Cite journal |last=Ruzicka |first=L. |last2=Stoll |first2=M. |last3=Schinz |first3=H. |date=1926 |title=Zur Kenntnis des Kohlenstoffringes II. Synthese der carbocyclischen Ketone vom Zehner- bis zum Achtzehnerring |url=https://onlinelibrary.wiley.com/doi/10.1002/hlca.19260090130 |journal=Helvetica Chimica Acta |language=de |volume=9 |issue=1 |pages=249–264 |doi=10.1002/hlca.19260090130 |issn=1522-2675}} A higher-yield method by acyloin condensation was devised by Prelog et al. in 1947.{{Cite journal |last=Prelog |first=V. |last2=Frenkiel |first2=L. |last3=Kobelt |first3=Magrit |last4=Barman |first4=P. |date=1947 |title=Zur Kenntnis des Kohlenstoffringes. Ein Herstellungsverfahren für vielgliedrige Cyclanone |url=https://onlinelibrary.wiley.com/doi/abs/10.1002/hlca.19470300637 |journal=Helvetica Chimica Acta |language=en |volume=30 |issue=6 |pages=1741–1749 |doi=10.1002/hlca.19470300637 |issn=1522-2675}}
It is now industrially produced by the oxidation of cyclododecane via cyclododecanol.Schiffer, T.; Oenbrink, G. "Cyclododecanol, Cyclododecanone, and Laurolactam" in Ullman’s Encyclopedia of Industrial Chemistry: Wiley-VCH, 2009. {{doi|10.1002/14356007.a08_201.pub2}}
Uses
Cyclododecanone is oxidized on an industrial scale to give the corresponding dicarboxylic acid 1,12-dodecanedioic acid and laurolactam, which are precursors to certain specialized nylons.{{cite book |doi=10.1002/14356007.a18_261.pub2 |chapter=Oxidation |title=Ullmann's Encyclopedia of Industrial Chemistry |date=2015 |last1=Teles |first1=J. Henrique |last2=Hermans |first2=Ive |last3=Franz |first3=Gerhard |last4=Sheldon |first4=Roger A. |pages=1–103 |isbn=978-3-527-30385-4 }} It is also precursor to cyclohexadecanone, which is used in some fragrances.Johannes Panten and Horst Surburg "Flavors and Fragrances, 2. Aliphatic Compounds" in Ullmann's Encyclopedia of Industrial Chemistry, 2015, Wiley-VCH, Weinheim.{{doi|10.1002/14356007.t11_t01}}
Hydrazone formation with pimagedine leads to a hypoglycemic formula.J Nordmann, et al. {{US patent|3746764}} (1973 to Ugine Kuhlmann SA). Notice that the shape of the molecule can be made to appear like a pharmacy cross symbol.