Cyclododecanone
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| Preferred IUPAC name
Cyclododecanone | |
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3D model (JSmol)
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| ECHA InfoCard | 100.011.450 Edit this at Wikidata |
PubChem CID
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CompTox Dashboard (EPA)
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| Properties | |
| C12H22O | |
| Molar mass | 182.307 g·mol−1 |
| Appearance | white solid |
| Melting point | 60.8 °C (141.4 °F; 333.9 K) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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.[1]
History and synthesis
[edit ]It was first obtained by Ružička et al. in 1926 by ketonic decarboxylation.[2] A higher-yield method by acyloin condensation was devised by Prelog et al. in 1947.[3]
It is now industrially produced by the oxidation of cyclododecane via cyclododecanol.[4]
Uses
[edit ]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.[5] It is also precursor to cyclohexadecanone, which is used in some fragrances.[6]
Hydrazone formation with pimagedine leads to a hypoglycemic formula.[7] Notice that the shape of the molecule can be made to appear like a pharmacy cross symbol.
References
[edit ]- ^ Richter, Victor von (1934). Organic Chemistry, Or, Chemistry of the Carbon Compounds: The alicyclic compounds and natural products. Elsevier.
- ^ Ruzicka, L.; Stoll, M.; Schinz, H. (1926). "Zur Kenntnis des Kohlenstoffringes II. Synthese der carbocyclischen Ketone vom Zehner- bis zum Achtzehnerring" . Helvetica Chimica Acta (in German). 9 (1): 249–264. doi:10.1002/hlca.19260090130. ISSN 1522-2675.
- ^ Prelog, V.; Frenkiel, L.; Kobelt, Magrit; Barman, P. (1947). "Zur Kenntnis des Kohlenstoffringes. Ein Herstellungsverfahren für vielgliedrige Cyclanone" . Helvetica Chimica Acta. 30 (6): 1741–1749. doi:10.1002/hlca.19470300637. ISSN 1522-2675.
- ^ 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
- ^ Teles, J. Henrique; Hermans, Ive; Franz, Gerhard; Sheldon, Roger A. (2015). "Oxidation". Ullmann's Encyclopedia of Industrial Chemistry. pp. 1–103. doi:10.1002/14356007.a18_261.pub2. ISBN 978-3-527-30385-4.
- ^ 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
- ^ J Nordmann, et al. U.S. patent 3,746,764 (1973 to Ugine Kuhlmann SA).
