Cyclododecanone is an organic compound with the formula (CH2)11CO. It is a cyclic ketone that exists as a white solid at room temperature.
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| Names | |
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| Preferred IUPAC name
Cyclododecanone | |
| Identifiers | |
3D model (JSmol)
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| ChemSpider | |
| ECHA InfoCard | 100.011.450 |
PubChem CID
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| UNII | |
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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Synthesis
editIt is produced by the oxidation of cyclododecane via cyclododecanol.[1]
Uses
editCyclododecanone 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.[2] It is also precursor to cyclohexadecanone, which is used in some fragrances.[3]
Hydrazone formation with pimagedine leads to a hypoglycemic formula.[4] Notice that the shape of the molecule can be made to appear like a pharmacy cross symbol.
References
edit- ^ 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).
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