Cyclododecanone
Chemical compound
From Wikipedia, the free encyclopedia
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]
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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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History and synthesis
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
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.
