Cyclododecanone Explained

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

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.

Notes and References

1. Book: Richter, Victor von . Organic Chemistry, Or, Chemistry of the Carbon Compounds: The alicyclic compounds and natural products . 1934 . Elsevier . en.
2. Ruzicka . L. . Stoll . M. . Schinz . H. . 1926 . Zur Kenntnis des Kohlenstoffringes II. Synthese der carbocyclischen Ketone vom Zehner- bis zum Achtzehnerring . Helvetica Chimica Acta . de . 9 . 1 . 249–264 . 10.1002/hlca.19260090130 . 1522-2675.
3. Prelog . V. . Frenkiel . L. . Kobelt . Magrit . Barman . P. . 1947 . Zur Kenntnis des Kohlenstoffringes. Ein Herstellungsverfahren für vielgliedrige Cyclanone . Helvetica Chimica Acta . en . 30 . 6 . 1741–1749 . 10.1002/hlca.19470300637 . 1522-2675.
4. Schiffer, T.; Oenbrink, G. "Cyclododecanol, Cyclododecanone, and Laurolactam" in Ullman’s Encyclopedia of Industrial Chemistry: Wiley-VCH, 2009.
5. Book: 10.1002/14356007.a18_261.pub2 . Oxidation . Ullmann's Encyclopedia of Industrial Chemistry . 2015 . Teles . J. Henrique . Hermans . Ive . Franz . Gerhard . Sheldon . Roger A. . 1–103 . 978-3-527-30385-4 .
6. Johannes Panten and Horst Surburg "Flavors and Fragrances, 2. Aliphatic Compounds" in Ullmann's Encyclopedia of Industrial Chemistry, 2015, Wiley-VCH, Weinheim.
7. J Nordmann, et al. (1973 to Ugine Kuhlmann SA).