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Cyclododecanone

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Cyclododecanone
Names
Preferred IUPAC name Cyclododecanone
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.011.450 Edit this at Wikidata
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C12H22O/c13-12-10-8-6-4-2-1-3-5-7-9-11-12/h1-11H2Key: SXVPOSFURRDKBO-UHFFFAOYSA-N
SMILES
  • C1CCCCCC(=O)CCCCC1
Properties
Chemical formula C12H22O
Molar mass 182.307 g·mol
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 , 100 kPa). Infobox references
Chemical compound

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.

History and synthesis

It was first obtained by Ružička et al. in 1926 by ketonic decarboxylation. A higher-yield method by acyloin condensation was devised by Prelog et al. in 1947.

It is now industrially produced by the oxidation of cyclododecane via cyclododecanol.

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. It is also precursor to cyclohexadecanone, which is used in some fragrances.

Pimagedine-cyclodecanone hydrazone.

Hydrazone formation with pimagedine leads to a hypoglycemic formula. Notice that the shape of the molecule can be made to appear like a pharmacy cross symbol.

References

  1. Richter, Victor von (1934). Organic Chemistry, Or, Chemistry of the Carbon Compounds: The alicyclic compounds and natural products. Elsevier.
  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 (in German). 9 (1): 249–264. doi:10.1002/hlca.19260090130. ISSN 1522-2675.
  3. 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.
  4. 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
  5. 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.
  6. 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
  7. J Nordmann, et al. U.S. patent 3,746,764 (1973 to Ugine Kuhlmann SA).


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