Cyclododecanone

Last updated
Cyclododecanone
Cyclododecanon.png
Names
Preferred IUPAC name
Cyclododecanone
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.011.450 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • InChI=1S/C12H22O/c13-12-10-8-6-4-2-1-3-5-7-9-11-12/h1-11H2
    Key: SXVPOSFURRDKBO-UHFFFAOYSA-N
  • C1CCCCCC(=O)CCCCC1
Properties
C12H22O
Molar mass 182.307 g·mol−1
Appearancewhite 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).

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]

Contents

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]

Pimagedine-cyclodecanone hydrazone. Swiss cross.svg
Pimagedine-cyclodecanone hydrazone.

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

  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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