Cyclohexanone Identifiers CAS number PubChem ChemSpider UNII DrugBank KEGG ChEBI ChEMBL Jmol-3D images Image 1 Properties Molecular formula C6H10O Molar mass 98.15 g/mol Appearance Colorless, liquid Density 0.9478 g/mL, liquid Melting point
Solubility in water Slightly soluble Solubility in ethanol Miscible Refractive index (nD) 1.447 Viscosity 2.02 cP at 25 °C Thermochemistry Std enthalpy of
o298 −270.7 kJ mol−1 Std enthalpy of
o298 −3519.3 kJmol−1 Standard molar
o298 +229.03 J.K−1.mol−1 Hazards EU classification Harmful (Xn) R-phrases , S-phrases , NFPA 704 Flash point 44 °C Related compounds Related ketones Cyclopentanone, cycloheptanone Related compounds Cyclohexanol (what is: /?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Cyclohexanone is the organic compound with the formula (CH2)5CO. The molecule consists of six-carbon cyclic molecule with a ketone functional group. This colorless oil has an odor reminiscent of peardrop sweets as well as acetone. Over time, samples assume a yellow color due to oxidation. Cyclohexanone is slightly soluble in water (5-10 g/100 mL), but miscible with common organic solvents. Billions of kilograms are produced annually, mainly as a precursor to nylon.
- C6H12 + O2 → (CH2)5CO + H2O
This process co-forms cyclohexanol, and this mixture, called "KA oil" for ketone-alcohol oil, is the main feedstock for the production of adipic acid. The oxidation involves radicals and the intermediacy of the hydroperoxide C6H11O2H. In some cases, purified cyclohexanol, obtained by hydration of cyclohexene, is the precursor. Alternatively, cyclohexanone can be produced by the partial hydrogenation of phenol:
- C6H5OH + 2 H2 → (CH2)5CO
This process can also be adjusted to favor the formation of cyclohexanol.
Cyclohexanone can be prepared from cyclohexanol by oxidation with chromic oxide.
The great majority of cyclohexanone is consumed in the production of precursors to Nylon 6,6 and Nylon 6. About half of the world's supply is converted to adipic acid, one of two precursors for nylon 6,6. For this application, the KA oil (see above) is oxidized with nitric acid. The other half of the cyclohexanone supply is converted to the oxime. In the presence of sulfuric acid catalyst, the oxime rearranges to caprolactam, a precursor to nylon 6:
A recent study of plastic tubing used in medical procedures that circulate blood outside the body suggests a link between this compound and decreased heart function, swelling, loss of taste and short term memory loss.
- ^ International Chemical Safety Card 0425
- ^ NIOSH Pocket Guide to Chemical Hazards
- ^ Data extract from Landolt-Börnstein IV/25: Viscosity of Pure Organic Liquids and Binary Liquid Mixtures
- ^ a b c d e Michael T. Musser "Cyclohexanol and Cyclohexanone" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2005.doi:10.1002/14356007.a08_217
- ^ http://www.eurekalert.org/pub_releases/2009-05/jhmi-cfi043009.php
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Cyclohexanone — Général … Wikipédia en Français
cyclohexanone — ● cyclohexanone nom féminin Cétone (CH2)5C ≅ O dérivée du cyclohexane. (Liquide bouillant à 155 °C, la cyclohexanone est oxydée en acide adipique, source de polyamides.) … Encyclopédie Universelle
cyclohexanone — cikloheksanonas statusas T sritis chemija formulė Formulę žr. priede. priedas( ai) Grafinis formatas atitikmenys: angl. cyclohexanone rus. циклогексанон … Chemijos terminų aiškinamasis žodynas
cyclohexanone — noun Date: circa 1909 a liquid ketone C6H10O used especially as a solvent and in organic synthesis … New Collegiate Dictionary
cyclohexanone — /suy kloh hek seuh nohn , sik loh /, n. Chem. an oily liquid, C6H10O, with an acetone and peppermintlike odor, a cyclic butone used in organic synthesis and as an industrial solvent. [1905 10; see CYCLOHEXANE, ONE] * * * … Universalium
cyclohexanone — noun The alicyclic ketone obtained from cyclohexane by the replacement of a methylene group by a carbonyl group … Wiktionary
cyclohexanone — cy·clo·hex·a·none … English syllables
cyclohexanone — ˌnōn noun ( s) Etymology: International Scientific Vocabulary cyclohexane + one : a liquid ketone C6H10O made by the oxidation of cyclohexanol or cyclohexane and used chiefly as a solvent and in organic synthesis * * * /suy kloh hek seuh nohn ,… … Useful english dictionary
Cyclohexanone dehydrogenase — Identifiers EC number 126.96.36.199 CAS number 123516 43 8 … Wikipedia
Cyclohexanone oxime — This page was incorrectly redirected to Caprolactam (registry number 105 60 2). Cyclohexanone oxime (registry number 100 64 1) is a different compound; both have the empirical formula C6H11NO, but are structural isomers of each other. As the name … Wikipedia