{{Distinguish|caprolactam}} {{chembox | ImageFileL1 =Structure of cyclohexanone oxime.png | ImageSizeL1 =100px | ImageFileR1 = Cyclohexanone-oxime-from-xtal-2004-Mercury-3D-balls.png | ImageSizeR1 =120px | PIN = ''N''-Hydroxycyclohexanimine | OtherNames = |Section1={{Chembox Identifiers | CASNo_Ref = | CASNo =100-64-1 | EC_number = 202-874-0 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = 2U60L00CGF | UNNumber = 2811 | ChEMBL_Ref = | ChEMBL = 137035 | SMILES = C1CCC(=NO)CC1 | PubChem = 7517 | ChemSpiderID = 7236 | InChI = 1/C6H11NO/c8-7-6-4-2-1-3-5-6/h8H,1-5H2 | InChIKey = VEZUQRBDRNJBJY-UHFFFAOYAH | StdInChI = 1S/C6H11NO/c8-7-6-4-2-1-3-5-6/h8H,1-5H2 | StdInChIKey = VEZUQRBDRNJBJY-UHFFFAOYSA-N }} |Section2={{Chembox Properties | Formula =C<sub>6</sub>H<sub>11</sub>NO | MolarMass =113.16 g/mol | Appearance = white solid | Density = | MeltingPtC = 88 to 91 | MeltingPt_notes = | BoilingPtC = 204 to 206 | BoilingPt_notes = | Solubility = 16 g/kg (in water) | MagSus = −71.52·10<sup>−6</sup> cm<sup>3</sup>/mol }} |Section3={{Chembox Hazards | FlashPtC = 110 | AutoignitionPtC = | GHSPictograms = {{GHS02}}{{GHS07}}{{GHS08}} | GHSSignalWord = Warning | HPhrases = {{H-phrases|228|302|319|373|412}} | PPhrases = {{P-phrases|210|240|241|260|264|270|273|280|301+312|305+351+338|314|330|337+313|370+378|501}} | ExternalSDS = }} }}

'''Cyclohexanone oxime''' is an organic compound containing the functional group oxime. This colorless solid is an important intermediate in the production of nylon 6, a widely used polymer.

==Preparation== Cyclohexanone oxime can be prepared from the condensation reaction between cyclohexanone and hydroxylamine:<ref name=Eck>J. C. Eck and C. S. Marvel "ε-Benzoylaminocaproic Acid" Org. Synth. 1939, volume 19, pp. 20. {{doi|10.15227/orgsyn.019.0020}}</ref> :C<sub>5</sub>H<sub>10</sub>CO + H<sub>2</sub>NOH → C<sub>5</sub>H<sub>10</sub>C=NOH + H<sub>2</sub>O

Alternatively, another industrial route involves the reaction of cyclohexane with nitrosyl chloride, which is a free-radical reaction. This method is advantageous as cyclohexane is much cheaper than cyclohexanone.

==Reactions== The most famous and commercially important reaction of cyclohexanone oxime is Beckmann rearrangement yielding ε-caprolactam, which is used to produce Nylon 6: none|300px

This reaction is catalyzed by sulfuric acid,<ref name=Eck/> but industrial scale reactions use solid acids.<ref>Corma, Avelino; Garcia, Hermenegildo "Organic reactions catalyzed over solid acids" Catalysis Today 1997, volume 38, pp. 257-308. {{doi|10.1016/S0920-5861(97)81500-1}}</ref>

Typical of oximes, the compound can be reduced by sodium amalgam to produce cyclohexylamine.<ref>W. H. Lycan, S. V. Puntambeker, and C. S. Marvel "n-Heptylamine" Org. Synth. 1931, volume 11, pp. 58.{{doi|10.15227/orgsyn.011.0058}}</ref> It can also be hydrolyzed with acetic acid to give back cyclohexanone.

==References== {{Reflist}}

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Category:Cyclohexanes Category:Ketoximes