Cyclohexanone oxime

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title: "Cyclohexanone oxime" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["cyclohexanes", "ketoximes"] topic_path: "general/cyclohexanes" source: "https://en.wikipedia.org/wiki/Cyclohexanone_oxime" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

| 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 = | 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 =C6H11NO | 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 = −71.52·10−6 cm3/mol |Section3={{Chembox Hazards | FlashPtC = 110 | AutoignitionPtC = | GHSPictograms = | GHSSignalWord = Warning | HPhrases = | PPhrases = | 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: :C5H10CO + H2NOH → C5H10C=NOH + H2O

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: ::figure[src="https://upload.wikimedia.org/wikipedia/commons/f/ff/Beckmann_rearrangement_of_cyclohexanone_oxime.png"] ::

This reaction is catalyzed by sulfuric acid,

Typical of oximes, the compound can be reduced by sodium amalgam to produce cyclohexylamine. It can also be hydrolyzed with acetic acid to give back cyclohexanone.

References

References

  1. J. C. Eck and C. S. Marvel "ε-Benzoylaminocaproic Acid" Org. Synth. 1939, volume 19, pp. 20. {{doi. 10.15227/orgsyn.019.0020
  2. but industrial scale reactions use [[solid acid]]s.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
  3. 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

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cyclohexanesketoximes