Cyclohexanone oxime

Not to be confused with caprolactam.

Cyclohexanone oxime

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Identifiers
CAS Number	100-64-1
ChEMBL	ChEMBL103371714
ChemSpider	7236
Jmol 3D model	Interactive image
PubChem	7517
InChI InChI=1S/C6H11NO/c8-7-6-4-2-1-3-5-6/h8H,1-5H2 Key: VEZUQRBDRNJBJY-UHFFFAOYSA-N InChI=1/C6H11NO/c8-7-6-4-2-1-3-5-6/h8H,1-5H2 Key: VEZUQRBDRNJBJY-UHFFFAOYAH
SMILES C1CCC(=NO)CC1
Properties
Chemical formula	C6H11NO
Molar mass	113.16 g/mol
Appearance	Gray crystals
Melting point	88 to 91 °C (190 to 196 °F; 361 to 364 K)
Boiling point	204 to 206 °C (399 to 403 °F; 477 to 479 K)
Solubility in water	insoluble
Vapor pressure	{{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Cyclohexanone oxime is an organic compound containing the functional group oxime. This compound is usually not isolated as a pure compound as it is unstable when pure. However, it is an important intermediate in the production of nylon 6, a widely used polymer. It should not be confused with caprolactam, which is an isomer of the compound.

Preparation

Cyclohexanone oxime can be prepared from the condensation reaction between cyclohexanone and hydroxylamine, in the presence of an acid catalyst.

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.

Reaction

The most famous and important reaction is that cyclohexanone oxime undergoes Beckmann rearrangement when heated with an acid catalyst, yielding ε-caprolactam:

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As the compound contains the oxime group, it undergoes usual reactions of an oxime. For example, reducing cyclohexanone oxime by sodium amalgam gives cyclohexylamine. It can also be hydrolyzed with acetic acid to give cyclohexanone again.