Cyclohexanone oxime

Cyclohexanone oxime

Names
Preferred IUPAC name N-Hydroxycyclohexanimine
Identifiers
CAS Number	100-64-1
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL137035
ChemSpider	7236
ECHA InfoCard	100.002.613
EC Number	202-874-0
PubChem CID	7517
UNII	2U60L00CGF Y
UN number	2811
CompTox Dashboard (EPA)	DTXSID4021842
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	white solid
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	16 g/kg (in water)
Magnetic susceptibility (χ)	-71.52·10−6 cm3/mol
Hazards
GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H228, H302, H319, H373, H412
Precautionary statements	P210, P240, P241, P260, P264, P270, P273, P280, P301+P312, P305+P351+P338, P314, P330, P337+P313, P370+P378, P501
Flash point	110 °C (230 °F; 383 K)
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 colorless solid is an important intermediate in the production of nylon 6, a widely used polymer.

Preparation[edit]

Cyclohexanone oxime can be prepared from the condensation reaction between cyclohexanone and hydroxylamine:^[1]

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[edit]

The most famous and commercially important reaction of cyclohexanone oxime is Beckmann rearrangement yielding ε-caprolactam:

This reaction is catalyzed by sulfuric acid,^[1] but industrial scale reactions use solid acids.^[2]

Typical of oximes, the compound can be reduced by sodium amalgam to produce cyclohexylamine.^[3] It can also be hydrolyzed with acetic acid to give back cyclohexanone.

References[edit]