Cyclohexanone oxime

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.

Not to be confused with caprolactam.
Cyclohexanone oxime
Names
Preferred IUPAC name
N-Hydroxycyclohexanimine
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.002.613
EC Number
  • 202-874-0
UNII
UN number 2811
  • 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
  • C1CCC(=NO)CC1
Properties
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)
16 g/kg (in water)
-71.52·10−6 cm3/mol
Hazards
GHS labelling:
GHS02: FlammableGHS07: Exclamation markGHS08: Health hazard
Warning
H228, H302, H319, H373, H412
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

Preparation

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

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
  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. 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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