Cyclohexanone oxime

Last updated
Cyclohexanone oxime
Structure of cyclohexanone oxime.png
Cyclohexanone-oxime-from-xtal-2004-Mercury-3D-balls.png
Names
Preferred IUPAC name
N-Hydroxycyclohexanimine
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.002.613 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 202-874-0
PubChem CID
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
Appearancewhite 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:
GHS-pictogram-flamme.svg GHS-pictogram-exclam.svg GHS-pictogram-silhouette.svg
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).

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.

Contents

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, which is used to produce Nylon 6:

Beckmann rearrangement of cyclohexanone oxime.png

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. 1 2 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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