Cyclohexanone oxime

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Not to be confused with caprolactam.
Cyclohexanone oxime
Structure of cyclohexanone oxime.png
Cyclohexanone-oxime-from-xtal-2004-Mercury-3D-balls.png
Identifiers
100-64-1
ChEMBL ChEMBL103371714
ChemSpider 7236
Jmol 3D model Interactive image
PubChem 7517
UNII 2U60L00CGF YesY
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)
Hazards
Not available
S-phrases S24/25
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 its Beckmann rearrangement yielding ε-caprolactam:

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 gives cyclohexylamine.[3] It can also be hydrolyzed with acetic acid to give back cyclohexanone.

References[edit]

  1. ^ a b 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