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Names | |||
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Preferred IUPAC name
N-Hydroxycyclohexanimine | |||
Identifiers | |||
3D model (JSmol)
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ChEMBL | |||
ChemSpider | |||
ECHA InfoCard | 100.002.613 | ||
EC Number |
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PubChem CID
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UNII | |||
UN number | 2811 | ||
CompTox Dashboard (EPA)
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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: | |||
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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).
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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:
![](https://upload.wikimedia.org/wikipedia/commons/thumb/f/ff/Beckmann_rearrangement_of_cyclohexanone_oxime.png/300px-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
[edit]- ^ 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
- ^ 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
- ^ 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