Cyclohexanone oxime

Cyclohexanone oxime is an organic compound. It is made as one of the steps for making nylon 6. It is one of the most important oximes.[1]

Cyclohexanone oxime
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
  • 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:
Template:GHS02Template:GHS07Template:GHS08
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


Cyclohexanone oxime is an organic compound. It is made as one of the steps for making nylon 6. It is one of the most important oximes.[1]

Preparation

Cyclohexanone oxime is prepared like most oximes. Cyclohexanone is mixed with hydroxylamine, causing a condensation reaction to make the oxime and water as a byproduct.

Uses

Cyclohexanone oxime is used to make caprolactam through a reaction called the Beckmann rearrangement.

Sources

  1. ↑ Bolotin, Dmitrii S.; Bokach, Nadezhda A.; Demakova, Marina Ya.; Kukushkin, Vadim Yu. (2017). "Metal-Involving Synthesis and Reactions of Oximes". Chemical Reviews. 117 (21): 13039–13122. doi:10.1021/acs.chemrev.7b00264. PMID 28991449.

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