“Cyclohexanone oxime”的意思、由来-开放百科全书

词条

Cyclohexanone oxime

释义

Preparation
Reactions
References

{{distinguish|caprolactam}}{{chembox
| ImageFileL1 =Structure of cyclohexanone oxime.png
| ImageSizeL1 =100px
| ImageFileR1 = Cyclohexanone-oxime-from-xtal-2004-Mercury-3D-balls.png
| ImageSizeR1 =120px
| IUPACName =
| OtherNames =
|Section1={{Chembox Identifiers
| CASNo_Ref =
| CASNo =100-64-1
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 2U60L00CGF
| ChEMBL_Ref =
| ChEMBL = 103371714
| SMILES = C1CCC(=NO)CC1
| PubChem = 7517
| ChemSpiderID = 7236
| InChI = 1/C6H11NO/c8-7-6-4-2-1-3-5-6/h8H,1-5H2
| InChIKey = VEZUQRBDRNJBJY-UHFFFAOYAH
| StdInChI = 1S/C6H11NO/c8-7-6-4-2-1-3-5-6/h8H,1-5H2
| StdInChIKey = VEZUQRBDRNJBJY-UHFFFAOYSA-N
|Section2={{Chembox Properties
| Formula =C₆H₁₁NO
| MolarMass =113.16 g/mol
| Appearance = white solid
| Density =
| MeltingPtC = 88 to 91
| MeltingPt_notes =
| BoilingPtC = 204 to 206
| BoilingPt_notes =
| Solubility = 16 g/kg (in water)
| MagSus = -71.52·10⁻⁶ cm³/mol
|Section3={{Chembox Hazards
| EUClass =Not available
| FlashPtC = 110
| AutoignitionPtC =
| SPhrases = {{S24/25}}
| ExternalSDS =
}}

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

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

References

1. ^¹J. 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}}

3 : Lactams|Monomers|Azepanes

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