Journal of Synthetic Organic Chemistry, Japan
Online ISSN : 1883-6526
Print ISSN : 0037-9980
ISSN-L : 0037-9980
Direct Preparation of .A-Caprolactam using Nitroparaffin as a Source of Hydroxylamine.
Chikai KIMURAKageaki KASHIWAYAToshiharu NAYA
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1965 Volume 23 Issue 3 Pages 254-258

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Abstract
An attempt was made to synthesize .ε-caprolactam directly from cyclohexanoneand a primary nitroparaffin, the latter being used as a source of hydroxylamine. When nitromethane, nitroethane, or nitropropane was treated with sulfuric acid in a molar ratio of 1:5 at 125-130°C, hydroxylamine sulfate was formed in a yield above 90%. The reaction mixture thus prepared was then treated with cyclohexanone at 120-125°C. Oxime formation and the Beckmann rearrangement proceeded smoothly, and .ε-caprolactam was obtained in a good yield.
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© The Society of Syhthetic Organic Chemistry, Japan
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