Beckmann Rearrangement (Cyclohexanone Oxime)

cyclohexanone oxime → caprolactam

概述

Cyclohexanone oxime undergoes acid-catalyzed Beckmann rearrangement to form caprolactam, expanding the six-membered ring to a seven-membered lactam. The anti group to the departing hydroxyl migrates to nitrogen. This is the key industrial step in nylon 6 production.

日常示例

The nylon in stockings, carpets, and ropes all comes from caprolactam made by this rearrangement reaction.

工业重要性

每年通过贝克曼重排生产超过500万吨己内酰胺,用于尼龙6的生产。整个尼龙6产业都依赖于这一反应。

属性

类型
Organic
可逆
否
能量
放热
ΔH
-65.0 kJ/mol
催化剂
H₂SO₄ or SO₃

相关反应

Swern Oxidation Oxidation of Secondary Alcohol to Ketone Claisen Condensation (Ethyl Acetate) Kolbe Electrolysis Baeyer-Villiger Oxidation Catalytic Hydrogenation of Ethylene Condensation Polymerization (Nylon 6,6) Cope Rearrangement Oxidation of Primary Alcohol to Aldehyde Epoxidation of Alkenes (mCPBA)

Frequently Asked Questions

What is the equation for Beckmann Rearrangement (Cyclohexanone Oxime)?
The balanced equation is: cyclohexanone oxime → caprolactam.
What type of reaction is Beckmann Rearrangement (Cyclohexanone Oxime)?
Beckmann Rearrangement (Cyclohexanone Oxime) is a organic reaction.
Is Beckmann Rearrangement (Cyclohexanone Oxime) exothermic or endothermic?
Beckmann Rearrangement (Cyclohexanone Oxime) is exothermic (releases energy). The enthalpy change (ΔH) is -65.0 kJ/mol.
What conditions are needed for Beckmann Rearrangement (Cyclohexanone Oxime)?
This reaction requires a catalyst (H₂SO₄ or SO₃).