Beckmann Rearrangement (Cyclohexanone Oxime)

cyclohexanone oxime → caprolactam

概要

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.

日常の例

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

産業上の重要性

ベックマン転位により年間500万トン以上のカプロラクタムがナイロン6生産のために生産されています。ナイロン6産業全体がこの反応に依存しています。

特性

タイプ
Organic
可逆的
いいえ
エネルギー
発熱性
ΔH
-65.0 kJ/mol
触媒
H₂SO₄ or SO₃

関連する反応

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).