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

Epoxidation of Alkenes (mCPBA) Swern Oxidation Oxidation of Secondary Alcohol to Ketone E2 Elimination (Dehydrohalogenation) Claisen Condensation (Ethyl Acetate) Aldol Condensation of Acetaldehyde Kolbe Electrolysis Baeyer-Villiger Oxidation Catalytic Hydrogenation of Ethylene Dehydration of Ethanol

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).