Beckmann Rearrangement (Cyclohexanone Oxime)

cyclohexanone oxime → caprolactam

개요

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.

일상 속 예시

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

산업적 중요성

나일론 6 생산을 위해 베크만 자리옮김으로 매년 500만 톤 이상의 카프로락탐이 생산됩니다. 전체 나일론 6 산업이 이 반응에 의존하고 있습니다.

성질

유형
Organic
가역 반응
아니오
에너지
발열
ΔH
-65.0 kJ/mol
촉매
H₂SO₄ or SO₃

관련 반응

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).