Beckmann Rearrangement (Cyclohexanone Oxime)

cyclohexanone oxime → caprolactam

Visão geral

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.

Exemplo do cotidiano

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

Importância industrial

São produzidos anualmente mais de 5 milhões de toneladas de caprolactama pelo rearranjo de Beckmann para a produção de nylon 6. Toda a indústria do nylon 6 depende desta reação.

Propriedades

Tipo: Organic
Reversível: Não
Energia: Exotérmico
ΔH: -65,0 kJ/mol
Catalisador: H₂SO₄ or SO₃

Reações relacionadas

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).