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

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).