Beckmann Rearrangement (Cyclohexanone Oxime)

cyclohexanone oxime → caprolactam

Overview

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.

Everyday Example

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

Industrial Importance

Over 5 million tonnes of caprolactam are produced annually by the Beckmann rearrangement for nylon 6 production. The entire nylon 6 industry depends on this reaction.

Properties

Type: Organic
Reversible: No
Energy: Exothermic
ΔH: -65.0 kJ/mol
Catalyst: H₂SO₄ or SO₃

Related Reactions

Aldol Condensation of Acetaldehyde Amide Formation (Acetic Acid + Ammonia) Baeyer-Villiger Oxidation Bromination of Ethylene Buchwald-Hartwig Amination Cannizzaro Reaction of Formaldehyde Catalytic Hydrogenation of Ethylene Claisen Condensation (Ethyl Acetate) Condensation Polymerization (Nylon 6,6) Cope Rearrangement

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).