Beckmann Rearrangement (Cyclohexanone Oxime)

cyclohexanone oxime → caprolactam

Tổng quan

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.

Ví dụ thực tế

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

Tầm quan trọng công nghiệp

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.

Tính chất

Loại: Organic
Thuận nghịch: Không
Năng lượng: Tỏa nhiệt
ΔH: -65,0 kJ/mol
Chất xúc tác: H₂SO₄ or SO₃

Phản ứng liên quan

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).