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Organocatalyzed Beckmann rearrangement of cyclohexanone oxime by trifluoroacetic acid in aprotic solvent

Paper ID Volume ID Publish Year Pages File Format Full-Text
51630 46848 2008 6 PDF Available
Title
Organocatalyzed Beckmann rearrangement of cyclohexanone oxime by trifluoroacetic acid in aprotic solvent
Abstract

The Beckmann rearrangement of cyclohexanone oxime to ε-caprolactam catalyzed by trifluoroacetic acid in aprotic solvents such as toluene, 1,2-dichloroethane, acetonitrile, benzonitrile, nitromethane and their mixtures is described. High yield and selectivity in ε-caprolactam have been observed. Data relative to cyclohexanone oxime protonation equilibrium, interaction of ε-caprolactam with the acid, solvent effect on reaction kinetics and apparent activation energy are given together with some thoughts on the reaction mechanism.

Keywords
Beckmann rearrangement; Caprolactam; Organocatalysis; Trifluoroacetic acid
First Page Preview
Organocatalyzed Beckmann rearrangement of cyclohexanone oxime by trifluoroacetic acid in aprotic solvent
Publisher
Database: Elsevier - ScienceDirect
Journal: Catalysis Communications - Volume 10, Issue 2, 15 November 2008, Pages 251–256
Authors
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Subjects
Physical Sciences and Engineering Chemical Engineering Catalysis