Homogeneous liquid-phase Beckmann rearrangement of oxime catalyzed by phosphorous pentaoxide and accelerated by fluorine-containing strong acid

被引：33

作者：

Sato, H

Yoshioka, H

Izumi, Y

机构：

[1] Sumitomo Chem Co Ltd, Basic Chem Res Lab, Niihama, Ehime 792, Japan

[2] Sugiyama Women Courage, Dept Life Sci, Nagoya, Aichi 464, Japan

来源：

JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL | 1999年 / 149卷 / 1-2期

关键词：

Beckmann rearrangement (homogeneous liquid phase); catalyst; phosphorous pentaoxide; trifluoromethanesulfonic acid; cyclohexanone oxime; epsilon-caprolactam; DMF (solvent);

D O I：

10.1016/S1381-1169(99)00170-3

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

Phosphorous pentaoxide (P2O5) effectively catalyzed homogeneous liquid-phase Beckmann rearrangement of cyclohexanone oxime to epsilon-caprolactam in N,N-dimethylformamide (DMF). The turn-over number (TON) of P2O5 was 20. The catalytic activity was greatly increased by addition of a co-catalyst, trifluoromethane sulfonic acid, and the TON was increased to 100. The catalyst system was successfully applied to other ketoximes such as acetone oxime, acetophenone oxime, and cyclopentanone oxime. A strongly polarized pseudo-iminium cation was proposed as an active species. (C) 1999 Elsevier Science B.V. All rights reserved.

引用

页码：25 / 32

页数：8

共 27 条

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