Selective catalytic oxidation of cyclohexylbenzene to cyclohexylbenzene-1-hydroperoxide:: a coproduct-free route to phenol

被引：70

作者：

Arends, IWCE

Sasidharan, M

Kühnle, A

Duda, M

Jost, C

Sheldon, RA

机构：

[1] Delft Univ Technol, Dept Biotechnol, Lab Biocatalysis & Organ Chem, NL-2628 BL Delft, Netherlands

[2] CREAVIS Gesellschaft Technol & Innovat mbH, D-45764 Marl, Germany

来源：

TETRAHEDRON | 2002年 / 58卷 / 44期

关键词：

autoxidation; cyclobexylbenzene; phenol; N-hydroxyphthalimide;

D O I：

10.1016/S0040-4020(02)01131-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A method is described for the highly selective oxidation of cyclohexylbenzene to cyclohexylbenzene-1-hydroperoxide. In the presence of 0.5 mol% N-hydroxyphthalimide (NHPI) and 2 mol% of the hydroperoxide product, without solvent, a selectivity of ca. 98% to the desired product was obtained at 32% conversion. The use of NHPI increases the selectivity for initial H-abstraction from the 1-position, vs the other positions in the cyclohexyl ring, suppresses byproduct formation via transannular hydrogen abstraction and increases the overall rate of reaction. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：9055 / 9061

页数：7

共 24 条

[21] SELECTIVITY TO CYCLOHEXENES IN THE LIQUID-PHASE HYDROGENATION OF BENZENE AND TOLUENE OVER RUTHENIUM CATALYSTS, AS INFLUENCED BY REACTION MODIFIERS [J].