Continuous Synthesis of Epoxides from Alkenes by Hydrogen Peroxide with Titanium Silicalite‐1 Catalyst Using Flow Reactors

Author:

Kon Yoshihiro1ORCID,Nakashima Takuya1,Makino Yoshiki2,Nagashima Hiroki1,Onozawa Shun‐ya1,Kobayashi Shū13ORCID,Sato Kazuhiko1

Affiliation:

1. Interdisciplinary Research Center for Catalytic Chemistry National Institute of Advanced Industrial Science and Technology (AIST) 305-8565 Tsukuba Ibaraki Japan

2. Environmental Management Research Institute National Institute of Advanced Industrial Science and Technology (AIST) AIST Tsukuba West, 16-1, Onogawa 305-8569 Tsukuba Ibaraki Japan

3. Department of Chemistry School of Science The University of Tokyo Hongo, Bunkyo-ku 113-0033 Tokyo Japan

Abstract

AbstractAbstract. Continuous‐flow epoxidation of aliphatic and aromatic alkenes with hydrogen peroxide (H2O2) was carried out to give epoxides using a fixed‐bed liquid flow reactor equipped with a solid titanium silicalite‐1 (TS‐1) catalyst column. The developed flow reaction enables continuous synthesis of 4‐phenyl‐1,2‐epoxybutane from 4‐phenyl‐1‐butene in 90%–98% yields (22.4 g) for 150 h from a catalyst column of 5 mm inner diameter with 100 mm length. Employment of a mixed solution of MeCN and MeOH with preservation of the Ti active site in TS‐1 crystal structures with few defects permits continuous epoxidation of less‐reactive long‐chain terminal alkene and multifunctional alkene to give epoxides in 12%–98% yields with 78%–99% selectivity.

Publisher

Wiley

Subject

Organic Chemistry,Catalysis

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