Epoxidation of cyclooctene and cyclohexene with hydrogen peroxide catalyzed by bis[3,5-bis(trifluoromethyl)-diphenyl] diselenide: Recyclable catalyst-containing phases through the use of glycerol-derived solvents

A green strategy has been explored for olefin epoxidation which combines renewable solvents (derived from glycerol), aqueous hydrogen peroxide, and catalyst recycling (a seleninic acid derivative). The use of fluorinated glycerol derivatives allows good catalytic activity in the epoxidation of cyclooctene and cyclohexene with aqueous hydrogen peroxide, preventing epoxide hydrolysis to a great extent, which is particularly remarkable in the case of cyclohexene. Furthermore, recycling of the catalytically active phase is possible through distillation of the cyclohexene oxide from the reaction mixture, which can be subsequently recharged with fresh oxidant and substrate. © 2010 Elsevier B.V. All rights reserved.Financial support from the European Union (project Solvsafe, NMP2-CT-2005-011774 and the European Social Fund), the Spanish MCIMM (projects CTQ2008-05138 and Consolider Ingenio 2010 CSD 2006-0003) and the Gobierno de Aragón (Grupo de Excelencia E11) is gratefully acknowledged. H. García-Marín thanks the Gobierno de Aragón and Caja de Ahorros de la Inmaculada for grants.Peer Reviewe