Rhodium-Catalyzed Aqueous Biphasic Olefin Hydroformylation Promoted by Amphiphilic Cyclodextrins

Aurélien Cocq,Sébastien Tilloy,Hervé Bricout,Florence Djedaïni-Pilard,Eric Monflier

doi:10.3390/catal10010056

Abstract

Hydroformylation is an industrial process that allows for the production of aldehydes from alkenes using transition metals. The reaction can be carried out in water, and the catalyst may be recycled at the end of the reaction. The industrial application of rhodium-catalyzed aqueous hydroformylation has been demonstrated for smaller olefins (propene and butene). Unfortunately, larger olefins are weakly soluble in water, which results in very low catalytic activity. In an attempt to counteract this, we investigated the use of amphiphilic oleic succinyl-cyclodextrins (OS-CDs) synthesized from oleic acid derivatives and maleic anhydride. OS-CDs were found to increase the catalytic activity of rhodium during the hydroformylation of water-insoluble olefins, such as 1-decene and 1-hexadecene, by promoting mass transfer. Recyclability of the catalytic system was also evaluated in the presence of these cyclodextrins.

Highlights

Cyclodextrins (CDs) are cyclic oligosaccharides consisting of six (α-CD), seven (β-CD), or eight (γ-CD) α-D-glucopyranose units [1,2]
We evaluated the behavior of amphiphilic oleic succinyl-CDs (OS-CDs) olefins with multivalent interactions [15]
We evaluated the behavior of amphiphilic synthesized from oleic acid derivatives and maleic anhydride in an aqueous hydroformylation reaction oleic succinyl-CDs (OS-CDs) synthesized from oleic acid derivatives and maleic anhydride in an

Summary

Introduction

Cyclodextrins (CDs) are cyclic oligosaccharides consisting of six (α-CD), seven (β-CD), or eight (γ-CD) α-D-glucopyranose units [1,2]. The inner surface forms a cavity and allows for the formation of an inclusion complex when it binds a hydrophobic substrate To vary their size and shape, native CDs can be modified by substituting their hydroxyl groups with various other functional groups. In the field of aqueous biphasic organometallic catalysis, CDs have mainly been employed as platforms for the production of water-soluble ligands using transition metals [4,5,6,7,8,9,10,11,12,13] They have been used as mass-transfer agents in order to increase the solubility of hydrophobic substrates in water [14,15]. Increases in catalytic potential were especially high for hydrophobic substrates, which shows the beneficial effect of CDs on mass transfer at the aqueous–organic interface

Methods

Results

Conclusion