β-Cyclodextrins modified by alkyl and poly(ethylene oxide) chains: A novel class of mass transfer additives for aqueous organometallic catalysis

A novel class of β-cyclodextrins (β-CDs) bearing alkyl chains on the secondary face and poly(ethylene oxide) chains on the primary face was synthesized. Their interactions with two water-soluble derivatives of triphenylphosphane were investigated by 31P{1H} and 1H NMR. Their behaviour in rhodium-catalysed biphasic hydroformylation of 1-decene was evaluated and the best result was obtained with a β-CD bearing methyl groups on the secondary face and poly(ethylene oxide) chains on the primary face. This CD appeared to be more efficient than randomly methylated β-CD which is currently one of the best mass transfer additives for hydroformylation.

Graphical abstractA novel class of β-CDs bearing alkyl chains on the secondary face and poly(ethylene oxide) chains on the primary face was synthesized and their behaviour in rhodium-catalysed biphasic hydroformylation of 1-decene was evaluated. High conversion and selectivities were obtained with a β-CD bearing methyl group on the secondary face and PEO chains on the primary face.Figure optionsDownload full-size imageDownload high-quality image (84 K)Download as PowerPoint slide