Mechanism into selective oxidation of cinnamaldehyde using β-cyclodextrin polymer as phase-transfer catalyst

Selective oxidation of cinnamaldehyde to benzaldehyde in the presence of bicarbonate and hydrogen peroxide and catalyzed by β-cyclodextrin polymer (β-CDP) was investigated. β-CDP was utilized as the phase-transfer catalyst in this study. The immobilized β-cyclodextrin possessing a hydrophobic host cavity was found to be efficient as mass-transfer promoters for the oxidation of cinnamaldehyde. Benzaldehyde could be obtained in 63% yield under optimal reaction conditions. The results indicate the complex formed between cinnamaldehyde and β-CDP via the intermolecular weak interactions, e.g., hydrogen bond was the reason why the conversion and selectivity could be significantly promoted. Finally, the reusability of the catalyst was also evaluated. Its catalytic activity remained unchanged even after recycled for six times, which suggests it is an efficient catalyst for oxidation of cinnamaldehyde.

Graphical abstractDownload full-size imageSelective oxidation of cinnamaldehyde to benzaldehyde using β-cyclodextrin polymer as phase-transfer catalyst was studied. The improved efficiency of mass transfer via the intermolecular weak interactions, e.g., hydrogen bond was the reason why conversion and selectivity could be significantly promoted. The catalyst could be facilely isolated from the reaction mixture, and could be reused without significant loss in activity.