Mediator-assisted selective oxidation of 5-hydroxymethylfurfural to 2.5-diformylfuran in the presence of collidine

Abstract

Mediator-assisted selective oxidation of 5-hydroxymethylfurfural to 2.5-diformylfuran in the presence of collidine

Kashparova V.P., Leontyeva D.V., Klushin V.A., Zhukova I.Yu., Smirnova N.V.

Incoming article date: 28.10.2016

The process of 4-acetylamino-2,2,6,6-tetramethylpiperidine-1-oxyl/I2 mediated oxidation of 5-hydroxylmethylfurfural in a twophase system consisting of a methylene chloride and aqueous solution containing sodium hydrogen carbonate was investigated. It was shown that the introduction into the reaction system collidine provides selective oxidation of 5-hydroxymethylfurfural to 2,5-diformylfuran (yield 99% at a selectivity of 100%).The optimal composition of the system and the optimal conditions of synthesis were determined. A mechanism of promoting the oxidation of the OH- group of 5-hydroxymethylfurfural and protecting the further oxidation of 2,5-diformylfuran by collidine was proposed.

Keywords: 5-hydroxymethylfurfural, 2,5-diformylfuran, nitroxyl radical, collidine