Aerobic Oxidation of 5-(Hydroxymethyl)furfural Cyclic Acetal Enables Selective Furan-2,5-dicarboxylic Acid Formation with CeO2 -Supported Gold Catalyst

Angewandte Chemie
Minjune KimKiyotaka Nakajima

Abstract

The utilization of 5-(hydroxymethyl)furfural (HMF) for the large-scale production of essential chemicals has been largely limited by the formation of solid humin as a byproduct, which prevents the operation of stepwise batch-type and continuous flow-type processes. The reaction of HMF with 1,3-propanediol produces an HMF acetal derivative that exhibits excellent thermal stability. Aerobic oxidation of the HMF acetal with a CeO2 -supported Au catalyst and Na2 CO3 in water gives a 90-95 % yield of furan 2,5-dicarboxylic acid, an increasingly important commodity chemical for the biorenewables industry, from concentrated solutions (10-20 wt %) without humin formation. The six-membered acetal ring suppresses thermal decomposition and self-polymerization of HMF in concentrated solutions. Kinetic studies supported by DFT calculations identify two crucial steps in the reaction mechanism, that is, the partial hydrolysis of the acetal into 5-formyl-2-furan carboxylic acid involving OH- and Lewis acid sites on CeO2 , and subsequent oxidative dehydrogenation of the in situ generated hemiacetal involving Au nanoparticles. These results represent a significant advance over the current state of the art, overcoming an inherent limitation of th...Continue Reading

References

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Feb 12, 2013·Chemical Reviews·Robert-Jan van PuttenJohannes G de Vries

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Citations

Mar 19, 2019·Angewandte Chemie·Zhifei HaoSihui Zhan
May 23, 2019·ChemSusChem·Konstantin I Galkin, Valentine P Ananikov
Dec 24, 2019·ACS Applied Materials & Interfaces·Masanori NagaoYuichi Kamiya
Jan 8, 2019·Journal of the American Chemical Society·Eri HayashiMichikazu Hara
Dec 7, 2021·Frontiers in Chemistry·Federico A BertoliniAlessandro Pellis

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