Selective Electrocatalytic Oxidation of Biomass‐Derived 5‐Hydroxymethylfurfural to 2, 5‐Diformylfuran: from Mechanistic Investigations to Catalyst Recovery

Kisszekelyi, Peter and Hardian, Rifan and Vovusha, Hakkim and Chen, Binglin and Zeng, Xianhai and Schwingenschlögl, Udo and Kupai, József and Székely, György (2020) Selective Electrocatalytic Oxidation of Biomass‐Derived 5‐Hydroxymethylfurfural to 2, 5‐Diformylfuran: from Mechanistic Investigations to Catalyst Recovery. ChemSusChem, 13 (12). pp. 3127-3136. ISSN 1864-5631

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Abstract

The catalytic transformation of bio-derived compounds, specifi-cally 5-hydroxymethylfurfural (HMF), into value-added chemi-cals may provide sustainable alternatives to crude oil andnatu-ral gas-based products. HMF can be obtained from fructoseand successfully converted to 2,5-diformylfuran (DFF) by an en-vironmentally friendlyorganic electrosynthesis performed in anElectraSyn reactor, using cost-effective and sustainable graph-ite (anode) and stainless-steel (cathode) electrodes in an undi-vided cell, eliminating the need for conventionalpreciousmetal electrodes. In this work, the electrocatalysis of HMF isperformed by using green solvents such as acetonitrile, g-vale-rolactone, as well as PolarClean, which is used in electrocataly-sis for the first time. The reaction parameters and the synergis-tic effects of the TEMPOcatalyst and2,6-lutidine base are ex-plored both experimentally and through computationmodel-ing. The molecular design and synthesis of asize-enlarged C3-symmetric tris-TEMPO catalystare also performed to facilitate asustainable reactionwork-up through nanofiltration. The ob-tained performanceisthen compared with those obtained byheterogeneous TEMPO alternatives recov ered by using an ex-ternal magnetic field and microf iltration. Resultsshow that thisnew methodofelectrocatalytic oxidation of HMF to DFF canbe achieved with excellent selectivity,good yield, and excellent catalyst recovery.

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