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

The catalytic transformation of bio‐derived compounds, specifically 5‐hydroxymethylfurfural (HMF), into value‐added chemicals may provide sustainable alternatives to crude oil and natural gas‐based products. HMF can be obtained from fructose and successfully converted to 2,5‐diformylfuran (DFF) by a...

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Autores principales: Kisszekelyi, Peter, Hardian, Rifan, Vovusha, Hakkim, Chen, Binglin, Zeng, Xianhai, Schwingenschlögl, Udo, Kupai, Jozsef, Szekely, Gyorgy
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2020
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7318667/
https://www.ncbi.nlm.nih.gov/pubmed/32338429
http://dx.doi.org/10.1002/cssc.202000453
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author Kisszekelyi, Peter
Hardian, Rifan
Vovusha, Hakkim
Chen, Binglin
Zeng, Xianhai
Schwingenschlögl, Udo
Kupai, Jozsef
Szekely, Gyorgy
author_facet Kisszekelyi, Peter
Hardian, Rifan
Vovusha, Hakkim
Chen, Binglin
Zeng, Xianhai
Schwingenschlögl, Udo
Kupai, Jozsef
Szekely, Gyorgy
author_sort Kisszekelyi, Peter
collection PubMed
description The catalytic transformation of bio‐derived compounds, specifically 5‐hydroxymethylfurfural (HMF), into value‐added chemicals may provide sustainable alternatives to crude oil and natural gas‐based products. HMF can be obtained from fructose and successfully converted to 2,5‐diformylfuran (DFF) by an environmentally friendly organic electrosynthesis performed in an ElectraSyn reactor, using cost‐effective and sustainable graphite (anode) and stainless‐steel (cathode) electrodes in an undivided cell, eliminating the need for conventional precious metal electrodes. In this work, the electrocatalysis of HMF is performed by using green solvents such as acetonitrile, γ‐valerolactone, as well as PolarClean, which is used in electrocatalysis for the first time. The reaction parameters and the synergistic effects of the TEMPO catalyst and 2,6‐lutidine base are explored both experimentally and through computation modeling. The molecular design and synthesis of a size‐enlarged C (3)‐symmetric tris‐TEMPO catalyst are also performed to facilitate a sustainable reaction work‐up through nanofiltration. The obtained performance is then compared with those obtained by heterogeneous TEMPO alternatives recovered by using an external magnetic field and microfiltration. Results show that this new method of electrocatalytic oxidation of HMF to DFF can be achieved with excellent selectivity, good yield, and excellent catalyst recovery.
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spelling pubmed-73186672020-06-29 Selective Electrocatalytic Oxidation of Biomass‐Derived 5‐Hydroxymethylfurfural to 2,5‐Diformylfuran: from Mechanistic Investigations to Catalyst Recovery Kisszekelyi, Peter Hardian, Rifan Vovusha, Hakkim Chen, Binglin Zeng, Xianhai Schwingenschlögl, Udo Kupai, Jozsef Szekely, Gyorgy ChemSusChem Full Papers The catalytic transformation of bio‐derived compounds, specifically 5‐hydroxymethylfurfural (HMF), into value‐added chemicals may provide sustainable alternatives to crude oil and natural gas‐based products. HMF can be obtained from fructose and successfully converted to 2,5‐diformylfuran (DFF) by an environmentally friendly organic electrosynthesis performed in an ElectraSyn reactor, using cost‐effective and sustainable graphite (anode) and stainless‐steel (cathode) electrodes in an undivided cell, eliminating the need for conventional precious metal electrodes. In this work, the electrocatalysis of HMF is performed by using green solvents such as acetonitrile, γ‐valerolactone, as well as PolarClean, which is used in electrocatalysis for the first time. The reaction parameters and the synergistic effects of the TEMPO catalyst and 2,6‐lutidine base are explored both experimentally and through computation modeling. The molecular design and synthesis of a size‐enlarged C (3)‐symmetric tris‐TEMPO catalyst are also performed to facilitate a sustainable reaction work‐up through nanofiltration. The obtained performance is then compared with those obtained by heterogeneous TEMPO alternatives recovered by using an external magnetic field and microfiltration. Results show that this new method of electrocatalytic oxidation of HMF to DFF can be achieved with excellent selectivity, good yield, and excellent catalyst recovery. John Wiley and Sons Inc. 2020-06-02 2020-06-19 /pmc/articles/PMC7318667/ /pubmed/32338429 http://dx.doi.org/10.1002/cssc.202000453 Text en © 2020 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the http://creativecommons.org/licenses/by/4.0/ License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
spellingShingle Full Papers
Kisszekelyi, Peter
Hardian, Rifan
Vovusha, Hakkim
Chen, Binglin
Zeng, Xianhai
Schwingenschlögl, Udo
Kupai, Jozsef
Szekely, Gyorgy
Selective Electrocatalytic Oxidation of Biomass‐Derived 5‐Hydroxymethylfurfural to 2,5‐Diformylfuran: from Mechanistic Investigations to Catalyst Recovery
title Selective Electrocatalytic Oxidation of Biomass‐Derived 5‐Hydroxymethylfurfural to 2,5‐Diformylfuran: from Mechanistic Investigations to Catalyst Recovery
title_full Selective Electrocatalytic Oxidation of Biomass‐Derived 5‐Hydroxymethylfurfural to 2,5‐Diformylfuran: from Mechanistic Investigations to Catalyst Recovery
title_fullStr Selective Electrocatalytic Oxidation of Biomass‐Derived 5‐Hydroxymethylfurfural to 2,5‐Diformylfuran: from Mechanistic Investigations to Catalyst Recovery
title_full_unstemmed Selective Electrocatalytic Oxidation of Biomass‐Derived 5‐Hydroxymethylfurfural to 2,5‐Diformylfuran: from Mechanistic Investigations to Catalyst Recovery
title_short Selective Electrocatalytic Oxidation of Biomass‐Derived 5‐Hydroxymethylfurfural to 2,5‐Diformylfuran: from Mechanistic Investigations to Catalyst Recovery
title_sort selective electrocatalytic oxidation of biomass‐derived 5‐hydroxymethylfurfural to 2,5‐diformylfuran: from mechanistic investigations to catalyst recovery
topic Full Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7318667/
https://www.ncbi.nlm.nih.gov/pubmed/32338429
http://dx.doi.org/10.1002/cssc.202000453
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