Challenges of Green Production of 2,5-Furandicarboxylic Acid from Bio-Derived 5-Hydroxymethylfurfural: Overcoming Deactivation by Concomitant Amino Acids

Overview

Journal ChemSusChem

Specialty Chemistry

Date 2022 Apr 19

PMID 35439346

Authors

Dominik Neukum

Lorena Baumgarten

Dominik Wust

Bidyut Bikash Sarma

Erisa Saraci

Andrea Kruse

Jan-Dierk Grunwaldt

Affiliations

Soon will be listed here.

Abstract

The oxidation of 5-hydroxymethylfurfural (HMF) to 2,5-furandicarboxylic acid (FDCA) is highly attractive as FDCA is considered as substitute for the petrochemically derived terephthalic acid. There are only few reports on the direct use of unrefined HMF solutions from biomass resources and the influence of remaining constituents on the catalytic processes. In this work, the oxidation of HMF in a solution as obtained from hydrolysis and dehydration of saccharides in chicory roots was investigated without intermediate purification steps. The amount of base added to the solution was critical to increase the FDCA yield. Catalyst deactivation occurred and was attributed to poisoning by amino acids from the bio-source. A strong influence of amino acids on the catalytic activity was found for all supported Au, Pt, Pd, and Ru catalysts. A supported AuPd(2 : 1)/C alloy catalyst exhibited both superior catalytic activity and higher stability against deactivation by the critical amino acids.

Citing Articles

Challenges of Green Production of 2,5-Furandicarboxylic Acid from Bio-Derived 5-Hydroxymethylfurfural: Overcoming Deactivation by Concomitant Amino Acids.

Neukum D, Baumgarten L, Wust D, Sarma B, Saraci E, Kruse A ChemSusChem. 2022; 15(13):e202200418.

PMID: 35439346 PMC: 9400955. DOI: 10.1002/cssc.202200418.

References

Vericat C, Vela M, Benitez G, Carro P, Salvarezza R . Self-assembled monolayers of thiols and dithiols on gold: new challenges for a well-known system. Chem Soc Rev. 2010; 39(5):1805-34. DOI: 10.1039/b907301a. View

Casanova O, Iborra S, Corma A . Biomass into chemicals: aerobic oxidation of 5-hydroxymethyl-2-furfural into 2,5-furandicarboxylic acid with gold nanoparticle catalysts. ChemSusChem. 2009; 2(12):1138-44. DOI: 10.1002/cssc.200900137. View

Artz J, Palkovits R . Base-Free Aqueous-Phase Oxidation of 5-Hydroxymethylfurfural over Ruthenium Catalysts Supported on Covalent Triazine Frameworks. ChemSusChem. 2015; 8(22):3832-8. DOI: 10.1002/cssc.201501106. View

Llevot A, Dannecker P, von Czapiewski M, Over L, Soyler Z, Meier M . Renewability is not Enough: Recent Advances in the Sustainable Synthesis of Biomass-Derived Monomers and Polymers. Chemistry. 2016; 22(33):11510-21. DOI: 10.1002/chem.201602068. View

Deshan A, Atanda L, Moghaddam L, Rackemann D, Beltramini J, Doherty W . Heterogeneous Catalytic Conversion of Sugars Into 2,5-Furandicarboxylic Acid. Front Chem. 2020; 8:659. PMC: 7413130. DOI: 10.3389/fchem.2020.00659. View

Abraham A, Ilott A, Miller J, Gullion T . (1)H MAS NMR study of cysteine-coated gold nanoparticles. J Phys Chem B. 2012; 116(27):7771-5. DOI: 10.1021/jp3011298. View

Lee Y, Kim M, Kim Z, Han S . One-step synthesis of Au@Pd core-shell nanooctahedron. J Am Chem Soc. 2009; 131(47):17036-7. DOI: 10.1021/ja905603p. View

Ardemani L, Cibin G, Dent A, Isaacs M, Kyriakou G, Lee A . Solid base catalysed 5-HMF oxidation to 2,5-FDCA over Au/hydrotalcites: fact or fiction?. Chem Sci. 2018; 6(8):4940-4945. PMC: 6088438. DOI: 10.1039/c5sc00854a. View

Galkin K, Krivodaeva E, Romashov L, Zalesskiy S, Kachala V, Burykina J . Critical Influence of 5-Hydroxymethylfurfural Aging and Decomposition on the Utility of Biomass Conversion in Organic Synthesis. Angew Chem Int Ed Engl. 2016; 55(29):8338-42. DOI: 10.1002/anie.201602883. View

10.

Neukum D, Baumgarten L, Wust D, Sarma B, Saraci E, Kruse A . Challenges of Green Production of 2,5-Furandicarboxylic Acid from Bio-Derived 5-Hydroxymethylfurfural: Overcoming Deactivation by Concomitant Amino Acids. ChemSusChem. 2022; 15(13):e202200418. PMC: 9400955. DOI: 10.1002/cssc.202200418. View

11.

Zhu L, Fu X, Hu Y, Hu C . Controlling the Reaction Networks for Efficient Conversion of Glucose into 5-Hydroxymethylfurfural. ChemSusChem. 2020; 13(18):4812-4832. DOI: 10.1002/cssc.202001341. View

12.

Ke S, Qiu L, Zhao W, Sun C, Cui B, Xu G . Understanding of Correlation between Electronic Properties and Sulfur Tolerance of Pt-Based Catalysts for Hydrogen Oxidation. ACS Appl Mater Interfaces. 2022; 14(6):7768-7778. DOI: 10.1021/acsami.1c18905. View

13.

Friedman M . Applications of the ninhydrin reaction for analysis of amino acids, peptides, and proteins to agricultural and biomedical sciences. J Agric Food Chem. 2004; 52(3):385-406. DOI: 10.1021/jf030490p. View

14.

Motagamwala A, Won W, Sener C, Alonso D, Maravelias C, Dumesic J . Toward biomass-derived renewable plastics: Production of 2,5-furandicarboxylic acid from fructose. Sci Adv. 2018; 4(1):eaap9722. PMC: 5775026. DOI: 10.1126/sciadv.aap9722. View

15.

Wangoo N, Bhasin K, Mehta S, Suri C . Synthesis and capping of water-dispersed gold nanoparticles by an amino acid: bioconjugation and binding studies. J Colloid Interface Sci. 2008; 323(2):247-54. DOI: 10.1016/j.jcis.2008.04.043. View

16.

Kim M, Su Y, Fukuoka A, Hensen E, Nakajima K . Aerobic Oxidation of 5-(Hydroxymethyl)furfural Cyclic Acetal Enables Selective Furan-2,5-dicarboxylic Acid Formation with CeO -Supported Gold Catalyst. Angew Chem Int Ed Engl. 2018; 57(27):8235-8239. DOI: 10.1002/anie.201805457. View

17.

Villa A, Schiavoni M, Campisi S, Veith G, Prati L . Pd-modified Au on carbon as an effective and durable catalyst for the direct oxidation of HMF to 2,5-furandicarboxylic acid. ChemSusChem. 2013; 6(4):609-12. DOI: 10.1002/cssc.201200778. View

18.

Megias-Sayago C, Bonincontro D, Lolli A, Ivanova S, Albonetti S, Cavani F . 5-Hydroxymethyl-2-Furfural Oxidation Over Au/CeZrO Catalysts. Front Chem. 2020; 8:461. PMC: 7287476. DOI: 10.3389/fchem.2020.00461. View

19.

Ravel B, Newville M . ATHENA, ARTEMIS, HEPHAESTUS: data analysis for X-ray absorption spectroscopy using IFEFFIT. J Synchrotron Radiat. 2005; 12(Pt 4):537-41. DOI: 10.1107/S0909049505012719. View

20.

Gao F, Goodman D . Pd-Au bimetallic catalysts: understanding alloy effects from planar models and (supported) nanoparticles. Chem Soc Rev. 2012; 41(24):8009-20. DOI: 10.1039/c2cs35160a. View