Operando Generated Copper-based Catalyst Enabling Efficient Electrosynthesis of 2,5-bis(hydroxymethyl)furan

Overview

Journal Fundam Res

Date 2024 Jun 27

PMID 38933290

Authors

Zhaolu Zhang

Kai Huang

Xinyue Qiu

Wangxin Ge

Xiaoling Yang

Yihua Zhu

Cheng Lian

Honglai Liu

Hongliang Jiang

Chunzhong Li

Affiliations

Soon will be listed here.

Abstract

Electrocatalytic upgrading of biomass-derived platform molecules has emerged as a sustainable and environmentally benign route to produce high-value chemicals. The main challenge lies in developing efficient catalysts for the selective activation of designated chemical bonds in the presence of various reducible groups. This work demonstrated a high-efficiency electrochemical conversion of 5-hydroxymethylfurfural (HMF) to 2,5-bis(hydroxymethyl)furan (BHMF), an important industrial synthetic reagent. A highly porous Cu-based catalyst was developed that achieved nearly 100% BHMF selectivity and long-term stability. Through comprehensive operando and ex-situ structural characterizations, an electrochemically generated catalyst with abundant Cu/CuO interfaces was identified as a catalytically active phase for HMF conversion. Deuterated BHMF, with the potential to produce deuterated drugs, was also synthesized using DO as the deuterium source. Density functional theory calculations show that the Cu/CuO interface structure exhibits relatively low energy barriers for the hydrogenation of HMF to BHMF. This work provides insights into the origin of electrocatalytic hydrogenation activity and highlights the promising potential of the electrocatalytic synthesis of high-value chemicals.

References

Huang J, Zhao S, Chen W, Zhou Y, Yang X, Zhu Y . Three-dimensionally grown thorn-like Cu nanowire arrays by fully electrochemical nanoengineering for highly enhanced hydrazine oxidation. Nanoscale. 2015; 8(11):5810-4. DOI: 10.1039/c5nr06512g. View

Pang R, Tian P, Jiang H, Zhu M, Su X, Wang Y . Tracking structural evolution: regenerative CeO/Bi interface structure for high-performance CO electroreduction. Natl Sci Rev. 2021; 8(7):nwaa187. PMC: 8310765. DOI: 10.1093/nsr/nwaa187. View

Xu C, Paone E, Rodriguez-Padron D, Luque R, Mauriello F . Recent catalytic routes for the preparation and the upgrading of biomass derived furfural and 5-hydroxymethylfurfural. Chem Soc Rev. 2020; 49(13):4273-4306. DOI: 10.1039/d0cs00041h. View

Chadderdon X, Chadderdon D, Matthiesen J, Qiu Y, Carraher J, Tessonnier J . Mechanisms of Furfural Reduction on Metal Electrodes: Distinguishing Pathways for Selective Hydrogenation of Bioderived Oxygenates. J Am Chem Soc. 2017; 139(40):14120-14128. DOI: 10.1021/jacs.7b06331. View

Suastegui M, Matthiesen J, Carraher J, Hernandez N, Rodriguez Quiroz N, Okerlund A . Combining Metabolic Engineering and Electrocatalysis: Application to the Production of Polyamides from Sugar. Angew Chem Int Ed Engl. 2016; 55(7):2368-73. DOI: 10.1002/anie.201509653. View

Akhade S, Singh N, Gutierrez O, Lopez-Ruiz J, Wang H, Holladay J . Electrocatalytic Hydrogenation of Biomass-Derived Organics: A Review. Chem Rev. 2020; 120(20):11370-11419. DOI: 10.1021/acs.chemrev.0c00158. View

Jiang H, He Q, Zhang Y, Song L . Structural Self-Reconstruction of Catalysts in Electrocatalysis. Acc Chem Res. 2018; 51(11):2968-2977. DOI: 10.1021/acs.accounts.8b00449. View

Kresse , Furthmuller . Efficient iterative schemes for ab initio total-energy calculations using a plane-wave basis set. Phys Rev B Condens Matter. 1996; 54(16):11169-11186. DOI: 10.1103/physrevb.54.11169. View

Xia R, Tian D, Kattel S, Hasa B, Shin H, Ma X . Electrochemical reduction of acetonitrile to ethylamine. Nat Commun. 2021; 12(1):1949. PMC: 8007591. DOI: 10.1038/s41467-021-22291-0. View

10.

Tan J, Zhang W, Shu Y, Lu H, Tang Y, Gao Q . Interlayer engineering of molybdenum disulfide toward efficient electrocatalytic hydrogenation. Sci Bull (Beijing). 2023; 66(10):1003-1012. DOI: 10.1016/j.scib.2020.11.002. View

11.

Blochl . Projector augmented-wave method. Phys Rev B Condens Matter. 1994; 50(24):17953-17979. DOI: 10.1103/physrevb.50.17953. View

12.

Wu Y, Liu C, Wang C, Lu S, Zhang B . Selective Transfer Semihydrogenation of Alkynes with H O (D O) as the H (D) Source over a Pd-P Cathode. Angew Chem Int Ed Engl. 2020; 59(47):21170-21175. DOI: 10.1002/anie.202009757. View

13.

Wang Y, Zhou W, Jia R, Yu Y, Zhang B . Unveiling the Activity Origin of a Copper-based Electrocatalyst for Selective Nitrate Reduction to Ammonia. Angew Chem Int Ed Engl. 2020; 59(13):5350-5354. DOI: 10.1002/anie.201915992. View

14.

Jiang H, He Q, Li X, Su X, Zhang Y, Chen S . Tracking Structural Self-Reconstruction and Identifying True Active Sites toward Cobalt Oxychloride Precatalyst of Oxygen Evolution Reaction. Adv Mater. 2019; 31(8):e1805127. DOI: 10.1002/adma.201805127. View

15.

Perdew , Burke , Ernzerhof . Generalized Gradient Approximation Made Simple. Phys Rev Lett. 1996; 77(18):3865-3868. DOI: 10.1103/PhysRevLett.77.3865. View

16.

van Putten R, van der Waal J, de Jong E, Rasrendra C, Heeres H, de Vries J . Hydroxymethylfurfural, a versatile platform chemical made from renewable resources. Chem Rev. 2013; 113(3):1499-597. DOI: 10.1021/cr300182k. View

17.

Lee S, Jung H, Kim N, Oh H, Min B, Hwang Y . Mixed Copper States in Anodized Cu Electrocatalyst for Stable and Selective Ethylene Production from CO Reduction. J Am Chem Soc. 2018; 140(28):8681-8689. DOI: 10.1021/jacs.8b02173. View

18.

Loh Y, Nagao K, Hoover A, Hesk D, Rivera N, Colletti S . Photoredox-catalyzed deuteration and tritiation of pharmaceutical compounds. Science. 2017; 358(6367):1182-1187. PMC: 5907472. DOI: 10.1126/science.aap9674. View

19.

Sheppard D, Henkelman G . Paths to which the nudged elastic band converges. J Comput Chem. 2011; 32(8):1769-71. DOI: 10.1002/jcc.21748. View

20.

Chen S, Wojcieszak R, Dumeignil F, Marceau E, Royer S . How Catalysts and Experimental Conditions Determine the Selective Hydroconversion of Furfural and 5-Hydroxymethylfurfural. Chem Rev. 2018; 118(22):11023-11117. DOI: 10.1021/acs.chemrev.8b00134. View