Campus Units
Chemical and Biological Engineering, Ames Laboratory, NSF Engineering Research Center for Biorenewable Chemicals
Document Type
Article
Research Focus Area
Catalysis and Reaction Engineering
Publication Version
Published Version
Publication Date
2019
Journal or Book Title
Green Chemistry
Volume
21
Issue
22
First Page
6210
Last Page
6219
DOI
10.1039/C9GC02264C
Abstract
Electrochemical conversion of biomass-derived compounds is a promising route for sustainable chemical production. Herein, we report unprecedentedly high efficiency for conversion of 5-(hydroxymethyl)furfural (HMF) to biobased monomers by pairing HMF reduction and oxidation half-reactions in one electrochemical cell. Electrocatalytic hydrogenation of HMF to 2,5-bis(hydroxymethyl)furan (BHMF) was achieved under mild conditions using carbon-supported Ag nanoparticles (Ag/C) as the cathode catalyst. The competition between Ag-catalyzed HMF hydrogenation to BHMF and undesired HMF hydrodimerization and hydrogen evolution reactions was sensitive to cathode potential. Also, the carbon support material in Ag/C was active for HMF reduction at strongly cathodic potentials, leading to additional hydrodimerization and low BHMF selectivity. Accordingly, precise control of the cathode potential was implemented to achieve high BHMF selectivity and efficiency. In contrast, the selectivity of HMF oxidation facilitated by a homogeneous electrocatalyst, 4-acetamido-TEMPO (ACT, TEMPO = 2,2,6,6-tetramethylpiperidine-1-oxyl), together with an inexpensive carbon felt electrode, was insensitive to anode potential. Thus, it was feasible to conduct HMF hydrogenation to BHMF and oxidation to 2,5-furandicarboxylic acid (FDCA) in a single divided cell operated under cathode potential control. Electrocatalytic HMF conversion in the paired cell achieved high yields of BHMF and FDCA (85% and 98%, respectively) and a combined electron efficiency of 187%, corresponding to a nearly two-fold enhancement compared to the unpaired cells.
Creative Commons License
This work is licensed under a Creative Commons Attribution-Noncommercial 3.0 License
Copyright Owner
The Royal Society of Chemistry
Copyright Date
2019
Language
en
File Format
application/pdf
Recommended Citation
Chadderdon, Xiaotong H.; Chadderdon, David J.; Pfennig, Toni; Shanks, Brent H.; and Li, Wenzhen, "Paired electrocatalytic hydrogenation and oxidation of 5-(hydroxymethyl)furfural for efficient production of biomass-derived monomers" (2019). Chemical and Biological Engineering Publications. 412.
https://lib.dr.iastate.edu/cbe_pubs/412
Comments
This article is published as Chadderdon, Xiaotong H., David J. Chadderdon, Toni Pfennig, Brent H. Shanks, and Wenzhen Li. "Paired electrocatalytic hydrogenation and oxidation of 5-(hydroxymethyl) furfural for efficient production of biomass-derived monomers." Green Chemistry 21, no. 22 (2019): 6210-6219. DOI: 10.1039/C9GC02264C. Posted with permission.