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A comparative study of thermal- and electrocatalytic conversion of furfural: methylfuran as a primary and major product

Journal Article · · Journal of Applied Electrochemistry
 [1];  [2];  [3];  [3]
  1. Univ. of Oklahoma, Norman, OK (United States). Center for Interfacial Reaction Engineering and School of Chemical, Biological and Materials Engineering; University of Oklahoma
  2. Univ. of Oklahoma, Norman, OK (United States). Center for Interfacial Reaction Engineering and School of Chemical, Biological and Materials Engineering; Loyola College, Tamil Nadu, Chennai (India)
  3. Univ. of Oklahoma, Norman, OK (United States). Center for Interfacial Reaction Engineering and School of Chemical, Biological and Materials Engineering
Controlling reaction selectivity represents a fundamental challenge in heterogeneous catalysis. Here, we compare the selectivity in aqueous-phase thermal catalytic and electrocatalytic conversion of furfural and report the fundamental difference in elementary steps in the two reaction systems. Specifically, we observed that furfural alcohol and 2-methylfuran, which is the hydrogenation and hydrogenolysis product of furfural, respectively, are both primary products in electrocatalysis over a Cu electrode, with 2-methylfuran dominating the product distribution under electrode potentials between -0.55 and -0.75 V versus RHE. By contrast, in an aqueous-phase thermal reaction using a SiO2-supported Cu catalyst, furfural alcohol and its derivatives from the ring-rearrangement reaction are the major products, without production of 2-methylfuran, at the reaction temperature between 140 and 200 °C. Here, we propose that the distinct selectivity trends for oxygenate conversion via thermal and electrocatalytic reduction result from the distinct sequence of proton attack to the aldehyde group and may be generally true for reduction reactions of other biomass-derived oxygenates.
Research Organization:
Univ. of Oklahoma, Norman, OK (United States)
Sponsoring Organization:
USDOE Office of Science (SC), Basic Energy Sciences (BES). Chemical Sciences, Geosciences & Biosciences Division
Grant/Contract Number:
SC0018284
OSTI ID:
1775274
Journal Information:
Journal of Applied Electrochemistry, Journal Name: Journal of Applied Electrochemistry Journal Issue: 1 Vol. 51; ISSN 0021-891X
Publisher:
SpringerCopyright Statement
Country of Publication:
United States
Language:
English

References (44)

Selective Hydrogenation of Furfural in a Proton Exchange Membrane Reactor Using Hybrid Pd/Pd Black on Alumina journal October 2019
Electrocatalytic Upgrading of Biomass‐Derived Intermediate Compounds to Value‐Added Products journal June 2018
Controlling Competitive Side Reactions in the Electrochemical Upgrading of Furfural to Biofuel journal June 2018
Hydrodeoxygenation of Furfural Over Supported Metal Catalysts: A Comparative Study of Cu, Pd and Ni journal March 2011
Aqueous phase electrocatalysis and thermal catalysis for the hydrogenation of phenol at mild conditions journal March 2016
Stabilization of furanics to cyclic ketone building blocks in the vapor phase journal October 2019
Selective liquid-phase hydrogenation of furfural to furfuryl alcohol over Cu-based catalysts journal September 2013
Aqueous electrocatalytic hydrogenation of furfural using a sacrificial anode journal March 2012
Electrocatalytic hydrogenation of furfural to furfuryl alcohol using platinum supported on activated carbon fibers journal July 2014
Kinetics and mechanism of hydrogenation of furfural on Cu/SiO2 catalysts journal January 2011
Integrated catalytic and electrocatalytic conversion of substituted phenols and diaryl ethers journal December 2016
Hydrogenation of benzaldehyde via electrocatalysis and thermal catalysis on carbon-supported metals journal March 2018
Mechanism and kinetics of the electrocatalytic hydrogenation of furfural to furfuryl alcohol journal November 2017
How Catalysts and Experimental Conditions Determine the Selective Hydroconversion of Furfural and 5-Hydroxymethylfurfural journal October 2018
Mechanistic Insights Evaluating Ag, Pb, and Ni as Electrocatalysts for Furfural Reduction from First-Principles Methods journal November 2017
Efficient Electrocatalytic Reduction of Furfural to Furfuryl Alcohol in a Microchannel Flow Reactor journal February 2019
Exploring Furfural Catalytic Conversion on Cu(111) from Computation journal June 2015
Electrocatalytic Conversion of Furanic Compounds journal September 2016
Electrocatalytic Hydrogenation of Phenol over Platinum and Rhodium: Unexpected Temperature Effects Resolved journal October 2016
A Combined Experimental and Theoretical Study on the Activity and Selectivity of the Electrocatalytic Hydrogenation of Aldehydes journal June 2018
Elucidating Acidic Electro-Oxidation Pathways of Furfural on Platinum journal September 2019
Water-Mediated Heterogeneously Catalyzed Reactions journal December 2019
Electrocatalytic Hydrogenation and Hydrogenolysis of Furfural and the Impact of Homogeneous Side Reactions of Furanic Compounds in Acidic Electrolytes journal October 2016
Catalytic Reduction of Biomass-Derived Furanic Compounds with Hydrogen journal October 2013
Mechanisms of Furfural Reduction on Metal Electrodes: Distinguishing Pathways for Selective Hydrogenation of Bioderived Oxygenates journal September 2017
Solvent Tunes the Selectivity of Hydrogenation Reaction over α-MoC Catalyst journal October 2018
Zeolite-Encapsulated Pt Nanoparticles for Tandem Catalysis journal September 2018
Electrochemical Reduction of the Carbonyl Functional Group: The Importance of Adsorption Geometry, Molecular Structure, and Electrode Surface Structure journal July 2019
Directing reaction pathways by catalyst active-site selection using self-assembled monolayers journal September 2013
Distributed processes for biomass conversion could aid UN Sustainable Development Goals journal October 2018
Solvent-mediated charge separation drives alternative hydrogenation path of furanics in liquid water journal April 2019
Density functional theory calculations for the hydrogen evolution reaction in an electrochemical double layer on the Pt(111) electrode journal January 2007
Electrocatalytic valorisation of biomass derived chemicals journal January 2018
An electrocatalytic route for transformation of biomass-derived furfural into 5-hydroxy-2(5 H )-furanone journal January 2019
New insights into the electrochemical reduction of carbon dioxide on metallic copper surfaces journal January 2012
Electrochemistry for biofuel generation: production of furans by electrocatalytic hydrogenation of furfurals journal January 2013
The electrocatalytic hydrogenation of furanic compounds in a continuous electrocatalytic membrane reactor journal January 2013
Conversion of furfural into cyclopentanone over Ni–Cu bimetallic catalysts journal January 2013
Toward biomass-derived renewable plastics: Production of 2,5-furandicarboxylic acid from fructose journal January 2018
Renewable lubricants with tailored molecular architecture journal February 2019
Catalytic Conversion of Biomass to Monofunctional Hydrocarbons and Targeted Liquid-Fuel Classes journal October 2008
Composites from renewable and sustainable resources: Challenges and innovations journal November 2018
Electrochemical Conversion of Biomass-Based Oxygenated Compounds journal June 2019
Recent Advances in Catalytic Hydrogenation of Furfural journal September 2019

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