Copper Anode Oxidation of HMF to FDCA

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Solution Overview

Problem

Current methods for the electrochemical oxidation of 5-hydroxymethylfurfural (HMF) to 2,5-furandicarboxylic acid (FDCA) face challenges in achieving high yields and stability due to the use of noble metals and high pH conditions, which lead to base-induced polymerization and insoluble humins formation.

Innovation Solution

The use of copper-based anodes in electrochemical cells with an oxygen-donating electrolyte solution allows for the oxidation of HMF to FDCA with a yield of at least 75% and a Faradaic efficiency of at least 75%, eliminating the need for precious metal catalysts and operating at ambient conditions.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Productivity

If high pH conditions (pH 14) are used to increase HMF oxidation kinetics and achieve high FDCA yields, then the oxidation rate and yield improve, but HMF stability decreases due to base-induced polymerization forming insoluble humins

Engineering Contradiction:
ImproveFDCA production rate and yieldVSAvoidHMF stability
Core Design Contradiction:
ProductivityVSStability of the object's composition

Solution Approach 1:

The patent changes the pH parameter from highly alkaline (pH 14) to neutral or slightly basic conditions (pH 7-9), fundamentally altering the reaction environment to prevent HMF polymerization while maintaining effective oxidation kinetics through the copper-based anode catalyst

Inventive Principle:
Principle #35Parameter changes

2Productivity

If noble metal catalysts (Pt, Pd, Au) are used to achieve high FDCA yields, then the catalytic activity and selectivity improve, but the cost and complexity of the system increase

Engineering Contradiction:
ImproveFDCA yieldVSAvoidcatalyst complexity
Core Design Contradiction:
ProductivityVSDevice complexity

Solution Approach 1:

The patent replaces expensive noble metal catalysts with a copper-based anode that can be easily replaced or regenerated. The copper anode provides the necessary catalytic activity at much lower cost and simplifies the overall system by eliminating the need for precious metal materials

Inventive Principle:
Principle #27Cheap short-living objects (Disposable)

Solution Approach 2:

The copper-based anode replicates the catalytic function of noble metals through a different material system. The copper surface undergoes oxidation to form CuO/Cu2O species that provide similar catalytic activity for HMF oxidation, achieving comparable FDCA yields without using precious metals

Inventive Principle:
Principle #26Copying

3Productivity

If noble metal catalysts are used to achieve high FDCA yields, then the catalytic performance improves, but the cost of the system increases

Engineering Contradiction:
ImproveFDCA yieldVSAvoidcost
Core Design Contradiction:
ProductivityVSQuantity of substance

Solution Approach 1:

The patent substitutes expensive noble metals with inexpensive copper material. The copper anode can be readily obtained at low cost and, if needed, replaced or regenerated without significant expense, making the process economically viable for large-scale FDCA production

Inventive Principle:
Principle #27Cheap short-living objects (Disposable)

Applied Scientific Principles

This section explains which scientific principles are used to turn an abstract innovation direction into a practical engineering solution.

Function Achieved in This Case

This approach achieves high conversion and yield of HMF to FDCA while maintaining stability and reducing environmental impact by using copper-based anodes, which are inexpensive and non-catalytic for water oxidation, thus overcoming the limitations of previous methods.

Implementation Method 1

the electrochemical oxidation of 5-hydroxymethylfurfural (HMF) to 2,5-furandicarboxylic acid (FDCA)

Methodology Applied
Scientific EffectElectrochemical oxidation: Oxidation

Implementation Method 2

5-hydroxymethylfurfural can be oxidized by applying an anode potential to the anode that induces the electrochemical oxidation of the 5-hydroxymethylfurfural

Methodology Applied
Scientific EffectElectrochemical reaction: Redox Reactions

Data Source

PatentUS11708639B2Electrochemical oxidation of 5-hydroxymethylfurfural using copper-based anodes
Publication Date: 2023.07.25 WISCONSIN ALUMNI RES FOUND
  • US11708639B2 patent drawing
  • US11708639B2 patent drawing
  • US11708639B2 patent drawing

AI summary

Electrochemical cells for the oxidation of 5-hydroxymethylfurfural are provided. Also provided are methods of using the cells to carry out the oxidation reactions. The electrochemical cells and methods use catalytic copper-based anodes to carry out the electrochemical oxidation reactions.