Electrochemical Oxidation of Aromatic Aldehydes Using Non-Noble Electrodes

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Solution Overview

Problem

Current methods for converting aromatic aldehydes to aromatic dicarboxylic acids, such as furandicarboxylic acid and terephthalic acid, often require noble metal electrodes and additional mediators, leading to incomplete conversions and costly purification processes.

Innovation Solution

A process involving the electrochemical oxidation of aromatic aldehyde compounds using a feedstock with a non-noble metal or carbon electrode in an electrolytic cell, where the aromatic aldehyde is substituted with a carboxyl group, allowing for complete conversion to aromatic dicarboxylic acid without the need for noble metals or mediators.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If noble metal electrodes and mediators are used for electrochemical oxidation of aromatic aldehydes, then the oxidation reaction can proceed, but the conversion is incomplete and costly purification is required

Engineering Contradiction:
Improveconversion completenessVSAvoidpurification process complexity
Core Design Contradiction:
ReliabilityVSDevice complexity

Solution Approach 1:

The patent changes the electrode material parameter from noble metals to non-noble metals (nickel, iron, copper) or carbon, and adjusts the electrolyte composition (pH, additives) to achieve complete conversion without requiring complex purification steps. This parameter change resolves the contradiction by maintaining reaction effectiveness while eliminating the need for costly purification.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent replaces expensive noble metal electrodes with inexpensive non-noble metal electrodes or carbon electrodes that can be easily replaced. These cheaper electrodes achieve the same or better conversion results, eliminating the need for complex purification processes and reducing overall process cost.

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

2Reliability

If noble metal electrodes are used for electrochemical oxidation, then the reaction can proceed, but the process cost increases significantly

Engineering Contradiction:
Improvereaction effectivenessVSAvoidprocess cost
Core Design Contradiction:
ReliabilityVSEase of manufacture

Solution Approach 1:

The patent substitutes expensive noble metal electrodes with inexpensive non-noble metal electrodes (nickel, iron, copper) or carbon electrodes. These cheaper electrodes maintain reaction effectiveness while dramatically reducing process cost, making the electrochemical oxidation economically viable.

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

Solution Approach 2:

The patent extracts the essential function of electrode catalysis from noble metals and transfers it to non-noble metals or carbon materials. This extraction allows the process to maintain reaction effectiveness while eliminating the cost burden of noble metals.

Inventive Principle:
Principle #2Taking out (Extraction)

3Productivity

If conventional oxidation methods are used to convert aromatic aldehydes to dicarboxylic acids, then conversion can occur, but by-products like carbon monoxide and carbon dioxide are formed

Engineering Contradiction:
ImproveyieldVSAvoidby-product formation
Core Design Contradiction:
ProductivityVSObject-generated harmful factors

Solution Approach 1:

The patent replaces conventional chemical oxidation methods with electrochemical oxidation. This substitution uses electrical energy to drive the oxidation reaction selectively, avoiding the formation of harmful by-products like carbon monoxide and carbon dioxide that are typical of conventional oxidation methods, while maintaining high yield.

Inventive Principle:
Principle #28Mechanics substitution (Replace mechanical system)

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 process achieves virtually complete conversion of aromatic aldehydes to dicarboxylic acids, reducing the need for costly purification steps and increasing the overall yield by avoiding the formation of by-products like carbon monoxide and carbon dioxide, while also removing colorants, thus enhancing the economic feasibility of the process.

Implementation Method 1

the electrochemical oxidation of aromatic aldehydes using a feedstock with a non-noble metal or carbon electrode in an electrolytic cell

Methodology Applied
Scientific EffectElectrochemical oxidation: Oxidation

Implementation Method 2

electrochemical oxidation of aromatic aldehyde compounds using a feedstock with a non-noble metal or carbon electrode in an electrolytic cell

Methodology Applied
Scientific EffectElectrolysis: Electrolysis

Implementation Method 3

electrochemical oxidation of aromatic aldehydes using a feedstock with a non-noble metal or carbon electrode in an electrolytic cell

Methodology Applied
Scientific EffectElectrochemical reaction:

Data Source

PatentEP3297995B1Process for the preparation of an aromatic dicarboxylic acid
Publication Date: 2019.07.10 AVANTIUM KNOWLEDGE CENT BV

AI summary

An aromatic dicarboxylic acid of chemical formula HOOC-Ar1-COOH is prepared in a process wherein a feedstock comprising at least an aromatic aldehyde compound of chemical formula (1): OHC-Ar1-COOH, wherein Ar1 represents an arylene or heteroarylene moiety, and an aqueous electrolyte are provided; the feedstock and the aqueous electrolyte are introduced into an electrolytic cell comprising electrodes, wherein at least one of the electrodes comprises a non-noble metal and/or an oxide and/or a hydroxide thereof and/or carbon; and the aromatic aldehyde compound of formula (1) is oxidized electrochemically to yield the aromatic dicarboxylic acid.