Copper Oxide Catalysts for Vicinal Diol Oxidative Cleavage

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Solution Overview

Problem

Current processes for preparing carboxylic acids through oxidative cleavage of vicinal diols or epoxides use potentially toxic catalysts that are difficult to separate and recycle, leading to contamination and reduced economic viability.

Innovation Solution

The process employs copper oxide-based catalysts, which are less toxic and easier to separate, maintaining high selectivity and allowing for catalyst recovery and reuse, using supported copper oxide catalysts in the presence of molecular oxygen for oxidative cleavage of vicinal diols or epoxides derived from unsaturated fatty acids.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Productivity

If cobalt compounds are used as catalysts for oxidative cleavage, then high selectivity and yield are achieved, but the catalysts are toxic and difficult to separate from the reaction medium

Engineering Contradiction:
Improveyield of carboxylic acidsVSAvoidtoxicity of catalyst
Core Design Contradiction:
ProductivityVSObject-affected harmful factors

Solution Approach 1:

The patent changes the chemical composition parameter of the catalyst from cobalt compounds to copper oxide-based catalysts. This parameter change maintains catalytic activity and selectivity while eliminating the toxicity issue, as copper oxide is significantly less toxic than cobalt compounds and can be easily separated from the reaction medium.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent employs heterogeneous copper oxide catalysts that can be easily separated from the reaction medium through filtration or centrifugation. These catalysts can be reused multiple times without significant loss of activity, replacing the need for continuous addition of toxic cobalt catalysts.

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

2Productivity

If homogeneous catalysts are used for oxidative cleavage, then high catalytic activity is achieved, but the catalysts contaminate the product and are difficult to recover

Engineering Contradiction:
Improvecatalytic activityVSAvoidcatalyst contamination of product
Core Design Contradiction:
ProductivityVSLoss of substance

Solution Approach 1:

The patent extracts the catalyst from the reaction medium by using heterogeneous copper oxide catalysts that can be easily separated through filtration or centrifugation. This extraction process eliminates catalyst contamination of the product while maintaining high catalytic activity during the oxidative cleavage reaction.

Inventive Principle:
Principle #2Taking out (Extraction)

Solution Approach 2:

The patent segments the catalyst system into heterogeneous copper oxide particles that can be physically separated from the homogeneous reaction medium. This segmentation allows for complete separation of catalyst from product, eliminating contamination while preserving catalytic functionality.

Inventive Principle:
Principle #1Segmentation

3Manufacturing precision

If traditional catalysts are used for oxidative cleavage, then high selectivity is achieved, but the process economics are reduced due to contamination and recovery difficulties

Engineering Contradiction:
Improveselectivity for carboxylic acidsVSAvoideconomic feasibility of process
Core Design Contradiction:
Manufacturing precisionVSEase of manufacture

Solution Approach 1:

The patent changes the catalyst parameter from toxic cobalt compounds to copper oxide-based catalysts. This parameter change maintains the high selectivity required for producing specific carboxylic acids while dramatically improving process economics through easier separation, reduced contamination, and catalyst reusability.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent converts the previously harmful effect of catalyst contamination into a benefit by using heterogeneous copper oxide catalysts that can be easily separated. The ease of separation becomes an economic advantage, enabling catalyst recovery and reuse while maintaining product purity and selectivity.

Inventive Principle:
Principle #22Blessing in disguise (Convert harm into benefit)

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 selectivity and activity comparable to traditional catalysts while reducing contamination and enabling catalyst recycling, enhancing the economic feasibility of the process.

Implementation Method 1

The process employs copper oxide-based catalysts, which are less toxic and easier to separate, maintaining high selectivity and allowing for catalyst recovery and reuse, using supported copper oxide catalysts in the presence of molecular oxygen for oxidative cleavage of vicinal diols or epoxides derived from unsaturated fatty acids.

Methodology Applied
Scientific EffectCatalysis: Catalysis

Implementation Method 2

The project which led to the invention was financed by the Bio Based Industries Joint Undertaking Public-Private Partnership as part of the European Union Horizon 2020 research and innovation programme under Grant Agreement No. 669029. This invention relates to a process for the preparation of carboxylic acids by the oxidative cleavage of vicinal diols and/or epoxides in the presence of catalysts containing copper oxides.

Methodology Applied
Scientific EffectOxidation: Oxidation

Data Source

PatentEP3713908B1Production of carboxylic acids from vicinal diols
Publication Date: 2023.06.28 NOVAMONT SPA

AI summary

The present invention relates to a process of preparation of carboxylic acids by oxidative cleavage of at least one vicinal diol or an epoxide in the presence of an oxidant comprising molecular oxygen and a heterogeneous catalyst comprising a copper oxide.