Barium Phosphate Catalyst for Selective Ester Condensation

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Solution Overview

Problem

Current methods for producing ethylenically unsaturated carboxylic acids or esters, such as methacrylic acid and methyl methacrylate, face challenges including water formation, hydrolysis of esters, and high levels of dimethyl ether production, which complicates product separation and reduces selectivity.

Innovation Solution

The use of barium phosphate catalysts with plate or leaf-like crystal habits, which provide high selectivity and low water production, effectively catalyzing the condensation of methylene sources with carboxylic acids or esters, thereby minimizing unwanted side reactions and improving product separation.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If conventional catalysts are used for the condensation of carboxylic acid or ester with formaldehyde or dimethoxymethane, then the reaction can proceed, but water is formed which hydrolyzes the ester feedstock or product, reducing selectivity and complicating separation

Engineering Contradiction:
ImproveselectivityVSAvoidwater formation
Core Design Contradiction:
ReliabilityVSObject-generated harmful factors

Solution Approach 1:

The invention changes the chemical parameter of the catalyst by using barium phosphate with specific plate or leaf-like crystal habits, which fundamentally alters the reaction pathway to minimize water formation during the condensation reaction, thereby preventing ester hydrolysis and improving selectivity

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention employs a composite catalyst system comprising barium phosphate combined with other metal phosphates or metal oxides, where the barium phosphate component specifically addresses water formation while the composite structure enhances overall catalytic activity and selectivity for the desired condensation reaction

Inventive Principle:
Principle #40Composite materials

2Reliability

If dimethoxymethane is used as a formaldehyde source to avoid water, then anhydrous conditions are achieved, but dimethoxymethane decomposes to dimethyl ether and formaldehyde, and methanol dehydrates to dimethyl ether and water

Engineering Contradiction:
Improveanhydrous conditionsVSAvoiddimethyl ether formation
Core Design Contradiction:
ReliabilityVSObject-generated harmful factors

Solution Approach 1:

The invention changes the catalytic parameters by using barium phosphate with plate or leaf-like crystal habits, which selectively promotes the condensation reaction while suppressing the decomposition of dimethoxymethane to dimethyl ether, thereby maintaining anhydrous conditions and improving product selectivity

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The barium phosphate catalyst acts as an intermediary that facilitates the desired condensation reaction between dimethoxymethane and carboxylic acid or ester while preventing the side reaction that produces dimethyl ether, effectively mediating between the reactants to achieve selective product formation

Inventive Principle:
Principle #24Intermediary (Mediator)

3Productivity

If conventional catalysts are used, then the condensation reaction proceeds, but product separation is complicated due to water and dimethyl ether presence

Engineering Contradiction:
Improveproduct separation efficiencyVSAvoidseparation process complexity
Core Design Contradiction:
ProductivityVSDevice complexity

Solution Approach 1:

The invention changes the reaction parameters by using barium phosphate catalyst that produces minimal water and dimethyl ether, fundamentally simplifying the product separation process and improving overall productivity by eliminating complex separation requirements

Inventive Principle:
Principle #35Parameter changes

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 selectivity rates of up to 95 mole% for ethylenically unsaturated carboxylic acid or ester production while significantly reducing dimethyl ether formation, resulting in a more efficient and simplified product separation process.

Implementation Method 1

The use of barium phosphate catalysts with plate or leaf-like crystal habits, which provide high selectivity and low water production, effectively catalyzing the condensation of methylene sources with carboxylic acids or esters

Methodology Applied
Scientific EffectCatalysis: Catalysis

Implementation Method 2

dimethoxymethane decomposes under catalytic conditions to dimethylether and formaldehyde

Methodology Applied
Scientific EffectDecomposition: Decomposition (biological)

Implementation Method 3

methanol dehydrates to dimethyl ether and water

Methodology Applied
Scientific EffectDehydration:

Implementation Method 4

Any water formed in these reactions can hydrolyse the ester feedstock or product to its corresponding acid

Methodology Applied
Scientific EffectHydrolysis: Hydrolysis

Data Source

PatentEP2802552B1A process for the production of ethylenically unsaturated carboxylic acids or esters and a catalyst therefor
Publication Date: 2018.03.28 LUCITE INT UK LTD
  • EP2802552B1 patent drawingFigure 1
  • EP2802552B1 patent drawingFigure 2
  • EP2802552B1 patent drawingFigure 3

AI summary

A method of producing an ethylenically unsaturated, typically,an alpha, ß ethylenically unsaturated carboxylic acid or ester is described. The method comprises the steps of contacting formaldehyde, or a source of formaldehyde, with a carboxylic acid or ester in the presence of a catalyst and optionally in the presence of an alcohol. The catalyst comprises barium phosphate leaf or plate shaped/like crystals, or a source thereof.A catalyst system is also described. The catalyst system comprises a crystalline barium phosphate catalyst and optionally a catalyst support.