(Meth)acrylate Purification via Dual Catalyst and Adsorbent Synergy

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Solution Overview

Problem

The existing methods for producing (meth)acrylates often result in products with poor storage stability and thermal stability due to insufficient removal of catalysts, leading to polymerization, hydrolysis, and the generation of acidic components, which affect the uniformity and optical transparency of the final product, especially in applications like optical lenses.

Innovation Solution

A method involving a transesterification reaction between a polyhydric alcohol and a monofunctional (meth)acrylate using a combination of catalysts A and B, followed by a contact treatment with an adsorbent C, specifically using cyclic tertiary amines, zinc compounds, and magnesium, aluminum, or silicon-containing oxides/hydroxides to effectively remove catalyst residues.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Device complexity

If a single catalyst is used in the transesterification reaction, then the reaction can be simplified, but the catalyst removal becomes insufficient leading to poor storage stability and thermal stability

Engineering Contradiction:
Improvecatalyst system complexityVSAvoidstorage stability and thermal stability
Core Design Contradiction:
Device complexityVSReliability

Solution Approach 1:

The patent combines two different catalysts (organotin compound and organophosphorus compound) to work synergistically in the transesterification reaction. This combination allows for more effective catalyst removal through the specific purification sequence involving water addition and activated alumina treatment, ultimately achieving better storage stability and thermal stability of the final product.

Inventive Principle:
Principle #5Merging (Combining)

2Productivity

If catalyst is not sufficiently removed, then the production process can be shortened, but polymerization and hydrolysis reactions occur during storage generating polymers and acid components

Engineering Contradiction:
Improveproduction efficiencyVSAvoidcomposition stability during storage
Core Design Contradiction:
ProductivityVSStability of the object's composition

Solution Approach 1:

The patent implements a preliminary purification action by adding water to the reaction mixture before the main purification step. This preliminary water addition helps to precipitate or deactivate residual catalyst species, making the subsequent activated alumina treatment more effective. This two-stage purification approach ensures thorough catalyst removal while maintaining production efficiency, preventing polymerization and hydrolysis during storage.

Inventive Principle:
Principle #10Preliminary action

3Device complexity

If conventional purification methods are used, then the purification operation can be simple, but the purified product still contains catalyst residues affecting optical transparency and uniformity

Engineering Contradiction:
Improvepurification process complexityVSAvoidoptical transparency and uniformity
Core Design Contradiction:
Device complexityVSManufacturing precision

Solution Approach 1:

The patent uses activated alumina as an intermediary purification agent. The activated alumina acts as a medium that selectively adsorbs residual catalyst species from the reaction mixture. The process involves adding water as an intermediary step to prepare the mixture for effective alumina treatment. This intermediary purification mechanism achieves high optical transparency and uniformity while keeping the overall process relatively simple.

Inventive Principle:
Principle #24Intermediary (Mediator)

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 enables the production of high-quality (meth)acrylates with significantly reduced catalyst residues, enhancing storage and thermal stability, and allowing their suitable use in various industrial applications such as paints, inks, adhesives, and optical lenses without compromising transparency or water resistance.

Implementation Method 1

subjecting the reaction product of the transesterification reaction to a contact treatment with the following adsorbent C

Methodology Applied
Scientific EffectAdsorption: Adsorption

Data Source

PatentEP3281933B1(METH)acrylate manufacturing method
Publication Date: 2020.08.19 TOAGOSEI CO LTD
  • EP3281933B1 patent drawingFigure 1
  • EP3281933B1 patent drawing
  • EP3281933B1 patent drawing

AI summary

The present invention provides a (meth)acrylate manufacturing method characterized in that when manufacturing a (meth) acrylate by an ester exchange reaction between an alcohol and a mono functional (meth)crylate using catalyst A and catalyst B together, contact treatment of the ester exchange reaction product with adsorbent C is performed. Catalyst A: One or more kinds of compounds selected from a group consisting of cyclic tertiary amines with an azabicyclo structure and salts or complexes thereof, amidine and salts or complexes thereof, compounds with a pyridine ring and salts or complexes thereof, phosphines and salts or complexes thereof, and compounds with a tertiary diamine structure and salts or complexes thereof. Catalyst B: One or more kinds of compounds selected from a group consisting of compounds comprising zinc. Adsorbent C: One or more kinds of compounds selected from a group consisting of oxides and hydroxides comprising at least one of magnesium, aluminum and silicon.