Enzyme-Catalyzed Glycerol Carbonate Esterification

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Solution Overview

Problem

Existing processes for producing esters of (meth)acrylic acid with glycerol carbonate suffer from low space-time yield and impurity issues, necessitating a method that enhances yield and purity.

Innovation Solution

A process involving the reaction of (meth)acrylic acid or its ester with glycerol carbonate in the presence of an enzyme catalyst, conducted without a solvent at a temperature of 10 to 150°C, utilizing immobilized lipases like Candida Antarctica Lipase B, to achieve high yield and selectivity.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Productivity

If conventional processes are used to produce esters of (meth)acrylic acid with glycerol carbonate, then the production can proceed with existing methods, but the space-time yield is low and the product purity is insufficient

Engineering Contradiction:
Improvespace-time yieldVSAvoidproduct purity
Core Design Contradiction:
ProductivityVSManufacturing precision

Solution Approach 1:

The patent introduces an enzyme (lipase or esterase) as a biological intermediary catalyst to mediate the esterification reaction between (meth)acrylic acid and glycerol carbonate. This enzyme catalyst enables the reaction to proceed with high selectivity and efficiency, simultaneously improving space-time yield and product purity without requiring additional purification steps

Inventive Principle:
Principle #24Intermediary (Mediator)

Solution Approach 2:

The patent optimizes reaction parameters including temperature (30-70°C), enzyme amount (1-10 wt% based on glycerol carbonate), and molar ratio of (meth)acrylic acid to glycerol carbonate (1:1 to 10:1). These parameter changes enable the reaction to achieve high conversion and selectivity, resolving the contradiction between productivity and manufacturing precision

Inventive Principle:
Principle #35Parameter changes

2Ease of manufacture

If solvents are used in the reaction process, then the reaction can proceed smoothly, but additional purification steps are required and process complexity increases

Engineering Contradiction:
Improveprocess simplicityVSAvoidproduct purity
Core Design Contradiction:
Ease of manufactureVSManufacturing precision

Solution Approach 1:

The patent completely removes the solvent from the reaction system, performing the esterification reaction in a solvent-free condition. This eliminates the need for additional purification steps to remove solvent residues, thereby simplifying the process while maintaining high product purity

Inventive Principle:
Principle #2Taking out (Extraction)

Solution Approach 2:

The reaction mixture itself serves as the reaction medium without requiring an external solvent. The reactants (meth)acrylic acid and glycerol carbonate undergo esterification directly, and the water byproduct is removed to drive the reaction forward, achieving both process simplicity and high purity

Inventive Principle:
Principle #25Self-service

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 method produces esters with high purity and yield, suitable for applications in contact lenses, adhesives, and coatings, eliminating the need for additional purification steps.

Implementation Method 1

reacting (meth)acrylic acid or an ester thereof with glycerol carbonate in the presence of at least one enzyme catalyzing the esterification reaction

Methodology Applied
Scientific EffectEsterification: Chemical Bonding

Implementation Method 2

in the presence of at least one enzyme catalyzing the esterification reaction

Methodology Applied
Scientific EffectCatalysis: Catalysis

Data Source

PatentEP3668848B1Process for the preparation (METH)acrylates of glycerol carbonates
Publication Date: 2021.06.30 BASF SE
  • EP3668848B1 patent drawing
  • EP3668848B1 patent drawing
  • EP3668848B1 patent drawing

AI summary

Process for producing esters of (meth)acrylic acid or a derivative thereof by reaction of (meth)acrylic acid or a derivative thereof with glycerol carbonate in the presence of at least one enzyme which catalyzes the esterification reaction, in the absence of a solvent and at a reaction temperature of 10°C to 150°C.