2-(Meth)Acryloyloxy Benzoic Ester Synthesis Without Solid By-Products
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Solution Overview
Problem
Existing methods for preparing 2-(meth)acryloyloxy benzoic acid esters require solvents and result in the formation of equimolar solid by-products that need intensive work-up, limiting scalability and yield.
Innovation Solution
A solvent-free process using a mixture of earth alkaline and alkaline salts as catalysts to react 2-hydroxybenzoates with (meth)acrylic acid anhydride, employing a stabilizer and conducting the reaction under controlled conditions to achieve high yield and purity.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Ease of manufacture
If conventional methods using solvents and equimolar reagents are employed, then the reaction can proceed, but solid by-products are formed requiring intensive work-up and filtration
Solution Approach 1:
The patent changes the stoichiometric parameters by using excess (meth)acrylic anhydride instead of equimolar amounts, and changes the physical state parameter by conducting the reaction in solvent-free conditions. This transforms the by-product from solid ammonium salt (requiring filtration) to liquid/excess reagent that can be easily removed, resolving the contradiction between ease of isolation and yield loss.
Solution Approach 2:
The patent extracts/eliminates the problematic solid by-product formation by changing the reaction parameters. Instead of forming equimolar solid salts that require intensive work-up, the method uses excess anhydride that doesn't form solid precipitates, thereby removing the filtration and work-up steps while improving yield.
2Productivity
If solvents are used in the reaction, then the reaction can proceed smoothly, but the process becomes unsuitable for large-scale production due to intensive work-up requirements
Solution Approach 1:
The patent eliminates solvent use by changing the reaction medium parameter to solvent-free conditions. This simplification removes the need for solvent removal, drying, and extensive work-up procedures, making the process scalable while reducing operational complexity.
Solution Approach 2:
The patent removes the solvent component entirely from the system, extracting the problematic element that requires complex work-up. The solvent-free approach eliminates filtration, washing, and drying steps associated with solvent removal, thereby improving productivity and reducing device complexity.
3Productivity
If (meth)acrylic acid anhydride is used in equimolar amounts, then the reaction is efficient, but equimolar solid by-products are formed
Solution Approach 1:
The patent changes the stoichiometric parameter from equimolar to excess (meth)acrylic anhydride. This parameter change prevents the formation of equimolar solid by-products while maintaining high reaction efficiency, as the excess anhydride does not form solid precipitates requiring filtration.
Solution Approach 2:
The patent converts the potential harm of excess reagent into a benefit: the excess (meth)acrylic anhydride, instead of forming problematic solid by-products, serves to drive the reaction to completion and can be easily removed due to its physical properties, thereby eliminating the harmful solid by-product issue.
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
The process achieves high yield and purity of 2-(meth)acryloyloxy benzoic acid esters without solid by-products, suitable for large-scale production and applications in photopolymerization processes and medical devices.
Implementation Method 1
reacting 2-hydroxybenzoates with (meth)acrylic acid anhydride in the presence of a mixture of an earth alkaline salt and an alkaline salt as catalyst
Data Source
AI summary
The present invention is directed to a solvent-free process for the preparation of 2- (meth)acryloyloxy benzoic acid esters wherein 2-hydroxybenzoates are reacted with (meth)acrylic acid anhydride in the presence of a mixture of an earth alkaline salt and an alkaline salt as catalyst.