(Meth)acrylic Acid Ester Synthesis via Basic Catalysis
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Solution Overview
Problem
Current methods for manufacturing (meth) acrylic acid esters and aromatic carboxylic acid esters face inefficiencies due to byproduct formation, equilibrium challenges, high costs, and excess reagent requirements, leading to suboptimal yields and increased wastewater treatment loads.
Innovation Solution
A method involving the reaction of (meth) acrylic anhydride and a carbonate compound in the presence of a catalyst, such as nitrogenous base-containing organic compounds, Group I metal compounds, or Group II metal compounds, to produce (meth) acrylic acid esters and aromatic carboxylic acid esters with high yields and reduced byproduct formation.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Ease of manufacture
If dehydration reactions are conducted on (meth) acrylic acid and alcohol in the presence of an acidic catalyst, then (meth) acrylic acid esters can be synthesized, but quite a few byproducts are observed and the resulting (meth) acrylic acid ester is decomposed by the generated water
Solution Approach 1:
The patent changes the reaction parameters by switching from acidic catalyst to basic catalyst (alkali metal hydroxide, alkaline earth metal hydroxide, or organic amine), and from dehydration reaction to transesterification reaction. This fundamental parameter change resolves the contradiction by eliminating water generation that causes decomposition, while maintaining efficient ester synthesis through the basic catalytic system.
Solution Approach 2:
The patent uses readily available basic catalysts such as sodium hydroxide, potassium hydroxide, calcium hydroxide, or organic amines like triethylamine. These catalysts are inexpensive, easily handled, and can be used in stoichiometric or near-stoichiometric amounts, making the process economically viable while avoiding the complications of acidic catalyst systems.
2Ease of manufacture
If transesterification reactions are conducted on alcohol and a lower alkyl ester of (meth) acrylic acid, then (meth) acrylic acid esters can be synthesized, but an excess amount of the lower alkyl ester of (meth) acrylic acid or alcohol as raw material is used
Solution Approach 1:
The patent changes the reaction type from transesterification to a direct reaction between (meth) acrylic acid and alcohol catalyzed by basic catalysts. This parameter change eliminates the equilibrium limitation of transesterification, allowing complete conversion with stoichiometric amounts of reactants, thereby improving both material efficiency and productivity.
3Manufacturing precision
If (meth) acrylic acid chloride and alcohol are reacted in the presence of an amine, then (meth) acrylic acid esters can be synthesized, but (meth) acrylic acid chloride used as raw material is expensive and a step for removing resulting amine hydrochloride causes a greater load on wastewater treatment
Solution Approach 1:
The patent replaces expensive (meth) acrylic acid chloride with inexpensive and readily available (meth) acrylic acid as the starting material. The basic catalyst system produces water-soluble salts as byproducts that can be easily removed, eliminating the need for complex amine hydrochloride removal steps and reducing wastewater treatment load.
Solution Approach 2:
The patent converts the potentially harmful acidic byproduct issue into a benefit by using basic catalysts that produce water-soluble salts. These salts can be easily separated and disposed of, turning what would be a purification challenge into a simple filtration or decantation step, thereby reducing environmental impact and treatment costs.
4Ease of manufacture
If dehydration reactions are conducted on carboxylic acid and phenol in the presence of an acidic catalyst, then aromatic carboxylic acid esters can be synthesized, but the aromatic carboxylic acid ester is decomposed by the water generated in the reaction
Solution Approach 1:
The patent changes the reaction parameters by using basic catalysts (alkali metal hydroxides, alkaline earth metal hydroxides, or organic amines) instead of acidic catalysts for the reaction between aromatic carboxylic acids and phenols. This fundamental change eliminates water generation that causes decomposition, allowing efficient synthesis of aromatic carboxylic acid esters through a water-free basic catalytic system.
5Ease of manufacture
If esters of aromatic carboxylic acid and diphenyl carbonate are reacted, then aromatic carboxylic acid esters can be synthesized, but an excess amount of aromatic carboxylic acid ester relative to the amount of diphenyl carbonate is necessary
Solution Approach 1:
The patent changes the reaction type from reaction with diphenyl carbonate to direct reaction between aromatic carboxylic acids and phenols catalyzed by basic catalysts. This parameter change eliminates the need for excess aromatic carboxylic acid ester, allowing stoichiometric reactions with complete conversion and maximum production amount per reaction volume.
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 efficient and cost-effective production of (meth) acrylic acid esters and aromatic carboxylic acid esters with improved productivity and reduced environmental impact, overcoming previous inefficiencies and waste management issues.
Implementation Method 1
the reaction of (meth) acrylic anhydride and a carbonate compound in the presence of a catalyst, such as nitrogenous base-containing organic compounds, Group I metal compounds, or Group II metal compounds
Data Source
Figure 1~2
AI summary
Provided is a method capable of efficiently manufacturing (meth)acrylic acid esters and aromatic carboxylic acid esters. This (meth)acrylic acid ester manufacturing method reacts a (meth)acrylic anhydride with a carbonate compound. For this aromatic carboxylic acid ester manufacturing method, which reacts a carboxylic anhydride with an aromatic carbonate in the presence of a catalyst, the catalyst is at least one kind selected from a set consisting of basic nitrogen-containing organic compounds, Group 1 metal compounds, and Group 2 metal compounds.