Carboxylic Acid Thioester Synthesis via Group 2 Catalyst
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Solution Overview
Problem
Existing methods for producing carboxylic acid thioester are economically inefficient due to the use of large solvents, generate significant waste, and pose health risks, with complex operation procedures and environmental concerns.
Innovation Solution
A method involving the reaction of a compound represented by formula (I), carboxylic acid, and thiol in the presence of a catalyst including Group 2 and Group 1 metal compounds, which allows for solvent-free production at normal temperature and pressure, reducing by-products and simplifying the operation.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Reliability
If a large amount of solvent is used in the reaction, then the reaction can proceed smoothly, but the production efficiency decreases and waste increases
Solution Approach 1:
The patent changes the reaction parameters by using a specific catalyst system (Group 2 metal compound with halide and/or pseudohalide) that enables the reaction to proceed efficiently without requiring large amounts of solvent, thus improving production efficiency while maintaining reaction smoothness
Solution Approach 2:
The patent eliminates the need for washing steps to remove by-products by designing a reaction system where the catalyst and reagents are selected to minimize harmful by-product formation, thereby reducing waste and improving production efficiency
2Speed
If methacryloyl chloride is used as substrate, then the reaction proceeds rapidly, but hydrochloride by-product is generated requiring washing steps
Solution Approach 1:
The patent extracts or removes the harmful by-product generation issue by selecting alternative substrates (carboxylic acid compounds) and catalysts that do not produce hydrochloride, thereby eliminating the need for washing steps while maintaining acceptable reaction rates
Solution Approach 2:
The patent converts the potentially harmful reaction between carboxylic acid and thiol into a beneficial process by using a catalyst system that promotes this otherwise slow reaction, turning a previously undesirable slow reaction into an efficient process without harmful by-products
3Ease of manufacture
If N,N′-dicyclohexylcarbodiimide is used as substrate, then the reaction can proceed, but 1,3-dicyclohexylurea by-product is generated and allergic symptoms occur
Solution Approach 1:
The patent removes the harmful substrate (N,N′-dicyclohexylcarbodiimide) and replaces it with carboxylic acid compounds that do not generate toxic by-products or cause allergic symptoms, thereby maintaining reaction feasibility while eliminating harmful factors
Solution Approach 2:
The patent uses readily available carboxylic acid compounds as substrates that can be easily handled and do not require special precautions against allergic reactions, simplifying the manufacturing process and improving safety
4Reliability
If thiol and methacryloyl chloride are added separately at 5°C, then the reaction can be controlled, but the operation becomes complicated
Solution Approach 1:
The patent merges the addition of reagents into a single step at normal temperature, combining multiple operational steps into one simple operation while maintaining reaction control through the catalyst system, thereby improving ease of operation without sacrificing reliability
5Manufacturing precision
If washing step is incorporated to remove by-product, then the product purity increases, but waste production increases
Solution Approach 1:
The patent extracts or eliminates the need for washing steps by designing a reaction system that produces minimal harmful by-products, achieving product purity through the reaction design itself rather than through post-reaction purification, thereby reducing waste production
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 achieves high-yield, solvent-free production of carboxylic acid thioester with reduced environmental and health impacts, improving efficiency and economic performance.
Implementation Method 1
reacting a compound represented by the following formula (I), carboxylic acid and thiol in the presence of a catalyst including at least one Group 2 metal compound
Data Source
AI summary
According to the present invention, there is provided a method for producing carboxylic acid thioester, comprising reacting a compound represented by the following formula (I), carboxylic acid and thiol in the presence of a catalyst including at least one Group 2 metal compound. The production method is a production method which is simple in reaction operation, which places a small load on the environment and the human body and which enables carboxylic acid thioester to be catalytically obtained at a high yield even at a normal temperature and a normal pressure (25° C., 1 atm). In the formula (I), R1 and R2 each independently represent a hydrocarbon group having 1 to 20 carbon atoms.