Fluorosulfonyl Monomer Synthesis with Fewer Steps and Higher Yield
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Solution Overview
Problem
The production of monomers with two fluorosulfonyl groups is hindered by low yield and high costs due to expensive starting materials and numerous synthetic steps, making conventional methods inefficient and costly.
Innovation Solution
A method involving the reaction of specific compounds with sulfonating, chlorinating, and fluorinating agents, followed by fluorination treatment, to produce fluorosulfonyl group-containing compounds and monomers with two fluorosulfonyl groups in a few synthetic steps, reducing material costs and increasing efficiency.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Productivity
If conventional methods using benzyl mercaptan and epichlorohydrin are used to produce monomers with two fluorosulfonyl groups, then the monomer can be synthesized, but the yield is low (2% on starting material basis) and the cost is high due to expensive starting materials and numerous synthetic steps
Solution Approach 1:
The patent changes the chemical parameters by using different starting materials (perfluoroallyl alcohol instead of benzyl mercaptan and epichlorohydrin) and different reagents (trifluoromethanesulfonic acid and sulfur trioxide complex instead of conventional sulfonating agents). This parameter change leads to a dramatic improvement in yield from 2% to over 80% while reducing the number of synthetic steps and manufacturing cost
Solution Approach 2:
The patent extracts and eliminates the problematic intermediate steps from the conventional synthesis route. By using perfluoroallyl alcohol as a direct starting material, the method removes the need for multiple intermediate transformations, thereby increasing yield and simplifying the manufacturing process
2Productivity
If conventional methods with multiple synthetic steps are used, then the monomer can be produced, but the number of synthetic steps is large and the process is complex
Solution Approach 1:
The patent merges multiple synthetic operations into a streamlined sequence. The use of trifluoromethanesulfonic acid and sulfur trioxide complex allows for combined sulfonation and fluorination steps, reducing the total number of synthetic operations while maintaining high efficiency and product quality
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 allows for the production of fluorosulfonyl group-containing compounds and monomers at a lower cost with fewer steps, resulting in polymers with high ion exchange capacity and excellent ion conductivity, enhancing the performance of fuel cells and electrolysis processes.
Implementation Method 1
reacting a compound represented by the following formula (1) with a sulfonating agent to obtain a compound represented by the following formula (2)
Implementation Method 2
reacting the compound represented by the following formula (2) with a chlorinating agent to obtain a compound represented by the following formula (3)
Implementation Method 3
reacting the compound represented by the following formula (3) with a fluorinating agent to obtain a compound represented by the following formula (4)
Implementation Method 4
subjecting the compound represented by the following formula (4) to fluorination treatment to obtain a compound represented by the following formula (5)
Data Source
AI summary
A method for producing a fluorosulfonyl group-containing compound to obtain a compound represented by the following formula 5 from a compound represented by the following formula 1 as a starting material and a method for producing a fluorosulfonyl group-containing monomer in which the fluorosulfonyl group-containing compound is used:wherein R1 and R2 are a C1-3 alkylene group, and RF1 and RF2 are a C1-3 perfluoroalkylene group.