One-Pot Sulfonimide Synthesis for Broad Ionic Salt Production
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Solution Overview
Problem
Existing methods for synthesizing ionic compounds, such as perfluorosulfonimide derivatives, are wasteful, time-consuming, and limited in scope, leading to inefficient production of electrolytes with low ionic conductivity, particularly in solid electrolytes.
Innovation Solution
A one-pot method involving the reaction of a N-(sulfinyl)sulfonamide with a sulphonamide salt, followed by oxidation and cation exchange, to produce ionic compounds with a delocalized anionic charge, enhancing total ionic conductivity.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Ease of manufacture
If conventional multi-step synthesis methods are used to prepare perfluorosulfonimide derivatives, then the synthetic scope is limited and isolation is unsuccessful, but the production process is time-consuming and wasteful
Solution Approach 1:
The patent combines multiple synthesis steps into a single one-pot reaction sequence. The reaction of N-(sulfinyl)sulfonamide with sulphonamide salt followed by in-situ oxidation with m-CPBA eliminates the need for intermediate isolation and purification steps, significantly reducing waste and time consumption while maintaining high product yield
Solution Approach 2:
The synthesis process maintains continuous reaction conditions without interruption for isolation or purification. The oxidation step occurs in-situ after the initial reaction, allowing the useful chemical transformation to continue uninterrupted, thereby eliminating waste associated with intermediate handling and reducing overall process time
2Adaptability or versatility
If existing synthesis routes are used for ionic compounds, then the process is scope-limited, but it requires time-consuming and wasteful synthetic steps
Solution Approach 1:
The one-pot synthesis methodology demonstrated in the patent can be applied to prepare various perfluorosulfonimide derivatives with different cations (Li+, Na+, K+, etc.) and different R groups, providing a universal approach that expands synthetic scope while reducing the time required for each specific compound preparation
3Reliability
If conventional electrolytes are used in solid electrolytes, then the ionic conductivity is low, but the stability is insufficient
Solution Approach 1:
The patent introduces ionic compounds with delocalized anionic charge as a new class of electrolyte materials. By changing the chemical composition to include compounds like perfluorosulfonimide derivatives with extended pi-conjugation and charge delocalization, the ionic conductivity is significantly enhanced while maintaining chemical and thermal stability
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 method achieves higher step-and atom-economy, milder conditions, and produces a broad range of ionic compounds with improved ionic conductivity, suitable for solid electrolytes.
Implementation Method 1
oxidizing the compound of formula (IV) with a reagent selected from a fluorination reagent, a chlorination reagent, a bromination reagent, a iodination reagent, an alkylation reagent, and an amination reagent
Implementation Method 2
carrying out a cation exchange reaction to replace the monovalent or divalent cation M of the salt of formula (I) resulting from step b) by a trivalent or polyonium cation
Data Source
AI summary
The present invention provides a method for obtaining ionic compounds of formula (I) which comprises two-steps carried out in a one-pot manner. Said method includes the reaction of a N-(sulfinyl)sulfonamide of formula R1SO2N=S=O with a sulphonamide salt of formula R2SO2N(M)m, followed by the oxidation of the resulting compound. The new route displays several advantages compared to previous methods to access sulfonimides, among them a) a short sequence of steps, short reaction time, avoidance of environmentally-unfriendly reagents (such as CF3SiMe3), improved atom-economy, milder conditions, as well as the ability to synthesize a broad range of salts.