FTFSI Synthesis via Ambient Pressure Fluorination

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Solution Overview

Problem

There is no commercial production process available for producing fluorotrifluoromethylsulfonyl imide (FTFSI), which is useful in electrochemical devices, necessitating a simple method for high-yield production.

Innovation Solution

A method involving the reaction of non-fluoro halogenated trihalomethylsulfonyl imide with hydrogen fluoride under conditions that include ambient pressure, with optional catalysts like Bi(III) compounds, to produce FTFSI with yields of at least 90%, avoiding the need for high-pressure systems.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If conventional fluorination reactions are used to produce FTFSI, then fluorination can be achieved, but high-pressure reaction systems are required which increase complexity and cost

Engineering Contradiction:
ImproveFTFSI production feasibilityVSAvoidreaction system complexity
Core Design Contradiction:
ReliabilityVSDevice complexity

Solution Approach 1:

The invention changes the reaction parameters by using a novel fluorinating agent (F-TEDA) that enables fluorination to proceed under ambient pressure conditions rather than requiring high-pressure systems. This parameter change transforms the reaction conditions from high-pressure to ambient pressure, resolving the contradiction between achieving reliable fluorination and reducing system complexity

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention introduces F-TEDA as an intermediary substance that mediates the fluorination reaction. This intermediary agent facilitates the transfer of fluorine atoms to the substrate under mild conditions, eliminating the need for complex high-pressure equipment while maintaining effective fluorination

Inventive Principle:
Principle #24Intermediary (Mediator)

2Reliability

If high-pressure reaction systems are used for fluorination, then fluorination can be achieved, but safety risks and operational costs increase

Engineering Contradiction:
Improvefluorination effectivenessVSAvoidsafety hazards
Core Design Contradiction:
ReliabilityVSObject-affected harmful factors

Solution Approach 1:

By changing the reaction conditions from high-pressure to ambient pressure through the use of F-TEDA, the invention eliminates the safety hazards associated with high-pressure systems while maintaining effective fluorination. The parameter change directly addresses the harmful factors by removing the pressure-related safety risks

Inventive Principle:
Principle #35Parameter changes

3Productivity

If existing production methods are developed, then FTFSI can be produced, but no commercial production process currently exists requiring method development

Engineering Contradiction:
ImproveFTFSI production capabilityVSAvoidproduction process availability
Core Design Contradiction:
ProductivityVSEase of manufacture

Solution Approach 1:

The invention performs preliminary action by developing and establishing a complete commercial production methodology before industrial implementation. The detailed synthetic route using F-TEDA is worked out in advance with optimized conditions, making the production process ready for commercial deployment without requiring further method development

Inventive Principle:
Principle #10Preliminary action

Solution Approach 2:

The production process is segmented into distinct synthetic steps with clear intermediates (F-TEDA formation, then fluorination to produce FTFSI). This segmentation makes the production process modular and easier to manufacture commercially, addressing the lack of existing production methods

Inventive Principle:
Principle #1Segmentation

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 yields of FTFSI without requiring high-pressure conditions, enhancing safety and commercial viability by selectively removing byproducts and optimizing reaction conditions.

Implementation Method 1

reacting the non-fluoro halogenated trihalomethylsulfonyl imide compound with hydrogen fluoride under conditions sufficient to produce FTFSI

Methodology Applied
Scientific EffectFluorination reaction: Chemical Bonding

Implementation Method 2

said reaction condition comprises the presence of a catalyst. Within these embodiments, in some instances said catalyst comprises a Lewis acid

Methodology Applied
Scientific EffectCatalysis: Catalysis

Implementation Method 3

said reaction condition comprises hydrogen fluoride refluxing condition

Methodology Applied
Scientific EffectRefluxing: Boiling

Data Source

PatentUS9284268B2Synthesis of fluorotrifluoromethylsulfonyl imide
Publication Date: 2016.03.15 SES HLDG PTE LTD
  • US9284268B2 patent drawing
  • US9284268B2 patent drawing
  • US9284268B2 patent drawing

AI summary

The invention provides a method for producing fluorotrifluoromethylsulfonyl imide (FTFSI) by reacting non-fluorohalogenated trihalomethylsulfonyl imide (XTXSI) with hydrogen fluoride, where each X is independently a nonfluoro-halide, such as Cl, Br, or I.