Bis(Halogeno Sulfonyl)imide Synthesis Without Base or Solvent

Resolve Bottlenecks,
Find Innovative Solutions
Generate Solutions

Solution Overview

Problem

Existing methods for manufacturing lithium bis(fluorosulfonyl)imide (LiFSI) intermediates are complex, costly, and generate significant solid waste, lacking efficient industrial-scale processes.

Innovation Solution

A process involving the reaction of sulfuryl halogenide with ammonium compounds in the absence of a base, allowing for the production of bis(halogeno sulfonyl)imide intermediates, which can be recycled and controlled to minimize exothermic and side reactions, reducing environmental impact and complexity.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If conventional fluorination methods with fluorinating agents in solvents are used, then LiFSI can be manufactured, but the process becomes complex and costly with significant solid waste generation

Engineering Contradiction:
Improvemanufacturing capabilityVSAvoidprocess complexity
Core Design Contradiction:
ReliabilityVSDevice complexity

Solution Approach 1:

The invention extracts and eliminates the base component from the conventional fluorination process. By reacting sulfuryl fluoride directly with ammonium salt without requiring a base, the process removes the base addition step, filtration step for base removal, and associated waste streams, thereby simplifying the process while maintaining manufacturing capability

Inventive Principle:
Principle #2Taking out (Extraction)

Solution Approach 2:

The invention discards the base and solvent components from the conventional process. The direct reaction between sulfuryl fluoride and ammonium salt eliminates the need for base catalysts and organic solvents, reducing process complexity and solid waste generation while preserving the core manufacturing function

Inventive Principle:
Principle #34Discarding and recovering

2Productivity

If base is added to the reaction between sulfuryl halogenide and ammonium compound, then the reaction proceeds, but solid waste increases and process complexity increases

Engineering Contradiction:
Improvereaction efficiencyVSAvoidsolid waste
Core Design Contradiction:
ProductivityVSLoss of substance

Solution Approach 1:

The ammonium salt itself serves the dual function of providing both the nitrogen source and the base equivalent needed for the reaction. The ammonium ion (NH4+) directly reacts with sulfuryl fluoride to form the desired product and HF byproduct, eliminating the need for separate base addition and reducing solid waste

Inventive Principle:
Principle #25Self-service

3Manufacturing precision

If base is used in the reaction process, then intermediate compounds can be formed, but the process becomes less suitable for industrial scale due to waste and complexity

Engineering Contradiction:
Improveintermediate compound formationVSAvoidindustrial scalability
Core Design Contradiction:
Manufacturing precisionVSEase of manufacture

Solution Approach 1:

The invention extracts the base component from the reaction system, allowing intermediate compound formation to proceed through direct reaction between sulfuryl fluoride and ammonium salt. This elimination of base simplifies the process for industrial scaling while maintaining the ability to form necessary intermediates

Inventive Principle:
Principle #2Taking out (Extraction)

Solution Approach 2:

The invention changes the reaction parameters by removing base and solvent components, adjusting the reaction conditions to direct reaction between sulfuryl fluoride and ammonium salt. This parameter change simplifies the manufacturing process for industrial application while maintaining intermediate compound formation capability

Inventive Principle:
Principle #35Parameter changes

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 process simplifies the manufacturing of LiFSI intermediates by minimizing waste generation and enabling easy control of reactions, making it suitable for industrial application.

Implementation Method 1

The reaction between compounds of formula (I) and (II) is conducted in the presence of a first base, to provide a bis(sulphonyl)imide

Methodology Applied
Scientific EffectChemical reaction: Chemical Bonding

Implementation Method 2

enabling easy control of reactions, making it suitable for industrial application

Methodology Applied
Scientific EffectExothermic reaction: Exothermic Reaction

Data Source

PatentEP4590631B1Method for manufacturing bis(halogeno sulfonyl)imide
Publication Date: 2026.03.18 SPECIALTY OPERATIONS FRANCE
  • EP4590631B1 patent drawing
  • EP4590631B1 patent drawing
  • EP4590631B1 patent drawing

AI summary

The present invention relates to a new synthetic pathway for manufacturing bis(halogeno sulfonyl)imide, which are useful intermediates in the synthesis of lithium bis(fluorosulfonyl)imide (LiFSI).