Fluoroolefin Electrolyte Additive for Stable Electrode Interface Films

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Solution Overview

Problem

There is a need for a novel compound that can be used as a solvent, cleaning agent, foaming agent, and intermediate for functional materials, and also as an additive for nonaqueous electrolytic solutions in secondary batteries, with properties such as self-extinguishing and chemical stability.

Innovation Solution

The production of 1,1,1,5,5,5-hexafluoro-3-(2,2,2-trifluoroethoxy)-2-pentene through the reaction of 1,1,1,5,5,5-hexafluoro-3-chloro-2-pentene with 2,2,2-trifluoroethanol in the presence of a base, using a phase-transfer catalyst, to create a compound that can be used in nonaqueous electrolytic solutions for secondary batteries.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If a novel fluoroolefin compound is developed for use in nonaqueous electrolytic solutions, then battery performance (cycle characteristics and capacity retention) is improved, but the complexity of compound synthesis and purification increases

Engineering Contradiction:
Improvebattery cycle characteristicsVSAvoidsynthesis process complexity
Core Design Contradiction:
ReliabilityVSDevice complexity

Solution Approach 1:

The synthesis process is divided into distinct stages: (1) preparation of 1,1,1,5,5,5-hexafluoro-3-chloro-2-pentene as an intermediate, (2) nucleophilic substitution reaction with 2,2,2-trifluoroethanol, and (3) purification through washing and drying. This segmentation allows each step to be optimized independently, improving overall reliability while managing complexity.

Inventive Principle:
Principle #1Segmentation

Solution Approach 2:

A phase transfer catalyst is introduced as an intermediary substance to facilitate the reaction between 1,1,1,5,5,5-hexafluoro-3-chloro-2-pentene and 2,2,2-trifluoroethanol. The catalyst mediates the reaction process, enabling efficient synthesis of the novel compound without requiring complex reaction conditions or additional equipment.

Inventive Principle:
Principle #24Intermediary (Mediator)

2Stability of the object's composition

If the compound is produced through multi-step synthesis, then the desired chemical structure and properties are achieved, but the manufacturing cost and time increase

Engineering Contradiction:
Improvechemical stabilityVSAvoidsynthesis time
Core Design Contradiction:
Stability of the object's compositionVSLoss of time

Solution Approach 1:

The intermediate compound 1,1,1,5,5,5-hexafluoro-3-chloro-2-pentene is prepared in advance through a established synthesis route before being used in the final substitution reaction. This preliminary preparation allows the final step to proceed efficiently with well-characterized starting materials, reducing overall synthesis time while maintaining compositional stability.

Inventive Principle:
Principle #10Preliminary action

Solution Approach 2:

The synthesis conditions are optimized by adjusting parameters such as temperature, solvent composition, and catalyst concentration to achieve the desired chemical structure. By carefully controlling these parameters, the reaction proceeds efficiently to produce the stable fluoroolefin compound with the correct stereochemistry and purity in reduced time.

Inventive Principle:
Principle #35Parameter changes

3Device complexity

If conventional electrolyte additives are used, then the electrolyte formulation is simple, but the film formation quality on electrode interfaces is insufficient

Engineering Contradiction:
Improveelectrolyte formulation complexityVSAvoidfilm formation quality
Core Design Contradiction:
Device complexityVSManufacturing precision

Solution Approach 1:

The electrolyte is formulated as a composite system containing the novel fluoroolefin compound (1,1,1,5,5,5-hexafluoro-3-(2,2,2-trifluoroethoxy)-2-pentene) combined with conventional electrolyte components. This composite formulation leverages the unique properties of the fluoroolefin compound to form high-quality protective films on electrode interfaces, while maintaining compatibility with standard electrolyte systems.

Inventive Principle:
Principle #40Composite materials

Solution Approach 2:

The fluoroolefin compound specifically targets the electrode interface region to form protective films, providing localized improvement in film formation quality. The compound's molecular structure and reactivity are designed to interact preferentially with electrode surfaces, creating a thin, uniform protective layer that enhances battery performance without requiring changes to the bulk electrolyte composition.

Inventive Principle:
Principle #3Local 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

The compound forms a good film on electrode interfaces, enhancing battery properties and providing high affinity with electrodes, leading to improved cycle characteristics and capacity retention in secondary batteries.

Implementation Method 1

reacting 1,1,1,5,5,5-hexafluoro-3-chloro-2-pentene with 2,2,2-trifluoroethanol in the presence of a base

Methodology Applied
Scientific EffectNucleophilic substitution reaction: Chemical Bonding

Implementation Method 2

the reaction is carried out in the presence of a phase-transfer catalyst

Methodology Applied
Scientific EffectPhase transfer catalysis: Catalysis

Data Source

PatentUS20250276948A11,1,1,5,5,5-hexafluoro-3-(2,2,2-trifluoroethoxy)-2-pentene and uses and production method thereof
Publication Date: 2025.09.04 KANTO DENKA IND CO LTD
  • US20250276948A1 patent drawing
  • US20250276948A1 patent drawing
  • US20250276948A1 patent drawing

AI summary

Provided are a novel compound, 1,1,1,5,5,5-hexafluoro-3-(2,2,2-trifluoroethoxy)-2-pentene, and uses thereof and a method for producing this novel compound. According to the present invention, 1,1,1,5,5,5-hexafluoro-3-(2,2,2-trifluoroethoxy)-2-pentene is provided. This novel compound can be produced, for example, by reacting 1,1,1,5,5,5-hexafluoro-3-chloro-2-pentene with 2,2,2-trifluoroethanol in the presence of a base. This novel compound is also useful as an additive in a nonaqueous electrolytic solution for a secondary battery.