Fluorinated Unsaturated Cyclic Carbonate for Battery Electrolytes

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Solution Overview

Problem

There is no known unsaturated cyclic carbonate containing a fluorinated alkyl group or a method for its production, which limits its application in electrolyte solutions for lithium ion secondary batteries.

Innovation Solution

A novel fluorinated unsaturated cyclic carbonate is synthesized using methods involving fluoroalkylation, halogenation, reaction with carbon dioxide, or modification of vinylene carbonate, and its production processes are detailed to create an electrolyte solution for lithium ion secondary batteries.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If conventional vinylene carbonate or fluorinated carbonate is used in electrolyte solutions, then the electrolyte solution can be formulated, but the stability and performance at high temperatures are insufficient

Engineering Contradiction:

Improvestability of electrolyte solutionVSAvoidhigh temperature performance

Core Design Contradiction:

ReliabilityVSTemperature

Solution Approach 1:

The patent modifies the chemical structure of conventional vinylene carbonate by introducing fluorinated alkyl groups at specific positions (4-fluoro, 5-alkyl configuration). This structural parameter change enhances the electrolyte's stability at high temperatures while maintaining its functional properties, directly resolving the contradiction between conventional formulation capability and high-temperature performance.

Inventive Principle:

Principle #35Parameter changes

Solution Approach 2:

The invention creates a composite molecular structure by combining the vinylene carbonate backbone with fluorinated alkyl substituents. This composite approach integrates the beneficial properties of both the cyclic carbonate structure and fluorinated groups, achieving improved high-temperature stability while retaining electrolyte solution functionality.

Inventive Principle:

Principle #40Composite materials

2Reliability

If new fluorinated unsaturated cyclic carbonate is synthesized, then the stability and efficiency of electrolyte solution is improved, but the manufacturing process complexity increases

Engineering Contradiction:

Improveefficiency of lithium ion secondary batteryVSAvoidproduction process complexity

Core Design Contradiction:

ReliabilityVSDevice complexity

Solution Approach 1:

The patent employs preliminary functionalization by introducing fluorinated alkyl groups at specific positions on the vinylene carbonate structure before final electrolyte formulation. This pre-established structural modification simplifies the overall production process by avoiding more complex post-synthesis modifications, thus reducing manufacturing complexity while achieving the desired high efficiency and stability.

Inventive Principle:

Principle #10Preliminary action

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 novel unsaturated cyclic carbonate enhances the performance of electrolyte solutions by providing a component that improves the stability and efficiency of lithium ion secondary batteries, with high capacity recovery and reduced gas generation even at high temperatures.

Implementation Method 1

reacting a compound (3-1) represented by the following formula (3-1) with a halogenating agent to provide a compound (3-2)

Methodology Applied

Scientific EffectHalogenation:

Implementation Method 2

reacting the compound (3-2) with a base or metal to provide a compound represented by the following formula (1)

Methodology Applied

Scientific EffectElimination reaction:

Implementation Method 3

reacting a compound (4-1) represented by the following formula (4-1), with carbon dioxide to provide a compound (4-2)

Methodology Applied

Scientific EffectCarbonation reaction:

Implementation Method 4

reacting a compound (2-1) represented by the following formula (2-1) with a fluoroalkylating agent to provide a compound represented by the following formula (1)

Methodology Applied

Scientific EffectFluoroalkylation:

Data Source

PatentEP3750884B1Novel fluorinated unsaturated cyclic carbonate and process for producing the same

Publication Date: 2022.03.30 DAIKIN INDUSTRIES LTD

AI summary

The present invention provides a process for producing a compound of formula (1) wherein Rf is C1-8-fluoroalkyl: comprising reacting vinylene carbonate with a compound of the formula Rf-X (5-1) wherein Rf is C1-8-fluoroalkyl and X is a halogen atom, to provide a compound of formula (5-2): wherein Rf and X are as defined above, and reacting the compound of formula (5-2) with a base or metal.