Fluorinated Cyclic Carbonate Synthesis for Li-Ion Battery Electrolytes

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Solution Overview

Problem

Current methods for manufacturing fluorinated alkyl carbonates as additives for lithium ion batteries and supercapacitors face challenges in yield, purity, energy consumption, safety, and side-product profiles, and existing additives do not adequately enhance battery performance or stability, particularly in the presence of copper substrates.

Innovation Solution

A method for manufacturing fluorinated cyclic carbonates involving the reaction of fluorosubstituted alkyl or alkyloxyalkylene compounds with alkaline metal cations or their equivalents, which improves yield, purity, and safety while forming beneficial films and enhancing electrolyte stability, wettability, and reducing flammability.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Manufacturing precision

If conventional methods are used to manufacture fluorinated alkyl carbonates, then the basic manufacturing process is simple, but the overall yield and purity of the desired product are insufficient

Engineering Contradiction:
Improvepurity of fluorinated cyclic carbonateVSAvoidcomplexity of manufacturing process
Core Design Contradiction:
Manufacturing precisionVSEase of manufacture

Solution Approach 1:

The manufacturing process is divided into distinct stages: first forming the fluorinated cyclic carbonate through reaction of fluorinated alkyl halide with carbonate source, then selectively purifying it from side products through extraction and distillation steps. This segmentation allows each step to be optimized independently, achieving high purity without excessive overall complexity.

Inventive Principle:
Principle #1Segmentation

Solution Approach 2:

The patent introduces intermediate purification steps including aqueous washing to remove halide byproducts, drying agents to remove water, and selective extraction processes. These intermediary steps act as mediators between the reaction stage and final product, enabling high purity output while maintaining reasonable process complexity.

Inventive Principle:
Principle #24Intermediary (Mediator)

2Use of energy by stationary object

If conventional manufacturing methods are used, then the process steps are fewer, but energy consumption is higher and safety requirements are more stringent

Engineering Contradiction:
Improveenergy consumption of manufacturing processVSAvoidoverall yield of fluorinated cyclic carbonate
Core Design Contradiction:
Use of energy by stationary objectVSProductivity

Solution Approach 1:

The patent optimizes reaction parameters including temperature control during the carbonation step, solvent selection and ratios, and pH control during workup. These parameter changes increase reaction efficiency and yield while reducing energy consumption through milder reaction conditions and more efficient separation processes.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent converts potentially harmful side reactions into beneficial outcomes by designing the reaction to produce water-soluble halide byproducts that can be easily removed through aqueous washing. This converts what would be harmful contaminants into easily separable substances, improving both yield and safety.

Inventive Principle:
Principle #22Blessing in disguise (Convert harm into benefit)

3Reliability

If existing fluorinated additives are used, then the basic electrolyte function is maintained, but stability towards reduction and oxidation is insufficient

Engineering Contradiction:
Improvestability of electrolyte compositionVSAvoiddegradation of current collector materials
Core Design Contradiction:
ReliabilityVSObject-generated harmful factors

Solution Approach 1:

The fluorinated cyclic carbonate provides localized protection at the electrode-electrolyte interface through formation of a stable solid electrolyte interphase (SEI) layer. This localized action at the critical interface region protects the current collector from degradation while maintaining bulk electrolyte stability, addressing the specific stability issue without requiring complete reformulation of the entire electrolyte system.

Inventive Principle:
Principle #3Local quality

4Duration of action of moving object

If traditional solvent additives are used, then the electrolyte composition is simple, but cycle life and performance properties are not optimized

Engineering Contradiction:
Improvecycle life of lithium ion batteryVSAvoidcomplexity of electrolyte composition
Core Design Contradiction:
Duration of action of moving objectVSDevice complexity

Solution Approach 1:

The patent employs fluorinated cyclic carbonate as a composite additive combining features of both cyclic carbonate (high dielectric constant, good ionic conductivity) and fluorinated alkyl compound (high stability, low reactivity). This composite molecular structure provides multiple benefits simultaneously: enhanced cycle life through improved SEI stability, maintained ionic conductivity, and increased oxidation resistance, without requiring complex mixtures of multiple additives.

Inventive Principle:
Principle #40Composite materials

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 fluorinated cyclic carbonates improve the performance of lithium ion batteries and supercapacitors by increasing stability, cycle life, and energy density, and allow for higher voltage operation, while also providing protection against over-charging and enhancing the stability of the electrolyte composition.

Implementation Method 1

the compounds of the present invention advantageously show a higher stability towards reduction and/or oxidation. Alternatively, the compounds of the present invention advantageously show a high stability towards oxidation while having a relatively low stability towards reduction. This property can lead to an increased performance of the battery, e.g. by modifying the electrodes of the battery, specifically by the formation on a protective layer on the electrode.

Methodology Applied
Scientific EffectElectrochemical reduction: Reduction

Implementation Method 2

The compounds of the invention can suitably assist in the protection against over-charging, for example, by serving as a redox shuttle.

Methodology Applied
Scientific EffectRedox reactions: Redox Reactions

Data Source

PatentUS10756389B2Method for the manufacture of fluorinated cyclic carbonates and their use for lithium ion batteries
Publication Date: 2020.08.25 SYENSQO SA
  • US10756389B2 patent drawing
  • US10756389B2 patent drawing
  • US10756389B2 patent drawing

AI summary

The present invention concerns methods for the manufacture of ethylene carbonate substituted with a fluorinated alkoxy group, certain ethylene carbonates substituted with a fluorinated alkoxy group as well as their use as solvent or solvent additive for lithium ion batteries and supercapacitors.