Fluorinated Electrolyte Solvent Synthesis via Chlorine-Free Reaction

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Solution Overview

Problem

Current methods for producing high voltage electrolyte solvents, such as fluorinated carbonates, are inefficient, costly, and environmentally hazardous due to the use of severe reactants and toxic reagents, requiring elaborate purification steps and controlled atmospheres, which limits their commercial viability.

Innovation Solution

A method using a halogenated alcohol and a nitrogen-containing carbonyl compound in an ethereal reaction solvent at mild temperatures and ambient pressures, eliminating the need for anhydrous conditions and chlorine-free, achieving high yields and purity with a single distillation and filtration step.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If state of the art methods using phosgene, triphosgene, or hexachloroacetone are used to produce fluorinated carbonate solvents, then the solvents achieve high electrochemical stability for high voltage batteries, but the process requires elaborate distillation and purification steps to remove chlorine traces and chloride ions

Engineering Contradiction:
Improveelectrochemical stabilityVSAvoidpurification process complexity
Core Design Contradiction:
ReliabilityVSDevice complexity

Solution Approach 1:

The invention extracts and eliminates the harmful chlorine-containing reagents (phosgene, triphosgene, hexachloroacetone) from the synthesis process entirely, replacing them with chlorine-free alternatives that do not require elaborate purification steps to remove chlorine traces and chloride ions

Inventive Principle:
Principle #2Taking out (Extraction)

Solution Approach 2:

The invention converts the harmful effect of chlorine-containing reagents by completely eliminating their use, thereby eliminating the need for complex purification equipment and procedures while maintaining the desired electrochemical stability of the final product

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

2Quantity of substance

If state of the art methods using toxic reagents like phosgene and triphosgene are used, then fluorinated carbonate solvents can be produced, but the process generates significant amounts of waste and requires additional aqueous treatments

Engineering Contradiction:
Improveproduct yieldVSAvoidwaste generation
Core Design Contradiction:
Quantity of substanceVSLoss of substance

Solution Approach 1:

The invention converts the harmful waste-generating process into a clean process by eliminating toxic reagents like phosgene and triphosgene, thereby eliminating the need for aqueous treatment steps and significantly reducing waste generation while maintaining product yield

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

Solution Approach 2:

The invention changes the chemical parameters of the reaction system by using alternative reagents with different chemical properties that do not produce harmful byproducts, thereby eliminating the need for waste treatment steps

Inventive Principle:
Principle #35Parameter changes

3Reliability

If state of the art methods require internal temperatures of 100° C. maintained for 20 hours or more, then fluorinated carbonate solvents can be produced, but the production time is excessively long and economically unviable

Engineering Contradiction:
Improveproduct purityVSAvoidproduction time
Core Design Contradiction:
ReliabilityVSLoss of time

Solution Approach 1:

The invention changes the reaction parameters by using a different chemical pathway that proceeds rapidly at room temperature, reducing the reaction time from 20 hours or more to just 2-3 hours while maintaining product purity through the inherent selectivity of the new reaction system

Inventive Principle:
Principle #35Parameter changes

4Reliability

If state of the art methods require strictly anhydrous reaction conditions in nitrogen-filled gloveboxes, then fluorinated carbonate solvents can be produced, but the process becomes too costly and cumbersome for commercial viability

Engineering Contradiction:
Improvereaction controlVSAvoidcommercial viability
Core Design Contradiction:
ReliabilityVSEase of manufacture

Solution Approach 1:

The invention extracts and eliminates the requirement for strictly anhydrous conditions and nitrogen-filled gloveboxes by using reagents and reaction conditions that are tolerant of moisture and air, thereby dramatically simplifying the manufacturing process and improving commercial viability

Inventive Principle:
Principle #2Taking out (Extraction)

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 significantly reduces production time, minimizes waste, and achieves high yields and purity of halogenated carbonates like bis(trifluoroethyl) carbonate and trifluoropropylene carbonate, making them more economically viable for lithium-ion battery applications.

Implementation Method 1

A method using a halogenated alcohol and a nitrogen-containing carbonyl compound in an ethereal reaction solvent

Methodology Applied
Scientific EffectChemical reaction: Chemical Bonding

Implementation Method 2

achieves high yields and purity with a single distillation and filtration step

Methodology Applied
Scientific EffectDistillation: Distillation

Implementation Method 3

achieves high yields and purity with a single distillation and filtration step

Methodology Applied
Scientific EffectFiltration: Filter (physical)

Data Source

PatentUS10294189B2Process for producing fluorinated electrolyte solvent
Publication Date: 2019.05.21 UCHICAGO ARGONNE LLC
  • US10294189B2 patent drawing
  • US10294189B2 patent drawing
  • US10294189B2 patent drawing

AI summary

The invention provides a method for producing halogenated carbonates, the method comprising reacting a halogenated alcohol or diol with a solid source of carbonyl moiety as a base in an ether.