Halogenated Carbonate Production via Solid Base Catalysis

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Solution Overview

Problem

Current methods for producing high voltage electrolyte solvents are inefficient, requiring severe reactants and conditions, generating significant waste, and necessitating costly anhydrous environments and lengthy processing times, which makes them commercially unviable.

Innovation Solution

A method using a common non-halogenated solvent and a solid inorganic base to produce halogenated carbonates at mild temperatures, eliminating the need for anhydrous conditions and reducing waste, with a process that can be completed within 1-4 hours using ambient atmosphere and pressures.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Productivity

If state of the art methods use halogenated solvents and organic bases for producing electrolyte solvents, then the reaction can proceed, but the yields are low (30-40 percent) and significant waste is generated

Engineering Contradiction:
ImproveyieldVSAvoidwaste
Core Design Contradiction:
ProductivityVSLoss of substance

Solution Approach 1:

The invention changes the chemical parameters by replacing halogenated solvents with non-halogenated solvents (acetone, diethyl ether, ethyl methyl ketone) and replacing organic bases with inorganic bases (carbonates, phosphates). This parameter change leads to improved yields (60-80%) and reduced waste generation while maintaining reaction effectiveness.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention uses common, inexpensive reagents such as acetone and potassium carbonate that can be easily disposed of or recycled, replacing expensive and hazardous halogenated solvents and organic bases. This approach reduces both cost and environmental impact while improving process efficiency.

Inventive Principle:
Principle #27Cheap short-living objects (Disposable)

2Manufacturing precision

If state of the art methods require anhydrous conditions and nitrogen-filled gloveboxes, then the reaction purity is maintained, but the process becomes costly and cumbersome

Engineering Contradiction:
ImprovepurityVSAvoidprocess complexity
Core Design Contradiction:
Manufacturing precisionVSEase of manufacture

Solution Approach 1:

The invention uses inorganic bases (carbonates, phosphates) that are inherently stable and do not require strictly anhydrous conditions to function effectively. The reagents self-regulate the reaction environment, eliminating the need for complex nitrogen-filled glovebox setups while maintaining product purity.

Inventive Principle:
Principle #25Self-service

Solution Approach 2:

The invention replaces the need for inert nitrogen atmosphere with reactions that can proceed in ambient air. The use of inorganic bases and non-halogenated solvents creates a naturally more stable reaction environment that does not require exclusion of moisture or oxygen, simplifying the manufacturing process.

Inventive Principle:
Principle #39Inert atmosphere (Inert environment)

3Productivity

If state of the art methods use halogenated reactants such as dichloromethane, then the reaction proceeds efficiently, but residual impurities wreak havoc in battery chemistries requiring extensive filtration and purification

Engineering Contradiction:
Improvereaction efficiencyVSAvoidresidual impurities
Core Design Contradiction:
ProductivityVSObject-generated harmful factors

Solution Approach 1:

The invention converts the potential harm of using common solvents like acetone (which can form peroxides) into a benefit by selecting solvents and conditions that avoid this issue entirely. The use of inorganic bases and specific non-halogenated solvents eliminates the formation of harmful halogenated impurities while maintaining reaction efficiency.

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

Solution Approach 2:

The invention extracts and removes halogenated reagents from the reaction system entirely, replacing them with non-halogenated alternatives. This elimination approach prevents the formation of harmful residual impurities that would otherwise require extensive filtration and purification steps.

Inventive Principle:
Principle #2Taking out (Extraction)

4Manufacturing precision

If state of the art methods require 8-20 hours for completion in controlled atmospheres, then the product purity is achieved, but the processing time is too long for commercial viability

Engineering Contradiction:
Improveproduct purityVSAvoidprocessing time
Core Design Contradiction:
Manufacturing precisionVSLoss of time

Solution Approach 1:

The invention enables continuous reaction progress without the need for interrupted purification steps or extended waiting periods. The use of inorganic bases and non-halogenated solvents allows the reaction to proceed continuously to completion (60-80% yield in 1-4 hours) with minimal intervention, achieving both purity and speed.

Inventive Principle:
Principle #20Continuity of useful action

Solution Approach 2:

The invention skips the lengthy purification steps traditionally required by using reagents that do not generate problematic byproducts. The reaction rushes through to completion in 1-4 hours with simple filtration and distillation sufficing for purification, eliminating the need for prolonged processing times.

Inventive Principle:
Principle #21Skipping (Rushing through)

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 achieves high yields and purity of halogenated carbonates, such as trifluoroethyl methyl carbonate, with simplified filtration and distillation, reducing processing time and waste generation, making the process more economically viable.

Implementation Method 1

reacting a halogenated hydroxyl moiety with an alkyl chloroformate in the presence of a liquid solvent and a solid base

Methodology Applied
Scientific EffectCatalysis: Catalysis

Implementation Method 2

The liquid solvent is a nonhalogenated compound selected from the group consisting of acetone, diethyl ketone, ethyl methyl ketone, acetophenone, cyclohexyl methyl ketone and combinations thereof

Methodology Applied
Scientific EffectSolvation: Solvation

Implementation Method 3

simplified filtration and distillation

Methodology Applied
Scientific EffectFiltration: Filter (physical)

Implementation Method 4

purification of fluorinated carbonate solvents is a difficult fractional distillation

Methodology Applied
Scientific EffectDistillation: Distillation

Data Source

PatentUS10099994B2Process for the production of high voltage electrolyte solvents for Li-ion batteries
Publication Date: 2018.10.16 UCHICAGO ARGONNE LLC
  • US10099994B2 patent drawing

AI summary

A method for producing halogenated carbonates is provided, the method having the steps of reacting a halogenated hydroxyl moiety with an alkyl formate in the presence of a liquid solvent and a solid base. An exemplary halogenated carbonate so produced is trifluoroethyl methyl carbonate.