Sultone Derivatives Preparation via Alcohol Cyclization

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Solution Overview

Problem

Conventional methods for preparing sultone derivative compounds are limited, particularly in introducing chlorine or fluorine atoms, which restricts the synthesis of various sultone derivatives and results in unstable electrode passivation films for lithium-ion batteries, affecting battery performance.

Innovation Solution

A method involving the reaction of an alcohol with a sulfonyl chloride derivative followed by cyclization in the presence of a base to produce sultone derivatives, such as 1,3-propanesultone compounds, which can be used as electrolyte additives for lithium-ion batteries, enhancing the stability of the electrode passivation film.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Adaptability or versatility

If conventional substitution reaction using sultone as starting material is used, then chlorine or fluorine atoms can be introduced at specific positions, but the position for introducing atoms is limited and various sultone derivatives cannot be prepared

Engineering Contradiction:

Improvepreparation of various sultone derivativesVSAvoidlimitation in introducing chlorine or fluorine atoms

Core Design Contradiction:

Adaptability or versatilityVSDevice complexity

Solution Approach 1:

Instead of starting from sultone and attempting to introduce substituents at limited positions (conventional approach), the invention inverts the synthesis route by starting from alcohol and constructing the sultone ring with desired substituents already in place. This allows preparation of various sultone derivatives that were inaccessible through conventional substitution reactions.

Inventive Principle:

Principle #13The other way round (Inversion)

Solution Approach 2:

The invention performs preliminary actions by first establishing the carbon skeleton and introducing all necessary substituents (chlorine, fluorine, alkyl groups) at the alcohol stage before cyclization. This preliminary structuring enables the formation of diverse sultone derivatives in a single cyclization step, overcoming the positional limitations of conventional methods.

Inventive Principle:

Principle #10Preliminary action

2Reliability

If sultone compounds are used as electrolyte additives, then stable electrode passivation film can be formed, but conventional preparation methods cannot produce various derivatives needed for optimized battery performance

Engineering Contradiction:

Improvestability of electrode passivation filmVSAvoidavailability of various sultone derivatives

Core Design Contradiction:

ReliabilityVSAdaptability or versatility

Solution Approach 1:

The invention inverts the conventional approach by not relying on post-synthesis substitution of sultone, but rather by designing the precursor alcohol to yield the desired sultone derivative directly upon cyclization. This provides access to various sultone derivatives needed for optimizing battery performance while maintaining the stable passivation film formation property.

Inventive Principle:

Principle #13The other way round (Inversion)

Solution Approach 2:

The invention changes the synthetic parameters by selecting appropriate alcohol precursors with specific substituent patterns and using controlled cyclization conditions. This enables systematic variation of sultone derivative structures (different positions of chlorine, fluorine, alkyl groups) to optimize both film stability and battery performance parameters.

Inventive Principle:

Principle #35Parameter changes

3Productivity

If reaction of sultone with DAST or BAST is used to introduce fluorine atoms, then fluorinated sultone can be synthesized, but the reaction does not proceed at all

Engineering Contradiction:

Improvesynthesis of fluorinated sultoneVSAvoidreaction success

Core Design Contradiction:

ProductivityVSReliability

Solution Approach 1:

The invention performs preliminary action by introducing the fluorine atom at the alcohol stage rather than attempting to substitute hydroxyl group in sultone. The fluorinated alcohol precursor is then cyclized to give the fluorinated sultone derivative, achieving successful fluorine incorporation that was impossible through direct sultone substitution.

Inventive Principle:

Principle #10Preliminary action

Solution Approach 2:

The invention uses fluorinated alcohol as an intermediary compound that facilitates successful fluorine incorporation. Instead of directly substituting in sultone (which fails with DAST/BAST), the fluorine is introduced in the more reactive alcohol intermediate, which then cyclizes to give the desired fluorinated sultone product.

Inventive Principle:

Principle #24Intermediary (Mediator)

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 allows for the high-yield production of sultone derivatives, effectively forming a stable electrode passivation film, improving the cycle performance and energy density of lithium-ion batteries.

Implementation Method 1

reacting an alcohol with a sulfonyl chloride derivative to prepare an intermediate

Methodology Applied

Scientific EffectNucleophilic substitution: Chemical Bonding

Implementation Method 2

cyclizing the intermediate to prepare the sultone derivative

Methodology Applied

Scientific EffectCyclization reaction: Chemical Bonding

Data Source

PatentEP3587410B1Method for preparing sultone derivatives

Publication Date: 2023.08.16 SAMHWA PAINTS IND

AI summary

A method for preparing 1,3-propanesultone derivative compounds used for pharmaceutical intermediates, organic solvents, and electrolyte additives for lithium ion secondary batteries is disclosed. The method makes it is possible to prepare a sultone compound having various derivatives in high yield.