Alpha-Fluoroacrylate Ester Purification via Distillation Inversion

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Solution Overview

Problem

Existing methods for producing α-fluoroacrylate ester result in low-purity products with poor preservation stability and high susceptibility to polymerization, leading to inefficient production and unstable storage.

Innovation Solution

A method involving the purification of a fluorocyclopropane derivative through distillation and washing with an aqueous alkali solution, followed by thermal decomposition, to produce highly-pure α-fluoroacrylate ester, which is then stored under specific conditions to maintain stability and polymerizability.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Ease of manufacture

If the reaction product is purified by washing with aqueous potassium hydroxide solution first and then distilling, then the purification process is simpler, but the product purity is low and the compound decomposes during processing

Engineering Contradiction:

Improvepurification process simplicityVSAvoidproduct purity

Core Design Contradiction:

Ease of manufactureVSManufacturing precision

Solution Approach 1:

The patent inverts the conventional purification sequence by performing distillation first to separate the fluorocyclopropane derivative from the reaction mixture, then washing the distillate with aqueous alkali solution. This reversal prevents decomposition that occurs when washing is performed first on the crude reaction product, thereby achieving high purity while maintaining process simplicity.

Inventive Principle:

Principle #13The other way round (Inversion)

2Productivity

If the fluorocyclopropane derivative is not highly purified, then the production process is faster, but the α-fluoroacrylate ester has low preservation stability and polymerizes easily

Engineering Contradiction:

Improveproduction speedVSAvoidpreservation stability

Core Design Contradiction:

ProductivityVSReliability

Solution Approach 1:

The patent applies preliminary action by performing thorough purification of the fluorocyclopropane derivative through distillation followed by alkali washing before the thermal decomposition step. This preliminary purification removes impurities that would otherwise cause polymerization and degradation during storage, ensuring long-term stability of the final product without compromising production efficiency.

Inventive Principle:

Principle #10Preliminary action

3Adaptability or versatility

If the purification order is reversed (washing then distilling), then the process follows conventional methods, but highly-pure product cannot be obtained efficiently

Engineering Contradiction:

Improvemethod conventionalnessVSAvoidproduct purity

Core Design Contradiction:

Adaptability or versatilityVSManufacturing precision

Solution Approach 1:

The patent deliberately inverts the conventional purification sequence (washing then distilling) to achieve superior product purity. By distilling first to obtain the pure fluorocyclopropane derivative and then washing the distillate, the method overcomes the limitations of conventional approaches and efficiently produces highly-pure α-fluoroacrylate ester suitable for optical materials and semiconductor resists.

Inventive Principle:

Principle #13The other way round (Inversion)

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 method achieves high-purity α-fluoroacrylate ester production, enhancing its polymerizability and storage stability, allowing for the creation of polymers with superior properties for optical, paint, and semiconductor resist applications.

Implementation Method 1

subjecting the purified product to a thermal decomposition reaction to give a compound represented by the following formula (F)

Methodology Applied

Scientific EffectThermal decomposition: Thermolysis

Implementation Method 2

purification treatment in the order of distillation and washing

Methodology Applied

Scientific EffectDistillation: Distillation

Implementation Method 3

washing with an aqueous alkali solution

Methodology Applied

Scientific EffectWashing:

Data Source

PatentEP3434665B1Method for producing a-fluoro acrylic acid ester, and composition containing highly-pure fluorocyclopropane derivative, and composition containing highly-pure a-fluoro acrylic acid ester

Publication Date: 2021.09.15 AGC INC

AI summary

The present invention provides a production method of α-fluoroacrylate ester, a composition containing a highly-pure fluorocyclopropane derivative and a composition containing highly-pure α-fluoroacrylate ester. The present invention relates to a method of producing a compound represented by the following formula (F), including subjecting a composition containing a compound represented by the following formula (A) to a purification treatment in the order of distillation and washing with an aqueous alkali solution to give a purified product containing a compound represented by the following formula (A), and subjecting the purified product to a thermal decomposition reaction, a composition containing a highly-pure compound represented by the following formula (A), and a composition containing a highly-pure compound represented by the following formula (F), wherein R may be the same or different and is a monovalent hydrocarbon group, and X is a halogen atom: