Substituted 2-Fluoroacrylic Acid Synthesis via Base Elimination

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Solution Overview

Problem

Existing processes for preparing substituted 2-fluoroacrylic acid derivatives suffer from low yields and are not economically or safely viable for industrial use, due to the unavailability of starting materials and inefficient reaction pathways.

Innovation Solution

A process involving the conversion of substituted 3-halo-2-fluoropropionic acid derivatives into 2-fluoroacrylic acid derivatives in the presence of bases and polymerization inhibitors, which enhances yields and purity, making it suitable for industrial applications.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Productivity

If existing processes for preparing substituted 2-fluoroacrylic acid derivatives are used, then the preparation can be performed, but the reaction yields are low and the processes are not economically viable

Engineering Contradiction:

Improvereaction yieldVSAvoideconomic viability

Core Design Contradiction:

ProductivityVSEase of manufacture

Solution Approach 1:

The patent changes the reaction parameters by using a specific base (alkali metal hydroxide, alkali metal carbonate, or alkali metal bicarbonate) in a controlled molar ratio (0.5-2.0 equivalents) and conducting the reaction at elevated temperatures (80-150°C) to optimize the elimination reaction conditions, thereby achieving high yields (85-95%) and improving economic viability

Inventive Principle:

Principle #35Parameter changes

Solution Approach 2:

The patent uses an intermediary compound, substituted 3-halo-2-fluoropropionic acid derivatives, as a readily available starting material that facilitates the synthesis of substituted 2-fluoroacrylic acid derivatives through a straightforward elimination reaction, improving both yield and economic feasibility

Inventive Principle:

Principle #24Intermediary (Mediator)

2Ease of manufacture

If existing processes are used, then preparation can proceed, but the starting materials are not readily available

Engineering Contradiction:

Improveavailability of starting materialsVSAvoidreaction yield

Core Design Contradiction:

Ease of manufactureVSProductivity

Solution Approach 1:

The patent identifies substituted 3-halo-2-fluoropropionic acid derivatives as readily available intermediary compounds that serve as excellent starting materials for the elimination reaction, ensuring both ease of manufacture and high reaction yields (85-95%)

Inventive Principle:

Principle #24Intermediary (Mediator)

3Reliability

If existing processes are used, then preparation can be attempted, but safety issues arise due to hazardous chemicals required

Engineering Contradiction:

ImprovesafetyVSAvoidreaction yield

Core Design Contradiction:

ReliabilityVSProductivity

Solution Approach 1:

The patent converts a potentially harmful process into a safe and efficient one by using mild base-catalyzed elimination conditions that avoid hazardous reagents while achieving high yields (85-95%), thereby improving both safety and productivity simultaneously

Inventive Principle:

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

Solution Approach 2:

The patent creates a safe reaction environment by using inert or mild reagents (common bases like NaOH, KOH, Na2CO3, KHCO3) that do not require specialized handling, eliminating safety hazards while maintaining high reaction efficiency and yields

Inventive Principle:

Principle #39Inert atmosphere (Inert environment)

4Productivity

If existing processes are used, then preparation can proceed, but the processes cannot be used in industrial processes for economic reasons

Engineering Contradiction:

Improveindustrial suitabilityVSAvoideconomic feasibility

Core Design Contradiction:

ProductivityVSEase of manufacture

Solution Approach 1:

The patent optimizes reaction parameters for industrial scalability by using readily available starting materials, common bases, and moderate temperatures (80-150°C), achieving high yields (85-95%) that make the process economically feasible for industrial production

Inventive Principle:

Principle #35Parameter changes

Solution Approach 2:

The patent employs readily available substituted 3-halo-2-fluoropropionic acid derivatives as intermediaries that simplify the industrial manufacturing process, reducing costs and improving economic feasibility while maintaining high productivity

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 process achieves high yields and high purity of 2-fluoroacrylic acid derivatives, making them suitable for industrial production and use in plastics and medicament additives, without the need for hazardous chemicals or specialized handling.

Implementation Method 1

substituted 3-halo-2-fluoropropionic acid derivatives are converted, in the presence of bases, to substituted 2-fluoroarylic acid derivatives

Methodology Applied

Scientific EffectElimination reaction: Chemical Bonding

Data Source

PatentUS9000210B2Preparation of substituted 2-fluoroacrylic acid derivatives

Publication Date: 2015.04.07 SALTIGO GMBH

AI summary

The present invention relates to a process for the preparation of substituted 2-fluoroacrylic acid derivatives.