2-Fluoroacrylate Synthesis via Cyclopropane Intermediates

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Solution Overview

Problem

Current methods for producing 2-fluoroacrylates are costly, environmentally unfriendly, and have low atom utilization economy, with high toxicity and expensive reagents, making them inefficient and unsustainable.

Innovation Solution

A method involving the reaction of vinyl ethers with dichloromonofluoromethane to form substituted cyclopropane compounds, followed by hydrolysis and oxidation to produce 2-fluoroacrylates, using mild conditions and readily available materials, with phase transfer catalysts and specific temperature controls to enhance selectivity and purity.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Ease of manufacture

If conventional methods (reaction of 2-fluoroacetate with formaldehyde followed by dehydration) are used, then 2-fluoroacrylates can be produced, but the process requires cryogenic control and expensive alkali reagents, increasing cost and environmental harm

Engineering Contradiction:

Improvemanufacturing costVSAvoidenvironmental friendliness

Core Design Contradiction:

Ease of manufactureVSObject-affected harmful factors

Solution Approach 1:

The invention changes the reaction parameters by using vinyl ether and dichloromonofluoromethane as starting materials instead of 2-fluoroacetate and formaldehyde, eliminating the need for cryogenic control and expensive alkali reagents while maintaining product formation

Inventive Principle:

Principle #35Parameter changes

Solution Approach 2:

The invention replaces expensive reagents (alkali reagents, NBS, DBU) with cheaper, more environmentally friendly alternatives, reducing both cost and environmental harm in the process

Inventive Principle:

Principle #27Cheap short-living objects (Disposable)

2Ease of manufacture

If synthesis from 2-chloropropionate via fluorination, NBS bromination and elimination is used, then 2-fluoroacrylates can be produced, but stoichiometric NBS and DBU are required, increasing cost and environmental harm

Engineering Contradiction:

Improvemanufacturing costVSAvoidenvironmental friendliness

Core Design Contradiction:

Ease of manufactureVSObject-generated harmful factors

Solution Approach 1:

The invention eliminates the need for stoichiometric NBS and DBU by using a different synthetic route involving vinyl ether and dichloromonofluoromethane, replacing expensive and environmentally harmful reagents with cheaper, more eco-friendly alternatives

Inventive Principle:

Principle #27Cheap short-living objects (Disposable)

Solution Approach 2:

The invention converts a harmful multi-step process requiring stoichiometric reagents into a more efficient one-step reaction that is both cost-effective and environmentally friendly, turning a harmful process into a beneficial one

Inventive Principle:

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

3Ease of manufacture

If synthesis from 2-fluoromalonate via addition with formaldehyde under basic condition is used, then 2-fluoroacrylates can be produced, but raw material cost is high and atom utilization economy is low

Engineering Contradiction:

Improveraw material costVSAvoidatom utilization economy

Core Design Contradiction:

Ease of manufactureVSLoss of substance

Solution Approach 1:

The invention changes the starting materials from 2-fluoromalonate and formaldehyde to vinyl ether and dichloromonofluoromethane, improving atom utilization economy by reducing waste and lowering raw material costs

Inventive Principle:

Principle #35Parameter changes

Solution Approach 2:

The invention improves atom utilization by designing a process that minimizes waste and maximizes the incorporation of starting materials into the final product, reducing the need to discard valuable atoms and reducing raw material requirements

Inventive Principle:

Principle #34Discarding and recovering

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 improves the environmental friendliness, product selectivity, and cost-effectiveness of 2-fluoroacrylate production, ensuring high-quality end products through effective quality control of intermediates and reducing the need for expensive reagents.

Implementation Method 1

the addition reaction upon mixing in step (1) includes a phase transfer catalyst

Methodology Applied

Scientific EffectPhase transfer catalysis: Catalysis

Implementation Method 2

the oxidization in step (3) utilizes an oxidizing agent selected from the group consisting of sodium chlorite, sodium hypochlorite, 30% hydrogen peroxide, peracetic acid, peroxybenzoic acid, m-chloroperoxybenzoic acid, sodium persulfate, t-butanol peroxide, oxygen, and air

Methodology Applied

Scientific EffectOxidation: Oxidation

Data Source

PatentEP3647304B1Method for preparing 2-fluoroacrylate

Publication Date: 2021.11.03 LINHAI TIANYU PHARMA

AI summary

Disclosed is a method for preparing a 2-fluoroacrylate, comprising the steps of: (1) mixing a vinyl ether having the structure of formula A with dichloromonofluoromethane to yield a substituted cyclopropane compound having the structure of formula B; (2) mixing the substituted cyclopropane compound having the structure of formula B with R2OH to yield an acetal product having the structure of formula C, followed by hydrolysis to yield 2-fluoroacrylaldehyde having the structure of formula D; or reacting the substituted cyclopropane compound having the structure of formula B with water to yield 2-fluoroacrylaldehyde having the structure of formula D via hydrolysis; (3) oxidizing 2-fluoroacrylaldehyde having the structure of formula D to yield 2-fluoroacrylic acid having the structure of formula E; and (4) mixing 2-fluoroacrylic acid having the structure of formula E with R3OH to yield a 2-fluoroacrylate having the structure of formula F.