Fluoroolefin Production via Low-Temperature Liquid Phase Dehydrofluorination

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Solution Overview

Problem

Existing methods for producing fluoroolefins of the formula CX1=X2=CX3=X4, where X1-X4 are H or F, lack high selectivity.

Innovation Solution

Performing dehydrofluorination of a fluorocarbon of the formula CX1FCX3X4H with a base in the liquid phase at a temperature of -70°C to 30°C.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Manufacturing precision

If dehydrofluorination is performed using existing methods (gas phase or with metal catalysts), then production can proceed, but selectivity for the target fluoroolefin is low

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

Solution Approach 1:

The patent changes the reaction parameters by conducting dehydrofluorination in the liquid phase at low temperatures (-70°C to 30°C) using a base catalyst, rather than gas phase or high-temperature processes. This parameter change achieves high selectivity for the target fluoroolefin while maintaining process feasibility

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent introduces a base (such as alkali metal hydroxides, carbonates, or alkoxides) as an intermediary catalyst to facilitate the dehydrofluorination reaction. This base mediator enables high-selectivity production of fluoroolefins from fluorocarbon substrates under mild conditions

Inventive Principle:
Principle #24Intermediary (Mediator)

2Productivity

If reaction temperature is increased to improve reaction rate, then productivity increases, but selectivity decreases

Engineering Contradiction:
Improvereaction rateVSAvoidselectivity
Core Design Contradiction:
ProductivityVSManufacturing precision

Solution Approach 1:

The patent identifies and exploits an optimal temperature window (-70°C to 30°C) where the reaction rate is sufficiently high for practical productivity while selectivity is maximized. This counterintuitive low-temperature approach resolves the typical trade-off between rate and selectivity

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent creates locally optimal conditions by using a base catalyst that specifically promotes the desired dehydrofluorination pathway at low temperatures, rather than relying on high temperature to drive the reaction. The base provides localized catalytic activity that maintains both rate and selectivity

Inventive Principle:
Principle #3Local quality

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

Achieves high conversion and selectivity in producing fluoroolefins, with the target compounds being obtained with high yield and purity.

Implementation Method 1

dehydrofluorination of a fluorocarbon of the formula CX1FCX3X4H with a base in the liquid phase

Methodology Applied
Scientific EffectDehydrofluorination:

Data Source

PatentEP3778539B1Fluoroolefin production method
Publication Date: 2023.09.27 DAIKIN INDUSTRIES LTD
  • EP3778539B1 patent drawing

AI summary

The present disclosure provides a method for producing fluoroolefin represented by formula (1): CX1X2=CX3X4, wherein X1, X2, X3, and X4 are the same or different, and represent a hydrogen atom or a fluorine atom, with high selectivity. Specifically, the present disclosure is a method for producing fluoroolefin represented by formula (1), wherein the method includes the step of performing dehydrofluorination by bringing a fluorocarbon represented by formula (2) : CX1X2FCX3X4H, wherein X1, X2, X3, and X4 are as defined above, into contact with a base, and the dehydrofluorination step is performed in the liquid phase at a temperature of -70°C or higher to less than 120°C.