Low-Temperature Dephosphorization for High-Purity Olefin Production

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Solution Overview

Problem

Existing methods for producing (E)-1,2-difluoroethylene (R1132(E)) result in impurities such as cis- and trans-1H-nonafluoro-2-propoxyethene, which affect the purity of the target compound.

Innovation Solution

Reacting specific phosphorus-containing olefin compound salts (such as those represented by formulas (1) to (4)) with a base at a temperature of 50° C. or less to produce a dephosphorized and hydrogenated olefin compound with high purity.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Manufacturing precision

If conventional methods are used to produce (E)-1,2-difluoroethylene, then the reaction proceeds at higher temperatures with faster kinetics, but impurities such as cis- and trans-1H-nonafluoro-2-propoxyethene are generated reducing product purity

Engineering Contradiction:
Improvepurity of (E)-1,2-difluoroethyleneVSAvoidby-product formation
Core Design Contradiction:
Manufacturing precisionVSObject-generated harmful factors

Solution Approach 1:

The patent applies parameter changes by strictly controlling the reaction temperature at 50°C or below during the reaction between phosphorus-containing olefin compound salt and base. This temperature parameter control suppresses side reactions that generate impurities like cis- and trans-1H-nonafluoro-2-propoxyethene, while still allowing the main reaction to proceed efficiently, thereby achieving high purity (E)-1,2-difluoroethylene

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent employs preliminary action by pre-selecting and using specific phosphorus-containing olefin compound salts (formulas 1-4) with defined structural characteristics before the reaction occurs. These pre-chosen substrates with specific phosphorus protecting groups and fluoroalkyl configurations are designed to react selectively at low temperatures, preventing impurity formation before it can occur

Inventive Principle:
Principle #10Preliminary action

2Manufacturing precision

If the reaction temperature is maintained at 50°C or less, then by-product formation is suppressed and product purity increases, but the reaction rate may decrease

Engineering Contradiction:
Improvepurity of olefin compoundVSAvoidreaction rate
Core Design Contradiction:
Manufacturing precisionVSProductivity

Solution Approach 1:

The patent resolves this contradiction through parameter changes by optimizing the temperature parameter to exactly 50°C or below, which is the critical threshold where the reaction maintains acceptable rate while suppressing by-product formation. Additionally, the choice of specific phosphorus-containing substrates and bases creates a reactive system that proceeds efficiently even at this constrained temperature

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The phosphorus-containing olefin compound salt acts as an intermediary that enables the reaction to proceed at low temperatures. The phosphorus protecting group serves as a leaving group that facilitates the elimination reaction at 50°C or below, allowing the main reaction to occur at this favorable temperature without requiring higher temperatures that would generate impurities

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 effectively suppresses the production of by-products like trifluoroethylene and pentafluoroethane, thereby increasing the purity of (E)-1,2-difluoroethylene (R1132(E)) to high levels.

Implementation Method 1

reacting at least one phosphorus-containing olefin compound salt with a base, thereby obtaining a dephosphorized and hydrogenated olefin compound

Methodology Applied
Scientific EffectChemical reaction: Chemical Bonding

Data Source

PatentUS12275681B2Olefin compound production method
Publication Date: 2025.04.15 DAIKIN INDUSTRIES LTD
  • US12275681B2 patent drawing
  • US12275681B2 patent drawing
  • US12275681B2 patent drawing

AI summary

Provided is a method for producing an olefin compound using reaction with a base, whereby a target product with a higher purity than the prior art can be obtained. Specifically, provided is a method for producing an olefin compound by reacting a phosphorus-containing olefin compound salt with a base to obtain a dephosphorized and hydrogenated olefin compound, wherein the temperature of the reaction is 50° C. or less.