HCFO E-to-Z Isomerization for High-Purity 1224yd Production

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Solution Overview

Problem

Existing methods for producing (Z)-1-chloro-2,3,3,3-tetrafluoropropene (HCFO-1224yd) and (Z)-1,2-dichloro-3,3,3-trifluoropropene (HCFO-1223xd) result in mixtures of E- and Z-isomers, necessitating an industrially advantageous and efficient method for selective production of one isomer and minimizing by-product formation.

Innovation Solution

An isomerization reaction is employed to convert the E-isomer of HCFO-1224yd or HCFO-1223xd into their respective Z-isomers, utilizing a metal catalyst or radical generator under specific conditions to achieve high conversion rates while inhibiting by-product production.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Productivity

If conventional dehydrochlorination or dehydrofluorination methods are used to produce HCFO-1224yd, then production efficiency is achieved, but the product is obtained as a mixture of E-isomer and Z-isomer which is inconvenient for selective use

Engineering Contradiction:
Improveproduction efficiencyVSAvoidisomer selectivity
Core Design Contradiction:
ProductivityVSManufacturing precision

Solution Approach 1:

The invention changes the reaction parameters by using specific base catalysts (alkali metal hydroxides or alkaline earth metal hydroxides) and controlling the reaction temperature (50-100°C) and time (0.5-2 hours) to achieve selective production of Z-isomer HCFO-1224yd with 90% or higher purity, resolving the contradiction between productivity and isomer selectivity

Inventive Principle:
Principle #35Parameter changes

2Productivity

If hydrogen reduction is performed on HCFO-1224yd mixture to produce HFO-1234yf, then the target product is obtained, but by-products are generated and additional separation steps are required

Engineering Contradiction:
ImproveHFO-1234yf productionVSAvoidby-product formation
Core Design Contradiction:
ProductivityVSObject-generated harmful factors

Solution Approach 1:

The invention performs preliminary action by first selectively producing pure Z-isomer HCFO-1224yd through dehydrofluorination before hydrogen reduction. This preliminary purification step ensures that the subsequent hydrogen reduction reaction produces HFO-1234yf with minimal by-products, eliminating the need for complex separation steps

Inventive Principle:
Principle #10Preliminary action

3Manufacturing precision

If separation processes are applied to separate E-isomer and Z-isomer, then pure Z-isomer can be obtained, but the process complexity and cost increase

Engineering Contradiction:
Improveisomer purityVSAvoidseparation process complexity
Core Design Contradiction:
Manufacturing precisionVSDevice complexity

Solution Approach 1:

The invention performs preliminary action by designing a reaction system that directly produces pure Z-isomer HCFO-1224yd through selective dehydrofluorination, eliminating the need for subsequent separation processes. This approach achieves high isomer purity (90% or higher) while keeping the process simple and cost-effective

Inventive Principle:
Principle #10Preliminary action

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 efficiently produces the desired Z-isomer with reduced by-products, allowing for high-purity separation through distillation, thereby enhancing industrial efficiency and product purity.

Implementation Method 1

utilizing a metal catalyst or radical generator under specific conditions to achieve high conversion rates

Methodology Applied
Scientific EffectCatalysis: Catalysis

Implementation Method 2

utilizing a metal catalyst or radical generator under specific conditions to achieve high conversion rates

Methodology Applied
Scientific EffectRadical reaction:

Implementation Method 3

allowing for high-purity separation through distillation

Methodology Applied
Scientific EffectDistillation: Distillation

Data Source

PatentEP3318548B1Hydrochlorofluoroolefin production method and 2,3,3,3-tetrafluoropropene production method
Publication Date: 2025.12.10 AGC INC
  • EP3318548B1 patent drawing
  • EP3318548B1 patent drawing
  • EP3318548B1 patent drawing

AI summary

There is provided an industrially advantageous and efficient method of producing a Z-isomer of HCFO-1224yd or HCFO-1223xd by isomerizing an E-isomer thereof. The method produces HCFO (Z-isomer) by causing specific HCFO (E-isomer) contained in a raw material composition to undergo an isomerization reaction under a condition where the HCFO (E-isomer) is isomerized.