Selective Dehydrofluorination of HCFC-225ca Isomer Mixtures

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Solution Overview

Problem

The conventional method for producing 1,1-dichloro-2,3,3-tetrafluoropropene (CFO-1214ya) is complex and economically inefficient due to the need for multi-stage distillation to purify the raw material 1,1-dichloro-2,2,3,3-pentafluoropropane (HCFC-225ca) from a mixture of isomers, which have close boiling points, making separation and purification difficult.

Innovation Solution

A process involving a mixture of dichloropentafluoropropane isomers, containing 1,1-dichloro-2,2,3,3-pentafluoropropane (HCFC-225ca), is contacted with an aqueous alkali solution in the presence of a phase transfer catalyst, selectively dehydrofluorinating only the HCFC-225ca, thereby simplifying the production of CFO-1214ya without the need for raw material purification.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Manufacturing precision

If multi-stage distillation is used to purify HCFC-225ca from isomer mixture, then purification precision is improved, but device complexity and production cost increase

Engineering Contradiction:
Improvepurification precisionVSAvoiddevice complexity
Core Design Contradiction:
Manufacturing precisionVSDevice complexity

Solution Approach 1:

The invention changes the chemical parameter of the reaction system by introducing a phase transfer catalyst and using aqueous alkali solution, which enables selective dehydrofluorination of HCFC-225ca at specific reaction conditions (temperature, concentration, pH) without requiring physical separation based on boiling point differences

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The phase transfer catalyst acts as an intermediary that facilitates the reaction between aqueous alkali and organic HCFC-225ca, enabling selective transformation of the target isomer while leaving other isomers unchanged, thus avoiding the need for complex distillation equipment

Inventive Principle:
Principle #24Intermediary (Mediator)

2Manufacturing precision

If multi-stage distillation is used to purify HCFC-225ca from isomer mixture, then purification precision is improved, but productivity decreases

Engineering Contradiction:
Improvepurification precisionVSAvoidproductivity
Core Design Contradiction:
Manufacturing precisionVSProductivity

Solution Approach 1:

The reaction process performs preliminary selective transformation of HCFC-225ca to CFO-1214ya directly from the isomer mixture, eliminating the need for preliminary purification steps and enabling direct production with high productivity

Inventive Principle:
Principle #10Preliminary action

Solution Approach 2:

By controlling reaction parameters (temperature, catalyst concentration, alkali concentration), the process achieves both high selectivity for HCFC-225ca transformation and high conversion efficiency, maintaining productivity while ensuring product purity

Inventive Principle:
Principle #35Parameter changes

3Manufacturing precision

If conventional production method with raw material purification is used, then product purity is maintained, but ease of manufacture deteriorates

Engineering Contradiction:
Improveproduct purityVSAvoidease of manufacture
Core Design Contradiction:
Manufacturing precisionVSEase of manufacture

Solution Approach 1:

The phase transfer catalyst serves as an intermediary that enables selective reaction of HCFC-225ca in the presence of other isomers, simplifying the manufacturing process to a single reaction step without complex purification operations while maintaining high product purity

Inventive Principle:
Principle #24Intermediary (Mediator)

Solution Approach 2:

The invention segments the chemical reactivity of different isomers by exploiting the unique reactivity of HCFC-225ca with aqueous alkali in the presence of phase transfer catalyst, allowing selective transformation of the target isomer while leaving other isomers unaffected in the mixture

Inventive Principle:
Principle #1Segmentation

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 approach allows for the simple and economical production of CFO-1214ya, enabling the subsequent cost-effective production of 2,3,3-tetrafluoropropene (HFO-1234yf), a potential refrigerant, by eliminating the requirement for raw material purification and reducing the complexity of the production process.

Implementation Method 1

a mixture of dichloropentafluoropropane (HCFC-225) isomers which contains 1,1-dichloro-2,2,3,3,3-pentafluoropropane (HCFC-225ca) is brought into contact with an aqueous alkali solution in the presence of a phase transfer catalyst

Methodology Applied
Scientific EffectPhase transfer catalysis: Catalysis

Data Source

PatentEP2371793B1Process for production of 1,1-dichloro-2,3,3,3-tetrafluoropropene
Publication Date: 2015.07.08 AGC INC
  • EP2371793B1 patent drawing
  • EP2371793B1 patent drawing
  • EP2371793B1 patent drawing

AI summary

To provide a simple and economical process for producing 1,1-dichloro-2,3,3,3-tetrafluoropropene, which does not require purification of the raw material component obtained in the form of a mixture of isomers, and a process for producing 2,3,3,3-tetrafluoropropene from the product thereby obtained. A process for producing 1,1-dichloro-2,3,3,3-tetrafluoropropene, characterized by bringing a mixture of dichloropentafluoropropane isomers which contains 1,1-dichloro-2,2,3,3,3-pentafluoropropane into contact with an aqueous alkali solution in the presence of a phase transfer catalyst, and thereby selectively dehydrofluorinating only the 1,1-dichloro-2,2,3,3,3-pentafluoropropane in the mixture, and a process for producing 2,3,3,3-tetrafluoropropene from the 1,1-dichloro-2,3,3,3-tetrafluoropropene thereby obtained.