Selective 1224 Production via Phase Transfer Catalysis

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Solution Overview

Problem

Existing methods for producing 2-chloro-1,3,3,3-tetrafluoropropene (1224) result in significant by-production of 1,2-dichloro-3,3-trifluoropropene (1223), making it difficult to efficiently obtain pure 1224.

Innovation Solution

Contacting 2,3-dichloro-1,1,1,3-tetrafluoropropane (234da) with an inorganic base in an aqueous medium in the presence of a phase transfer catalyst, specifically a quaternary ammonium salt, to suppress the formation of 1223 and enhance the selectivity of 1224 production.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Manufacturing precision

If existing methods are used to produce 2-chloro-1,3,3,3-tetrafluoropropene (1224), then the production process can proceed, but significant by-production of 1,2-dichloro-3,3-trifluoropropene (1223) occurs, reducing manufacturing precision and product purity

Engineering Contradiction:
Improveselectivity of 1224 productionVSAvoidby-production of 1223
Core Design Contradiction:
Manufacturing precisionVSObject-generated harmful factors

Solution Approach 1:

The patent changes the reaction parameters by introducing a phase transfer catalyst and using an inorganic base in an aqueous medium, which fundamentally alters the reaction pathway to suppress by-product formation and enhance selectivity for 1224

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

A phase transfer catalyst is introduced as an intermediary substance to facilitate the reaction between 2,3-dichloro-1,1,1,3-tetrafluoropropane and the inorganic base, enabling selective dehydrochlorination while preventing unwanted side reactions that produce 1223

Inventive Principle:
Principle #24Intermediary (Mediator)

2Productivity

If conventional synthesis methods are employed, then the reaction can proceed, but the yield and purity of 1224 are reduced due to significant by-product formation

Engineering Contradiction:
Improveyield of 1224VSAvoidpurity of 1224
Core Design Contradiction:
ProductivityVSManufacturing precision

Solution Approach 1:

By changing the reaction medium to an aqueous system with inorganic base and adding a phase transfer catalyst, the reaction parameters are optimized to simultaneously increase both the yield and purity of 1224, eliminating the trade-off between productivity and manufacturing precision

Inventive Principle:
Principle #35Parameter changes

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 reduces the generation of 1223 as a by-product, allowing for high-yield, selective production of 1224, improving the efficiency and purity of the desired product.

Implementation Method 1

bringing 2,3-dichloro-1,1,1,3-tetrafluoropropane (234da) into contact with an inorganic base having a pKa of 4.8 or greater in an aqueous medium in the presence of a phase transfer catalyst

Methodology Applied
Scientific EffectPhase transfer catalysis: Catalysis

Data Source

PatentUS9533926B2Method for producing 2-chloro-1,3,3,3-tetrafluoropropene
Publication Date: 2017.01.03 CENT GLASS CO LTD
  • US9533926B2 patent drawing

AI summary

A production method of 2-chloro-1,3,3,3-tetrafluoropropene (1224) according to the present invention includes bringing 2,3-dichloro-1,1,1,3-tetrafluoropropane (234da) into contact with an inorganic base having a pKa of 4.8 or greater in an aqueous medium in the presence of a phase transfer catalyst. Preferably, the inorganic base has a pKa of 10 or greater. Further, the phase transfer catalyst is preferably at least one selected from the group consisting of tetrabutylammonium bromide, methyltri-n-octylammonium chloride, benzyltrimethylammonium chloride and tetraethylammonium chloride. It is possible by this method to selectively produce 1224 from 234da.