Fluorination of 1-chloro-2,2-difluoroethane for HFO-1132

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Solution Overview

Problem

Existing methods for preparing 1,2-difluoroethylene (HFO-1132) and/or 1,1,2-trifluoroethane (HFC-143) face challenges in achieving high conversion and selectivity.

Innovation Solution

A method involving a fluorination reaction between 1-chloro-2,2-difluoroethane and hydrogen fluoride to produce 1,1,2-trifluoroethane, which can then be further processed to obtain HFO-1132 with high conversion and selectivity.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Manufacturing precision

If conventional hydrodechlorination reaction is used to prepare HFO-1132, then the process can proceed with existing catalysts, but the conversion and selectivity are insufficient

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

Solution Approach 1:

The patent changes the chemical reaction parameters by replacing the hydrodechlorination reaction with a fluorination reaction using HF as the reagent. This fundamental parameter change transforms the reaction mechanism to achieve superior selectivity for HFO-1132 while maintaining industrial feasibility through established fluorination technology

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent introduces specific catalysts as intermediaries to mediate the fluorination reaction between 1,2-dichloro-1,2-difluoroethylene and HF. These catalysts facilitate the selective formation of HFO-1132 by controlling the reaction pathway, thereby achieving high selectivity without requiring complex multi-step processes

Inventive Principle:
Principle #24Intermediary (Mediator)

2Productivity

If homocoupling reaction of CH2F2 and CH2ClF is used, then the reaction conditions can be simplified, but the conversion rate remains low

Engineering Contradiction:
ImproveconversionVSAvoidselectivity
Core Design Contradiction:
ProductivityVSManufacturing precision

Solution Approach 1:

The patent fundamentally changes the reaction parameters by employing fluorination with HF instead of homocoupling reactions. This parameter transformation enables simultaneous achievement of high conversion rates and high selectivity for HFO-1132, resolving the trade-off between productivity and manufacturing precision

Inventive Principle:
Principle #35Parameter changes

3Ease of manufacture

If existing HFC conversion methods are applied, then the process can utilize available technology, but the selectivity for desired products is not high enough

Engineering Contradiction:
Improvetechnology availabilityVSAvoidselectivity
Core Design Contradiction:
Ease of manufactureVSManufacturing precision

Solution Approach 1:

The patent employs specific catalysts as intermediaries in the fluorination process to achieve high selectivity for HFO-1132 and HFC-143. These catalysts enable the reaction to proceed selectively while maintaining ease of manufacture through continuous flow processing and readily available reagents

Inventive Principle:
Principle #24Intermediary (Mediator)

Solution Approach 2:

The patent applies fluorination reaction parameters using HF and controlled temperature conditions to transform the existing HFC conversion technology into a high-selectivity process. This parameter optimization maintains technological simplicity while dramatically improving product selectivity

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

The method achieves high conversion and selectivity for HFO-1132 and HFC-143, making the process more efficient and industrially viable.

Implementation Method 1

a step of performing a fluorination reaction by contacting 1-chloro-2,2-difluoroethane with HF to obtain 1,1,2-trifluoroethane

Methodology Applied
Scientific EffectFluorination reaction: Chemical Bonding

Data Source

PatentEP3792236B1Method for preparing 1,2-difluoroethylene and/or 1,1,2-trifluoroethane
Publication Date: 2025.05.28 DAIKIN INDUSTRIES LTD

AI summary

This invention relates to a method for preparing 1,2-difluoroethylene and/or 1,1,2-trifluoroethane, comprising a step of performing at least one fluorination reaction by bringing at least one halide selected from the group consisting of haloethanes represented by general formula (1) CHX1X2CH2X3 (wherein X1, X2, and X3 are the same or different, and represent Cl, Br, or F) and haloethylenes represented by general formula (2) CHX4=CHX5 (wherein X4 and X5 are the same or different, and represent Cl, Br or F, with the proviso that the case in which X4 and X5 are both F is excluded).