Catalyst-Free Gas-Phase Fluorination of Chloropropane

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Solution Overview

Problem

Current processes for preparing 2-chloro-3,3,3-trifluoropropene (HCFC-1233xf) suffer from low yield, high catalyst costs, and unsatisfactory selectivity, making them unsuitable for industrial-scale production.

Innovation Solution

A process involving a reaction between a chloropropane or chloropropene compound and hydrogen fluoride in the gas phase without a catalyst at elevated temperatures, using specific chlorine-containing compounds as starting materials, to achieve high yield and selectivity in a single step.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Speed

If a catalyst is used for fluorination of 1,1,2,3-tetrachloropropene, then the reaction rate increases, but the cost increases and selectivity decreases

Engineering Contradiction:
Improvereaction rateVSAvoidcost
Core Design Contradiction:
SpeedVSEase of manufacture

Solution Approach 1:

The patent removes the catalyst from the reaction system entirely. Instead of using a chromium-based catalyst that increases cost and reduces selectivity, the invention uses a catalyst-free approach with specific chlorine-containing compounds as starting materials, achieving high yield and selectivity without catalyst costs

Inventive Principle:
Principle #2Taking out (Extraction)

Solution Approach 2:

The patent changes the reaction parameters by using specific chlorine-containing compounds (formulae 1, 2, or 3) as starting materials instead of conventional 1,1,2,3-tetrachloropropene. This parameter change in the starting material structure enables the reaction to proceed without catalyst while maintaining high reaction efficiency and selectivity

Inventive Principle:
Principle #35Parameter changes

2Speed

If a catalyst is used for fluorination, then the reaction rate increases, but the yield decreases due to multiple products

Engineering Contradiction:
Improvereaction rateVSAvoidyield
Core Design Contradiction:
SpeedVSProductivity

Solution Approach 1:

The patent eliminates the catalyst that causes unwanted side reactions. By using a catalyst-free system with specific starting materials, the reaction achieves high selectivity for the target product HCFC-1233xf, avoiding the formation of multiple by-products that occur with catalytic processes

Inventive Principle:
Principle #2Taking out (Extraction)

Solution Approach 2:

The invention changes the chemical parameters by selecting specific chlorine-containing compounds with particular structures (formulae 1, 2, or 3) as starting materials. This structural parameter change ensures that the fluorination reaction proceeds selectively to form only the desired HCFC-1233xf product, achieving both high yield and high selectivity simultaneously

Inventive Principle:
Principle #35Parameter changes

3Reliability

If conventional fluorination process is used, then the process is established, but the reaction time is long and conditions are severe

Engineering Contradiction:
Improveprocess stabilityVSAvoidreaction time
Core Design Contradiction:
ReliabilityVSLoss of time

Solution Approach 1:

The patent optimizes reaction parameters by using specific starting materials (formulae 1, 2, or 3) that react rapidly with hydrogen fluoride. This parameter change in the starting material structure enables the reaction to proceed under mild conditions with short reaction time, while maintaining process stability through controlled reaction conditions

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 enables efficient and economical production of HCFC-1233xf with high yield and selectivity, suitable for industrial-scale production, eliminating the drawbacks of previous processes.

Implementation Method 1

subjecting, in the absence of a catalyst, at least one chlorine-containing compound selected from the group consisting of chloropropane represented by formula (1), chloropropene represented by formula (2), and chloropropene represented by formula (3), to a reaction with hydrogen fluoride

Methodology Applied
Scientific EffectChemical Bonding: Chemical Bonding

Data Source

PatentEP2421810B1Process for preparing 2-chloro-3,3,3-trifluoropropene
Publication Date: 2015.06.03 DAIKIN INDUSTRIES LTD
  • EP2421810B1 patent drawingFigure 1
  • EP2421810B1 patent drawingFigure 2

AI summary

The present invention provides a process for preparing 2-chloro-3,3,3-trifluoropropene including subjecting, in the absence of a catalyst, at least one chlorine-containing compound selected from the group consisting of chloropropane represented by formula (1): CClX2CHClCH2Cl, wherein each X is the same or different and each represents Cl or F, chloropropene represented by formula (2): CClY2CCl=CH2, wherein each Y is the same or different and each represents Cl or F, and chloropropene represented by formula (3): CZ2=CClCH2Cl, wherein each Z is the same or different and each represents Cl or F, to a reaction with hydrogen fluoride under heating in a gas phase. According to the present invention, 2-chloro-3,3,3-trifluoropropene (HCFC-1233xf) can be effectively prepared by an easy and economically advantageous process that is suitable for industrial scale production.