Fluoropropane Production via Stoichiometric HF Reaction

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Solution Overview

Problem

There is a need for efficient processes to manufacture compounds like HCFC-1233xf, HFC-245fa, HFC-245cb, HFC-1234ze, and HFC-1234yf from common halogenated hydrocarbon starting materials, where other compounds in the group can also be produced and recovered, addressing the limitations of existing methods.

Innovation Solution

A process involving the reaction of halopropane with hydrogen fluoride (HF) in the presence of a fluorination catalyst, with a stoichiometric or greater molar ratio of HF to the starting material, to produce a product mixture comprising the desired compounds, which can be recovered through subsequent steps such as dehydrofluorination and separation.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Adaptability or versatility

If fluorination of halogenated hydrocarbons is performed using conventional methods, then individual fluorinated compounds can be produced, but the process requires multiple separate reactions and catalysts for different products, increasing process complexity

Engineering Contradiction:
Improveability to produce multiple fluorinated compoundsVSAvoidprocess complexity
Core Design Contradiction:
Adaptability or versatilityVSDevice complexity

Solution Approach 1:

The patent applies universality by using a single fluorination catalyst system that can produce multiple different fluorinated compounds (HFC-245eb, HFC-1234yf, HCFC-1233xf) from the same starting material (243db) through one reaction process. The catalyst composition and reaction conditions are optimized to enable simultaneous formation of various fluorinated products, eliminating the need for separate reactions for each compound.

Inventive Principle:
Principle #6Universality (Multi-functionality)

Solution Approach 2:

The patent applies segmentation by separating the fluorination process into distinct reaction zones or stages within the reactor system. This allows different fluorinated products to be formed and collected at different stages, enabling selective recovery of individual compounds (HFC-245eb, HFC-1234yf, HCFC-1233xf) from the product mixture while maintaining a unified catalyst system.

Inventive Principle:
Principle #1Segmentation

2Productivity

If conventional fluorination processes are used, then single compounds are produced through separate reactions, but the overall productivity and efficiency are reduced due to multiple processing steps

Engineering Contradiction:
Improvemanufacturing efficiencyVSAvoidprocessing time
Core Design Contradiction:
ProductivityVSLoss of time

Solution Approach 1:

The patent merges multiple separate fluorination reactions into a single integrated process. By combining the production of HFC-245eb, HFC-1234yf, and HCFC-1233xf into one reaction system using the same catalyst and starting material, the process eliminates intermediate steps, reduces processing time, and increases overall productivity.

Inventive Principle:
Principle #5Merging (Combining)

Solution Approach 2:

The patent implements continuous fluorination where the catalyst remains active and productive throughout the entire reaction process, continuously generating multiple fluorinated compounds without requiring interruption or replacement for different product formations. This continuous operation maximizes productivity and minimizes downtime.

Inventive Principle:
Principle #20Continuity of useful action

3Quantity of substance

If multiple separate fluorination reactions are performed for different compounds, then each compound can be optimized individually, but the total amount of starting material consumed and waste produced increases

Engineering Contradiction:
Improveyield of fluorinated compoundsVSAvoidwaste from multiple reactions
Core Design Contradiction:
Quantity of substanceVSLoss of substance

Solution Approach 1:

The patent applies discarding and recovering by collecting and recovering unreacted starting material (243db) and by-products from the fluorination process. The recovered materials are recycled back into the reaction system, reducing waste and maximizing the utilization of starting material to produce the desired fluorinated compounds (HFC-245eb, HFC-1234yf, HCFC-1233xf).

Inventive Principle:
Principle #34Discarding and recovering

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 process effectively produces and recovers the target compounds with high degrees of fluorination, allowing for the production of multiple compounds from a single starting material, enhancing the efficiency and versatility of the manufacturing process.

Implementation Method 1

reacting at least one starting material which is 243db with HF in a reaction zone in the presence of a fluorination catalyst

Methodology Applied
Scientific EffectCatalysis: Catalysis

Data Source

PatentEP2091897B2Processes for the production of fluoropropanes and halopropenes
Publication Date: 2021.12.01 THE CHEMOURS CO FC LLC

AI summary

A process is disclosed for making CF3CF2CH3, CF3CF=CH2 and/or CF3CCI=CH2. The process involves reacting at least one starting material selected from the group consisting of halopropanes of the formula CX3CHCICH2X, halopropenes of the formula CCIX2CCI=CH2 and halopropenes of the formula CX2=CCICH2X, wherein each X is independently F or Cl, with HF in a reaction zone to produce a product mixture comprising HF, HCI, CF3CF2CH3, CF3CF=CH2 and CFsCCI=CH2; and recovering the CF3CF2CH3, CF3CF=CH2 and/or CFsCCI=CH2 from the product mixture. Also disclosed is a process for making CF3CH2CHF2, CFsCH=CHF and/or CF3CH=CHCI. This process involves reacting at least one starting material selected from the group consisting of halopropanes of the formula CX3CHCICH2X, halopropenes of the formula CX3CCI=CH2 and halopropenes of the formula CX2=CCICH2X, wherein each X is independently F or Cl, with HF in a reaction zone to produce a product mixture comprising HF, HCI, CF3CH2CHF2, CF3CH=CHF and CF3CH=CHCI; and recovering the CF3CH2CHF2, CF3CH=CHF and/or CF3CH=CHCI from the product mixture. Also disclosed is a process for making CF3CF2CH3 and/or CF3CF=CH2- This process involves reacting at least one starting material selected from the group consisting of halopropanes of the formula CX3CHCICH2X, halopropenes of the formula CX3CCI=CH2 and halopropenes of the formula CX2=CCICH2X, wherein each X is independently F or Cl, with HF in a reaction zone to produce a product mixture comprising HF, HCI, CF3CF2CH3 and CF3CF=CH2; and recovering the CF3CF2CH3 and/or CF3CF=CH2 from the product mixture. In each of the processes the molar ratio of HF to total amount of starting material fed to the reaction zone is at least stoichiometric. Also disclosed is an azeotropic composition comprising CF3CCI=CH2, and HF. Also disclosed is an azeotropic composition comprising CF3CF2CH3, and HF.