Halopropene Fluorination Process for Refrigerant Production

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Solution Overview

Problem

There is a need for efficient processes to manufacture compounds such as 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 for refrigerants and intermediates.

Innovation Solution

A process involving the reaction of halopropanes or halopropenes with hydrogen fluoride (HF) and chlorine (Cl2) in a reaction zone, optionally with a chlorofluorination catalyst, to produce a product mixture comprising HF, HCl, and specific fluorinated compounds, with stoichiometric ratios of HF to starting material and Cl2 to starting material, allowing for the recovery of desired products like HFC-245cb, HFC-1234yf, and HFC-1234ze.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Adaptability or versatility

If existing fluorination methods are used to produce refrigerants like HFC-245fa and HFC-1234yf, then specific compounds can be obtained, but the process requires multiple separate reactions and cannot efficiently produce multiple valuable compounds from a single starting material

Engineering Contradiction:
Improveability to produce multiple compounds from single starting materialVSAvoidproduction efficiency
Core Design Contradiction:
Adaptability or versatilityVSProductivity

Solution Approach 1:

The patent applies universality by developing a single fluorination process that can produce multiple different refrigerant compounds (HFC-245fa, HFC-1234yf, HFC-1234ze, etc.) from a common starting material (1,1,1,3,3-pentachloropropane). The process uses HF and Cl2 in specific molar ratios to enable selective formation of different products, making the reaction system multi-functional rather than requiring separate dedicated processes for each compound.

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

Solution Approach 2:

The patent applies segmentation by controlling the fluorination process to produce a mixture of compounds that are then separated through distillation or other separation techniques. The process segments the production of different refrigerants from a single reaction, allowing each compound to be isolated and purified individually while maintaining efficient use of the starting material.

Inventive Principle:
Principle #1Segmentation

2Productivity

If stoichiometric ratios of HF to starting material are used, then complete conversion is achieved, but the process becomes more complex and harder to control

Engineering Contradiction:
Improveconversion efficiencyVSAvoidprocess control complexity
Core Design Contradiction:
ProductivityVSDevice complexity

Solution Approach 1:

The patent applies parameter changes by optimizing the molar ratio of HF to starting material to be greater than stoichiometric (excess HF). This parameter change simplifies process control by ensuring complete conversion of the starting material while the excess HF can be easily removed in downstream processing. The patent also optimizes the molar ratio of Cl2 to HF and controls reaction temperature and pressure to achieve high conversion efficiency with manageable process complexity.

Inventive Principle:
Principle #35Parameter changes

3Ease of manufacture

If multiple separate processes are used to produce different refrigerants, then each compound can be optimized individually, but the overall manufacturing cost and process complexity increase

Engineering Contradiction:
Improvemanufacturing simplicityVSAvoidyield of desired compounds
Core Design Contradiction:
Ease of manufactureVSQuantity of substance

Solution Approach 1:

The patent applies merging by combining multiple refrigerant production pathways into a single integrated fluorination process. Instead of using separate processes for producing HFC-245fa, HFC-1234yf, and other refrigerants, the patent uses one unified process that produces all these compounds simultaneously from 1,1,1,3,3-pentachloropropane, thereby simplifying manufacturing operations and improving overall yield efficiency.

Inventive Principle:
Principle #5Merging (Combining)

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 target compounds with high efficiency, enabling the production of valuable refrigerants and intermediates while optimizing the use of starting materials and catalysts, thereby addressing the need for new refrigerants with reduced global warming potential.

Implementation Method 1

The reaction of at least one compound selected from halopropanes of the formula CX3CH2CH2X and halopropenes of the formula CX3CH═CH2 and CX2═CHCH2X with HF and Cl2 in a reaction zone, optionally in the presence of a chlorofluorination catalyst

Methodology Applied
Scientific EffectCatalysis: Catalysis

Data Source

PatentUSRE49849E1Processes for the production of fluoropropanes and halopropenes
Publication Date: 2024.02.27 THE CHEMOURS CO FC LLC

AI summary

A process is disclosed for making CF3CF2CH3, CF3CF═CH2 and/or CF3CCl═CH2. The process involves reacting at least one starting material selected from the group consisting of halopropanes of the formula CX3CH2CH2X, halopropenes of the formula CX3CH═CH2 and halopropenes of the formula CX2═CHCH2X, wherein each X is independently F or Cl, with HF and Cl2 in a reaction zone to produce a product mixture comprising HF, HCl, CF3CF2CH3, CF3CF═CH2, and CF3CCl═CH2; and recovering the CF3CF2CH3, CF3CF═CH2 and/or CF3CCl═CH2 from the product mixture. Also disclosed is a process for making CF3CH2CHF2, CF3CH═CHF, and/or CF3CH═CHCl. This process involves reacting at least one starting material selected from the group consisting of halopropenes of the formula CX3CH═CH2 and halopropenes of the formula CX2═CHCH2X, wherein each X is independently F or Cl, with HF and Cl2 in a reaction zone to produce a product mixture comprising HF, HCl, CF3CH2CHF2, CF3CH═CHF and CF3CH═CHCl; and recovering the CF3CH2CHF2, CF3CH═CHF, and/or CF3CH═CHCl from the product mixture. The molar ratio of HF to the total amount of starting materials fed to the reaction zone for both of these processes is at least stoichiometric, and the molar ratio of Cl2 to total amount of starting material fed to the reaction zone for both of these processes is 2:1 or less.