HFO-1234yf Synthesis via Segmented Fluorination

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Solution Overview

Problem

Current methods for producing hydrofluoropropenes, such as HFO-1234yf, are inefficient and lack a cost-effective process to replace chlorofluorocarbons while addressing greenhouse gas emissions and ozone depletion potential.

Innovation Solution

A two-step process involving gas phase or liquid phase fluorination followed by catalytic gas phase fluorination using chromium-based catalysts to convert tetrachloropropenes into 1,1,1,2-tetrafluoropropene (HFO-1234yf), with co-products recycled to enhance efficiency.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Productivity

If current methods for producing hydrofluoropropenes are used, then production can be achieved, but the process is inefficient and lacks cost-effectiveness

Engineering Contradiction:
Improveproduction efficiencyVSAvoidcost-effectiveness
Core Design Contradiction:
ProductivityVSEase of manufacture

Solution Approach 1:

The patent divides the production process into two distinct steps: first fluorination to form HCFO-1233xf intermediate, then second fluorination to produce HFO-1234yf. This segmentation allows optimization of each step independently, improving overall efficiency and cost-effectiveness compared to single-step methods

Inventive Principle:
Principle #1Segmentation

Solution Approach 2:

The patent introduces HCFO-1233xf as an intermediate compound in the reaction pathway. This intermediary enables a more controlled and efficient two-step fluorination process, replacing inefficient current methods while reducing costs through better process control and selectivity

Inventive Principle:
Principle #24Intermediary (Mediator)

2Reliability

If chlorofluorocarbons are used, then refrigeration performance is achieved, but they cause ozone depletion and global warming

Engineering Contradiction:
Improverefrigeration performanceVSAvoidozone depletion potential
Core Design Contradiction:
ReliabilityVSObject-affected harmful factors

Solution Approach 1:

The patent changes the chemical composition parameters by producing hydrofluoropropenes (HFO-1234yf) with different molecular structure and fluorination patterns compared to chlorofluorocarbons. This parameter change eliminates chlorine atoms responsible for ozone depletion while maintaining the refrigeration performance through optimized fluorinated hydrocarbon structure

Inventive Principle:
Principle #35Parameter changes

3Object-affected harmful factors

If hydrofluorocarbons are used to replace chlorofluorocarbons, then ozone depletion potential is reduced, but they remain greenhouse gases

Engineering Contradiction:
Improveozone depletion potentialVSAvoidgreenhouse gas emissions
Core Design Contradiction:
Object-affected harmful factorsVSObject-generated harmful factors

Solution Approach 1:

The patent produces HFO-1234yf with a specific molecular structure containing a double bond and fluorine atoms at positions that reduce global warming potential. The parameter changes in molecular structure (unsaturated hydrofluoropropene vs. saturated hydrofluorocarbon) lead to lower GWP while maintaining zero ODP

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 process effectively produces HFO-1234yf with reduced environmental impact, achieving high conversion rates and recyclable co-products, thus addressing the need for environmentally friendly alternatives to chlorofluorocarbons.

Implementation Method 1

b) gas phase, catalytic fluorination of the intermediate HCFO-1233xf to form the hydrofluoropropene product 1,1,1,2-tetrafluoropropene (HFO-1234yf)... in the presence of a catalyst selected from the group consisting of supported chromium catalyst, unsupported chromium catalyst and mixtures thereof

Methodology Applied
Scientific EffectCatalysis: Catalysis

Data Source

PatentEP3135657B1Process for the manufacture of hydrofluoroolefins
Publication Date: 2019.03.27 ARKEMA INC
  • EP3135657B1 patent drawing
  • EP3135657B1 patent drawing
  • EP3135657B1 patent drawing

AI summary

In this invention we are disclosing a process for the synthesis of hydrochlorofluoroolefins (HCFO) and/or hydrofluoroolefins (HFO). The process is based on the steps of fluorination of hydrochloropropenes or hydrochloropropanes to form hydrochlorofluoropropenes and/or hydrofluoropropenes, followed by gas phase, catalytic fluorination of the hydrochlorofluoropropenes to form hydrofluoropropenes.