Hydrodechlorination Catalysts for Low GWP Fluoroolefin Production

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Solution Overview

Problem

Current methods for producing fluorinated alkene compounds, such as hydrofluoroolefins (HFOs), face challenges in achieving low global warming potential (GWP) and ozone depletion potential (ODP) while maintaining non-flammability, non-conductivity, and low liquid viscosities.

Innovation Solution

The method involves hydrodechlorinating a compound of formula (1) in the presence of a first catalyst to form a compound of formula (2), which includes fluorinated alkenes like E-1,1,1,2,2,5,5,6,6,6-decafluoro-3-hexene (HFO-153-10mczz) and 1,1,1,4,4,5,5,6,6,6-decafluoro-2-hexene (HFO-153-10mzz), using palladium or aluminum chlorofluoride as catalysts.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If conventional methods are used to produce fluorinated alkene compounds, then production efficiency can be maintained, but the environmental sustainability and safety properties (low GWP, low ODP, non-flammability) cannot be simultaneously achieved

Engineering Contradiction:
Improveenvironmental sustainabilityVSAvoidproduction efficiency
Core Design Contradiction:
ReliabilityVSProductivity

Solution Approach 1:

The patent changes the chemical parameters of the production process by using specific catalysts (palladium on carbon, nickel on carbon, or copper on carbon) and controlling reaction conditions (temperature, pressure, hydrogen to alkene ratio) to produce HFOs with low GWP and ODP while maintaining production efficiency. The method optimizes these parameters to achieve both environmental sustainability and productivity.

Inventive Principle:
Principle #35Parameter changes

2Object-affected harmful factors

If fluorinated alkene compounds are produced with low GWP and ODP, then environmental friendliness is improved, but flammability and conductivity properties may worsen

Engineering Contradiction:
Improveglobal warming potentialVSAvoidflammability
Core Design Contradiction:
Object-affected harmful factorsVSObject-generated harmful factors

Solution Approach 1:

The patent applies local quality by creating specific chemical structures (fluorinated alkene compounds with particular molecular configurations) that locally possess low GWP and ODP properties while the overall compound structure maintains non-flammability and non-conductivity. The specific substitution patterns and molecular arrangements ensure all harmful properties are simultaneously minimized.

Inventive Principle:
Principle #3Local quality

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 effectively produces fluorinated alkenes with low GWP and ODP, which are non-flammable, non-conductive, and have low liquid viscosities, making them suitable as environmentally friendly working fluids and heat exchange fluids.

Implementation Method 1

hydrodechlorinating a compound of formula (1), CnF2n+1CX1═CClC4−nF9−2n (1) wherein n is 1 or 2; and wherein X1 is H or Cl; in the presence of a first catalyst in an amount sufficient to form a composition comprising a compound of formula (2), CnF2n+1CH═CHC4−nF9−2n (2)

Methodology Applied
Scientific EffectHydrodechlorination:

Implementation Method 2

contacting CF3CCl═CClCF3 with CF2═CF2 in the presence of a second catalyst in an amount sufficient to form a composition comprising the compound of formula (1)

Methodology Applied
Scientific EffectCatalysis: Catalysis

Data Source

PatentUS20250178989A1Compositions and methods for making HFO-153-10mzz and HFO-153-10mczz
Publication Date: 2025.06.05 CHEMOURS CO FC LLC THE
  • US20250178989A1 patent drawing
  • US20250178989A1 patent drawing
  • US20250178989A1 patent drawing

AI summary

A method of producing a fluoroolefin includes hydrodechlorinating a compound of formula (1), CnF2n+1CX1═CClC4−nF9−2n, where n is 1 or 2 and where X1 is H or Cl, in the presence of a first catalyst in an amount sufficient to form a composition including a compound of formula (2), CnF2n+1CH═CHC4−nF9−2n. In some embodiments, the method also includes contacting CF3CCl═CClCF3 or CF3CCl═CHCF3 with CF2═CF2 in the presence of a second catalyst in an amount sufficient to form a composition including the compound of formula (1). In other embodiments, the method also includes coupling C2F5CCl3 under conditions sufficient to form a composition including the compound of formula (1). In other embodiments, the method further includes chlorinating C2F5CH3 in the presence of a second catalyst in an amount sufficient to form a composition comprising C2F5CCl3.