HFO-1234ZE, HFO-1225ZC and HFO-1234YF compositions and processes for producing and using the compositions

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Solution Overview

Problem

Current methods for producing HFO-1234ze and HFO-1234yf require additional purification or separation steps to remove excess Z-isomer, increasing costs and complexity, while there is a need for a process that minimizes or eliminates these steps and produces compositions with specific mole percentages of HFO-1225zc and HFO-1234yf.

Innovation Solution

A method involving contacting a mixture of 1,1,1,3,3-pentafluoropropane and Z-1,3,3-tetrafluoropropene with a catalyst like fluorinated Cr2O3 or Cr/Ni on alumina in the gas phase, in the presence of an oxygen-containing gas, to produce a mixture comprising Z-1,3,3-tetrafluoropropene, E-1,3,3-tetrafluoropropene, 1,1,3,3-pentafluoropropene, and 2,3,3-tetrafluoropropene without the need for purification or separation of excess 2,3,3-tetrafluoropropene.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Productivity

If dehydrofluorination of HFC-245fa is performed using conventional catalysts or liquid phase methods, then HFO-1234ze and HFO-1234yf are produced, but a mixture of Z-isomer and E-isomer is formed requiring additional separation or isomerization steps

Engineering Contradiction:
Improveproduction efficiencyVSAvoidprocess complexity
Core Design Contradiction:
ProductivityVSDevice complexity

Solution Approach 1:

The patent changes the chemical parameters of the catalyst system by using fluorinated chromium oxide or chromium-nickel on fluorinated alumina instead of conventional catalysts. This parameter change in catalyst composition and fluorination state selectively promotes E-isomer formation while suppressing Z-isomer formation, eliminating the need for separation or isomerization steps and simplifying the overall process.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent replaces the mechanical separation process (distillation or chromatography required to separate Z and E isomers) with a chemical substitution approach using fluorinated catalysts that selectively produce the desired E-isomer. This substitution eliminates complex separation equipment and reduces process complexity.

Inventive Principle:
Principle #28Mechanics substitution (Replace mechanical system)

2Manufacturing precision

If Z-isomer is separated from the product mixture, then pure E-isomer is obtained, but additional purification steps and costs are incurred

Engineering Contradiction:
Improveisomer purityVSAvoidmanufacturing simplicity
Core Design Contradiction:
Manufacturing precisionVSEase of manufacture

Solution Approach 1:

The patent applies preliminary action by using fluorinated catalysts that prevent Z-isomer formation during the dehydrofluorination reaction itself. By addressing the isomer distribution at the source during product formation rather than treating it afterward through separation, the process achieves high E-isomer purity directly from the reactor without requiring downstream purification steps.

Inventive Principle:
Principle #10Preliminary action

Solution Approach 2:

The patent converts the harmful effect of Z-isomer formation (which requires separation) into a benefit by using fluorinated catalysts that selectively suppress Z-isomer formation. The potential harm of isomer mixture is transformed into the benefit of selective E-isomer production through catalyst design, eliminating the need for additional purification while maintaining manufacturing simplicity.

Inventive Principle:
Principle #22Blessing in disguise (Convert harm into benefit)

3Manufacturing precision

If isomerization or conversion steps are added to handle Z-isomer, then product composition is controlled, but process cost increases

Engineering Contradiction:
Improveproduct composition controlVSAvoidproduction cost
Core Design Contradiction:
Manufacturing precisionVSEase of manufacture

Solution Approach 1:

The patent changes the catalyst parameters to fluorinated chromium oxide or chromium-nickel on fluorinated alumina, which fundamentally alters the reaction pathway to selectively produce E-isomer. This parameter change in catalyst composition eliminates the need for additional isomerization or conversion steps, maintaining precise product composition control while reducing production costs by removing extra process units.

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 compositions with desired mole percentages of HFO-1234ze, HFO-1225zc, and HFO-1234yf, reducing the need for additional purification steps and enhancing the economic viability of the production process.

Implementation Method 1

contacting a mixture of 1,1,1,3,3-pentafluoropropane and Z-1,3,3-tetrafluoropropene with a catalyst like fluorinated Cr2O3 or Cr/Ni on alumina in the gas phase

Methodology Applied
Scientific EffectCatalysis: Catalysis

Data Source

PatentUS11913681B2HFO-1234ZE, HFO-1225ZC and HFO-1234YF compositions and processes for producing and using the compositions
Publication Date: 2024.02.27 THE CHEMOURS CO FC LLC

AI summary

A fluoropropene composition comprising Z-1,3,3,3-tetrafluoropropene, E-1,3,3,3-tetrafluoropropene, 1,1,3,3,3-pentafluoropropene, 2,3,3,3-tetrafluoropropene, and optionally 1,1,1,3,3-pentafluoropropane wherein the 2,3,3,3-tetrafluoropropene being present in an amount of 0.00001 to 1.0%. A method of producing the fluoropropene, methods for using the fluoropropene and the composition formed are also disclosed.