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 in the gas phase with a catalyst like fluorinated Cr2O3 or Cr/Ni on alumina, 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 catalytic dehydrofluorination of HFC-245fa is used to produce HFO-1234ze, then HFO-1234ze can be produced, but a mixture of E-isomer and Z-isomer is formed requiring additional separation or isomerization steps

Engineering Contradiction:
Improveproduction of HFO-1234zeVSAvoidseparation and isomerization steps
Core Design Contradiction:
ProductivityVSDevice complexity

Solution Approach 1:

The patent converts the harmful Z-isomer byproduct into a beneficial component by isomerizing it to the desired E-isomer in-situ within the reaction system. The Z-isomer, which would normally require costly separation and disposal, is transformed into the valuable E-isomer product, eliminating the need for separate purification steps and reducing overall process complexity.

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

Solution Approach 2:

The patent merges the dehydrofluorination reaction and Z-isomer isomerization into a single integrated catalytic system. By combining these two functions in one reactor with a dual-function catalyst, the process eliminates the need for separate isomerization equipment and operational steps, thereby reducing device complexity while maintaining high productivity.

Inventive Principle:
Principle #5Merging (Combining)

2Manufacturing precision

If Z-isomer is separated and isomerized in a separate step, then E-isomer purity is improved, but additional cost and process steps are required

Engineering Contradiction:
ImproveE-isomer purityVSAvoidprocess cost and complexity
Core Design Contradiction:
Manufacturing precisionVSEase of manufacture

Solution Approach 1:

The patent transforms the Z-isomer impurity into a valuable E-isomer product through in-situ isomerization, converting a manufacturing burden into a benefit. This approach maintains high E-isomer purity while eliminating the need for costly separate isomerization operations, thereby improving ease of manufacture without sacrificing product quality.

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

Solution Approach 2:

The catalytic system performs self-service by automatically isomerizing the Z-isomer to E-isomer within the reaction mixture itself. The catalyst continuously converts any Z-isomer formed during dehydrofluorination into the desired E-isomer, maintaining product purity without requiring external intervention or additional processing steps.

Inventive Principle:
Principle #25Self-service

3Ease of manufacture

If HFO-1234yf is produced as a byproduct, then the reaction pathway is simplified, but purification steps are needed to remove excess HFO-1234yf

Engineering Contradiction:
Improvereaction pathway simplicityVSAvoidpurification steps
Core Design Contradiction:
Ease of manufactureVSDevice complexity

Solution Approach 1:

The patent converts the HFO-1234yf byproduct, which would normally require purification removal, into a beneficial component by isomerizing it to HFO-1234ze in-situ. This transformation eliminates the need for purification steps to remove HFO-1234yf while maintaining reaction pathway simplicity, as the same catalyst handles both dehydrofluorination and isomerization functions.

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

Solution Approach 2:

The patent changes the chemical parameter of HFO-1234yf by isomerizing its double bond configuration from the 2,3-position to the 3,4-position, transforming it into HFO-1234ze. This parameter change converts a unwanted byproduct into a desired product, simplifying the overall purification requirements while maintaining the simplicity of the reaction pathway.

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 in the gas phase with a catalyst like fluorinated Cr2O3 or Cr/Ni on alumina

Methodology Applied
Scientific EffectCatalysis: Catalysis

Data Source

PatentUS11592217B2HFO-1234ze, HFO-1225zc and HFO-1234yf compositions and processes for producing and using the compositions
Publication Date: 2023.02.28 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.