Isomerization Catalyst for Cis-HFO-1336 Yield
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Solution Overview
Problem
Current methods for producing cis-1,1,1,4,4,4-hexafluoro-2-butene (HFO-1336) do not efficiently yield the cis-isomer, which is preferred for various applications, due to limitations in existing processes for isomerization and selectivity.
Innovation Solution
A process involving the reaction of carbon tetrachloride and 3,3,3-trifluoropropene, using specific metal catalyst complexes and fluorination catalysts, followed by dehydrochlorination and isomerization steps, to produce cis-1,1,1,4,4,4-hexafluoro-2-butene, with the trans-isomer being converted to the cis-isomer using an isomerization catalyst, thereby increasing the single pass yield of the cis-isomer.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Manufacturing precision
If existing processes are used to produce cis-1,1,1,4,4,4-hexafluoro-2-butene, then production can proceed with conventional methods, but the yield and selectivity of the cis-isomer are low
Solution Approach 1:
The patent employs an isomerization catalyst to change the physical-chemical parameters of the trans-isomer, converting it into the desired cis-isomer. This parameter change approach transforms the unwanted trans-isomer product into the valuable cis-isomer, thereby improving both selectivity and yield without requiring complete suppression of trans-isomer formation in the initial reaction
Solution Approach 2:
An isomerization catalyst is introduced as an intermediary substance that mediates the conversion of trans-isomer to cis-isomer. The catalyst facilitates the isomerization reaction, enabling the transformation of the unwanted trans-isomer into the desired cis-isomer form, thus resolving the low selectivity and yield problem
2Productivity
If existing processes are used to produce cis-1,1,1,4,4,4-hexafluoro-2-butene, then the process can be maintained as is, but the conversion efficiency is insufficient
Solution Approach 1:
The patent implements a continuous isomerization process where trans-isomer is continuously converted to cis-isomer through catalytic action. This continuous useful action ensures that the desired cis-isomer is constantly being produced from the trans-isomer, maintaining high conversion efficiency and single pass yield throughout the process
Solution Approach 2:
By introducing the isomerization catalyst, the patent changes the reaction parameters to enable efficient isomerization. This parameter change allows the system to achieve both high conversion efficiency and high single pass yield of the cis-isomer simultaneously
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 enhances the yield and selectivity of the cis-isomer, achieving high conversion and selectivity rates, making it more efficient and effective for producing cis-hexafluoro-2-butene.
Implementation Method 1
contacting carbon tetrachloride with 3,3,3-trifluoropropene in the presence of an effective amount of a metal catalyst complex comprising a metal and an organic ligand under conditions effective to facilitate an addition reaction
Implementation Method 2
contacting HF with the CF3CHClCH2CCl3 formed in (a) in the presence or absence of a fluorination catalyst under conditions effective to facilitate a fluorination reaction
Implementation Method 3
contacting the trans-1,1,1,4,4,4-hexafluoro-2-butene with an isomerization catalyst under conditions effective to form the cis-1,1,1,4,4,4-hexafluoro-2-butene
Data Source
AI summary
Hexafluoro-2-butene (HFO-1336) is a low global warming potential blowing agent, refrigerant and solvent. This invention provides a method for making the compound, including the cis-isomer, from the readily available raw materials, carbon tetrachloride and 3,3,3-trifluoropropene. The trans-isomer formed in the process can be isomerized into cis-isomer by the use of an isomerization catalyst.