Fluorinated Cis-Alkene Preparation Process
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Solution Overview
Problem
Current methods lack an efficient process for producing hexafluoro-2-butene (HFO-1336) from readily available raw materials, which is a low global warming potential blowing agent, refrigerant, and solvent.
Innovation Solution
A multi-step process involving the reaction of 1,1,1-trichloro-2,2,2-trifluoroethane with ethene compounds, followed by chlorination and fluorination reactions, and finally dehydrochlorination to produce cis-hexafluororo-2-butene, utilizing catalysts and photochemical or thermal conditions to facilitate the necessary chemical transformations.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Productivity
If current methods are used to produce hexafluoro-2-butene, then production can proceed with existing processes, but the process lacks efficiency and does not utilize readily available raw materials effectively
Solution Approach 1:
The patent changes the chemical parameters by selecting specific raw materials (1,1,1-trichloro-2,2,2-trifluoroethane and 1,2-dichloroethane) and controlling reaction conditions (temperature, pressure, catalysts) to optimize the production process for higher efficiency and better raw material utilization
Solution Approach 2:
The patent extracts and isolates the desired cis-hexafluoro-2-butene product from the reaction mixture through separation steps, achieving high purity product while maintaining efficient use of readily available raw materials
2Manufacturing precision
If multiple reaction steps are implemented to achieve the desired product, then product purity and specificity can be improved, but process complexity increases
Solution Approach 1:
The patent divides the synthesis process into distinct sequential steps: (a) reaction of 1,1,1-trichloro-2,2,2-trifluoroethane with 1,2-dichloroethane, (b) chlorination, (c) fluorination, and (d) dehydrochlorination. Each step is optimized independently to achieve high product purity while managing overall process complexity
Solution Approach 2:
The patent uses specific catalysts as intermediaries in each reaction step to facilitate the transformations. These catalysts enable the reactions to proceed with high selectivity, improving manufacturing precision without requiring overly complex process conditions
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 converts readily available raw materials into cis-hexafluororo-2-butene, offering a sustainable method for producing a compound with low global warming potential, suitable for various applications.
Implementation Method 1
contacting 1,1,1-trichloro-2,2,2-trifluoroethane (CFC-113a) with an ethene compound having two, three or four chlorine substituents in the presence of a catalyst under conditions effective to facilitate an addition reaction
Implementation Method 2
contacting chlorine with the product stream formed in step (a) under conditions effective to facilitate a chlorination reaction and to form a product stream comprising CF3CCl2CCl2CCl3
Implementation Method 3
contacting HF with the CF3CCl2CCl2CCl3 formed in step (a) or step (b) under conditions effective to facilitate a fluorination reaction and to form a product stream comprising CF3CCl2CCl2CF3
Implementation Method 4
dehydrochlorinating and reducing the CF3CCl2CCl2CF3 and/or 2,3-dichloro-1,1,1,4,4,4-hexafluoro-2-butene formed in step (c) under conditions effective to form a product stream comprising cis-1,1,1,4,4,4-hexafluoro-2-butene
Data Source
AI summary
Disclosed is a process for the preparation of fluorine-containing olefins comprising contacting a chlorofluoroalkane with hydrogen in the presence of a catalyst at a temperature sufficient to cause replacement of the chlorine substituents of the chlorofluoroalkane with hydrogen to produce a fluorine-containing olefin. Also disclosed are catalyst compositions for the hydrodechlorination of chlorofluoroalkanes comprising copper metal deposited on a support, and comprising palladium deposited on calcium fluoride, poisoned with lead and reducing the in the presence or absence of a dehydrochlorination catalyst under conditions effective to form a product stream comprising cis-1,1,1,4,4,4-hexafluoro-2-butene (HFO-1336).