Perfluorinated Solvent Liquid Phase Epoxidation Selectivity
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Solution Overview
Problem
Current methods for selective oxidation of olefins to epoxides using molecular oxygen face challenges, particularly in achieving high selectivity and avoiding co-product formation, especially for olefins other than ethylene in liquid phase reactions.
Innovation Solution
The use of perfluorinated solvents with high boiling points and specific catalysts, such as transition metal compounds and heterogeneous catalysts supported on phyllosilicates, in a liquid phase reactor to facilitate selective oxidation of olefins to epoxides using molecular oxygen, allowing for continuous operation and high selectivity.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Loss of substance
If liquid phase selective oxidation of olefins is performed using molecular oxygen, then co-product-free epoxide production is achieved, but process selectivity is low due to reactive hydrogen atoms in allylic position
Solution Approach 1:
The patent changes the physical state parameter from gas phase to liquid phase, and introduces perfluorinated solvents with specific properties (high oxygen solubility, high boiling point) to alter the reaction environment. This resolves the contradiction by enabling liquid phase operation with molecular oxygen while maintaining selectivity through the unique properties of perfluorinated solvents that suppress allylic hydrogen abstraction.
Solution Approach 2:
The patent introduces perfluorinated solvents as intermediaries that mediate between molecular oxygen and the olefin substrate. These solvents serve multiple functions: dissolving oxygen to increase its availability, stabilizing reaction intermediates, and creating a reaction environment that favors epoxidation over allylic oxidation, thus resolving the selectivity issue.
2Productivity
If gas phase epoxidation is performed with molecular oxygen, then ethylene epoxidation is effective, but epoxidation of other olefins is difficult due to low process selectivity
Solution Approach 1:
The patent develops a universal liquid phase epoxidation system using perfluorinated solvents that works for multiple olefin substrates (ethylene, propylene, butenes, etc.) rather than being limited to ethylene only. The perfluorinated solvent system provides a versatile platform that maintains high selectivity across different olefin types, resolving the contradiction between productivity and substrate scope.
3Productivity
If high boiling point perfluorinated solvents are used, then continuous liquid phase operation is enabled, but solvent selection is limited
Solution Approach 1:
The patent identifies and utilizes a specific range of perfluorinated solvents with boiling points above 80°C, changing the parameter of solvent boiling point to enable continuous operation. This parameter change resolves the contradiction by selecting solvents that are volatile enough for continuous processing but have high enough boiling points to remain liquid at operating temperatures, providing both productivity and adaptability.
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 approach achieves selective oxidation with selectivity to epoxides greater than 40%, 50%, or 60%, and enables continuous operation, reducing byproduct formation by effectively utilizing perfluorinated solvents to dissolve molecular oxygen and support catalysts that enhance the epoxidation process.
Implementation Method 1
perfluorinated solvents with high boiling points and specific catalysts, such as transition metal compounds and heterogeneous catalysts supported on phyllosilicates, in a liquid phase reactor to facilitate selective oxidation of olefins to epoxides using molecular oxygen
Implementation Method 2
selective oxidation is carried out in the presence of a catalyst
Implementation Method 3
carrying out selective oxidation, in liquid phase, of an olefinic compound with molecular oxygen to produce an epoxide
Data Source
AI summary
The present disclosure relates to a method for effecting catalytic selective oxidation in liquid phase comprising a perfluorinated solvent and an olefinic compound with molecular oxygen to produce an epoxide. The method may provide enhanced selectivity to the epoxide of greater than 60%. The olefinic compound may be ethylene, propylene, butenes, 1-octene, butadiene, allyl chloride, allyl alcohol, styrene, and the like. The perfiuormated solvent may be perfluoro methyldecalin, peril uorodecalm, perfluoroperhydrophenanthrene, perfluoro (butyltetrahydrofuran), isomers thereof, or a combination thereof. In some embodiments, the method includes catalytically epoxidizing, in a liquid phase comprising a perfluorinated solvent, propylene with molecular oxygen to produce propylene oxide. A system for carrying out the method is also provided, the system comprising a source of a perfluorinated solvent and a liquid phase reactor fluidlv connected with the source, and configured for effecting catalytic selective oxidation, in a liquid phase comprising the perfiuormated solvent, of an olefinic compound with molecular oxygen to produce an epoxide.