Perfluoro(2-methylene-4-methyl-1,3-dioxolane) Production via Aqueous Decarboxylation
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Solution Overview
Problem
Current methods for producing perfluoro(2-methylene-4-methyl-1,3-dioxolane face challenges such as high temperature requirements, generation of toxic by-products, difficulty in scaling up industrial production, and issues with separating the target product from by-products like 2-hydro-perfluoro(2,4-dimethyl-1,3-dioxolane).
Innovation Solution
A method involving the reaction of perfluoro(2,4-dimethyl-2-fluoroformyl-1,3-dioxolane) with a basic aqueous solution containing alkali or alkaline earth metal ions, followed by liquid separation and water content reduction treatments, to facilitate a decarboxylation reaction in a liquid phase system, thereby producing perfluoro(2-methylene-4-methyl-1,3-dioxolane with high yield and minimal by-product formation.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Productivity
If a reaction at high temperature of 295°C is performed using perfluoro(2,4-dimethyl-2-fluoroformyl-1,3-dioxolane) on a sodium carbonate solid catalyst, then the decarboxylation reaction proceeds, but highly toxic fluorophosgenes are generated as by-products and the method is difficult to perform on an industrial scale
Solution Approach 1:
The patent changes the temperature parameter from high temperature (295°C) to moderate temperature (130°C or lower), and changes the catalyst phase from solid to aqueous solution, thereby eliminating toxic fluorophosgene by-products while maintaining reaction efficiency
Solution Approach 2:
The patent introduces an aqueous solution of alkali metal carbonate or alkaline earth metal carbonate as an intermediary medium to facilitate the decarboxylation reaction at lower temperatures without generating toxic by-products, replacing the direct high-temperature solid-catalyst method
2Productivity
If a decarboxylation reaction is performed at high temperature of 250°C to 280°C in a solid phase system using 2-methoxycarbonyl-2-trifluoromethyl-4-methyl-1,3-dioxolane fluorinated with fluorine gas, then the target compound is produced, but the method is difficult to perform on an industrial scale
Solution Approach 1:
The patent changes the reaction temperature from high temperature (250-280°C) to moderate temperature (130°C or lower), and changes the reaction phase from solid to liquid (aqueous solution), thereby improving industrial scalability while maintaining production efficiency
Solution Approach 2:
The patent replaces the solid phase reaction system with a liquid phase (aqueous solution) system, making the process more suitable for industrial manufacturing by improving heat and mass transfer efficiency
3Temperature
If a decarboxylation reaction is performed at low temperature of 130°C in a liquid phase system using potassium perfluoro(2,4-dimethyl-1,3-dioxolane-2-yl)carboxylate and potassium fluoride, then the reaction temperature is reduced, but the target product is obtained as a mixture with 2-hydro-perfluoro(2,4-dimethyl-1,3-dioxolane) by-product that is very difficult to separate by distillation
Solution Approach 1:
The patent optimizes the temperature parameter to be 130°C or lower (preferably 100-120°C) and changes the catalyst to alkali metal carbonate or alkaline earth metal carbonate in aqueous solution, thereby reducing the formation of hard-to-separate by-products while maintaining low temperature operation
Solution Approach 2:
The patent converts the potential harm of low temperature reaction (by-product formation) into a benefit by selecting specific catalysts (alkali metal carbonate or alkaline earth metal carbonate) that promote selective decarboxylation, minimizing by-product formation and simplifying separation
4Productivity
If water content reduction treatments are performed on the liquid containing perfluoro(2,4-dimethyl-1,3-dioxolane-2-yl)carboxylic acid alkali metal salts or perfluoro(2,4-dimethyl-1,3-dioxolane-2-yl)carboxylic acid alkaline earth metal salts, then the decarboxylation reaction can be performed in a liquid phase system with high yield, but additional processing steps are required
Solution Approach 1:
The patent performs water content reduction treatments (evaporation or adsorption) on the aqueous solution before decarboxylation to ensure high reaction yield, maintaining continuous improvement of product quality through sequential processing steps
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 method allows for industrial-scale production of perfluoro(2-methylene-4-methyl-1,3-dioxolane with high yield and reduced by-product formation, specifically minimizing the production of 2-hydro-perfluoro(2,4-dimethyl-1,3-dioxolane, making the process more feasible and efficient.
Implementation Method 1
reacting at least one of perfluoro(2,4-dimethyl-2-fluoroformyl-1,3-dioxolane) and a hydrolysis product thereof with a basic aqueous solution
Implementation Method 2
reacting with a basic aqueous solution containing one or more cations selected from the group consisting of alkali metal ions and alkaline earth metal ions
Implementation Method 3
separating a liquid containing produced perfluoro(2,4-dimethyl-1,3-dioxolane-2-yl)carboxylic acid alkali metal salts or perfluoro(2,4-dimethyl-1,3-dioxolane-2-yl)carboxylic acid alkaline earth metal salts by a liquid separation operation
Implementation Method 4
performing one or more water content reduction treatments selected from the group consisting of water evaporation and water adsorption
Implementation Method 5
performing one or more water content reduction treatments selected from the group consisting of water evaporation and water adsorption
Implementation Method 6
causing a decarboxylation reaction in a liquid phase system with the obtained perfluoro(2,4-dimethyl-1,3-dioxolane-2-yl)carboxylic acid alkali metal salts or perfluoro(2,4-dimethyl-1,3-dioxolane-2-yl)carboxylic acid alkaline earth metal salts
Implementation Method 7
thermally decomposed
Data Source
AI summary
Provided is a method of producing perfluoro(2-methylene-4-methyl-1,3-dioxolane), the method including at least following processes (1) to (3): (1) reacting at least one of perfluoro(2,4-dimethyl-2-fluoroformyl-1,3-dioxolane) and a hydrolysis product thereof with a basic aqueous solution containing one or more cations selected from the group consisting of alkali metal ions and alkaline earth metal ions and then separating a liquid containing produced perfluoro(2,4-dimethyl-1,3-dioxolane-2-yl)carboxylic acid alkali metal salts or perfluoro(2,4-dimethyl-1,3-dioxolane-2-yl)carboxylic acid alkaline earth metal salts by a liquid separation operation; (2) performing one or more water content reduction treatments selected from the group consisting of water evaporation and water adsorption on the liquid containing the obtained perfluoro(2,4-dimethyl-1,3-dioxolane-2-yl)carboxylic acid alkali metal salts or perfluoro(2,4-dimethyl-1,3-dioxolane-2-yl)carboxylic acid alkaline earth metal salts to obtain perfluoro(2,4-dimethyl-1,3-dioxolane-2-yl)carboxylic acid alkali metal salts or perfluoro(2,4-dimethyl-1,3-dioxolane-2-yl)carboxylic acid alkaline earth metal salts in a solution state or a solid state; and (3) causing a decarboxylation reaction in a liquid phase system with the obtained perfluoro(2,4-dimethyl-1,3-dioxolane-2-yl)carboxylic acid alkali metal salts or perfluoro(2,4-dimethyl-1,3-dioxolane-2-yl)carboxylic acid alkaline earth metal salts in a solution state or a solid state to produce perfluoro(2-methylene-4-methyl-1,3-dioxolane).