Partially Fluorinated Compounds via Vinylidene Insertion
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Solution Overview
Problem
The preparation of fluorinated diiodides with an odd number of CF2 units has been difficult and costly, as they require handling of tetrafluoroethylene, which is challenging, and the availability of ICF2I is limited, hindering their use in polymer synthesis.
Innovation Solution
The insertion of vinylidene fluoride into perfluorinated diiodo-compounds leads to the formation of partially fluorinated compounds that can be used as chain transfer agents or cure site monomers, enabling faster reaction rates and higher incorporation in polymer synthesis, and these compounds can be dehydroiodinated to form partially fluorinated iodoalkene or dialkene compounds.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Reliability
If traditional methods using tetrafluoroethylene are employed to prepare fluorinated diiodides with an odd number of CF2 units, then the compounds can be obtained, but the process becomes difficult and costly due to handling challenges and limited availability of ICF2I
Solution Approach 1:
The invention extracts the problematic tetrafluoroethylene component from the synthesis route and replaces it with perfluorinated diiodo-compounds as the starting material. This extraction of the difficult-to-handle reagent resolves the contradiction by eliminating the handling challenges and availability issues while maintaining the ability to produce fluorinated diiodides with odd CF2 units
Solution Approach 2:
The invention employs perfluorinated diiodo-compounds as disposable starting materials that can be readily converted into the desired partially fluorinated compounds. These starting materials are more readily available and easier to handle than ICF2I, making the overall process more cost-effective and less difficult despite being used in a single transformation step
2Productivity
If conventional partially fluorinated compounds are used in polymer synthesis, then polymerization can proceed, but the reaction rates are slower and incorporation into the polymer is lower
Solution Approach 1:
The invention changes the structural parameters of the partially fluorinated compounds by introducing vinyl group-containing structures (such as CF2=CH- groups) adjacent to the iodine atoms. This parameter change in molecular structure enhances both the reaction rate and incorporation into polymers while maintaining compatibility with fluoroolefin comonomers, resolving the contradiction between 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 method provides a more efficient and cost-effective route to partially fluorinated compounds that enhance polymer synthesis by offering improved compatibility with fluoroolefin comonomers, leading to faster reaction rates and higher incorporation, thus overcoming the limitations of traditional methods.
Implementation Method 1
The insertion of vinylidene fluoride into perfluorinated diiodo-compounds leads to the formation of partially fluorinated compounds
Implementation Method 2
these compounds can be dehydroiodinated to form partially fluorinated iodoalkene or dialkene compounds
Data Source
AI summary
Described herein is a composition comprising a partially fluorinated compound selected from the group consisting of: (a) I(CF2)XCH2CF2I; (b) ICF2CH2(CF2)XCH2CF2I; (c) I(CF2)yCH=CF2; (d) CF2=CH(CF2)yCH2CF2I; and (e) CF2=CH(CF2)yCH=CF2 wherein x is an odd integer selected from 3 to 11, and y is an integer greater than 2, along with methods of making and polymerizing such compounds.