Halogenated Fluorinated Ether Synthesis via Difluorosulfuryl Peroxide
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Solution Overview
Problem
There is a need for alternative and cost-effective compounds and methods to produce chain transfer agents or cure site monomers for fluoropolymer synthesis, particularly using readily available starting materials such as fluorosulfonic acid, tetrafluoroethylene, hexafluoropropylene oxide, elemental halogens, and interhalogens.
Innovation Solution
The methods involve chlorinating, brominating, or iodinating difluorosulfuryl peroxide followed by reaction with fluoroolefins to form halogenated fluoroorganyl acid fluorides, which are then reacted with other fluoroolefins or hexafluoropropylene oxide to produce chlorinated, brominated, or iodinated fluorinated ether-containing compounds, or using cyanide-containing compounds with tetrafluoroethylene to form 2,2,3,3-tetrafluoro-3-halogenopropanenitrile, and subsequently converting these into halogenated fluorinated ether-containing compounds.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Ease of manufacture
If conventional methods using expensive or less available starting materials are used to produce halogenated fluorinated ether-containing compounds, then the product quality and performance can be maintained, but the manufacturing cost increases and material availability decreases
Solution Approach 1:
The patent replaces expensive, specialized starting materials with cheap, readily available materials such as fluorosulfonic acid, tetrafluoroethylene, hexafluoropropylene oxide, and interhalogens. These inexpensive reagents serve as effective substitutes for traditional costly precursors while maintaining the ability to produce high-performance halogenated fluorinated ether-containing compounds suitable for chain transfer agents and cure site monomers
Solution Approach 2:
The patent employs novel reaction conditions and catalyst systems that enable the transformation of simple, available starting materials into complex fluorinated ether compounds. By optimizing reaction parameters such as temperature, pressure, and catalyst selection (e.g., using aluminum halides or boron trichloride), the process achieves high yields and product quality despite using basic feedstocks
2Ease of manufacture
If conventional synthesis routes are used, then established product performance can be achieved, but the complexity of the manufacturing process and availability of starting materials are reduced
Solution Approach 1:
The synthesis process is divided into distinct sequential steps: (1) formation of difluorosulfuryl peroxide from fluorosulfonic acid, (2) reaction with fluoroolefin to form halogenated fluoroorganyl acid fluoride, and (3) conversion to the final fluorinated ether-containing compound. This segmentation allows each step to be optimized independently and facilitates the use of readily available materials at each stage
Solution Approach 2:
The patent uses difluorosulfuryl peroxide and halogenated fluoroorganyl acid fluorides as key intermediate compounds that bridge the gap between simple, available starting materials and the desired complex fluorinated ether products. These intermediates serve as versatile building blocks that can be prepared from common reagents and subsequently transformed into various final products
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
These methods provide new halogenated fluorinated ether-containing compounds that can be used as chain transfer agents or cure site monomers in fluoropolymer synthesis, offering cost-effective alternatives and utilizing readily available materials, suitable for various applications including seals and molded parts in harsh environments.
Implementation Method 1
chlorinating, brominating or iodinating a difluorosulfuryl peroxide followed by reaction with a first fluoroolefin to form a chlorinated, brominated or iodinated fluoroorganyl acid fluoride
Implementation Method 2
reacting the chlorinated, brominated or iodinated fluoroorganyl acid fluoride with a first compound selected from at least one of: (a) a second fluoroolefin in the presence of I2, Br2 or XYn
Implementation Method 3
adding XCN to TFE wherein X is I, Br or Cl
Implementation Method 4
reacting the chlorinated, brominated or iodinated fluoroorganyl acid fluoride with HFPO to form a corresponding acid fluoride
Data Source
AI summary
Described herein are three methods for making halogenated fluorinated ether-containing compounds using a fluorinated olefin or hexafluoropropylene oxide.