Halogenated Partially Fluorinated Compound Synthesis via Halogen Salt Addition
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Solution Overview
Problem
Current methods for producing partially fluorinated compounds are complex, use less readily available starting materials, and are costly, necessitating the development of simpler and more cost-effective alternatives.
Innovation Solution
A method involving the reaction of a compound with the structure Rf-CF=CXY, where X and Y are independently F and Cl, with an iodine or bromine containing salt in the presence of an acid or an aqueous solution of HZ, to form a halogenated partially fluorinated compound R'f-CFH-CXYZ, utilizing readily available fluorinated monovalent groups and optimizing reaction conditions for improved yield.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Ease of manufacture
If current methods for producing partially fluorinated compounds are used, then the compounds can be produced, but the process complexity increases and costs increase
Solution Approach 1:
The patent segments the complex multi-step synthesis processes into simpler individual reaction steps. Instead of using complex sequences involving multiple reagents and conditions, the invention breaks down the synthesis into manageable stages using readily available starting materials and straightforward reaction conditions, thereby reducing overall process complexity while maintaining manufacturability
Solution Approach 2:
The patent employs readily available, inexpensive starting materials and simple catalysts that can be easily obtained and disposed of. Rather than using expensive, specialized reagents requiring complex handling and purification, the invention uses common chemical substances that simplify the manufacturing process and reduce both equipment complexity and operational costs
2Ease of manufacture
If current methods for producing partially fluorinated compounds are used, then the compounds can be produced, but the starting materials become less readily available and costs increase
Solution Approach 1:
The patent employs universal starting materials and reagents that have multiple applications in chemical synthesis. The methods use common fluorinated compounds and standard halogenation reagents that can serve multiple purposes in different synthetic routes, ensuring broad availability and reducing dependency on specialized, less accessible materials
Solution Approach 2:
The invention optimizes reaction parameters such as temperature, pressure, and catalyst selection to enable the use of readily available starting materials. By adjusting these parameters, the patent makes the synthesis accessible using common chemical substances rather than requiring rare or specialized materials, thereby improving both availability and ease of manufacture
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 simplifies the production of partially fluorinated compounds, utilizing more accessible starting materials and reducing costs, while achieving high yields and flexibility in fluorinated monovalent group modifications, suitable for use in polymer synthesis and as chain transfer agents or cure site monomers.
Implementation Method 1
contacting the compound with at least one of (i) an iodine or bromine containing salt in the presence of an acid; and (ii) aqueous solution of HZ wherein Z is selected from I and Br to form the halogenated partially fluorinated compound
Data Source
AI summary
Described herein is method of making a halogenated partially fluorinated compound, comprising: (a) providing a compound having the following structure of formula (I): Rf-CF=CXY wherein X and Y are independently selected from F and C1; wherein Rf is a fluorinated monovalent group comprising 1 to 10 carbon atoms; (b) contacting the compound with at least one of (i) an iodine or bromine containing salt in the presence of an acid; and (ii) aqueous solution of HZ wherein Z is selected from I and Br to form the halogenated partially fluorinated compound of the formula (II): R'f-CFH-CXYZ wherein X and Y are independently selected from F and C1; Z is selected from I and Br; and R'f is a fluorinated monovalent group comprising 1 to 10 carbon atoms.