Allylic Unsaturated Hydrofluoroamine Compounds for Low GWP Fluids
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Solution Overview
Problem
There is a need for inert fluorinated fluids with low global warming potential, high thermal stability, non-flammability, and a wide operating temperature range to replace traditional fluorinated compounds used in applications like heat transfer, solvent cleaning, and fire extinguishing, while also being environmentally friendly and cost-effective.
Innovation Solution
Development of allylic terminally unsaturated hydrofluorinated compounds comprising an amine and/or ether group, which offer similar physical properties to existing fluorinated fluids but with shorter atmospheric lifetimes and lower global warming potentials, allowing for their use in various applications such as cleaning, heat transfer, and fire extinguishing.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Object-affected harmful factors
If traditional saturated fluorinated compounds (hydrofluoroethers, hydrofluorocarbons, perfluorocarbons) are used, then high thermal stability, nonflammability, and good solvency are achieved, but high global warming potential and long atmospheric lifetimes result
Solution Approach 1:
The patent introduces unsaturation (double bonds) into the fluorinated compound structure, changing the chemical composition from saturated to unsaturated. This structural parameter change reduces atmospheric lifetime and global warming potential while the fluorinated groups maintain thermal stability and nonflammability properties
Solution Approach 2:
The patent combines fluorinated groups with unsaturated hydrocarbon chains containing amine or ether functional groups, creating composite molecular structures that integrate the beneficial properties of fluorinated compounds (thermal stability, nonflammability) with reduced environmental impact from the unsaturated portion
2Object-affected harmful factors
If unsaturated fluorinated compounds with amine/ether groups are synthesized, then lower global warming potential and shorter atmospheric lifetime are achieved, but complex synthesis procedures are required
Solution Approach 1:
The synthesis is divided into distinct stages: first forming the carbon skeleton with double bonds and functional groups, then introducing fluorine atoms in subsequent steps. This segmentation allows each step to be optimized independently and simplifies the overall manufacturing process
Solution Approach 2:
The patent uses intermediate compounds containing the unsaturated hydrocarbon backbone with amine or ether groups before final fluorination. These intermediaries serve as mediators that simplify the introduction of multiple fluorine atoms and facilitate the synthesis of complex fluorinated structures
Data Source
AI summary
Described herein is an unsaturated fluorinated compound of formula (I) where X is O or N; Y is F or H; Z is F or CF3; and A is F or CF3 wherein when X is O, then n is 1, Y is H, Z is F, A is F, and Rf is a linear or branched perfluorinated alkyl group comprising 1 to 10 carbon atoms and optionally comprising at least one catenated O or N; and when X is N, then n is 2 and each Rf group are (i) independently selected from a linear or branched perfluorinated alkyl group comprising 1 to 8 carbon atoms and optionally comprising at least one catenated O or N; or (ii) bonded together to form a ring structure comprising 4 to 8 carbon atoms and optionally comprising at least one catenated O or N with the proviso that when Z is CF3 then A is F and when A is CF3 then Z is F and methods of making and using the same.