Fluorine containing vinyl ethers
AssigneesDyneon LLC, 3M Innovative Properties Company
InventorsAllan T. Worm, George G. I. Moore, Miguel A. Guerra, Werner Schwertfeger, Klaus Hintzer, Zai-Ming Qiu, Erik D. Hare
Life of this patent
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Abstract
The present invention describes a novel process for the preparation of perfluorovinyl ethers. The process involves providing a hydrocarbon precursor that may be partially halogenated, fluorinating the precursor to provide a perfluorinated intermediate, and converting the perfluorinated intermediate to the desired perfluorinated ether. Novel perfluorovinyl ethers are also provided.
Claims10
A process for the preparation of a perfluorinated vinyl ether of the formula CF2═CF—O—Rf wherein Rf is a linear, branched or cyclic perfluorinated aliphatic group that contains at least one oxygen atom, the process comprising the steps of
- a) providing a hydrocarbon precursor comprising at least one 2-alkoxy propionate moiety, derivative or equivalent that may be partially halogenated;
- b) fluorinating the hydrocarbon precursor to provide a perfluorinated intermediate;
- and
- c) converting the perfluorinated intermediate to its corresponding perfluorinated acid metal salt, and
- d) converting the perfluorinated acid metal salt to its corresponding perfluorovinyl ether.
A process for the preparation of a perfluorinated vinyl ether of the formula CF2═CF—O—Rf wherein Rf is a linear, branched or cyclic perfluorinated aliphatic group that my contain oxygen atoms, the process comprising the steps of
- a) providing a hydrocarbon precursor comprising at least one 2-alkoxy propionate moiety, derivative or equivalent that may be partially halogenated wherein the hydrocarbon precursor has the formula
- RhOCF(CF3)—COOXhh,
- wherein Xhh is —OC(O)CF(CF3)ORh and wherein Rh is a C1-C20 alkyl or aromatic group, which may be linear, branched, cyclic and which may contain additional ether linkages;
- b) fluorinating the hydrocarbon precursor to provide a perfluorinated intermediate;
- and
- c) converting the perfluorinated intermediate to its corresponding perfluorinated acid metal salt, and
- d) converting the perfluorinated acid metal salt to its corresponding perfluorovinyl ether.
A perfluorovinyl ether having the formula RfOCF2OCF═CF2 wherein Rf is a linear, branched or cyclic perfluorinated aliphatic group that may contain oxygen atoms forming additional ether linkages and that does not contain any sites of terminal unsaturation.
A perfluorovinyl ether according to claim 9 wherein Rf is —CF3.
A perfluorovinyl ether according to claim 9 wherein Rf is —CF2CF3.
A process for the preparation of a perfluorinated vinyl ether of the formula CF2═CF—O—Rf wherein Rf is a linear, branched or cyclic perfluorinated aliphatic group that may contain oxygen atoms, the process comprising the steps of
- a) providing a hydrocarbon precursor comprising at least one 2-alkoxy propionate moiety, derivative or equivalent that may be partially halogenated wherein the hydrocarbon precursor is selected from the group consisting of
- R′h(OCH(CH3)C(O)Xh)2 (i)
- wherein R′h is a divalent, C1-C20 alkyl or aromatic group, which may contain additional ether linkages, Xh is selected from the group consisting of Rh, lower alkoxy, OC(O)CH(CH3)ORh, —F, and —Cl, wherein Rh is a monovalent C1-C20 alkyl or aromatic group, which may be linear, branched, or cyclic and which may contain additional ether linkages, or
- (ii) a reaction product of a fluorinated olefin and an ester of lactic acid;
- b) fluorinating the hydrocarbon precursor to provide a perfluorinated intermediate;
- c) converting the perfluorinated intermediate to its corresponding perfluorinated acid metal salt;
- and
- d) converting the perfluorinated acid metal salt to its corresponding perfluorovinyl ether.
Dependencies are inferred from the claim text.