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US 9,828,320 B2Granted
Methods of making halogenated fluorinated ether-containing compounds
Assignee3M Innovative Properties Company
InventorsKlaus Hintzer, Markus E. Hirschberg, Kai Helmut Lochhaas, Werner Schwertfeger, Oleg Shyshkov, Arne Thaler
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Abstract
Described herein are three methods for making halogenated fluorinated ether-containing compounds using a fluorinated olefin or hexafluoropropylene oxide.
Claims20
A method of making a halogenated fluorinated ether-containing compound from a fluoroolefin, the method comprising:
- (i) halogenating a difluorosulfuryl peroxide followed by reaction with a first fluoroolefin to form a halogenated fluoroorganyl acid fluoride;
- (ii) reacting the halogenated fluoroorganyl acid fluoride with first compound selected from at least one of:
- (a) a second fluoroolefin in the presence of a halogen containing compound to form the halogenated fluorinated ether-containing compound;
- and
- (b) HFPO to form a corresponding acid fluoride and converting the corresponding acid fluoride into the halogenated fluorinated ether-containing compound.
2 more elements
A method of making a halogenated fluorinated ether-containing compound from a fluoroolefin, the method comprising:
- (i) forming 2,2,3,3-tetrafluoro-3-halogenopropanenitrile using a cyanide containing compound and TFE wherein the forming is selected from:
- a) adding XCN to TFE wherein X is I, Br or Cl;
- and
- b) adding MCN to TFE wherein M is an alkali metal followed by contact with a halogen containing compound;
- (ii) converting the 2,2,3,3-tetrafluoro-3-halogenopropanenitrile to 2,2,3,3-tetrafluoro-3-halogenopropanoyl fluoride;
- (iii) reacting the 2,2,3,3-tetrafluoro-3-halogenopropanoyl fluoride with a first compound selected from at least one of
- (a) a fluoroolefin in the presence of a halogen containing compound to form the halogenated fluorinated ether-containing compound and
- (b) HFPO to form the corresponding acid fluoride and converting the corresponding acid fluoride into a halogenated fluorinated ether-containing compound.
5 more elements
A method of making halogenated fluorinated ether-containing compound from a fluoroolefin, the method comprising:
- (i) reacting a perfluoroorganyl diacid difluoride with a first compound selected from at least one of
- (a) a first fluoroolefin in the presence of a halogen containing compound to form the halogenated fluorinated ether-containing compound;
- and
- (b) HFPO to form the corresponding diacid difluoride and converting the corresponding diacid difluoride into the halogenated fluorinated ether-containing compound.
1 more element
Dependencies are inferred from the claim text.