Methods of making a polyfluorinated allyl ether and compounds relating to the methods

Patent metadata

Field	Value
Publication number	US-11292763-B2
Application number	US-201816613900-A
Country	US
Kind code	B2
Filing date	May 17, 2018
Priority date	May 19, 2017
Publication date	Apr 5, 2022
Grant date	Apr 5, 2022

Abstract

A method includes combining first components including at least one of CF2═CF—CF2—OSO2Cl or CF2═CF—CF2—OSO2CF3, a polyfluorinated compound having at least one ketone or carboxylic acid halide, and fluoride ion to provide a compound comprising at least one perfluorinated allyl ether group. A method includes combining second components including B(OSO2Cl)3 and hexafluoropropylene to provide CF2═CF—CF2—OSO2Cl. Another method includes combining second components including M(OSO2CF3)3 and hexafluoropropylene at a temperature above 0° C. to provide CF2═CF—CF2—OSO2CF3, wherein M is Al or B. The compound CF2═CF—CF2—OSO2Cl is also provided.

First claim

What is claimed is:

1. A method of making a compound comprising at least one perfluorinated allyl ether group, the method comprising:
combining first components comprising:
CF 2 ═CF—CF 2 —OSO 2 Cl,

a polyfluorinated compound comprising at least one ketone, carboxylic acid halide, or a combination thereof, and
fluoride ion
to provide the compound comprising at least one perfluorinated allyl ether group.

2. The method of claim 1 , wherein the compound comprising at least one perfluorinated allyl ether group is represented by formula CF 2 ═CFCF 2 (OC n F 2n ) z ORf, wherein each n is independently from 2 to 6, z is 0, 1, or 2, and Rf is a linear or branched perfluoroalkyl group having from 1 to 8 carbon atoms and optionally interrupted by one or more —O— groups.

3. The method of claim 1 , wherein the compound comprising at least one perfluorinated allyl ether group is represented by formula CF 2 ═CF—CF 2 —O—R F —O—CF 2 —CF═CF 2 , wherein R F represents linear or branched perfluoroalkylene or perfluoropolyoxyalkylene or arylene, which may be non-fluorinated or fluorinated.

4. The method of claim 3 , wherein R F represents linear or branched perfluoroalkylene or perfluoropolyoxyalkylene.

5. The method of claim 1 , wherein the polyfluorinated compound is O═CR 3 R 3 , wherein each R 3 is independently a linear or branched perfluoroalkyl group having from 1 to 12 carbon atoms that is optionally terminated by —SO 2 F, —OCF 2 CF═CF 2 , —COF, —CF(CF 3 ) 2 , —CF 2 CO 2 H, —F, —Cl, —Br, —I, —CN, or —CO 2 -alkyl, and optionally interrupted by one or more —O— groups.

6. The method of claim 1 , wherein the polyfluorinated compound is FC(O)(R 1 ) or FC(O)(R 2 ), wherein R 1 is a linear or branched perfluoroalkyl group having from 2 to 12 carbon atoms that is optionally terminated by —SO 2 F, —OCF 2 CF═CF 2 , —COF, —Cl, —Br, —I, or —CO 2 -alkyl, and wherein R 2 is a linear or branched perfluoroalkyl group having from 2 to 14 carbon atoms that is interrupted by one or more —O— groups and optionally terminated by —SO 2 F, —OCF 2 CF═CF 2 , —COF, —Cl, —Br, —I, or —CO 2 -alkyl.

7. The method claim 1 , wherein the fluoride ion is comprised in at least one of sodium fluoride, potassium fluoride, rubidium fluoride, cesium fluoride, or (R) 4 NF, wherein is each R is independently alkyl having from 1 to 6 carbon atoms.

8. The method of claim 1 , further comprising combining second components comprising B(OSO 2 Cl) 3 and hexafluoropropylene to provide CF 2 ═CF—CF 2 —OSO 2 Cl.

9. A method of making CF 2 ═CF—CF 2 —OSO 2 Cl, the method comprising:
combining second components comprising B(OSO 2 Cl) 3 and hexafluoropropylene to provide CF 2 ═CF—CF 2 —OSO 2 Cl.

10. The method of claim 9 , further comprising:
combining third components comprising BCl 3 and ClSO 3 H to provide B(OSO 2 Cl) 3 .

11. A compound represented by formula CF 2 ═CF—CF 2 —OSO 2 Cl.

12. The method of claim 2 , wherein z is 0, and wherein Rf is a linear or branched perfluoroalkyl group having from 1 to 4 carbon atoms.

13. The method of claim 1 , further comprising combining and interpolymerizing the compound comprising at least one perfluorinated allyl ether group with at least one partially fluorinated or perfluorinated ethylenically unsaturated monomer represented by formula R a CF═CR a 2 , wherein each R a is independently fluoro, chloro, bromo, hydrogen, a fluoroalkyl group, alkyl having up to 10 carbon atoms, alkoxy having up to 8 carbon atoms, or aryl having up to 8 carbon atoms to form a fluoropolymer.

14. A method of making a compound comprising at least one perfluorinated allyl ether group, the method comprising:
combining first components comprising:
CF 2 ═CF—CF 2 —OSO 2 CF 3 ,

a polyfluorinated compound comprising at least one carboxylic acid halide, and
fluoride ion
to provide the compound comprising at least one perfluorinated allyl ether group.

15. The method of claim 14 , wherein the compound comprising at least one perfluorinated allyl ether group is represented by formula CF 2 ═CFCF 2 (OC n F 2n ) z ORf, wherein each n is independently from 2 to 6, z is 0, 1, or 2, and Rf is a linear or branched perfluoroalkyl group having from 1 to 8 carbon atoms and optionally interrupted by one or more —O— groups.

16. The method of claim 15 , wherein z is 0, and wherein Rf is a linear or branched perfluoroalkyl group having from 1 to 4 carbon atoms.

17. The method of claim 14 , wherein the compound comprising at least one perfluorinated allyl ether group is represented by formula CF 2 ═CF—CF 2 —O—R F —O—CF 2 —CF═CF 2 , wherein R F represents linear or branched perfluoroalkylene or perfluoropolyoxyalkylene or arylene, which may be non-fluorinated or fluorinated.

18. The method of claim 14 , wherein the polyfluorinated compound comprising at least one carboxylic acid halide is FC(O)(R 1 ) or FC(O)(R 2 ), wherein R 1 is a linear or branched perfluoroalkyl group having from 2 to 12 carbon atoms that is optionally terminated by —SO 2 F, —OCF 2 CF═CF 2 , —COF, —Cl, —Br, —I, or —CO 2 -alkyl, and wherein R 2 is a linear or branched perfluoroalkyl group having from 2 to 14 carbon atoms that is interrupted by one or more —O— groups and optionally terminated by —SO 2 F, —OCF 2 CF═CF 2 , —COF, —Cl, —Br, —I, or —CO 2 -alkyl.

Assignees

• 3M Innovative Properties Co

Inventors

• Hintzer Klaus
• Hirschberg Markus E
• Pajkert Romana
• Röschenthaler Gerd-Volker
• Tverdomed Sergey N

Classifications

• C07C303/26 Primary

  of esters of sulfonic acids · CPC title

• C07C303/24

  of esters of sulfuric acids · CPC title

• C07C305/26

  Halogenosulfates, i.e. monoesters of halogenosulfuric acids · CPC title

• C07C43/126

  having more than one ether bond · CPC title

• C07C41/14

  by exchange of organic parts on the ether-oxygen for other organic parts, e.g. by trans-etherification · CPC title