Methods of making a polyfluorinated allyl ether and compounds relating to the methods
A method includes combining first components including at least one of CF 2 ═CF—CF 2 —OSO 2 Cl or CF 2 ═CF—CF 2 —OSO 2 CF 3 , 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(OSO 2 Cl) 3 and hexafluoropropylene to provide CF 2 ═CF—CF 2 —OSO 2 Cl. Another method includes combining second components including M(OSO 2 CF 3 ) 3 and hexafluoropropylene at a temperature above 0° C. to provide CF 2 ═CF—CF 2 —OSO 2 CF 3 , wherein M is Al or B. The compound CF 2 ═CF—CF 2 —OSO 2 Cl is also provided.
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.