Claims
- 1. A method of making a composition comprising a perfluorinated peroxide of the formula RfC(O)OOC(O)Rf, the method comprising combining a perfluorinated anhydride of the formula Rf(O)OC(O)Rf with hydrogen peroxide and a catalytic amount of a salt, a metal oxide, a metal hydroxide, a metal alcoholate, or a combination thereof, to form the composition comprising the perfluorinated peroxide of the formula RfC(O)OOC(O)Rf, wherein each Rf group is independently a perfluorinated aromatic or aliphatic group, or combinations thereof, optionally including oxygen atoms.
- 2. The method of claim 1 wherein the perfluorinated anhydride, the hydrogen peroxide, and the salt, metal oxide, metal hydroxide, metal alcoholate, or combination thereof form a single phase system.
- 3. The method of claim 1 wherein the perfluorinated peroxide is formed in a yield of at least about 80% based on the amount of active oxygen.
- 4. The method of claim 3 wherein the perfluorinated peroxide is formed in a yield of at least about 90% based on the amount of active oxygen.
- 5. The method of claim 1 wherein the hydrogen peroxide is added as an aqueous solution.
- 6. The method of claim 5 wherein the composition comprising the perfluorinated peroxide further comprises a perfluorinated acid.
- 7. The method of claim 6 wherein the acid is trifluoroacetic acid.
- 8. The method of claim 1 wherein each Rf group is independently a perfluorinated aliphatic group optionally including oxygen atoms.
- 9. The method of claim 8 wherein each Rf group is independently a CnF2n+1 group, wherein n is 1-10.
- 10. The method of claim 1 wherein the composition comprising the perfluorinated peroxide is used as produced.
- 11. The method of claim 1 wherein the salt is a source of a basic anion.
- 12. The method of claim II wherein the salt is an inorganic salt.
- 13. The method of claim 12 wherein the salt comprises an anion selected from the group consisting of a sulfate, nitrate, halide, phosphate, silicate, borate, and a combination thereof.
- 14. The method of claim 11 wherein the anion of the salt is an organic anion.
- 15. The method of claim 14 wherein the organic anion is a carboxylate.
- 16. The method of claim 15 wherein the carboxylate is a propionate, an acetate, a butyrate, an iso-butyrate, or a combination thereof.
- 17. The method of claim 16 wherein the acetate is trifluoroacetate.
- 18. The method of claim 16 wherein the carboxylate is perfluorocarboxylate.
- 19. The method of claim 11 wherein the salt includes a Group IA, Group IIA, or Group IIIA cation.
- 20. The method of claim 11 wherein the salt includes a cation selected from the group consisting of lithium, sodium, potassium, calcium, barium, cesium, strontium, magnesium, aluminum, and combinations thereof.
- 21. The method of claim 1 wherein the salt is used in an amount of at least about 0.0001 mole % to less than 2.5 mole %, based on moles of hydrogen peroxide.
- 22. The method of claim 1 wherein the perfluorinated anhydride, the hydrogen peroxide, and the salt, metal oxide, metal hydroxide, metal alcoholate, or combination thereof are combined at a temperature of about −45° C. to about 40° C.
- 23. A method of making a composition comprising a perfluorinated peroxide of the formula RfC(O)OOC(O)Rf, the method comprising combining a perfluorinated anhydride of the formula RfC(O)OC(O)Rf with hydrogen peroxide and a non-carbonate salt, a metal oxide, a metal hydroxide, a metal alcoholate, or a combination thereof, to form the composition comprising the perfluorinated peroxide of the formula RfC(O)OOC(O)Rf, wherein each Rf group is independently a perfluorinated aromatic or aliphatic group, or combinations thereof, optionally including oxygen atoms.
- 24. The method of claim 23 wherein the non-carbonate salt includes a cation selected from the group consisting of lithium, sodium, potassium, calcium, barium, cesium, strontium, magnesium, aluminum, and combinations thereof.
- 25. The method of claim 23 wherein the non-carbonate salt includes an anion selected from the group consisting of a sulfate, nitrate, halide, phosphate, silicate, borate, and combination thereof.
- 26. The method of claim 23 wherein the anion of the non-carbonate salt is an organic anion.
- 27. The method of claim 26 wherein the organic anion is a carboxylate.
- 28. The method of claim 27 wherein the carboxylate is a propionate, an acetate, a butyrate, an iso-butyrate, or a combination thereof.
- 29. The method of claim 28 wherein the acetate is trifluoroacetate.
- 30. The method of claim 28 wherein the carboxylate is perfluorocarboxylate.
- 31. A method of making a non-aqueous composition comprising a perfluorinated peroxide of the formula RfC(O)OOC(O)Rf, the method comprising combining a perfluorinated anhydride of the formula RfC(O)OC(O)Rf with hydrogen peroxide and a salt, a metal oxide, a metal hydroxide, a metal alcoholate, or a combination thereof, to form the non-aqueous composition comprising the perfluorinated peroxide of the formula RfC(O)OOC(O)Rf, wherein each Rf group is independently a perfluorinated aromatic or aliphatic group, or combinations thereof, optionally including oxygen atoms.
- 32. A method of making a composition comprising a perfluorinated peroxide of the formula RfC(O)OOC(O)Rf, the method comprising combining a perfluorinated anhydride of the formula RfC(O)OC(O)Rf with a perfluorinated peracid, a perfluorinated acid, and a salt, a metal oxide, a metal hydroxide, a metal alcoholate, or a combination thereof, to form the composition comprising the perfluorinated peroxide of the formula RfC(O)OOC(O)Rf, wherein each Rf group is independently a perfluorinated aromatic or aliphatic group, or combinations thereof, optionally including oxygen atoms.
- 33. A method of fluorinating an organic compound comprising:
combining a perfluorinated anhydride of the formula RfC(O)OC(O)Rf with hydrogen peroxide and a catalytic amount of a salt to form a composition comprising a perfluorinated peroxide of the formula RfC(O)OOC(O)Rf, wherein each Rf group is independently a perfluorinated aromatic or aliphatic group, or combinations thereof, optionally including oxygen atoms; and combining the composition comprising the perfluorinated peroxide with an organic compound to fluorinate the organic compound.
- 34. The method of claim 33 wherein the acid has been removed from the composition comprising the perfluorinated peroxide prior to combining the composition with the organic compound.
- 35. The method of claim 33 wherein the organic compound is a polymerizable compound.
- 36. The method of claim 35 wherein fluorinating the organic compound initiates a polymerization reaction of the organic compound.
- 37. The method of claim 33 wherein fluorinating the organic compound provides a perfluorinated organic compound.
- 38. A method of fluorinating an organic compound comprising:
combining a composition comprising a perfluorinated peroxide in a perfluorinated acid with an organic compound to fluorinate the organic compound.
- 39. A method of fluorinating an organic compound comprising:
combining a perfluorinated anhydride of the formula RfC(O)OC(O)Rf with a perfluorinated peracid, a perfluorinated acid, and a salt, a metal oxide, a metal hydroxide, a metal alcoholate, or a combination thereof, to form the composition comprising the perfluorinated peroxide of the formula RfC(O)OOC(O)Rf, wherein each Rf group is independently a perfluorinated aromatic or aliphatic group, or combinations thereof, optionally including oxygen atoms; and combining the composition comprising the perfluorinated peroxide with an organic compound to fluorinate the organic compound.
- 40. A peroxide of the formula RC(O)OOC(O)Rf, wherein the R group is a non-perfluorinated aromatic or aliphatic group, or combinations thereof, optionally including oxygen atoms, and the Rf group is a perfluorinated aromatic or aliphatic group, or combinations thereof, optionally including oxygen atoms, wherein the R and Rf groups each independently have 1-20 carbon atoms, at least one of which has at least 2 carbon atoms.
- 41. The peroxide of claim 40 wherein Rf group is independently a perfluorinated aliphatic group optionally including oxygen atoms.
- 42. The peroxide of claim 41 wherein the Rf group is independently a CnF2n+1 group, wherein n is 2-10.
- 43. The peroxide of claim 40 wherein the R group is independently an aliphatic group optionally including oxygen atoms.
- 44. The peroxide of claim 43 wherein the R group is a CnH2n+1 group, wherein n is 2-10.
- 45. A method of making a peroxide of the formula RC(O)OOC(O)Rf, the method comprising: combining a carboxylic acid of the formula RC(O)OH with a perfluorocarboxylic peracid of the formula RfC(O)OOH in the presence of a perfluorocarboxylic anhydride of the formula RfC(O)OC(O)Rf; wherein the R group is a non-perfluorinated aromatic or aliphatic group, or combinations thereof, optionally including oxygen atoms, and the Rf group is a perfluorinated aromatic or aliphatic group, or combinations thereof, optionally including oxygen atoms, wherein the R and Rf groups each independently have 1-20 carbon atoms, at least one of which has at least 2 carbon atoms.
- 46. A method of making a peroxide of the formula RC(O)OOC(O)Rf, the method comprising: combining a percarboxylic acid of the formula RC(O)OOH with a perfluorocarboxylic anhydride of the formula RfC(O)OC(O)Rf; wherein the R group is a non-perfluorinated aromatic or aliphatic group, or combinations thereof, optionally including oxygen atoms, and the Rf group is a perfluorinated aromatic or aliphatic group, or combinations thereof, optionally including oxygen atoms, wherein the R and Rf groups each independently have 1-20 carbon atoms, at least one of which has at least 2 carbon atoms.
CROSS-REFERENCE TO RELATED APPLICATIONS
[0001] The present application claims priority to U.S. patent application Ser. No. 60/294,820, filed on Jun. 5, 2001, which is incorporated herein by reference.
Provisional Applications (1)
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Number |
Date |
Country |
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60294820 |
Jun 2001 |
US |