Process for the reduction of RƒC≡CX impurities in fluoroolefins
This disclosure relates to processes which involve: contacting a mixture comprising at least one fluoroolefin and at least one impurity with at least one zeolite to reduce the concentration of the at least one impurity in the mixture; and the at least one zeolite is selected from the group consisting of zeolites having pore opening of at least 4 Angstroms and no more than about 5 Angstroms, zeolites having pore opening of at least about 5 Angstroms and Sanderson electronegativity of no more than about 2.6, and mixtures thereof; provided that the at least one zeolite is not zeolite 4A. This disclosure also relates to processes for making at least one hydrotetrafluoropropene product selected from the group consisting of CF 3 CF═CH 2 , CF 3 CH═CHF, and mixtures thereof; and relates to processes for making at least one hydrochlorotrifluoropropene product selected from the group consisting of CF 3 CCl═CH 2 , CF 3 CH═CHCl, and mixtures thereof.
1. A process comprising:
contacting a mixture comprising at least one fluoroolefin and at least one impurity with at least one zeolite to reduce the concentration of said at least one impurity in said mixture;
wherein said at least one zeolite is selected from the group consisting of zeolite 5A, zeolite 13X, zeolite LSX, zeolite AW-300, and mixtures thereof.
2. The process according to claim 1 wherein the at least one fluoroolefin is a hydrofluoroolefin.
3. The process according to claim 1 wherein the at least one fluoroolefin is a hydrochlorofluoroolefin.
4. The process according to claim 1 wherein the at least one fluoroolefin is CF 3 CF═CH 2 , CF 3 CH═CHF, CF 3 CH═CH 2 , CF 3 CCl═CH 2 , CF 3 CH═CHCl, CF 3 CH═CFCl, CF 3 CH═CF 2 , CF 3 CCl═CHF, CF 3 CF═CHF, CF 3 CF═CHCl, CF 3 CH═CCl 2 , CF 3 CCl═CHCl, or mixtures thereof.
5. The process according to claim 1 wherein the at least one fluoroolefin is CF 3 CF═CH 2 , CF 3 CH═CH 2 , CF 3 CCl═CH 2 , CF 3 CH═CHCl, CF 3 CH═CFCl, CF 3 CH═CF 2 , CF 3 CCl═CHF, CF 3 CF═CHF, CF 3 CF═CHCl, CF 3 CH═CCl 2 , CF 3 CCl═CHCl, or mixtures thereof.
6. The process according to claim 2 wherein the at least one hydrofluoroolefin is CF 3 CF═CH 2 , CF 3 CH═CHF, CF 3 CH═CH 2 , CF 3 CH═CF 2 , CF 3 CF═CHF, or mixtures thereof.
7. The process according to claim 2 wherein the at least one hydrofluoroolefin is CF 3 CF═CH 2 , CF 3 CH═CH 2 , CF 3 CH═CF 2 , CF 3 CF═CHF, or mixtures thereof.
8. The process according to claim 3 wherein the at least one hydrochlorofluoroolefin is CF 3 CCl═CH 2 , CF 3 CH═CHCl, CF 3 CF═CHCl, CF 3 CH═CCl 2 , CF 3 CCl═CHCl, CF 3 CH═CFCl, CF 3 CCl═CHF, or mixtures thereof.
9. The process according to claim 1 wherein the at least one fluoroolefin is CF 3 CF═CH 2 .
10. The process according to claim 1 wherein the at least one fluoroolefin is CF 3 CCl═CH 2 , CF 3 CH═CHCl, or mixtures thereof.
11. The process according to claim 1 wherein the amount of the at least one fluoroolefin is at least 70 wt % of the mixture.
12. The process according to claim 1 wherein the amount of the at least one fluoroolefin is at least 90 wt % of the mixture.
13. A composition formed by the process of claim 1 .
14. A composition comprising:
i. a mixture of at least one fluoroolefin and at least one impurity; and
ii. at least one zeolite selected from the group consisting of zeolite 5A, zeolite 13X, zeolite LSX, zeolite AW-300, and mixtures thereof.
15. The composition according to claim 14 wherein the at least one fluoroolefin is a hydrofluoroolefin.
16. The composition according to claim 14 wherein the at least one fluoroolefin is a hydrochlorofluoroolefin.
17. The composition according to claim 14 wherein the at least one fluoroolefin is CF 3 CF═CH 2 , CF 3 CH═CHF, CF 3 CH═CH 2 , CF 3 CCl═CH 2 , CF 3 CH═CHCl, CF 3 CH═CFCl, CF 3 CH═CF 2 , CF 3 CCl═CHF, CF 3 CF═CHF, CF 3 CF═CHCl, CF 3 CH═CCl 2 , CF 3 CCl═CHCl, or mixtures thereof.
18. The composition according to claim 14 wherein the at least one fluoroolefin is CF 3 CF═CH 2 , CF 3 CH═CH 2 , CF 3 CCl═CH 2 , CF 3 CH═CHCl, CF 3 CH═CFCl, CF 3 CH═CF 2 , CF 3 CCl═CHF, CF 3 CF═CHF, CF 3 CF═CHCl, CF 3 CH═CCl 2 , CF 3 CCl═CHCl, or mixtures thereof.
19. The composition according to claim 15 wherein the at least one hydrofluoroolefin is CF 3 CF═CH 2 , CF 3 CH═CHF, CF 3 CH═CH 2 , CF 3 CH═CF 2 , CF 3 CF═CHF, or mixtures thereof.
20. The composition according to claim 15 wherein the at least one hydrofluoroolefin is CF 3 CF═CH 2 , CF 3 CH═CH 2 , CF 3 CH═CF 2 , CF 3 CF═CHF, or mixtures thereof.
21. The composition according to claim 16 wherein the at least one hydrochlorofluoroolefin is CF 3 CCl═CH 2 , CF 3 CH═CHCl, CF 3 CF═CHCl, CF 3 CH═CCl 2 , CF 3 CCl═CHCl, CF 3 CH═CFCl, CF 3 CCl═CHF, or mixtures thereof.
22. The composition according to claim 14 wherein the at least one fluoroolefin is CF 3 CF═CH 2 .
23. The composition according to claim 14 wherein the at least one fluoroolefin is CF 3 CCl═CH 2 , CF 3 CH═CHCl, or mixtures thereof.
24. The composition according to claim 14 wherein the amount of the at least one fluoroolefin is at least 70 wt % of the mixture.
25. The composition according to claim 14 wherein the amount of the at least one fluoroolefin is at least 90 wt % of the mixture.
26. The composition according to claim 14 wherein the amount of the at least one impurity in the mixture is 300 ppm or less.
27. The composition according to claim 14 wherein the amount of the at least one impurity in the mixture is 200 ppm or less.
28. The composition according to claim 14 wherein the amount of the at least one impurity in the mixture is 100 ppm or less.
29. The composition according to claim 14 wherein the amount of the at least one impurity is at least 0.15% by GC-FID of the mixture.
30. The composition according to claim 14 wherein the amount of the at least one impurity is at least 0.118% by GC-FID of the mixture.