Fluorine removal from antimony fluorohalide catalyst using chlorocarbons

1. A method of chlorinating an antimony fluorohalide catalyst comprising: contacting an antimony fluorohalide catalyst that contains one or more fluorines with a regenerating agent chosen from 2-chloro-3,3,3-trifluoropropene (1233xf), 1,1,1,3-tetrachloropropane (250th), 2-chloro-1,1,1,2-tetrafluoropropane (244bb), and combinations of two or more of 1233xf, 250fb, and 244bb under conditions effective to exchange at least one fluorine in the antimony fluorohalide catalyst with chlorine.

2. The method of claim 1 wherein the regenerating agent comprises 1233xf.

3. The method of claim 1 wherein the regenerating agent comprises 250fb.

4. The method of claim 1 wherein the regenerating agent comprises 244bb.

5. The method of claim 1 wherein the antimony fluorohalide catalyst comprises at least one of (i) SbF n X 5-n , wherein n is an integer of 1 to 5, and X is a halogen other than fluorine; and (ii) as SbFD m X′ 3-m , wherein m is an integer of 1 to 3, and X′ is a halogen other than fluorine; or mixtures of (i) and (ii).

6. The method of claim 5 wherein the antimony fluorohalide catalyst comprises SbF n X 5-m , wherein n is an integer of 1 to 5, and X is chlorine and the product is a chlorine-containing catalyst.

7. The method of claim 5 wherein the antimony fluorohalide catalyst comprises SbF m X′ 3-m , wherein m is an integer of 1 to 3, and X′ is chlorine.

8. The method of claim 5 wherein the antimony fluorohalide catalyst comprises SbF 3 .

9. The method of claim 5 wherein the antimony fluorohalide catalyst comprises SbF n X 5-n , wherein n is an integer of 1 to 5, and X is chlorine and SbF m X′ 3-m , wherein m is an integer of 1 to 3, and X′ is chlorine.

10. The method of claim 5 wherein the antimony fluorohalide catalyst comprises SbF 5 , SbF 4 Cl, SbF 3 Cl 2 , or mixtures thereof.

11. The method of claim 5 wherein the antimony fluorohalide catalyst comprises SbF 4 Cl and SbF 3 Cl 2 .

12. The method of claim 1 wherein the contacting occurs at a temperature between about 80° C. and about 120° C.

13. The method of claim 1 wherein the molar ratio of the regenerating agent to the antimony fluorohalide catalyst to the agent is between about 1 to about 5.

14. A method of regenerating and recovering a spent antimony fluorohalide catalyst to produce a chlorinated antimony catalyst comprising:

(a) treating a spent antimony fluorohalide catalyst comprising

(i) SbF n X 5-n , wherein n is an integer of 1 to 5, and X is a halogen other than fluorine, or

(ii) SbF m X′ 3-m , wherein m is an integer of 1 to 3, and X′ is a halogen other than fluorine, or mixtures of (i) and (ii),

with a regenerating agent chosen from 2-chloro-3,3,3-trifluoropropene (1233xf), 1,1,1,3-tetrachloropropane (250th), 2-chloro-1,1,1,2-tetrafluoropropane (244bb), and combinations of two or more of 1233xf, 250fb, and 244bb, under conditions effective to produce a chlorinated antimony catalyst; and

(b) recovering the chlorinated antimony catalyst.

15. The method of claim 14 wherein the chlorinated antimony catalyst comprises SbC 5 .

16. The method of claim 14 wherein the chlorinated antimony catalyst comprises SbC 3 .

17. The method of claim 14 wherein the contacting occurs at a temperature between about 80° C. and about 120° C.; and the molar ratio of the regenerating agent to the spent antimony is between about 1 to about 5.

18. A composition comprising:

at least one antimony fluorohalide catalyst selected from the group consisting of

(i) SbF n X 5-n , wherein n is an integer of 1 to 5, and X is a halogen other than fluorine, and

(ii) SbF m X′ 3-m , wherein m is an integer of 1 to 3, and X′ is a halogen other than fluorine, or mixtures of (i) and (ii); and

at least one compound selected from the group consisting of 2-chloro-3,3,3-trifluoropropene (1233xf), 1,1,1,3-tetrachloropropane (250fb), 2-chloro-1,1,1,2-tetrafluoropropane (HCFC-244bb), and combinations of two or more of 1233xf, 250fb, and 244bb.