Methods for preparing halohydrins and methods for preparing epoxides

1. A method of preparing halohydrins comprising exposing (R 1 CHXCH 2 O—) 2 SO 2 to R 2 COOH to produce R 2 COOCH 2 CHXR 1 and hydrolyzing the R 2 COOCH 2 CHXR 1 to produce R 1 CHXCH 2 OH, R 1 and R 2 being a single element or an organic group, wherein R 1 and R 2 are the same or different and X is a halogen.

2. The method of claim 1 wherein the (R 1 CHXCH 2 O—) 2 SO 2 comprises (CF 3 CHXCH 2 O—) 2 SO 2 , the R 2 COOH comprises acetic acid, the R 2 COOCH 2 CHXR 1 comprises CH 3 COOCH 2 CHXCF 3 and the R 1 CHXCH 2 OH comprises CF 3 CHXCH 2 OH.

3. The method of claim 2 wherein the (CF 3 CHXCH 2 O—) 2 SO 2 comprises (CF 3 CHBrCH 2 O—) 2 SO 2 , the CH 3 COOCH 2 CHXCF 3 comprises CH 3 COOCH 2 CHBrCF 3 , and the CF 3 CHXCH 2 OH comprises CF 3 CHBrCH 2 OH.

4. The method of claim 3 wherein the (CF 3 CHBrCH 2 O—) 2 SO 2 is produced by exposing CF 3 CH═CH 2 to Br 2 and sulfuric acid.

5. The method of claim 4 wherein the sulfuric acid is in the form of oleum.

6. The method of claim 5 wherein the exposing comprises combining the CF 3 CH═CH 2 , the oleum, and the Br 2 at a mole ratio of from about 1:1:0.7 to about 1:4:0.8.

7. The method of claim 5 wherein the exposing comprises combining the CF 3 CH═CH 2 , the oleum, and the Br 2 at a mole ratio of at least about 1:2:0.8.

8. The method of claim 5 wherein the Br 2 and oleum are in the form of a Br 2 -oleum mixture.

9. The method of claim 8 wherein the (CF 3 CHBrCH 2 O—) 2 SO 2 is produced by exposing CF 3 CH═CH 2 to a Br 2 -oleum mixture.

10. The method of claim 9 wherein the Br 2 -oleum mixture is prepared from a 20% (wt./wt.) oleum solution.

11. The method of claim 9 wherein the exposing is performed at a temperature of from about 12° C. to about 22° C.

12. The method of claim 1 wherein R 2 COOH comprises acetic acid.

13. The method of claim 1 wherein X is I.

14. The method of claim 1 wherein X is Br.

15. The method of claim 1 wherein X is Cl.

16. The method of claim 1 wherein R 1 is CF 3 —.

17. The method of claim 1 wherein R 1 is H.

18. The method of claim 1 wherein R 1 is F.

19. The method of claim 1 wherein R 2 is CH 3 —.

20. The method of claim 1 wherein the hydrolyzing comprises exposing the R 2 COOCH 2 CHXR 1 to a sulfuric acid solution.

21. The method of claim 20 wherein the sulfuric acid solution comprises at least about 15% (wt./wt.) sulfuric acid.

22. The method of claim 1 further comprising converting the R 1 CHXCH 2 OH to R 1 CHCH 2 (O).

23. The method of claim 22 wherein the R 1 CHCH 2 (O) comprises CF 3 CHCH 2 (O).

24. The method of claim 22 wherein the converting comprises exposing the R 1 CHXCH 2 OH to a basic solution.

25. The method of claim 24 wherein the basic solution comprises at least about 20% (wt./wt.) sodium hydroxide.

26. The method of claim 24 wherein the basic solution comprises from about 40% (wt./wt.) to about 70% (wt./wt.) sodium hydroxide.

27. The method of claim 24 wherein the basic solution comprises from about 50% (wt./wt.) to about 60% (wt./wt.) sodium hydroxide.

28. The method of claim 22 wherein the converting occurs at a temperature of at least about 100° C.

29. The method of claim 22 wherein the converting occurs at a temperature from about 100° C. to about 130° C.

30. A method of preparing a halohydrin comprising exposing a di(perhaloalkyl)haloethyl sulfate to a carboxylic acid compound to produce a (perhaloalkyl)haloethyl alkyl ester and hydrolyzing the (perhaloalkyl)haloethyl alkyl ester to produce the halohydrin.

31. The method of claim 30 wherein the di(perhaloalkyl)haloethyl sulfate comprises (CF 3 CHBrCH 2 O—) 2 SO 2 , the carboxylic acid compound comprises acetic acid, the (perhaloalkyl)haloethyl alkyl ester comprises CH 3 COOCH 2 CHBrCF 3 and the halohydrin comprises CF 3 CHBrCH 2 OH.

32. The method of claim 31 wherein the (CF 3 CHBrCH 2 O—) 2 SO 2 is produced by exposing CF 3 CH═CH 2 to Br 2 and sulfuric acid.

33. The method of claim 32 wherein the sulfuric acid is in the form of oleum.

34. The method of claim 33 wherein the exposing comprises combining the CF 3 CH═CH 2 , the oleum, and the Br 2 at a mole ratio of from about 1:1:0.7 to about 1:4:0.8.

35. The method of claim 33 wherein the exposing comprises combining the CF 3 CH═CH 2 , the oleum, and the Br 2 at a mole ratio of at least about 1:2:0.8.

36. The method of claim 33 wherein the Br 2 and the oleum are in the form of a Br 2 -oleum mixture.

37. The method of claim 36 wherein the Br 2 -oleum mixture is prepared from a 20% (wt./wt.) oleum solution.

38. The method of claim 37 wherein the exposing is performed at a temperature of from about 12° C. to about 22° C.

39. The method of claim 30 wherein the hydrolyzing comprises exposing the (perhaloalkyl)haloethyl alkyl ester to a sulfuric acid solution.

40. The method of claim 39 wherein the sulfuric acid solution comprises at least about 15% (wt./wt.) sulfuric acid.

41. The method of claim 30 further comprising converting the halohydrin to an epoxide.

42. The method of claim 41 wherein the epoxide comprises CF 3 CHCH 2 (O).

43. The method of claim 41 wherein the converting comprises exposing the halohydrin to a basic solution.

44. The method of claim 43 wherein the basic solution comprises at least about 20% (wt./wt.) sodium hydroxide.

45. The method of claim 43 wherein the basic solution comprises from about 40% (wt./wt.) to about 70% (wt./wt.) sodium hydroxide.

46. The method of claim 43 wherein the basic solution comprises from about 50% (wt./wt.) to about 60% (wt./wt.) sodium hydroxide.

47. The method of claim 41 wherein the converting occurs at a temperature of at least about 100° C.

48. The method of claim 41 wherein the converting occurs at a temperature of from about 100° C. to about 130° C.

49. The method of claim 30 wherein the carboxylic acid compound comprises acetic acid.