IP Library Granted Patent US 8,871,986
Granted Patent B2
US 8,871,986 · App. 11/901,672 · Granted Oct 28, 2014

Catalyst promoters for producing trifluoroiodomethane and pentafluoroiodoethane

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Quick Facts
Patent No.
US 8,871,986
App. No.
11/901,672
Granted
Oct 28, 2014
Kind
B2
Abstract

The present invention provides a process for the preparation of a fluoroiodoalkane compound represented by the formula CF 3 (CF 2 ) n —I, wherein n is 0 or 1. The process includes the step of contacting: (i) a compound represented by the formula CF 3 (CF 2 ) n —Y, wherein Y is selected from H, Cl, Br, and COOH and n is 0 or 1; (ii) a source of iodine; (iii) an alkali or alkaline earth metal salt catalyst supported on a carrier; and (iv) a catalyst promoter for the alkali or alkaline earth metal salt catalyst. The catalyst promoter includes at least one element selected from a transition metal element, a rare earth metal element, a main group element other than the alkali or alkaline earth metal element, any salts thereof, and any combinations thereof. The contacting is carried out at a temperature and pressure and for a length of time sufficient to produce the fluoroiodoalkane compound. The contacting may be carried out in the presence or absence of a solvent and in the presence or absence of oxygen.

Claims (84)

1. A process for the preparation of a fluoroiodoalkane compound represented by the formula:

CF 3 (CF 2 ) n —I

wherein n is 0 or 1;

the process comprising contacting:

(i) a compound represented by the formula:

CF 3 (CF 2 ) n —Y

wherein Y is selected from the group consisting of: H, Cl, and Br;

wherein n is 0 or 1;

(ii) a source of iodine;

(iii) an alkali metal salt catalyst selected from the group consisting of K, Rb and Cs, and

(iv) a catalyst promoter in the range of from 0.01 to 50% by weight of the entire catalyst weight,

at a temperature for a length of time sufficient to produce the fluoroiodoalkane compound; and

wherein the catalyst promoter comprises V 2 O 5 .

2. The process of claim 1 , wherein the reaction is carried out in the presence of oxygen.

3. The process of claim 1 , wherein the reaction is carried out in the absence of oxygen.

4. The process of claim 1 , wherein the catalyst carrier is carbonaceous.

5. The process of claim 1 , wherein the catalyst carrier is non-carbonaceous.

6. The process of claim 1 , wherein the source of iodine is a compound selected from the group consisting of I 2 , HI, ICl, IF 5 , and any combination thereof.

7. The process of claim 6 , wherein the source of iodine is I 2 .

8. The process of claim 1 , wherein the step of contacting is carried out at a temperature from about 300° C. to about 600° C.

9. The process of claim 8 , wherein the step of contacting is carried out at a temperature from about 400° C. to about 550° C.

10. The process of claim 1 , wherein the step of contacting is carried out at a pressure from about 0.1 atm to about 100 atm.

11. The process of claim 10 , wherein the step of contacting is carried out at a pressure from about 0.5 atm to about 5 atm.

12. The process of claim 1 , wherein the step of contacting is carried out for a length of time from about 0.01 seconds to about 300 hours.

13. The process of claim 12 , wherein the step of contacting is carried out for a length of time from about 0.05 seconds to about 10 hours.

14. The process of claim 12 , wherein the step of contacting is carried out for a length of time from about 1 second to about 10 minutes.

15. The process of claim 1 , wherein the process is a batch process.

16. The process of claim 1 , wherein the process is a continuous process.

17. The process of claim 1 , wherein the contacting is carried out in a fixed-bed reactor.

18. The process of claim 1 , wherein the contacting is carried out in a moving-bed reactor.

19. The process of claim 1 , further comprising a diluent selected from the group consisting of a gas, a solvent, and a combination thereof.

20. The process of claim 19 , wherein the diluent is a gas selected from the group consisting of nitrogen, helium, argon and any combination thereof.

21. The process of claim 19 , wherein the diluent is a solvent of a liquid or gaseous fluorocarbon.

22. The process of claim 1 , further comprising at least one step selected from the group consisting of the following:

a) passing the trifluoromethyl iodide through a scrubber containing an aqueous alkali solution;

b) passing the trifluoromethyl iodide through a scrubber containing a drying agent;

c) cooling at a temperature below the boiling temperature of the trifluoromethyl iodide to condense; and

d) isolating the trifluoromethyl iodide from the reaction mixture in substantially pure form.

23. The process of claim 1 , wherein the catalyst is present at 7.5 wt. %.

24. The process of claim 1 , wherein the catalyst promoter is present at 1 wt. %.

25. The process of claim 1 , wherein the catalyst promoter is present at 2 wt. %.

26. The process of claim 1 , wherein the catalyst promoter is present at 5 wt. %.

27. A process for the preparation of a fluoroiodoalkane compound represented by the formula:

CF 3 (CF 2 ) n —I

wherein n is 0 or 1;

the process comprising contacting:

(i) a compound represented by the formula:

CF 3 (CF 2 ) n —Y

wherein Y is selected from the group consisting of: H, Cl, and Br;

wherein n is 0 or 1;

(ii) a source of iodine;

(iii) an alkali metal salt catalyst selected from the group consisting of K, Rb and Cs, and

(iv) a catalyst promoter in the range of from 0.01 to 50% by weight of the entire catalyst weight,

at a temperature for a length of time sufficient to produce the fluoroiodoalkane compound and

wherein the catalyst promoter comprises Sm 2 O 3 .

28. The process of claim 27 , wherein the reaction is carried out in the presence of oxygen.

29. The process of claim 27 , wherein the reaction is carried out in the absence of oxygen.

30. The process of claim 27 , wherein the catalyst carrier is carbonaceous.

31. The process of claim 27 , wherein the catalyst carrier is non-carbonaceous.

32. The process of claim 27 , wherein the source of iodine is a compound selected from the group consisting of I 2 , HI, ICl, IF 5 , and any combination thereof.

33. The process of claim 27 , wherein the source of iodine is I 2 .

34. The process of claim 27 , wherein the step of contacting is carried out at a temperature from about 300° C. to about 600° C.

35. The process of claim 27 , wherein the step of contacting is carried out at a temperature from about 400° C. to about 550° C.

36. The process of claim 27 , wherein the step of contacting is carried out at a pressure from about 0.1 atm to about 100 atm.

37. The process of claim 27 , wherein the step of contacting is carried out at a pressure from about 0.5 atm to about 5 atm.

38. The process of claim 27 , wherein the step of contacting is carried out for a length of time from about 0.01 seconds to about 300 hours.

39. The process of claim 27 , wherein the step of contacting is carried out for a length of time from about 0.05 seconds to about 10 hours.

40. The process of claim 27 , wherein the step of contacting is carried out for a length of time from about 1 second to about 10 minutes.

41. The process of claim 27 , wherein the process is a batch process.

42. The process of claim 27 , wherein the process is a continuous process.

43. The process of claim 27 , wherein the contacting is carried out in a fixed-bed reactor.

44. The process of claim 27 , wherein the contacting is carried out in a moving-bed reactor.

45. The process of claim 27 , further comprising a diluent selected from the group consisting of a gas, a solvent, and a combination thereof.

46. The process of claim 27 , wherein the diluent is a gas selected from the group consisting of nitrogen, helium, argon and any combination thereof.

47. The process of claim 27 , wherein the diluent is a solvent of a liquid or gaseous fluorocarbon.

48. The process of claim 27 , further comprising at least one step selected from the group consisting of the following:

a) passing the trifluoromethyl iodide through a scrubber containing an aqueous alkali solution;

b) passing the trifluoromethyl iodide through a scrubber containing a drying agent;

c) cooling at a temperature below the boiling temperature of the trifluoromethyl iodide to condense; and

d) isolating the trifluoromethyl iodide from the reaction mixture in substantially pure form.

49. The process of claim 27 , wherein the catalyst is present at 7.5 wt. %.

50. The process of claim 27 , wherein the catalyst promoter is present at 1 wt. %.

51. The process of claim 27 , wherein the catalyst promoter is present at 2 wt. %.

52. The process of claim 27 , wherein the catalyst promoter is present at 5 wt. %.

Assignments (2)
SECURITY INTEREST Recorded Jan 12, 2026
From: SOLSTICE ADVANCED MATERIALS US, INC.
To: JPMORGAN CHASE BANK, N.A., AS ADMINISTRATIVE AGENT
Reel/Frame 074569/0260 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 18, 2007
From: TUNG, HSUEH SUNG; YANG, SHUWU
To: HONEYWELL INTERNATIONAL INC.
Reel/Frame 019902/0454 →