IP Library Granted Patent US 7,132,578
Granted Patent B1
US 7,132,578 · App. 11/181,311 · Granted Nov 7, 2006

One-step synthesis of CF

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Quick Facts
Patent No.
US 7,132,578
App. No.
11/181,311
Granted
Nov 7, 2006
Kind
B1
Abstract

A process for the preparation of trifluoromethyl iodide is provided. The process includes the step of contacting in a reactor a compound represented by the formula: CF 3 —W and a compound represented by the formula: IF n wherein W can be H, Br, Cl, COOH, COCl, COOCH 3 , COOC 2 H 5 , COCH 3 , COPh, CF 3 , Si(CH 3 ) 3 , SPh, SCH 3 , SSCF 3 , SSPh, SSCH 3 , or SO 2 Cl, wherein n is 1, 3, 5, or 7, and wherein the step of contacting is carried out, at a temperature, pressure and for a length of time sufficient to produce trifluoromethyl iodide. The contacting step can be carried out in the presence or absence of a catalyst and the contacting step can be carried out in the presence or absence of air.

Claims (60)

1. A process for the preparation of trifluoromethyl iodide, comprising the step of:

contacting in a reactor a compound represented by the formula:

CF 3 —W

and a compound represented by the formula:

IF n

wherein W is selected from the group consisting of: H, Br, Cl, COOH, COCl, COOCH 3 , COOC 2 H 5 , COCH 3 , COPh, CF 3 , Si(CH 3 ) 3 , SPh, SCH 3 , SSCF 3 , SSPh, SSCH 3 , and SO 2 Cl;

wherein n is 1, 3, 5, or 7; and

wherein the step of contacting is carried out, at a temperature, pressure and for a length of time sufficient to produce trifluoromethyl iodide.

2. The process of claim 1 , wherein the contacting step is carried out in the presence of a catalyst.

3. The process of claim 1 , wherein the contacting step is carried out in the absence of a catalyst.

4. The process of claim 1 , wherein the contacting step is carried out in the presence of air.

5. The process of claim 1 , wherein the contacting step is carried out in the absence of air.

6. The process of claim 1 , wherein said step of contacting is carried out at a temperature from about 20° C. to about 650° C.

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

8. The process of claim 1 , wherein said step of contacting is carried out for a length of time from about 0.01 sec to about 300 hours.

9. The process of claim 1 , wherein the process proceeds at least in part according to the following equation:

10. The process of claim 1 , wherein the process proceeds at least in part according to the following equation:

11. The process of claim 1 , wherein the process proceeds according to the following equation:

12. The process of claim 1 , wherein the process proceeds according to the following equation:

13. The process of claim 1 , wherein the process proceeds according to the following equation:

14. The process of claim 1 , wherein the process proceeds at least in part according to the following equation:

15. The process of claim 1 , wherein the process proceeds at least in part according to the following equation:

16. The process of claim 1 , wherein the process proceeds at least in part according to the following equation:

CF 3 —COOC 2 H 5 +IF→CF 3 —I+FCOOC 2 H 5   (6b).

17. The process of claim 1 , wherein W is COCH 3 or COPh, IF n is IF, and the process proceeds, with or without O 2 , at least in part according to the following equations:

18. The process of claim 1 , wherein W is CF 3 and IF n is IF, and the process proceeds at least in part according to the following equation:

CF 3 —CF 3 +IF→CF 3 —I+CF 4   (8).

19. The process of claim 1 , wherein W is Si(CH 3 ) 3 and IF n is IF, and the process proceeds at least in part according to the following equation:

CF 3 —Si(CH 3 ) 3 +IF→CF 3 —I+F—Si(CH 3 ) 3   (9).

20. The process of claim 1 , wherein W is SPh or SCH 3 and IF n is IF, and the process proceeds at least in part according to the following equations:

CF 3 —SPh+IF→CF 3 —I+PhSF  (10a)

CF 3 —SCH 3 +IF→CF 3 —I+CH 3 SF  (10b).

21. The process of claim 1 , wherein W is SSCF 3 or SSPh or SSCH 3 and IF n is IF, and the process proceeds, with or without O 2 , at least in part according to the following equations:

CF 3 —S—S—CF 3 +IF+2O 2 →CF 3 —I+CF 4 +2SO 2   (11a)

CF 3 —S—S—CF 3 +IF+2O 2 →CF 3 —I+CF 4 +2SO 2   (11b)

CF 3 —S—S—CF 3 +IF+2O 2 →CF 3 —I+CF 4 +2SO 2   (11c).

22. The process of claim 1 , wherein W is SO 2 Cl and IF n is iodine monofluoride, and the process proceeds at least in part according to the following equation:

CF 3 —SO 2 Cl+IF→CF 3 —I+SO 2 +ClF  (12).

23. The process of claim 1 , wherein W is H, Br, Cl, COOH, COCl, COOCH 3 , COOC 2 H 5 , COCH 3 , COPh, CF 3 , Si(CH 3 ) 3 , SPh, SCH 3 , SSCF 3 , SSPh, SSCH 3 , or SO 2 Cl and IF n is IF 3 , wherein the process proceeds, with or without O 2 , at least in part according to the following equation:

CF 3 —W+IF 3 →CF 3 →I+WF+F 2   (13).

24. The process of claim 1 , wherein W is H, Br, Cl, COOH, COCl, COOCH 3 , COOC 2 H 5 , COCH 3 , COPh, CF 3 , Si(CH 3 ) 3 , SPh, SCH 3 , SSCF 3 , SSPh, SSCH 3 , or SO 2 Cl and IF n is IF 5 , wherein the process proceeds, with or without O 2 , at least in part according to the following equation:

CF 3 —W+IF 5 →CF 3 —I+WF+2F 2   (14).

25. The process of claim 1 , wherein W is H, Br, Cl, COOH, COCl, COOCH 3 , COOC 2 H 5 , COCH 3 , COPh, CF 3 , Si(CH 3 ) 3 , SPh, SCH 3 , SSCF 3 , SSPh, SSCH 3 , or SO 2 Cl and IF n is IF 7 , wherein the process proceeds, with or without O 2 , at least in part according to the following equation:

CF 3 —W+IF 7 →CF 3 —I+WF+3F 2   (15).

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

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

28. The process of claim 1 , wherein the reactor further comprises a diluent selected from the group consisting of a gas, a solvent and a mixture thereof.

29. The process of claim 28 , wherein said gas is selected from the group consisting of: nitrogen, helium, argon and a mixture thereof.

30. The process of claim 28 , wherein said solvent is a liquid fluorocarbon.

31. The process of claim 1 , further comprising the step of:

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

32. The process of claim 1 , further comprising the step of:

passing the trifluoromethyl iodide through a scrubber containing a drying agent.

33. The process of claim 1 , further comprising the step of:

cooling at a temperature below the boiling temperature of the trifluoromethyl iodide to condense.

34. The process of claim 1 , further omprising the step of:

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

35. The process of claim 1 , wherein at least 10 wt % of the reactants are converted to trifluoromethyl iodide.

36. The process of claim 1 , wherein at least 80 wt % of the reactants are converted to trifluoromethyl iodide.

37. The process of claim 1 , wherein at least 95 wt % of the reactants are converted to trifluoromethyl iodide.

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 Jul 14, 2005
From: MUKHOPADHYAY, SUDIP; TUNG, HSUEH SUNG
To: HONEYWELL INTERNATIONAL INC.
Reel/Frame 016785/0303 →