IP Library Granted Patent US 10,752,565
Granted Patent B2
US 10,752,565 · App. 16/549,389 · Granted Aug 25, 2020

Processes for producing trifluoroiodomethane

Inventors: Haridasan K. Nair (Williamsville, NY); Rajiv Banavali (Morristown, NJ); Rajiv Ratna Singh (Getzville, NY)
Assignee: Honeywell International Inc.
C07C17/087B01J21/18C07C17/363C07C19/16C07C17/383
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Quick Facts
Patent No.
US 10,752,565
App. No.
16/549,389
Granted
Aug 25, 2020
Kind
B2
Abstract

The present disclosure provides a gas-phase process for producing trifluoroiodomethane, the process comprising providing a reactant stream comprising hydrogen iodide and trifluoroacetyl halide selected from the group consisting of trifluoroacetyl chloride, trifluoroacetyl fluoride, trifluoroacetyl bromide, and combinations thereof, and reacting the reactant stream in the presence of a catalyst at a temperature from about 200° C. to about 600° C. to produce a product stream comprising the trifluoroiodomethane.

Claims (35)

1. A gas-phase process for producing trifluoroiodomethane (CF 3 I), the process comprising:

providing a reactant stream comprising hydrogen iodide and trifluoroacetyl halide selected from the group consisting of trifluoroacetyl chloride, trifluoroacetyl fluoride, trifluoroacetyl bromide, and combinations thereof, the reactant stream comprising less than about 500 ppm by volume of oxygen; and

reacting the reactant stream in the presence of a catalyst at a reaction temperature from about 200° C. to about 600° C. to produce a product stream comprising the trifluoroiodomethane, unreacted hydrogen iodide and unreacted trifluoroacetyl halide.

2. The process of claim 1 , wherein in the providing step, the hydrogen iodide comprises less than about 100 ppm by weight of water.

3. The process of claim 1 , wherein in the providing step, a mole ratio of the hydrogen iodide to the trifluoroacetyl halide is from about 0.1:1 to about 2:1.

4. The process of claim 1 , wherein in the providing step, the trifluoroacetyl halide comprises trifluoroacetyl chloride.

5. The process of claim 1 , wherein in the reacting step, a contact time of the reactant stream with the catalyst is from about 0.5 second to about 60 seconds.

6. The process of claim 5 , wherein in the reacting step, the contact time of the reactant stream with the catalyst is from about 20 seconds to about 40 seconds.

7. The process of claim 1 , wherein in the reacting step, the catalyst comprises an activated carbon catalyst, a meso carbon catalyst, or any combination thereof.

8. The process of claim 7 , wherein in the reacting step, the catalyst consists essentially of at least one catalyst selected from the group consisting of an activated carbon catalyst and a meso carbon catalyst.

9. The process of claim 1 , wherein in the reacting step, the reaction temperature is from about 370° C. to about 390° C., and in the providing step, the trifluoroacetyl halide consists essentially of trifluoroacetyl chloride, and a mole ratio of the hydrogen iodide to the trifluoroacetyl chloride is from about 0.9:1 to about 1.1:1.

10. The process of claim 9 , wherein in the providing step, the reactant stream comprising less than about 10 ppm by volume of oxygen.

11. The process of claim 1 , wherein the product stream further comprises trifluoroacetyl iodide, and wherein the organic compounds in the product stream consist of, in GC area % of total organic compounds, from about 70% to about 99% trifluoroiodomethane, from about 1% to about 30% unreacted trifluoroacetyl halide, less than about 5% trifluoroacetyl iodide, and less than about 5% organic compounds other than trifluoroiodomethane, trifluoroacetyl halide, and trifluoroacetyl iodide.

12. The process of claim 1 , further comprising additional steps of:

separating the unreacted trifluoroacetyl halide from the product stream; and

returning the separated unreacted trifluoroacetyl halide to the reactant stream.

13. The process of claim 1 , wherein the product stream further comprises trifluoroacetyl iodide, the process further comprising an additional step of separating the trifluoroacetyl iodide from the product stream and returning the separated trifluoroacetyl iodide to the reactant stream.

14. The process of claim 1 , further comprising an additional step of separating unreacted hydrogen iodide from the product stream and returning the unreacted hydrogen iodide to the reactant stream.

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

16. The process of claim 1 , wherein in the providing step, the reactant stream comprising less than about 100 ppm by volume of oxygen.

17. The process of claim 16 , wherein in the providing step, the reactant stream comprising less than about 50 ppm by volume of oxygen.

18. The process of claim 17 , wherein in the providing step, the reactant stream comprising less than about 10 ppm by volume of oxygen.

19. The process of claim 18 , wherein in the providing step, the reactant stream comprising less than about 1 ppm by volume of oxygen.

20. A gas-phase process for producing trifluoroiodomethane (CF 3 I), the process comprising:

providing a reactant stream comprising hydrogen iodide and trifluoroacetyl halide selected from the group consisting of trifluoroacetyl chloride, trifluoroacetyl fluoride, trifluoroacetyl bromide, and combinations thereof;

heating the reactant stream to a temperature from about 80° C. to about 120° C. before reacting the reactant stream in the presence of the catalyst; and

reacting the reactant stream in the presence of a catalyst at a reaction temperature from about 200° C. to about 600° C. to produce a product stream comprising the trifluoroiodomethane.

21. The process of claim 20 , wherein in the providing step, the trifluoroacetyl halide consists essentially of trifluoroacetyl chloride, and a mole ratio of the hydrogen iodide to the trifluoroacetyl chloride is from about 0.9:1 to about 1.1:1; in the heating step, the reactant stream is heated to a temperature from about 90° C. to about 110° C. before reacting the reactant stream in the presence of the catalyst; and in the reacting step, the reaction temperature is from about 370° C. to about 390° C.

22. The process of claim 21 , wherein in the reacting step, the catalyst consists essentially of at least one catalyst selected from the group consisting of an activated carbon catalyst and a meso carbon catalyst.

23. A gas-phase process for producing trifluoroiodomethane (CF 3 I), the process comprising:

providing a reactant stream comprising hydrogen iodide and trifluoroacetyl halide selected from the group consisting of trifluoroacetyl chloride, trifluoroacetyl fluoride, trifluoroacetyl bromide, and combinations thereof;

reacting the reactant stream in the presence of a catalyst at a reaction temperature from about 200° C. to about 600° C. to produce a product stream comprising the trifluoroiodomethane, hydrohalic acid and carbon monoxide; and

separating hydrohalic acid and carbon monoxide from the product stream.

24. The process of claim 14 , wherein in the providing step, the trifluoroacetyl halide consists essentially of trifluoroacetyl chloride, and a mole ratio of the hydrogen iodide to the trifluoroacetyl chloride is from about 0.9:1 to about 1.1:1; and in the reacting step, the reaction temperature is from about 370° C. to about 390° C.

25. The process of claim 24 , wherein in the reacting step, the catalyst consists essentially of at least one catalyst selected from the group consisting of an activated carbon catalyst and a meso carbon catalyst.

Assignments (3)
NUNC PRO TUNC ASSIGNMENT Recorded Apr 12, 2026
From: HONEYWELL INTERNATIONAL INC.
To: SOLSTICE ADVANCED MATERIALS US, INC.
Reel/Frame 074343/0989 →
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 5, 2019
From: NAIR, HARIDASAN K.; BANAVALI, RAJIV; SINGH, RAJIV RATNA
To: HONEYWELL INTERNATIONAL INC.
Reel/Frame 050282/0722 →
Continuity (2)
Provisional Application 62722553 · Aug 24, 2018
Related Publication 20200062678A1 · Feb 27, 2020
Cited By (1)
US 12,281,053