IP Library Granted Patent US 10,954,177
Granted Patent B2
US 10,954,177 · App. 16/549,412 · Granted Mar 23, 2021

Processes for producing trifluoroiodomethane and trifluoroacetyl iodide

Inventors: Haridasan K. Nair (Williamsville, NY); Glenn Matthies (Lockport, NY); Rajiv Ratna Singh (Getzville, NY); Terris Yang (East Amherst, NY); Haiyou Wang (Amherst, NY); Ryan J. Hulse (Getzville, NY); Rajiv Banavali (Morristown, NJ)
Assignee: Honeywell International Inc.
C07C17/20B01J27/224C07C17/35C07C19/16
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Quick Facts
Patent No.
US 10,954,177
App. No.
16/549,412
Granted
Mar 23, 2021
Kind
B2
Abstract

The present disclosure provides a process for producing trifluoroiodomethane, the process comprising providing a reactant stream comprising hydrogen iodide and at least one 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 first catalyst at a first reaction temperature from about 25° C. to about 400° C. to produce an intermediate product stream comprising trifluoroacetyl iodide, and reacting the intermediate product stream in the presence of a second catalyst at a second reaction temperature from about 200° C. to about 600° C. to produce a final product stream comprising the trifluoroiodomethane.

Claims (29)

1. A gas-phase process for producing trifluoroiodomethane, the process comprising:

providing a reactant stream comprising hydrogen iodide and at least one 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 first catalyst at a first reaction temperature from about 25° C. to about 180° C. to produce an intermediate product stream comprising trifluoroacetyl iodide; and

reacting the intermediate product stream at a second reaction temperature from about 200° C. to about 600° C. to produce a final product stream comprising the trifluoroiodomethane.

2. The process of claim 1 , wherein in the step of reacting the reactant stream, the first reaction temperature is from about 40° C. to about 120° C.

3. The process of claim 1 , wherein in the step of reacting the reactant stream, the reactant stream may be in contact with the first catalyst for a contact time from about 0.1 seconds to about 300 seconds.

4. The process of claim 1 , wherein in the providing step, the reactant stream comprises less than about 500 ppm by weight of oxygen and the hydrogen iodide comprises less than about 500 ppm by weight of water.

5. 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 10:1.

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

7. The process of claim 1 , wherein in the step of reacting the reactant stream, the first catalyst comprises activated carbon, meso carbon, stainless steel, nickel, nickel-chromium alloy, nickel-chromium-molybdenum alloy, nickel-copper alloy, copper, alumina, platinum, palladium, metal carbides, non-metal carbides or combinations thereof.

8. The process of claim 7 , wherein the first catalyst comprises activated carbon or silicon carbide.

9. The process of claim 1 , wherein the step of reacting the reactant stream is at a pressure from about atmospheric pressure to about 300 psig (2,068 kPaG).

10. The process of claim 1 , wherein in the step of reacting the intermediate product stream, the intermediate product stream may be in contact with a second catalyst for a contact time from about 0.1 seconds to about 300 seconds.

11. The process of claim 10 , wherein in the step of reacting the intermediate product stream, the second catalyst comprises stainless steel, nickel, nickel-chromium alloy, nickel-chromium-molybdenum alloy, nickel-copper alloy, copper, alumina, silicon carbide, platinum, palladium, rhenium, activated carbon, meso carbon or combinations thereof.

12. The process of claim 1 , wherein in the step of reacting the intermediate product stream, the second reaction temperature is from about 250° C. to about 500° C.

13. The process of claim 1 , wherein organic compounds in the intermediate product stream comprise, in GC area % of total organic compounds, from about 10% to about 99% trifluoroacetyl iodide, from about 1% to about 90% unreacted trifluoroacetyl halide, less than about 0.010% trifluoroiodomethane, and less than about 15% organic compounds other than trifluoroacetyl iodide, trifluoroacetyl halide, and trifluoroiodomethane.

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

separating unreacted trifluoroacetyl halide from the intermediate product stream;

returning the separated trifluoroacetyl halide to the reactant stream;

separating unreacted hydrogen iodide from the intermediate product stream;

returning the unreacted hydrogen iodide to the reactant stream;

separating unreacted trifluoroacetyl iodide from the final product stream; and

returning the separated unreacted trifluoroacetyl iodide to the intermediate product stream.

15. A gas-phase process for producing trifluoroacetyl iodide (CF 3 COI), the process comprising:

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

reacting the reactant stream in the presence of a catalyst at a reaction temperature from about 25° C. to about 180° C. to produce a product stream comprising the trifluoroacetyl iodide.

16. The process of claim 15 , wherein in the step of reacting the reactant stream, the first reaction temperature is from about 40° C. to about 120° C.

17. The process of claim 15 , wherein in the step of reacting the reactant stream, the catalyst comprises activated carbon, meso carbon, stainless steel, nickel, nickel-chromium alloy, nickel-chromium-molybdenum alloy, nickel-copper alloy, copper, alumina, platinum, palladium, metal carbides, non-metal carbides or combinations thereof.

18. The process of claim 16 , wherein organic compounds in the product stream comprise, in GC area% of total organic compounds, from about 10% to about 99% trifluoroacetyl iodide, from about 1% to about 90% unreacted trifluoroacetyl halide, less than about 0.010% trifluoroiodomethane, and less than about 15% organic compounds other than trifluoroacetyl iodide, trifluoroacetyl halide, and trifluoroiodomethane.

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.; MATTHIES, GLENN; SINGH, RAJIV RATNA; YANG, TERRIS; WANG, HAIYOU; HULSE, RYAN J.; BANAVALI, RAJIV
To: HONEYWELL INTERNATIONAL INC.
Reel/Frame 050282/0862 →