Processes for producing trifluoroiodomethane and trifluoroacetyl iodide

Patent metadata

Field	Value
Publication number	US-12281053-B2
Application number	US-202318534092-A
Country	US
Kind code	B2
Filing date	Dec 8, 2023
Priority date	Aug 24, 2018
Publication date	Apr 22, 2025
Grant date	Apr 22, 2025

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.

First claim

What is claimed is:

1. A gas-phase process for producing trifluoroiodomethane, the process comprising:
providing a reactant stream comprising hydrogen iodide and trifluoroacetyl chloride;
reacting the reactant stream in the presence of a first catalyst at a first reaction temperature from about 25° C. to about 120° C. and at a pressure from atmospheric pressure to 300 psig 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 reactant stream may be in contact with the first catalyst for a contact time from about 0.1 seconds to about 300 seconds.

3. 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.

4. 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.

5. 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.

6. The process of claim 5 , wherein the first catalyst comprises activated carbon or silicon carbide.

7. The process of claim 1 , wherein the reacting the intermediate product stream comprises reacting the intermediate product stream in the presence of a second catalyst.

8. The process of claim 7 , 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.

9. The process of claim 7 , wherein in the step of reacting the intermediate product stream, the intermediate product stream may be in contact with the second catalyst for a contact time from about 0.1 seconds to about 300 seconds.

10. 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.

11. 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.

12. The process of claim 1 , further comprising at least one of 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.

13. The process of claim 1 , wherein in the providing step, the reactant stream comprises less than about 100 ppm by weight of oxygen and the hydrogen iodide comprises less than about 100 ppm by weight of water.

14. The process of claim 1 , wherein in the providing step, the reactant stream comprises less than about 10 ppm by weight of oxygen and the hydrogen iodide comprises less than about 10 ppm by weight of water.

15. The process of claim 1 , wherein in the providing step, a mole ratio of the hydrogen iodide to the trifluoroacetyl halide is from about 0.5:1 to about 2:1.

16. The process of claim 1 , wherein in the providing step, a mole ratio of the hydrogen iodide to the trifluoroacetyl halide is from about 0.7:1 to about 1:1.

17. The process of claim 1 , wherein in the step of reacting the intermediate product stream, the second reaction temperature is from 250° C. to 450° C.

18. The process of claim 1 , wherein in the step of reacting the intermediate product stream, the second reaction temperature is from 300° C. to 400° C.

19. The process of claim 7 , wherein organic compounds in the intermediate product stream comprise, in GC area % of total organic compounds, from 50% to 99% trifluoroacetyl iodide, from 1% to 50% unreacted trifluoroacetyl halide, less than 0.010% trifluoroiodomethane, and less than 8% organic compounds other than trifluoroacetyl iodide, trifluoroacetyl halide, and trifluoroiodomethane.

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

Assignees

• Honeywell Int Inc

Inventors

• Nair Haridasan K
• Matthies Glenn
• Singh Rajiv Ratna
• Yang Terris
• Wang Haiyou
• Hulse Ryan J
• Banavali Rajiv

Classifications

• B01J23/70

  of the iron group metals or copper · CPC title

• B01J23/40

  of the platinum group metals · CPC title

• B01J21/08

  Silica · CPC title

• C07C51/64

  Separation; Purification; Stabilisation; Use of additives · CPC title

• C07C51/60

  by conversion of carboxylic acids or their anhydrides {or esters, lactones, salts} into halides with the same carboxylic acid part · CPC title