IP Library Granted Patent US 12,084,412
Granted Patent B2
US 12,084,412 · App. 17/219,390 · Granted Sep 10, 2024

Synthesis of trifluoroacetyl iodide (TFAI) from trifluoroacetyl chloride (TFAC) and hydrogen iodide (HI) in a liquid phase reaction

Inventors: Terris Yang (East Amherst, NY); Haiyou Wang (Amherst, NY)
Assignee: Honeywell International Inc.
C07C51/58B01J19/004B01J21/06B01J21/18B01J29/035B01J27/224B01J2219/00029B01J2219/00033
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Quick Facts
Patent No.
US 12,084,412
App. No.
17/219,390
Granted
Sep 10, 2024
Kind
B2
Abstract

The present disclosure provides a process for making trifluoroacetyl iodide (TFAI) in a liquid phase reaction. Specifically, the present disclosure provides a liquid phase reaction of trifluoroacetyl chloride (TFAC) and hydrogen iodide (HI), with or without a catalyst, to form trifluoroacetyl iodide (TFAI). The reaction may be performed at ambient or elevated temperatures.

Claims (23)

1. A process for producing trifluoroacetyl iodide (TFAI) in a liquid phase reaction, the process comprising:

providing trifluoroacetyl chloride, hydrogen iodide, and an optional catalyst;

reacting the trifluoroacetyl chloride and hydrogen iodide to provide trifluoroacetyl iodide at a temperature from 25° C. to 90° ° C.,

and

wherein the process has a selectivity for trifluoroacetyl iodide that is greater than 90%.

2. The process of claim 1 , wherein in the providing step, the mole ratio of the trifluoroacetyl chloride to the hydrogen iodide is from about 1:1 to about 10:1.

3. The process of claim 1 , wherein in the providing step, a weight ratio of the catalyst to the trifluoroacetyl chloride is from about 0.001:1 to about 0.5:1.

4. The process of claim 1 , wherein the catalyst is selected from the group consisting of silicon carbide, activated carbon, carbon molecular sieves, and combinations thereof.

5. The process of claim 1 , wherein in the reacting step, the trifluoroacetyl chloride, the hydrogen iodide, and the optional catalyst are at a temperature from 35° C. to 60° C.

6. A process for producing trifluoroacetyl iodide (TFAI) in a liquid phase reaction, the process comprising:

mixing trifluoroacetyl chloride, hydrogen iodide, and an optional catalyst; and

heating the trifluoroacetyl chloride, hydrogen iodide to a temperature from 25° C. to 90° C., and an optional catalyst to produce trifluoroacetyl iodide and hydrogen chloride, and

separating the trifluoroacetyl iodide from the hydrogen chloride, trifluoroacetyl chloride, and hydrogen iodide,

wherein the process has a selectivity for trifluoroacetyl iodide that is greater than 90%.

7. The process of claim 6 , wherein the process is a batch process.

8. The process of claim 6 , wherein the catalyst is selected from the group consisting of silicon carbide, activated carbon, carbon molecular sieves, and combinations thereof.

9. The process of claim 6 , wherein in the heating step, the trifluoroacetyl chloride, the hydrogen iodide, and the optional catalyst are at a temperature from 35° C. to 60° C.

10. The process of claim 6 , wherein in the heating step, the trifluoroacetyl chloride, the hydrogen iodide, and the optional catalyst are at a pressure of 5 psig to 500 psig.

11. The process of claim 1 , wherein in the reacting step, the trifluoroacetyl chloride, the hydrogen iodide, and the optional catalyst, are at a temperature from 25° C. to 90° C., and the process results in a greater than 80% conversion of trifluoroacetyl chloride and a greater than 99% selectivity for TFAI.

12. The process of claim 1 , wherein in the reacting step, the trifluoroacetyl chloride, hydrogen iodide, and the optional catalyst, have a residence time from about 0.1 hours to about 5 hours to provide trifluoroacetyl iodide.

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

14. The process of claim 1 , wherein a catalyst is present and where the catalyst is silicon carbide.

15. The process of claim 6 , wherein the process results in a greater than 80% conversion of trifluoroacetyl chloride and a greater than 99% selectivity for TFAI.

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 Oct 6, 2021
From: YANG, TERRIS; WANG, HAIYOU
To: HONEYWELL INTERNATIONAL INC.
Reel/Frame 057713/0288 →
Continuity (2)
Provisional Application 63007220 · Apr 8, 2020
Related Publication 20210317062A1 · Oct 14, 2021