IP Library Granted Patent US 11,565,992
Granted Patent B2
US 11,565,992 · App. 17/523,200 · Granted Jan 31, 2023

Methods for separation of azeotrope or azeotrope-like compositions of trifluoroiodomethane (CF

Inventors: Haluk Kopkalli (Staten Island, NY); Joshua Close (Cheektowaga, NY); Pramod K W Harikumar Warrier (Buffalo, NY); Daniel C. Merkel (Orchard Park, NY)
Assignee: Honeywell International Inc.
C07C45/83C07C17/383C07C17/386C07C51/48
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Quick Facts
Patent No.
US 11,565,992
App. No.
17/523,200
Granted
Jan 31, 2023
Kind
B2
Abstract

The present disclosure provides azeotrope or azeotrope-like compositions including trifluoroiodomethane (CF 3 I) and trifluoroacetyl chloride (CF 3 COCl), methods of forming same, and methods of separating, or breaking, the azeotrope or azeotrope-like compositions of trifluoroiodomethane (CF 3 I) and trifluoroacetyl chloride (CF 3 COCl).

Claims (23)

1. A method of breaking an azeotrope or azeotrope-like composition comprising trifluoroiodomethane (CF 3 I) and trifluoroacetyl chloride (CF 3 COCl), comprising:

contacting the azeotrope or azeotrope-like composition with a solvent that selectively absorbs the trifluoroiodomethane (CF 3 I);

extracting the trifluoroiodomethane (CF 3 I) into the solvent to form a first composition comprising the solvent and the trifluoroiodomethane (CF 3 I) and a second composition comprising the trifluoroacetyl chloride (CF 3 COCl); and

separating the first and second compositions.

2. The method of claim 1 , wherein the azeotrope or azeotrope-like composition consists essentially of from about 0.5 wt. % to about 99.0 wt. % trifluoroacetyl chloride (CF 3 COCl) and from about 1.0 wt. % to about 99.5 wt. % trifluoroiodomethane (CF 3 I).

3. The method of claim 1 , wherein the solvent is selected from the group consisting of toluene, mineral oil, and acetonitrile.

4. The method of claim 3 , wherein the solvent comprises toluene.

5. The method of claim 3 , wherein the solvent comprises mineral oil.

6. The method of claim 3 , wherein the solvent comprises acetonitrile.

7. The method of claim 1 , wherein the separating step further comprises extractive distillation.

8. The method of claim 7 , further comprising the additional step, following the separating step, of distilling the first composition.

9. The method of claim 8 , wherein the distillation of the first composition produces a product stream comprising trifluoroiodomethane (CF 3 I).

10. The method of claim 9 , wherein the trifluoroiodomethane (CF 3 I) contains trifluoroacetyl chloride (CF 3 COCl) in an amount of about 1 wt. % or less.

11. A method of separating the components of an azeotrope or azeotrope-like composition comprising trifluoroacetyl chloride (CF 3 COCl) and trifluoroiodomethane (CF 3 I) comprising:

contacting, within an extractive distillation column, the azeotrope or azeotrope-like composition with a solvent that selectively absorbs the trifluoroiodomethane (CF 3 I) to form a first composition including the solvent and trifluoroiodomethane (CF 3 I) and a second composition comprising trifluoroacetyl chloride (CF 3 COCl); and

distilling the first and second compositions to provide a first distillate comprising trifluoroacetyl chloride (CF 3 COCl) and a first bottoms product comprising the solvent and trifluoroiodomethane (CF 3 I).

12. The method of claim 11 , wherein the solvent is selected from the group consisting of toluene, mineral oil, and acetonitrile.

13. The method of claim 12 , wherein the solvent comprises toluene.

14. The method of claim 11 , further comprising, after the distilling step, the additional step of distilling the first bottoms product to produce a second distillate and a second bottoms product.

15. The method of claim 14 , wherein the second distillate comprises a product stream comprising trifluoroiodomethane (CF 3 I).

16. The method of claim 15 , wherein the trifluoroiodomethane (CF 3 I) contains trifluoroacetyl chloride (CF 3 COCl) in an amount of about 1 wt. % or less.

17. The method of claim 12 , wherein the solvent comprises mineral oil.

18. The method of claim 12 , wherein the solvent comprises acetonitrile.

Assignments (3)
NUNC PRO TUNC ASSIGNMENT Recorded Apr 12, 2026
From: HONEYWELL INTERNATIONAL INC.
To: SOLSTICE ADVANCED MATERIALS US, INC.
Reel/Frame 074344/0054 →
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 18, 2022
From: KOPKALLI, HALUK; CLOSE, JOSHUA; HARIKUMAR WARRIER, PRAMOD K W; MERKEL, DANIEL C.
To: HONEYWELL INTERNATIONAL INC.
Reel/Frame 060540/0208 →