IP Library Granted Patent US 12,398,085
Granted Patent B2
US 12,398,085 · App. 17/774,053 · Granted Aug 26, 2025

Azeotrope or azeotrope-like compositions of 2-chloro-3,3,3-trifluoropropene (HCFO-1233xf) and water

Inventors: Haluk Kopkalli (Staten Island, NY); Daniel C. Merkel (Orchard Park, NY); Hang T. Pham (Amherst, NY)
Assignee: Honeywell International Inc.
C07C17/383B01J23/6445C07C17/42C07C21/04C07C21/18
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Quick Facts
Patent No.
US 12,398,085
App. No.
17/774,053
Granted
Aug 26, 2025
Kind
B2
Abstract

Heterogenous azeotrope or azeotrope-like compositions comprising 2-chloro-3,3,3-trifluoropropene (HFCO-1233xf) and water which may include from about 0.09 wt. % to about 92.69 wt. % 2-chloro-3,3,3-trifluoropropene (HFCO-1233xf) and from about 7.31 wt. % to about 99.91 wt. % water and having a boiling point between about 12.0° C. and about 13.6° C. at a pressure of between about 12.5 psia and about 16.5 psia. The azeotrope or azeotrope-like compositions may be used to separate impurities, including water, from 2-chloro-3,3,3-trifluoropropene (HFCO-1233xf).

Claims (24)

1. A method of producing 2,3,3,3-tetrafluoropropene (HFO-1234yf) comprising:

providing a composition comprising an azeotrope or azeotrope-like composition consisting essentially of effective amounts of 2-chloro-3,3,3-trifluoropropene (HFCO-1233xf) and water;

converting at least some of the 2-chloro-3,3,3-trifluoropropene (HCFO-1233xf) present in the azeotrope or azeotrope-like composition into 2-chloro-1,1,1,2-tetrafluoropropane (HCFC-244bb); and

converting at least some of the 2-chloro-1,1,1,2-tetrafluoropropane (HCFC-244bb) into 2,3,3,3-tetrafluoropropene (HFO-1234yf).

2. The method of claim 1 , wherein the 2-chloro-3,3,3-trifluoropropene (HCFO-1233xf) is separated from the water before being converted into 2-chloro-1, 1, 1,2-tetrafluoropropane (HCFC-244bb).

3. The method of claim 1 , wherein converting at least some of the 2-chloro-3,3,3-trifluoropropene (HCFO-1233xf) into 2-chloro-1,1,1,2-tetrafluoropropane (HCFC-244bb) comprises reacting the 2-chloro-3,3,3-trifluoropropene (HCFO-1233xf) with HF, preferably anhydrous HF, in the presence of a catalyst.

4. The method of claim 3 , wherein the catalyst comprises a metal halide catalyst.

5. The method of claim 4 , wherein the catalyst comprises SbCl 5 .

6. The method of claim 3 , wherein the reaction is carried out at a temperature from 70° C. to 120° C.

7. The method of claim 3 , wherein the reaction is a liquid phase reaction.

8. The method of claim 3 , wherein the reaction is carried out at a pressure from 50 psig to 120 psig.

9. The method of claim 3 , wherein the reaction is carried out in a liquid phase reaction in the presence of SbCl 5 catalyst at a temperature from 70° C. to 120° C. and at a pressure from 50 psig to 120 psig.

10. The method of claim 1 , wherein converting at least some of the 2-chloro-1,1,1,2-tetrafluoropropane (HCFC-244bb) into 2,3,3,3-tetrafluoropropene (HFO-1234yf) comprises reacting the 2-chloro-1,1,1,2-tetrafluoropropane (HCFC-244bb) in a vapor phase reaction.

11. The method of claim 1 , wherein the step of providing an azeotrope or azeotrope-like composition consisting essentially of effective amounts of 2-chloro-3,3,3-trifluoropropene (HFCO-1233xf) and water comprises combining 2-chloro-3,3,3-trifluoropropene (HFCO-1233xf) and water to form an azeotrope or azeotrope-like composition.

12. The method of claim 1 , wherein the step of providing an azeotrope or azeotrope-like composition consisting essentially of effective amounts of 2-chloro-3,3,3-trifluoropropene (HFCO-1233xf) and water comprises modifying the relative amounts of 2-chloro-3,3,3-trifluoropropene (HCFO-1233xf) and water comprises:

adding 2-chloro-3,3,3-trifluoropropene (HCFO-1233xf) to the composition;

adding water to the composition; or

adding both 2-chloro-3,3,3-trifluoropropene (HCFO-1233xf) and water to the composition.

13. The method of claim 1 , wherein the azeotrope or azeotrope-like composition has a boiling point between about 12.0° C. and about 13.6° C. at a pressure of between about 12.5 psia and about 16.5 psia.

14. The method of claim 1 , wherein the azeotrope or azeotrope-like composition consists essentially of from about 0.09 wt. % to about 92.69 wt. % 2-chloro-3,3,3-trifluoropropene (HFCO-1233xf) and from about 7.31 wt. % to about 99.91 wt. % water.

15. The method of claim 1 , wherein the azeotrope or azeotrope-like composition consists essentially of from about 65 wt. % to about 90 wt. % 2-chloro-3,3,3-trifluoropropene (HFCO-1233xf) and from about 10 wt. % to about 35 wt. % water.

16. The method of claim 1 , wherein the azeotrope or azeotrope-like composition consists essentially of from about 65.14 wt. % to about 86.25 wt. % 2-chloro-3,3,3-trifluoropropene (HFCO-1233xf) and from about 13.75 wt. % to about 34.86 wt. % water.

17. The method of claim 4 , wherein the catalyst comprises TiCl 4 .

18. The method of claim 4 , wherein the catalyst comprises SbF 5 .

Assignments (3)
NUNC PRO TUNC ASSIGNMENT Recorded Apr 13, 2026
From: HONEYWELL INTERNATIONAL INC.
To: SOLSTICE ADVANCED MATERIALS US, INC.
Reel/Frame 074351/0018 →
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 May 7, 2025
From: KOPKALLI, HALUK; MERKEL, DANIEL C.; PHAM, HANG T.
To: HONEYWELL INTERNATIONAL INC.
Reel/Frame 071047/0348 →