IP Library Granted Patent US 10,259,760
Granted Patent B2
US 10,259,760 · App. 15/289,546 · Granted Apr 16, 2019

Azeotrope-like composition of 2-chlor0-3,3,3-trifluoropropene (HCFC-1233xf) and hydrogen fluoride (HF)

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Quick Facts
Patent No.
US 10,259,760
App. No.
15/289,546
Granted
Apr 16, 2019
Kind
B2
Abstract

Provided are azeotropic and azeotrope-like compositions of 2-chloro-3,3,3-trifluoropropene (HCFO-1233xf) and hydrogen fluoride (HF). Such azeotropic and azeotrope-like compositions are useful as intermediates in the production of 2,3,3,3-tetrafluoropropene (HFO-1234yf).

Claims (30)

1. An azeotropic or azeotrope-like composition which consists essentially of from about 6.2 mole percent to about 90.7 mole percent hydrogen fluoride and from about 9.3 mole percent to about 93.8 mole percent 2-chloro-3,3,3-trifluoropropene, which composition has a boiling point of from about 0° C. to about 61° C. at a pressure of from about 15 psia to about 107 psia.

2. The composition of claim 1 which consists of hydrogen fluoride and 2-chloro-3,3,3-trifluoropropene.

3. The composition of claim 1 wherein the hydrogen fluoride is present in the amount from about 53.5 mole percent to about 86.7 mole percent.

4. The composition of claim 1 wherein the hydrogen fluoride is present in the amount from about 79.3 mole percent to about 85.3 mole percent.

5. The composition of claim 1 wherein the hydrogen fluoride is present in the amount from about 60 mole percent to about 71 mole percent.

6. The composition of claim 1 wherein the hydrogen fluoride is present in the amount from about 60.2 mole percent to about 71.7 mole percent.

7. The composition of claim 1 wherein the 2-chloro-3,3,3-trifluoropropene is present in the amount from about 13.3 mole percent to about 46.5 mole percent.

8. The composition of claim 1 wherein the 2-chloro-3,3,3-trifluoropropene is present in the amount from about 14.7 mole percent to about 20.7 mole percent.

9. The composition of claim 1 wherein the 2-chloro-3,3,3-trifluoropropene is present in the amount from about 29 mole percent to about 40 mole percent.

10. The composition of claim 1 wherein the 2-chloro-3,3,3-trifluoropropene is present in the amount from about 28.3 mole percent to about 39.8 mole percent.

11. The composition of claim 1 having a boiling point of about 0° C. at a pressure of about 15 psia; or a boiling point of about 25° C. at a pressure of about 38 psia; or a boiling point of about 61° C. at a pressure of about 107 psia.

12. A method of forming an azeotropic or azeotrope-like composition which comprises forming a blend consisting essentially of from about 6.2 mole percent to about 90.7 mole percent hydrogen fluoride and from about 9.3 mole percent to about 93.8 mole percent 2-chloro-3,3,3-trifluoropropene to thereby form an azeotropic or azeotrope-like composition having a boiling point of from about 0° C. to about 61° C. at a pressure of from about 15 psia to about 107 psia.

13. The method of claim 12 wherein the composition consists of hydrogen fluoride and 2-chloro-3,3,3-trifluoropropene.

14. The method of claim 12 wherein the hydrogen fluoride in present in an amount of from about 15 to about 50 weight percent.

15. The method of claim 12 wherein the 2-chloro-3,3,3-trifluoropropene is present in the amount from about 50 to about 85 weight percent.

16. The method of claim 12 wherein the composition has a boiling point of about 0° C. at a pressure of about 15 psia; or a boiling point of from about 25° C. at a pressure of about 38 psia; or a boiling point of about 61° C. at a pressure of about 107 psia.

17. The method of claim 12 further comprising the step of separating 2-chloro-3,3,3-trifluoropropene from an azeotropic or azeotrope-like composition of 2-chloro-3,3,3-trifluoropropene and hydrogen fluoride using pressure swing distillation.

18. The method of claim 12 further comprising the step of feeding the azeotropic or azeotrope-like composition of 2-chloro-3,3,3-trifluoropropene and hydrogen fluoride to a fluorination reactor as a source of hydrogen fluoride.

19. A method for removing 2-chloro-3,3,3-trifluoropropene from a mixture containing 2-chloro-3,3,3-trifluoropropene and at least one impurity, which comprises adding hydrogen fluoride to the mixture in an amount sufficient to form an azeotropic or azeotrope-like composition of the 2-chloro-3,3,3-trifluoropropene and the hydrogen fluoride, and thereafter separating the azeotropic composition from the impurity.

20. The method of claim 19 wherein the impurity does not form an azeotropic mixture with 2-chloro-3,3,3-trifluoropropene, hydrogen fluoride or a mixture of 2-chloro-3,3,3-trifluoropropene and hydrogen fluoride.

21. The method of claim 19 wherein the impurity does form an azeotropic mixture with 2-chloro-3,3,3-trifluoropropene, hydrogen fluoride or a mixture of 2-chloro-3,3,3-trifluoropropene and hydrogen fluoride.

22. The process of claim 19 wherein the impurity comprises a halocarbon.

23. The method of claim 19 wherein the impurity is miscible with 2-chloro-3,3,3-trifluoropropene.

24. The method of claim 19 wherein the impurity comprises one more of 1,1,1,2,3-pentachloropropane; 1,1,2,3-tetrachloropropene; 2,3,3,3-tetrafluoropropene; 2,3-dichloro-3,3-difluoropropene; 1,1,1,2,2-pentafluoropropane and 1,2-dichloro-3,3,3-trifluoropropene.

25. The method of claim 19 wherein the separating is conducted by distillation.

26. The method of claim 19 wherein the azeotropic composition consists essentially of from about 6.2 mole percent to about 90.7 mole percent hydrogen fluoride and from about 9.3 mole percent to about 93.8 mole percent 2-chloro-3,3,3-trifluoropropene.

27. The method of claim 19 wherein the azeotropic composition consists essentially of from about 53.5 mole percent to about 86.7 mole percent hydrogen fluoride and from about 13.3 mole percent to about 46.5 mole percent 2-chloro-3,3,3-trifluoropropene.

28. The method of claim 19 wherein the azeotropic composition consists essentially of from about 79.3 mole percent to about 85.3 mole percent hydrogen fluoride and from about 14.7 mole percent to about 20.7 mole percent 2-chloro-3,3,3-trifluoropropene.

29. The method of claim 19 wherein the azeotropic composition consists essentially of from about 60 mole percent to about 71 mole percent mole percent hydrogen fluoride and from about 29 mole percent to about 40 mole percent 2-chloro-3,3,3-trifluoropropene.

30. The method of claim 19 wherein the azeotropic composition consists essentially of from about 60.2 mole percent to about 71.7 mole percent hydrogen fluoride and from about 28.3 mole percent to about 39.8 mole percent 2-chloro-3,3,3-trifluoropropene.

Assignments (3)
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 27, 2016
From: PHAM, HANG T.; MERKEL, DANIEL C.; POKROVSKI, KONSTANTIN A.; TUNG, HSUEH S.; SINGH, RAJIV R.
To: HONEYWELL INTERNATIONAL INC.
Reel/Frame 040146/0001 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 26, 2016
From: PHAM, HANG T.; MERKEL, DANIEL C.; POKROVSKI, KONSTANTIN A.; TUNG, HSUEH S.
To: HONEYWELL INTERNATIONAL INC.
Reel/Frame 040141/0122 →