2-chloro-3,3,3-trifluoropropene (1233XF) compositions and methods for making and using the compositions

Patent metadata

Field	Value
Publication number	US-12319636-B2
Application number	US-202017614314-A
Country	US
Kind code	B2
Filing date	Jun 3, 2020
Priority date	Jun 4, 2019
Publication date	Jun 3, 2025
Grant date	Jun 3, 2025

Abstract

A composition including 2-chloro-3,3,3-trifluoropropene (1233xf), one or more of 2,3-dichloro-1,1,1-trifluoropropane (243db), 1,2-dichloro-3,3,3-trifluoropropene (1223xd), 2,3-dichloro-3,3-difluoropropene (1232xf), 2,2,3-trichloro-1,1,1-trifluoro-propane (233ab), 2,3,3-trichloro-1,1,1-trifluoro-propane (233da), 3,3,3-trifluoropropyne, 1-chloro-3,3,3-trifluoropropyne, 3,3,3-trifluoro-1-propene (1243zf), 1-chloro-3,3,3-trifluoro-1-propene (1233zd), 1-chloro-2,3,3,3-tetrafluoro-1-propene (1224yd), or 2-bromo-3,3,3-trifluoropropene and optionally 1233xf oligomers are disclosed.

First claim

What is claimed is:

1. A composition comprising:
a) 2-chloro-3,3,3-trifluoropropene (1233xf) in an amount at least 94% GC area, 1,2-dichloro-3,3,3-trifluoropropene (1223xd), 2,3-dichloro-3,3-difluoropropene (1232xf); and
b) at least one additional compound selected from the group consisting of 2,3-dichloro-1, 1, 1-trifluoropropane (243db), 2,2,3-trichloro-1,1,1-trifluoro-propane (233ab), 2,3,3-trichloro-1,1,1-trifluoro-propane (233da), 3,3,3-trifluoropropyne, 1-chloro-3,3,3-trifluoropropyne, 3,3,3-trifluoro-1-propene (1243zf), 1-chloro-3,3,3-trifluoro-1-propene (1233zd), 1-chloro-2,3,3,3-tetrafluoro-1-propene (1224yd), 2-bromo-3,3,3-trifluoropropene, and combinations thereof.

2. The composition of claim 1 , wherein b) includes 2,3-dichloro-1,1,1-trifluoropropane (243db).

3. The composition of claim 1 , wherein b) includes 1-chloro-3,3,3-trifluoropropyne.

4. The composition of claim 1 , wherein b) includes 2-bromo-3,3,3-trifluoropropene (1233xfB).

5. The composition of claim 1 , wherein the 1233xf is present in an amount of at least about 97% GC area.

6. A 2-chloro-3,3,3-trifluoropropene (1233xf) composition comprising 94% GC area 1233xf, 1,2-dichloro-3,3,3-trifluropropene (1223xd), 2,2,3-trichloro-1,1,1-trifluoropropane (233ab), and 2,3-dichloro3,3-difluoropropene (1232xf), and produced by the steps of:
contacting 2,3-dichloro-1,1,1-trifluoropropane (243 db), in the liquid phase, with a base at a temperature between about 25° C. to about 75° C. to effect dehydrochlorination to form the 2-chloro-3,3,3-trifluoropropene (1233xf), 2,2,3-tricholoro- 1,1,1-trifluoropropane (233ab), 1,2-dichioro-3,3,3-trifluoropropene (1223xd) and 2,3-dichioro-3,3-difluoropropene (1232xf).

7. The composition of claim 6 , wherein the base includes at least one of sodium carbonate, potassium carbonate, sodium hydroxide, potassium hydroxide, potassium tert-butoxide, calcium oxides, or calcium hydroxide.

8. The composition of claim 6 , wherein the composition additionally includes at least one of 1-chloro-3,3,3-trifluoro-1-propene (1233zd), 2,3-dichloro-1,1,1-trifluoropropane (243 db), 2,3,3-trichloro-1,1,1-trifluoro-propane (233da), 3,3,3-trifluoropropyne, 1-chloro-3,3,3-trifluoropropyne, or 2-bromo-3,3,3-trifluoropropene (1233xfB).

9. A 2-chloro-3,3,3-trifluoropropene (HCFO-1233xf) composition including HCFO-1233xf in excess of 94% GC are and HCFC-233ab produced by the steps of:
contacting 2,3-dichloro-1,1,1-trifluoropropane (243db), in the vapor phase, with a dehydrochlorination catalyst at a temperature between about 325° C. to about 450° C. and pressure sufficient to effect dehydrochlorination to form the 2-chloro-3,3,3-trifluoropropene (1233xf) and HCFC-233ab.

10. The composition of claim 9 , wherein the dehydrochlorination catalyst comprises activated carbon, alumina, chromium oxide, oxides of transition metals, or metal halides.

11. The composition of claim 9 , wherein the composition further includes at least one of 2,3-dichloro-1,1,1-trifluoropropane (243db), 1,2-dichloro-3,3,3-trifluoropropene (1223xd), 2,3-dichloro-3,3-difluoropropene (1232xf), 2,3,3-trichloro-1,1,1-trifluoro-propane (233da), 3,3,3-trifluoropropyne, 1-chloro-3,3,3-trifluoropropyne, or 2-bromo-3,3,3-trifluoropropene (1233xfB).

12. The composition of claim 9 wherein the composition includes at least 95% GC area 1233xf and at least one additional compound selected from the group consisting of 1243zf, 244bb, 1224 isomer 1230xa, 1231xf, 1233zd, 1223xd, 1223za, 1232xf, 243db 3,3,3-trifluoropropyne, 1-chloro-3,3,3-trifluoropropyne, 234bb, 2-bromo-3,3,3-trifluoropropene (1233xfB) and 123.

13. The composition of claim 12 wherein the amount of the at least one additional compound is greater than 0 and less than 1wt. %.

14. A 2-chloro-3,3,3-trifluoropropene (1233xf) composition produced by the steps of:
contacting a compound selected from the group consisting of 1,1,1,2,3-pentachloropropane (HCC-240db), 2,3,3,3-tetrachloropropene (1230xf), 1,1,2,3-tetrachloropropene (HCC-1230xa), 2,3-dichloro-1,1,1-trifluoropropane (243db) and combinations thereof, in the vapor phase, with a carbon supported fluorination catalyst in the presence of hydrogen fluoride at a temperature and pressure sufficient to effect formation of 2-chloro-3,3,3-trifluoropropene (1233xf).

15. The composition of claim 14 , wherein the fluorination catalyst comprises chromium, aluminum, cobalt, manganese, nickel or iron oxides, hydroxides, metal halides, oxyhalides, or inorganic salts thereof.

16. The composition of claim 1 further comprising at least one oligomer.

17. The composition of claim 13 further comprising at least one oligomer.

18. The composition of claim 16 wherein the oligomer has a structure of:

wherein n=0 to 9.

19. The composition of claim 17 wherein the oligomer has a structure of:

wherein n=0 to 9.

20. The composition of claim 16 further comprising at least one solvent capable of at least partially dissolving the oligomer.

21. The composition of claim 17 further comprising at least one solvent capable of at least partially dissolving the oligomer.

22. The composition of claim 20 wherein the solvent comprises at least one member selected from the group consisting of 113a, dichloromethane, acetone, THF, CHCI3, 1233xf, 244bb, CCI4, 114a, 114, 113, 243 db, 250fb, 1230xa, 240 db, 1233zd, 1223xd, 1224 yd, and 253fb.

23. The composition of claim 21 wherein the solvent comprises at least one member selected from the group consisting of 113a, dichloromethane, acetone, THF, CHCI3, 1233xf, 244bb, CCI4, 114a, 114, 113, 243 db, 250fb, 1230xa, 240 db, 1233zd, 1223xd, 1224 yd, and 253fb.

Assignees

• Chemours Co Fc Llc

Inventors

• Sun Xuehui
• Krause Karl Robert
• Jackson Andrew

Classifications

• C07C19/10

  and chlorine · CPC title

• C07C21/18 Primary

  containing fluorine · CPC title

• C07C17/087 Primary

  to unsaturated halogenated hydrocarbons · CPC title

• C07C17/25 Primary

  by splitting-off hydrogen halides from halogenated hydrocarbons · CPC title

• C07C17/206

  the other compound being HX · CPC title