Compositions including olefin and hydrofluoroalkane

Patent metadata

Field	Value
Publication number	US-12006274-B2
Application number	US-202218052391-A
Country	US
Kind code	B2
Filing date	Nov 3, 2022
Priority date	May 21, 2015
Publication date	Jun 11, 2024
Grant date	Jun 11, 2024

Abstract

A method hydrofluorinates an olefin of the formula: RCX=CYZ to produce a hydrofluoroalkane of formula RCXFCHYZ or RCXHCFYZ, where X, Y, and Z are independently the same or different and are selected from the group consisting of H, F, Cl, Br, and C 1 -C 6 alkyl which is partially or fully substituted with chloro or fluoro or bromo; and R is a C 1 -C 6 alkyl which is unsubstituted or substituted with chloro or fluoro or bromo. The method includes reacting the olefin with HF in the vapor phase, in the presence of SbF 5 , at a temperature ranging from about −30° C. to about 65° C. and compositions formed by the process.

First claim

What is claimed is:

1. A composition comprising:
a mixture comprising HF, SbF 5 , olefin, and a hydrofluoroalkane;
wherein the olefin and the hydrofluoroalkane are selected from:
a) the olefin is (Z)-1-chloro-3,3,3-trifluoropropene or (E)-1-chloro-3,3,3-trifluoropropene and the hydrofluoroalkane is 3-chloro-1,1,13-tetrafluoropropane;
b) the olefin is 1-chloro-2,3,3,3-tetrafluoropropene and the hydrofluoroalkane is 1,1,1,2,2-pentafluoro-3-chloropropane and 1,1,1,2,3-pentafluoro-3-chloropropane;
c) the olefin is 2,3,3,3-tetrafluoropropene and the hydrofluoroalkane is 1,1,1,2,2-pentafluoropropane; and
d) the olefin is 1,3,3,3-tetrafluoropropene and the hydrofluoroalkane is 1,1,1,3,3-pentafluoropropane; and
wherein the SbF 5 is present in an amount in the range of about 2% to about 30%, by weight of the mixture.

2. The composition of claim 1 , wherein the SbF 5 is present in an amount in the range of about 3% to about 15%, by weight of the mixture.

3. The composition of claim 2 , wherein the SbF 5 is present in an amount in the range of about 10% to about 11%, by weight of the mixture.

4. The composition of claim 3 , wherein the composition is a liquid.

5. The composition of claim 1 , wherein the mole ratio of HF to the olefin is in the range of from 1 to 10.

6. The composition of claim 5 , wherein the mole ratio of HF to the olefin is in the range of from 1 to 5.

7. The composition of claim 1 , wherein the olefin is (Z)-1-chloro-33,3-trifluoropropene or (E)-1-chloro-3,3,3-trifluoropropene and the hydrofluoroalkane is 3-chloro-1,1,1,3-tetrafluoropropane.

8. The composition of claim 1 , wherein the olefin is 1-chloro-2,3,3,3-tetrafluoropropene and the hydrofluoroalkane is 1,1,1,2,2-pentafluoro-3-chloropropane and 1,1,1,2,3-pentafluoro-3-chloropropane.

9. The composition of claim 1 , wherein the olefin is 2,3,3,3-tetrafluoropropene and the hydrofluoroalkane is 1,1,1,2,2-pentafluoropropane.

10. The composition of claim 1 , wherein the olefin is 1,3,3,3-tetrafluoropropene and the hydrofluoroalkane is 1,1,1,3,3-pentafluoropropane.

11. The composition of claim 7 , wherein the olefin is (Z)-1-chloro-3,3,3-trifluoropropene.

12. The composition of claim 7 , wherein the olefin is (E)-1-chloro-3,3,3-trifluoropropene.

13. The composition of claim 7 , wherein the SbF 5 is present in an amount in the range of about 3% to about 15%, by weight of the mixture.

14. The composition of claim 13 , wherein the SbF 5 is present in an amount in the range of about 10% to about 11%, by weight of the mixture.

15. The composition of claim 8 , wherein the SbF 5 is present in an amount in the range of about 3% to about 15%, by weight of the mixture.

16. The composition of claim 15 , wherein the SbF 5 is present in an amount in the range of about 10% to about 11%, by weight of the mixture.

17. The composition of claim 9 , wherein the SbF 5 is present in an amount in the range of about 3% to about 15%, by weight of the mixture.

18. The composition of claim 17 , wherein the SbF 5 is present in an amount in the range of about 10% to about 11%, by weight of the mixture.

19. The composition of claim 10 , wherein the SbF 5 is present in an amount in the range of about 3% to about 15%, by weight of the mixture.

20. The composition of claim 19 , wherein the SbF 5 is present in an amount in the range of about 10% to about 11%, by weight of the mixture.

Assignees

• Chemours Co Fc Llc

Inventors

• Sun Xuehui
• Nappa Mario Joseph
• Krause Karl

Classifications

• C07C21/18

  containing fluorine · CPC title

• C07C17/087 Primary

  to unsaturated halogenated hydrocarbons · CPC title

• C07C2527/133

  Compounds comprising a halogen and vanadium, niobium, tantalium, antimonium or bismuth · CPC title

• C07C2527/12

  Fluorides · CPC title

• C07C19/10

  and chlorine · CPC title