Hydrofluoroalkane composition

Patent metadata

Field	Value
Publication number	US-10988422-B2
Application number	US-202016847041-A
Country	US
Kind code	B2
Filing date	Apr 13, 2020
Priority date	May 21, 2015
Publication date	Apr 27, 2021
Grant date	Apr 27, 2021

Abstract

The disclosure relates to a method for hydrofluorination of an olefin of the formula: RCX═CYZ to produce a hydrofluoroalkane of formula RCXFCHYZ or RCXHCFYZ, wherein X, Y, and Z are independently the same or different and are selected from the group consisting of H, F, Cl, Br, and C1-C6 alkyl which is partially or fully substituted with chloro or fluoro or bromo; and R is a C1-C6 alkyl which is unsubstituted or substituted with chloro or fluoro or bromo, comprising reacting the olefin with HF in the liquid-phase, in the presence of SbF5, 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 liquid phase composition comprising:
a catalyst comprising SbF 5 and a hydrofluoroalkane composition comprising at least one hydrofluoroalkane selected from the group consisting of RCH 2 CHFCl, RCH 2 CFCl 2 , and RCH 2 CH 2 F;
wherein R is trifluoromethyl or pentafluoroethyl; and
wherein the hydrofluoroalkane composition comprises greater than 95 mol % of the at least one hydrofluoroalkane.

2. The liquid phase composition of claim 1 , wherein the hydrofluoroalkane composition comprises greater than 98 mol % of the at least one hydrofluoroalkane.

3. The liquid phase composition of claim 1 , wherein the hydrofluoroalkane composition comprises greater than 99 mol % of the at least one hydrofluoroalkane.

4. The liquid phase composition of claim 1 , wherein the liquid phase composition is at a temperature in the range of from about −30° C. to about 65° C.

5. The liquid phase composition of claim 4 , wherein the temperature is from about −30° C. to about 25° C.

6. The liquid phase composition of claim 5 , wherein the temperature is from about 5° C. to about 25° C.

7. The liquid phase composition of claim 1 , wherein the hydrofluoroalkane includes 1,1,1,3-tetrafluoropropane, or 3-chloro-1,1,1,3-tetrafluoropropane.

8. The liquid phase composition of claim 7 , wherein the hydrofluoroalkane composition comprises greater than 98 mol % 1,1,1,3-tetrafluoropropane, or 3-chloro-1,1,1,3-tetrafluoropropane.

9. The liquid phase composition of claim 7 , wherein the hydrofluoroalkane composition comprises greater than 99 mol % 1,1,1,3-tetrafluoropropane, or 3-chloro-1,1,1,3-tetrafluoropropane.

10. The liquid phase composition of claim 1 further comprising at least one olefin, wherein the olefin is selected from the group consisting of RCH═CHCl, and RCH═CH 2 .

11. The liquid phase composition of claim 10 , wherein the olefin includes 3,3,3-trifluoropropene, or (Z)- or (E)-1-chloro-3,3,3-tetrafluoropropene, and the hydrofluoroalkane includes 1,1,1,3-tetrafluoropropane, or 3-chloro-1,1,1,3-tetrafluoropropane.

12. The liquid phase composition of claim 1 , wherein the catalyst consists essentially of SbF 5 .

13. A liquid phase composition comprising:
at least one member selected from the group consisting of RCCl═CH 2 , RCH═CHCl, RCH═CCl 2 and RCH═CH 2 , a hydrofluorination catalyst comprising SbF 5 , and a hydrofluoroalkane composition comprising at least one hydrofluoroalkane selected from the group consisting of RCFClCH 3 , RCH 2 CHFCl, RCH 2 CFCl 2 , RCHFCH 3 , and RCH 2 CH 2 F;
wherein when the at least one member is RCCl═CH 2 , the at least one hydrofluoroalkane is RCFClCH 3 ,
wherein when the at least one member is RCH═CHCl, the at least one hydrofluoroalkane is RCH 2 CHFCl,
wherein when the at least one member is RCH═CCl 2 , the at least one hydrofluoroalkane is RCH 2 CFCl 2 ,
wherein when the at least one member is RCH═CH 2 , the at least one hydrofluoroalkane is RCHFCH 3 and RCH 2 CH 2 F,
wherein the hydrofluoroalkane composition comprises greater than 95 mol % of the at least one hydrofluoroalkane, and
wherein R is trifluoromethyl or pentafluoroethyl.

14. The liquid phase composition of claim 13 , wherein the hydrofluoroalkane composition comprises greater than 98 mol % of the at least one hydrofluoroalkane.

15. The liquid phase composition of claim 13 , wherein the hydrofluoroalkane composition comprises greater than 99 mol % of the at least one hydrofluoroalkane.

16. The liquid phase composition of claim 1 , wherein the liquid phase composition is at a temperature in the range of from about −30° C. to about 25° C.

17. The liquid phase composition of claim 13 , wherein the hydrofluorination catalyst consists essentially of SbF 5 .

18. The liquid phase composition of claim 13 , wherein the at least one member is RCCl═CH 2 , the at least one hydrofluoroalkane is RCFClCH 3 , and R is trifluoromethyl.

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

• C07C17/08

  to unsaturated hydrocarbons · CPC title

• B01J23/18

  Arsenic, antimony or bismuth · CPC title

• B01J23/16

  of arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium · CPC title