Catalysed synthesis of fluorinated alkenes and fluorinated alkene compositions

Patent metadata

Field	Value
Publication number	US-12441673-B2
Application number	US-202017774278-A
Country	US
Kind code	B2
Filing date	Dec 9, 2020
Priority date	Dec 9, 2019
Publication date	Oct 14, 2025
Grant date	Oct 14, 2025

Abstract

A method of producing a fluoroolefin includes contacting a compound of formula (1), R f CX 1 ═CHCF 3 , with a fluorinated ethylene compound of formula (2), CX 2 X 3 ═CX 4 X 5 in the presence of a catalyst. In the compound of formula (1), R f is a linear or branched C 1 -C 10 perfluorinated alkyl group and X 1 is H, Br, Cl, or F. In the compound of formula (2), X 2 , X 3 , X 4 , and X 5 are each independently H, Br, Cl, or F and at least three of X 2 , X 3 , X 4 , and X 5 are F. The resulting composition comprises a compound of formula (3), R f (CF 2 ) n CX 6 ═CH(CF 2 ) m CX 7 X 8 CFX 9 X 10 . In the compound of formula (3), X 6 , X 7 , X 8 , X 9 , and X 10 are each independently H, Br, Cl, or F, and the total number of each of H, Br, Cl, and F corresponds to the total number of each of H, Br, Cl, and F provided by the compounds of formulae (1) and (2).

First claim

What is claimed is:

1. A method of producing a fluoroolefin comprising: contacting a compound comprising formula (1),
R f CX 1 ═CHCF 3   (1)

wherein R f is a linear or branched C 1 -C 10 perfluorinated or polyfluorinated alkyl group; and wherein X1 is H, Br, Cl, or F; wherein the compound of formula (1) comprises at least one member selected from the group consisting of C 4 F 9 CH═CHCF 3 , (CF 3 ) 2 CFCH═CHCF 3 , CF 3 CH═CFCF 3 , and CF 3 CH═CCICF 3 ; with a fluorinated ethylene compound comprising formula (2),
CX 2 X 3 ═CX 4 X 5   (2)

wherein X 2 , X 3 , X 4 , and X 5 are each independently H, Br, Cl, or F; and wherein at least three of X 2 , X 3 , X 4 , and X 5 are F; wherein the fluorinated ethylene of formula (2) comprises at least one of CFCl═CF 2 ; CFCl═CFCl, CFH═CF 2 (HFO-1123), CFH═CFH (HFO-1132, and CF 2 =CH 2 (VF 2 ); in the presence of a catalyst in an amount sufficient to form a composition comprising a compound of formula (3),
R f (CF 2 ) n CX 6 ═CH(CF 2 ) m CX 7 X 8 CFX 9 X 10   (3)

wherein n is an integer from 0 to 10; wherein m is an integer from 1 to 10; wherein X 6 , X 7 , X 8 , X 9 , and X 10 are each independently H, Cl, or F; and wherein the total number of each of H, Cl, and F represented by X 6 , X 7 , X 8 , X 9 , and X 10 is the same as the total number of each of H, Cl, and F provided by X 1 , X 2 , X 3 , X 4 , and X 5 in formulae (1) and (2), wherein the compound of formula (3) comprises at least one member selected from the group consisting of C 4 F 9 CH═CHCF 2 CFClCF 3 , C 4 F 9 CH═CHCF 2 CF 2 CF 2 Cl, (CF 3 ) 2 CFCH═CHCF 2 CFClCF 3 , (CF 3 ) 2 CFCH═CHCF 2 CF 2 CF 2 Cl, C 2 F 5 CH═CHC 2 F 5 , C 2 F 5 CF═CHCFClCF 3 , C 2 F 5 CF═CHCF 2 CF 2 Cl, C 3 F 7 CH═CClCF 3 and C 3 F 7 CH═CClCF 3 .

2. The method of claim 1 wherein:
R f is selected from the group consisting of CF 3 , C 2 F 5 , C 3 F 7 , i-C 3 F 7 , C 4 F 9 , C 5 F 11 , i-C 5 F 11 , C 6 F 13 , and i-C 6 F 13 .

3. The method of claim 1 , wherein the amount sufficient includes a molar ratio of fluoroethylene:the compound of formula (1) of 0.01:1 to 5:1.

4. The method of claim 3 , wherein the amount sufficient includes a molar ratio of fluoroethylene:the compound of formula (1) of 0.1:1 to 2:1.

5. The method of claim 1 , wherein the amount sufficient includes a molar ration of the compound of formula (2) and the compound of formula (1) of 0.01:1 to 5:1.

6. The method of claim 1 , wherein the composition further includes a solvent.

7. The method of claim 6 , wherein the solvent comprises a perfluorinated saturated compound.

8. The method of claim 7 , wherein the perfluorinated saturated compound comprises at least one member selected from the group consisting of perfluoropentane, perfluorohexane, cyclic dimer of hexafluoropropene, (mixture of perfluoro-1,2- and perfluoro-1,3-dimethylcyclobutanes), and combinations thereof.

9. The method of claim 1 wherein:
the catalyst includes antimony pentafluoride (SbF 5 ) or a compound of formula (4),
SbCl x F 5-x wherein x=0.01 to 0.5.

10. The method of claim 9 , wherein the catalyst comprises at least one member selected from the group consisting of aluminum chloride (AlCl 3 ), antimony pentafluoride (SbF 5 ), and aluminum chlorofluoride AlCl x F 3-x .

11. The method of claim 1 , wherein the contacting is performed at sub-ambient or ambient temperature.

12. The method of claim 1 , wherein the reaction is conducted under autogenic pressure.

13. The method of claim 1 , wherein the reaction is conducted at 0.1 to 300 psig.

14. The method of claim 1 , wherein the reaction is conducted in a closed system.

15. The method of claim 1 , wherein the contacting is performed at a temperature of −50° C. to 50° C.

Assignees

• Chemours Co Fc Llc

Inventors

• Petrov Viacheslav A
• Juhasz Jason R
• Simoni Luke David
• Brandt Drew Richard
• Stehman Jonathan P

Classifications

• H05K7/203 Primary

  by immersion · CPC title

• C09K5/10

  Liquid materials · CPC title

• H01M10/6567

  Liquids · CPC title

• H01M10/613

  Cooling or keeping cold · CPC title

• C07C21/18

  containing fluorine · CPC title