IP Library Granted Patent US 11,840,492
Granted Patent B2
US 11,840,492 · App. 17/812,203 · Granted Dec 12, 2023

Dehydrohalogenation of hydrochlorofluorocarbons

Inventors: Xuehui Sun (Kennett Square, PA); Karl Krause (Kennett Square, PA)
Assignee: THE CHEMOURS COMPANY, FC, LLC
C07C17/25C07C21/18
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Quick Facts
Patent No.
US 11,840,492
App. No.
17/812,203
Granted
Dec 12, 2023
Kind
B2
Abstract

A dehydrohalogenation product includes a hydrochlorofluorocarbon mixture of a fluoroolefin of formula RCX═CZQ and a halofluoroalkane of formula RCXYCZQT. R is a perfluorinated alkyl group and X, Z, and Q are independently H or halogen. One of Y and T is H and the other is Cl, Br, or I. About 80% or greater of the hydrochlorofluorocarbon mixture is the fluoroolefin. The dehydrohalogenation product also includes a caustic agent and a solvent. In some embodiments, the dehydrohalogenation product is free of any catalyst, including any phase transfer catalyst.

Claims (29)

1. A dehydrohalogenation conversion process comprising vigorously contacting, in one of a batch process and a semi-batch process, a halofluoroalkane of formula RCXYCZQT and a caustic agent, in a solvent comprising at least one of water and alcohol, in the absence of any additional phase transfer catalyst at a temperature in a range of about 20° C. to about 100° C., to form a fluoroolefin of formula RCX═CZQ, wherein R is a perfluorinated alkyl group and X, Z, and Q are independently H or halogen, and one of Y and T is H and the other is Cl, Br, or I, and where the conversion is at least 98% of the maximum based on a starting ratio of caustic agent and halofluoroalkane.

2. The process of claim 1 , wherein the conversion is at least 98% of the halofluoroalkane.

3. The process of claim 1 , wherein RCX═CZQ comprises one of CF 3 CF═CH 2 , CF 3 CH═CHF, and CF 3 CCl═CH 2 .

4. The process of claim 1 , wherein RCX═CZQ comprises CF 3 CF═CH 2 .

5. The process of claim 1 , wherein the solvent is an aqueous solvent.

6. The process of claim 1 , wherein the solvent includes a co-solvent.

7. The process of claim 1 , wherein the dehydrohalogenation is conducted for about 30 to 120 minutes.

8. The process of claim 1 , wherein the fluoroolefin is a chlorofluoroolefin.

9. The process of claim 8 , wherein the chlorofluoroolefin includes at least one chlorine atom.

10. The process of claim 1 , wherein the vigorous contacting involves agitation.

11. The process of claim 1 , wherein the caustic agent and halofluoroalkane are used at a caustic agent:halofluoroalkane molar ratio sufficient to convert at least 99% of the halofluoroalkane.

12. The process of claim 1 , wherein the caustic agent is present in sufficient excess to convert at least 98% of the halofluoroalkane.

13. The process of claim 1 , wherein the halofluoroalkane is present in an amount sufficient for at least 98% conversion.

14. A composition comprising:

a hydrochlorofluorocarbon mixture comprising:

a fluoroolefin of formula RCX═CZQ, wherein R is a perfluorinated alkyl group and X, Z, and Q are independently H or halogen; and

a halofluoroalkane of formula RCXYCZQT, wherein one of Y and T is H and the other is Cl, Br, or I;

an amine;

a caustic agent; and

a solvent comprising a co-solvent selected from alcohols, diols, ethers, esters, linear alkanes, branched alkanes, cyclic alkanes, fluorinated diluents, and combinations thereof.

15. A dehydrohalogenation process comprising vigorously contacting a halofluoroalkane of formula RCXYCZQT, a caustic agent, and an amine in an aqueous solvent in the absence of any phase transfer catalyst, in one of a batch process and a semi-batch process, to produce a product comprising a fluoroolefin of formula RCX═CZQ, wherein R is a perfluorinated alkyl group and X, Z, and Q are independently H or halogen, and one of Y and T is H and the other is Cl, Br, or I.

16. The process of claim 15 , wherein the aqueous solvent comprises a co-solvent.

17. The process of claim 16 , wherein the co-solvent is selected from alcohols, diols, ethers, esters, linear alkanes, branched alkanes, cyclic alkanes, fluorinated diluents, and combinations thereof.

18. The process of claim 15 , wherein the dehydrohalogenation is conducted for about 30 to 60 minutes.

19. The process of claim 15 , wherein the fluoroolefin is a chlorofluoroolefin.

20. The process of claim 19 , wherein the chlorofluoroolefin includes at least one chlorine atom.

21. The process of claim 15 , wherein the vigorous contacting involves agitation.

22. The process of claim 15 , wherein the caustic agent is present in sufficient excess to convert at least 98% of the halofluoroalkane.

23. The process of claim 15 , wherein the amine is present in an amount sufficient for at least 98% conversion.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 3, 2023
From: SUN, XUEHUI; KRAUSE, KARL
To: THE CHEMOURS COMPANY FC, LLC
Reel/Frame 065105/0432 →
SECURITY INTEREST Recorded Apr 11, 2023
From: THE CHEMOURS COMPANY FC, LLC
To: JPMORGAN CHASE BANK, N.A., AS ADMINISTRATIVE AGENT
Reel/Frame 063294/0692 →