IP Library Granted Patent US 9,000,241
Granted Patent B2
US 9,000,241 · App. 13/277,268 · Granted Apr 7, 2015

Use of copper-nickel catalysts for dehlogenation of chlorofluorocompounds

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Quick Facts
Patent No.
US 9,000,241
App. No.
13/277,268
Granted
Apr 7, 2015
Kind
B2
Abstract

The disclosure describes a process for dehalogenation of chlorofluorocompounds. The process comprises contacting a saturated chlorofluorocompound with hydrogen in the presence of a catalyst at a temperature sufficient to remove chlorine and/or fluorine substituents to produce a fluorine containing terminal olefin.

Claims (31)

1. A process for dehalogenation of chlorofluorocompounds comprising contacting a saturated chlorofluorocompound with hydrogen in the presence of a catalyst at a temperature sufficient to remove chlorine or fluorine substituents to produce a fluorine containing terminal olefin wherein the catalyst is effective for dehalogenation of chlorofluorocompounds and wherein said chlorofluorocompound comprises a chlorofluorocompound having the formula:

R f CFX 1 CH 2 X 2

wherein R f is a fluoroalkyl group selected from CF 3 , C 2 F 5 , CHF 2 , and C 3 F 7 ;

X 1 is selected from F and Cl; and

X 2 is selected from Cl, Br, and I, wherein said catalyst is selected from copper on carbon, copper on calcium fluoride, copper and nickel on carbon, nickel and carbon, copper/nickel/chromium on calcium fluoride, unsupported alloys of copper and nickel, ruthenium on carbon, and rhenium on carbon.

2. The process of claim 1 , wherein said catalyst comprises nickel, copper, or combinations thereof.

3. The process of claim 2 , wherein said catalyst further comprises chromium.

4. The process of claim 2 , wherein said catalyst further comprises an alkali metal selected from potassium and cesium and rubidium.

5. The process of claim 2 , wherein said catalyst is unsupported alloys of copper and nickel having a molar ratio of copper:nickel of from about 1 to about 2 copper, and from about 2 to about 1 nickel.

6. The process of claim 4 , wherein said catalyst is copper/nickel/chromium on calcium fluoride having a molar ratio of copper:nickel:chromium of about 0 to about 1 copper; from about 0.5 to about 3 nickel; and from about 0 to about 2chromium.

7. The process of claim 6 , wherein said catalyst further comprises an alkali metal selected from potassium, cesium and rubidium.

8. The process of claim 7 , wherein the amount of said alkali metal is from 2 to 20 wt % of the total weight of said catalyst.

9. The process of claim 1 , wherein said chlorofluorocompound is a chlorofluorocompound having the formula

R f CFX 1 CH 2 X 2 ;

wherein R f is a fluoroalkyl group selected from CF 3 , C 2 F 5 ,CHF 2 , and C 3 F 7 ;

X 1 is selected from F and Cl; and

X 2 is selected from Cl, Br, and I.

10. The process of claim 1 , wherein the process is conducted at a temperature of from about 200° C. to about 450° C.

11. The process of claim 1 , wherein the process is conducted at a temperature of from about 300° C. to about 400° C.

12. The process of claim 1 , wherein the process is conducted at a temperature of from about 325° C. to about 375° C.

13. The process of claim 1 , wherein the molar ratio of hydrogen to the chlorofluorocompound is from about 10:1 to about 0.5:1.

14. The process of claim 1 , wherein the molar ratio of hydrogen to the chlorofluorocompound is from about 6:1 to about 1:1.

15. The process of claim 1 , wherein the molar ratio of hydrogen to the chlorofluorocompound is from about 3:1 to about 1:1.

16. The process of claim 1 , wherein said chlorofluorocompound comprises 3-chloro-1,1,1,2,2-pentafluoropropane.

17. The process of claim 16 , wherein 2,3,3,3-tetrafluoro-1-propene is produced.

18. The process of claim 1 , wherein said chlorofluorocompound comprises 2,3-dichloro-1,1,1,2-tetrafluoropropane.

19. The process of claim 18 , wherein 2,3,3,3-tetrafluoro-1-propene is produced.

20. The process of claim 1 , wherein said chlorofluorocompound comprises 1-chloro-1,2,2,3-tetrafluoropropane.

21. The process of claim 20 , wherein 1,2,3-trifluoropropene is produced.

22. The process of claim 1 , wherein said chlorofluorocompound comprises 3-chloro-1,1,2,2-tetrafluoropropane.

23. The process of claim 22 , wherein 2,3,3-trifluoro-1-propene is produced.

Assignments (5)
RELEASE OF SECURITY INTEREST Recorded Apr 4, 2018
From: JPMORGAN CHASE BANK, N.A., AS ADMINISTRATIVE AGENT
To: THE CHEMOURS COMPANY FC, LLC
Reel/Frame 045845/0913 →
SECURITY INTEREST Recorded Apr 4, 2018
From: THE CHEMOURS COMPANY FC, LLC
To: JPMORGAN CHASE BANK, N.A., AS ADMINISTRATIVE AGENT
Reel/Frame 045846/0011 →
SECURITY AGREEMENT Recorded Jun 10, 2015
From: THE CHEMOURS COMPANY FC LLC; THE CHEMOURS COMPANY TT, LLC
To: JPMORGAN CHASE BANK, N.A.
Reel/Frame 035839/0675 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 15, 2015
From: E. I. DU PONT DE NEMOURS AND COMPANY
To: THE CHEMOURS COMPANY FC, LLC
Reel/Frame 035432/0023 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 23, 2011
From: NAPPA, MARIO JOSEPH; SWEARINGEN, EKATERINA N.; SIEVERT, ALLEN CAPRON; SUN, XUEHUI
To: E. I. DU PONT DE NEMOURS AND COMPANY
Reel/Frame 027438/0768 →