IP Library Granted Patent US 8,263,816
Granted Patent B2
US 8,263,816 · App. 12/301,065 · Granted Sep 11, 2012

1,2,3,3,3-Pentafluoropropene production processes

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Quick Facts
Patent No.
US 8,263,816
App. No.
12/301,065
Granted
Sep 11, 2012
Kind
B2
Abstract

A process is disclosed for making CF 3 CF═CHF. The process involves reacting CF 3 CClFCCl 2 F with H 2 in a reaction zone in the presence of a catalyst to produce a product mixture comprising CF 3 CF═CHF. The catalyst has a catalytically effective amount of palladium supported on a support selected from the group consisting of alumina, fluorided alumina, aluminum fluoride and mixtures thereof and the mole ratio of H 2 to CF 3 CClFCCl 2 F fed to the reaction zone is between about 1:1 and about 5:1. Also disclosed are azeotropic compositions of CF 3 CClFCCl 2 F and HF and azeotropic composition of CF 3 CHFCH 2 F and HF.

Claims (19)

1. A process for making 1,2,3,3,3-pentafluoropropene, comprising:

reacting CF 3 CClFCCl 2 F with H 2 in a reaction zone in the presence of a catalyst comprising a catalytically effective amount of palladium supported on a support selected from the group consisting of alumina, fluorided alumina, aluminum fluoride and mixtures thereof, to produce a product mixture comprising 1,2,3,3,3-pentafluoropropene, wherein the mole ratio of H 2 to CF 3 CClFCCl 2 F fed to the reaction zone is between about 1:1 and about 5:1.

2. The process of claim 1 wherein said 1,2,3,3,3-pentafluoropropene is recovered from the product mixture.

3. The process of claim 1 wherein 2,3,3,3-tetrafluoro-1-propene is also present in the product mixture; and wherein said 2,3,3,3-tetrafluoro-1-propene is also recovered.

4. The process of claim 1 wherein 1,1,1,2,3-pentafluoropropane is also present in the product mixture; and wherein said 1,1,1,2,3-pentafluoropane is also recovered.

5. The process of claim 1 wherein 1-chloro-1,2,3,3,3-pentafluoropropene is also present in the product mixture; and wherein said 1-chloro-1,2,3,3,3-pentafluoropropene is also recovered.

6. The process of claim 1 wherein HF is also fed to the reaction zone.

7. The process of claim 6 wherein 1-chloro-1,1,2,3,3,3-hexafluoropropane is also present in the product mixture; and wherein 1-chloro-1,1,2,3,3,3-hexafluoropropane is recovered from the product mixture.

8. The process of claim 6 wherein said HF is fed to the reaction zone as an azeotrope or near azeotrope comprising HF and CF 3 CClFCCl 2 F.

9. The process of claim 6 wherein 1,1,1,2,3-pentafluoropropane is also present in the product mixture; and wherein said 1,1,1,2,3-pentafluoropropane is also recovered from the product mixture.

10. A process for making 1,1,1,2,3-pentafluoropropane, comprising:

(1) recovering 1-chloro-1,2,3,3,3-pentafluoropropene in accordance with claim 5 ; and

(2) hydrogenating said 1-chloro-1,2,3,3,3-pentafluoropropene to 1,1,1,2,3-pentafluoropropane.

11. A process for making 1,1,1,2,3-pentafluoropropane, comprising:

(1) recovering 1,2,3,3,3-pentafluoropropene in accordance with claim 2 ; and

(2) hydrogenating said 1,2,3,3,3-pentafluoropropene, optionally in the presence of HF, to 1,1,1,2,3-pentafluoropropane.

12. A process for making 1,1,1,2,3,3-hexafluoropropane comprising:

(1) recovering 1-chloro-1,1,2,3,3,3-hexafluoropropane in accordance with claim 7 ; and

(2) hydrogenating said 1-chloro-1,1,2,3,3,3-hexafluoropropane to 1,1,1,2,3,3-hexafluoropropane.

Assignments (4)
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 →