IP Library Granted Patent US 8,044,251
Granted Patent B2
US 8,044,251 · App. 12/755,671 · Granted Oct 25, 2011

Process for the preparation of halo-olefins

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Quick Facts
Patent No.
US 8,044,251
App. No.
12/755,671
Granted
Oct 25, 2011
Kind
B2
Abstract

Described is a process for preparing a halo-olefin comprising contacting a halogenated hydrocarbon with a metal dehalogenating agent, in a solvent, in the presence of a phase transfer catalyst, under conditions sufficient to dehalogenate said halogenated hydrocarbon to produce a product stream comprising said halo-olefin. In one embodiment, the halogenated hydrocarbon is trifluorotrichloroethane and the halo-olefin is chlorotrifluoroethylene.

Claims (12)

1. A process for preparing a haloolefin comprising:

contacting a halogenated hydrocarbon with a metal dehalogenating agent, in a solvent, in the presence of a phase transfer catalyst, under conditions sufficient to dehalogenate said halogenated hydrocarbon to produce a product stream comprising said haloolefin.

2. The process of claim 1 , wherein said haloolefin is selected from the group consisting of chlorotrifluoroethylene, tetrafluoroethylene, difluoroethylene and vinyl chloride.

3. The process of claim 2 wherein said halo-olefin in chlorotrifluoroethylene.

4. The process of claim 1 , wherein said halogenated hydrocarbon is selected from the group consisting of trichlorotrifluoroethane, trichloroethane, dichlorodifluorethane and dichlorotetrafluoroethane.

5. The process of claim 4 , wherein said halogenated hydrocarbon is trichlorotrifluoroethane.

6. The process of claim 1 , wherein said dehalogenating agent is selected from the group consisting of zinc, tin, manganesium, iron, and aluminum.

7. The process of claim 6 , wherein said dehalogenating agent is zinc.

8. The process of claim 1 , wherein said phase transfer catalyst is selected from the group consisting of crown ethers, onium salts, cryptates and polyalkylene glycols and derivatives thereof, and mixtures thereof.

9. The process of claim 8 , wherein said phase transfer catalyst is an onium salt.

10. The process of claim 8 , wherein said phase transfer catalyst is a quaternary ammonium salt.

11. The process of claim 10 , wherein said quaternary ammonium salt is a tetrabutylammonium bromide.

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 May 20, 2010
From: NAPPA, MARIO JOSEPH; SUN, XUEHUI
To: E. I. DU PONT DE NEMOURS AND COMPANY
Reel/Frame 024412/0583 →