IP Library Granted Patent US 7,888,538
Granted Patent B1
US 7,888,538 · App. 12/612,180 · Granted Feb 15, 2011

Catalyzed olefin insertion

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Quick Facts
Patent No.
US 7,888,538
App. No.
12/612,180
Granted
Feb 15, 2011
Kind
B1
Abstract

A process for the insertion of a partially fluorinated olefin into a fluorinated iodide in the presence of a nickel catalyst at a temperature of a maximum of 150° C. with an initial rate of 0.01 mole/hour without loss of selectivity is disclosed, as well as use of the process for insertion of a perfluorinated olefin with an initial rate of 0.04 mole/hour.

Claims (19)

1. A process for the preparation of a compound of Formula (I)

R f [C(X 1 X 2 )C(Y 1 Y 2 )] n I  (I)

wherein

each X 1 , X 2 , Y 1 , and Y 2 is independently fluorine, hydrogen, fluoroalkyl, or fluoroalkoxy;

n is 1, 2, or 3; and

R f is a perfluorinated or partially fluorinated carbon chain optionally interrupted with catenary oxygen or catenary sulfur;

comprising contacting, at a temperature of a maximum of 150° C. and at an initial rate of a minimum of 0.01 mole/hour, a partially fluorinated olefin with a fluoroalkyl iodide R f I wherein R f is defined as above, in the presence of a catalyst, wherein said catalyst is

iii) Ni(Z) m wherein each Z is independently PR 3 ; m is 2 to 4; R is phenyl, alkyl substituted phenyl, or C r H 2r+1 ; and r is 1 to 10; or

iv) a mixture of Ni and Z wherein Z is as defined above,

to yield a compound of Formula (I) with a selectivity for n is 1 of at least 65%.

2. The process of claim 1 , wherein R f contains 1 to 6 continuous fluorinated carbons.

3. The process of claim 1 , wherein R f contains 1 to 4 continuous fluorinated carbons.

4. The process of claim 1 wherein each of Y 1 and Y 2 is fluorine.

5. The process of claim 1 wherein the catalyst is a mixture of nickel and triphenylphosphine or a mixture of nickel and tributylphosphine.

6. The process of claim 1 wherein the olefin is trifluoromethyl propene, vinyl fluoride, fluorinated vinylether, or vinylidene fluoride.

7. The process of claim 1 wherein the temperature is from about 60° C. to about 150° C.

8. The process of claim 1 wherein the ratio of fluoroalkyl iodide to olefin is from about 1:2 to about 2:1.

9. The process of claim 1 wherein the initial rate is a minimum of 0.02 mole/hour.

10. The process of claim 1 wherein the selectivity for n is 1 is a minimum of about 75%.

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 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 10, 2009
From: PENG, SHENG; MOLOY, KENNETH GENE
To: E. I. DU PONT DE NEMOURS AND COMPANY
Reel/Frame 023633/0799 →