IP Library Granted Patent US 9,624,147
Granted Patent B2
US 9,624,147 · App. 14/922,237 · Granted Apr 18, 2017

Production of short chain perfluoroalkyl iodides from higher order telomers

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Quick Facts
Patent No.
US 9,624,147
App. No.
14/922,237
Granted
Apr 18, 2017
Kind
B2
Abstract

An improved process for producing perfluoroalkyl iodides of formula (I) F(CF 2 CF 2 ) n —I  (I) wherein n is an integer from 2 to 3, wherein the improvement comprises thermolyzing at least one perfluoroalkyl iodide of formula (II), optionally in the presence of perfluoroethyl iodide, formula (III) F(CF 2 CF 2 ) m —I  (II) F(CF 2 CF 2 ) p —I  (III) wherein m is an integer greater than or equal to 4, and p is 1, wherein a) the molar ratio of formula (III) to formula (II) is less than 1.0, b) the residence time is from about 0.1 to about 10 seconds, and c) the temperature is from about 450° C. to about 500° C.

Claims (22)

1. An improved process for producing perfluoroalkyl iodides of formula (I)

F(CF 2 CF 2 ) n —I  (I)

wherein n is an integer from 2 to 3, wherein the improvement comprises thermolyzing at least one perfluoroalkyl iodide of formula (II), optionally in the presence of perfluoroethyl iodide, formula (III)

F(CF 2 CF 2 ) m —I  (II)

F(CF 2 CF 2 ) p —I  (III)

wherein m is an integer greater than or equal to 4, and p is 1, wherein a) the molar ratio of formula (III) to formula (II) is 0, b) the residence time is from 0.1 to 10 seconds, and c) the temperature is from 450° C. to 500° C.

2. The process of claim 1 wherein the selectivity for species (I) is greater than 45 mol %.

3. The process of claim 1 wherein the temperature is from 470° C. to 495° C.

4. The process of claim 1 wherein the residence time is held at from 0.4 to 9 seconds.

5. The process of claim 1 wherein the selectivity for species (I) is greater than 45 mol % without use of iodine as a reactant.

6. The process of claim 1 wherein the selectivity for perfluoroalkanes is less than 20 mol %.

7. The process of claim 6 wherein the selectivity for perfluoroalkanes is less than 10 mol %.

8. The process of claim 1 , performed in the absence of a TFE trap species.

9. An improved process for producing perfluoroalkyl iodides of formula (I)

F(CF 2 CF 2 ) n —I  (I)

wherein n is an integer from 2 to 3, wherein the improvement comprises thermolyzing, in the absence of a TFE trap species, at least one perfluoroalkyl iodide of formula (II), optionally in the presence of perfluoroethyl iodide, formula (III)

F(CF 2 CF 2 ) m —I  (II)

F(CF 2 CF 2 ) p —I  (III)

wherein m is an integer greater than or equal to 4, and p is 1, wherein a) the molar ratio of formula (III) to formula (II) is 0, b) the residence time is from 0.1 to 10 seconds, and c) the temperature is from 450° C. to 500° C.

10. The process of claim 9 wherein the selectivity for species (I) is greater than 45 mol %.

11. The process of claim 9 wherein the residence time is held at from 0.4 to 9 seconds.

12. The process of claim 9 wherein the temperature is from 470° C. to 495° C.

Assignments (2)
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 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 14, 2016
From: GETTY, STEPHEN JAMES; VOLKER, GEORGE MURRAY; HACARLIOGLU, PELIN
To: THE CHEMOURS COMPANY FC, LLC
Reel/Frame 037489/0409 →