Hydrofluoroethers and methods of using same

Patent metadata

Field	Value
Publication number	US-11325893-B2
Application number	US-201917278418-A
Country	US
Kind code	B2
Filing date	Sep 23, 2019
Priority date	Sep 26, 2018
Publication date	May 10, 2022
Grant date	May 10, 2022

Abstract

A compound is represented by the following general formula (I): (I) wherein each of Rf1 and Rf2 is, independently, F, CF3, C2F5, C3F7, or C4F9, with the proviso that if either of Rf1 and Rf2 is fluorine, then the other is not fluorine; Rf3 is F, CF3, C2F5, C3F7 or CF(CF3)2; Rf4 is F, CF3, C2F5, C3F7 or CF(CF3)2; and Rh is CH3 or C2H5.

First claim

What is claimed is:

1. A compound represented by the following general formula (I):

wherein each of Rf 1 and Rf 2 is, independently, F, CF 3 , C 2 F 5 , C 3 F 7 , or C 4 F 9 , with the proviso that if either of Rf 1 and Rf 2 is fluorine, then the other is not fluorine;
Rf 3 is F, CF 3 , C 2 F 5 , C 3 F 7 or CF(CF 3 ) 2 ;
Rf 4 is F, CF 3 , C 2 F 5 , C 3 F 7 or CF(CF 3 ) 2 ; and
Rh is CH 3 or C 2 H 5 .

2. The compound of claim 1 , wherein Rf 1 and Rf 2 are either both CF 3 or Rf 1 is CF 3 and Rf 2 is C 2 F 5 or C 3 F 7 or C 4 F 9 .

3. The compound of claim 1 , wherein Rf 3 is C 2 F 5 or CF(CF 3 ) 2 .

4. The compound of claim 1 , wherein Rh is CH 3 .

5. A compound represented by the following general formula (I):

where Rf 1 is CF 3 , C 2 F 5 or C 3 F 7 ;
Rf 2 is C 2 F 5 , C 3 F 7 , or C 4 F 9 ;
Rf 3 is CF(CF 3 ) 2 or C 3 F 7 ;
Rf 4 is F; and
Rh is H.

6. The compound of claim 5 , wherein Rf 1 is CF 3 and Rf 2 is C 2 F 5 , C 3 F 7 or C 4 F 9 .

7. A compound represented by the following general formula (I):

where one or two pairs of Rf groups from among Rf 1 , Rf 2 , Rf 3 , and Rf 4 are linked together to form a 5 or 6 membered perfluorinated carbon ring; and
Rh is CH 3 , C 2 H 5 or H;
wherein any of Rf 1 , Rf 2 , Rf 3 , and Rf 4 that are not linked together are as follows:
each of Rf 1 and Rf 2 is, independently, F, CF 3 , C 2 F 5 , C 3 F 7 , or C 4 F 9 with the proviso that if either of Rf 1 and Rf 2 is fluorine, then the other is not fluorine;
Rf 3 is F, CF 3 , C 2 F 5 , C 3 F 7 or CF(CF 3 ) 2 ; and
Rf 4 is F, CF 3 , C 2 F 5 , C 3 F 7 or CF(CF 3 ) 2 .

8. A working fluid comprising at least one compound of claim 1 , claim 5 , or claim 7 , wherein the compound is present in the working fluid at an amount of at least 25% by weight based on the total weight of the working fluid.

9. An apparatus for heat transfer comprising:
a device; and
a mechanism for transferring heat to or from the device, the mechanism comprising a working fluid that comprises a compound represented by the following general formula (I):

where each of Rf 1 and Rf 2 is, independently, F, CF 3 , C 2 F 5 , C 3 F 7 , or C 4 F 9 with the proviso that if either of Rf 1 and Rf 2 is fluorine, then the other is not fluorine;
Rf 3 is F, CF 3 , C 2 F 5 , C 3 F 7 or CF(CF 3 ) 2 ;
Rf 4 is F, CF 3 , C 2 F 5 , C 3 F 7 or CF(CF 3 ) 2 ; and
Rh is CH 3 , C 2 H 5 , or H.

10. The apparatus for heat transfer of claim 9 , wherein Rf 1 and Rf 2 are either both CF 3 or Rf 1 is CF 3 and Rf 2 is C 2 F 5 or C 3 F 7 or C 4 F 9 .

11. The apparatus for heat transfer of claim 9 , wherein Rf 3 is C 2 F 5 or CF(CF 3 ) 2 .

12. The apparatus for heat transfer of claim 9 , wherein Rh is H or CH 3 .

13. The apparatus for heat transfer of claim 9 , wherein the compound comprises the compound of claim 1 .

14. The apparatus for heat transfer of claim 9 , wherein the device is selected from a microprocessor, a semiconductor wafer used to manufacture a semiconductor device, a power control semiconductor, an electrochemical cell, a battery pack, an electrical distribution switch gear, a power transformer, a circuit board, a multi-chip module, a packaged or unpackaged semiconductor device, a fuel cell, and a laser.

15. The apparatus for heat transfer of claim 9 , wherein the mechanism for transferring heat is a component in a system for maintaining a temperature or temperature range of an electronic device.

16. A method of transferring heat comprising:
providing a device; and
transferring heat to or from the device using a heat transfer fluid that comprises a compound represented by the following general formula (I):

where each of Rf 1 and Rf 2 is, independently, F, CF 3 , C 2 F 5 , C 3 F 7 , or C 4 F 9 with the proviso that if either of Rf 1 and Rf 2 is fluorine, then the other is not fluorine;
Rf 3 is F, CF 3 , C 2 F 5 , C 3 F 7 or CF(CF 3 ) 2 ;
Rf 4 is F, CF 3 , C 2 F 5 , C 3 F 7 or CF(CF 3 ) 2 ; and
Rh is CH 3 , C 2 H 5 , or H.

17. A process for making a compound having the following general formula (I):

where each of Rf 1 and Rf 2 is, independently, F, CF 3 , C 2 F 5 , C 3 F 7 , or C 4 F 9 with the proviso that if either of Rf 1 and Rf 2 is fluorine, then the other is not fluorine;
Rf 3 is F, CF 3 , C 2 F 5 , C 3 F 7 or CF(CF 3 ) 2 ;
Rf 4 is F, CF 3 , C 2 F 5 , C 3 F 7 or CF(CF 3 ) 2 ; and

Rh is CH 3 , C 2 H 5 , or H,
the process comprising the step of reacting a perfluorinated olefin having the following general structure (II)

where each of Rf 1 and Rf 2 is, independently, F, CF 3 , C 2 F 5 , C 3 F 7 , or C 4 F 9 , with the proviso that if either of Rf 1 and Rf 2 is F, then the other is not fluorine; and
Rf 3 is F, CF 3 , C 2 F 5 , C 3 F 7 , or CF(CF 3 ) 2 ; and
Rf 4 is F, CF 3 , C 2 F 5 , C 3 F 7 or CF(CF 3 ) 2 ;
with a cyclic organic carbonate or an organic epoxide in the presence of a catalyst.

18. The process of claim 17 , wherein the cyclic organic carbonate comprises ethylene carbonate or propylene carbonate.

19. The process of claim 18 , wherein the organic epoxide comprises ethylene oxide or propylene oxide.

20. The process of claim 18 , wherein the catalyst is a halide salt.

21. The process of claim 18 , wherein the perfluorinated olefin of general structure (II) is generated in-situ from an isomeric perfluorinated olefin via catalytic isomerization.

Assignees

• 3M Innovative Properties Co
• Toso Matthew

Inventors

• Bulinski Michael J
• Lamanna William M
• Coughlin Forrest A
• Ren Hui
• Toso Nicholas A

Classifications

• C07D307/18 Primary

  with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms · CPC title

• C09K5/04

  the change of state being from liquid to vapour or vice versa · CPC title