Hydrofluorocarboximidate and methods of making and using the same

Patent metadata

Field	Value
Publication number	US-11053206-B2
Application number	US-201816634707-A
Country	US
Kind code	B2
Filing date	Aug 23, 2018
Priority date	Sep 28, 2017
Publication date	Jul 6, 2021
Grant date	Jul 6, 2021

Abstract

Described herein is an hydrofluorocarboximidate of formula (I) where: R H is a linear or branched alkyl group comprising 1 or 2 carbon atoms and (a) R f 1 and R f 2 are independent-selected from a linear or branched perfluorinated alkyl group comprising 1-8 carbon atoms and optionally comprising at least one catenated atom selected from oxygen, nitrogen, or combinations thereof; or (b) R f 1 and R f 2 are connected to form a ring structure comprising a total of 4-8 carbon atoms and in addition to the nitrogen atom from the carboximidate the ring structure may optionally comprises at least one catenated atom selected from oxygen, nitrogen, or combinations thereof. A method of making the hydrofluorocarboximidate with improved yield is described as well as various uses for the hydrofluorocarboximidate of Formula (I).

First claim

What is claimed is:

1. A method of making of a hydrofluorocarboximidate comprising:
contacting a perfluorinated imine with a trialkyl borate in the presence of base to form a hydrofluorocarboximidate of formula (I)

where:
R H is a linear or branched alkyl group comprising 1 or 2 carbon atoms; and
(a) R f 1 and R f 2 are independently selected from a linear or branched perfluorinated alkyl group comprising 1-8 carbon atoms and optionally comprising at least one catenated atom selected from oxygen, nitrogen, or combinations thereof; or (b) R f 1 and R f 2 are connected to form a ring structure comprising a total of 4-8 carbon atoms and optionally comprising at least one catenated atom selected from oxygen, nitrogen, or a combination thereof.

2. The method of claim 1 , wherein R f 1 and R f 2 form a perfluorinated 6-membered ring, wherein the ring comprises an oxygen atom.

3. The method of claim 1 , wherein (R f 1 ) and R f 2 form a perfluorinated 5-membered ring.

4. The method of claim 1 , wherein R f 1 is a perfluoro ethyl group and R f 2 is a perfluoro propyl group.

5. The method of claim 1 , wherein R H is a methyl group.

6. The method of claim 1 , wherein R H is an ethyl group.

7. The method of claim 1 , wherein the hydrofluorocarboximidate is selected from:

8. A working fluid comprising a hydrofluorocarboximidate wherein the hydrofluorocarboximidate is present in the working fluid in an amount of at least 25% by weight based on the total weight of the working fluid and the hydrofluorocarboximidate is of formula (I)

where:
R H is a linear or branched alkyl group comprising 1 or 2 carbon atoms; and
(a) R f 1 and R f 2 are independently selected from a linear or branched perfluorinated alkyl group comprising 1-8 carbon atoms and optionally comprising at least one catenated atom selected from oxygen, nitrogen, or combinations thereof; or (b) R f 1 and R f 2 are connected to form a ring structure comprising a total of 4-8 carbon atoms and optionally comprising at least one catenated atom selected from oxygen, nitrogen, or a combination thereof.

9. The method of claim 1 , wherein the hydrofluorocarboximidate based on closed-cup flashpoint testing following ASTM D-327-96 e-1 is not flammable.

10. The method of claim 1 , wherein the hydrofluorocarboximidate has a global warming potential of less than 100.

11. The method of claim 1 , wherein the hydrofluorocarboximidate has a boiling point of 80 to 150C.

12. The working fluid of claim 8 , wherein the working fluid further comprises a co-solvent.

13. The working fluid of claim 8 , wherein R f 1 and R f 2 form a perfluorinated 6-membered ring, wherein the ring comprises an oxygen atom.

14. The working fluid of claim 8 , wherein R f 1 and Rf2 form a perfluorinated 5-membered ring.

15. The working fluid of claim 8 , wherein R f 1 is a perfluoro ethyl group and R f 2 is a perfluoro propyl group.

16. The working fluid of claim 8 , wherein R H is a methyl group.

17. The working fluid of claim 8 , wherein R H is an ethyl group.

18. The working fluid of claim 8 , wherein the hydrofluorocarboximidate is selected from:

Assignees

• 3M Innovative Properties Co

Inventors

• Smith Sean M

Classifications

• C07D207/24

  Oxygen or sulfur atoms · CPC title

• C07C231/14

  by formation of carboxamide groups together with reactions not involving the carboxamide groups · CPC title

• C07D265/32 Primary

  with oxygen atoms directly attached to ring carbon atoms · CPC title

• C07C257/08 Primary

  having carbon atoms of imino-carboxyl groups bound to carbon atoms of six-membered aromatic rings · CPC title

• C09K5/04

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