Propenylamines and methods of making and using same

Patent metadata

Field	Value
Publication number	US-11858875-B2
Application number	US-202217874851-A
Country	US
Kind code	B2
Filing date	Jul 27, 2022
Priority date	Aug 22, 2016
Publication date	Jan 2, 2024
Grant date	Jan 2, 2024

Abstract

A composition includes a perfluorinated propenylamine represented by the following general formula (1):

Each occurrence of R f1 and R f2 is:
(i) independently a linear or branched perfluoroalkyl group having 1-8 carbon atoms and optionally comprises one or more catenated heteroatoms; or (ii) bonded together to form a ring structure having 4-8 carbon atoms and that optionally comprises one or more catenated heteroatoms.

At least 60 wt. % of the perfluorinated propenylamine is in the form of the E isomer, based on the total weight of the perfluorinated propenylamine in the composition.

First claim

What is claimed is:

1. A method of making a composition, the method comprising:
contacting a perfluorinated allylamine of general formula (2) with an active isomerization catalyst;

carrying out a selective catalytic isomerization to form a 1-propenylamine of general formula (1);

wherein each R f1 and R f2 comprises:
(i) independently a linear or branched perfluoroalkyl group having 1-8 carbon atoms and optionally comprises one or more catenated heteroatoms; or
(ii) bonded together to form a ring structure having 4-8 carbon atoms and that
optionally comprises one or more catenated heteroatoms, and

wherein the selectivity for formation of the E isomer of formula (1) is at least 60 wt. %, based on the total weight of the propenylamine in the composition.

2. A working fluid comprising a composition according to claim 1 , wherein the composition is present in the working fluid at an amount of at least 25% by weight based on the total weight of the working fluid.

3. A method of transferring heat comprising:
providing a device; and
transferring heat to or from the device using a heat transfer fluid that the composition or working fluid according to claim 1 .

Assignees

• 3M Innovative Properties Company

Inventors

• Lamanna William M
• Bulinski Michael J
• Smith Sean M
• Monteil Alexandre R
• Costello Michael G
• Owens John G

Classifications

• C07C209/68 Primary

  from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton · CPC title

• C07D295/067

  with the ring nitrogen atoms and the substituents attached to the same carbon chain, which is not interrupted by carbocyclic rings · CPC title

• C09K5/10

  Liquid materials · CPC title

• H01M8/04029

  Heat exchange using liquids · CPC title

• H01M8/04701

  Temperature · CPC title