IP Library › Granted Patent US 8,907,088
Granted Patent B2
US 8,907,088 · App. 13/548,425 · Granted Dec 9, 2014

Methods of making cyclic, N-amino functional triamines

Inventors: Stephen W. King (League City, TX); Stefan K. Mierau (South Charleston, WV); Thomas Z. Smak (Arlington Heights, IL)
Assignee: Union Carbide Chemicals & Plastics Technology LLC
C07D295/13C07D241/04
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Quick Facts
Patent No.
US 8,907,088
App. No.
13/548,425
Granted
Dec 9, 2014
Kind
B2
Abstract

The present invention provides strategies for making cyclic triamines. Reactant media including certain precursors and/or certain types of catalysts can be converted into cyclic triamines with improved conversion and selectivity. The strategies can be incorporated into reactions that involve transamination schemes and/or reductive amination schemes. In the case of transamination, for instance, using transamination to cause ring closure of higher amines in the presence of a suitable catalyst leads to desired cyclic triamines with notable conversion and yield. In the case of reductive amination, reacting suitable polyfunctional precursors in the presence of a suitable catalyst also yields cyclic triamines via ring closure with notable selectivity and conversion. Both transamination and reductive amination methodologies can be practiced under much milder temperatures than are used when solely acid catalysts are used. Preferred embodiments can produce reaction mixtures that are generally free of salt by-products.

Claims (5)

1. A method of making a cyclic triamine of the type comprising a cyclic moiety comprising first and second nitrogen backbone atoms and an N-amino moiety pendant from at least one of the nitrogen backbone atoms, comprising the step of causing ring closure of a hydroxyl functional amine in the presence of a catalyst comprising Ni and Re under conditions effective to cause the hydroxyl functional amine to react with itself to form the cyclic triamine.

2. The method according to claim 1 , wherein the hydroxyl functional amine is a linear dihydroxyalkyleneamine.

3. The method of claim 1 , wherein the hydroxyl functional amine is a branched dihydroxyalkyleneamine.

4. The method of claim 1 , wherein the hydroxyl functional amine is a branched hydroxyalkyldialkylenetriamine.

5. The method of claim 1 , wherein the hydroxyl functional amine is a linear hydroxyalkyldialkylenetriamine.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 28, 2020
From: UNION CARBIDE CHEMICALS & PLASTICS TECHNOLOGY LLC
To: UNION CARBIDE CORPORATION
Reel/Frame 051642/0392 →
Continuity (3)
Division 12587380 · Oct 6, 2009
Provisional Application 61195412 · Oct 6, 2008
Related Publication 20120277435A1 · Nov 1, 2012