Transamination of Nitrogen Compounds for Polyamine Mixtures

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Solution Overview

Problem

Current transamination processes face limitations in customizing product mixtures of amine compounds for specific end-use applications, struggling to control cyclic and acyclic content effectively, often resulting in low yields and byproduct salts that require disposal.

Innovation Solution

A transamination method using mixed nitrogen-containing reactants with specific carbon atom spacings between amine groups, allowing for adjustment of molar ratios to produce customized cyclic and acyclic polyamine mixtures, including homopiperazine and other polyamines, using hydrogenation/dehydrogenation catalysts to optimize product composition.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Adaptability or versatility

If traditional transamination processes are used, then amine products can be manufactured, but the ability to customize product mixtures for desired end uses is limited

Engineering Contradiction:

Improveproduct mixture customizationVSAvoidprocess complexity

Core Design Contradiction:

Adaptability or versatilityVSEase of manufacture

Solution Approach 1:

The invention segments the reactant mixture into distinct components with specific carbon atom spacings (binary, unary, ternary, quaternary). By controlling the presence and ratios of these segmented components, the process can be tailored to produce specific cyclic/acyclic amine mixtures suitable for different end uses, thereby achieving product customization without overly complicating the manufacturing approach.

Inventive Principle:

Principle #1Segmentation

Solution Approach 2:

The invention employs parameter changes by adjusting the carbon atom spacing distribution and molar ratios of reactants to control product composition. By varying these parameters, the process can be optimized for different applications (e.g., epoxy curing vs. lube oil additives) while maintaining a relatively simple manufacturing framework.

Inventive Principle:

Principle #35Parameter changes

2Quantity of substance

If transamination processes are used to produce cyclic amines, then cyclic content can be increased, but control over cyclic/acyclic mixture composition is difficult

Engineering Contradiction:

Improvecyclic amine contentVSAvoidcyclic/acyclic mixture control

Core Design Contradiction:

Quantity of substanceVSManufacturing precision

Solution Approach 1:

The invention applies preliminary action by pre-configuring the reactant mixture with specific carbon atom spacings before the transamination reaction occurs. This preliminary setup ensures that the reaction naturally produces the desired cyclic/acyclic ratio, providing precise control over product composition without requiring complex post-reaction adjustments.

Inventive Principle:

Principle #10Preliminary action

Solution Approach 2:

By changing the parameters of carbon atom spacing distribution in the reactants, the process precisely controls the cyclic/acyclic amine ratio in the product mixture, achieving both high cyclic content and precise compositional control.

Inventive Principle:

Principle #35Parameter changes

3Productivity

If transamination processes are used, then amine products can be manufactured, but yields are low and byproduct salts are produced that require disposal

Engineering Contradiction:

Improveamine production yieldVSAvoidbyproduct salt formation

Core Design Contradiction:

ProductivityVSLoss of substance

Solution Approach 1:

The invention optimizes reaction parameters including carbon atom spacing distribution, molar ratios, temperature, pressure, and catalyst selection to maximize amine production yield while minimizing byproduct salt formation. These parameter changes lead to both improved productivity and reduced substance loss.

Inventive Principle:

Principle #35Parameter changes

Applied Scientific Principles

This section explains which scientific principles are used to turn an abstract innovation direction into a practical engineering solution.

Function Achieved in This Case

This approach provides improved control over the composition of polyamine products, enabling the production of high cyclic content materials suitable for applications like epoxy curing and fuel additives, while minimizing byproducts and increasing yield.

Implementation Method 1

Transamination is a transfer of an amino group from one chemical compound to another, or the transposition of an amino group within a chemical compound

Methodology Applied

Scientific EffectTransamination: Chemical Bonding

Implementation Method 2

using hydrogenation/dehydrogenation catalysts to optimize product composition

Methodology Applied

Scientific EffectHydrogenation: Hydrogenation

Data Source

PatentEP2638020B1Transamination of nitrogen-containing compounds to make cyclic and cyclic/acyclic polyamine mixtures

Publication Date: 2016.09.07 DOW GLOBAL TECHNOLOGIES LLC

AI summary

A transamination process is described to prepare polyamine product mixtures from reactants comprising mixed nitrogen-containing compounds with binary carbon spacing between nitrogen-containing groups (a binary component). A second nitrogen-containing component with a second carbon atom spacing between nitrogen-containing groups may also be employed. The molar ratio between the binary and second components can be adjusted to customize the product composition for desired end uses.