Heterogeneous Catalyst Synthesis of Primary Isohexide Amines

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Solution Overview

Problem

Current methods for producing isohexide amines are inefficient for large-scale production due to the use of expensive noble metal complexes, complex synthesis processes, and challenging reaction conditions, making it difficult to scale up the production of biogenic amines for industrial applications.

Innovation Solution

A process using heterogeneous catalysis with commercially available hydrogenation catalysts, such as Ru/C, to convert dianhydrohexitols into primary amines under mild reaction conditions in aqueous solutions or solvent-free systems, allowing for the separation of catalysts and enabling industrial-scale production.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If homogeneous catalysis with noble metal complexes is used, then the amination reaction can proceed, but the catalyst is expensive, sensitive to air and water, and difficult to separate from the product

Engineering Contradiction:
Improvecatalyst activityVSAvoidcatalyst separation and cost
Core Design Contradiction:
ReliabilityVSEase of manufacture

Solution Approach 1:

The patent replaces expensive noble metal complexes with inexpensive heterogeneous catalysts such as metal oxides (e.g., tungsten oxide, molybdenum oxide) or activated carbon. These alternative catalysts are significantly cheaper, more stable towards air and water, and can be easily separated from the product mixture through filtration, thereby resolving the contradictions of cost, stability, and separation difficulty.

Inventive Principle:
Principle #27Cheap short-living objects (Disposable)

Solution Approach 2:

The patent transitions from homogeneous catalysis (molecular-level interaction) to heterogeneous catalysis (surface-level interaction). This substitution allows the catalyst to be in a different phase (solid) than the reactants (liquid or gas), enabling simple physical separation through filtration while maintaining catalytic activity through surface reactions.

Inventive Principle:
Principle #28Mechanics substitution (Replace mechanical system)

2Manufacturing precision

If uncatalyzed multi-stage syntheses are used, then the amination can be achieved, but the process requires highly reactive and toxic intermediates and cannot be scaled up

Engineering Contradiction:
Improveamination completionVSAvoidscale-up capability
Core Design Contradiction:
Manufacturing precisionVSProductivity

Solution Approach 1:

The patent introduces a catalyst as an intermediary substance that facilitates the amination reaction. The catalyst provides an alternative reaction pathway with lower activation energy, enabling the reaction to proceed under milder conditions without forming highly reactive and toxic intermediates. This intermediary approach makes the process safe and scalable for industrial production.

Inventive Principle:
Principle #24Intermediary (Mediator)

3Manufacturing precision

If laboratory-scale synthesis routes are used, then the amination can be performed, but the formation of stoichiometric amounts of by-products prevents scale-up

Engineering Contradiction:
Improvereaction completenessVSAvoidby-product formation
Core Design Contradiction:
Manufacturing precisionVSLoss of substance

Solution Approach 1:

The patent changes the reaction parameters by introducing a catalyst that selectively promotes the desired amination reaction while suppressing side reactions. This parameter change (adding catalyst) leads to higher selectivity and fewer stoichiometric by-products, enabling the process to be scaled up industrially without the waste management issues associated with laboratory methods.

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 method provides a scalable, economical, and selective process for producing isohexide amines, overcoming the limitations of previous methods by using readily available catalysts and simplifying reaction conditions, enabling the production of biogenic amines for use in plastics and other chemical products.

Implementation Method 1

the amination is carried out by means of heterogeneous catalysis using a hydrogenation catalyst in the presence of hydrogen

Methodology Applied
Scientific EffectHeterogeneous catalysis: Catalysis

Implementation Method 2

amination of the dianhydrohexitol by reacting with ammonia, wherein the amination is carried out by means of heterogeneous catalysis using a hydrogenation catalyst in the presence of hydrogen

Methodology Applied
Scientific EffectHydrogenation: Hydrogenation

Data Source

PatentEP3169689B1Method for the synthesis of primary isohexide amines
Publication Date: 2018.09.05 RWTH AACHEN UNIV
  • EP3169689B1 patent drawingFigure 1

AI summary

The invention relates to a method for synthesizing a primary amine, comprising the steps of: a) providing at least one dianhydrohexitol, and b) aminating the dianhydrohexitol by reacting same with ammonia, the amination being performed by heterogeneous catalysis using a hydrogenation catalyst in the presence of hydrogen.