Semibatch Amine Synthesis via Suspension Catalyst

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Solution Overview

Problem

Existing processes for producing amines by reacting aldehydes or ketones with hydrogen and nitrogen compounds often result in low selectivity and require complex catalyst handling, leading to increased costs and reduced efficiency.

Innovation Solution

A semibatch process using a suspension catalyst where the nitrogen compound is introduced first, and the aldehyde or ketone is added continuously until a high conversion of 95% is achieved, with the catalyst remaining in the reaction vessel for reuse, minimizing by-product formation and simplifying catalyst management.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Manufacturing precision

If a fixed bed catalyst is used in high-pressure processes, then the reaction can be carried out with good conversion, but the catalyst handling becomes complex and selectivity decreases due to aldol by-products

Engineering Contradiction:
ImproveselectivityVSAvoidcatalyst handling
Core Design Contradiction:
Manufacturing precisionVSDevice complexity

Solution Approach 1:

The patent changes the operating pressure from high-pressure (fixed bed) processes to low-pressure conditions, and changes the catalyst form from fixed bed to suspension catalyst. This parameter change allows the reaction to proceed with high selectivity while simplifying catalyst handling, as the suspension catalyst can be easily separated by filtration rather than requiring complex fixed bed systems

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent employs a suspension catalyst that can be easily filtered and discarded after use, rather than requiring expensive, complex fixed bed catalyst systems. The simple filtration process makes catalyst replacement economical and straightforward, effectively treating the catalyst as a consumable item that simplifies overall process design

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

2Manufacturing precision

If aldehyde or ketone is added in excess to achieve high conversion of nitrogen compound, then conversion increases, but by-product formation from aldol reaction increases

Engineering Contradiction:
ImproveconversionVSAvoidby-product formation
Core Design Contradiction:
Manufacturing precisionVSObject-generated harmful factors

Solution Approach 1:

The patent implements a feedback-controlled addition process where the aldehyde or ketone is added continuously or in portions while monitoring the conversion of the nitrogen compound. This feedback mechanism ensures that the carbonyl compound is added at the optimal rate to maintain high conversion while preventing excess accumulation that would lead to aldol by-product formation

Inventive Principle:
Principle #23Feedback

Solution Approach 2:

The patent uses periodic or continuous addition of the carbonyl compound rather than adding it all at once. This periodic action allows the reaction to proceed with maintained selectivity by keeping the concentration of carbonyl compound at appropriate levels throughout the reaction, preventing aldol condensation while achieving high conversion

Inventive Principle:
Principle #19Periodic action

3Ease of manufacture

If catalyst is removed from reaction vessel after reaction, then product separation is achieved, but catalyst cannot be reused and costs increase

Engineering Contradiction:
Improveproduct separationVSAvoidcatalyst consumption
Core Design Contradiction:
Ease of manufactureVSLoss of substance

Solution Approach 1:

The patent implements a system where the catalyst is easily separated by filtration (discarding from the product stream) and then recovered for reuse in subsequent reactions. This approach maintains simple product separation while preventing catalyst loss, directly addressing both aspects of the contradiction

Inventive Principle:
Principle #34Discarding and recovering

Solution Approach 2:

The patent enables continuous reuse of the catalyst across multiple reaction batches. After filtration and recovery, the catalyst is reused in subsequent reactions, maintaining its useful catalytic action continuously over time. This eliminates the need for fresh catalyst in each batch while keeping the separation process simple

Inventive Principle:
Principle #20Continuity of useful action

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 enhances selectivity and yield, reduces catalyst consumption, and allows for consistent product quality over time, simplifying processing and reducing manufacturing costs.

Implementation Method 1

reacting an aldehyde and/or ketone with hydrogen and a nitrogen compound, selected from the group of primary and secondary amines, in the presence of a heterogeneous catalyst

Methodology Applied
Scientific EffectCatalysis: Catalysis

Implementation Method 2

using a suspension catalyst as Heterogeneous catalyst takes place

Methodology Applied
Scientific EffectAdsorption: Adsorption

Data Source

PatentEP2029521B1Process for the preparation of an amine
Publication Date: 2012.07.11 BASF SE
  • EP2029521B1 patent drawing
  • EP2029521B1 patent drawing
  • EP2029521B1 patent drawing

AI summary

A process for the preparation of an amine by reacting an aldehyde and/or ketone with hydrogen and a nitrogen compound selected from the group of primary and secondary amines in the presence of a heterogeneous catalyst, characterized in that the reaction takes place using a suspension catalyst as a heterogeneous catalyst and is carried out in a semibatch operating mode in which the nitrogen compound is provided as a reactant in the reaction vessel and the aldehyde and/or the ketone is added as the other reactant in the course of the reaction, and in the course of the reaction depending on the attained rate of conversion of the nitrogen compound, the aldehyde and/or the ketone is added in portions or continuously to the reaction mixture until a rate of conversion of the nitrogen compound of at least 95 % results, and the catalyst remains in whole or in part in the reaction vessel after the reaction batch for another use in the next reaction batch.