Raney Nickel Pretreatment for Reduced DCH in Adiponitrile Hydrogenation

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Solution Overview

Problem

Existing processes for the hydrogenation of adiponitrile to hexamethylenediamine using Raney nickel catalysts suffer from high formation of diaminocyclohexane (DCH) as a side product, making separation difficult and increasing purification costs and energy consumption.

Innovation Solution

The use of a Raney nickel catalyst modified by pre-treatment with carbon monoxide or carbon dioxide in a liquid medium, either prior to or during hydrogenation, to reduce DCH formation.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Productivity

If Raney nickel catalyst is used for hydrogenation of adiponitrile, then catalytic activity is achieved, but diaminocyclohexane formation increases

Engineering Contradiction:
Improvecatalytic activityVSAvoiddiaminocyclohexane formation
Core Design Contradiction:
ProductivityVSObject-generated harmful factors

Solution Approach 1:

The Raney nickel catalyst is pre-treated with carbon monoxide or carbon dioxide in a liquid medium before use in the hydrogenation reaction. This preliminary treatment modifies the catalyst surface properties to reduce its ability to catalyze the formation of diaminocyclohexane while maintaining its activity for hexamethylenediamine production

Inventive Principle:
Principle #10Preliminary action

Solution Approach 2:

The invention changes the physical-chemical parameters of the catalyst by exposing it to carbon monoxide or carbon dioxide in a liquid medium. This treatment alters the catalyst's surface characteristics and electronic properties, thereby changing its selectivity to favor hexamethylenediamine formation over diaminocyclohexane formation

Inventive Principle:
Principle #35Parameter changes

2Productivity

If diaminocyclohexane is formed as side product, then hydrogenation reaction proceeds, but separation difficulty increases

Engineering Contradiction:
Improvehydrogenation reaction rateVSAvoidpurification complexity
Core Design Contradiction:
ProductivityVSDevice complexity

Solution Approach 1:

The catalyst is pre-treated to prevent or reduce the formation of diaminocyclohexane before the main hydrogenation reaction occurs. By modifying the catalyst properties in advance, the harmful side reaction is suppressed, avoiding the creation of separation problems downstream

Inventive Principle:
Principle #9Preliminary anti-action

3Productivity

If conventional hydrogenation process is used, then hexamethylenediamine is produced, but purification costs increase

Engineering Contradiction:
Improvehexamethylenediamine productionVSAvoidpurification energy consumption
Core Design Contradiction:
ProductivityVSLoss of energy

Solution Approach 1:

The catalyst undergoes preliminary treatment with carbon monoxide or carbon dioxide to establish selective properties before the hydrogenation reaction. This pre-modification ensures that the reaction produces minimal diaminocyclohexane, thereby reducing the energy and cost requirements for subsequent purification steps

Inventive Principle:
Principle #10Preliminary 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

Significantly reduces DCH formation, improving catalyst selectivity and maintaining catalytic activity, thereby facilitating easier purification of hexamethylenediamine with reduced capital and energy costs.

Implementation Method 1

hydrogenation of adiponitrile in the presence of a Raney nickel catalyst

Methodology Applied
Scientific EffectHydrogenation: Hydrogenation

Implementation Method 2

hydrogenation of adiponitrile to give a cyclic diamine, diaminocyclohexane (DCH)... in the presence of a catalyst based on optionally doped Raney nickel

Methodology Applied
Scientific EffectCatalysis: Catalysis

Data Source

PatentUS12415775B2Process for the preparation of hexamethylenediamine by hydrogenation of adiponitrile with reduced formation of diaminocyclohexane
Publication Date: 2025.09.16 BASF SE

AI summary

The present invention relates to a process for the preparation of hexamethylenediamine by hydrogenation of adiponitrile in the presence of a Raney nickel catalyst, wherein a Raney nickel catalyst modified by treatment with carbon monoxide or carbon dioxide in a liquid medium is used.