Nitrile Hydrogenation Catalyst Pretreatment to Suppress Condensation

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Solution Overview

Problem

Existing methods for producing primary amines through the hydrogenation of nitriles face challenges in preventing side reactions that result in the formation of secondary and tertiary amines, leading to reduced yields and increased complexity in catalyst pretreatment and waste management.

Innovation Solution

Pretreating the hydrogenation catalyst with hydrocarbon compounds, natural gas, alcohols, ethers, or esters at elevated temperatures before use in the hydrogenation process to prevent side reactions and enhance the yield of primary amines.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Productivity

If hydrogenation is conducted using conventional catalysts without pretreatment, then the process is simple, but side reactions occur leading to formation of secondary and tertiary amines reducing primary amine yield

Engineering Contradiction:
Improveprimary amine yieldVSAvoidcatalyst pretreatment process
Core Design Contradiction:
ProductivityVSDevice complexity

Solution Approach 1:

The catalyst is subjected to pretreatment with hydrocarbon compounds, natural gas, alcohols, ethers, or esters at elevated temperatures before use in the hydrogenation process. This preliminary action modifies the catalyst surface properties to prevent side reactions during the main hydrogenation process, thereby increasing primary amine yield without requiring complex additional equipment.

Inventive Principle:
Principle #10Preliminary action

2Productivity

If hydrogenation is conducted in ammonia solvent to prevent condensation, then primary amine yield improves, but pressure-resistant apparatus is required due to high vapor pressure of ammonia

Engineering Contradiction:
Improveprimary amine yieldVSAvoidpressure-resistant apparatus
Core Design Contradiction:
ProductivityVSDevice complexity

Solution Approach 1:

The invention uses conventional catalysts that can be easily replaced or regenerated, rather than requiring expensive and complex pressure-resistant apparatus. The catalyst pretreatment creates a protective surface layer that prevents condensation reactions, allowing the use of simpler reaction vessels without needing to withstand high ammonia pressures.

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

3Productivity

If alkali metal hydroxide is used to prevent condensation products, then primary amine yield improves, but waste liquid treatment becomes difficult

Engineering Contradiction:
Improveprimary amine yieldVSAvoidwaste liquid treatment
Core Design Contradiction:
ProductivityVSEase of manufacture

Solution Approach 1:

The invention employs conventional catalysts that do not require alkali metal hydroxides for operation. The catalyst pretreatment with hydrocarbon compounds, natural gas, alcohols, ethers, or esters creates a protective surface layer that prevents condensation reactions, eliminating the need for alkali metal hydroxides and their associated waste treatment problems.

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

4Productivity

If catalyst is pretreated with formaldehyde or alkali carbonate in aqueous solution, then side reactions are reduced, but additional pretreatment step and water removal operation are required

Engineering Contradiction:
Improveprimary amine yieldVSAvoidpretreatment process steps
Core Design Contradiction:
ProductivityVSDevice complexity

Solution Approach 1:

The invention changes the pretreatment parameters by using hydrocarbon compounds, natural gas, alcohols, ethers, or esters as treating agents instead of formaldehyde or alkali carbonate. This parameter change allows the pretreatment to be performed directly without requiring aqueous solutions, thereby eliminating the need for water removal operations while still achieving the goal of reducing side reactions.

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

The pretreatment method significantly reduces the production of condensation products, increasing the yield of primary amines by 15% to 50% or more compared to untreated catalysts, while simplifying the process and reducing operational complexity.

Implementation Method 1

Pretreating the hydrogenation catalyst with hydrocarbon compounds, natural gas, alcohols, ethers, or esters at elevated temperatures before use in the hydrogenation process

Methodology Applied
Scientific EffectThermal treatment: Heat Treatment

Implementation Method 2

The production of primary amines by the hydrogenation of nitriles in the presence of a hydrogenation catalyst containing a metal selected from nickel, cobalt and iron

Methodology Applied
Scientific EffectCatalysis: Catalysis

Implementation Method 3

The production of primary amines by the hydrogenation of nitriles

Methodology Applied
Scientific EffectHydrogenation: Hydrogenation

Data Source

PatentEP1900428B1Production method of primary amines and catalysts for producing primary amines
Publication Date: 2016.01.06 MITSUBISHI GAS CHEM CO INC

AI summary

A method of producing a primary amine by the hydrogenation of a nitrile in the presence of a hydrogenation catalyst. The hydrogenation catalyst contains at least one metal selected from the group consisting of nickel, cobalt and iron. Before use in the hydrogenation of nitrile, the hydrogenation catalyst is pretreated with at least one treating agent selected from the group consisting of hydrocarbons, alcohols, ethers, esters and carbon monoxide at 150 to 500 °C.