Tin-Modified Catalyst for Selective Amine Synthesis

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Solution Overview

Problem

Existing catalysts for the amination of alcohols, aldehydes, and ketones suffer from increased decarbonylation at elevated temperatures, leading to 'runaway hazards' and the formation of undesirable by-products like methane, methoxyethanol, and methoxyethylamine, which reduce the yield of economically valuable products such as aminodiglycol and morpholine.

Innovation Solution

A supported catalyst comprising oxygen-containing compounds of aluminum, copper, nickel, cobalt, and tin, with a specific composition range of 15-80% Al2O3, 1-20% CuO, 5-35% NiO, 5-35% CoO, and 0.2-5.0% SnO, before hydrogen reduction, is used to enhance the selectivity and stability of the amination process.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Productivity

If elevated temperatures are used to increase reaction rate, then productivity is improved, but decarbonylation increases leading to runaway hazards and unwanted by-products

Engineering Contradiction:
Improvereaction rateVSAvoiddecarbonylation
Core Design Contradiction:
ProductivityVSObject-affected harmful factors

Solution Approach 1:

The invention changes the chemical composition parameters of the catalyst by incorporating specific amounts of tin (0.2-5.0% SnO), aluminum (15-80% Al2O3), copper (1-20% CuO), nickel (5-35% NiO), and cobalt (5-35% CoO). This compositional parameter change allows the catalyst to function effectively at lower temperatures, thereby increasing productivity while reducing decarbonylation and associated hazards.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention uses a composite catalyst material combining multiple metal oxides (SnO, Al2O3, CuO, NiO, CoO) with specific weight ratios. This composite structure creates synergistic effects where the combination of metals provides both high activity for the desired amination reaction and selectivity to suppress decarbonylation, enabling safe operation at optimized temperatures.

Inventive Principle:
Principle #40Composite materials

2Productivity

If conventional catalysts are used, then the amination process can proceed, but the yield of economically valuable products is reduced due to formation of by-products

Engineering Contradiction:
Improveproduct yieldVSAvoidby-product formation
Core Design Contradiction:
ProductivityVSLoss of substance

Solution Approach 1:

The invention optimizes the catalyst composition parameters with precise weight percentages of multiple metal oxides, particularly incorporating tin (0.2-5.0% SnO) which acts as a selective promoter. This parameter optimization shifts the reaction selectivity toward the desired amination products (aminodiglycol and morpholine) while suppressing side reactions that produce unwanted by-products like methoxyethanol and methoxyethylamine.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention converts the potential harm of tin addition (which could potentially cause unwanted side reactions) into a benefit by carefully controlling the tin content at low levels (0.2-5.0% SnO). At this optimized concentration, tin acts as a selective promoter that enhances the desired amination reaction while suppressing decarbonylation and other harmful side reactions, thereby improving product yield and reducing by-product formation.

Inventive Principle:
Principle #22Blessing in disguise (Convert harm into benefit)

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 catalysts exhibit improved mechanical stability, reduced decarbonylation, and increased selectivity for linear products like aminodiglycol, while maintaining high activity and yield of economically interesting products like morpholine, thus addressing the issues of process safety and product quality.

Implementation Method 1

a supported catalyst containing copper, nickel and cobalt

Methodology Applied
Scientific EffectCatalysis: Catalysis

Implementation Method 2

before its reduction with hydrogen

Methodology Applied
Scientific EffectReduction: Reduction

Data Source

PatentEP2506966B1Catalyst and method for producing an amine
Publication Date: 2017.08.16 BASF SE
  • EP2506966B1 patent drawing
  • EP2506966B1 patent drawing
  • EP2506966B1 patent drawing

AI summary

The invention relates to a method for producing an amine by reacting a primary or secondary alcohol, aldehyde and/or ketone with hydrogen and a nitrogen compound, selected from the group containing ammonia and primary and secondary amines, in the presence of a supported catalyst that contains copper, nickel and cobalt. According to the invention, the catalytically active mass of the catalyst, prior to the reduction of the same using hydrogen, contains oxygen-containing compounds of aluminium, copper, nickel and cobalt and an amount ranging between 0.2 and 5.0 wt. % of oxygen-containing compounds of tin, calculated as SnO. The invention also relates to catalysts defined as above.