Single-Step Secondary And Tertiary Amine Synthesis Without Hazardous Reagents

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Solution Overview

Problem

Existing methods for producing alkylated bis-(N,N-dimethylaminoethoxyethyl) amine catalysts are cumbersome and involve multiple steps, while using chlorinated sulfur and/or phosphorous-based products that are hazardous and not suitable for large-scale, economically viable processes.

Innovation Solution

A method involving a single-step reaction of alcohol and amine in the presence of hydrogen and a catalyst, such as copper-chromite, to produce secondary or tertiary amines, which can be used as catalysts for polyurethane materials and other applications.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Ease of manufacture

If existing methods are used to produce alkylated bis-(N,N-dimethylaminoethoxyethyl) amine catalysts, then the catalysts can be produced, but the process involves multiple steps and uses hazardous chlorinated sulfur and/or phosphorous-based products

Engineering Contradiction:
Improvemanufacturing process simplicityVSAvoidhazardous chemicals
Core Design Contradiction:
Ease of manufactureVSObject-affected harmful factors

Solution Approach 1:

The invention extracts and removes the hazardous chlorinated sulfur and phosphorous-based components from the synthesis process. The new method uses only alcohol and amine reactants without any chlorine, sulfur, or phosphorous compounds, eliminating the harmful factors while maintaining catalyst production capability

Inventive Principle:
Principle #2Taking out (Extraction)

Solution Approach 2:

The invention changes the chemical parameters of the reaction system by substituting hazardous reagents with safe alternatives. The process uses alcohol and amine with specific molecular structures (formula I and II) that react to form the desired catalyst without requiring dangerous intermediates or conditions

Inventive Principle:
Principle #35Parameter changes

2Manufacturing precision

If existing multi-step methods are used, then the catalysts can be produced with higher purity, but the process is cumbersome and not economically viable for large scale

Engineering Contradiction:
Improvecatalyst purityVSAvoidproduction efficiency
Core Design Contradiction:
Manufacturing precisionVSProductivity

Solution Approach 1:

The invention merges multiple synthesis steps into a single direct reaction. The alcohol and amine reactants are combined in one step to directly form the alkylated bis-(N,N-dimethylaminoethoxyethyl) amine catalyst, eliminating intermediate purification steps while maintaining high purity through the inherent selectivity of the reaction

Inventive Principle:
Principle #5Merging (Combining)

Solution Approach 2:

The invention segments the molecular structure into specific alcohol (formula I) and amine (formula II) components that can be independently optimized and then combined in a single reaction step, allowing for precise control of the final catalyst structure without complex multi-step synthesis

Inventive Principle:
Principle #1Segmentation

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 method enables the production of alkylated bis-(N,N-dimethylaminoethoxyethyl) amine catalysts in economically acceptable quantities with fewer steps, reducing hazards and costs, and improving the efficiency of polyurethane production.

Implementation Method 1

reacting at least one alcohol represented by formula (1) with at least one amine represented by formula (2) in the presence of hydrogen and a catalyst

Methodology Applied
Scientific EffectCatalysis: Catalysis

Data Source

PatentUS20250333372A1Method for producing secondary and tertiary amines
Publication Date: 2025.10.30 HUNTSMAN PETROCHEMICAL LLC
  • US20250333372A1 patent drawing
  • US20250333372A1 patent drawing
  • US20250333372A1 patent drawing

AI summary

The present disclosure relates to a method for producing a secondary amine or tertiary amine or mixture thereof in a single reaction step and the use of such amines in various applications including, but not limited to, polyurethane, oil & gas, metalworking, paints and other coatings applications.