Ethyleneamine Production via MEG Amination and Ammonia Separation

Resolve Bottlenecks,
Find Innovative Solutions
Generate Solutions

Solution Overview

Problem

The production of ethylenediamine (EDA) from monoethylene glycol (MEG) faces challenges due to the complexity of handling ethylene oxide, the need for separate distillation of by-products, and inefficiencies in energy and resource usage, particularly in the separation of ammonia and hydrogen from reaction effluents.

Innovation Solution

A process involving the reaction of MEG with ammonia in the presence of hydrogen and a heterogeneous catalyst, followed by a redesigned ammonia separation method that includes condensation and scrubbing with MEG to enrich ammonia and hydrogen, allowing for efficient separation and reuse of resources.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If MEG is reacted with ammonia in the presence of ethylene oxide to produce EDA, then the reaction can proceed, but the selectivity decreases and byproducts such as diethanolamine and triethanolamine are formed

Engineering Contradiction:
Improvereaction successVSAvoidselectivity
Core Design Contradiction:
ReliabilityVSManufacturing precision

Solution Approach 1:

The patent removes ethylene oxide from the reaction system and replaces it with MEG as the sole carbon source. This extraction of the problematic intermediate eliminates the formation of higher ethanolamine byproducts while maintaining EDA production through direct amination of MEG.

Inventive Principle:
Principle #2Taking out (Extraction)

Solution Approach 2:

The patent changes the reaction parameters by using a specific catalyst system (copper-containing catalyst) and controlling temperature (150-350°C) and pressure (3-30 bar) to achieve high selectivity for EDA from MEG without forming significant amounts of byproducts.

Inventive Principle:
Principle #35Parameter changes

2Reliability

If ethylene oxide is handled in the production process, then the reaction can proceed, but safety risks increase due to flammability and explosion hazards

Engineering Contradiction:
Improvereaction capabilityVSAvoidsafety risk
Core Design Contradiction:
ReliabilityVSObject-affected harmful factors

Solution Approach 1:

The patent extracts ethylene oxide from the process entirely, using MEG instead as the reactant. This eliminates the safety hazards associated with handling and storing ethylene oxide while maintaining the ability to produce EDA through alternative reaction pathways.

Inventive Principle:
Principle #2Taking out (Extraction)

3Productivity

If MEA is produced by reacting ethylene oxide with ammonia, then the reaction proceeds, but additional distillation steps are required to separate byproducts

Engineering Contradiction:
Improveproduction capabilityVSAvoidprocess complexity
Core Design Contradiction:
ProductivityVSDevice complexity

Solution Approach 1:

The patent removes the intermediate MEA production step and the associated distillation requirements by directly converting MEG to EDA in a single reaction step, thereby simplifying the overall process flow and reducing equipment complexity.

Inventive Principle:
Principle #2Taking out (Extraction)

4Reliability

If conventional ammonia and hydrogen separation methods are used, then separation can be achieved, but energy consumption increases

Engineering Contradiction:
Improveseparation effectivenessVSAvoidenergy consumption
Core Design Contradiction:
ReliabilityVSUse of energy by moving object

Solution Approach 1:

The patent employs a scrubbing system where the reaction effluent itself is used to absorb and separate ammonia and hydrogen through condensation and washing steps, eliminating the need for energy-intensive conventional separation methods and enabling resource reuse within the process.

Inventive Principle:
Principle #25Self-service

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 process enhances resource efficiency by preheating MEG and reducing energy consumption, enabling the use of MEG without fiber quality and minimizing the need for further purification of washing liquids, while achieving high selectivity and purity of EDA and other ethylene amines.

Implementation Method 1

Passing the gaseous phase from stage 2-1) over one or more condensers, yielding one or more liquid phases enriched with ammonia and a gaseous phase enriched with hydrogen

Methodology Applied
Scientific EffectCondensation: Condensation

Implementation Method 2

Contacting the gaseous phase from stage 2-2) with MEG, yielding a liquid phase containing MEG and ammonia and a gaseous phase containing hydrogen and optionally ammonia

Methodology Applied
Scientific EffectAbsorption: Absorption (physical)

Implementation Method 3

Reaction of MEG with ammonia in the presence of hydrogen and an amination catalyst

Methodology Applied
Scientific EffectCatalysis: Catalysis

Data Source

PatentEP3700884B1Process for the preparation of ethyleneamines
Publication Date: 2021.10.13 BASF SE
  • EP3700884B1 patent drawingFigure 1
  • EP3700884B1 patent drawingFigure 2
  • EP3700884B1 patent drawingFigure 3

AI summary

The invention relates to a method for producing ethyleneamines and/or alkanolamines, having the following steps: 1) reacting MEG with ammonia in the presence of hydrogen and an amination catalyst; and 2) separating hydrogen and ammonia from the reaction product from stage 1. The invention is characterized in that the separation of hydrogen and ammonia carried out in stage 2 has the steps of: 2-1) separating the reaction product from stage 1 into a gaseous phase, which contains ammonia and hydrogen, and a liquid phase, which contains ethyleneamines and/or alkanolamines, 2-2) passing the gaseous phase from stage 2-1) over one or more condensers, wherein one or more liquid phases are obtained in which ammonia is enriched, and a gaseous phase is obtained in which hydrogen is enriched, and 2-3) bringing the gaseous phase from stage 2-2) into contact with MEG such that a liquid phase containing MEG and ammonia is obtained and a gaseous phase containing hydrogen and optionally ammonia is obtained.