Cyclic Monourea Conversion to Ethylene Amine

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Solution Overview

Problem

Existing methods for converting cyclic monourea ethylene amine compounds into their corresponding ethylene amine compounds are inefficient, often requiring strong bases or acids that can lead to degradation and do not effectively separate urea-free molecules.

Innovation Solution

A reactive separation process using a reaction mixture with cyclic monourea ethylene amine compounds, where one molecule transfers its urea unit to another, allowing for the separation of urea-free ethylene amine compounds under mild conditions, utilizing differences in boiling points and vapor phase transfer, with minimal water content and no need for additional adjuvants.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Productivity

If strong bases or acids are used to convert cyclic monourea ethylene amine compounds into ethylene amine compounds, then the conversion can proceed, but degradation of the ethylene amine compound occurs and separation of urea-free molecules is ineffective

Engineering Contradiction:
Improveconversion efficiencyVSAvoiddegradation
Core Design Contradiction:
ProductivityVSObject-affected harmful factors

Solution Approach 1:

The invention changes the pH parameter from extreme values (strong bases/acids) to mild conditions (pH 6-8), enabling effective conversion while preventing degradation. This parameter optimization resolves the contradiction between achieving high conversion efficiency and avoiding harmful degradation effects.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention introduces a specific amine compound as an intermediary substance that facilitates the conversion reaction under mild conditions. This intermediary enables the reaction to proceed without requiring strong bases or acids, thus avoiding degradation while maintaining productivity.

Inventive Principle:
Principle #24Intermediary (Mediator)

2Productivity

If conventional conversion methods are used, then some conversion occurs, but separation of urea-free ethylene amine compounds is not achieved

Engineering Contradiction:
Improveconversion rateVSAvoidseparation efficiency
Core Design Contradiction:
ProductivityVSManufacturing precision

Solution Approach 1:

The invention merges the conversion reaction and separation process into a single integrated operation. By conducting the reaction at controlled pH with specific amine compounds, the urea-free products are generated in a form that allows direct separation, combining two previously separate steps into one efficient process.

Inventive Principle:
Principle #5Merging (Combining)

Solution Approach 2:

The invention optimizes pH and temperature parameters to simultaneously achieve high conversion rates and effective separation. By maintaining pH 6-8 and controlling temperature, the process ensures both complete conversion and optimal separation of urea-free compounds from the reaction mixture.

Inventive Principle:
Principle #35Parameter changes

3Manufacturing precision

If high temperatures are used for separation, then separation can be achieved, but degradation of ethylene amine compounds increases

Engineering Contradiction:
Improveseparation efficiencyVSAvoidthermal degradation
Core Design Contradiction:
Manufacturing precisionVSObject-affected harmful factors

Solution Approach 1:

The invention changes the temperature parameter from high values to moderate ranges (50-150°C), achieving effective separation through controlled thermal conditions rather than excessive heat. This parameter optimization allows separation to proceed while minimizing thermal degradation of the ethylene amine compounds.

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

This process efficiently converts cyclic monourea ethylene amine compounds into ethylene amine compounds with high yield and minimal degradation, allowing for the separation of urea-free compounds at low temperatures and recovering alkylene diurea products, while avoiding the use of strong bases or acids.

Implementation Method 1

one cyclic monourea (U-EA) reacts with another cyclic monourea (U-EA) to transfer its urea unit thereto

Methodology Applied
Scientific EffectUrea transfer reaction: Chemical Bonding

Implementation Method 2

the obtained ethylene amine compound (EA) without urea unit is separated from the reaction mixture, wherein the reaction is done in less than 10 wt% of water on the basis of total weight of the reaction mixture

Methodology Applied
Scientific EffectDistillation: Distillation

Implementation Method 3

urea transfer between molecules finds place under conditions at which part of the reaction mixture is transferred to the vapor phase

Methodology Applied
Scientific EffectVapor phase transfer: Evaporation

Implementation Method 4

the boiling point of any U-EA, such as UTETA or UTEPA, is higher than that of the corresponding EA, such as TETA or TEPA respectively

Methodology Applied
Scientific EffectPhase change: Phase Change

Data Source

PatentEP3665159B1Process to convert the cyclic monourea of an ethylene amine compound into the ethylene amine compound
Publication Date: 2022.12.28 AKZO NOBEL CHEMICALS INTERNATIONAL BV
  • EP3665159B1 patent drawing
  • EP3665159B1 patent drawing

AI summary

The present invention relates to a process to convert the cyclic monourea of ethylene amine compounds (U-EA) into ethylene amine compound (EA) by performing a reactive separation step using a reaction mixture containing the cyclic monourea, wherein one cyclic monourea (U-EA) reacts with another cyclic monourea (U-EA) to transfer its urea unit thereto and the obtained ethylene amine compound (EA) without urea unit is separated from the reaction mixture.