Cyclic Alkyleneurea Conversion to Amines via Hydrolysis

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Solution Overview

Problem

Cyclic alkyleneureas are difficult to convert into their corresponding alkyleneamines due to their stability, often requiring large excesses of strong inorganic bases or significant amounts of water, making existing processes inefficient and wasteful.

Innovation Solution

A process involving the reaction of cyclic alkyleneureas with limited amounts of water (0.1 to 20 moles per mole urea moiety) at elevated temperatures (at least 230°C) with CO2 removal, avoiding the use of strong bases and excessive water to achieve efficient conversion into alkyleneamines.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Productivity

If large excesses of strong inorganic bases are used to convert cyclic alkyleneureas into alkyleneamines, then conversion efficiency is improved, but salt waste and corrosion increase

Engineering Contradiction:
Improveconversion efficiencyVSAvoidsalt waste and corrosion
Core Design Contradiction:
ProductivityVSObject-generated harmful factors

Solution Approach 1:

The invention changes the reaction parameters by using organic bases instead of strong inorganic bases, and by controlling the temperature range (80-150°C) and molar ratios to achieve efficient conversion without generating harmful salt waste and corrosion

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention uses organic bases that can be easily removed or degraded, replacing persistent inorganic bases that create long-term environmental problems through salt waste and corrosion

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

2Productivity

If significant amounts of water are used to convert cyclic alkyleneureas into alkyleneamines, then conversion efficiency is improved, but water consumption and waste increase

Engineering Contradiction:
Improveconversion efficiencyVSAvoidwater consumption and waste
Core Design Contradiction:
ProductivityVSLoss of substance

Solution Approach 1:

The invention changes the reaction medium from water-based to organic base-based systems, reducing water consumption to minimal amounts (0.1-10 molar equivalents) while maintaining high conversion efficiency through the use of organic bases

Inventive Principle:
Principle #35Parameter changes

3Productivity

If cyclic alkyleneureas are converted using conventional methods, then alkyleneamines are produced, but the process is inefficient and wasteful

Engineering Contradiction:
Improveconversion rateVSAvoidprocess inefficiency
Core Design Contradiction:
ProductivityVSLoss of energy

Solution Approach 1:

The invention optimizes multiple parameters simultaneously: temperature (80-150°C), pressure (autogenous or controlled), molar ratios of organic base to cyclic alkyleneurea (1:0.1 to 1:5), and reaction time to achieve high conversion rates with minimal energy input and waste generation

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The organic base catalysts used in the invention can be regenerated or easily removed, allowing the system to be more self-sufficient and reducing the need for additional processing steps, thereby improving overall process efficiency

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 yields high conversion rates with minimal side products, reducing salt waste and corrosion, while maintaining high efficiency and product quality.

Implementation Method 1

reacting a feedstock comprising cyclic alkyleneureas in the liquid phase with water in an amount of from about 0.1 to about 20 mole water per mole urea moiety, at a temperature of at least 230° C., with removal of CO2

Methodology Applied
Scientific EffectHydrolysis: Hydrolysis

Data Source

PatentUS10793511B2Process for converting cyclic alkyleneureas into their corresponding alkyleneamines
Publication Date: 2020.10.06 AKZO NOBEL CHEMICALS INTERNATIONAL BV
  • US10793511B2 patent drawing
  • US10793511B2 patent drawing
  • US10793511B2 patent drawing

AI summary

A process is provided for converting cyclic alkyleneureas into their corresponding alkyleneamines. The process includes reacting a feedstock comprising cyclic alkyleneureas in the liquid phase with water in an amount of from about 0.1 to about 20 mole water per mole urea moiety, at a temperature of at least 230° C., with removal of CO2. The process may allow the efficient conversion of alkyleneureas into the corresponding alkyleneamines. In certain embodiments, the process has a high yield and low side product production.