Cyclic Alkylene Urea Conversion to Amines
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Solution Overview
Problem
Existing methods for converting cyclic alkylene ureas into their corresponding alkylene amines result in low product selectivities and yields due to degradation and the formation of undesirable by-products, such as salts, which complicate separation and lead to corrosion and storage stability issues.
Innovation Solution
A process using primary, cyclic secondary, or bicyclic tertiary amines as reactants, which act as nucleophiles rather than bases, to convert cyclic alkylene ureas into alkylene amines, minimizing degradation and improving yields, and allowing for reactive separation steps like distillation to enhance the reaction.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Productivity
If caustic bases (e.g., sodium hydroxide, KOH) are used to hydrolyze cyclic alkylene ureas, then the carbonyl group is removed to give alkylene amines, but product selectivity decreases due to degradation and salt formation complicating separation
Solution Approach 1:
The invention changes the chemical parameter of the base from inorganic caustic bases (NaOH, KOH) to organic amines with specific structures (primary, cyclic secondary, or bicyclic tertiary amines). This parameter change fundamentally alters the reaction mechanism from base-catalyzed hydrolysis to nucleophilic attack, eliminating salt formation and degradation while maintaining high conversion to desired alkylene amine products
Solution Approach 2:
The invention introduces an organic amine as an intermediary substance that attacks the carbonyl carbon of the cyclic urea. This intermediary approach allows the reaction to proceed through a different mechanism that avoids the harmful side reactions associated with caustic bases, producing only the desired amine product without salts or degradation by-products
2Ease of manufacture
If inorganic bases are used for hydrolysis, then the reaction proceeds, but salts are formed as by-products which complicate separation and reduce yields
Solution Approach 1:
The invention converts the potential harm of base-catalyzed hydrolysis (which causes salt formation and degradation) into a beneficial nucleophilic attack by organic amines. By using organic amines instead of inorganic bases, the reaction achieves high efficiency without the harmful salt by-products, eliminating the need for complex separation steps and maximizing product yield
3Productivity
If caustic bases and high temperatures are used, then the carbonyl group is removed, but corrosion, discolored products and decreased storage stability occur
Solution Approach 1:
The invention changes the chemical nature of the base from inorganic caustic substances to organic amines, which have different chemical properties. This parameter change allows the reaction to proceed at high temperatures with high conversion rates while avoiding the corrosive effects and product degradation associated with caustic bases, thereby maintaining product quality and storage stability
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 approach achieves high yields of alkylene amines with minimized degradation and avoids the formation of undesirable by-products, reducing corrosion risks and improving storage stability, while allowing for efficient separation and recycling of products.
Implementation Method 1
the amine compound is a primary amine, a cyclic secondary amine or a bicyclic tertiary amine... which act as nucleophiles rather than bases, to convert cyclic alkylene ureas into alkylene amines
Data Source
Figure 1
AI summary
The present invention relates to a process to convert cyclic alkylene ureas into their corresponding alkylene amines wherein the process is performed by reaction with an amine compound, and wherein the amine compound comprisesa primaryamine,a cyclic secondary amineor a tertiary bicyclic amine.