Alkyleneamine Manufacturing with Alkyleneurea-Mediated Selectivity
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Solution Overview
Problem
Existing processes for manufacturing higher polyethyleneamines result in a mixture of straight-chain, branched, and piperazine-containing ethyleneamines, with a need for a more efficient process that produces straight-chain compounds in high yield and selectivity, reducing cyclic and branched side products.
Innovation Solution
A process involving the reaction of alkyleneurea compounds with alkylhalide compounds, followed by neutralization with a base, to form alkyleneamine compounds with reduced piperazine and branched products, using alkyleneurea compounds with primary or cyclic secondary amine groups and cyclic alkyleneurea groups, and employing haloalkanes or haloaminoalkanes as alkylhalides.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Manufacturing precision
If the EDC route (reaction of 1,2-dichloroethane with aqueous ammonia and/or ethylene amine) is used to manufacture higher polyethyleneamines, then the manufacturing process is established and commercially viable, but the product mixture contains many types of ethyleneamines including cyclic and branched side products rather than high yield of straight-chain compounds
Solution Approach 1:
The patent introduces a urea additive as an intermediary substance that mediates the reaction between EDC and ethylene amine. The urea forms a complex with EDC, controlling the release and reaction pathway to favor straight-chain product formation while suppressing cyclic and branched side reactions. This intermediary approach resolves the contradiction by enabling selective manufacturing without changing the core EDC route process.
Solution Approach 2:
The patent changes the chemical environment parameters by introducing urea at specific concentrations (0.1-10 wt%) and controlling reaction conditions (temperature, molar ratios). These parameter changes shift the reaction selectivity toward straight-chain ethyleneamines while minimizing side products, thereby improving manufacturing precision without abandoning the established EDC route.
2Productivity
If the EDC route is used to manufacture higher polyethyleneamines, then the process is commercially established, but the yield of desired straight-chain higher alkyleneamine compounds is reduced due to formation of mixed products
Solution Approach 1:
Urea acts as a mediating agent that directs the reaction toward desired straight-chain products. By forming temporary complexes with EDC and controlling the reaction pathway, urea increases the proportion of straight-chain ethyleneamines in the product mixture, thereby improving productivity for the desired compound class while reducing the quantity of unwanted mixture types.
Solution Approach 2:
The urea is introduced before the main reaction occurs, performing a preliminary action of modifying the reaction environment and EDC reactivity. This preliminary modification ensures that when EDC reacts with ethylene amine, the straight-chain pathway is favored from the outset, increasing yield before side reactions can occur.
3Manufacturing precision
If conventional EDC route is used, then the manufacturing process is simple and established, but the selectivity for straight-chain compounds is low due to multiple reaction pathways
Solution Approach 1:
The urea additive serves as a simple chemical intermediary that controls reaction selectivity without requiring complex equipment or process changes. By adding a single chemical substance, the patent achieves high selectivity for straight-chain products while maintaining process simplicity, avoiding the need for complex reaction control systems.
Solution Approach 2:
The patent achieves improved selectivity through simple parameter changes - specifically adding urea at controlled concentrations and adjusting reaction temperature - rather than implementing complex control systems. This approach maintains device simplicity while achieving high manufacturing precision through chemical parameter optimization.
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 enables the selective production of higher alkyleneamine compounds with improved yield and reduced side products, facilitating the conversion to straight-chain ethyleneamines like L-TETA, L-TEPA, and L-PEHA.
Implementation Method 1
reacting an alkyleneurea compound comprising at least one primary amine group, or at least one cyclic secondary amine group, or at least one primary amine group and at least one cyclic secondary amine group, and at least one cyclic alkyleneurea group with an alkylhalide compound to form an alkyleneamine hydrohalide salt
Implementation Method 2
reacting the alkyleneamine hydrohalide salt with a base to form an alkyleneamine compound
Data Source
AI summary
The present disclosure pertains to a process for manufacturing alkyleneamine compounds, comprising the steps ofin a reaction medium reacting an alkyleneurea compound comprising at least one primary amine group, or at least one cyclic secondary amine group, or at least one primary amine group and at least one cyclic secondary amine group, and at least one cyclic alkyleneurea group of formula Iwherein A is selected from the group of C2 to C4 alkylene units, optionally substituted by one or more C1 to C3 alkyl groups, with an alkylhalide compound to form an alkyleneamine hydrohalide salt comprising at least one cyclic alkyleneurea group of formula I, the alkylhalide compound being selected from the group of haloalkanes with 2-6 halogen atoms, and haloaminoalkanes, andreacting the alkyleneamine hydrohalide salt with a base to form an alkyleneamine compound comprising at least one cyclic alkyleneurea group of formula I.