Higher Ethylene Amine Synthesis via Carbon Oxide Delivery
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Solution Overview
Problem
Current methods for producing higher ethylene amines, such as the EDC route, suffer from low selectivity and yield, generating toxic byproducts and requiring complex purification due to their dependence on ethylene dichloride, which is hazardous and expensive, and result in mixtures of polyethylene amines rather than specific products.
Innovation Solution
A process involving the reaction of an ethanolamine-functional compound with an amine-functional compound in the presence of a carbon oxide delivering agent, such as carbon dioxide or organic ureas, at elevated temperatures, optimizing the molar ratio of the carbon oxide delivering agent to enhance yield and selectivity of higher ethylene amines like TETA and TEPA, while minimizing side products and waste salt generation.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Productivity
If the EDC route is used to produce higher ethylene amines, then production capacity is achieved, but selectivity is low and toxic byproducts are generated
Solution Approach 1:
The invention extracts and eliminates the toxic ethylene dichloride intermediate from the process by using a direct amination approach where ammonia reacts with ethylene oxide to form ethylene amines without generating halogenated byproducts
Solution Approach 2:
The invention converts the harmful EDC route into a beneficial direct amination process that uses ammonia and ethylene oxide as clean reactants, transforming a toxic process into an environmentally friendly one while maintaining productivity
2Productivity
If the EDC route is used to produce higher ethylene amines, then production is achieved, but complex purification is required due to waste salt
Solution Approach 1:
The invention extracts and eliminates the waste salt formation issue by replacing the EDC hydrolysis step with a direct amination process that produces only water as a byproduct, thereby removing the need for complex salt removal and purification equipment
Solution Approach 2:
The invention converts the harmful waste salt generation into a beneficial water-only byproduct process, simplifying the purification train and reducing equipment complexity while maintaining production capacity
3Quantity of substance
If transamination is used to produce ethylene amines with two or more ethylene units, then some higher amines are formed, but yields are low and limited to DETA
Solution Approach 1:
The invention changes the reaction parameters by using a catalyst system and controlled temperature profile that enables high-yield formation of TETA and other higher ethylene amines, overcoming the yield limitations of conventional transamination methods
Solution Approach 2:
The invention introduces a catalyst as an intermediary that facilitates the amination reaction, enabling efficient production of higher ethylene amines with yields that overcome the limitations of uncatalyzed transamination processes
4Quantity of substance
If reductive amination of MEA is used, then EDA and DETA are produced, but side reactions produce complex mixtures with low selectivity
Solution Approach 1:
The invention applies local quality control through catalyst selection and reaction condition optimization that directs the reaction toward specific higher ethylene amine products, achieving high selectivity for TETA and other target amines while minimizing unwanted side products
Solution Approach 2:
The invention changes the reaction parameters including temperature, pressure, and catalyst composition to achieve high selectivity for desired higher ethylene amines, transforming a non-selective process into a precision synthesis method
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 significantly increases the yield of higher ethylene amines and improves selectivity, reducing the formation of side products and waste salt, thus providing a more efficient and environmentally friendly method for producing specific higher ethylene amines like TETA and TEPA.
Implementation Method 1
reacting an ethanolamine functional compound with an amine functional compound in the presence of a carbon oxide delivering agent
Data Source
AI summary
The present invention relates to a process to prepare ethylene amines of the formula NH2-(C2H4-NH-)pH wherein p is at least 3 or derivatives thereof wherein one or more units -NH-C2H4-NH- may be present as a cyclic ethylene urea unit or between two units -NH-C2H4-NH- a carbonyl moiety is present, by reacting an ethanolamine-functional compound, an amine-functional compound in the presence of a carbon oxide delivering agent, wherein the molar ratio of carbon oxide delivering agent to amine-functional compound is at least 0.6 to 1.