Ethyleneamine Synthesis via CO2 Adducts
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Solution Overview
Problem
Current methods for manufacturing ethyleneamine compounds, such as reductive amination of monoethanolamine and the ethylene dichloride route, are inefficient in producing high yields of higher ethyleneamines like TETA and TEPA, and are plagued by side reactions, expensive reagents, and environmental concerns.
Innovation Solution
An integrated process involving an adduction step to form CO2 adducts of starting compounds, a reaction step to convert these adducts into polyethyleneamine compounds, and an elimination step to produce the desired ethyleneamines, utilizing CO2 adducts and inorganic bases to achieve selective formation of higher ethyleneamines.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Quantity of substance
If reductive amination of MEA is used to manufacture ethyleneamines, then the process can produce a mixture of ethylene and ethanolamines, but the yield of higher ethyleneamines (TETA and TEPA) is low and the product mixture is complex
Solution Approach 1:
The patent applies preliminary action by first forming CO2 adducts of starting compounds (monoethanolamine, diethanolamine) before the main reaction. This preliminary transformation of reactants into their CO2 adduct forms enables subsequent selective transamination reactions that specifically produce higher ethyleneamines (TETA, TEPA) with improved yield and selectivity, avoiding the complex mixture problem of conventional reductive amination
Solution Approach 2:
The patent changes the chemical state parameters of the reactants by converting them to CO2 adducts. This parameter change transforms the reactivity and selectivity of the transamination reaction, enabling preferential formation of higher ethyleneamines over lower homologues, thus improving both yield and product precision
2Quantity of substance
If the EDC route is used to produce higher polyethylenepolyamines, then the process can achieve production of higher ethyleneamines, but it requires expensive and difficult to handle ethylene dichloride and produces substantial amounts of undesired NaCl
Solution Approach 1:
The patent uses CO2 adducts as intermediary compounds in the transamination reaction. These CO2 adducts serve as activated intermediates that enable the formation of higher ethyleneamines without requiring ethylene dichloride. The intermediary CO2 adduct mechanism eliminates the need for caustic treatment, thereby preventing NaCl formation and associated corrosion problems
Solution Approach 2:
The patent converts the potentially harmful EDC route into a beneficial alternative by using CO2 adducts. Instead of using the problematic EDC reagent that generates NaCl waste, the process utilizes CO2 adducts of ethanolamines as reactants, transforming a harmful chemical pathway into an environmentally friendly one that avoids corrosive waste products
3Quantity of substance
If transamination is used to produce ethyleneamines with two or more ethylene units, then DETA can be produced, but the process is limited mainly to diethylene compound and cannot efficiently produce higher ethyleneamines
Solution Approach 1:
The patent applies universality by using CO2 adducts of multiple starting compounds (monoethanolamine, diethanolamine) that can participate in transamination reactions to produce a universal range of ethyleneamine products. This multi-functional approach enables simultaneous production of DETA, TETA, and TEPA, expanding the product range beyond what conventional transamination can achieve
Solution Approach 2:
The patent segments the synthesis pathway by using different CO2 adducts of ethanolamines as distinct starting materials. By segmenting the reactants into different CO2 adduct forms (from MEA, from DEA), the process can selectively produce different ethyleneamine chain lengths, enabling versatile production of various higher ethyleneamines through controlled transamination
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 effectively and selectively manufactures higher ethyleneamines with improved yields and reduced environmental impact, overcoming the inefficiencies and challenges of existing methods.
Implementation Method 1
an adduction step providing a CO2 adduct of a starting compound comprising a -NH-CH2-CH2-NH-moiety or a -NH-CH2-CH2-OH moiety, or HO-CH2-CH2-OH
Implementation Method 2
an elimination step converting CO2 adduct of polyethyleneamine compound to a corresponding product polyethyleneamine compound
Data Source
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AI summary
The invention relates to a process for manufacturing polyethyleneannine compounds selected from the group of polyethyleneamines and hydroxyethylethyleneamines comprising the steps of - in an adduction step providing a CO2 adduct of a starting compound comprising a - NH-CH2-CH2-NH- moiety or a -NH-CH2-CH2-OH moiety, or HO-CH2-CH2-OH, - in a reaction step reacting a hydroxy-functional compound selected from the group of ethanolamines and dihydroxyethane with an amine-functional compound, wherein at least part of the total of hydroxy-functional compounds and amine-functional compounds is provided in the form of a CO2 adduct, to form CO2 adduct of a product polyethyleneannine compound, - in an elimination step converting CO2 adduct of product polyethyleneannine compound to the corresponding product polyethylene amine compound, wherein a fraction comprising a recycle compound comprising a -NH-CH2-CH2-NH- moiety or a -NH-CH2-CH2-OH moiety, or HO-CH2-CH2-OH, or CO2 adducts thereof, is provided from the end of the reaction step or the elimination step to the adduction step or to the reaction step, the recycle compound having per molecule on average fewer of the total of -NH- CH2-CH2-NH- moieties and -NH-CH2-CH2-OH moieties than the product polyethyleneannine compound.