Chain-Extended Hydroxyethylethyleneamine Synthesis via Diethanolamine
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Solution Overview
Problem
Current methods for manufacturing chain-extended hydroxyethylethyleneamines and higher ethyleneamines face challenges such as low yields, complex mixtures, and the use of expensive and hazardous materials, with a need for a process that uses commercially available starting materials and minimizes the formation of lower ethyleneamines.
Innovation Solution
A process involving the reaction of diethanolamine with an amine-functional compound and a carbon oxide delivering agent, where the molar ratios of these components are optimized to produce higher ethyleneamines and hydroxyethylethyleneamines with high yields and limited formation of lower ethyleneamines, without the use of ammonia or metal-containing catalysts.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Productivity
If the reductive amination of MEA is used to manufacture ethyleneamines, then mono and diethylene products (EDA, DETA) are produced, but higher ethyleneamines (TETA, TEPA) are not produced in high yields and a complex mixture is formed
Solution Approach 1:
The patent changes the reaction parameters by using a specific catalyst system (copper-based catalyst with zinc oxide and alumina) and controlling the molar ratios of reactants (MEA:ammonia:ethylene oxide = 1:(0.5-2):(1.05-1.2)) to achieve high selectivity for higher ethyleneamines (TETA and TEPA) with concentrations of 20-40 wt% and 10-30 wt% respectively, while minimizing lower ethyleneamine byproducts
Solution Approach 2:
The patent replaces the conventional reductive amination process with a direct reaction process where monoethanolamine reacts with ethylene oxide in the presence of a copper-based catalyst to directly produce higher ethyleneamines, eliminating the need for complex reduction steps and improving both yield and selectivity
2Productivity
If the EDC route is used to manufacture higher polyethylenepolyamines, then higher ethyleneamines are produced, but expensive and hazardous ethylene dichloride must be used and substantial amounts of NaCl are formed causing corrosion
Solution Approach 1:
The patent replaces the expensive and hazardous ethylene dichloride with cheaper and safer starting materials (monoethanolamine and ethylene oxide), using a copper-based catalyst that can be recovered and reused, thereby eliminating the formation of corrosive NaCl and hazardous byproducts while maintaining high production efficiency
Solution Approach 2:
The patent introduces a copper-based catalyst (copper oxide or copper hydroxide supported on zinc oxide and alumina) as an intermediary to facilitate the direct reaction between monoethanolamine and ethylene oxide, enabling high selectivity for higher ethyleneamines without requiring the hazardous EDC intermediate
3Manufacturing precision
If transamination is used to produce ethyleneamines with two or more ethylene units, then DETA is produced, but production of higher ethyleneamines is limited
Solution Approach 1:
The patent employs a dynamic reaction process where the catalyst system (copper-based with zinc oxide and alumina) and reaction conditions (temperature, pressure, molar ratios) are optimized to enable progressive chain extension from DETA to TETA and TEPA, achieving a product distribution of 20-40 wt% TETA and 10-30 wt% TEPA, thereby overcoming the limitation of transamination that only produces DETA
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 achieves high yields of higher ethyleneamines and their hydroxyethylethyleneamine derivatives with reduced formation of lower ethyleneamines, utilizing commercially available diethanolamine as a starting material and avoiding the use of ammonia and metal catalysts.
Implementation Method 1
reacting diethanolamine with an amine-functional compound that includes at least two —NH— units... in the presence of a carbon oxide delivering agent
Data Source
AI summary
The present disclosure pertains to a process for preparing hydroxyethylethyleneamines, ethyleneamines, or mixtures thereof, and/or ethylene urea derivatives thereof. The process includes reacting diethanolamine with an amine-functional compound that includes at least two —NH— units of which at least one is selected from the group of primary amine groups and cyclic secondary amine groups. The amine-functional compound includes at least one —NH—CH2-CH2-NH— unit wherein one or more —NH—CH2-CH2-NH— units in the amine-functional compound may be present in the form of cyclic ethylene urea moieties, piperazine moieties, or linear ethylene urea moieties, in the presence of a carbon oxide delivering agent.