TBADG Synthesis via Copper-Alumina Catalyst
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Solution Overview
Problem
The reaction of diethylene glycol (DG) with tert-butylamine (TBA) over nickel catalysts poses safety risks due to the formation of toxic decomposition products, such as methoxyethanol, which complicates product quality and specification, and existing processes suffer from low selectivity and yield issues.
Innovation Solution
A process involving the reaction of DG with TBA in the presence of a copper- and aluminum oxide-containing catalyst, operated in the gas phase or gas/liquid mixed phase, with a specific catalyst composition and conditions to achieve high yields and selectivities, suppressing decarbonylation and ensuring a safe process regime.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Productivity
If nickel catalysts are used for the reaction of DG with TBA, then the reaction can proceed, but toxic decomposition products such as methoxyethanol are formed causing safety risks and product quality issues
Solution Approach 1:
The patent changes the catalyst composition parameter from nickel-based to copper-based catalyst with specific CuO content (20-75 wt%) and Al2O3 content (20-75 wt%), which fundamentally alters the reaction pathway to eliminate toxic decomposition products while maintaining productivity
Solution Approach 2:
The patent converts the harmful effect of decarbonylation reactions that occur with nickel catalysts into a beneficial selective amination reaction using copper catalyst, where the copper surface promotes the desired reaction between DG and TBA while suppressing decomposition pathways
2Manufacturing precision
If existing copper catalysts are used, then some selectivity can be achieved, but yields and selectivities remain low
Solution Approach 1:
The patent creates a composite catalyst system combining copper oxide and aluminum oxide in specific proportions (20-75 wt% CuO, 20-75 wt% Al2O3), where the synergistic interaction between the two components enhances both selectivity to TBADG and overall reaction yield compared to simple copper catalysts
Solution Approach 2:
The patent optimizes the local composition of the catalyst by controlling the specific content ranges of CuO and Al2O3, creating active sites with appropriate electronic and geometric properties that favor the desired amination reaction while suppressing side reactions
3Ease of operation
If the reaction is performed in liquid phase, then mass transfer is easier, but safety risks increase due to formation of decomposition products
Solution Approach 1:
The patent changes the phase parameter from liquid phase to gas phase reaction, which fundamentally alters the reaction environment to eliminate the formation of toxic decomposition products while maintaining operational ease through optimized gas flow and contact conditions
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 improved yields and selectivities for 2-(2-tert-butylaminoethoxy)ethanol (TBADG) with reduced formation of undesired products, enhancing safety and product quality by optimizing the reaction conditions and catalyst composition.
Implementation Method 1
A process for preparing 2-(2-tert-butylaminoethoxy)ethanol (tert-butylaminodiglycol, TBADG) by reacting diethylene glycol (DG) with tert-butylamine (TBA) in the presence of hydrogen and of a copper catalyst
Implementation Method 2
the reaction of DG with TBA over nickel catalysts poses safety risks... A process involving the reaction of DG with TBA in the presence of a copper- and aluminum oxide-containing catalyst
Data Source
AI summary
A process for preparing 2-(2-tert-butylaminoethoxy)ethanol (tert-butylaminodiglycol, TBADG) by reacting diethylene glycol (DG) with tert-butylamine (TBA) in the presence of hydrogen and of a copper catalyst, by effecting the reaction at a temperature in the range from 160 to 220° C. in the presence of a copper- and aluminum oxide-containing catalyst, where the catalytically active material of the catalyst, before the reduction thereof with hydrogen, comprises20 to 75% by weight of aluminum oxide (Al2O3),20 to 75% by weight of oxygen compounds of copper, calculated as CuO, and≦5% by weight of oxygen compounds of nickel, calculated as NiO.