Continuous 1,2-PDA and DMDETA Synthesis via Catalyst Composition

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Solution Overview

Problem

Current processes for preparing 1,2-propylenediamine (1,2-PDA) often result in insufficient formation of dimethyldiethylenetriamine (DMDETA) due to cyclization to dimethylpiperazine, with challenges in achieving high conversion, yield, space-time yield, selectivity, and catalyst stability, and obtaining high purity of both products.

Innovation Solution

A continuous process using monoisopropanolamine (MIPOA) reacting with ammonia in the presence of a supported heterogeneous hydrogenation catalyst, specifically with a catalytically active composition comprising aluminum, copper, nickel, cobalt, and tin, at pressures between 60 to 170 bar, employing tubular or shell and tube reactors, and optimizing conditions for high conversion and selectivity.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Quantity of substance

If conventional catalysts are used for preparing 1,2-PDA, then the reaction proceeds, but DMDETA formation is insufficient due to cyclization to dimethylpiperazine

Engineering Contradiction:
ImproveDMDETA formationVSAvoidcyclization to dimethylpiperazine
Core Design Contradiction:
Quantity of substanceVSObject-generated harmful factors

Solution Approach 1:

The patent changes the chemical composition parameters of the catalyst by incorporating specific metal combinations (Cu, Ni, Co, Zn, Mn, Ga, Ge, In, or Ag with Al2O3 support) and optimizing their weight ratios. This compositional parameter change prevents the undesired cyclization reaction while promoting DMDETA formation, resolving the contradiction between product formation and harmful cyclization.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent uses composite catalyst materials combining multiple metal components (Cu, Ni, Co, Zn, Mn, Ga, Ge, In, or Ag) supported on Al2O3. This composite structure creates synergistic effects that selectively promote the desired amination reaction to form DMDETA while suppressing the cyclization side reaction, thereby increasing DMDETA formation without harmful byproducts.

Inventive Principle:
Principle #40Composite materials

2Productivity

If reaction conditions are optimized for high conversion, then yield and space-time yield improve, but selectivity and catalyst stability become challenging to maintain

Engineering Contradiction:
Improveconversion and yieldVSAvoidselectivity and catalyst stability
Core Design Contradiction:
ProductivityVSReliability

Solution Approach 1:

The patent optimizes multiple reaction parameters simultaneously: pressure (60-170 bar), temperature (120-230°C), and catalyst composition (specific metal weight ratios). This multi-parameter optimization achieves high conversion and yield while maintaining selectivity and catalyst stability, resolving the contradiction between productivity and reliability.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent employs a continuous fixed-bed reaction process where the optimized catalyst operates continuously under controlled conditions. This continuous operation with properly designed catalyst beds maintains steady-state conversion, yield, selectivity, and catalyst stability over extended periods, addressing the contradiction between productivity and reliability.

Inventive Principle:
Principle #20Continuity of useful action

3Manufacturing precision

If high purity of both 1,2-PDA and DMDETA is achieved, then product quality improves, but process complexity increases

Engineering Contradiction:
Improveproduct purityVSAvoidprocess complexity
Core Design Contradiction:
Manufacturing precisionVSDevice complexity

Solution Approach 1:

The patent achieves high product purity by optimizing reaction parameters (pressure, temperature, catalyst composition) to maximize selectivity. This parameter optimization reduces unwanted side reactions and byproduct formation, thereby simplifying downstream purification requirements while maintaining high manufacturing precision.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent employs selective extraction or separation methods to isolate high-purity 1,2-PDA and DMDETA from the reaction mixture. By using the optimized catalyst system that produces minimal byproducts, the separation process becomes less complex, resolving the contradiction between achieving high purity and maintaining process simplicity.

Inventive Principle:
Principle #2Taking out (Extraction)

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 produces 1,2-PDA and DMDETA with high purity and yield, avoiding cyclization to dimethylpiperazine, and allows for the recycling of unconverted MIPOA, thereby improving economic efficiency and mechanical stability of the catalyst.

Implementation Method 1

reaction of monoisopropanolamine (MIPOA) with ammonia in the presence of hydrogen and a supported heterogeneous hydrogenation catalyst (catalyst)

Methodology Applied
Scientific EffectCatalysis: Catalysis

Implementation Method 2

supported heterogeneous hydrogenation catalyst

Methodology Applied
Scientific EffectHydrogenation: Hydrogenation

Data Source

PatentUS11274072B2Process for the continuous preparation of 1,2-propylene diamine (1,2-PDA) and dimethyldiethylene triamine (DMDETA)
Publication Date: 2022.03.15 BASF SE
  • US11274072B2 patent drawing
  • US11274072B2 patent drawing

AI summary

A process for the continuous preparation of 1,2-propylenediamine (1,2-PDA) and dimethyldiethylenetriamine (DMDETA) via reaction of monoisopropanolamine (MIPOA) with ammonia in the presence of hydrogen and a supported heterogeneous hydrogenation catalyst (catalyst), wherein the reaction is effected in the liquid phase at an absolute pressure in the range from 60 to 170 bar.