Hydrogenating TDA Tar with Heterogeneous Catalysts

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Solution Overview

Problem

The disposal of toluenediamine (TDA) tar, a high-boiler fraction from dinitrotoluene hydrogenation, is costly and environmentally unfriendly, as it contains significant amounts of TDA that are wasted through incineration, and there is a need for an alternative use to reduce the amount of non-useable TDA tar.

Innovation Solution

A process involving the hydrogenation of TDA tar using a heterogeneous catalyst comprising metals like Ni, Co, Ru, Pd, or Pt on supports such as carbon or ZrO2, which converts TDA tar into valuable products like methylcyclohexylamines or mid-boiler fractions, allowing for the recovery of TDA without affecting the flow behavior or viscosity of the tar.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Ease of manufacture

If TDA tar is disposed of through incineration, then the disposal process is simple, but significant amounts of TDA are wasted and environmental damage occurs

Engineering Contradiction:
Improvedisposal process simplicityVSAvoidTDA waste
Core Design Contradiction:
Ease of manufactureVSLoss of substance

Solution Approach 1:

The patent applies parameter changes by altering the chemical state of TDA tar through hydrogenation reaction. The tar is converted from a high-boiler fraction suitable only for incineration into valuable chemical products (methylcyclohexylamines, mid-boiler fractions) by changing its molecular structure through catalytic hydrogenation, thereby eliminating waste and creating useful products

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent converts the harmful waste stream (TDA tar requiring incineration) into a beneficial resource. By hydrogenating the tar, the process transforms what was previously environmental pollution into valuable chemical products, turning a disposal problem into a production opportunity that generates revenue and reduces environmental impact

Inventive Principle:
Principle #22Blessing in disguise (Convert harm into benefit)

2Loss of substance

If TDA tar is hydrogenated to produce valuable products, then TDA recovery and cost savings are achieved, but the process requires complex heterogeneous catalyst systems

Engineering Contradiction:
ImproveTDA recoveryVSAvoidcatalyst system complexity
Core Design Contradiction:
Loss of substanceVSDevice complexity

Solution Approach 1:

The patent employs parameter changes by systematically varying catalyst composition (different metals like Ni, Co, Ru, Pd, Pt on various supports), temperature, pressure, and hydrogenation conditions to optimize the conversion of TDA tar. These parameter adjustments enable selective production of desired products while managing the complexity of the catalytic system

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent utilizes composite catalyst systems combining different metals (e.g., Ni-Co, Ru-Pt) on various supports (carbon, ZrO2, TiO2). These composite materials provide synergistic effects that enhance catalytic activity and selectivity, allowing efficient TDA recovery while managing process complexity through material science advancements

Inventive Principle:
Principle #40Composite materials

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 a yield of up to 47% of valuable products, such as methylcyclohexylamines, from TDA tar, reducing the need for incineration and enabling the reuse of TDA, while also isolating catalyst residues, thus saving costs and minimizing environmental impact.

Implementation Method 1

a process for hydrogenating toluenediamine (TDA) tar containing TDA and high boilers relative to TDA

Methodology Applied
Scientific EffectHydrogenation: Hydrogenation

Implementation Method 2

contacting the toluenediamine tar with a heterogeneous hydrogenation catalyst comprising at least one metal selected from the group consisting of Ni, Co, Ru, Pd, Pt on at least one catalyst support selected from the group consisting of carbon, TiO2 and ZrO2

Methodology Applied
Scientific EffectCatalysis: Catalysis

Data Source

PatentEP3523272B1Process for hydrogenating toluenediamine (TDA) tar
Publication Date: 2020.09.23 BASF SE

AI summary

Process for hydrogenating toluenediamine (TDA) tar containing TDA and high boilers relative to TDA, including the step of contacting the toluenediamine tar with a heterogeneous hydrogenation catalyst comprising at least one metal selected from the group consisting of Ni, Co, Ru, Pd, Pt on at least one catalyst support selected from the group consisting of carbon, TiO2 and ZrO2, and with hydrogen under hydrogenating conditions.