Dinitrotoluene Hydrogenation Catalyst Deactivation Control

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Solution Overview

Problem

Existing processes for the catalytic hydrogenation of dinitrotoluene (DNT) to toluenediamine (TDA) face challenges with catalyst deactivation and by-product formation, particularly at higher temperatures and lower catalyst levels, leading to reduced selectivity and increased nitroaromatics in the reactor.

Innovation Solution

A continuous process is developed for the liquid phase hydrogenation of DNT using a suspended nickel-containing catalyst, where the DNT concentration in the product discharge is adjusted between 1 to 200 ppm to minimize catalyst deactivation and by-product formation, with regular monitoring and control of DNT and partially hydrogenated intermediate product concentrations to maintain optimal reaction conditions.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Productivity

If the reaction temperature is increased to improve productivity, then the hydrogenation reaction rate increases, but catalyst deactivation accelerates and by-product formation increases

Engineering Contradiction:
Improvehydrogenation reaction rateVSAvoidcatalyst stability
Core Design Contradiction:
ProductivityVSReliability

Solution Approach 1:

The patent applies parameter changes by precisely controlling the DNT concentration parameter within the range of 1-200 ppm in the liquid phase product discharge. This concentration control, combined with maintaining reaction temperatures between 80-150°C and specific residence times, resolves the contradiction by optimizing the reaction conditions to achieve high conversion rates while preventing catalyst deactivation and by-product formation that would occur at higher temperatures

Inventive Principle:
Principle #35Parameter changes

2Loss of substance

If the catalyst concentration is reduced to lower costs, then operating expenses decrease, but by-product formation increases and selectivity decreases

Engineering Contradiction:
Improvecatalyst costVSAvoidconversion selectivity
Core Design Contradiction:
Loss of substanceVSManufacturing precision

Solution Approach 1:

The patent uses parameter changes by optimizing the DNT concentration parameter to 1-200 ppm, which creates optimal reaction conditions that enhance catalyst efficiency. This allows using lower catalyst concentrations while maintaining high selectivity and preventing by-product formation, as the controlled low DNT concentration ensures complete reaction without side reactions

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent implements feedback control through repeated measurement of DNT concentration in the liquid product discharge at time intervals of ≤24 hours. This monitoring system allows real-time adjustment of reaction parameters to maintain optimal conditions, ensuring that even with reduced catalyst levels, the conversion selectivity remains high and by-product formation is prevented

Inventive Principle:
Principle #23Feedback

3Productivity

If the DNT concentration is not controlled to avoid accumulation, then feedstock utilization is maximized, but nitroaromatics levels increase in the reactor

Engineering Contradiction:
Improvefeedstock utilizationVSAvoidnitroaromatics accumulation
Core Design Contradiction:
ProductivityVSObject-generated harmful factors

Solution Approach 1:

The patent applies parameter changes by precisely controlling the DNT concentration parameter within the narrow range of 1-200 ppm in the liquid phase product discharge. This strict concentration control prevents nitroaromatics accumulation while ensuring complete feedstock utilization, as the low but non-zero DNT concentration maintains reaction drive without allowing harmful accumulation

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent implements feedback control through repeated measurement of DNT concentration at intervals of ≤24 hours in the liquid product discharge between the reactor and downstream separation unit. This monitoring and adjustment system ensures that DNT concentration remains within the optimal 1-200 ppm range, preventing nitroaromatics accumulation while maintaining high feedstock utilization

Inventive Principle:
Principle #23Feedback

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 significantly reduces catalyst deactivation and by-product formation, ensuring higher catalyst life and selectivity, and allows for efficient production of TDA with controlled DNT and ANT concentrations, thereby improving the overall efficiency and stability of the hydrogenation reaction.

Implementation Method 1

continuous production of toluenediamine by liquid phase hydrogenation of dinitrotoluene with hydrogen in the presence of a suspended, nickel-containing catalyst

Methodology Applied
Scientific EffectCatalysis: Catalysis

Implementation Method 2

liquid phase hydrogenation of dinitrotoluene with hydrogen

Methodology Applied
Scientific EffectHydrogenation: Hydrogenation

Implementation Method 3

heat exchangers, in particular field tubes, are provided in the reactor interior... in which a heat transfer medium, in particular water, flows and the heat of reaction dissipates

Methodology Applied
Scientific EffectHeat exchange: Heat Exchanger

Implementation Method 4

a propellant steel nozzle at its upper end, via which into the upper area of the Reactor, the reaction mixture withdrawn from the reaction sump is injected

Methodology Applied
Scientific EffectPressure-driven flow: Pressure Gradient

Data Source

PatentEP2571844B1Process for the preparation of tuluenediamine by hydrogenation of dinitrotoluene
Publication Date: 2017.10.04 BASF SE
  • EP2571844B1 patent drawing

AI summary

The invention relates to a process for continuous preparation of tolylenediamine by liquid phase hydrogenation of dinitrotoluene with hydrogen in the presence of a suspended nickel-containing catalyst in a reactor with a product removal unit connected downstream of the reactor to obtain a product output from the reactor comprising a liquid phase containing tolylenediamine and dinitrotoluene in which the nickel-containing catalyst is suspended, wherein the concentration of dinitrotoluene in the liquid phase of the product output from the reactor in the region between the reactor and the downstream product removal unit is adjusted to a value in the range from 1 to 200 ppm by weight, based on the total weight of the liquid phase of the product output from the reactor.