Aromatic Amine Purification via Mixed Liquid Extraction

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Solution Overview

Problem

Existing methods for producing aromatic amine compounds from aromatic nitro compounds using stannous chloride as a catalyst are inefficient in removing the Sn compound residue, leading to impurities and process complications.

Innovation Solution

A method involving the reduction of aromatic nitro compounds with stannous chloride, followed by contact with a potassium hydroxide aqueous solution and a benzene ring compound for liquid separation, effectively removing the Sn compound and obtaining a highly pure aromatic amine compound.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Manufacturing precision

If existing methods (sodium hydrogen carbonate, sodium hydroxide, or potassium hydroxide alone) are used to remove Sn compound residue, then neutralization and extraction can be performed, but the process becomes complex and purification efficiency is insufficient

Engineering Contradiction:
Improvepurity of aromatic amine compoundVSAvoidcomplexity of purification process
Core Design Contradiction:
Manufacturing precisionVSDevice complexity

Solution Approach 1:

The patent combines neutralization and extraction into a single step by using a mixed liquid containing both a compound with a benzene ring (extraction solvent) and a strong base such as potassium hydroxide. This eliminates the need for separate neutralization and extraction steps, simplifying the process while maintaining high purification efficiency.

Inventive Principle:
Principle #5Merging (Combining)

Solution Approach 2:

The mixed liquid serves multiple functions simultaneously: the compound with a benzene ring acts as an extraction solvent to separate the aromatic amine compound, while the strong base neutralizes the Sn compound residue. This multi-functionality reduces the number of reagents and steps required.

Inventive Principle:
Principle #6Universality (Multi-functionality)

2Reliability

If multiple extraction steps with different reagents are performed, then Sn compound removal can be attempted, but processing time and operational complexity increase

Engineering Contradiction:
Improveeffectiveness of Sn compound removalVSAvoidtime for purification process
Core Design Contradiction:
ReliabilityVSLoss of time

Solution Approach 1:

The patent merges neutralization and extraction into one operation by using a mixed liquid containing both extraction solvent and strong base. This single-step approach achieves both Sn compound removal and product extraction simultaneously, reducing processing time while maintaining reliability.

Inventive Principle:
Principle #5Merging (Combining)

Solution Approach 2:

The mixed liquid is prepared in advance with the optimal combination of extraction solvent and strong base, allowing the extraction and neutralization to proceed concurrently without sequential操作步骤, thus saving time.

Inventive Principle:
Principle #10Preliminary action

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 method simplifies the removal of Sn compounds, resulting in a highly pure aromatic amine product with improved process efficiency and purity.

Implementation Method 1

brought into contact with a mixed liquid containing a compound having a benzene ring and a potassium hydroxide aqueous solution to carry out liquid separation

Methodology Applied
Scientific EffectChemical reaction: Chemical Bonding

Implementation Method 2

brought into contact with a mixed liquid containing a compound having a benzene ring and a potassium hydroxide aqueous solution to carry out liquid separation

Methodology Applied
Scientific EffectLiquid-liquid extraction: Liquid-Liquid Extraction

Implementation Method 3

reducing an aromatic nitro compound represented by the formula (1) with stannous chloride

Methodology Applied
Scientific EffectReduction reaction: Reduction

Data Source

PatentEP3246308B1Method for producing aromatic amine compound
Publication Date: 2020.03.11 NISSAN CHEM CORP
  • EP3246308B1 patent drawing
  • EP3246308B1 patent drawing
  • EP3246308B1 patent drawing

AI summary

To provide a novel method for simply and efficiently removing a Sn compound contained in a reaction liquid at the time of reducing an aromatic nitro compound as a starting material with stannous chloride to produce an aromatic amine compound. A method for producing an aromatic amine compound represented by the formula 2, which comprises reducing an aromatic nitro compound represented by the formula 1 (Ar is an aromatic group) with stannous chloride, wherein a reaction liquid obtained by reducing the aromatic nitro compound represented by the formula 1, is brought into contact with a mixed liquid containing a compound having a benzene ring and a potassium hydroxide aqueous solution to carry out liquid separation, and from the obtained organic layer, the aromatic amine compound represented by the formula 2 is obtained: