Organic Amine Isolation via Ammonia-Induced Phase Separation

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Solution Overview

Problem

Existing processes for isolating organic amines from compositions with acids or their salts result in significant material loss, byproduct formation, and difficulty in removing impurities, leading to polyamides with inferior properties or incomplete polymerization.

Innovation Solution

A process involving the addition of ammonia or hydrazine to form a multi-phase system, allowing for the separation and isolation of the organic amine-rich phase, which is lean in acid content, and the acid-rich phase, facilitating easy separation and recovery of by-products.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Manufacturing precision

If alkali is added to raise pH to 12-14 for amine extraction, then the organic amine can be extracted with polar solvents, but aqueous byproducts comprising dissolved alkali acid salts are formed causing significant material loss

Engineering Contradiction:
Improveamine extraction efficiencyVSAvoidmaterial loss in aqueous byproducts
Core Design Contradiction:
Manufacturing precisionVSLoss of substance

Solution Approach 1:

The invention changes the pH adjustment method from adding alkali to adding organic acid. This parameter change transforms the byproduct from water-soluble alkali acid salts to organic-soluble ammonium/organic acid salts, which can be extracted into the organic phase, thereby reducing material loss in aqueous waste streams

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention introduces an organic acid as an intermediary substance that mediates between the amine and the pH adjustment requirement. The organic acid reacts with the amine to form ammonium/organic acid salt complexes that are soluble in organic solvents, enabling phase separation without creating water-soluble byproducts

Inventive Principle:
Principle #24Intermediary (Mediator)

2Loss of substance

If organic solvent is added without alkali to isolate amine as salt, then material loss is reduced, but amine impurities easily incorporate into the cadaverine acid salt making purification difficult

Engineering Contradiction:
Improvematerial lossVSAvoidamine purity
Core Design Contradiction:
Loss of substanceVSManufacturing precision

Solution Approach 1:

The invention applies local quality by using a polar solvent with specific properties (high dielectric constant, hydrogen bonding capability) that creates a selective environment. This local solvent environment preferentially dissolves the desired amine while leaving impurities in the aqueous phase, achieving both recovery and purification simultaneously

Inventive Principle:
Principle #3Local quality

3Manufacturing precision

If multiple steps are used for amine isolation (alkali addition, extraction, byproduct separation), then separation can be achieved, but process complexity increases and productivity decreases

Engineering Contradiction:
Improveseparation completenessVSAvoidprocess efficiency
Core Design Contradiction:
Manufacturing precisionVSProductivity

Solution Approach 1:

The invention merges multiple separation steps into a single operation. By adding organic acid directly to the reaction mixture and then extracting with organic solvent, the pH adjustment, amine complexation, and phase separation occur in an integrated process, eliminating intermediate steps and improving productivity

Inventive Principle:
Principle #5Merging (Combining)

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 efficient separation of organic amines in a single step, reduces material loss, and allows for the easy removal of amine impurities and recovery of surplus ammonia or hydrazine, enhancing the quality of polyamide production.

Implementation Method 1

the addition of ammonia or hydrazine in a sufficient amount to a composition comprising the organic amine and the acid, or a salt of the organic amine and the acid, results in formation of a multi-phase system comprising an organic amine-rich phase and an acid-rich phase

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

Data Source

PatentEP1971569B1Process for isolation of an organic amine
Publication Date: 2012.02.08 DSM IP ASSETS BV
  • EP1971569B1 patent drawingFigure 1
  • EP1971569B1 patent drawingFigure 2
  • EP1971569B1 patent drawingFigure 3

AI summary

The invention relates to a process for the isolation of an organic amine from a composition comprising the organic amine and an acid, or a salt of the organic amine and the acid, wherein the process comprises steps wherein ammonia or hydrazine is added to the composition thereby forming a multi-phase system comprising an organic amine -rich phase and an acid-rich phase, the organic amine-rich phase and the acid-rich phase obtained in step (i) are separated, and the organic amine is isolated from the organic amine -rich phase.