Hydroformylation Aldehyde Extraction via Biphasic Solvent System

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Solution Overview

Problem

Current methods for separating high-boiling point aldehyde products from hydroformylation processes face challenges such as catalyst damage due to high distillation temperatures and the formation of unwanted acetal compounds, which reduces productivity and complicates separation.

Innovation Solution

A process involving contacting a non-aqueous hydroformylation product solution with an aqueous extraction solvent containing polyalcohols, primary alcohols, and water to form a biphasic mixture, allowing for the separation of high-boiling point aldehydes and catalysts without significant acetal formation, using a temperature range of 25°C to 75°C.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Manufacturing precision

If distillation is used to separate high-boiling point aldehyde products from hydroformylation catalyst, then separation efficiency is improved, but catalyst integrity deteriorates due to high temperature damage

Engineering Contradiction:
Improveseparation efficiencyVSAvoidcatalyst integrity
Core Design Contradiction:
Manufacturing precisionVSReliability

Solution Approach 1:

The invention changes the separation method from thermal distillation to liquid-liquid extraction, fundamentally altering the operating parameters from high temperature to ambient or moderate temperature conditions. This parameter change allows effective separation while preserving catalyst integrity, directly resolving the contradiction between separation efficiency and catalyst integrity

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention introduces an extraction solvent as an intermediary substance to facilitate separation. The extraction solvent selectively dissolves the aldehyde product from the catalyst-containing solution, enabling separation without direct thermal contact. This intermediary approach achieves both efficient separation and catalyst protection simultaneously

Inventive Principle:
Principle #24Intermediary (Mediator)

2Manufacturing precision

If polyhydric alcohol is used as extraction solvent for high-boiling point aldehydes, then extraction efficiency is improved, but acetal formation increases reducing productivity

Engineering Contradiction:
Improveextraction efficiencyVSAvoidreaction rate
Core Design Contradiction:
Manufacturing precisionVSProductivity

Solution Approach 1:

The invention uses a composite extraction solvent system combining polyhydric alcohol with other components (such as tertiary amines or specific additives) to achieve both high extraction efficiency and suppression of acetal formation. The composite solvent system leverages the synergistic effects of its components to resolve the contradiction between extraction efficiency and productivity

Inventive Principle:
Principle #40Composite materials

Solution Approach 2:

The invention modifies the local chemical environment by adding specific additives or modifying the solvent composition to create conditions favorable for extraction while unfavorable for acetal formation. This local quality adjustment allows the extraction process to proceed efficiently without the harmful side reaction

Inventive Principle:
Principle #3Local quality

3Productivity

If tertiary amines are added to reduce acetal formation, then productivity is improved, but process complexity increases

Engineering Contradiction:
Improvereaction rateVSAvoidprocess complexity
Core Design Contradiction:
ProductivityVSDevice complexity

Solution Approach 1:

The invention employs readily available, inexpensive tertiary amines or alternative additives that can be easily introduced and removed from the process. These substances provide the necessary functionality to suppress acetal formation without requiring complex equipment or elaborate process control systems, thus improving productivity while minimizing added complexity

Inventive Principle:
Principle #27Cheap short-living objects (Disposable)

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 effectively recovers high-boiling point aldehydes with minimal catalyst loss and acetal formation, improving productivity by maintaining catalyst integrity and simplifying the separation process.

Implementation Method 1

contacting the non-aqueous hydroformylation product solution with an aqueous extraction solvent to form a biphasic mixture

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

Data Source

PatentEP3696160B1Extraction process for high-boiling aldehyde product separation and catalyst recovery
Publication Date: 2023.05.10 DALIAN CHEM IND CO LTD
  • EP3696160B1 patent drawing
  • EP3696160B1 patent drawing
  • EP3696160B1 patent drawing

AI summary

The invention relates to an extraction process for the recovery of high-boiling aldehyde products and catalysts from a hydroformylation product solution.