Hydroformylation Aldehyde Purification via Partial Condensation

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Solution Overview

Problem

Current hydroformylation processes face challenges in removing organophosphorous ligands from aldehyde product streams, leading to contamination and premature catalyst deactivation, with existing methods being costly and complex, and failing to effectively control phosphorous ligand levels and heavies formation.

Innovation Solution

A process involving partial condensation of the vaporized aldehyde product stream using a heat exchange device to separate and remove phosphorous ligands and by-products, followed by processing in a refining column to recover aldehydes, thereby reducing ligand contamination and heavies buildup.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Productivity

If a vaporizer with elevated temperatures and reduced pressure is used to separate product from catalyst solution, then separation efficiency is improved, but organophosphorous ligand contamination in the product stream increases

Engineering Contradiction:
Improveseparation efficiencyVSAvoidligand contamination
Core Design Contradiction:
ProductivityVSObject-affected harmful factors

Solution Approach 1:

The separation process is divided into multiple stages: initial vaporization at elevated temperature for catalyst removal, followed by a condensation stage where the vapor stream is cooled to condense and remove ligand contaminants before the final product is collected. This segmentation allows each stage to optimize for its specific function.

Inventive Principle:
Principle #1Segmentation

Solution Approach 2:

The process dynamically changes temperature parameters during separation. The vaporizer operates at elevated temperatures (>100°C) for efficient catalyst removal, then the stream undergoes cooling in a condensation stage to remove ligands. This parameter change allows the system to achieve both high separation efficiency and low contamination.

Inventive Principle:
Principle #35Parameter changes

2Manufacturing precision

If sophisticated distillation systems are used to remove ligand contamination, then product purity is improved, but system complexity and capital costs increase

Engineering Contradiction:
Improveproduct purityVSAvoidsystem complexity
Core Design Contradiction:
Manufacturing precisionVSDevice complexity

Solution Approach 1:

The harmful ligand components are extracted from the vapor stream through condensation in a separate condensation zone. By removing the contaminants in this intermediate stage rather than requiring complete redistillation, the system achieves high purity with simpler equipment.

Inventive Principle:
Principle #2Taking out (Extraction)

Solution Approach 2:

Instead of applying full distillation to the entire product stream, the process applies partial condensation to a portion of the vapor stream to remove ligands. This partial action is sufficient to achieve the required purity level without the complexity of sophisticated distillation systems.

Inventive Principle:
Principle #16Partial or excessive action

3Object-generated harmful factors

If reflux condenser and packing are used in the vaporizer, then heavies removal is improved, but pressure drop and heavies formation increase

Engineering Contradiction:
Improveheavies removalVSAvoidpressure drop
Core Design Contradiction:
Object-generated harmful factorsVSStress or pressure

Solution Approach 1:

The separation of heavies is segmented into two approaches: initial removal through the vaporizer design, and secondary removal through a separate condensation stage. This segmentation allows heavies to be removed without requiring excessive reflux and packing that would cause high pressure drops.

Inventive Principle:
Principle #1Segmentation

Solution Approach 2:

The process replaces the mechanical complexity of reflux condensers and packing with a thermal approach using condensation at controlled temperatures. This substitution achieves heavies removal with lower pressure drops by relying on temperature-based phase change rather than mechanical separation elements.

Inventive Principle:
Principle #28Mechanics substitution (Replace mechanical system)

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 approach simplifies the removal of organophosphorous ligands and aldehyde heavies, reducing contamination and catalyst deactivation, while minimizing capital and operational costs by processing only a portion of the product stream, thus maintaining catalyst stability and efficiency.

Implementation Method 1

contacting the vaporized aldehyde product stream with a partial condenser so as to condense the phosphorous ligand and the by-products

Methodology Applied
Scientific EffectCondensation: Condensation

Implementation Method 2

the partial condenser comprises a heat exchange device

Methodology Applied
Scientific EffectHeat exchange: Heat Exchanger

Data Source

PatentEP3374340B1Process for producing aldehydes
Publication Date: 2021.12.29 DOW TECHNOLOGY INVESTMENTS LLC
  • EP3374340B1 patent drawingFigure 1
  • EP3374340B1 patent drawing
  • EP3374340B1 patent drawing

AI summary

The present invention relates generally to processes for producing aldehydes wherein an olefinic compound, carbon monoxide, and hydrogen are reacted in the presence of a solubilized rhodium-phosphorous complex. In one embodiment, the process comprises (a) receiving a vaporized aldehyde product stream downstream from a hydroformylation reactor, the vaporized aldehyde product stream comprising aldehydes, phosphorous ligand, and aldehyde condensation by-products; (b) contacting the vaporized aldehyde product stream with a partial condenser so as to condense the phosphorous ligand and the by- products, wherein up to 10 weight percent of the vaporized stream is condensed; (c) removing the condensed phosphorous ligand and the condensed by-products from the liquid condensation stream using a refining column; and (d) further processing the vaporized aldehydes from the separate refining column.