Nanofiltration for Hydroformylation Catalyst Separation

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Solution Overview

Problem

Industrial hydroformylation of isobutene produces a product mixture with high levels of secondary products known as high boilers, which reduce the yield of the primary product 3-methylbutanal and impair process economics.

Innovation Solution

A process involving hydroformylation of an isobutene-containing hydrocarbon stream followed by nanofiltration to separate 3-methylbutanoic acid from the transition metal complex catalyst, using nanofiltration membranes with low retention for 3-methylbutanoic acid, and subsequent thermal separation to enrich 3-methylbutanal, thereby reducing the formation of high boilers.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If traditional distillation is used to separate catalyst from hydroformylation mixture, then catalyst separation is achieved, but energy consumption increases and catalyst deactivation risk increases

Engineering Contradiction:
Improvecatalyst activity maintenanceVSAvoidenergy consumption
Core Design Contradiction:
ReliabilityVSUse of energy by moving object

Solution Approach 1:

The patent replaces the thermal distillation process with a membrane-based separation system. The nanofiltration membrane selectively retains the catalyst while allowing aldehydes and other products to pass through, eliminating the need for high-energy distillation and associated catalyst exposure to thermal deactivation conditions

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

Solution Approach 2:

The patent introduces a membrane as an intermediary separation medium between the catalyst and products. This membrane acts as a selective barrier that facilitates catalyst retention without requiring the catalyst to undergo phase changes or exposure to harsh thermal conditions

Inventive Principle:
Principle #24Intermediary (Mediator)

2Productivity

If hydroformylation proceeds to high conversion, then productivity increases, but high boiler formation increases and reduces primary product yield

Engineering Contradiction:
Improvehydroformylation conversionVSAvoidprimary product purity
Core Design Contradiction:
ProductivityVSManufacturing precision

Solution Approach 1:

The patent implements preliminary separation of the catalyst from the reaction mixture using nanofiltration before final product isolation. This early catalyst removal prevents catalyst-mediated side reactions that form high boilers, allowing high conversion to proceed while maintaining primary product purity

Inventive Principle:
Principle #10Preliminary action

Solution Approach 2:

The patent extracts the catalyst from the reaction mixture using a nanofiltration membrane that selectively retains the catalyst while allowing aldehydes and other products to pass through. This extraction prevents further catalyst-mediated side reactions and high boiler formation

Inventive Principle:
Principle #2Taking out (Extraction)

3Reliability

If nanofiltration membrane with high catalyst retention is used, then catalyst recovery improves, but 3-methylbutanoic acid retention increases leading to more high boilers

Engineering Contradiction:
Improvecatalyst recoveryVSAvoid3-methylbutanoic acid removal
Core Design Contradiction:
ReliabilityVSLoss of substance

Solution Approach 1:

The patent applies the principle of local quality by selecting a membrane with specific retention characteristics that create different separation behaviors for different components. The membrane is chosen to have high retention for the catalyst while maintaining low retention for 3-methylbutanoic acid, achieving selective separation based on local molecular properties

Inventive Principle:
Principle #3Local quality

Solution Approach 2:

The patent optimizes the separation process by carefully selecting membrane parameters (molecular weight cutoff, pore size, charge) to achieve the desired selectivity. By changing the membrane parameters, the process achieves high catalyst retention while allowing 3-methylbutanoic acid to pass through

Inventive Principle:
Principle #35Parameter changes

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 significantly reduces the proportion of high boilers in the product mixture, increasing the yield of 3-methylbutanal and allowing for the recovery and reuse of the transition metal complex catalyst, thereby improving process efficiency and raw material utilization.

Implementation Method 1

separating the product mixture by means of a nanofiltration device comprising one or more membrane separation stages

Methodology Applied
Scientific EffectNanofiltration: Semipermeable Membrane

Implementation Method 2

nanofiltration membranes with low retention for 3-methylbutanoic acid

Methodology Applied
Scientific EffectPermeation: Permeation

Implementation Method 3

subsequent thermal separation to enrich 3-methylbutanal

Methodology Applied
Scientific EffectDistillation: Distillation

Implementation Method 4

hydroformylation of an isobutene-containing hydrocarbon stream in the presence of a transition metal complex catalyst

Methodology Applied
Scientific EffectCatalysis: Catalysis

Data Source

PatentEP2817284B1Method and device for the hydroformylation of isobutene and for the separation of the product mixture
Publication Date: 2017.10.25 EVONIK OPERATIONS GMBH
  • EP2817284B1 patent drawing
  • EP2817284B1 patent drawing
  • EP2817284B1 patent drawing

AI summary

The invention relates to a method for producing a product mixture (2) by means of the technical hydroformylation of a hydrocarbon stream (1) that contains isobutene, and for separating the product mixture (2) that is obtained, as well as to a device for the claimed method and to the use of a claimed device. The problem addressed thereby is that of providing a method and an associated device that allow the amount of high-boiling substances in the product mixture (2) to be kept as low as possible and thus the yield of the reaction to be increased. The problem is solved by the use of a nano-filtration device (M) for separating the catalyst from the product mixture (2), said device having especially high permeability to 3-methylbutanoic acid.