C8 Hydrocarbon Composition Isoindex Control for Hydroformylation

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Solution Overview

Problem

The production of C8 olefins through oligomerization often results in a composition with high branching, leading to inefficiencies in hydroformylation processes, particularly in cobalt-based systems, where internal double bonds reduce conversion rates and quality of plasticizer alcohols, and in rhodium-based systems, where high branching results in undesirable viscosity increases.

Innovation Solution

A C8 hydrocarbon composition with a specific isomer distribution, optimized for both cobalt and rhodium hydroformylation processes, is achieved by oligomerizing a butene-containing C4 hydrocarbon stream using a heterogeneous nickel-containing catalyst at high temperatures and short residence times, resulting in a composition with a targeted isoindex and double bond isomer distribution that maximizes conversion while minimizing branched aldehydes.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Quantity of substance

If oligomerization is carried out to produce C8 olefins, then C8 olefins are formed as primary products, but the composition exhibits high branching leading to reduced hydroformylation conversion rates and quality issues

Engineering Contradiction:
ImproveC8 olefin productionVSAvoidhydroformylation conversion rate
Core Design Contradiction:
Quantity of substanceVSReliability

Solution Approach 1:

The patent applies parameter changes by optimizing the isoindex (a measure of branching) to a specific range of 0.85-1.15 and controlling the double bond isomer distribution with specific ratios of terminal to internal double bonds. These parameter optimizations resolve the contradiction by producing C8 olefins with controlled branching that maintain high hydroformylation conversion rates while ensuring adequate C8 olefin production.

Inventive Principle:
Principle #35Parameter changes

2Quantity of substance

If oligomerization produces highly branched C8 olefins, then C8 olefins are obtained in sufficient quantity, but internal double bonds reduce conversion rates in cobalt-based hydroformylation

Engineering Contradiction:
ImproveC8 olefin yieldVSAvoidhydroformylation conversion rate
Core Design Contradiction:
Quantity of substanceVSProductivity

Solution Approach 1:

The patent changes the structural parameters of C8 olefins by controlling the isoindex to 0.85-1.15 and optimizing the double bond isomer distribution. This ensures sufficient C8 olefin yield while maintaining high conversion rates in cobalt-based hydroformylation by limiting excessive branching and internal double bond formation.

Inventive Principle:
Principle #35Parameter changes

3Productivity

If high branching C8 olefins are produced, then oligomerization efficiency is maintained, but rhodium-based hydroformylation experiences undesirable viscosity increases

Engineering Contradiction:
Improveoligomerization efficiencyVSAvoidproduct viscosity
Core Design Contradiction:
ProductivityVSShape

Solution Approach 1:

The patent optimizes the structural parameters of C8 olefins by controlling the isoindex to 0.85-1.15 and managing the double bond isomer distribution. This maintains oligomerization efficiency while producing C8 olefins with controlled branching that prevent excessive viscosity increases during subsequent rhodium-based hydroformylation and plasticizer production.

Inventive Principle:
Principle #35Parameter changes

4Productivity

If the isoindex is reduced to minimize branching, then hydroformylation efficiency improves, but the degree of branching control becomes more difficult

Engineering Contradiction:
Improvehydroformylation efficiencyVSAvoidisoindex control
Core Design Contradiction:
ProductivityVSEase of manufacture

Solution Approach 1:

The patent establishes a balanced parameter range for isoindex (0.85-1.15) that optimizes hydroformylation efficiency while remaining practically achievable through standard oligomerization processes. This balanced approach avoids excessive complexity in manufacturing control while ensuring high conversion rates and quality plasticizer production.

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

The optimized C8 hydrocarbon composition ensures high conversion rates in hydroformylation, reducing sales losses and quality issues by maintaining a balanced degree of branching and double bond isomer distribution, thus producing high-quality plasticizer alcohols with improved efficiency.

Implementation Method 1

A C8 hydrocarbon composition with a specific isomer distribution, optimized for both cobalt and rhodium hydroformylation processes, is achieved by oligomerizing a butene-containing C4 hydrocarbon stream using a heterogeneous nickel-containing catalyst

Methodology Applied
Scientific EffectCatalysis: Catalysis

Data Source

PatentEP4455114A1C8 hydrocarbon compositions and a process for their preparation
Publication Date: 2024.10.30 EVONIK OXENO GMBH & CO KG
  • EP4455114A1 patent drawing
  • EP4455114A1 patent drawing
  • EP4455114A1 patent drawing

AI summary

The invention relates to a C8 hydrocarbon composition with a specific isomer distribution and a process for producing such a composition by oligomerization. Furthermore, the present invention relates to the use of the C8 hydrocarbon composition thus produced in hydroformylation.