Alpha Olefin Isomerization via Transition Metal and Clay Catalysts

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Solution Overview

Problem

Current isomerization processes of alpha olefins to internal olefins often result in substantial oligomer formation, which reduces the effectiveness of alkyl succinyl anhydride (ASA) sizing efficiency and leads to deposits in paper mills.

Innovation Solution

A multi-step process involving the combination of 1-alkenes with a catalyst formed by Group VIII transition metal salts and alkylaluminum compounds, followed by acid washed clay, to achieve a mixture with a balanced distribution of alkene isomers and low oligomer levels, conducted in the absence of water and oxygen to minimize oligomer formation.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Productivity

If acid catalysts are used for isomerization of alpha olefins, then isomerization reaction occurs, but substantial oligomer formation occurs as side reaction

Engineering Contradiction:
Improveisomerization reaction efficiencyVSAvoidoligomer formation
Core Design Contradiction:
ProductivityVSObject-generated harmful factors

Solution Approach 1:

The patent divides the isomerization process into two distinct stages: first stage uses transition metal catalysts for initial isomerization, second stage uses acid-washed clay for further isomerization and oligomer removal. This segmentation allows each stage to be optimized independently, achieving complete isomerization while minimizing oligomer formation.

Inventive Principle:
Principle #1Segmentation

Solution Approach 2:

The patent introduces acid-washed clay as an intermediary substance that facilitates the conversion of internal alkenes to desired isomers while simultaneously removing oligomers through adsorption. This intermediary plays a dual role: promoting useful reaction and eliminating harmful byproducts.

Inventive Principle:
Principle #24Intermediary (Mediator)

2Productivity

If conventional isomerization processes are used, then internal olefins are produced, but oligomers reduce ASA sizing efficiency

Engineering Contradiction:
Improveinternal olefin productionVSAvoidASA sizing efficiency
Core Design Contradiction:
ProductivityVSReliability

Solution Approach 1:

The patent extracts and removes oligomers from the reaction mixture using acid-washed clay, which adsorbs oligomers while allowing desired internal olefins to pass through. This extraction ensures high purity of ASA sizing agents, maintaining reliability of the final product.

Inventive Principle:
Principle #2Taking out (Extraction)

Solution Approach 2:

The patent changes the chemical environment parameters by introducing acid-washed clay with specific surface properties and acidity, which alters the reaction pathway to favor isomerization over oligomerization, thereby improving both productivity and reliability.

Inventive Principle:
Principle #35Parameter changes

3Device complexity

If single-step isomerization is used, then process is simple, but oligomer formation is substantial

Engineering Contradiction:
Improveprocess simplicityVSAvoidoligomer formation
Core Design Contradiction:
Device complexityVSObject-generated harmful factors

Solution Approach 1:

The patent segments the catalytic system into two functional components: transition metal catalysts for initial isomerization and acid-washed clay for secondary isomerization and oligomer removal. This segmentation increases process complexity but dramatically reduces oligomer formation, achieving superior product quality.

Inventive Principle:
Principle #1Segmentation

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 process produces a final mixture with a more even distribution of alkene isomers and significantly reduced oligomer levels, enhancing the efficiency of ASA production and preventing deposits in paper mills.

Implementation Method 1

combining at least one 1-alkene in liquid phase at a temperature of from about 50° C. to about 200° C. with a catalyst, wherein the catalyst is formed by contacting (i) at least one Group VIII transition metal salt and (ii) at least one alkylaluminum compound

Methodology Applied
Scientific EffectCatalysis: Catalysis

Implementation Method 2

combining the first mixture of step (a) with at least one acid washed clay, thereby forming a final mixture

Methodology Applied
Scientific EffectCatalysis: Catalysis

Data Source

PatentUS7271308B2Process for isomerization of alpha olefins to internal olefins
Publication Date: 2007.09.18 SOLENIS TECHNOLOGIES LP

AI summary

The present invention relates to embodiments for a process for the isomerization of at least one alpha olefin to an internal olefin via a multi-step process resulting in a mixture comprising alkene isomers and a low level of oligomers. According to the present invention an alkylaluminum compound is used in combination with the Group VIII transition metal salt for interaction with the latter, and thereby generating catalytically active species for the isomerization of 1-alkenes to internal alkenes, wherein this mixture is subsequently combined with an acid washed clay.