Polymerizing Internal Olefins with Transition Metal Catalysts

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Solution Overview

Problem

Current processes for polymerizing low molecular weight alpha-olefins and internal olefins, such as linear and branched olefins, are limited in producing high cetane number diesel fuel and base stocks, as they tend to form highly branched products, and there is a need for more effective catalyst systems to upgrade these olefins into higher value products.

Innovation Solution

A process involving the use of a catalyst compound comprising a group 8, 9, or 10 transition metal with a heteroatom, such as fluorine, to polymerize C2-C30 alpha-olefins, linear C4-C30 internal olefins, or branched C5-C30 internal olefins, resulting in C6-C100 polyolefin products with controlled methylene and methyl content, which can be hydrogenated to achieve a cetane number of 30 or greater.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If conventional catalyst systems are used for polymerizing low molecular weight olefins, then the polymerization process can proceed, but the products become highly branched which lowers the cetane number

Engineering Contradiction:
Improvecetane numberVSAvoidbranching structure
Core Design Contradiction:
ReliabilityVSShape

Solution Approach 1:

The patent changes the chemical parameters of the catalyst system by using group 8, 9, or 10 transition metals with specific ligands (such as fluorine-containing ligands) instead of conventional acid catalysts. This parameter change in catalyst composition directly controls the polymerization mechanism to produce linear products with high cetane numbers while avoiding excessive branching.

Inventive Principle:
Principle #35Parameter changes

2Productivity

If homogeneous catalysts are used in liquid phase for butenes oligomerization, then the process can achieve good conversion, but the catalyst system becomes complex and difficult to separate

Engineering Contradiction:
Improveconversion efficiencyVSAvoidcatalyst system complexity
Core Design Contradiction:
ProductivityVSDevice complexity

Solution Approach 1:

The patent employs ionic liquids as intermediary solvent systems that can dissolve both the transition metal catalyst and the olefin substrates. This intermediary medium enables homogeneous catalysis with high conversion while the ionic liquid's unique properties facilitate catalyst recovery and reduce system complexity compared to conventional organic solvents.

Inventive Principle:
Principle #24Intermediary (Mediator)

3Ease of operation

If branched internal olefins are polymerized using conventional catalysts, then the reaction can proceed, but the products have poor flow properties and low thickening efficiency

Engineering Contradiction:
Improveflow propertiesVSAvoidmolecular structure linearity
Core Design Contradiction:
Ease of operationVSShape

Solution Approach 1:

The patent changes the catalyst parameters to use transition metals with specific electronic configurations and ligand environments that favor linear chain growth over branching. This parameter change in catalyst chemistry directs the polymerization to produce linear polyolefins with improved flow properties and high thickening efficiency, even when starting from branched internal olefins.

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 process produces polyolefin products with improved cetane number, flow properties, and thickening efficiency, suitable for high-quality diesel fuel and base stocks, while effectively utilizing low molecular weight internal olefins that were previously underutilized.

Implementation Method 1

A process involving the use of a catalyst compound comprising a group 8, 9, or 10 transition metal with a heteroatom, such as fluorine, to polymerize C2-C30 alpha-olefins, linear C4-C30 internal olefins, or branched C5-C30 internal olefins

Methodology Applied
Scientific EffectCatalysis: Catalysis

Implementation Method 2

which can be hydrogenated to achieve a cetane number of 30 or greater

Methodology Applied
Scientific EffectHydrogenation: Hydrogenation

Data Source

PatentUS11713364B2Processes for polymerizing alpha-olefins, internal olefins and compositions thereof
Publication Date: 2023.08.01 EXXONMOBIL TECHNOLOGY & ENGINEERING CO
  • US11713364B2 patent drawing
  • US11713364B2 patent drawing
  • US11713364B2 patent drawing

AI summary

The present disclosure provides base stocks and or diesel fuel, and processes for producing such base stocks and or diesel fuel by polymerizing alpha-olefins and internal olefins. The present disclosure further provides polyolefin products useful as base stocks and or diesel fuel. In at least one embodiment, a process includes: i) introducing, neat or in the presence of a solvent, a feed comprising a branched C5-C30 internal olefin, with a catalyst compound comprising a group 8, 9, 10, or 11 transition metal and at least one heteroatom and ii) obtaining a C6-C100 polyolefin product having one olefin, a methylene content of from about 1 wt % to about 98 wt %, and or a methyl content of from about 1 wt % to about 75 wt %. The feed may further include a linear C4-C30 internal olefin, a C2-C30 alpha-olefin, or a mixture thereof.