Pyrrole-Based Oligomerization Catalyst for 1-Hexene Selectivity

Resolve Bottlenecks,
Find Innovative Solutions
Generate Solutions

Solution Overview

Problem

Current oligomerization catalyst systems for producing 1-hexene face challenges in activity, selectivity, and cost-effectiveness, with a need for improved efficiency and selectivity to C6 products.

Innovation Solution

A catalyst system comprising a transition metal compound (such as chromium, nickel, cobalt, iron, or copper) combined with a pyrrole compound having specific structural features and an alkyl aluminum compound, optimized for oligomerization processes to enhance productivity and selectivity to 1-hexene.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Productivity

If conventional chromium catalyst systems are used for oligomerization, then the process can proceed, but catalyst activity and selectivity to C6 products are insufficient

Engineering Contradiction:
Improvecatalyst activityVSAvoidselectivity to C6 products
Core Design Contradiction:
ProductivityVSReliability

Solution Approach 1:

The patent employs a composite catalyst system comprising chromium(III) carboxylate, pyrrole compound, and metal alkyl components. This composite approach combines multiple substances to achieve synergistic effects, where the chromium provides catalytic activity while the pyrrole compound enhances selectivity to C6 oligomers, resolving the contradiction between activity and selectivity

Inventive Principle:
Principle #40Composite materials

Solution Approach 2:

The patent optimizes specific parameters including the molecular structure of the pyrrole compound (with particular attention to substituents at positions 2 and 5), the ratio of catalyst components, and reaction conditions such as temperature and pressure. These parameter changes enable simultaneous improvement of catalyst activity and C6 selectivity

Inventive Principle:
Principle #35Parameter changes

2Productivity

If catalyst system components are added to improve activity, then productivity increases, but system complexity and cost increase

Engineering Contradiction:
Improveoligomerization productivityVSAvoidcatalyst system complexity
Core Design Contradiction:
ProductivityVSDevice complexity

Solution Approach 1:

The pyrrole compound serves multiple functions simultaneously: it acts as a ligand for the chromium center, modifies the electronic properties of the catalyst, and specifically directs selectivity toward C6 products. This multi-functionality reduces the need for additional specialized components, maintaining system simplicity while enhancing productivity

Inventive Principle:
Principle #6Universality (Multi-functionality)

3Ease of manufacture

If conventional pyrrole compounds are used, then the catalyst system is simple, but selectivity to 1-hexene is insufficient

Engineering Contradiction:
Improvecatalyst system simplicityVSAvoidselectivity to 1-hexene
Core Design Contradiction:
Ease of manufactureVSManufacturing precision

Solution Approach 1:

The patent introduces specific local structural features into the pyrrole compound, particularly substituents at the 2 and 5 positions of the pyrrole ring. These localized structural modifications create specific steric and electronic environments at the catalytic site that enhance 1-hexene selectivity without requiring complete redesign of the entire catalyst system

Inventive Principle:
Principle #3Local quality

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 described catalyst system achieves improved catalyst activity, selectivity, and productivity, leading to higher purity and efficiency in producing 1-hexene, addressing the limitations of existing systems.

Implementation Method 1

A catalyst system comprising a transition metal compound (such as chromium, nickel, cobalt, iron, or copper) combined with a pyrrole compound having specific structural features and an alkyl aluminum compound, optimized for oligomerization processes

Methodology Applied
Scientific EffectCatalysis: Catalysis

Data Source

PatentEP2563511B1Oligomerization catalyst system and process for oligomerizing olefins
Publication Date: 2016.09.14 CHEVRON PHILLIPS CHEMICAL COMPANY LP
  • EP2563511B1 patent drawingFigure 1
  • EP2563511B1 patent drawingFigure 2
  • EP2563511B1 patent drawing

AI summary

Among other things, this disclosure provides an olefin oligomerization system and process, the system comprising: a) a transition metal compound; b) a pyrrole compound having a hydrogen atom on at the 5- position or the 2- and 5- position of a pyrrole compound and having a bulky substituent located on each carbon atom adjacent to the carbon atom bearing a hydrogen atom at the 5- position or the 2- and 5- position of a pyrrole compound. These catalyst system have significantly improved productivities, selectivities to 1-hexene, and provides higher purity 1-hexene within the C6 fraction than catalyst systems using 2,4-dimethyl pyrrole.