Olefin Trimerization via Dimer Recycling and Catalyst Control

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Solution Overview

Problem

Current methods for polymerizing olefins produce a mixture of polymers with poor selectivity, requiring complex separation techniques to obtain desired polymer species, and previous processes have not efficiently produced isododecenes, which are olefin trimers, due to broad oligomer distributions and low conversion rates.

Innovation Solution

A process involving a reactor with a dimerization catalyst, an oxygen-containing moderator, and controlled temperature and pressure conditions for catalytic dimerization and addition reactions, where olefin monomers and dimers are recycled to enhance trimer production, allowing for high selectivity and simplification of the production process by eliminating the need for additional separation techniques.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Productivity

If acid-catalyzed isobutene oligomerization is used to produce olefin trimers, then olefin conversion is achieved, but a broad oligomer distribution is generated with poor selectivity towards trimers

Engineering Contradiction:
Improveolefin conversionVSAvoidtrimer selectivity
Core Design Contradiction:
ProductivityVSManufacturing precision

Solution Approach 1:

The patent applies parameter changes by carefully controlling the mass ratio of olefin monomers to olefin dimers in the reactor feed (specifically 1:8 to 1:15), maintaining temperature between 40-140°C and pressure at 10-40 bar. These parameter optimizations shift the oligomer distribution towards dominant trimer production while maintaining high conversion rates.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent implements feedback by recycling the lighter product containing olefin dimers back to the reactor. This creates a closed-loop system where dimers that would otherwise be wasted are continuously fed back to participate in trimer formation reactions, thereby improving both conversion efficiency and trimer selectivity over time.

Inventive Principle:
Principle #23Feedback

2Manufacturing precision

If complex separation techniques are used to obtain desired polymer species from polymer mixtures, then product purity is improved, but process complexity increases

Engineering Contradiction:
Improveproduct purityVSAvoidseparation process complexity
Core Design Contradiction:
Manufacturing precisionVSDevice complexity

Solution Approach 1:

The patent applies preliminary action by pre-controlling the reaction conditions to produce a narrow oligomer distribution dominated by trimers. By optimizing the monomer-to-dimer mass ratio and reaction parameters before separation, the patent minimizes the complexity of downstream separation processes while ensuring high product purity.

Inventive Principle:
Principle #10Preliminary action

3Productivity

If olefin monomers are effectively converted into desired polymers, then productivity is improved, but separation of lighter components becomes more difficult

Engineering Contradiction:
Improvemonomer conversion efficiencyVSAvoidseparation process complexity
Core Design Contradiction:
ProductivityVSDevice complexity

Solution Approach 1:

The patent implements feedback by recycling lighter components (olefin dimers) back to the reactor. This converts what would be separation waste into valuable reactants, simultaneously improving monomer conversion efficiency and eliminating the need for complex separation of lighter components.

Inventive Principle:
Principle #23Feedback

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 achieves high selectivity for olefin trimers, with over 90% conversion of monomers to trimers, simplifying the production process and enabling the recovery of reactive species, and allows for flexible production in both single and multiple reactor systems.

Implementation Method 1

reactor containing a dimerization catalyst: olefin monomer feed and at least one oxygen-containing moderator; operating the reactor at a temperature selected from the range 40-140°C and at a pressure selected from the range 10-40bar for carrying out catalytic dimerization reactions between olefin monomers and olefin monomers, and addition reactions between olefin monomers and olefin dimers

Methodology Applied
Scientific EffectCatalysis: Catalysis

Implementation Method 2

distilling the reactor outlet stream to separate at least one lighter product comprising olefin dimers, and a heavier bottom product comprising olefin trimers

Methodology Applied
Scientific EffectDistillation: Distillation

Data Source

PatentEP4001248B1Olefin trimerization
Publication Date: 2023.03.29 NESTE OYJ
  • EP4001248B1 patent drawingFigure 1~2
  • EP4001248B1 patent drawingFigure 3
  • EP4001248B1 patent drawingFigure 4

AI summary

The present disclosure relates to a process and a production unit that are used to catalytically manufacture olefin trimers from olefin monomers, and wherein olefin dimers are recycled after dimerization reaction, and reacted with olefin monomers in an addition reaction.