C20 Trisubstituted Olefin Production With Controlled C40 Dimer Formation

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Solution Overview

Problem

There is a need to find additional uses for C20 2-substituted alpha olefins synthesized from branched C10 olefins, as existing applications are limited.

Innovation Solution

A process involving contacting branched C10 olefins with a dimerization catalyst to form C20 2-substituted alpha olefins, followed by an acidic catalyst to produce C20 trisubstituted olefins, including specific isomers such as 5-propyl-6-methyl-9-propyl-tridec-5-ene and others, with controlled reaction conditions to minimize C40 dimer formation.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Productivity

If branched C10 olefins are contacted with a dimerization catalyst to form C20 2-substituted alpha olefins, then the productivity of C20 olefins is improved, but C40 dimer by-products are generated

Engineering Contradiction:

ImproveC20 olefin productionVSAvoidC40 dimer by-products

Core Design Contradiction:

ProductivityVSObject-generated harmful factors

Solution Approach 1:

The patent applies parameter changes by carefully controlling reaction conditions including temperature (50-150°C), pressure (1-50 atm), and contact time (0.5-10 hours) to optimize the dimerization reaction. By adjusting these parameters, the process maximizes C20 olefin formation while minimizing C40 dimer by-product generation through precise control of reaction kinetics and thermodynamics

Inventive Principle:

Principle #35Parameter changes

2Adaptability or versatility

If C20 2-substituted alpha olefins are contacted with an acidic catalyst to form C20 trisubstituted olefins, then new valuable products are generated, but reaction selectivity must be controlled

Engineering Contradiction:

Improveproduct applicationsVSAvoidreaction selectivity

Core Design Contradiction:

Adaptability or versatilityVSManufacturing precision

Solution Approach 1:

The patent utilizes parameter changes by optimizing acidic catalyst selection (ion-exchange resins, zeolites, or solid acids), temperature (40-100°C), and contact time (1-24 hours) to control the isomerization and oligomerization reactions. These parameter adjustments ensure high selectivity for desired C20 trisubstituted olefin products while minimizing unwanted by-products, enabling versatile product applications

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 generates valuable C20 trisubstituted olefins that can be used as feedstocks for paper sizing agents and polyalphaolefins, expanding their applications beyond existing uses.

Implementation Method 1

contacting a branched C10 olefin composition with a dimerization catalyst or a dimerization catalyst system to form a C20 2-substituted alpha olefin composition

Methodology Applied

Scientific EffectCatalysis: Catalysis

Implementation Method 2

contacting the C20 2-substituted alpha olefin composition with an acidic catalyst to form a C20 trisubstituted olefin composition including a C20 trisubstituted olefin

Methodology Applied

Scientific EffectCatalysis: Catalysis

Data Source

PatentUS20250382242A1C20 trisubstituted olefins produced by acidic catalyzed reaction of c20 2-substituted alpha olefins

Publication Date: 2025.12.18 CHEVRON PHILLIPS CHEMICAL COMPANY LP

AI summary

C20 trisubstituted olefins are produced from C20 2-substituted alpha olefins, which are produced from branched C10 olefins.