Selective Ethylene Oligomerization for Flexible Benzene Production

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Solution Overview

Problem

Conventional methods of benzene production from crude oil are becoming increasingly expensive due to rising demand, and alternative methods using natural gas as a starting material are desirable to lower costs.

Innovation Solution

A method involving selective-higher-olefin oligomerization of ethylene using specific catalysts to produce C6 and C8 hydrocarbons, followed by hydrotreating and aromatization processes to yield benzene, with integrated systems for ethylene conversion into benzene and other valuable hydrocarbons.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Ease of manufacture

If conventional crude oil-based methods are used for benzene production, then benzene can be produced through established refining processes, but production costs increase due to rising crude oil demand and prices

Engineering Contradiction:
Improvebenzene production costVSAvoidcrude oil availability
Core Design Contradiction:
Ease of manufactureVSQuantity of substance

Solution Approach 1:

The invention changes the fundamental parameter of feedstock source from crude oil to natural gas (specifically ethylene). This parameter change enables benzene production through a different chemical pathway (oligomerization of ethylene to C6-C8 hydrocarbons followed by aromatization), thereby reducing dependence on crude oil and mitigating cost increases associated with rising crude oil demand

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention introduces C6-C8 hydrocarbon intermediates (specifically 1-hexene and 1-octene) as mediators in the transformation from ethylene to benzene. These intermediates are produced through selective oligomerization and then converted to benzene via aromatization, providing a multi-step pathway that enables cost-effective benzene production from natural gas feedstock

Inventive Principle:
Principle #24Intermediary (Mediator)

2Manufacturing precision

If selective-higher-olefin oligomerization is used to produce C6 and C8 hydrocarbons from ethylene, then high purity 1-hexene and 1-octene can be obtained, but additional processing steps (hydrotreating and aromatization) are required

Engineering Contradiction:
Improvepurity of 1-hexene and 1-octeneVSAvoidnumber of processing steps
Core Design Contradiction:
Manufacturing precisionVSDevice complexity

Solution Approach 1:

The invention performs preliminary selective oligomerization to produce high-purity C6 and C8 hydrocarbons (1-hexene and 1-octene) with specific purity ranges (60-99.9 wt.% for 1-hexene and 95-99.3 wt.% for 1-octene) before subsequent hydrotreating and aromatization steps. This preliminary purification enables the catalyst to function effectively in later stages and ensures high benzene yield

Inventive Principle:
Principle #10Preliminary action

Solution Approach 2:

The invention segments the overall benzene production process into distinct functional stages: (1) selective oligomerization of ethylene to C6-C8 hydrocarbons, (2) hydrotreating to saturate olefins, and (3) aromatization to produce benzene. This segmentation allows each stage to be optimized independently, with the first stage focusing on producing high-purity intermediates that enable effective downstream processing

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 method achieves high purity levels of 1-hexene and 1-octene and produces benzene efficiently, along with other valuable hydrocarbons like toluene and xylene, while reducing production costs by utilizing natural gas as a starting material.

Implementation Method 1

contacting, in an oligomerization process, ethylene with a selective-higher-olefin catalyst to yield an oligomerization reactor effluent comprising 1) C6 hydrocarbons which include 1-hexene and 2) C8 hydrocarbons which include 1-octene

Methodology Applied
Scientific EffectOligomerization: Chemical Bonding

Implementation Method 2

contacting, in a hydrotreating process, 1-hexene, 1-octene, or both 1-hexene and 1-octene recovered from the oligomerization reactor effluent with a hydrogenation catalyst to yield an aromatization feed comprising hexane, octane, or both

Methodology Applied
Scientific EffectHydrogenation: Hydrogenation

Implementation Method 3

contacting, in an aromatization process, the aromatization feed with an aromatization catalyst to yield reformate effluent comprising benzene

Methodology Applied
Scientific EffectAromatization: Chemical Bonding

Data Source

PatentUS12435016B2Flexible benzene production via selective-higher-olefin oligomerization of ethylene
Publication Date: 2025.10.07 CHEVRON PHILLIPS CHEMICAL COMPANY LP
  • US12435016B2 patent drawing
  • US12435016B2 patent drawing
  • US12435016B2 patent drawing

AI summary

The present disclosure relates to the integration of systems and methods associated with steam cracking, oligomerization reactions, hydrogenation reactions, and aromatization reactions for the production of benzene via the hydrogenation of oligomers produced from ethylene. In some aspects, the disclosed systems and methods utilize one or more of an oligomerization process, a hydrotreating process, and an aromatization process for producing a benzene comprising effluent. In further aspects, the systems and methods disclosed herein utilize one or more selective oligomerization catalyst systems.