Olefin Conversion via Isomerization and Metathesis

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Solution Overview

Problem

Current processes for producing high purity alpha-olefins, such as 1-butene, 1-hexene, and 1-octene, are energy intensive due to the need for distillation to separate these olefins from their positional isomers, which have close boiling points, making them economically unattractive.

Innovation Solution

A process involving isomerization and metathesis reactions that convert propylene with a hydrocarbon mixture to form beta-olefins, which are then converted back to alpha-olefins using ethylene, allowing for easier separation and reducing the need for intensive fractionation systems like superfractionators.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Manufacturing precision

If distillation is used to separate alpha-olefins from positional isomers, then high purity alpha-olefins are obtained, but energy consumption increases significantly

Engineering Contradiction:
Improvepurity of alpha-olefinVSAvoidenergy consumption
Core Design Contradiction:
Manufacturing precisionVSUse of energy by moving object

Solution Approach 1:

The invention changes the chemical structure parameter of the olefin from alpha-position to beta-position through isomerization, which fundamentally alters the boiling point characteristics and enables easier separation. This parameter change transforms the separation problem from one requiring energy-intensive superfractionation to one amenable to conventional distillation

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention introduces beta-olefin as an intermediate substance in the production process. By converting alpha-olefin to beta-olefin and then back to alpha-olefin through controlled reactions, the process uses this intermediate to achieve both high purity and reduced energy consumption, as the beta-olefin intermediate has different separation characteristics

Inventive Principle:
Principle #24Intermediary (Mediator)

2Manufacturing precision

If superfractionators are used to separate 1-hexene from 2-hexene and 3-hexene, then high purity 1-hexene is produced, but the process becomes economically unattractive due to high operating costs

Engineering Contradiction:
Improvepurity of 1-hexeneVSAvoideconomic viability
Core Design Contradiction:
Manufacturing precisionVSEase of manufacture

Solution Approach 1:

The invention applies parameter change by isomerizing 1-hexene to 2-hexene, which has different physical properties including boiling point. This parameter transformation allows separation through conventional distillation rather than requiring expensive superfractionators, thereby improving economic viability while maintaining product purity

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention uses inversion by first converting the desired product (1-hexene) to its isomer (2-hexene), separating the isomer, and then converting it back. This reverse approach avoids the need for direct separation of close-boiling isomers and reduces equipment costs and operating expenses

Inventive Principle:
Principle #13The other way round (Inversion)

3Manufacturing precision

If multiple superfractionators are deployed for 1-hexene production, then separation completeness is achieved, but device complexity and capital investment increase

Engineering Contradiction:
Improveseparation completenessVSAvoidnumber of fractionation towers
Core Design Contradiction:
Manufacturing precisionVSDevice complexity

Solution Approach 1:

The invention changes the chemical parameter of the hexene isomer from the 1-position to the 2-position, which creates sufficient boiling point difference to enable complete separation using a single conventional distillation tower instead of multiple superfractionators, thereby reducing device complexity

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention employs 2-hexene as an intermediate that facilitates separation. By converting 1-hexene to 2-hexene, performing the separation, and then converting back, the process uses this intermediate to achieve complete separation with simpler equipment, reducing the number of towers from multiple to one

Inventive Principle:
Principle #24Intermediary (Mediator)

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 significantly reduces energy consumption by simplifying the separation of alpha-olefins from their positional isomers, making the production of high purity alpha-olefins more economically viable without the need for energy-intensive distillation.

Implementation Method 1

contacting propylene and a hydrocarbon mixture comprising a mixture of olefins having a carbon number n with a first metathesis catalyst to form a metathesis product comprising a beta-olefin having a carbon number n+1, an alpha-olefin having a carbon number n−1

Methodology Applied
Scientific EffectMetathesis: Chemical Transport Reactions

Implementation Method 2

contacting a hydrocarbon mixture comprising linear butenes with an isomerization catalyst to form an isomerization product comprising 2-butenes and 1-butenes

Methodology Applied
Scientific EffectIsomerization: Chemical Transport Reactions

Implementation Method 3

fractionating the metathesis product to recover a fraction comprising the beta-olefin having a carbon number n+1

Methodology Applied
Scientific EffectDistillation: Distillation

Data Source

PatentUS9598331B2Olefin conversion process
Publication Date: 2017.03.21 LUMMUS TECHNOLOGY INC
  • US9598331B2 patent drawing
  • US9598331B2 patent drawing
  • US9598331B2 patent drawing

AI summary

Processes for the production of high purity alpha olefins from a mixture of olefins are disclosed. The processes may include: contacting propylene and a hydrocarbon mixture comprising a mixture of olefins having a carbon number n with a first metathesis catalyst to form a metathesis product comprising a beta-olefin having a carbon number n+1, an alpha-olefin having a carbon number n−1, as well as any unreacted propylene and olefins having a carbon number n. The metathesis product may be fractionated to recover a fraction comprising the beta-olefin having a carbon number n+1. Ethylene and the fraction comprising the beta-olefin having a carbon number n+1 may then be contacted with a second metathesis catalyst to form a second metathesis product comprising an alpha-olefin having a carbon number n and propylene, which may be fractionated to form a propylene fraction and a fraction comprising the alpha olefin having a carbon number n.