Hydrocarbon Stream Purification Using Amine Salt Distillation

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Solution Overview

Problem

Current methods fail to effectively remove organic amines from hydrocarbon streams containing linear alpha olefins and their isomers due to close boiling points, leading to high investment costs and incomplete product purification, as conventional and extractive distillation techniques are ineffective without suitable azeotropes or extraction agents.

Innovation Solution

A method involving conventional distillation under atmospheric pressure to separate a significant amount of organic amines and isomers from hydrocarbon streams, where the boiling points of linear alpha olefins, isomers, and amines differ by up to 5°C, allowing for the removal of 5-95% of isomers with the amine in an amine/isomer-rich fraction, without the need for acid-resistant materials or external extraction agents.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Manufacturing precision

If conventional distillation is used to separate amines from hydrocarbon stream, then separation is attempted, but separation effectiveness is poor due to close boiling points

Engineering Contradiction:
Improveseparation effectivenessVSAvoidamine concentration in product
Core Design Contradiction:
Manufacturing precisionVSQuantity of substance

Solution Approach 1:

Amine salts act as an intermediary substance that enables separation. The hydrocarbon stream is contacted with an aqueous phase containing amine salts, which selectively extract free amine from the hydrocarbon phase. This intermediary mechanism allows effective separation despite close boiling points by converting the separation problem from thermal to chemical selectivity.

Inventive Principle:
Principle #24Intermediary (Mediator)

2Manufacturing precision

If acid is used to convert amine to amine salt for extraction, then amine removal is achieved, but investment cost increases due to acid-resistant materials requirement

Engineering Contradiction:
Improveamine removal efficiencyVSAvoidinvestment cost
Core Design Contradiction:
Manufacturing precisionVSEase of manufacture

Solution Approach 1:

The invention uses readily available amine salts (such as ammonium carbonate, ammonium bicarbonate, or alkyl ammonium salts) that can be easily prepared and applied. These salts are inexpensive and do not require special handling or acid-resistant equipment, making the process economically viable without heavy investment in specialized materials.

Inventive Principle:
Principle #27Cheap short-living objects (Disposable)

3Quantity of substance

If amine is removed by acid reaction method, then amine is extracted, but isomers remain in hydrocarbon stream reducing product quality

Engineering Contradiction:
Improveamine concentrationVSAvoidproduct purity
Core Design Contradiction:
Quantity of substanceVSManufacturing precision

Solution Approach 1:

The invention applies partial action by performing multiple sequential extraction steps rather than attempting complete amine removal in a single step. Each extraction step removes a portion of the amine while the hydrocarbon stream passes through multiple stages, allowing progressive purification. This approach also enables some isomer separation to occur concurrently, improving overall product quality without requiring excessive processing.

Inventive Principle:
Principle #16Partial or excessive action

4Manufacturing precision

If distillation is used to separate linear alpha-olefins from isomers, then separation is attempted, but separation is ineffective due to close boiling points

Engineering Contradiction:
Improveolefin purityVSAvoidisomer content
Core Design Contradiction:
Manufacturing precisionVSQuantity of substance

Solution Approach 1:

Amine salts serve as a selective intermediary that preferentially binds to amine components while leaving linear alpha-olefins and isomers in the hydrocarbon phase. By removing the amine first through this chemical intermediary mechanism, subsequent separation of olefins from isomers can be more effectively achieved, as the interfering amine is no longer present to complicate the physical separation.

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 method significantly improves the purity of linear alpha-olefin products by removing a substantial amount of amines and isomers, reduces costs by enabling amine recycling, and avoids the use of acid-resistant materials, allowing for the marketing of hydrocarbon products with minimal amine content.

Implementation Method 1

removing a major amount of the organic amine from the hydrocarbon stream by distillation

Methodology Applied
Scientific EffectDistillation: Distillation

Implementation Method 2

the boiling points of the amine and the hydrocarbon stream, and especially fractions thereof, are very close

Methodology Applied
Scientific EffectBoiling point difference: Vapour Pressure

Data Source

PatentUS9284238B2Method for purification of a hydrocarbon stream containing olefin and amine
Publication Date: 2016.03.15 SAUDI BASIC INDUSTRIES CORP

AI summary

The present invention relates to a method for purification of a hydrocarbon stream containing linear alpha olefins, isomers thereof and at least one organic amine, the linear alpha olefins, isomers and the amine having boiling points under atmospheric pressure which differ by at most 5° C., comprising the step of removing a major amount of the organic amine from the hydrocarbon stream by distillation, wherein the distillation is carried out to that, together with the amine, between 5% and 95 wt % of the isomers, based on the total amount of the isomers in the hydrocarbon stream, are removed from the hydrocarbon stream in an amine/isomer-rich fraction.