Fatty Acid Ester Separation for Metathesis Purity

Resolve Bottlenecks,
Find Innovative Solutions
Generate Solutions

Solution Overview

Problem

Current refining processes for natural oil feedstocks face inefficiencies in separating polyunsaturated fatty acid esters from monounsaturated fatty acid esters, leading to decreased market value and increased processing costs, as well as issues with cyclohexadiene formation and benzene production, which affect downstream separation processes.

Innovation Solution

A method involving the separation of polyunsaturated fatty acid esters and monounsaturated fatty acid esters using techniques such as simulated moving bed chromatography, crystallization, or other separation processes to achieve a high ratio of monounsaturated to polyunsaturated esters, followed by metathesis reactions to produce tailored metathesized products.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Ease of manufacture

If polyunsaturated fatty acid esters are not separated from monounsaturated fatty acid esters, then processing costs are reduced, but market value decreases and additional processing is required

Engineering Contradiction:
Improveprocessing costVSAvoidproduct purity
Core Design Contradiction:
Ease of manufactureVSManufacturing precision

Solution Approach 1:

The patent applies preliminary action by performing separation of polyunsaturated and monounsaturated fatty acid esters before the metathesis reaction. This pre-separation prevents the formation of cyclohexadiene and benzene that would otherwise require additional downstream processing, thereby reducing overall processing costs while ensuring high product purity.

Inventive Principle:
Principle #10Preliminary action

Solution Approach 2:

The patent segments the fatty acid ester mixture into distinct polyunsaturated and monounsaturated fractions through separation processes such as distillation or chromatography. This segmentation allows each fraction to undergo metathesis independently, preventing unwanted side reactions and improving both ease of manufacture and manufacturing precision.

Inventive Principle:
Principle #1Segmentation

2Quantity of substance

If polyunsaturated fatty acid esters are present in the metathesis feedstock, then feedstock utilization is maximized, but cyclohexadiene and benzene formation increases

Engineering Contradiction:
Improvefeedstock utilizationVSAvoidcyclohexadiene and benzene formation
Core Design Contradiction:
Quantity of substanceVSObject-generated harmful factors

Solution Approach 1:

The patent extracts polyunsaturated fatty acid esters from the feedstock before metathesis through separation processes. This extraction removes the source of cyclohexadiene and benzene formation while still allowing the remaining monounsaturated esters to be fully utilized in the metathesis reaction, thus eliminating harmful factors without sacrificing feedstock utilization.

Inventive Principle:
Principle #2Taking out (Extraction)

Solution Approach 2:

The patent converts the potentially harmful presence of polyunsaturated esters into a benefit by separating and utilizing them for other purposes. The separated polyunsaturated fraction can be used in alternative applications where its unsaturation is advantageous, while the monounsaturated fraction proceeds to metathesis without forming harmful byproducts.

Inventive Principle:
Principle #22Blessing in disguise (Convert harm into benefit)

3Manufacturing precision

If separation processes are implemented to remove polyunsaturated esters, then product quality improves, but processing complexity increases

Engineering Contradiction:
Improveproduct qualityVSAvoidprocessing complexity
Core Design Contradiction:
Manufacturing precisionVSDevice complexity

Solution Approach 1:

The patent utilizes parameter changes in physical properties such as boiling point differences between polyunsaturated and monounsaturated fatty acid esters. By exploiting these parameter differences through distillation or other separation processes, high product quality is achieved through relatively simple equipment without requiring complex multi-step procedures.

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 approach improves the yield and purity of downstream products, reduces the need for additional processing steps, and enhances the economic efficiency of the refining system by optimizing the separation and metathesis of fatty acid esters.

Implementation Method 1

separating the polyunsaturated fatty acid esters from the monounsaturated fatty acid esters using techniques such as simulated moving bed chromatography

Methodology Applied
Scientific EffectChromatography: Chromatography

Implementation Method 2

separating the polyunsaturated fatty acid esters from the monounsaturated fatty acid esters using techniques such as simulated moving bed chromatography, crystallization

Methodology Applied
Scientific EffectCrystallization: Crystallisation

Implementation Method 3

metathesizing the separated monounsaturated fatty acid ester composition in the presence of a metathesis catalyst to provide a metathesized product comprising metathesized monounsaturated fatty acid esters and at least one olefin

Methodology Applied
Scientific EffectCatalysis: Catalysis

Data Source

PatentEP3119738B1Systems and methods of refining natural oil feedstocks and derivatives thereof
Publication Date: 2019.01.30 ELEVANCE RENEWABLE SCIENCES INC
  • EP3119738B1 patent drawingFigure 1
  • EP3119738B1 patent drawingFigure 2
  • EP3119738B1 patent drawingFigure 3

AI summary

Systems and methods are disclosed for refining natural oil feedstocks. In some embodiments, the methods comprise transesterifying glycerides in a natural oil feedstock to provide a transesterified product comprising monounsaturated fatty acid esters and polyunsaturated fatty acid esters. In some embodiments, the methods comprise separating the polyunsaturated fatty acid esters from the monounsaturated fatty acid esters (or vice versa), to provide a separated monounsaturated fatty acid ester composition having a ratio of at least 10 parts by weight of monounsaturated fatty acid esters for every 1 part by weight of polyunsaturated fatty acid esters.