Omega-7 Ethyl Ester Purification via Urea Complexation

Resolve Bottlenecks,
Find Innovative Solutions
Generate Solutions

Solution Overview

Problem

Current methods fail to efficiently isolate high purity Omega-3, 6, 7, & 9 fatty acid ethyl esters from natural sources, leading to suboptimal nutrition and cosmetic products due to impurities like saturated fats.

Innovation Solution

A method involving transesterification of natural oils with ethanol using various catalysts, followed by distillation and separation techniques such as urea complexation and adsorption chromatography to produce high purity fractions of Omega-3, 6, 7, & 9 ethyl esters, specifically achieving concentrations of at least 50% w/w C16:1n7 ethyl esters.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Manufacturing precision

If natural oils are directly used without purification, then the process is simple and quick, but the product contains impurities like saturated fats that reduce nutritional and cosmetic value

Engineering Contradiction:
Improvepurity of Omega-7 estersVSAvoidcomplexity of isolation process
Core Design Contradiction:
Manufacturing precisionVSDevice complexity

Solution Approach 1:

The patent divides the isolation process into multiple distinct stages: transesterification to convert fatty acids to ethyl esters, distillation to separate esters by boiling point, and chromatography to further purify based on polarity. Each stage targets specific impurities, progressively increasing purity from crude oil to high-purity Omega-7 esters.

Inventive Principle:
Principle #1Segmentation

Solution Approach 2:

The patent uses ethanol as an intermediary solvent in the transesterification reaction, converting non-polar fatty acids into more polar ethyl esters that can be more effectively separated. The urea derivative acts as an intermediary compound that forms complexes with saturated fat esters, enabling their selective removal from the mixture.

Inventive Principle:
Principle #24Intermediary (Mediator)

2Manufacturing precision

If multiple purification steps are applied to achieve high purity, then the purity of Omega-7 esters increases, but the production time and cost increase

Engineering Contradiction:
Improveconcentration of C16:1n7 ethyl estersVSAvoidproduction efficiency
Core Design Contradiction:
Manufacturing precisionVSProductivity

Solution Approach 1:

The patent performs transesterification as a preliminary step before purification, converting the fatty acid mixture into ethyl esters that have better separability characteristics. This preliminary chemical transformation enables more efficient subsequent separation steps, reducing the number of purification passes needed to achieve high purity.

Inventive Principle:
Principle #10Preliminary action

Solution Approach 2:

The patent exploits changes in physical parameters (boiling point, polarity) through chemical modification. Transesterification changes the molecular structure and polarity of fatty acids, making them amenable to separation by distillation and chromatography. The use of urea derivatives changes the polarity characteristics of saturated fat esters, enabling selective complexation and removal.

Inventive Principle:
Principle #35Parameter changes

3Reliability

If saturated fats are removed through synthesis and purification of ethyl esters, then the nutritional value increases, but the process complexity and resource consumption increase

Engineering Contradiction:
Improvebeneficial effects on healthVSAvoidresource consumption
Core Design Contradiction:
ReliabilityVSLoss of substance

Solution Approach 1:

The patent selectively discards saturated fat esters through complexation with urea derivatives, which form insoluble complexes that can be easily separated. The unsaturated Omega-7 esters remain in solution and are recovered in high purity. This selective discarding approach removes harmful components while preserving and concentrating beneficial ones.

Inventive Principle:
Principle #34Discarding and recovering

Solution Approach 2:

The patent replaces mechanical separation methods (which would require complex equipment and multiple passes) with chemical separation mechanisms. Transesterification followed by selective complexation and filtration achieves purification that would be difficult to obtain through mechanical means alone, reducing equipment complexity and resource consumption.

Inventive Principle:
Principle #28Mechanics substitution (Replace mechanical system)

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 enables the attainment of high purity Omega-7 esters with concentrations up to 90% w/w, effectively removing saturated fats and enhancing the nutritional and cosmetic value of derived products.

Implementation Method 1

separating the C16:0 and C16:1n7 ethyl esters of the second fraction to produce a third fraction of C16:0 ethyl esters and a fourth fraction comprising at least 50% w/w C16:1n7 ethyl esters

Methodology Applied
Scientific EffectComplexation: Absorption (physical)

Implementation Method 2

adsorption chromatography to produce high purity fractions of Omega-3, 6, 7, & 9 ethyl esters

Methodology Applied
Scientific EffectAdsorption: Adsorption

Implementation Method 3

distilling the ethyl esters to produce a first fraction comprising C18:1n9 ethyl esters and a second fraction comprising C16:0 and C16:1n7 ethyl esters

Methodology Applied
Scientific EffectDistillation: Distillation

Data Source

PatentUS10314871B2Isolation of Omega-7 fatty acid ethyl esters from natural oils
Publication Date: 2019.06.11 HELIAE DEVELOPMENT LLC
  • US10314871B2 patent drawing
  • US10314871B2 patent drawing
  • US10314871B2 patent drawing

AI summary

Methods of producing high purity palmitoleic acid esters from natural oils are disclosed. The natural oils may comprise plant oil, nut oil, microalgae oil, and fish oil. The methods of processing the natural oil comprise transesterification with ethanol as the reacting solvent to produce ethyl esters. Methods of producing a high purity fraction of Omega-3, 6, & 9 fatty acid esters from natural oils are also disclosed. The high purity fatty acid esters may be used in nutrition, cosmetic, and nutraceutical products.