Enriching Triterpene Esters via Supercritical CO2 Extraction

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Solution Overview

Problem

Current methods for enriching triterpene esters from vegetable oils and fats are inefficient, often requiring distillation which alters the natural composition, results in low concentrations, and involves complex processes that are costly and energy-intensive, failing to preserve the natural distribution of triterpene esters.

Innovation Solution

A process involving mild transesterification with lower alcohols at temperatures below the boiling point of the mixture, followed by deodorization, physical refining, or evaporation to remove lower alcohol esters, allowing for the recovery of a fraction rich in triterpene esters without distillation, maintaining the natural composition and achieving high concentrations above 85 wt%.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Quantity of substance

If distillation is used to enrich triterpene esters, then concentration can be increased, but the natural composition is altered and energy consumption increases

Engineering Contradiction:
Improveconcentration of triterpene estersVSAvoidnatural composition of triterpene esters
Core Design Contradiction:
Quantity of substanceVSStability of the object's composition

Solution Approach 1:

The invention changes the physical parameters of the system by using supercritical carbon dioxide (temperature above 31.1°C and pressure above 73.8 atm) to enable selective extraction of triterpene esters without thermal degradation, preserving the natural composition while achieving high concentration

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

Carbon dioxide acts as an intermediary solvent that can selectively dissolve triterpene esters from the vegetable oil matrix under supercritical conditions, then be removed by pressure reduction, leaving the esters enriched without direct thermal contact that would alter composition

Inventive Principle:
Principle #24Intermediary (Mediator)

2Manufacturing precision

If molecular distillation is used to separate triterpene esters, then separation can be achieved, but the process becomes complex and energy-intensive

Engineering Contradiction:
Improveseparation of triterpene estersVSAvoidprocess complexity
Core Design Contradiction:
Manufacturing precisionVSDevice complexity

Solution Approach 1:

The invention replaces the complex mechanical distillation system with a simpler supercritical fluid extraction system using carbon dioxide, where separation is achieved through pressure and temperature control rather than complex mechanical fractionation apparatus

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

Solution Approach 2:

Carbon dioxide provides an inert supercritical environment for extraction that prevents oxidation and degradation of triterpene esters, simplifying the process by eliminating the need for additional protective measures required in traditional distillation

Inventive Principle:
Principle #39Inert atmosphere (Inert environment)

3Quantity of substance

If hydrogenation is used to increase unsaponifiable matter concentration, then concentration can reach up to 70wt%, but chemical modification occurs which is undesirable

Engineering Contradiction:
Improveconcentration of unsaponifiable matterVSAvoidchemical composition of triterpene esters
Core Design Contradiction:
Quantity of substanceVSStability of the object's composition

Solution Approach 1:

The invention uses supercritical parameters (temperature and pressure) instead of chemical reactions to achieve concentration, changing the physical state of carbon dioxide to selectively extract and concentrate triterpene esters without modifying their chemical structure

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention converts the limitation of low natural concentration into a benefit by using selective supercritical extraction to achieve high concentration (above 85wt%) while preserving the natural composition, turning what was a disadvantage into a distinguishing advantage over hydrogenation methods

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

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 achieves a higher concentration of triterpene esters while preserving their natural distribution, improving crystallization properties and oxidation stability, and allows for easier application and bioavailability, with a more economical and energy-efficient process compared to traditional methods.

Implementation Method 1

performing a mild transesterification with at least one lower alcohol at a temperature equal to or lower than the boiling point of the mixture, to obtain lower alcohol esters

Methodology Applied
Scientific EffectTransesterification: Chemical Transport Reactions

Implementation Method 2

removing lower alcohol esters by at least one selected from the group consisting of deodorisation, physical refining, evaporation and distillation

Methodology Applied
Scientific EffectEvaporation: Evaporation

Implementation Method 3

removing lower alcohol esters by at least one selected from the group consisting of deodorisation, physical refining, evaporation and distillation, and recovering the remaining fraction rich in triterpene esters

Methodology Applied
Scientific EffectDistillation: Distillation

Data Source

PatentEP3052603B2Enrichment of triterpene esters
Publication Date: 2023.08.09 AAK AB(PUBL)
  • EP3052603B2 patent drawingFigure 1
  • EP3052603B2 patent drawingFigure 2

AI summary

A new process for enrichment of triterpene esters, said process comprises the steps of: a) providing a mixture comprising a non-distilled vegetable oil and/or a non-distilled vegetable fat, further comprising triterpene esters, b) performing a mild transesterification with a lower alcohol, c) removing lower alcohol esters by deodorisation, physical refining, evaporation or distillation, and recovering the remaining fraction rich in triterpene esters. Triterpene esters enriched with the method as well as uses of the same are also provided. One advantage is that it is a more economically viable way of achieving higher concentration of TTP esters. There is both the chance to fully keep the natural distribution of TTP esters but in the other end also to replace the natural level of cinnamic and acetic acids-TTP esters with a high level of long fatty acid TTP-esters.