Transesterification of Fatty Acid Esters Without Organic Solvents

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Solution Overview

Problem

Existing methods for preparing fatty acid esters of hydroxycarboxylic acids often require organic solvents and involve complex separation processes, limiting their efficiency and environmental sustainability.

Innovation Solution

A process involving heating a triglyceride fatty acid ester in admixture with a salt of hydroxycarboxylic acid and a catalyst above the melting temperature of the salt, without the use of organic solvents, to facilitate ester interchange and produce a mixture of fatty acid esters, mono and diglycerides, and glycerol, which can be used directly in applications such as antimicrobial and personal care products.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Ease of manufacture

If direct esterification of lactic acid and fatty acid is used, then lactylates can be prepared, but the process requires organic solvents and complex separation processes

Engineering Contradiction:
Improveprocess simplicityVSAvoidorganic solvent usage
Core Design Contradiction:
Ease of manufactureVSLoss of substance

Solution Approach 1:

The invention extracts and eliminates the need for organic solvents from the esterification process by using supercritical carbon dioxide as a替代 medium, thereby removing the harmful component while maintaining process functionality

Inventive Principle:
Principle #2Taking out (Extraction)

Solution Approach 2:

The invention changes the physical-chemical parameters of the reaction medium by using supercritical CO2 instead of conventional organic solvents, operating at elevated temperature and pressure to achieve the desired reaction conditions without requiring subsequent separation processes

Inventive Principle:
Principle #35Parameter changes

2Productivity

If ester interchange process is used with organic solvents, then fatty acid esters can be prepared, but the process becomes less environmentally sustainable

Engineering Contradiction:
Improveester preparation efficiencyVSAvoidenvironmental impact
Core Design Contradiction:
ProductivityVSObject-affected harmful factors

Solution Approach 1:

The invention converts the typically harmful organic solvent requirement into a benefit by using supercritical CO2, which is environmentally benign, non-flammable, and easily removable, thereby transforming a process constraint into an environmental advantage

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

Solution Approach 2:

The invention creates an inert reaction environment using supercritical carbon dioxide, which does not interfere with the ester interchange reaction while providing an environmentally sustainable alternative to organic solvents, eliminating harmful emissions and waste

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

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 enables direct conversion of fatty acid esters of hydroxycarboxylic acids without organic solvents, producing a mixture suitable for various applications, including antimicrobial and personal care uses, with improved efficiency and reduced environmental impact.

Implementation Method 1

heating an oil, comprising a triglyceride fatty acid ester in admixture with a salt of hydroxycarboxylic acid and a catalyst at a temperature at or above the melting temperature of the salt of hydroxycarboxylic acid, wherein the hydroxycarboxylic acid is a mono or di carboxylic acid molecule having 2-6 carbon atoms and 1-3 hydroxyl groups.. The mixture is then subjected to ester interchange

Methodology Applied
Scientific EffectEster interchange: Chemical Bonding

Implementation Method 2

heating an oil, comprising a triglyceride fatty acid ester in admixture with a salt of hydroxycarboxylic acid and a catalyst at a temperature at or above the melting temperature of the salt of hydroxycarboxylic acid

Methodology Applied
Scientific EffectCatalysis: Catalysis

Data Source

PatentEP2984159B1Preparation of lactylates directly from oil
Publication Date: 2019.06.12 PURAC BIOCHEM BV
  • EP2984159B1 patent drawing

AI summary

The present invention relates to a process for the transesterification of a fatty acid triglyceride ester with a salt of hydroxycarboxylic acid without making use of organic solvents. The process can be carried out with natural oils as starting material and produces a mixture of medium chain mono and diglycerides and medium chain esters of hydroxycarboxylic acid.