PUFA Alkyl Ester Composition With Low 3-MCPD Formation

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Solution Overview

Problem

Existing methods fail to effectively reduce the concentration of 3-MCPD fatty acid esters in highly enriched alkyl esters of polyunsaturated fatty acids (PUFAs), which are used in food products, supplements, and cosmetics, due to the formation of 3-MCPD during refining processes like distillation and chromatography, despite the known carcinogenicity of 3-MCPD and regulatory concerns.

Innovation Solution

The concentration of trace metals, particularly iron, is adjusted to less than 0.20 ppm in the starting material, and the content of monoacylglycerol (MAG) with C14 or C16 fatty acids is reduced, ensuring that the formation of 3-MCPD fatty acid esters is minimized during distillation, thereby producing PUFA or PUFA alkyl esters with low 3-MCPD concentrations.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Manufacturing precision

If distillation and chromatography are used to enrich PUFAs, then the proportion of desired PUFA increases, but 3-MCPD fatty acid esters form during the process

Engineering Contradiction:
ImprovePUFA enrichmentVSAvoid3-MCPD formation
Core Design Contradiction:
Manufacturing precisionVSObject-generated harmful factors

Solution Approach 1:

The patent applies preliminary action by removing MAG and DAG substrates and controlling trace metal content before the distillation process begins. This prevents the formation of 3-MCPD fatty acid esters during subsequent heating by eliminating the necessary components (MAG/DAG substrates and metal catalysts) required for the harmful reaction to occur.

Inventive Principle:
Principle #10Preliminary action

Solution Approach 2:

The patent employs parameter changes by strictly controlling the concentration of trace metals (particularly iron) to less than 0.20 ppm and limiting MAG/DAG content. These parameter changes prevent the catalytic formation of 3-MCPD while allowing the distillation process to proceed for PUFA enrichment.

Inventive Principle:
Principle #35Parameter changes

2Object-generated harmful factors

If complete removal of MAG and DAG is performed to prevent 3-MCPD formation, then 3-MCPD concentrations decrease, but productivity and PUFA recovery are negatively affected

Engineering Contradiction:
Improve3-MCPD concentrationVSAvoidPUFA recovery
Core Design Contradiction:
Object-generated harmful factorsVSProductivity

Solution Approach 1:

The patent applies parameter changes by establishing specific threshold values for MAG/DAG content and trace metal concentrations that balance 3-MCPD prevention with productivity maintenance. Rather than complete removal, the patent controls these parameters within ranges that prevent harmful formation while preserving necessary substrates for PUFA production.

Inventive Principle:
Principle #35Parameter changes

3Manufacturing precision

If rectification is used to achieve high separation performance, then PUFA enrichment improves, but heating temperatures exceed 150°C which promotes 3-MCPD formation

Engineering Contradiction:
Improveseparation performanceVSAvoidheating temperature
Core Design Contradiction:
Manufacturing precisionVSTemperature

Solution Approach 1:

The patent applies preliminary action by controlling trace metal content and MAG/DAG levels before distillation, which prevents 3-MCPD formation even when higher temperatures are used during rectification for improved separation performance.

Inventive Principle:
Principle #10Preliminary action

Solution Approach 2:

The patent employs parameter changes by controlling trace metal concentrations to less than 0.20 ppm, which allows the system to tolerate higher heating temperatures during rectification without promoting 3-MCPD formation, thus achieving both good separation and low 3-MCPD levels.

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

Compositions with high PUFA content and low 3-MCPD concentrations are produced consistently, meeting regulatory standards and ensuring safety for use in food, supplements, and cosmetics.

Implementation Method 1

distilling the composition obtained after step (2) and collecting a main distillate fraction

Methodology Applied
Scientific EffectDistillation: Distillation

Implementation Method 2

refining steps such as solvent removal and distillation that include a heating procedure

Methodology Applied
Scientific EffectHeating: Heating

Data Source

PatentEP4049537B1A composition containing highly unsaturated fatty acid or alkyl ester thereof
Publication Date: 2026.03.18 NISSUI CORPORATION
  • EP4049537B1 patent drawing
  • EP4049537B1 patent drawing
  • EP4049537B1 patent drawing

AI summary

The disclosure aims to provide compositions comprising highly enriched PUFA or alkyl ester thereof while containing fatty acid esters of 3-MCPD at adequately low concentrations and to provide an efficient method for producing the composition. The proposed composition contains fatty acids or fatty acid alkyl esters as its major component, the composition containing highly unsaturated fatty acid or alkyl ester thereof, wherein the proportion of the highly unsaturated fatty acid in the constituent fatty acids of the composition is 50 area% or more and wherein the concentration of 3-MCPD, as found by analysing the composition using American Oil Chemists' Society official method Cd 29b-13 assay A, is less than 1.80 ppm.