Enzymic Transesterification for OPO Production

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Solution Overview

Problem

Current processes for producing 1,3-dioleoyl-2-palmitoyl glyceride (OPO) are inefficient, and there is a need for a more effective method to match the chemical and physical properties of human milk fat, particularly in infant formulas, as existing methods struggle with achieving the optimal distribution of fatty acid residues in triglycerides.

Innovation Solution

A process involving enzymic transesterification of palm oil stearin with an iodine value between 8 and 12 using oleic acid or its ester, followed by separation and dry fractionation to increase the OPO content, while minimizing other triglycerides like PPP and OOO, and maximizing palmitic acid residues in the 2-position.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Productivity

If conventional enzymatic processes are used to produce OPO, then some OPO is formed, but the process is inefficient and fails to achieve optimal distribution of fatty acid residues

Engineering Contradiction:
ImproveOPO production efficiencyVSAvoidfatty acid residue distribution control
Core Design Contradiction:
ProductivityVSManufacturing precision

Solution Approach 1:

The process uses a two-stage enzymatic approach: first a 1,3-specific lipase creates ABA triglycerides with palmitic acid at positions 1 and 3, then a 1,2,3-specific lipase converts these to OPO by replacing the fatty acids at positions 1 and 3 with oleic acid. This segmentation of the conversion process into distinct stages with different enzyme specificities enables efficient OPO production with controlled fatty acid distribution.

Inventive Principle:
Principle #1Segmentation

Solution Approach 2:

Instead of directly converting PPP to OPO in a single step, the process inverts the approach by first creating an intermediate ABA structure and then converting to OPO. This indirect route through ABA triglycerides as an intermediate allows better control over the final OPO formation and improves overall process efficiency.

Inventive Principle:
Principle #13The other way round (Inversion)

2Quantity of substance

If vegetable oils are used to create fat compositions with similar fatty acid amounts to human milk fat, then the fatty acid composition matches, but the glyceride position distribution remains unsaturated at the 2-position unlike human milk fat

Engineering Contradiction:
Improvefatty acid composition matchVSAvoidglyceride position distribution
Core Design Contradiction:
Quantity of substanceVSManufacturing precision

Solution Approach 1:

The process specifically targets the 2-position of the glyceride backbone to ensure palmitic acid occupies this position, while allowing unsaturated fatty acids at positions 1 and 3. The enzymatic reactions are designed with position-specific selectivity: the 1,3-specific lipase acts only on positions 1 and 3, while the 1,2,3-specific lipase subsequently modifies all three positions, ensuring palmitic acid is concentrated at the 2-position to match human milk fat structure.

Inventive Principle:
Principle #3Local quality

3Manufacturing precision

If multiple enzymatic conversion steps are used to reduce trisaturates, then OPO purity improves, but the process complexity and time increase

Engineering Contradiction:
ImproveOPO purityVSAvoidprocess steps
Core Design Contradiction:
Manufacturing precisionVSDevice complexity

Solution Approach 1:

The process employs continuous enzymatic action through sequentially added enzymes that work in a coordinated manner. The 1,3-specific lipase continuously produces ABA intermediates, which are then continuously converted by the 1,2,3-specific lipase to OPO. This continuous multi-enzyme action achieves high OPO purity and reduces trisaturates effectively while maintaining process efficiency.

Inventive Principle:
Principle #20Continuity of useful action

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

The process significantly increases the OPO content in the product, enhancing the nutritional quality and matching the fatty acid distribution of human milk fat, with the OPO composition achieving a higher SN-2 value, thereby improving the digestibility and emulsification properties of the resulting fat composition.

Implementation Method 1

subjecting a palm oil stearin, with an iodine value (IV) between 8 and 12 to enzymic transesterification, with oleic acid or a non-glyceride ester thereof

Methodology Applied
Scientific EffectEnzymic transesterification: Enzyme

Data Source

PatentEP1928990B1Process for producing dioleyl palmitoyl glyceride
Publication Date: 2017.02.15 BUNGE LODERS CROKLAAN BV
  • EP1928990B1 patent drawing
  • EP1928990B1 patent drawing
  • EP1928990B1 patent drawing

AI summary

A process for the production of a composition comprising l,3-dioleyl-2-palmitoyl glyceride (OPO) comprises subjecting a palm oil stearin, with an iodine value (IV) between about 2 and about 12 to enzymic transesterification, with oleic acid or a non-glyceride ester thereof.