Epoxidized Fatty Acid Ester Transesterification via Phase Separation

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Solution Overview

Problem

The production of epoxidized fatty acid esters from epoxidized soybean oil requires high molar excesses of methanol due to the absence of phase separation in the transesterification process, leading to inefficiencies and increased costs, whereas starting from unepoxidized soybean oil and then epoxidizing the ester results in higher methanol requirements and different phase behavior.

Innovation Solution

A process involving determining the moisture content of epoxidized natural fats or oils, selecting low moisture samples, and performing transesterification with an alcohol in the presence of a catalyst, allowing phase separation into an epoxidized fatty acid ester phase and a glycerol phase, thereby reducing the need for excessive methanol and improving reaction efficiency.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Productivity

If transesterification is performed on epoxidized soybean oil, then epoxidized fatty acid esters are produced, but high molar excesses of methanol are required due to absence of phase separation

Engineering Contradiction:
Improveproduction efficiencyVSAvoidmethanol consumption
Core Design Contradiction:
ProductivityVSQuantity of substance

Solution Approach 1:

The patent applies parameter changes by controlling moisture content at specific levels (0.01-0.1% in epoxidized oil, 2500ppm or less in alcohol) to enable phase separation. This parameter control transforms the reaction system from a single-phase to a two-phase system, allowing complete conversion with stoichiometric or near-stoichiometric methanol amounts rather than high molar excesses.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention exploits phase transitions by creating conditions where the transesterification products separate into distinct phases (epoxidized fatty acid ester phase and glycerol phase). This phase separation is achieved through precise moisture control and enables efficient product recovery without requiring large excesses of methanol, directly resolving the contradiction between productivity and methanol consumption.

Inventive Principle:
Principle #36Phase transitions

2Ease of manufacture

If unepoxidized soybean oil is used and epoxidized after esterification, then epoxidized esters are produced, but even higher methanol requirements and different phase behavior occur

Engineering Contradiction:
Improveprocess flexibilityVSAvoidmethanol consumption
Core Design Contradiction:
Ease of manufactureVSQuantity of substance

Solution Approach 1:

The patent applies preliminary action by performing epoxidation before transesterification rather than after esterification. This sequence allows the epoxidized oil to undergo controlled transesterification with phase separation, achieving complete conversion with lower methanol requirements. The preliminary epoxidation step creates a substrate that enables the subsequent phase separation phenomenon.

Inventive Principle:
Principle #10Preliminary action

3Reliability

If high molar excesses of methanol are used to achieve complete conversion, then conversion is complete, but reaction efficiency decreases and costs increase

Engineering Contradiction:
Improveconversion completenessVSAvoidreaction efficiency
Core Design Contradiction:
ReliabilityVSProductivity

Solution Approach 1:

The invention implements feedback control through monitoring and controlling moisture content at specific thresholds throughout the process. By maintaining moisture at 0.01-0.1% in the epoxidized oil and 2500ppm or less in the alcohol, the system ensures phase separation occurs, which in turn ensures complete conversion without requiring high methanol excesses. This feedback control achieves both complete conversion and high efficiency.

Inventive Principle:
Principle #23Feedback

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 process achieves complete conversion of epoxidized fatty acid esters with reduced methanol usage, phase separation, and improved product recovery, addressing the inefficiencies and costs associated with previous methods.

Implementation Method 1

carrying out a transesterification of the selected low moisture epoxidized natural fat or oil with an alcohol in the presence of a transesterification catalyst

Methodology Applied
Scientific EffectCatalysis: Catalysis

Implementation Method 2

allowing the products of the transesterification reaction to phase-separate into a byproduct glycerol-containing phase and epoxidized fatty acid ester-containing phase

Methodology Applied
Scientific EffectPhase separation: Phase Change

Data Source

PatentEP2768818B1Making epoxidized esters from epoxidized natural fats and oils
Publication Date: 2018.12.19 ARCHER DANIELS MIDLAND CO

AI summary

Processes are described for making epoxidized fatty acid esters from epoxidized natural fats and oils, wherein low moisture fats and oils are identified and selected or made and used in a transesterification process. The products undergo phase separation, and reduced molar excesses of alcohol may be employed compared to processes not employing a low moisture feedstock.