Epoxidized Mono-Esters for PVC Plasticizers

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Solution Overview

Problem

Bio-based plasticizers, such as epoxidized soybean oil, face challenges with limited compatibility and exudation issues when used in halogenated polymers like PVC, leading to brittleness and reduced flexibility in final products.

Innovation Solution

A process involving the epoxidation of vegetable oils followed by transesterification and short-path distillation to produce epoxidized mono-esters with reduced non-functionalized fatty acid esters, enhancing compatibility and reducing exudation, is developed.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If epoxidized vegetable oil is used as a plasticizer in PVC, then the plasticizer provides flexibility and is bio-based, but it exhibits limited compatibility and causes exudation leading to brittleness

Engineering Contradiction:
Improvecompatibility with PVCVSAvoidexudation
Core Design Contradiction:
ReliabilityVSObject-generated harmful factors

Solution Approach 1:

The invention changes the chemical composition parameters of the plasticizer by removing non-functionalized fatty acid esters through distillation, thereby improving compatibility with PVC and reducing exudation while maintaining the bio-based nature and flexibility-providing properties of the epoxidized vegetable oil

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention extracts and removes the harmful non-functionalized fatty acid esters from the epoxidized vegetable oil through distillation, separating the beneficial epoxidized mono-esters from the harmful components that cause exudation and brittleness

Inventive Principle:
Principle #2Taking out (Extraction)

2Manufacturing precision

If conventional distillation is used to purify epoxidized vegetable oil, then purification is achieved, but thermal degradation occurs due to high temperatures

Engineering Contradiction:
Improvepurification levelVSAvoidthermal degradation
Core Design Contradiction:
Manufacturing precisionVSObject-affected harmful factors

Solution Approach 1:

The invention utilizes vacuum distillation which lowers the boiling point of the plasticizer components, allowing purification through phase transition at reduced temperatures that prevent thermal degradation while achieving the required purification level

Inventive Principle:
Principle #36Phase transitions

Solution Approach 2:

The invention employs nitrogen atmosphere during distillation to create an inert environment that prevents oxidation and thermal degradation of the epoxidized vegetable oil components while still achieving effective purification

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

The process results in bio-based plasticizers with improved compatibility and reduced exudation, suitable for use in halogenated polymers, maintaining flexibility and preventing brittleness in PVC applications.

Implementation Method 1

The invention refers to a process for the production of bio-based compounds that can be used as plasticizer in halogenated polymers comprising epoxidized mono-esters

Methodology Applied
Scientific EffectEpoxidation: Oxidation

Implementation Method 2

The invention also refers to a process for preparing two mixtures of epoxidized fatty acid (mono-)esters, comprising in the order given: 1) epoxidation of a vegetable oil, followed by 2) transesterification of the epoxidized vegetable oil

Methodology Applied
Scientific EffectTransesterification: Chemical Bonding

Implementation Method 3

followed by 3) short path distillation of the transesterified epoxidized vegetable oil

Methodology Applied
Scientific EffectDistillation: Distillation

Implementation Method 4

selection of the non-vaporized fraction of process step 3) as the first mixture of epoxidized fatty acid esters and 5) selection of the vaporized fraction of process step 3) as the second mixture of epoxidized fatty acid esters

Methodology Applied
Scientific EffectVaporization: Evaporation

Data Source

PatentEP3687984B1Process for preparing mixtures of epoxidized fatty acid esters
Publication Date: 2021.07.21 PROVIRON HLDG
  • EP3687984B1 patent drawingFigure 1
  • EP3687984B1 patent drawing
  • EP3687984B1 patent drawing

AI summary

The present invention relates to a process for preparing two mixtures of epoxidized fatty acid esters, comprising in the order given a transesterification of an epoxidized vegetable oil, followed by a reduction of the volatile saturated non-epoxidized fraction by short path distillation of the transesterified epoxidized vegetable oil, followed by a selection on the one hand of the non-vaporized fraction (residue) of the previous process step as the first mixture of epoxidized fatty acid esters and a selection on the other hand of the vaporized fraction (distillate) as the second mixture of epoxidized fatty acid esters. The first mixture is in particular suitable as plasticizer in halogenated polymers, the second mixture being particularly suitable as plasticizer in non- halogenated polymers.