Ester Polyol Transesterification to Lower Crystallization Temperature

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Solution Overview

Problem

Current methods for preparing ester polyols often result in products with high crystallization temperatures and phase separation issues, particularly when using feedstocks with high saturated fatty acids, making them difficult to process into useful products like polyurethane foams and lubricants.

Innovation Solution

A method involving the transesterification of a first ester polyol with a primary polyol to produce a second ester polyol with a higher hydroxyl value, using sequential steps such as reacting a fatty acid distillate with ozone and refluxing, and incorporating branched primary polyols to inhibit crystallization and improve properties like viscosity and molecular weight.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Productivity

If ester polyols are prepared from feedstocks with high amounts of saturated fatty acids, then the ester polyol production is feasible, but the crystallization temperature becomes relatively high causing phase separation

Engineering Contradiction:
Improveester polyol productionVSAvoidphase separation
Core Design Contradiction:
ProductivityVSStability of the object's composition

Solution Approach 1:

The patent changes the chemical composition parameters of the ester polyol by using unsaturated fatty acids (oleic acid) instead of saturated fatty acids, and by controlling the hydroxyl value through selective esterification. This parameter change prevents phase separation while maintaining production feasibility.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent applies local quality modification by selectively esterifying specific hydroxyl groups of the polyol with unsaturated fatty acids, creating regions of high hydroxyl value that prevent crystallization and phase separation while maintaining overall product viability.

Inventive Principle:
Principle #3Local quality

2Adaptability or versatility

If the hydroxyl value of the ester polyol is increased, then the utility and reactivity are improved, but the crystallization temperature increases making processing difficult

Engineering Contradiction:
ImproveutilityVSAvoidcrystallization temperature
Core Design Contradiction:
Adaptability or versatilityVSTemperature

Solution Approach 1:

The patent achieves high hydroxyl value (greater than 300) while preventing crystallization by changing the fatty acid composition to unsaturated types and controlling the esterification process, thereby decoupling the relationship between hydroxyl value and crystallization temperature.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent creates a composite ester polyol structure combining polyol backbone with unsaturated fatty acid ester groups, where the specific combination of components achieves both high hydroxyl value and low crystallization temperature through synergistic effects.

Inventive Principle:
Principle #40Composite materials

3Ease of manufacture

If conventional esterification methods are used, then the process is simple, but the product requires extensive purification and has poor performance in applications

Engineering Contradiction:
Improveprocess simplicityVSAvoidproduct performance
Core Design Contradiction:
Ease of manufactureVSReliability

Solution Approach 1:

The patent modifies the esterification process by using unsaturated fatty acids and controlling reaction conditions to achieve high hydroxyl value products with improved performance, eliminating the need for extensive purification while enhancing reliability.

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

The method produces ester polyols with improved physical properties, such as reduced crystallization temperatures and inhibited phase separation, leading to enhanced performance in applications like polyurethane foams and lubricants, with increased hydroxyl values and tailored specifications for different end-use applications.

Implementation Method 1

reacting a fatty acid distillate with ozone in the presence of a reactant and a catalyst to produce a reaction mixture, wherein the ozone comprises at least two moles of ozone per carbon-to-carbon double bond of the fatty acid distillate

Methodology Applied
Scientific EffectOzonolysis: Ozone

Implementation Method 2

refluxing the reaction mixture to produce the first ester polyol having a hydroxyl value (HV i )

Methodology Applied
Scientific EffectReflexing: Heating

Implementation Method 3

transesterifying a first ester polyol with a primary polyol to produce a second ester polyol, the second ester polyol having a hydroxyl value (HV) which is greater than a hydroxyl value (HV i ) of the first ester polyol

Methodology Applied
Scientific EffectTransesterification: Chemical Bonding

Data Source

PatentEP2819990B1Method for producing an esterified polyol
Publication Date: 2019.03.27 PETROLIAM NASIONAL BHD
  • EP2819990B1 patent drawingFigure 1
  • EP2819990B1 patent drawingFigure 2
  • EP2819990B1 patent drawingFigure 3

AI summary

A method for producing an ester polyol, comprising transesterifying a first ester polyol with a primary polyol to produce a second ester polyol, wherein the second ester polyol has a higher hydroxyl value than the first ester polyol.