Ester Compounds for Lubricants Resisting Hydrolysis

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Solution Overview

Problem

Conventional lubricants are not hydrolysis-stable and degrade at high temperatures, leading to loss of lubricating effect, increased maintenance, and environmental contamination, while existing estolides have low resistance to hydrolysis and viscosity index.

Innovation Solution

Development of new ester compounds using di-, tri-, and higher functional carboxylic acids with specific radical structures, synthesized through methods A, B, and C, which involve reaction with unsaturated fatty acids and alcohols, providing high yield, selectivity, and ease of purification.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If conventional ester compounds are used in lubricants, then the lubricant can be produced with basic lubricating properties, but the ester splits into fatty acid and alcohol in the presence of water leading to destruction of molecules and loss of lubricating effect

Engineering Contradiction:
Improvehydrolysis stabilityVSAvoidmolecular stability
Core Design Contradiction:
ReliabilityVSStability of the object's composition

Solution Approach 1:

The patent changes the chemical structure parameters of the ester compounds by using higher functionality carboxylic acids (with functionality of at least 2.5) instead of conventional esters. This structural modification creates estolides with multiple ester groups per molecule, which significantly improves hydrolysis stability while maintaining lubricating properties. The specific parameter change involves selecting carboxylic acids with functionality ≥2.5, which fundamentally alters the molecular stability under hydrolytic conditions.

Inventive Principle:
Principle #35Parameter changes

2Temperature

If conventional lubricants are used in high-temperature applications, then the lubricant can operate at elevated temperatures, but the lubricant is destroyed by oxidation and thermal decomposition leading to loss of lubricating effectiveness

Engineering Contradiction:
Improveoperating temperatureVSAvoidthermal stability
Core Design Contradiction:
TemperatureVSReliability

Solution Approach 1:

The patent creates composite molecular structures by combining higher functionality carboxylic acids with specific alcohols to form estolide molecules. These composite structures incorporate multiple functional groups and complex molecular architectures that provide both high-temperature stability and effective lubrication. The composite nature of the estolide molecules allows them to resist oxidation and thermal decomposition while maintaining lubricating film formation at elevated temperatures.

Inventive Principle:
Principle #40Composite materials

3Productivity

If conventional lubricants are used in high-temperature applications, then the lubricant can provide initial lubrication, but decomposition leads to formation of low-molecular-weight volatile components causing viscosity changes and oil loss

Engineering Contradiction:
Improvecontinuous operation capabilityVSAvoidlubricant loss
Core Design Contradiction:
ProductivityVSLoss of substance

Solution Approach 1:

The patent changes the molecular weight and structural complexity parameters by using higher functionality carboxylic acids to create high molecular weight estolide compounds. These modified parameters result in lubricants with significantly reduced volatility and evaporation rates at high temperatures. The increased molecular complexity and weight prevent decomposition into low-molecular-weight volatile components, thereby maintaining constant viscosity and preventing oil loss during continuous high-temperature operation.

Inventive Principle:
Principle #35Parameter changes

4Productivity

If conventional lubricants are used in high-temperature applications, then the lubricant can provide initial lubrication, but polymerization occurs leading to formation of insoluble products and increased maintenance work

Engineering Contradiction:
Improvecontinuous operation capabilityVSAvoidmaintenance work
Core Design Contradiction:
ProductivityVSEase of repair

Solution Approach 1:

The patent modifies the chemical structure parameters by introducing higher functionality carboxylic acids with specific molecular characteristics that prevent uncontrolled polymerization. The resulting estolides have controlled molecular architectures with functionality ≥2.5 that resist forming insoluble polymerization products. This parameter modification eliminates the need for complex disposal procedures and reduces maintenance work, allowing continuous operation without contamination issues.

Inventive Principle:
Principle #35Parameter changes

5Ease of manufacture

If estolides with only di- and higher carboxylic acids as linkers are used, then the lubricant can be produced with basic properties, but the lubricant exhibits low hydrolysis resistance and low viscosity index

Engineering Contradiction:
Improveproduction simplicityVSAvoidhydrolysis resistance
Core Design Contradiction:
Ease of manufactureVSReliability

Solution Approach 1:

The patent specifically changes the functionality parameter of the carboxylic acid component to be at least 2.5, which is higher than conventional estolides that use only difunctional acids. This parameter change in the molecular structure directly improves hydrolysis resistance while maintaining production simplicity. The higher functionality creates a more stable molecular network that resists hydrolytic cleavage, solving the contradiction between ease of manufacture and hydrolysis resistance.

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 new ester compounds exhibit improved hydrolysis stability, high temperature resistance, and biodegradability, suitable for use in lubricants for high-temperature applications and food-compatible environments, reducing maintenance and environmental impact.

Implementation Method 1

the ester is split into the fatty acid and the alcohol when the lubricant is used in the presence of water. This reaction can be catalyzed by acids, bases, or copper, for example.

Methodology Applied
Scientific EffectHydrolysis: Hydrolysis

Implementation Method 2

they can be destroyed at high temperatures by oxidation and/or thermal decomposition processes

Methodology Applied
Scientific EffectOxidation: Oxidation

Implementation Method 3

they can be destroyed at high temperatures by oxidation and/or thermal decomposition processes

Methodology Applied
Scientific EffectThermal decomposition: Pyrolysis

Implementation Method 4

The evaporation of these volatile components leads to undesirable changes in viscosity, oil loss, and excessive vapor formation.

Methodology Applied
Scientific EffectEvaporation: Evaporation

Data Source

PatentEP3601209B1Novel ester compounds, method for the production thereof and use thereof
Publication Date: 2024.11.27
  • EP3601209B1 patent drawing
  • EP3601209B1 patent drawing
  • EP3601209B1 patent drawing

AI summary

The invention relates to novel ester compounds based on bi-, tri- or higher functional carboxylic acids of general formula (I) and to a method for the production thereof and the use thereof in lubricants.