Aminophenol Antioxidant Composition for Biodiesel Oxidation Stability

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Solution Overview

Problem

Biodiesel and biolubricants face challenges in maintaining oxidation stability due to the removal of natural antioxidants during manufacturing, leading to issues like sedimentation, gum formation, and corrosion in engines, with conventional antioxidants often requiring high concentrations and being incompatible with bio-based fuels or causing environmental concerns.

Innovation Solution

The use of oxygenated aminophenol antioxidants, specifically compounds of Formula I, which are compatible with bio-based fuels and lubricants, effectively inhibiting oxidation without compromising combustion, lubricity, or flow properties, even at low temperatures, and reducing sedimentation and corrosion in engines.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If conventional antioxidants are used to inhibit oxidation of biodiesel and biolubricants, then oxidation stability is improved, but the antioxidants are incompatible with bio-based fuels or require high concentrations that compromise combustion, lubricity, or flow properties

Engineering Contradiction:
Improveoxidation stabilityVSAvoidcompatibility with bio-based fuels
Core Design Contradiction:
ReliabilityVSAdaptability or versatility

Solution Approach 1:

The patent applies parameter changes by modifying the chemical structure of phenolic antioxidants through N-alkylation with glycidyl ethers, transforming conventional antioxidants into amino phenolic antioxidants with improved compatibility. This structural modification changes the chemical parameters of the antioxidant molecule, enabling it to function effectively in biodiesel and biolubricant systems without compromising combustion, lubricity, or flow properties while maintaining oxidation stability enhancement

Inventive Principle:
Principle #35Parameter changes

2Reliability

If conventional antioxidants are used at elevated concentrations to control oxidation, then oxidation stability is improved, but combustion, lubricity, and flow properties are compromised

Engineering Contradiction:
Improveoxidation stabilityVSAvoidcombustion efficiency
Core Design Contradiction:
ReliabilityVSProductivity

Solution Approach 1:

The patent uses parameter changes by altering the chemical structure of the antioxidant through N-alkylation, which enables the amino phenolic antioxidant to achieve effective oxidation protection at lower concentrations. This structural modification changes the effectiveness parameter of the antioxidant, allowing it to protect biodiesel and biolubricants from oxidation while maintaining combustion efficiency and avoiding the need for high concentrations that would compromise productivity

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent creates a composite antioxidant structure by combining phenolic groups with N-alkylated glycidyl ether groups, forming an amino phenolic antioxidant with dual functionality. This composite molecular structure integrates the oxidation protection capability of phenolic groups with the compatibility and performance-enhancing properties of N-alkylated side chains, enabling effective antioxidant activity at low concentrations without compromising combustion properties

Inventive Principle:
Principle #40Composite materials

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 oxygenated aminophenol antioxidants significantly prolong the induction time in oxidation stability tests, outperforming comparative antioxidants, and provide improved oxidation stability, reducing sedimentation and corrosion in biodiesel engines, while maintaining the properties of biodiesel and biolubricants.

Implementation Method 1

inhibit oxidation of oxidizable compounds in natural oils or materials made therefrom, such as fuel and lubricant compositions like biodiesel and biolubricants

Methodology Applied
Scientific EffectOxidation: Oxidation

Implementation Method 2

These radicals promote free-radical chain reactions that cause the formation of oxidized chemical compounds of low molecular weight, like acids, aldehydes, and ketones

Methodology Applied
Scientific EffectFree-radical chain reactions:

Data Source

PatentUS20240215601A1Compositions and methods for inhibiting oxidation of natural oil based composition using aminophenol antioxidant
Publication Date: 2024.07.04 ECOLAB USA INC
  • US20240215601A1 patent drawing
  • US20240215601A1 patent drawing
  • US20240215601A1 patent drawing

AI summary

Compositions including a vegetable- or animal-derived oil, such as fatty acid alkyl esters, are stabilized against oxidation using an oxygenated aminophenol antioxidant. The aminophenol includes one or two carbon-containing group(s) including a hydroxyl group and/or ether group separated from the N atom by one or more carbon atoms. The oxygenated aminophenol antioxidants effective at controlling oxidation at moderate and even low amounts, useful in a variety of different oil and methyl ester fatty acid preparations, and were effective at elevated temperatures, and performed significantly better than convention antioxidants.