Mannich Condensation Sequestering Agents for Fuel and Oil

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Solution Overview

Problem

Conventional oil-soluble Mannich condensation products have limited ability to sequester Fe3+ ions and prevent Fe3+ catalyzed oxidation and polymerization in lubricating oils, and existing sequestering agents are not suitable for use in non-aqueous systems like fuels and lubricating oils.

Innovation Solution

A Mannich condensation product is formed by combining a polyisobutyl-substituted hydroxyaromatic compound, an aldehyde, an amino acid or ester, and an alkali metal base, which effectively sequesters metal ions such as Fe3+ and prevents oxidation and polymerization reactions in hydrocarbon media.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If conventional oil-soluble Mannich condensation products are used, then oil solubility is maintained, but the ability to sequester Fe3+ ions is limited

Engineering Contradiction:
Improvesequestering abilityVSAvoidmolecular structure complexity
Core Design Contradiction:
ReliabilityVSDevice complexity

Solution Approach 1:

The patent creates a composite molecular structure combining polyisobutyl-substituted hydroxyaromatic compounds (providing oil solubility) with amino acid-containing Mannich bases (providing Fe3+ sequestering ability). This composite approach integrates two functional systems into one molecule, simultaneously achieving oil solubility and enhanced metal ion sequestering capability.

Inventive Principle:
Principle #40Composite materials

Solution Approach 2:

The invention modifies the molecular parameters of conventional Mannich condensation products by incorporating amino acid residues with specific functional groups (carboxyl, amino, hydroxyl). These parameter changes in molecular structure enable stronger coordination with Fe3+ ions while maintaining compatibility with oil-based lubricating systems.

Inventive Principle:
Principle #35Parameter changes

2Reliability

If water soluble Mannich condensation products are used, then Fe3+ sequestering ability is improved, but suitability for non-aqueous systems is lost

Engineering Contradiction:
Improvesequestering abilityVSAvoidapplicability to non-aqueous systems
Core Design Contradiction:
ReliabilityVSAdaptability or versatility

Solution Approach 1:

The patent applies local quality by incorporating hydrophobic polyisobutyl substituents at specific positions on the aromatic ring system. These localized hydrophobic regions provide oil solubility while the rest of the molecule (amino acid-containing Mannich base portion) retains the hydrophilic functional groups necessary for Fe3+ coordination. This spatial differentiation of properties enables dual functionality.

Inventive Principle:
Principle #3Local quality

Solution Approach 2:

The polyisobutyl-substituted hydroxyaromatic compound acts as an intermediary bridge between the hydrophilic amino acid-Mannich base sequestering moiety and the hydrophobic oil medium. It mediates the interaction by providing oil solubility while allowing the sequestering functional groups to remain accessible for metal ion binding in the non-aqueous environment.

Inventive Principle:
Principle #24Intermediary (Mediator)

3Reliability

If metal ions are present in lubricating oils, then catalytic activity is enhanced, but oxidation and polymerization increase

Engineering Contradiction:
Improvecatalytic activityVSAvoidoxidation and polymerization
Core Design Contradiction:
ReliabilityVSObject-generated harmful factors

Solution Approach 1:

The patent converts the harmful catalytic effect of metal ions into a beneficial effect by sequestering them in a controlled manner. The Mannich condensation products bind metal ions through coordination chemistry, forming stable complexes that prevent the ions from catalyzing unwanted oxidation and polymerization reactions. The metal ions are not removed but their harmful activity is neutralized through beneficial complexation.

Inventive Principle:
Principle #22Blessing in disguise (Convert harm into benefit)

Solution Approach 2:

The invention applies preliminary anti-action by proactively sequestering metal ions before they can initiate or accelerate degradation reactions. The sequestering agents are present in the lubricating oil from the beginning, continuously binding metal ions and preventing them from acting as catalysts for oxidation and polymerization, thereby preventing harm before it occurs.

Inventive Principle:
Principle #9Preliminary anti-action

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 resulting Mannich condensation product maintains oil solubility and effectively sequesters metal ions, preventing metal ion catalyzed oxidation and polymerization reactions, making it suitable for use in lubricating oils and fuels.

Implementation Method 1

it would be desirable to find a way to complex or sequester the metal ions and prevent the metal ions from acting as oxidation and polymerization catalysts

Methodology Applied
Scientific EffectComplexation/Chelation: Chemical Bonding

Data Source

PatentEP1712605B1Mannich condensation products useful as sequestering agents
Publication Date: 2010.11.17 CHEVRON ORONITE CO LLC
  • EP1712605B1 patent drawing
  • EP1712605B1 patent drawing
  • EP1712605B1 patent drawing

AI summary

The present invention is directed to Mannich condensation product sequestering agents or mixtures of Mannich condensation product sequestering agents for use in fuels and lubricating oils. The present invention is also directed to a process for preparing the Mannich condensation product sequestering agents. The present invention is also directed to a product formed by combining, under reaction conditions, a polyisobutyl-substituted hydroxyaromatic compound, an aldehyde, an amino acid or ester thereof, and an alkali metal base to form the Mannich condensation product sequestering agent. The present invention is also directed to a lubricating oil composition, a lubricating oil concentrate, a fuel composition, and a fuel concentrate having the Mannich condensation product sequestering agents of the present invention.