Bio-Based Cationic Surfactant Ether Linkage Stability

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Solution Overview

Problem

Cationic surfactants used in oil and gas applications face chemical instability due to high pressure, temperature, and pH extremes, and are not biodegradable, posing environmental concerns.

Innovation Solution

A cationic surfactant is developed using a lipophilic bio-based material with an epoxy functional group, forming a stable ether linkage and incorporating a readily biodegradable organic acid as a counter-ion to enhance biodegradability and chemical stability.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If an ester bond is used to connect the quaternary ammonium functional group to the hydrocarbon backbone, then biodegradability is improved, but chemical stability under high pressure, temperature, and pH extremes deteriorates

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

Solution Approach 1:

The patent changes the chemical bond type from ester to ether linkage, fundamentally altering the molecular structure's stability characteristics. The ether bond provides resistance to hydrolysis and chemical degradation under extreme conditions while maintaining biodegradability through the bio-based hydrocarbon backbone

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The surfactant combines a bio-based hydrocarbon backbone with an ether linkage and quaternary ammonium head group, creating a composite molecular structure that integrates the chemical stability of ether bonds with the biodegradability of natural oil derivatives

Inventive Principle:
Principle #40Composite materials

2Stability of the object's composition

If a stable ether linkage is used to connect the quaternary ammonium functional group to the hydrocarbon backbone, then chemical stability is improved, but biodegradability deteriorates

Engineering Contradiction:
Improvechemical stabilityVSAvoidbiodegradability
Core Design Contradiction:
Stability of the object's compositionVSReliability

Solution Approach 1:

The patent modifies the molecular structure by using ether linkages instead of ester bonds, changing the chemical stability parameter while maintaining biodegradability through the bio-based origin of the hydrocarbon backbone

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The ether linkage acts as an intermediary bond that connects the stable hydrocarbon backbone to the functional head group, providing chemical stability while allowing the overall molecule to remain biodegradable due to its bio-based composition

Inventive Principle:
Principle #24Intermediary (Mediator)

3Productivity

If conventional cationic surfactants are used, then oil recovery performance is improved, but environmental impact deteriorates due to toxicity and resistance to biodegradation

Engineering Contradiction:
Improveoil recoveryVSAvoidenvironmental impact
Core Design Contradiction:
ProductivityVSObject-generated harmful factors

Solution Approach 1:

The patent changes the molecular structure from conventional petroleum-based cationic surfactants to bio-based surfactants with ether linkages, altering the biodegradability parameter while maintaining surfactant functionality for oil recovery applications

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The bio-based cationic surfactant is designed to be biodegradable, allowing it to break down naturally after performing its oil recovery function, thus eliminating persistent environmental contamination while maintaining operational effectiveness

Inventive Principle:
Principle #34Discarding and recovering

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 surfactant maintains stability in harsh oilfield conditions, promotes biodegradation, and reduces environmental impact while improving oil recovery and rock-fluid behavior, offering a cost-effective and eco-friendly solution for oilfield applications.

Implementation Method 1

The reaction between the epoxy functional group and the hydroxyl functional group connects the lipophilic bio-based material to the hydrophilic organic compound via an ether linkage

Methodology Applied
Scientific EffectEther linkage formation: Chemical Bonding

Implementation Method 2

The cationic surfactant has been found to alter the rock-fluid behavior of the reservoir favorably towards improving oil recovery

Methodology Applied
Scientific EffectSurfactant action: Surfactant

Data Source

PatentUS11724981B2Cationic surfactants comprising an ether link
Publication Date: 2023.08.15 BATTELLE MEMORIAL INST
  • US11724981B2 patent drawing

AI summary

A cationic surfactant and a method of making the cationic surfactant are described. The method comprises reacting a lipophilic bio-based material having at least one epoxy functional group and a hydrophilic organic compound having at least one cationic functional group and at least one hydroxyl functional group to form a reaction product containing a stable ether linkage connecting the lipophilic bio-based material to the organic compound. At least a portion of the cationic functional groups is neutralized or ion exchanged with an organic acid. Incorporation of the simple organic acid reduces the surfactant's aquatic toxicity and acts as a substrate to encourage co-digestion of the surfactant molecule, making the compound more biodegradable.