Protected Aldehydes for Thermal Stability in Oilfield Fluids

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Solution Overview

Problem

Existing antimicrobial compounds used in oil and gas operations, such as formaldehyde, glutaraldehyde, and glyoxal, are prone to degradation at elevated temperatures and inactivation by common oilfield chemicals, leading to microbial fouling and corrosion issues.

Innovation Solution

Development of protected antimicrobial compounds that release formaldehyde, glyoxal, or glutaraldehyde when heat-activated, providing improved thermal and chemical stability, represented by specific chemical formulas and structures, which are more resistant to degradation by bisulfites and amines.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If conventional antimicrobial compounds (formaldehyde, glutaraldehyde, glyoxal) are used, then antimicrobial activity is achieved, but thermal stability deteriorates at elevated temperatures

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

Solution Approach 1:

The patent applies preliminary action by pre-protecting the aldehyde group with a hydroxylamine derivative to form a stable adduct before the antimicrobial compound is needed. This protected form is thermally stable and can be stored and transported safely. When applied to the aqueous system, heat activates the adduct to release the active aldehyde in situ, providing both thermal stability during storage and antimicrobial activity during use.

Inventive Principle:
Principle #10Preliminary action

2Reliability

If conventional antimicrobial compounds are used, then antimicrobial efficacy is achieved, but chemical stability deteriorates in the presence of oilfield chemicals

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

Solution Approach 1:

The patent uses a hydroxylamine derivative as an intermediary protective group that mediates between the unstable active aldehyde and the deactivating oilfield chemicals. The hydroxylamine adduct acts as a stable intermediate form that resists inactivation by bisulfites and amines. Upon thermal activation, this intermediary releases the active aldehyde that then exerts antimicrobial activity, thus protecting the active compound from chemical degradation.

Inventive Principle:
Principle #24Intermediary (Mediator)

3Stability of the object's composition

If protected antimicrobial compounds are used, then thermal stability is improved, but device complexity increases

Engineering Contradiction:
Improvethermal stabilityVSAvoidcompound structure complexity
Core Design Contradiction:
Stability of the object's compositionVSDevice complexity

Solution Approach 1:

The patent applies parameter changes by modifying the chemical structure of simple aldehydes through addition of hydroxylamine derivatives. This structural modification changes the thermal stability parameter of the compound without fundamentally altering the core aldehyde functionality. The protected adduct maintains the essential reactive characteristics while adding thermal stability, and the activation process simply requires thermal energy input to reverse the protection.

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

These compounds effectively control microorganisms for extended periods in aqueous systems at elevated temperatures, maintaining stability and efficacy even in the presence of deactivating agents, thus preventing microbial fouling in oil and gas operations and other industrial applications.

Implementation Method 1

protected antimicrobial compounds that release formaldehyde, glyoxal, or glutaraldehyde when heat-activated

Methodology Applied
Scientific EffectHeat activation: Thermal Energy Storage

Data Source

PatentUS9226499B2Protected antimicrobial compounds for high temperature applications
Publication Date: 2016.01.05 NUTRITION & BIOSCIENCES USA 1 LLC

AI summary

Provided are protected antimicrobial compounds which are useful for controlling microorganisms in aqueous or water-containing systems, such as oil or gas field fluids, at elevated temperature. The antimicrobial compounds are of the formula I:wherein R3 and R4 are as defined herein.