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 and glutaraldehyde, are susceptible to degradation at elevated temperatures and inactivation by common oilfield chemicals, leading to microbial fouling issues.

Innovation Solution

Development of protected antimicrobial compounds that release formaldehyde or glutaraldehyde upon heat activation, providing enhanced 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) are used, then microbial growth control is achieved, but thermal stability deteriorates at elevated temperatures

Engineering Contradiction:
Improvemicrobial growth controlVSAvoidthermal stability
Core Design Contradiction:
ReliabilityVSStability of the object's composition

Solution Approach 1:

The patent applies preliminary action by pre-protecting the aldehyde compound with a protective group before use. The protected compound is formulated in advance with the protective group intact, which prevents thermal degradation during storage and handling. Upon application to the aqueous system, the protective group is removed (either spontaneously or through hydrolysis), releasing the active aldehyde compound that then controls microbial growth. This preliminary protection resolves the contradiction by ensuring thermal stability during storage while maintaining antimicrobial efficacy when needed.

Inventive Principle:
Principle #10Preliminary action

Solution Approach 2:

The protective group acts as an intermediary between the unstable aldehyde compound and the harsh thermal environment. This intermediary compound (the protected form) is thermally stable and can be stored and handled safely. It mediates the delivery of the active aldehyde to the aqueous system without undergoing thermal degradation, thus resolving the contradiction between needing thermal stability for storage and requiring antimicrobial activity for growth control.

Inventive Principle:
Principle #24Intermediary (Mediator)

2Reliability

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

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

Solution Approach 1:

The protective group is applied in advance to shield the aldehyde compound from chemical inactivation by oilfield chemicals such as bisulfites and amines. This preliminary protection prevents unwanted reactions between the active compound and deactivating agents in the oilfield environment, ensuring the compound remains stable until it reaches the target aqueous system where microbial control is needed.

Inventive Principle:
Principle #10Preliminary action

Solution Approach 2:

The protective group serves as a chemical intermediary that protects the vulnerable aldehyde functionality from reacting with bisulfites and amines. This intermediary structure is chemically inert toward these deactivating agents, allowing the compound to survive in oilfield chemical environments. Once in the target system, the protective group is removed to release the active aldehyde for microbial control.

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 the aldehyde compound through addition of a protective group. This structural modification changes the thermal and chemical stability parameters of the compound without fundamentally altering its core antimicrobial mechanism. The protective group is chosen to be simple and well-understood chemistry, minimizing the increase in complexity while achieving the desired stability improvement.

Inventive Principle:
Principle #35Parameter changes

4Duration of action of moving object

If protected antimicrobial compounds are used, then duration of action is extended, but manufacturing precision requirements increase

Engineering Contradiction:
Improveduration of antimicrobial actionVSAvoidsynthesis precision
Core Design Contradiction:
Duration of action of moving objectVSManufacturing precision

Solution Approach 1:

The protective group modification changes the stability parameters of the compound, enabling extended duration of action in thermal and chemically harsh environments. The extended stability allows the compound to remain effective for longer periods in oilfield applications. Regarding manufacturing precision, the patent likely employs standard protective group chemistry with well-established protocols, which minimizes the increase in synthesis complexity despite the extended duration of action achieved.

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 protected compounds effectively control microbial growth in aqueous systems at elevated temperatures for extended periods, 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 or glutaraldehyde upon heat activation

Methodology Applied
Scientific EffectHeat activation: Thermolysis

Data Source

PatentUS8741928B2Protected antimicrobial compounds for high temperature applications
Publication Date: 2014.06.03 NUTRITION & BIOSCIENCES USA 1 LLC
  • US8741928B2 patent drawing
  • US8741928B2 patent drawing
  • US8741928B2 patent drawing

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 R, R1, R2, X and Y are as defined herein.