Halogenated Fluorescent Tracers for Fuel Authentication

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Solution Overview

Problem

Existing methods for marking hydrocarbon liquids, such as gasoline and diesel fuels, face challenges in tracer stability and resistance to removal through evaporation, degradation, and deliberate removal techniques like adsorption or chemical treatments, which compromises their effectiveness in ensuring fuel authenticity and tax compliance.

Innovation Solution

The use of tracer compounds with a specific formula, including bromine, fluorine, and halogenated alkyl groups, which exhibit distinct fluorescent properties and are resistant to removal methods like adsorption on charcoal or clay and chemical treatments, ensuring long-term stability and detectability in hydrocarbon fuels.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If conventional tracer compounds are used to mark hydrocarbon fuels, then the fuels can be identified and tracked in the supply chain, but the tracers can be removed through evaporation, degradation, adsorption, or chemical treatments

Engineering Contradiction:
Improvetracer stabilityVSAvoidtracer removal
Core Design Contradiction:
ReliabilityVSLoss of substance

Solution Approach 1:

The patent modifies the chemical structure of tracer compounds by incorporating specific functional groups (bromoalkyl, fluoroalkyl, aryl) and molecular weight ranges (250-500 g/mol) to enhance resistance against removal mechanisms while maintaining detectability. This structural parameter optimization directly addresses the contradiction between tracer stability and resistance to removal.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention uses composite tracer molecules combining multiple functional groups (e.g., BODIPY core with halogenated alkyl chains and aromatic substituents) to achieve both stability against degradation and resistance to adsorption. The composite structure integrates properties that simultaneously improve reliability and prevent loss through various removal mechanisms.

Inventive Principle:
Principle #40Composite materials

2Reliability

If tracer compounds are made resistant to removal methods, then their stability improves, but their detectability and identification capability must be maintained

Engineering Contradiction:
Improvetracer stabilityVSAvoidtracer detection
Core Design Contradiction:
ReliabilityVSDifficulty of detecting and measuring

Solution Approach 1:

The patent employs fluorescent tracer compounds with specific emission wavelengths that provide distinct optical signatures for detection. The fluorescent property allows easy identification using portable instrumentation while the molecular structure ensures resistance to removal, resolving the contradiction between stability and detectability.

Inventive Principle:
Principle #32Color changes

Solution Approach 2:

The invention replaces complex chemical analysis methods with simpler fluorescent detection using portable instrumentation. This substitution makes detection easier while the tracer's inherent fluorescent property maintains detectability even as structural modifications enhance stability.

Inventive Principle:
Principle #28Mechanics substitution (Replace mechanical system)

3Reliability

If tracer compounds are added to detect fuel adulteration and tax evasion, then fuel authenticity can be verified, but the tracers may degrade through exposure to environmental conditions such as heat, sunlight, or air

Engineering Contradiction:
Improvefuel authenticationVSAvoidtracer lifespan
Core Design Contradiction:
ReliabilityVSDuration of action of stationary object

Solution Approach 1:

The patent optimizes tracer molecular weight (250-500 g/mol) and incorporates stable functional groups (halogenated alkyl chains, aromatic rings) to enhance resistance against environmental degradation from heat, sunlight, and air exposure. These parameter changes extend tracer lifespan while maintaining authentication reliability.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention uses chemically stable tracer compounds with inert characteristic groups (fluorinated and brominated alkyl chains) that resist oxidation and degradation in exposure to air and environmental conditions, effectively creating an inert chemical environment within the tracer structure itself.

Inventive Principle:
Principle #39Inert atmosphere (Inert environment)

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 proposed solution provides a stable and detectable tracer that maintains its presence in hydrocarbon fuels, even under harsh conditions, allowing for effective identification and prevention of fuel adulteration and tax evasion, with compounds like difluoroborondipyrromethene derivatives showing high retention rates during laundering tests.

Implementation Method 1

Molecules exhibiting a characteristic fluorescent response that is at a different wavelength from that of the bulk medium are particularly suited for use as tracer molecules

Methodology Applied
Scientific EffectFluorescence: Fluorescence

Data Source

PatentEP2788459B1Tracers and method of marking hydrocarbon liquids
Publication Date: 2020.06.03 JOHNSON MATTHEY PLC
  • EP2788459B1 patent drawing
  • EP2788459B1 patent drawing
  • EP2788459B1 patent drawing

AI summary

The invention concerns a method of marking a hydrocarbon liquid comprising the step of adding to said liquid, as a tracer compound, a compound of Formula I: wherein, each X is independently selected from the group consisting of a hydrogen atom, a bromine atom, a fluorine atom, a partially or fully halogenated alkyl group, a linear, branched or cyclic C1 –C20 alkyl group and a phenyl group substituted with one or more halogen atoms, an alkyl group or a halogenated alkyl group; each Y is independently selected from the group consisting of a bromine atom, a fluorine atom, a partially or fully halogenated alkyl group, a branched or cyclic C1–C9 alkyl group and a phenyl group substituted with at least one alkyl group and/or a halogenated alkyl group; Z is selected from the group consisting of (i) a phenyl group substituted with one or more halogen atoms, an aliphatic group or a halogenated aliphatic group, (ii) a partially or fully halogenated alkyl group or (iii) a linear, branched or cyclic C1–C20 alkyl group with the proviso that when each Y is a fluorine atom, Z is not a linear or branched C1-C20 alkyl group..