Halogenated Tracer Compounds for Fuel Marking
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Solution Overview
Problem
Existing methods for marking hydrocarbon liquids, such as fuels, are prone to tracer removal due to evaporation, degradation, and deliberate removal techniques like adsorption or chemical treatments, making it challenging to ensure traceability and authenticity.
Innovation Solution
The use of tracer compounds with specific structural features, such as bromine or fluorine atoms, branched alkyl groups, and phenyl groups, which are resistant to removal by common methods, including adsorption and chemical treatments, ensuring the tracer remains detectable in hydrocarbon liquids.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Reliability
If conventional tracer compounds are used for marking hydrocarbon liquids, then the marking function is achieved, but the tracer can be removed by evaporation, degradation, adsorption, or chemical treatments
Solution Approach 1:
The patent changes the chemical parameters of the tracer compound by introducing specific structural features: bromine or fluorine atoms (providing high electron affinity and chemical stability), branched alkyl groups (providing steric hindrance against metabolic degradation and adsorption), and phenyl groups (enhancing chemical stability). These parameter changes make the tracer resistant to removal by evaporation, degradation, adsorption, and chemical treatments while maintaining detectability
Solution Approach 2:
The tracer compound is designed as a composite molecular structure combining multiple functional groups: halogen atoms (bromine/fluorine), branched alkyl chains, and phenyl rings. This composite structure provides synergistic effects where each component contributes specific properties: halogen atoms resist chemical treatment, branched alkyl groups resist adsorption and degradation, and phenyl groups enhance overall stability, collectively achieving high resistance to all removal mechanisms
2Quantity of substance
If the tracer concentration is kept low for economic reasons, then cost is reduced, but detection becomes more difficult
Solution Approach 1:
The patent replaces conventional detection methods with mass spectrometry, which provides extremely high sensitivity and selectivity. This substitution enables detection of the tracer at very low concentrations (500 ppbv or less) because mass spectrometry can distinguish the tracer's unique mass-to-charge ratio signature even at trace levels, overcoming the detection difficulty that would normally accompany low concentrations
3Reliability
If the tracer structure is made more complex to improve resistance to removal, then removal resistance increases, but manufacturing complexity increases
Solution Approach 1:
The patent applies local quality by introducing specific functional groups (bromine/fluorine atoms, branched alkyl groups, phenyl groups) at strategic positions within the tracer molecule. Rather than making the entire molecule complex, these localized structural features provide the necessary resistance to removal mechanisms while keeping the rest of the molecular structure relatively simple and manufacturable
Data Source
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 or Formula II: wherein at least one of R1 - R6 in Formula I and at least one of R7 - R14 in Formula II is selected from: i. a bromine or fluorine atom; ii. a partially or fully halogenated alkyl group; iii. a branched or cyclic C4 - C20 alkyl group; iv. an aliphatic substituent linking two positions selected from R1 - R6 in Formula I to one another or two positions selected from R7-R14 in Formula II to one another; or v. a phenyl group substituted with a halogen atom, an aliphatic group or halogenated aliphatic group and none of R1 - R6 in Formula I and none of R7 - R14 in Formula II being a sulphonate group or COOR15, where R15 represents H, C1 - C20 alkyl, C2 - C20 alkenyl, C2- C20 alkynyl, C3 - C15 cycloalkyl or aryl.