Fluorinated Chemical Marker for Petroleum Hydrocarbon Authentication

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Solution Overview

Problem

Current chemical markers for petroleum hydrocarbons face challenges such as light and heat instability, insolubility, toxicity, unsatisfactory counterfeit-resilience, and lengthy detection and quantification methods, limiting their effectiveness in preventing counterfeiting and ensuring authenticity.

Innovation Solution

A composition of petroleum hydrocarbon marked with a chemical marker of general formula (I), where two residues are C1-C4-alkoxy and eight residues are hydrogen or C1-C4-alkyl, allowing for easy detection, identification, and quantification using laser ionization coupled with mass spectrometry or ion mobility spectrometry.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Measurement precision

If gas chromatography is used for detection and quantification of chemical markers, then detection capability is achieved, but the GC column requires frequent replacement due to high amount of petroleum hydrocarbon components

Engineering Contradiction:
Improvedetection capabilityVSAvoidcolumn replacement frequency
Core Design Contradiction:
Measurement precisionVSLoss of time

Solution Approach 1:

The patent extracts only the essential detection function from the complex GC system by using selective laser ionization that directly ionizes the chemical marker in the petroleum hydrocarbon sample without requiring separation through a GC column. This eliminates the column replacement issue while maintaining detection capability.

Inventive Principle:
Principle #2Taking out (Extraction)

Solution Approach 2:

The patent replaces the mechanical separation system (GC column) with a direct spectroscopic detection method (laser ionization). The mechanical complexity of column separation is substituted by optical detection that selectively ionizes the marker compound based on its molecular structure.

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

2Measurement precision

If gas chromatography - mass spectrometry is used for detection, then detection precision is improved, but the ionization source requires frequent cleaning and replacement

Engineering Contradiction:
Improvedetection precisionVSAvoidmaintenance complexity
Core Design Contradiction:
Measurement precisionVSEase of manufacture

Solution Approach 1:

The patent extracts only the essential ionization and detection function from the GC-MS system by using selective laser ionization in the ultraviolet range. This eliminates the complex mass spectrometer ionization source that requires frequent cleaning and replacement, while maintaining detection precision through wavelength-specific ionization.

Inventive Principle:
Principle #2Taking out (Extraction)

Solution Approach 2:

The patent replaces the complex MS ionization source with a simpler laser-based ionization system. The mechanical and thermal complexity of the MS ionization source is substituted by a non-contact optical ionization method that has no moving parts requiring maintenance.

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

3Reliability

If existing chemical markers are used, then marking function is achieved, but light and heat instability limits effectiveness

Engineering Contradiction:
Improvemarking functionVSAvoidlight and heat stability
Core Design Contradiction:
ReliabilityVSStability of the object's composition

Solution Approach 1:

The patent changes the chemical structure parameters of the marker compound by introducing fluorinated aromatic groups, which significantly improve light and heat stability compared to non-fluorinated markers. The fluorinated structure resists degradation under UV exposure and high temperature conditions.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent uses composite molecular structure combining fluorinated aromatic rings with specific functional groups to create a marker that is both stable under various conditions and detectable by laser ionization. The composite structure provides both stability and detection capability.

Inventive Principle:
Principle #40Composite materials

4Reliability

If existing chemical markers are used, then marking capability is achieved, but lengthy detection and quantification methods reduce efficiency

Engineering Contradiction:
Improvemarking capabilityVSAvoiddetection speed
Core Design Contradiction:
ReliabilityVSProductivity

Solution Approach 1:

The patent extracts only the essential detection function by using direct laser ionization that detects the chemical marker in seconds without requiring lengthy GC separation or MS analysis. This dramatically improves productivity while maintaining reliable detection.

Inventive Principle:
Principle #2Taking out (Extraction)

Solution Approach 2:

The patent replaces the lengthy mechanical separation process of GC with direct optical detection. The marker is ionized and detected in seconds by laser irradiation, eliminating the time-consuming separation and analysis steps of traditional GC-MS methods.

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

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 enables the detection and quantification of minute quantities of the chemical marker, ensuring the authenticity of petroleum hydrocarbons and preventing adulteration, while being cost-effective, non-toxic, and resistant to laundering.

Implementation Method 1

laser ionization at a wavelength of between about 300 nm and about 370 nm coupled with mass spectrometry

Methodology Applied
Scientific EffectLaser ionization: Photoionisation

Data Source

PatentEP4069806B1Method of marking a petroleum hydrocarbon
Publication Date: 2025.04.16 SICPA HOLDING SA
  • EP4069806B1 patent drawingFigure 1a~1b
  • EP4069806B1 patent drawingFigure 1c~1d
  • EP4069806B1 patent drawingFigure 2a~2b

AI summary

The present invention relates to a method of marking a petroleum hydrocarbon by adding to and uniformly mixing with said petroleum hydrocarbon a chemical marker of general formula (I) wherein two of the residues R1 – R10 are independently of each other selected from C1-C4-alkoxy, and eight of the residues R1 – R10 are independently of each other selected from the group consisting of hydrogen and C1-C4-alkyl, as well as to a composition of a petroleum hydrocarbon comprising a petroleum hydrocarbon and at least one chemical marker of general formula (I). The presence and concentration of the chemical marker of general formula (I) in the composition of the petroleum hydrocarbon can be advantageously determined by laser ionization coupled with mass spectrometry or by laser ionization coupled with ion mobility spectrometry.