Diaryl Ether Fuel Markers for Enhanced Coding Capacity

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Solution Overview

Problem

There is a need for additional marker compounds to enhance the digital marking systems for liquid hydrocarbons and other fuels, as existing markers limit the available codes and do not maximize the identification capabilities of these products.

Innovation Solution

The method involves adding specific compounds of formula (I) and (II) to petroleum hydrocarbons or biologically derived fuels, which are detectable through chromatographic techniques and mass spectral analysis, allowing for the creation of unique codes based on their ratios and identities.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Adaptability or versatility

If existing marker compounds are used for marking fuels, then the marking function is achieved, but the coding capacity and identification capabilities are limited

Engineering Contradiction:
Improvecoding capacityVSAvoidavailable marker compounds
Core Design Contradiction:
Adaptability or versatilityVSQuantity of substance

Solution Approach 1:

The patent applies parameter changes by systematically varying the R1 substituent parameters in the diaryl ether marker compounds. Different alkyl groups (methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl) and their positional isomers are used to create distinct marker compounds with identical core structures but different physical and spectral parameters, thereby expanding coding capacity without requiring entirely new compound classes

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent segments the marker compound system into a standardized core structure (diaryl ether with alkoxy substitution) and variable substituent parameters. This segmentation allows for systematic generation of multiple markers by changing only the R1 groups while maintaining the detectable core structure, enabling expanded coding capacity through controlled variation of specific molecular parameters

Inventive Principle:
Principle #1Segmentation

2Adaptability or versatility

If additional marker compounds are introduced to expand coding capacity, then the identification capabilities are enhanced, but the complexity of the marking system increases

Engineering Contradiction:
Improveidentification capabilitiesVSAvoidmarking system complexity
Core Design Contradiction:
Adaptability or versatilityVSDevice complexity

Solution Approach 1:

The patent achieves universality by designing all marker compounds around a common detectable core structure (substituted diphenyl ether). This universal core ensures that all markers can be detected by the same analytical methods (GC-MS, LC-MS, NMR, UV-Vis) and can be processed through the same identification system, thereby enhancing identification capabilities without proportionally increasing system complexity

Inventive Principle:
Principle #6Universality (Multi-functionality)

Solution Approach 2:

The patent uses controlled parameter changes in the R1 substituents to generate marker diversity while maintaining structural regularity. The systematic variation of alkyl chain lengths and positions provides sufficient differentiation for coding purposes without introducing excessive structural complexity that would complicate detection and analysis

Inventive Principle:
Principle #35Parameter changes

3Loss of information

If marker compounds are added to fuels, then the identification function is achieved, but the fuel properties may be affected

Engineering Contradiction:
Improvefuel origin informationVSAvoidfuel property stability
Core Design Contradiction:
Loss of informationVSReliability

Solution Approach 1:

The patent applies local quality by introducing marker compounds at very low concentrations (ppm to ppb levels) that are sufficient for detection and identification purposes but too low to significantly affect bulk fuel properties. The markers are localized in terms of both concentration and functional role, allowing the fuel to maintain its primary combustion function while carrying identification information

Inventive Principle:
Principle #3Local quality

Solution Approach 2:

The patent carefully controls the concentration parameter of marker compounds to ensure it is sufficient for reliable detection by analytical instruments but remains below thresholds that would affect fuel combustion characteristics, stability, or performance. This parameter optimization maintains fuel reliability while achieving effective marking

Inventive Principle:
Principle #35Parameter changes

4Measurement precision

If detectable marker compounds are used, then the identification function is achieved, but the markers may be visually detectable which is undesirable

Engineering Contradiction:
Improvemarker detectabilityVSAvoidvisual detectability
Core Design Contradiction:
Measurement precisionVSObject-affected harmful factors

Solution Approach 1:

The patent replaces visual/mechanical detection with instrumental analytical detection methods. The marker compounds are designed to be detected by sophisticated analytical instruments (GC-MS, LC-MS, NMR, UV-Vis spectroscopy) rather than human visual inspection, thereby achieving high measurement precision for identification while eliminating the harmful effect of visual detectability that would compromise fuel aesthetics and user acceptance

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

This approach provides additional markers that can be used to identify the origin and characteristics of fuels, enhancing the coding capacity and detectability of the marked products without affecting their properties or being visually detectable.

Implementation Method 1

detectable through chromatographic techniques and mass spectral analysis

Methodology Applied
Scientific EffectChromatography: Chromatography

Implementation Method 2

detectable through chromatographic techniques and mass spectral analysis

Methodology Applied
Scientific EffectMass spectrometry:

Data Source

PatentEP3775111B1Diaryl ethers as fuel markers
Publication Date: 2024.03.20 DOW GLOBAL TECHNOLOGIES LLC
  • EP3775111B1 patent drawing
  • EP3775111B1 patent drawing
  • EP3775111B1 patent drawing

AI summary

A method for marking a petroleum hydrocarbon or a liquid biologically derived fuel; said method comprising adding to said petroleum hydrocarbon or liquid biologically derived fuel at least one compound that is a R1, R2, R3, R4, R5, R6, R7, R8, R9 and R10 -substituted diaryl ether, wherein R1, R2, R3, R4, R5, R6, R7, R8, R9 and R10 independently are hydrogen, hydrocarbyl or hydrocarbyloxy; wherein each compound having formula (I) is present at a level from 0.01 ppm to 20 ppm.