Discovery and identification of a series of alkyl decalin isomers in petroleum geological samples

Wang, Huitong; Zhang, Shuichang; Weng, Na; Zhang, Bin; Zhu, Guangyou; Liu, Lingyan

doi:10.1039/c4an00815d

Cited by 7 publications

(4 citation statements)

References 24 publications

(39 reference statements)

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“…Up to 11% of the observed mass fraction of diesel fuel has also been attributed to bicyclic alkanes . In this study, we identify alkyl-decalins without the use of authentic standards owing to the characteristic mass spectra obtained for these compounds, with the presence of their corresponding molecular ion; the mass fragments of the respective observed isomers are in good agreement with the results published by Wang et al Alkyl-decalins were identified by their characteristic mass fragment m / z 137 together with the molecular ion (using 14 eV spectra). The two closely eluting peaks correspond to the alkyl chain at the 1- and 2- positions of the decahydronaphthalene structure but cannot be distinguished from one another.…”

Section: Resultssupporting

confidence: 89%

“…Avila et al utilized GC×GC-ToF-MS and EI coupled to Fourier transform cyclotron resonance mass spectrometry to analyze compounds found in heavy gas oils, tentatively identifying alkyl-decalins. More recently, however, Wang et al characterized these compounds by synthesizing and investigating their mass spectra using GC×GC-ToF-MS, reporting the mass spectra and retention times for decalins ranging from C 1 to C 11 in alkyl chain length. Worton et al reported that bicyclic alkanes with various branched alkyl chains contributed about 30% of the observed mass in POA and lubricating oil.…”

Section: Resultsmentioning

confidence: 99%

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Using Variable Ionization Energy Time-of-Flight Mass Spectrometry with Comprehensive GC×GC To Identify Isomeric Species

2016

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Although GC×GC-ToF-MS allows the separation of thousands of peaks, many of these peaks are not positively identified owing to the lack of mass spectral library data and/or standard materials, leading to a substantial amount of information being inaccessible. The fragmentation patterns of molecules in mass spectrometers using electron impact ionization at 70 eV can be useful for molecule identification, provided a match is available in a published EI MS library, but are indistinguishable for many isomeric organic compounds (for example, linear and branched alkanes). Lower ionization energies have been exploited leading to organic compounds being ionized with lower excess internal energy and less fragmentation, retaining the molecular ion and maximizing its relative signal. This has enabled the identification of a large number of isomeric organic compounds, both aliphatic and aromatic, between C12-C36, in the previously unresolved complex mixture (UCM) of two motor oil samples. This technique also demonstrates problems associated with separation of coeluting isomers, particularly for the n-alkanes, which are routinely measured by 1D GC/MS and may be overestimated, due to coelution. As a consequence retention times in 2 dimensions and mass spectra at variable ionization energies are shown to give unparalleled power to identify specific isomers.

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Section: Resultssupporting

confidence: 89%

Section: Resultsmentioning

confidence: 99%

Using Variable Ionization Energy Time-of-Flight Mass Spectrometry with Comprehensive GC×GC To Identify Isomeric Species

2016

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“…Furthermore, drilling fluids might be contaminated by the geogenic organic compounds due to their recycling process. For instance, 1,2,3,4-tetrahydronaphthalene, and naphthalene, decahydro-2-methyl- might be the natural PMT/vPvM substances from shale formation. , This suggests that the natural PMT/vPvM substances are also worth attention, besides the artificial PMT/vPvM substances. The detailed information on sources for these PMT/vPvM substances is presented in Supporting Information (Table S4).…”

Section: Resultsmentioning

confidence: 99%

Identifying Candidate Persistent, Mobile, and Toxic (PMT) and Very Persistent and Very Mobile (vPvM) Substances in Shale Gas Drilling Fluids by Combining Nontarget Analysis and Machine Learning Model

Wang,

Han,

Jin

2024

Environ. Sci. Technol. Lett.

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Shale gas extraction has raised environmental concerns on regional water resources. Horizontal drilling is a process in which drilling fluids containing complex organic and inorganic chemicals are intensively applied. Accidental spill and improper disposal of drilling fluids and related wastes might pose risks to surrounding groundwater environment. Given regional ground water quality, persistent, mobile, and toxic (PMT) and very persistent and very mobile (vPvM) substances should be of particular attention. However, recent research rarely focused on chemical compositions of drilling fluids, and the harmful PMT/ vPvM substances in drilling fluids remain unknown. In this study, we utilized a nontarget screening strategy to detect and identify the organic compounds in drilling fluids collected in southwest China. Specifically, a total number of 371 compounds were detected in drilling fluids, and the main fraction of the compounds was alicyclic compounds. Later, an original machine learning model developed by us was applied to identify the candidate PMT/vPvM substances among the detected organic compounds. Our study identified 29 candidate PMT/vPvM substances, thus providing a list of prioritized substances for early warning and risk assessment of regional groundwater contamination.

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“…Wang et al, 462 2015 Identification and validation of decahydronaphthalene isomers in crude oil and a source rock extract sample Zhang et al, 463 2015…”

Section: Advances In Analytical Tools For Complexmentioning

confidence: 99%

Analytics Driving Kinetics: Advanced Mass Spectrometric Characterization of Petroleum Products

et al. 2021

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The current state-of-the-art in analysis techniques for petroleum fractions has progressed substantially during the last decade. This has helped to further improve the lumping procedures and modeling approaches of these complex systems. Recent advances in gas chromatography (GC), GC-field ionization mass spectrometry (GC-FIMS), and comprehensive gas chromatography (GC × GC) have made it possible to determine the compositions of fractions with up to 45 carbon atoms and in some cases up to C80. The combination of MS techniques with other selective detectors and reversed-phase column combinations has made it possible to quantify even traces of heteroatomic compounds in these complex hydrocarbon matrices. Fourier transform ion cyclotron resonance mass spectrometry (FT-ICR-MS), in some cases combined with GC × GC for the lighter part, has pushed the characterization of larger macromolecules in particular asphaltenes. Matrix-assisted laser desorption/ionization (MALDI) is also used widely for this purpose but has the disadvantage that quantification is not obvious. The development of more detailed characterization techniques has not remained unnoticed in the petrochemical society, and more recently in the petrochemical kinetic modeling society. More detailed characterization of petrochemical fractions has made the implementation of detailed kinetic models for simulation and optimization possible including more and more molecular detail. Additionally, advances in photo-ionization mass spectrometry (PI-MS) have allowed the detection of reactive intermediates and direct kinetic measurements in time-resolved experiments. It can only be expected that this trend will continue and that the application field will move from now primarily petrochemistry, (from catalytic cracking, over hydrotreating and hydrocracking, to pyrolysis, combustion, and steam cracking) to larger-scale chemical recycling and biomass conversion processes.

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Discovery and identification of a series of alkyl decalin isomers in petroleum geological samples

Cited by 7 publications

References 24 publications

Using Variable Ionization Energy Time-of-Flight Mass Spectrometry with Comprehensive GC×GC To Identify Isomeric Species

Using Variable Ionization Energy Time-of-Flight Mass Spectrometry with Comprehensive GC×GC To Identify Isomeric Species

Identifying Candidate Persistent, Mobile, and Toxic (PMT) and Very Persistent and Very Mobile (vPvM) Substances in Shale Gas Drilling Fluids by Combining Nontarget Analysis and Machine Learning Model

Analytics Driving Kinetics: Advanced Mass Spectrometric Characterization of Petroleum Products

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