Distribution of Oxygen-Containing Compounds and Its Significance on Total Organic Acid Content in Crude Oils by ESI Negative Ion FT-ICR MS

Rojas-Ruiz, Fernando A.; Orrego-Ruiz, Jorge A.

doi:10.1021/acs.energyfuels.6b01597

Cited by 27 publications

(24 citation statements)

References 38 publications

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“…O'Reilly () discussed the need to consider the presence of both degradation intermediates and material synthesized from bacterial growth. The terms “oxygen‐containing compounds” (Rojas‐Ruiz and Orrego‐Ruiz ) and “oxygen‐containing organic compounds” (OCOCs; Eigenmann et al ) have been used in the scientific literature to describe the types of chemicals that are the focus of this research. In this manuscript, we use the term “OCOCs,” as it describes their chemistry without making assumptions about their biological source.…”

Section: Introductionmentioning

confidence: 99%

Oxygen‐Containing Compounds Identified in Groundwater from Fuel Release Sites Using GCxGC‐TOF‐MS

O’Reilly

Mohler

Zemo³

et al. 2019

Groundwater Monitoring Rem

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This research continues a 7‐year study of oxygen‐containing organic compounds present in groundwater at gasoline and diesel fuel release sites that are quantified as diesel‐range “total petroleum hydrocarbons” when measured by methods utilizing solvent extraction and gas chromatography. Two‐dimensional gas chromatography with time‐of‐flight mass spectrometry was used to tentatively identify 1162 compounds (TICs) in 113 groundwater samples from 22 sites. Samples were collected from wells either upgradient of the release, within the source zone, or downgradient of the source but still within the plume of dissolved organics associated with release. The names and formulas of all TICs found in samples from each well type are presented and the results from upgradient and downgradient locations are compared in detail. About 60% of the most frequently detected TICs in downgradient wells were also detected in upgradient wells. A majority of these were saturated straight chain alkyl acids, commonly called fatty acids, or fatty acid esters. Of TICs frequently detected in downgradient wells but not upgradient wells, over half were branched alkyl alcohols. Hierarchical cluster analysis results suggest about 80% of the chemical composition of downgradient samples is more similar to upgradient samples than to source area samples. This similarity is due to the presence of the same types of fatty acids and esters. Principal component analysis indicates a continuum of biodegradation between the source area and downgradient samples with the latter becoming more consistent with upgradient samples. Results suggest some TICs may not be petroleum degradation intermediates but compounds synthesized by microorganisms through secondary production and carbon cycling.

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Section: Introductionmentioning

confidence: 99%

Oxygen‐Containing Compounds Identified in Groundwater from Fuel Release Sites Using GCxGC‐TOF‐MS

O’Reilly

Mohler

Zemo³

et al. 2019

Groundwater Monitoring Rem

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“…The O 2 species with a DBE of 6 were likely a phenol core fused with a furan core. Furthermore, Orrego-Ruiz and Rojas-Ruiz 50 concluded that the O 2 compounds found in the acidic fraction are confined to DBE <10, while the nonacids to DBE >10. The relative abundance of O 3 class compounds with DBE values of 2, 9, 11, and 14 was higher than that of compounds with adjacent DBE values, as shown in Figure 13 .…”

Section: Results and Discussionmentioning

confidence: 99%

Pyrolysis Temperature Effect on Compositions of Neutral Nitrogen and Acidic Species in Shale Oil Using Negative-Ion ESI FT-ICR MS

et al. 2020

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Negative-ion electrospray ionization (ESI) Fourier-transform ion cyclotron resonance mass spectrometry (FT-ICR MS) was used to study the effect of the pyrolysis temperature (400, 430, 460, 490, and 520 °C) on acidic and neutral nitrogen species in Huadian shale oil. To more accurately analyze the influence, shale oils produced during the heat-up stage were abandoned. The results show that because of the influence of polymerization and cracking reactions, the increase in temperature increases the content of pyrrole, thiophene, furan, phenol, and aromatic ring cores and decreases the content of carboxylic acid, respectively. Among all the heteroatom compounds identified from negative-ion ESI FT-ICR MS, the relative abundance of N 1 O 1 , N 1 O 2 , N 1 O 3 , N 2 , N 2 O 1 , O 1 , O 3 , O 1 S 1 , and N 1 S 1 species increases, whereas that of O 2 and O 4 species decreases as the pyrolysis temperature increases. The decrease in the O 2 species can be attributed to carboxylic acid with a double-bond equivalence (DBE) value of 1, whereas the increase in the O 2 species with DBE values of 7 and 9 can be attributed to the formation of furan, phenol, and aromatic ring by the polymerization reaction at higher pyrolysis temperatures. Although the effect of the reaction temperature on the molecular composition of acidic and neutral nitrogen species is complex, still characteristic rules are found in this study.

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“…The compounds with DBE of 1 were the most abundant O2 species, accounting for 10%, which were likely to be fatty acids. 32 The O2 species with DBEs ≥2 were assigned to naphthenic/aromatic structures containing a carboxyl moiety. 33 For instance, the O2 species with a DBE range of 2–6 could be naphthenic acids containing one to five naphthenic rings.…”

Section: Resultsmentioning

confidence: 99%

Molecular Analyses of Petroleum Hydrocarbon Change and Transformation during Petroleum Weathering by Multiple Techniques

Wang

Zhang

et al. 2021

ACS Omega

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Various analytical techniques are used to study the weathering process of four crude oils, i.e., Iranian light crude oil, Daqing crude oil, Shengli crude oil, and Tahe crude oil. The molecular composition and structural information of n -alkanes, polycyclic aromatic hydrocarbons (PAHs), and heteroatom compounds were characterized by gas chromatography-flame ionization detector (GC-FID), gas chromatography-mass spectrometry (GC-MS), and Fourier transform ion cyclotron resonance mass spectrometry (FT-ICR MS), respectively. The results showed that the weathering loss of n -alkanes was related to the molecular weight, and the low-molecular-weight (LMW) n -alkanes were more volatile. The loss degree of LMW naphthalene and alkylation homologues in PAHs was also higher. With the increase in the alkylation degree, the weathering resistance ability of PAHs was enhanced. In the negative-ion ESI FT-ICR MS mode, a total of 16 classes of compounds were detected for neutral nitrogen compounds and acidic compounds in the four crude oils. With the increase in weathering time, the relative abundances of NO, NO2, and O3S compounds gradually increased. In particular, the NO and NO2 compounds with different condensation degrees increased significantly. These results indicated that in addition to the volatilization of hydrocarbon compounds, nitrogen compounds were also oxidized to a certain extent during the weathering process. The provided information would enrich the understanding of the short-term weathering process of petroleum hydrocarbons.

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Distribution of Oxygen-Containing Compounds and Its Significance on Total Organic Acid Content in Crude Oils by ESI Negative Ion FT-ICR MS

Cited by 27 publications

References 38 publications

Oxygen‐Containing Compounds Identified in Groundwater from Fuel Release Sites Using GCxGC‐TOF‐MS

Oxygen‐Containing Compounds Identified in Groundwater from Fuel Release Sites Using GCxGC‐TOF‐MS

Pyrolysis Temperature Effect on Compositions of Neutral Nitrogen and Acidic Species in Shale Oil Using Negative-Ion ESI FT-ICR MS

Molecular Analyses of Petroleum Hydrocarbon Change and Transformation during Petroleum Weathering by Multiple Techniques

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