Preconcentration of petroleum organic acids and ketones by two-stage chromatography using a modified adsorbent

Strel’nikova, E. B.; Stakhina, L. D.; Петренко, Т. В.

doi:10.1134/s1061934809010031

Cited by 5 publications

(6 citation statements)

References 4 publications

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“…Although present, the high carbon number, alkyl ketone fragments overlap with (and are thus partially masked by) the 13 C isotopologue ( m / z = 58) of abundant alkane fragments whose monoisotopic mass lies at m / z = 57. In contrast, a selected ion mass chromatogram for ions of m / z 58 (Figure , middle) reveals an easily identifiable homologous series of alkyl ketones ( n- alkane-2-ones) . The ions with n -alkane carbon numbers less than 15 are, however, most likely not native MWO n -alkanes, because they evaporate during weathering .…”

Section: Resultsmentioning

confidence: 99%

“…In contrast, a selected ion mass chromatogram for ions of m/z 58 (Figure 5, middle) reveals an easily identifiable homologous series of alkyl ketones (n-alkane-2-ones). 32 The ions with nalkane carbon numbers less than 15 are, however, most likely not native MWO n-alkanes, because they evaporate during weathering. 4 The second fraction is preferentially enriched in high carbon number ketones (C 19−23 most abundant) relative to the third fraction (Figure 5, bottom, in which C 7−12 ions are most abundant) due to their weaker interaction with the liquid chromatographic stationary phase (a result of their higher carbon number) and higher polarity of the eluting solvent.…”

Section: Energy and Fuelsmentioning

confidence: 99%

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Targeted Petroleomics: Analytical Investigation of Macondo Well Oil Oxidation Products from Pensacola Beach

et al. 2014

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Of the estimated 5 million barrels of crude oil released into the Gulf of Mexico from the Deepwater Horizon oil spill, a fraction washed ashore onto sandy beaches from Louisiana to the Florida panhandle. Here, we compare the detailed molecular analysis of hydrocarbons in oiled sands from Pensacola Beach to the Macondo wellhead oil (MWO) by electrospray (ESI) and atmospheric pressure photoionization (APPI) Fourier transform ion cyclotron resonance mass spectrometry (FT-ICR MS) to identify major environmental transformation products of polar, high molecular weight (C >25 ) "heavy ends" (high-boiling species) inaccessible by gas chromatography. The petrogenic material isolated from the Pensacola Beach sand displays greater than 2-fold higher molecular complexity than the MWO constituents, most notably in oxygenated species absent in the parent MWO. Surprisingly, the diverse oxygenated hydrocarbons in the Pensacola Beach sediment extracts were dominant in all ionization modes investigated, (±) ESI and (±) APPI. Thus, the molecular-level information highlighted oxygenated species for subsequent "targeted" analyses. First, time-of-flight mass spectrometry analysis of model compounds attributes the unusually large oxygen signal magnitude from positive electrospray to ketone transformation products (O 1 −O 8 classes). Next, negative electrospray mass spectrometry reveals carboxylic acid transformation products. Two-dimensional gas chromatography with mass spectrometry analysis of anion-exchange chromatographic fractions unequivocally verifies the presence of abundant alkyl ketone fragments in sand extracts, and FT-ICR MS analysis reveals the distribution of high-boiling ketone, carboxylic, and higher numbered (3+) oxygen-containing transformation products too polar to be analyzed by gas chromatography. The results expand compositional coverage of oxygen-containing functionalities beyond the classic naphthenic acid type species to complex/mixed ketone, hydroxyl, and carboxylic acid classes of molecules that have been recently identified in produced water, emulsions, and petroleum production deposits.

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Section: Resultsmentioning

confidence: 99%

Section: Energy and Fuelsmentioning

confidence: 99%

Targeted Petroleomics: Analytical Investigation of Macondo Well Oil Oxidation Products from Pensacola Beach

et al. 2014

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“…Thin-layer chromatography , also had such a problem. The most commonly used method for separating ketones was liquid chromatography, which had a wide range of applications and was used in Colorado shale oil, West Siberian oil, − coal extract, and the Lake Holzmaar sediment extract . A solid-phase extraction (SPE) was specialized in the fractionation of ketones according to functional groups and applied to Irati oil shale .…”

Section: Introductionmentioning

confidence: 99%

Separation and Molecular Characterization of Ketones in a Low-Temperature Coal Tar

et al. 2018

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Ketones are major oxygen-containing compounds in low-temperature coal tars (LTCTs); however, the molecular composition of these compounds is not well characterized as a result of the complexity of itself and the interference of the coal tar matrix. In this study, ketones were separated from a LTCT and characterized by Fourier transform ion cyclotron resonance mass spectrometry (FT-ICR MS), Orbitrap mass spectrometry (Orbitrap MS), and gas chromatography–mass spectrometry (GC–MS). Isolation of ketones was carried out by a chemical derivatization process with Girard T reagent and followed by a hydrolysis process of the derivatives. The Girard T reagent reacted with ketones under weakly acidic conditions and introduced a charged quaternary ammonium moiety on carbonyl to form water-soluble hydrazones, which can be separated from a complex matrix through an extrography separation and have a strong response in a positive-ion electrospray ionization (ESI) source for mass spectrometric analysis. The isolated derivatives were reversibly turned into the original ketones to selectively separate long alkyl ketones from aromatic ketones with alkyl substituents of C0–C4. The ketones were assigned to 12 class species by high-resolution MS analysis: O1–5 (refers that there are 1–5 oxygen atoms in the molecules), O1S1, N1O1–4, and N2O1–2, among which the O1 class species was the most abundant. The long-chain alkyl ketones, such as aliphatic 2-, 3-, and 4-ketones, alkylcyclopentanones, alkyl phenyl ketones, and aromatic ketones (such as indanone, cyclopentenone, tetralone, acetonaphthone, dihydrophenanthrenone, benzophenone, fluorenone, fluorenyl formaldehyde, anthrone, anthracene formaldehyde, acetylanthracene, acetylphenanthrene, acetylfluorene, benzofluorenone, etc.), were detected by GC–MS. In addition, C18-isoprenoid methyl ketone and tricyclic terpenoids and steroids with one or two oxygen atoms were found in the coal tar.

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“…For molecular characterization, ketones from fossil fuels were generally separated by solid-phase extraction (SPE), extrography, liquid chromatography, and thin-layer chromatography . Some ketones have been identified using gas chromatography (GC) and/or gas chromatography–mass spectrometry (GC–MS). ,− ,− However, these methods do not sufficiently isolate ketones from hydrocarbons, nitriles, phenols, and other compounds to enable a definitive identification.…”

Section: Introductionmentioning

confidence: 99%

“…For molecular characterization, ketones from fossil fuels were generally separated by solid-phase extraction (SPE), 14 extrography, 15 liquid chromatography, 16 and thin-layer chro-matography. 17 Some ketones have been identified using gas chromatography (GC) and/or gas chromatography−mass spectrometry (GC−MS).…”

Section: Introductionmentioning

confidence: 99%

Molecular Characterization of Ketones in a Petroleum Source Rock

et al. 2018

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A comprehensive investigation of oil composition is important for the petroleum industry as well as the understanding of natural science. Ketones commonly exist in petroleum; however, as a result of the low concentrations and limitations inherent in the analytical technique, the molecular composition of these compounds is rarely studied. In this study, ketones in a source rock were characterized by gas chromatography–mass spectrometry, Fourier transform ion cyclotron resonance mass spectrometry, and Orbitrap mass spectrometry. Ketones were derivatized with the Girard T reagent under weakly acidic conditions to enhance their detectability by electrospray ionization mass spectrometry (ESI MS) analysis. Atmospheric pressure photoionization mass spectrometry (APPI MS) was also used for the molecular characterization of ketones without chemical derivatization. The characterization techniques were complementary to each other, and the results were consistent in general. The chemical derivatization followed by positive-ion ESI MS analysis is suitable for the analysis of ketones in a trace amount, but it had discrimination on high double bond equivalent (DBE) species (DBE ≥ 9). Direct analysis with positive-ion APPI MS showed comparable ionization efficiency throughout the DBE range and could distinguish aliphatic ketones from aromatic ketones according to different ionization pathways.

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Preconcentration of petroleum organic acids and ketones by two-stage chromatography using a modified adsorbent

Cited by 5 publications

References 4 publications

Targeted Petroleomics: Analytical Investigation of Macondo Well Oil Oxidation Products from Pensacola Beach

Targeted Petroleomics: Analytical Investigation of Macondo Well Oil Oxidation Products from Pensacola Beach

Separation and Molecular Characterization of Ketones in a Low-Temperature Coal Tar

Molecular Characterization of Ketones in a Petroleum Source Rock

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