Speciation of alkylated dibenzothiophenes through correlation of structure and gas chromatographic retention indexes

Schade, Thomas; Andersson, Jan T.

doi:10.1016/j.chroma.2006.03.079

Cited by 49 publications

(28 citation statements)

References 20 publications

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“…Although spectra for all isomers are not available, fragmentation patterns found in the literature (32,48,49), in the NIST database, and in Table 2 suggest substitution on both rings results in the (M-1) + ion as the dominant fragmentation product. In contrast, when two methyls are on the same ring, one •CH 3 cleaves and hydrogen shifts to produce the benzylium/tropylium cation at m/z 197 that has a much higher relative abundance than when the groups are on both rings, viz., 60% vs. 20% RA; see Figure 3 for illustration.…”

Section: Resultsmentioning

confidence: 95%

“…191 (64) 382 (40) 383 (35) 385 (32) 192 (22) 190 (19) 386 (92) 380 (7) 166 methyl from the ethyl side chain is also the base ion for the C 3 and C 4 homologs (32), and the benzylium/tropylium ion is created by cleavage of ethyl, propyl, and butyl groups on propyl, butyl, and pentyl dibenzothiophenes, respectively, as well (49). Since there are so few synthesized C 2 -C 4 alkylated PASH, work is in progress to detect these compounds in coal tar and crude oil by automated sequential GC-GC/MS.…”

Section: -Ring Pashsmentioning

confidence: 99%

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Mass Spectra and Retention Indexes for Polycyclic Aromatic Sulfur Heterocycles and Some Alkylated Analogs

Zeigler

Schantz

Wise

et al. 2012

Polycyclic Aromatic Compounds

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Polycyclic aromatic sulfur heterocycles (PASH) are ubiquitous in fossil fuels and pose risk to the environment due to their toxicity. Some PASH, resistant to degradation in the environment, are used to differentiate pollutant source and weathering. Although retention data exist for some PASH, few mass spectra are available, so misidentification often occurs between isomers in the same family. In this study, the retention behavior of 119 PASH on 14%-cyanopropyl/86%-polydimethylsiloxane (DB-1701ms), trifluoropropylmethylpolysiloxane (Rtx-200ms), 5%-phenyl/95%-dimethyl (Rxi-5ms), and 50%-diphenyl/50%-dimethyl (Rxi-17Sil-ms) are reported along with their mass spectra. This data is guiding on-going research aimed at identifying PASH in coal tar by multidimensional GC-GC/MS for compounds where standards are not available.

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Section: Resultsmentioning

confidence: 95%

Section: -Ring Pashsmentioning

confidence: 99%

Mass Spectra and Retention Indexes for Polycyclic Aromatic Sulfur Heterocycles and Some Alkylated Analogs

Zeigler

Schantz

Wise

et al. 2012

Polycyclic Aromatic Compounds

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“…Among these, gas chromatography (GC) with sulfur specific detectors is routinely applied [7,8]. Unfortunately, due to the limitation by analyte volatility, analysis by GC is restricted to the hydrocarbon fractions boiling below 370ºC.…”

Section: Introductionmentioning

confidence: 99%

Characterization of Nitrogen and Sulfur Compounds in Hydrocracking Feedstocks by Fourier Transform Ion Cyclotron Mass Spectrometry

Al-Hajji

Muller

Koseoglu

2008

Oil & Gas Science and Technology - Rev. IFP

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-Characterization of Nitrogen and Sulfur Compounds in Hydrocracking Feedstocks by Fourier Transform Ion Cyclotron Mass Spectrometry -Advanced characterization of two heavy hydrocracking unit feedstocks, Heavy Vacuum Gas Oil (HVGO) and De-Metallized Oil (DMO), both derived from Arabian Light crude oil, was performed using High Resolution Fourier Transform Ion Cyclotron Resonance Mass Spectrometry (FT-ICR MS) to gain in-depth information on their aromaticity characteristics and heteroatom content, i.e., sulfur-and nitrogen-compounds. In

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“…Gas chromatography (GC) has been the preferred analytical technique for the separation and determination of isomeric PASHs in complex natural samples [9–19, 21, 22]. Recently, reversed-phase liquid chromatography (RPLC) on octadecylsilane (C 18 ) stationary phases has been shown to provide unique selectivity for separating isomeric PASHs [23–25].…”

Section: Introductionmentioning

confidence: 99%

Retention behavior of isomeric polycyclic aromatic sulfur heterocycles in gas chromatography on stationary phases of different selectivity

Wilson

Sander

Oña-Ruales

et al. 2017

Journal of Chromatography A

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Retention indices for 48 polycyclic aromatic sulfur heterocycles (PASHs) were determined using gas chromatography with three different stationary phases: a 50% phenyl phase, a 50% liquid crystalline dimethylpolysiloxane (LC-DMPS) phase, and an ionic liquid (IL) phase. Correlations between the retention behavior on the three stationary phases and PASH geometry (L/B and T, i.e., length-to-breadth ratio and thickness, respectively) were investigated for the following four isomer sets: (1) 4 three-ring molecular mass (MM) 184 Da PASHs, (2) 13 four-ring MM 234 Da PASHs, (3) 10 five-ring MM 258 Da PASHs, and (4) 20 five-ring MM 284 Da PASHs. Correlation coefficients for retention on the 50% LC-DMPS vs L/B ranged from r = 0.50 (MM 284 Da) to r = 0.77 (MM 234 Da). Correlation coefficients for retention on the IL phase vs L/B ranged from r = 0.31 (MM 234 Da) to r = 0.54 (MM 284 Da). Correlation coefficients for retention on the 50% phenyl vs L/B ranged from r = 0.14 (MM 258 Da) to r = 0.59 (MM 284 Da). Several correlation trends are discussed in detail for the retention behavior of PASH on the three stationary phases.

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Speciation of alkylated dibenzothiophenes through correlation of structure and gas chromatographic retention indexes

Cited by 49 publications

References 20 publications

Mass Spectra and Retention Indexes for Polycyclic Aromatic Sulfur Heterocycles and Some Alkylated Analogs

Mass Spectra and Retention Indexes for Polycyclic Aromatic Sulfur Heterocycles and Some Alkylated Analogs

Characterization of Nitrogen and Sulfur Compounds in Hydrocracking Feedstocks by Fourier Transform Ion Cyclotron Mass Spectrometry

Retention behavior of isomeric polycyclic aromatic sulfur heterocycles in gas chromatography on stationary phases of different selectivity

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