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

Xiu, Chen; Chen, Xu; Zhang, Weilai; Ma, Chao; Liu, Xuxia; Zhao, Suoqi; Shi, Quan

doi:10.1021/acs.energyfuels.7b03630

Cited by 30 publications

(15 citation statements)

References 58 publications

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“…A total of 1 mL of DCM was added to the residue, and the mixture was ultrasonicated for 5–10 min in a tightly closed vial to dissolve the oil sample but leave excess Girard T reagent undissolved. Girard T reagent was then removed by filtration on a PTFE filter, which was subsequently washed with DCM until the filtrate was colorless, and the filtrate was subjected to +ESI FT-ICR MS analysis. , …”

Section: Materials and Methodsmentioning

confidence: 99%

“…Recently, high-resolution mass spectrometry, such as Fourier transform ion cyclotron resonance mass spectrometry (FT-ICR MS) , and Orbitrap mass spectrometry (Orbitrap MS), coupled with electrospray ionization (ESI) have been used for fossil fuel analysis, , which provided molecular composition of complex mixtures. ESI selectively ionizes polar species by generation of protonated or deprotonated ions ([M + H] + or [M – H] − ). , Nonpolar molecules that are not ionic in solution or not readily ionized by Brønsted or Lewis acid/base chemistry are not accessed by ESI. , Ketones as weakly polar oxygen-containing compounds showed enhanced detection at high ranges of m / z by adding acid at a sufficient concentration, and the Girard T reagent can be used to selectively create a positively charged quaternary ammonium moiety on carbonyls that significantly lower the limit of detection in the positive mode. , As an alternative, atmospheric pressure photoionization (APPI) can ionize nonpolar species …”

Section: Introductionmentioning

confidence: 99%

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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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Section: Materials and Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Molecular Characterization of Ketones in a Petroleum Source Rock

et al. 2018

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“…Alhassan et al 184 derived ketones in fossil fuels to positively charged compounds with Girard T; the products could be detected directly by (+)ESI. By an additional hydrolysis process on the derivatives, Chen et al 185 developed an isolation method and applied it to the separation of ketones from a coal tar. The Girard T reagent reacted with ketones by introducing a charged quaternary ammonium moiety on the carbonyl to form water-soluble hydrazones.…”

Section: Approaches and Applications Formentioning

confidence: 99%

Molecular Characterization of Fossil and Alternative Fuels Using Electrospray Ionization Fourier Transform Ion Cyclotron Resonance Mass Spectrometry: Recent Advances and Perspectives

et al. 2021

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Molecular composition analysis of petroleum and alternative fuels has been considered as one of the greatest challenges in analytical chemistry. The rapid development of Fourier transform ion cyclotron resonance mass spectrometry (FT-ICR MS) has provided an opportunity to solve this problem. High mass resolution power and mass accuracy enable the separation of isobaric compounds in a complex mixture and assignment of their molecular composition. The combination of electrospray ionization (ESI) with FT-ICR MS achieves direct analysis of polar compounds in petroleum even if they are in trace amounts in the complex matrix. FT-ICR MS has made a great contribution to the chemical understanding of petroleum and alternative fuels; the relevant application is sometimes called “petroleomic analysis”. Hundreds of journal articles have been published over the past two decades using FT-ICR MS instruments to study the molecular composition of petroleum and alternative fuels, in which most of them used ESI as the ionization source. This review will present an overview of the studies regarding the petroleomic characterization of fossil and alternative fuels by FT-ICR MS coupled with ESI and a critical review of their main findings relevant to the chemical composition. Special features of this review are (1) covering the entire historical period; (2) focusing on ESI ionization; (3) a systematic review of the composition of almost all the components and compound classes, including but not limited to petroleum, coal-derived liquids, biofuels, and their distillates; asphaltenes, heavy residues, interfacial active substances; hydrocarbons and heteroatoms; and polar and nonpolar compounds. In addition, the challenges and further research directions will be proposed. This review focuses on the advances enabled by ultrahigh resolving power FT-ICR MS in a tribute to Professor Alan G. Marshall.

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“…The GirT derivatives (hydrazones) can be easily separated by column chromatography and then converted to the original AKs by hydrolysis in high yield [28,29]. Figure 4 is the total ion chromatogram (TIC) of the AKPs.…”

Section: Characterization Of Akps In the Mss And Sss By Gcms And þEsi Orbitrap Msmentioning

confidence: 99%

“…Recently, a method of Girard reagent derivatization followed by high resolution MS has been successfully used for the analysis of AKs in low-temperature coal tar. Moreover, these derivatives can be easily separated by column chromatography and then converted to the original AKs by hydrolysis in high yield [29].…”

Section: Introductionmentioning

confidence: 99%

Molecular characterization of aldehydes and ketones in particle phase of mainstream and sidestream cigarette smoke

et al. 2019

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Aldehydes and ketones (AKs) in cigarette smoke are risk to humans and environment. Due to the complexity of itself and the interference of the smoke tar matrix, the aldehydes and ketones in particle phase (AKPs) of mainstream smoke (MSS) and sidestream smoke (SSS) have not been well investigated. In this study, the AKPs of MSS and SSS were derivatized into polar products by reaction with Girard T reagent. The derivatives were isolated rapidly by column chromatography and analysed by Fourier transform ion cyclotron resonance mass spectrometry (FT-ICR MS). Fifteen species of aldehydes and ketones were detected by positive ion electrospray ionization (ESI) FT-ICR MS: O 1–6 , N 1 O 1–4 , N 2 O 1–3 and N 3 O 2–3 . The total number of AKPs obtained by ESI FT-ICR MS in MSS and SSS is about 1100 and 970, respectively. After hydrolysis, the original AKPs were obtained and 63 carbonyls were identified and quantified by gas chromatography–mass spectrometry (GCMS). The nitrogen-containing and high-oxygen AKPs were further characterized by Orbitrap mass spectrometry. Structures of compounds with high relative abundance in the mass spectrum were speculated (e.g. a series of degradants of cembrenediol) by comparison with the results of GCMS.

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

Cited by 30 publications

References 58 publications

Molecular Characterization of Ketones in a Petroleum Source Rock

Molecular Characterization of Ketones in a Petroleum Source Rock

Molecular Characterization of Fossil and Alternative Fuels Using Electrospray Ionization Fourier Transform Ion Cyclotron Resonance Mass Spectrometry: Recent Advances and Perspectives

Molecular characterization of aldehydes and ketones in particle phase of mainstream and sidestream cigarette smoke

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