Mass Spectrometry in Petroleum Chemistry (Petroleomics) (Review)

Борисов, Р. С.; Куликова, Л. Н.; Заикин, В. Г.

doi:10.1134/s0965544119100025

Cited by 30 publications

(33 citation statements)

References 222 publications

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“…Reactions were performed in screw-capped glass test tubes with magnetic stir bars in an air atmosphere unless otherwise stated. Thiols were purchased from commercial sources and checked by 1 H and 13 C NMR spectroscopy prior to use. (IMes)Pd(acac)Cl, but-3-yn-1-yltriphenylphosphonium bromide, and N-(5-hexynyl)phthalimide were synthesized according to described procedures [38][39][40].…”

Section: General Proceduresmentioning

confidence: 99%

“…NMR measurements were performed using a Bruker AVANCE 600, Bruker DRX-500, Bruker Fourier 300 spectrometers operating at 600.1 and 500.1, 300.1 and 150.0, and 125.8 and 75.5 MHz for 1 H and 13 C, respectively. The 1 H and 13 C chemical shifts were referenced to internal standards provided by the solvent or relative to TMS as an external standard for spectra in CDCl 3 .…”

Section: General Proceduresmentioning

confidence: 99%

“…1 H NMR (600 MHz, CDCl 3 ) δ, ppm: 7.50 (s, 1H), 7.07 (s, 1H), 6.95-6.92 (m, 1H), 4.11 (t, J = 6.8 Hz, 2H), 2.18 (td, J = 6.7, 2.7 Hz, 2H), 2.06 (t, J = 2.7 Hz, 1H), 1.97 (quint, J = 6.7 Hz, 2H). 13 3-methyl-1-(pent-4-yn-1-yl)-1H-imidazolium chloride. 1-Methyl-1H-imidazole (2 mmol, 0.159 mL) and 5-chloropent-1-yne (2 mmol, 0.212 mL) were mixed in a test tube, purged with argon, and heated at 90 • C for 24 h. As a result, the product in the form of a thick brown liquid was formed quantitatively and did not require purification.…”

Section: Synthesis Of 1-(pentyn-4-yn-1-yl)-1h-imidazole (2a)mentioning

confidence: 99%

“…s, 1H), 5.02 (s, 1H), 4.75 (s, 1H), 3.94 (t, J = 7.0 Hz, 2H), 2.69 (t, J = 7.3 Hz, 2H), 2.23 (t, J = 7.3 Hz, 2H), 2.09-1.98 (m, 2H), 1.70-1.59 (m, 2H), 1.41-1.28 (m, 4H), 0.90 (t, J = 7.0 Hz, 3H). 13…”

Section: Model Reaction Of Thiol 1a With Alkyne 2a In Petroleum Mediummentioning

confidence: 99%

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ESI-MS Analysis of Thiol-yne Click Reaction in Petroleum Medium

2021

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Petroleum contains a large number of heteroatomic compounds, but today, most of them are not efficiently utilized. The constant development of the sustainability concept recalls for rethinking the usage of fossil resources with improved chemical utility. In order to initiate research aimed at involving active petroleum compounds in chemical transformations, a new analytical method for product detection is needed. Here, we study the click reaction of thiols with alkynes, leading to the formation of α-vinyl sulfides directly in the petroleum environment. The reaction was carried out using an (IMes)Pd(acac)Cl catalyst, which demonstrated tolerance to petroleum components. In this study, the concentration of thiols ranged from 1 M to 0.01 M (from 8% to 0.1%). To detect products at low concentrations, a special alkyne labeled with an imidazole moiety was used. This approach made it possible to observe the formation of vinyl sulfides by electrospray ionization mass spectrometry (ESI-MS), which provides an opportunity for further optimization of the reaction conditions and future developments for the direct involvement of oil components in chemical reactions.

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Section: General Proceduresmentioning

confidence: 99%

Section: General Proceduresmentioning

confidence: 99%

Section: Synthesis Of 1-(pentyn-4-yn-1-yl)-1h-imidazole (2a)mentioning

confidence: 99%

Section: Model Reaction Of Thiol 1a With Alkyne 2a In Petroleum Mediummentioning

confidence: 99%

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ESI-MS Analysis of Thiol-yne Click Reaction in Petroleum Medium

2021

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“…Although the coupling of GC with soft ionizations‐MS has been reported in the 1970s, this interesting hyphenation was expanded in the last decade, probably due to the progress in instrument technology. Different soft ionization techniques have been coupled to GC systems in the analysis of petrochemical samples; however, no record seems to be reported by the use of soft ionizations‐MS coupled with GC for the analysis of biofuels and related products [89]. Advantages and drawbacks of the hyphenation between the most common atmospheric pressure ionization‐MS interfaces and GC systems and new developments in source geometry, ion source miniaturization, multipurpose ion source constructions, and comparison with GC‐FID and GC‐EI‐MS detections have been reviewed by Li and co‐workers [90].…”

Section: Ms Detectionmentioning

confidence: 99%

Advanced mono‐ and multi‐dimensional gas chromatography–mass spectrometry techniques for oxygen‐containing compound characterization in biomass and biofuel samples

Beccaria

Siqueira

Maniquet

et al. 2020

J of Separation Science

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A wide variety of biomass, from triglycerides to lignocellulosic‐based feedstock, are among promising candidates to possibly fulfill requirements as a substitute for crude oils as primary sources of chemical energy feedstock. During the feedstock processing carried out to increase the H:C ratio of the products, heteroatom‐containing compounds can promote corrosion, thus limiting and/or deactivating catalytic processes needed to transform the biomass into fuel. The use of advanced gas chromatography techniques, in particular multi‐dimensional gas chromatography, both heart‐cutting and comprehensive coupled to mass spectrometry, has been widely exploited in the field of petroleomics over the past 30 years and has also been successfully applied to the characterization of volatile and semi‐volatile compounds during the processing of biomass feedstock. This review intends to describe advanced gas chromatography–mass spectrometry‐based techniques, mainly focusing in the period 2011–early 2020. Particular emphasis has been devoted to the multi‐dimensional gas chromatography–mass spectrometry techniques, for the isolation and characterization of the oxygen‐containing compounds in biomass feedstock. Within this context, the most recent advances to sample preparation, derivatization, as well as gas chromatography instrumentation, mass spectrometry ionization, identification, and data handling in the biomass industry, are described.

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