Characterization of nonvolatile polar compounds from Brazilian oils by electrospray ionization with FT-ICR MS and Orbitrap-MS

Vanini, Gabriela; Barra, Thamara Andrade; Souza, Lindamara M.; Madeira, Natã C. L.; Gomes, Alexandre O.; Romão, Wanderson; Azevedo, Débora A.

doi:10.1016/j.fuel.2020.118790

Cited by 50 publications

(37 citation statements)

References 35 publications

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“…The FT-ICR MS analyses were performed by a SolariX 9.4T FT-ICR mass spectrometer − (Bruker, Bremen, Germany) equipped with an ICR cell as the infinity cell.…”

Section: Methodsmentioning

confidence: 99%

“…The maximum acceptable accuracy was 3 ppm. The Composer and Compass Data Analysis presents information about the heteroatom classes present in the samples, DBE information, and charts relating carbon number and DBE values. − The DBE is calculated from eq . − where C represents the number of carbons, H the number of hydrogens, N the number of nitrogens in the molecular formula.…”

Section: Methodsmentioning

confidence: 99%

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Study of Thermal Aging of Model Compounds Present in Asphalt Cement by GC/MS, ESI-MS, NMR, and FTIR

et al. 2021

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The study of petroleum asphalt cement (AC) aging is essential for the production of good quality pavements with high durability. Because of the complexity of this material, one of the biggest challenges is understanding the chemical variations that occur in the molecules present in the AC during the aging processes. This work proposes to study 15 standards of model compounds present in the AC composition, representing the fractions of saturated compounds (5-α-cholestane and hexatriacontane), aromatics (hexamethylbenzene, coronene, and benzo-[a]anthracene), nitrogenous compounds (acridine, carbazole, indole, and N,N′-Bis(3-pentyl)perylene-3,4,9,10-bis-(dicarboximide)), sulfur compounds (2-naphthalenethiol, 4,6diethyldibenzothiophene, and naphtho[1,2-b:6,5-b′]dithiophene(NDT)), and naphthenic acids (stearic (SA), pentadecanoic (PA), and sinapinic acids (ASN)), which were thermally aged by two methods: (i) they were subjected to a constant temperature of 80 °C, varying the time of analysis over 5, 10, 15, 30, and 60 days; and (ii) temperatures ranging from 80, 100, 120, to 140 °C for 15 days. The analyses of these compounds were performed by GC/MS, 1 H and 13 C NMR, ESI(−)MS (FT-ICR and LTQ), and FTIR. The results obtained showed that at 80 °C, from 15 days, only the indole standard compound showed the presence of thermal products, i.e., compounds detected from thermal aging of the standard model compounds. When the degradation temperature was increased from 100 to 140 °C, we observed the formation of thermal products at 100 °C in 6 out of 15 model compounds. However, at 140 °C, 12 of the 15 model compounds presented some type of degradation. Reactions of oxidation, polymerization, thermal aging, volatilization, and formation of double bonds were observed.

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“…The FT-ICR MS analyses were performed by a SolariX 9.4T FT-ICR mass spectrometer − (Bruker, Bremen, Germany) equipped with an ICR cell as the infinity cell.…”

Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Study of Thermal Aging of Model Compounds Present in Asphalt Cement by GC/MS, ESI-MS, NMR, and FTIR

et al. 2021

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“…The dynamic operating range for ion acquisition in the ICR cell was configured to m / z 200–1500. All samples were diluted to approximately 1.5 mg/mL in toluene/methanol 1:1 (v/v) solution containing 0.1% (v/v) formic acid and ammonium hydroxide for analysis in ESI (+) and ESI (−) modes, respectively. ,,,, Each solution was injected by direct infusion at a flow of 5 μL/min. The ESI (±) conditions are described in Table 1S (Supporting Information) …”

Section: Methodsmentioning

confidence: 99%

Chemical Characterization and Interfacial Activity of Molecules Isolated from Brazilian Oils by Adsorption onto Wet Silica Particles

et al. 2020

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Petroleum molecules with interfacial activity play a fundamental role in stabilizing water-in-oil (W/O) emulsions and thus have been the focus of many studies. Using the wet silica method, crude oil samples from Brazilian fields (designated P5 and P6) were fractionated into two fractionsone with the interfacially active molecules (IA) and another containing the non-interfacially active molecules (NIA). This fractionation was performed using a mixture of cyclohexane/toluene (1:1 v/v) (CH/TOL) for oils P5 and P6 and n-octane/toluene (1:1 v/v) (OC/TOL) only for oil P6 to evaluate the influence of the solvent system on the profile of the fractions obtained. The fractions obtained and the parent oils were characterized chemically by Fourier-transform infrared spectroscopy (FTIR), 1H-nuclear magnetic resonance (1H-NMR), and electrospray ionization Fourier-transform ion cyclotron resonance mass spectrometry (ESI (±) FT-ICR MS) and analyzed for interfacial activity using systems composed of brine (aqueous phase) and n-heptane/toluene mixture (organic phase). The results from FTIR and 1H-NMR evidenced the polar and aromatic character of the IA fractions, while the predominantly hydrocarbon composition was observed in the NIA fractions as well as their respective parent oils. The characterization by FT-ICR MS showed the influence of the solvent system on the basic species of the IA fractions, by ESI (+), and a difference in the acid compounds of the fractions isolated from the two parent oils, by ESI (−): the IA fraction isolated from P5 presented the compound classes O4[H] and O2[H] as major components, while the major compounds in the IA fractions isolated from P6 with CH/TOL or OC/TOL were O[H], O2[H], and N[H]. Decrease in the interfacial tension values on the order of 30% was observed when comparing each interfacially active fraction with their parent oil.

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“…Another study endeavored to compare the performance of a compact highfield FT-Orbitrap MS to that of a gold-standard FT-ICR MS instrument, reporting similar compositional results in the FT-Orbitrap MS with average mass accuracies below 1 ppm [152]. Similarly, the FT-Orbitrap MS and FT-ICR MS were used for qualitative analysis of polar compounds in crude oil [153], finding the most abundant species in both instruments to be N, N 2 , O 3 , O 1 , O 2 , NO 2 , NS, and OS classes. While O 2 class showed higher relative abundance in the FT-Orbitrap MS, the other classes were detected in lower proportions compared to FT-ICR MS [153].…”

Section: Direct Mass Spectrometry-based Methodmentioning

confidence: 99%

“…Similarly, the FT-Orbitrap MS and FT-ICR MS were used for qualitative analysis of polar compounds in crude oil [153], finding the most abundant species in both instruments to be N, N 2 , O 3 , O 1 , O 2 , NO 2 , NS, and OS classes. While O 2 class showed higher relative abundance in the FT-Orbitrap MS, the other classes were detected in lower proportions compared to FT-ICR MS [153].…”

Section: Direct Mass Spectrometry-based Methodmentioning

confidence: 99%

Naphthenic Acids: Formation, Role in Emulsion Stability, and Recent Advances in Mass Spectrometry-Based Analytical Methods

Facanali

Porto

Crucello

et al. 2021

Journal of Analytical Methods in Chemistry

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Naphthenic acids (NAs) are compounds naturally present in most petroleum sources comprised of complex mixtures with a highly variable composition depending on their origin. Their occurrence in crude oil can cause severe corrosion problems and catalysts deactivation, decreasing oil quality and consequently impacting its productivity and economic value. NAs structures also allow them to behave as surfactants, causing the formation and stabilization of emulsions. In face of the ongoing challenge of treatment of water-in-oil (W/O) or oil-in-water (O/W) emulsions in the oil and gas industry, it is important to understand how NAs act in emulsified systems and which acids are present in the interface. Considering that, this review describes the properties of NAs, their role in the formation and stability of oil emulsions, and the modern analytical methods used for the qualitative analysis of such acids.

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Characterization of nonvolatile polar compounds from Brazilian oils by electrospray ionization with FT-ICR MS and Orbitrap-MS

Cited by 50 publications

References 35 publications

Study of Thermal Aging of Model Compounds Present in Asphalt Cement by GC/MS, ESI-MS, NMR, and FTIR

Study of Thermal Aging of Model Compounds Present in Asphalt Cement by GC/MS, ESI-MS, NMR, and FTIR

Chemical Characterization and Interfacial Activity of Molecules Isolated from Brazilian Oils by Adsorption onto Wet Silica Particles

Naphthenic Acids: Formation, Role in Emulsion Stability, and Recent Advances in Mass Spectrometry-Based Analytical Methods

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