FT-ICR MS determination of the role of naphthenic acids on the stabilization of alkali/surfactant/polymer emulsified effluents: A field study

Orrego-Ruiz, Jorge A.; Medina-Sandoval, Camila F.; Hinds, Carmen Castillo; Villar-García, Álvaro; Rojas-Ruiz, Fernando A.

doi:10.1016/j.petrol.2019.04.047

Cited by 7 publications

(7 citation statements)

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“…Broadband FT-ICR MS is uniquely suited for molecular-level characterization of ultra-complex mixtures because it can resolve and identify tens of thousands of elemental compositions in a single analysis in a matter of minutes, irrespective of the boiling point. − When combined with separations, FT-ICR MS constitutes a powerful tool to assess petroleum molecular composition and understand the compositional trends responsible for petroleum phase behavior, fouling, and refining. ,− …”

Section: Resultsmentioning

confidence: 99%

Advances in Asphaltene Petroleomics. Part 4. Compositional Trends of Solubility Subfractions Reveal that Polyfunctional Oxygen-Containing Compounds Drive Asphaltene Chemistry

et al. 2020

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Asphaltenes have traditionally been conceived as highly aromatic, alkyl-deficient compounds enriched in pericondensed aromatic “island” motifs. This structural definition evolved into the general notion that aromatic core-dominated interactions (π-stacking) drive asphaltene aggregation, and heteroatom-based intermolecular forces have no significant effect on the overall solubility and aggregation behavior. However, the exclusion of heteroatoms in asphaltene chemistry is inconsistent with the Boduszynski continuum and known asphaltene properties, such as increased heteroatom content relative to maltenes, interfacial activity, and strong adsorption to polar stationary phases. Thus, to determine whether or not heteroatoms are involved in solubility, we have separated asphaltene fractions enriched in single-core (island) or multicore motifs (archipelago) according to their partitioning in n-heptane by two fractionation methods. In the first separation procedure, the acetone fraction from Wyoming deposit n-heptane asphaltenes (island-enriched) was adsorbed on polytetrafluoroethylene powder and Soxhlet extracted with n-heptane. Subfractions were collected after one day, one week, one month, and three months of extraction, and the residue, n-heptane insoluble material, was recovered with a mixture of toluene and dichloromethane. In the second method, the acetone fraction from Athabasca bitumen n-heptane asphaltenes (archipelago-enriched) was fractionated by differential precipitation in mixtures of n-heptane and toluene. The molecular composition of the asphaltene subfractions was accessed by positive-ion atmospheric pressure photoionization coupled to 9.4 T Fourier transform ion cyclotron resonance mass spectrometry and structures were determined by infrared multiphoton dissociation. The compositional trends for heteroatom content, double bond equivalents, and alkyl substitution suggest that the Boduszynski continuum can be extended to asphaltenes. In particular, the compositional range of polyoxygenated asphaltene compounds shifts toward lower aromaticity, whereas oxygen-depleted species are more aromatic. Moreover, the results demonstrate that polyoxygenated species (e.g., O3 and S2O3 classes) are pivotal in asphaltene solubility, as they concentrate in the most polarizable and insoluble asphaltene subfractions. Therefore, the results support the existence of atypical asphaltene species with remarkably low aromaticity that reside in the most insoluble asphaltene subfractions because of their high heteroatom content. Such asphaltene compounds preferentially ionize as protonated molecules rather than radical cations and overlap the compositional range of interfacially active species, consistent with their tendency to participate in hydrogen bonding. Collectively, the results highlight the need for an asphaltene molecular model based on the existence of polyfunctional species capable of interacting with neighboring asphaltene molecules through several intermolecular forces, including London dispersion forces between ali...

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Section: Resultsmentioning

confidence: 99%

Advances in Asphaltene Petroleomics. Part 4. Compositional Trends of Solubility Subfractions Reveal that Polyfunctional Oxygen-Containing Compounds Drive Asphaltene Chemistry

et al. 2020

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“…A study proposed a new isolation method for interfacial material, known as "wet silica," revealing that isolated species contained an abundance of oxygen-and sulfur-containing compounds when compared with crude oil [45]. A compositional analysis by FT-ICR MS in an alkalis/surfactant/ polymer system showed the presence of carboxylic acids, pyrroles, and phenols using MAPS and "wet silica" for the isolation of interfacial material [89].…”

Section: Direct Mass Spectrometry-based Methodmentioning

confidence: 99%

“…O/W emulsions were also found to be stabilized by a synergistic effect of the combination of the surfactant and the C 20 -C 30 carboxylate salts in an alkalis/surfactant/polymer system with pH >8 [89]. In general, two types of naphthenates can be formed: calcium and sodium naphthenates.…”

Section: Role Of Nas In Stabilizing Emulsionsmentioning

confidence: 99%

“…Moreover, some species are detected at trace levels [88], requiring a preconcentration step prior to instrumental analysis. Numerous studies employed liquid-liquid (LLE) and solid-phase extraction (SPE) to extract NAs [88,89,102], but LLE was the most popular method. Sample preparation methods are vital for analyzing NAs by direct MS, enabling selective characterization and reducing ionic suppression effects [64,103].…”

Section: Nas Techniques and Characterizationmentioning

confidence: 99%

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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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“…However, strong emulsification of the produced fluids was found in some oil fields. Orrego-Ruiz et al 241 showed the detailed FT-ICR MS characterization of an alkali/surfactant/polymer flooding obtained from the San Francisco oil field-Colombia. This study allowed disclosing the role of natural organic acids in reducing the interfacial tension which in turn entailed highly stable microemulsions.…”

Section: Characterization For Crude Oil and Its Fractionsmentioning

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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FT-ICR MS determination of the role of naphthenic acids on the stabilization of alkali/surfactant/polymer emulsified effluents: A field study

Cited by 7 publications

References 38 publications

Advances in Asphaltene Petroleomics. Part 4. Compositional Trends of Solubility Subfractions Reveal that Polyfunctional Oxygen-Containing Compounds Drive Asphaltene Chemistry

Advances in Asphaltene Petroleomics. Part 4. Compositional Trends of Solubility Subfractions Reveal that Polyfunctional Oxygen-Containing Compounds Drive Asphaltene Chemistry

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

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

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