Essential role of structure, architecture, and intermolecular interactions of asphaltene molecules on properties (self-association and surface activity)

Hassanzadeh, Masoumeh; Abdouss, Majid

doi:10.1016/j.heliyon.2022.e12170

Cited by 8 publications

(6 citation statements)

References 216 publications

(254 reference statements)

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“…According to the literature data, ,,,, the composition of nanoaggregates of asphaltenes is characterized by the presence of stacked structures formed by aromatic sheets, along the edges of which paraffin chains are located. The ordered stacking of aromatic sheets, mainly due to stacking π–π interactions between arene fragments of the “face-to-face” type and interactions between functional groups of the “edge-to-face” type, provides the formation of a stacked crystal-like structure. , In the case of disordered stacking of aromatic sheets, the stacks of an unstructured (amorphous) structure are formed due to the presence of a developed alkyl substitution, which limits the formation of structured stacks due to steric interactions. The stacks of an amorphous structure are formed in the case of the disordered stacking of aromatic sheets when the formation of structured stacks is limited due to steric interactions in the presence of a developed alkyl substitution. , …”

Section: Resultsmentioning

confidence: 99%

Structural Organization of Asphaltenes and Resins and Composition of Low Polar Components of Heavy Oils

et al. 2023

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Comparative characteristics of resins, asphaltenes, and low polar components of heavy oils from the Ashalchinskoye (I) and Nurlatskoye (II) oil fields (Republic of Tatarstan, Russia) are given. These oils differ in the age of host rocks (Permian and Devonian, respectively) and the content of their components and heteroatoms. An X-ray phase analysis and scanning and transmission electron microscopy reveal that, in contrast to smooth surface asphaltenes of oil I, asphaltenes of oil II are characterized by a loose and porous surface and smaller sizes of nanoaggregates. Nanoaggregates form a disorderly tangled structure because of the alkyl side-chain configuration, which makes it difficult to stack aromatic sheets. The crystallites of nanoaggregates of asphaltenes of oil II are smaller than the crystallites of nanoaggregates of asphaltenes of oil I. The application of the method of structural-group analysis based on the use of the measured indicators of the elemental composition, average molecular weights, and the results of 1H NMR spectroscopy made it possible to establish that overall sizes of mean molecules of resins and asphaltenes of heavy oil I are larger due to the increased content of aromatic and naphthenic cycles in the naphthenoaromatic system. A feature of the structure of the resin–asphaltene components of oil II is a greater number of alkyl substituents in the side chains. According to gas chromatography–mass spectrometry (GC–MS) analysis, the low polar components under study are characterized by a similar set of saturated hydrocarbons (n-alkanes, mono-, and polycycloalkanes) but differ in the composition of identified aromatic hydrocarbons and heteroorganic compounds. A feature of the low polar components of oil II is the presence of a wider range of n-alkyl- and phenylalkyl-substituted benzenes and nitrogen- and oxygen-organic compounds in their composition.

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Section: Resultsmentioning

confidence: 99%

Structural Organization of Asphaltenes and Resins and Composition of Low Polar Components of Heavy Oils

et al. 2023

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“…The choice of asphaltene concentrations used for this study was based on our insights into the aggregation behavior of asphaltenes in the model oil solution (85% aliphatic oil base and 15% toluene) in previous research findings. 47 Using liquid-state 1 H NMR, we found a distinctive change in the trend of the slope of mass fraction dependence of the NMR asphaltene signal. We observed a consistent linear increase in the asphaltene signal with respect to the asphaltene mass fraction, maintaining this trend until reaching 80 ppm.…”

Section: Sample Preparationmentioning

confidence: 92%

“…Asphaltenes comprise heavy crude oil molecules containing compounds with a broad range of molecular weights, exhibiting increased polarization and surface activity. 1 Asphaltene molecules from various oils have been documented with weights ranging from several thousand to a few hundred grams per mole, typically falling between 40,000 and 300 g/mol. 2 However, it is widely acknowledged and accepted that petroleum asphaltenes typically exhibit a median molecular weight within the range of 550–750 g/mol.…”

Section: Introductionmentioning

confidence: 99%

Asphaltene Adsorption on Solid Surfaces Investigated Using Quartz Crystal Microbalance with Dissipation under Flow Conditions

Jagadisan,

Banerjee

2024

ACS Omega

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Asphaltenes can cause operational challenges in petroleum production facilities and adversely affect production by adsorption on mineral surfaces and alteration of the oil wettability of reservoirs. Therefore, understanding asphaltene adsorption mechanisms and their effects is crucial to improving the efficiency of oil production and reducing costs. In this study, we focus on understanding the impact of asphaltene concentration and the depositing environment of asphaltene adsorption on solid surfaces using the quartz crystal microbalance with dissipation (QCM-D) technique. The initial and long-term kinetics of adsorption at different concentrations were examined on three different solid surfaces including silicon dioxide to represent quartz mineral, stainless steel, and gold. The frequency−dissipation data showed evidence of monolayer adsorption initially, followed by multilayer formation. At short times, the adsorbed mass increased linearly with time, suggesting that the process was kinetically controlled rather than diffusion-controlled. The results were reproducible and did not depend on convection velocity but did depend on the surface material. At later stages, the monolayer development appeared to follow the random sequential adsorption (RSA) theory. Once multilayer adsorption commenced, the rates agreed well with the two-layer model of Zhu and Gu, 1990. The impact of asphaltene adsorption on the wettability of the surface was examined using contact angle studies, which showed decreasing water wettability with an increase in the adsorbed mass. The contact angle of water after 12 h of adsorption leveled off at around 100°on all three surfaces. Contact angle measurements were also used to evaluate if brine salinity causes the wettability alteration of surfaces with the adsorbed asphaltene. The results indicate that at 3% NaCl solution, the contact angle decreased only slightly by less than 2°.

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“…Due to the complex constitution of asphaltenes, the insoluble aggregates are stabilized by dispersive, polarization, and electrostatic interactions, arising mainly from London forces, π-π stacking, exchangerepulsion contributions, hydrogen bonding and dipole-dipole interactions [23][24][25][26]. Recently, Hassanzadeh and Abdouss [27], based on studies using the supramolecular assembly model by Gray et al [28] and the nanoaggregate model by Yen-Mullins [29], have proposed a supramolecular organization model of asphaltene aggregation that combines cooperative binding by acid-base interactions, hydrogen bonding, π-π stacking, and metal coordination, as well as the formation of hydrophobic pockets, porous networks, and host-guest complexes. All these diverse supramolecular interactions are important for the attraction between asphaltene molecules that leads up to generate organic scaling.…”

Section: Introductionmentioning

confidence: 99%

Density Functional Theory Investigation of the Contributions of π−π Stacking and Hydrogen Bonding with Water to the Supramolecular Aggregation Interactions of Model Asphaltene Heterocyclic Compounds

Lessa,

Stoyanov,

Carneiro

et al. 2024

Preprint

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A complex supramolecular process involving electrostatic and dispersion interactions, asphaltene aggregation is associated with detrimental petroleum deposition and scaling that pose challenges to petroleum recovery, transportation, and upgrading. The density functional ωB97X-D with a dispersion correction was employed to investigate supramolecular aggregates incorporating heterocycles dimers with 0, 1, 2, and 3 water molecules forming a stabilizing bridge connecting the monomers. The homodimers of seven heterocyclic model compounds, representative of moieties commonly found in asphaltene structures were studied: pyridine, thiophene, furan, isoquinoline, pyrazine, thiazole, and 1,3-oxazole. The contributions of hydrogen bonding involving water bridges spanning between dimers and π−π stacking to the total interaction energy were calculated and analyzed. The distance between the planes of the aromatic rings is correlated with the π-π stacking interaction strength. All the dimerization reactions are exothermic, although not spontaneous. This is mostly modulated by the strength of the hydrogen bond of the water bridge and the π-π stacking interaction. Dimers bridged by two water molecules are more stable than with additional water molecules or without any water molecule in the bridge. Energy decomposition analysis show that the electrostatic and polarization components are the main stabilizing terms for the hydrogen bond interaction in the bridge, contributing with at least 80% of the interaction energy in all dimers. The non-covalent interaction analysis confirms the molecular sites that have the strongest (hydrogen bond) and weak (π-π stacking) attractive interactions. They are concentrated in the water bridge and in the plane between the aromatic rings, respectively.

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Essential role of structure, architecture, and intermolecular interactions of asphaltene molecules on properties (self-association and surface activity)

Cited by 8 publications

References 216 publications

Structural Organization of Asphaltenes and Resins and Composition of Low Polar Components of Heavy Oils

Structural Organization of Asphaltenes and Resins and Composition of Low Polar Components of Heavy Oils

Asphaltene Adsorption on Solid Surfaces Investigated Using Quartz Crystal Microbalance with Dissipation under Flow Conditions

Density Functional Theory Investigation of the Contributions of π−π Stacking and Hydrogen Bonding with Water to the Supramolecular Aggregation Interactions of Model Asphaltene Heterocyclic Compounds

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