Alternation of asphaltene binding arrangement in the presence of chemical inhibitors: Molecular dynamics simulation strategy

Ghamartale, Ali; Rezaei, Nima; Zendehboudi, Sohrab

doi:10.1016/j.fuel.2022.127001

Cited by 23 publications

(7 citation statements)

References 60 publications

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“…The introduction of benzimidazolium-based additives seems to change the arrangement of the asphaltene aggregates, allowing an enhancement of the π−π stacking interactions, which are quadrupolar in nature. 16 The complete RDFs for the C18−C18 interactions are shown in Figures S5−S8, where the different types of IL additives studied (including imidazolium and systems without ILs) are compared for the different solvent compositions and grouped by the IL alkyl side chain length. Some general conclusions can be drawn from the observation of the figures.…”

Section: Liquid Structurementioning

confidence: 99%

“…Ghamartale et al 16 studied the binding arrangement between asphaltenes (two different models, with and without heteroatoms) and the ionic liquids 1-butyl-3-methyl imidazolium chloride and bromide (together with octyl phenol) in nheptane solutions by molecular dynamics simulations. They concluded that ILs reduce the parallel binding between asphaltenes and attributed this reduction to the cation− quadrupole interactions being stronger and replacing the quadrupole−quadrupole interactions between asphaltene molecules.…”

Section: Introductionmentioning

confidence: 99%

“…Ghamartale et al . studied the binding arrangement between asphaltenes (two different models, with and without heteroatoms) and the ionic liquids 1-butyl-3-methyl imidazolium chloride and bromide (together with octyl phenol) in n -heptane solutions by molecular dynamics simulations.…”

Section: Introductionmentioning

confidence: 99%

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Influence of Ionic Liquids on the Aggregation and Preaggregation Phenomena of Asphaltenes in Model Solvent Mixtures by Molecular Dynamics Simulations and Quantum Mechanical Calculations: The Effect of Cation’s Shape and Size

Martins,

Celia-Silva,

Ramalho

et al. 2024

Energy Fuels

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The merits of ionic liquids (ILs) as additives to influence the solid−liquid behavior of asphaltenes in crude oil models have been well-established in specialized literature. The direct interaction between ionic liquids and asphaltenes is recognized as a key factor for the role played by these additives in the asphaltene aggregation process, which depends on the structural details of the ionic liquids used (and also on the model considered for the asphaltenes). In a previous paper, we presented a systematic molecular dynamics study of the effect of 1-alkyl-3methyl imidazolium-based ionic liquids on the asphaltene preaggregation phenomenon, focusing on the effect of the alkyl chain length of the cation and on the size of the anion. In this work, this study is extended to evaluate the effect of the shape and size of the cation head. The preaggregation phenomena in toluene/n-heptane mixtures and the asphaltene/IL interactions are studied here by molecular dynamics simulations and density functional theory (DFT) calculations, using N-alkylpyridinium, N-alkyl isoquinolinium, and 1-alkyl-3-methyl benzimidazolium chloride ILs, with alkyl chains containing between 4 and 10 carbon atoms as additives. These additives show a general dispersing effect in n-heptane-rich systems, with the N-alkyl isoquinolinium-based ILs with longer alkyl chains (especially C 8 but also C 10 ) being the most active ones. The asphaltene/IL interaction is found to be enhanced by cations with two condensed aromatic rings instead of one, which seems to highlight the importance of the π−π stacking contact. However, the most interactive family of ILs (1-alkyl-3-methyl benzimidazolium chloride) is also the one that induces asphaltene aggregation, especially for shorter alkyl side chains (with 33% larger aggregates than the systems without additive for mixtures with equal proportions of the two solvents), probably representing a binder effect for asphaltenes. Although by molecular simulation, the N-alkyl isoquinolium-based ILs showed the clearest dispersing effect toward asphaltenes and the most intense interactions with them, they also presented the lowest interaction energies of the asphaltene−IL dimers obtained by DFT, and this was found to be the consequence of a specific cation−anion interaction only for this family of ILs, which is close to a covalent bond. This work is a valuable addition to the understanding of the molecular interactions that govern asphaltene aggregation in the presence of additives, and contributes to the selection and design of better additives to prevent or induce asphaltene aggregation in crude oil.

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Section: Liquid Structurementioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Influence of Ionic Liquids on the Aggregation and Preaggregation Phenomena of Asphaltenes in Model Solvent Mixtures by Molecular Dynamics Simulations and Quantum Mechanical Calculations: The Effect of Cation’s Shape and Size

Martins,

Celia-Silva,

Ramalho

et al. 2024

Energy Fuels

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“…Further, π−π stacking was observed between aromatic IL and asphaltene within this study. In recent study, Ghamartale et al 29 conducted MD simulations to assess the changes in the aggregation of two continental asphaltene structures in n-heptane (7 wt % of asphaltene), in the presence and absence of three chemical inhibitors: octylphenol and two ILs, i.e., 1-butyl- The existing experimental works on asphaltene separation using ILs highlight several important aspects as elaborated above. However, molecular insights of interaction between IL anion and asphaltene based on the MD simulation technique are still lacking to the best of our knowledge.…”

Section: Introductionmentioning

confidence: 99%

“…Further, π–π stacking was observed between aromatic IL and asphaltene within this study. In recent study, Ghamartale et al 29 conducted MD simulations to assess the changes in the aggregation of two continental asphaltene structures in n -heptane (7 wt % of asphaltene), in the presence and absence of three chemical inhibitors: octylphenol and two ILs, i.e., 1-butyl-3-methylimidazolium chloride ([BMIM][Cl]) and 1-butyl-3-methylimidazolium bromide ([BMIM][Br]). The study provided a detailed account of the mechanisms involved in asphaltene aggregation in the presence of ILs.…”

Section: Introductionmentioning

confidence: 99%

Probing the Effect of Aliphatic Ionic Liquids on Asphaltene Aggregation Using Classical Molecular Dynamics Simulations

2023

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One of the major constituents of heavy oil is asphaltenes. They are responsible for numerous problems in petroleum downstream and upstream processes, such as catalyst deactivation in heavy oil processing and blocking pipes while transporting crude oil. Probing the efficiency of new nonhazardous solvents in separating asphaltenes from crude oil is key to avoid conventional volatile and hazardous solvents by replacing these conventional solvents with new ones. In this work, we have investigated the efficiency of ionic liquids to separate asphaltenes from organic solvents (such as toluene and hexane) using molecular dynamics simulations. Triethylammonium-dihydrogen-phosphate and triethylammonium acetate ionic liquids are considered in this work. Various structural and dynamical properties are calculated, such as radial distribution function, end-to-end distance, trajectory density contour, and diffusivity of asphaltene in the ionic liquid-organic solvent mixture. Our results explain the role of anions, i.e., dihydrogen-phosphate and acetate ions, in separating asphaltene from toluene and hexane. Our study provides an important revelation about the dominant role played by the IL anion in intermolecular interactions which depends on the type of solvent (i.e., toluene or hexane) in which the asphaltene is present. The anion induces enhanced aggregation in the asphaltene-hexane mixture compared to the asphaltene-toluene mixture. The molecular insights obtained within this study on the role played by ionic liquid anion in asphaltene separation are key for the preparation of new ionic liquids for asphaltene precipitation applications.

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Doping Si/O to enhance interfacial occupancy of demulsifiers for low‐carbon breaking of water‐in‐heavy oil emulsions

Tian,

He,

Zhang

et al. 2024

AIChE Journal

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Separating water‐in‐heavy oil (W/HO) emulsions at low (room) temperature is challenging when exploiting heavy oil. We propose an adaptable strategy for constructing Si/O‐doped demulsifiers. A nonionic demulsifier (APBMP) has been synthesized based on polysiloxane modified by allyl polyether and butyl acrylate. APBMP achieves 95.97% dehydration within 5 min for W/HO emulsions at 288.15 K and complete dehydration in 15 min at 323.15 K. Mechanistic studies found that doping Si/O into the demulsifier molecules increases the number of hydrogen bond sites, which enables the demulsifiers to quickly disperse natural stabilizers (e.g., asphaltenes) and replace them at the oil–water interfacial film. The demulsifiers prefer to occupy the interfacial sites rather than dissolve into the bulk oil or water phases. Driven by hydrogen‐bond‐dominated noncovalent interactions, the oil–water interfacial film is softened, reconstructed, and broken. These findings provide insights into developing novel materials for oil–water separations in a low‐carbon way.

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Alternation of asphaltene binding arrangement in the presence of chemical inhibitors: Molecular dynamics simulation strategy

Cited by 23 publications

References 60 publications

Influence of Ionic Liquids on the Aggregation and Preaggregation Phenomena of Asphaltenes in Model Solvent Mixtures by Molecular Dynamics Simulations and Quantum Mechanical Calculations: The Effect of Cation’s Shape and Size

Influence of Ionic Liquids on the Aggregation and Preaggregation Phenomena of Asphaltenes in Model Solvent Mixtures by Molecular Dynamics Simulations and Quantum Mechanical Calculations: The Effect of Cation’s Shape and Size

Probing the Effect of Aliphatic Ionic Liquids on Asphaltene Aggregation Using Classical Molecular Dynamics Simulations

Doping Si/O to enhance interfacial occupancy of demulsifiers for low‐carbon breaking of water‐in‐heavy oil emulsions

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