Microstructural evolution of bitumen during the glass transition: An application of digital oil

Cui, Wuge; Huo, Keli; Sugiyama, Shumpei; Liang, Yunfeng; Masuda, Yoshihiro; Morimoto, Masato; Matsuoka, Toshifumi; Boek, Edo S.; Kaito, Yutaro; Nakagawa, Kazunori; Ito, Daisuke

doi:10.1016/j.fuel.2022.127048

Cited by 6 publications

(5 citation statements)

References 62 publications

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“…Conversely, AS03 has a long straight side chain and is more sparsely distributed in spatial locations. The density change curves in Figure a show the same trend as the previous study Figure b shows the correspondence between the H/C ratio and asphaltene density.…”

Section: Resultssupporting

confidence: 82%

“…The density change curves in Figure 3a show the same trend as the previous study. 53 Figure 3b shows the correspondence between the H/C ratio and asphaltene density. The asphaltene mixture model used in this paper was labeled with H/C = 0.92, while those for AS01, AS02, AS03, and AS04 are 0.78, 1.0, 1.36, and 0.94, respectively.…”

Section: Solubility Parameters Of Bulk Systems: Development and Valid...mentioning

confidence: 93%

“…MD simulations were performed using the GROMACS package (version 5.1.5) with the CHARMM general force field (CGenFF), which can reproduce the density of organic liquids very well, , where the error for hydrocarbons is typically within 1–2%. Additionally, it also has good performances in crude oils. ,,, A 9 × 9 × 9 nm box was prepared for holding molecules. The criterion for adding molecules for a condensed liquid state is to maintain a total number of approximately 20,000 atoms in the system.…”

Section: Methodsmentioning

confidence: 99%

“…Additionally, it also has good performances in crude oils. 46,47,53,54 A 9 × 9 × 9 nm box was prepared for holding molecules. The criterion for adding molecules for a condensed liquid state is to maintain a total number of approximately 20,000 atoms in the system.…”

Section: Computational Details 221 Simulation Detailsmentioning

confidence: 99%

“…Molecular dynamics (MD) simulation is an effective approach for predicting macroscopic properties resulting from specific microscopic molecular interactions and structures. ,,,,− In line with HSP principles, Khafal and Mansoori conducted MD simulations to reveal the contribution of van der Waals (vdW), electrostatic, and hydrogen bonding to the aggregation of asphaltene molecules by constructing three different structures of asphaltene molecules and a simple crude oil model consisting of heptane and o -xylene. Using different asphaltene molecular models, including models for two subfractions of asphaltenes, A1 with a rigid core that tends to aggregate easily, A2 with higher flexibility in structure and better solubility in toluene, a highly aromatic island model, and archipelago-type model, the aggregation behavior was studied. − The asphaltene aggregates were observed in various solvents even at low concentrations. , Further investigations revealed that the simulated system exhibited size distribution profiles similar to the gel permeation chromatography (GPC) experimental analyses of asphaltene samples in tetrahydrofuran (THF). , Interestingly, Villegas et al showed that the dipole moment of asphaltene aggregate tends to be zero when the number of molecules in the aggregate increases.…”

Section: Introductionmentioning

confidence: 99%

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Evaluation of Asphaltene Hildebrand and Hansen Solubility Parameters Using Digital Oil Models with Molecular Dynamics Simulation

Huang,

Liang,

Masuda

et al. 2023

Energy Fuels

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The solubility parameter characterizes solubility in terms of simple numbers representing cohesive energy contribution within the molecular system and thus is considered a powerful approach for understanding highly complex systems such as asphaltenes. To obtain solubility parameters, compared with the traditional experimental method, molecular dynamics (MD) simulation provides an efficient approach and gives an explanation at the molecular level. In this study, we calculated the solubility parameters of asphaltenes using MD simulations with the digital oil model that we developed for a domestic oilfield. We have also computed the solubility parameters for more than 20 different solvents, including mixtures, to gain confidence. A new method to calculate asphaltene Hansen solubility parameters (HSPs) in solvents was proposed and implemented. This method uses a small solvent molecule as a probe. It considers different aggregation states and the potential to form hydrogen bonds in solvents, which successfully separate polar and hydrogen bonding contributions from the total cohesive energy. Six types of solvents, including heptane, toluene, isopropyl alcohol (IPA), pyridine, o-xylene, and toluene–IPA mixtures, were employed. For the toluene–IPA mixtures, different concentrations were considered. Utilizing the obtained asphaltene solubility parameters, we drew Hansen solubility sphere diagrams and estimated the solubility of asphaltenes in a solvent using the Flory–Huggins thermodynamic model, which gives results in line with expectations. Furthermore, an optimal toluene–IPA mixing solvent concentration ratio was found for asphaltenes of our target oilfield. This was achieved by tuning the polar and hydrogen bonding interaction contributions in the mixtures. Further onward, using the same method to calculate the solubility parameters for predicting asphaltene deposition risk during production, such as CO2-EOR, will be possible.

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Section: Resultssupporting

confidence: 82%

Section: Solubility Parameters Of Bulk Systems: Development and Valid...mentioning

confidence: 93%

Section: Methodsmentioning

confidence: 99%

Section: Computational Details 221 Simulation Detailsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Evaluation of Asphaltene Hildebrand and Hansen Solubility Parameters Using Digital Oil Models with Molecular Dynamics Simulation

Huang,

Liang,

Masuda

et al. 2023

Energy Fuels

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Controlling the asphaltene precipitation behaviors by changing the position and number of nitrogen in the aromatic heterocyclic pendant of polymers with the assistance of DFT calculations

Jia,

Sun,

Wei

et al. 2024

J of Applied Polymer Sci

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As the largest component in crude oil, asphaltenes are apt to settle out and result in the blockage of pipeline during production and transportation, which largely reduces the safety and economic benefits. In this study, a series of poly(maleic anhydride‐octadecene)s (PMO) amidated by pyrimidine (MD), pyrazine (BQ), pyrazole (BZ), triazole (3DZ), triazine (6J3Q), phenyl triazine (6B3Q) and pyrazolo pyridine (ZBD) were synthesized. The interaction energies between the different polymers and asphaltene were calculated by using density functional theory (DFT). It shows that the greater the number of nitrogen‐containing groups and rings, the higher the interaction energy. Moreover, the position of the nitrogen on the aromatic ring also impacts the interaction energy. The interaction energy between asphaltene and polymer with adjacent N (PMO‐BZ) is larger than that with para‐N (PMO‐BQ) and interstitial N (PMO‐MD). In addition, the performance of polymers on asphaltene precipitation from model oil and crude oil is explored by UV–Vis spectroscopy, turbidity, dynamic light scattering (DLS) and rheological methods. The performance of polymers follows the sequence of PMO‐BZ > PMO‐6J3Q > PMO‐BQ > PMO‐MD > PMO‐6B3Q > PMO‐ZBD, which is not consistent with the change of interaction energy. Apparently, the efficiency of the polymer increases and then declines with the increase of interaction energy. Notably, the polymer (PMO‐BZ) containing monocyclic ring with adjacent N increased the IPP of asphaltenes from 0.363 to 0.800 and reduced the particle size from 1527.2 to 99.7 nm. The interaction energies of PMO‐BZ and PMO‐6J3Q with asphaltene are in the range of 15.87–17.04 KJ/mol, and the polymers with interaction energies in this range are more effective on asphaltene inhibition than the others. Consequently, the interaction energies obtained from DFT calculations can be used to guide the design and synthesis of polymers with nitrogen‐containing heterocyclic pendant for asphaltene inhibition.

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Molecular insights into the dispersibility of asphaltene and crude oil rheological properties under the effect of multi-alkylated aromatic amides

Zhu,

Li,

Han

et al. 2024

Chemical Engineering Science

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Microstructural evolution of bitumen during the glass transition: An application of digital oil

Cited by 6 publications

References 62 publications

Evaluation of Asphaltene Hildebrand and Hansen Solubility Parameters Using Digital Oil Models with Molecular Dynamics Simulation

Evaluation of Asphaltene Hildebrand and Hansen Solubility Parameters Using Digital Oil Models with Molecular Dynamics Simulation

Controlling the asphaltene precipitation behaviors by changing the position and number of nitrogen in the aromatic heterocyclic pendant of polymers with the assistance of DFT calculations

Molecular insights into the dispersibility of asphaltene and crude oil rheological properties under the effect of multi-alkylated aromatic amides

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