Self-Accumulation of Aromatics at the Oil−Water Interface through Weak Hydrogen Bonding

Kunieda, Makoto; Nakaoka, Kennichi; Liang, Yunfeng; Miranda, Caetano R.; Ueda, Akira; Takahashi, Satoru; Okabe, Hiroshi; Matsuoka, Toshifumi

doi:10.1021/ja107519d

Cited by 199 publications

(228 citation statements)

References 38 publications

Supporting

Mentioning

199

Contrasting

Unclassified

Order By: Relevance

“…This observation has been reported previously [36] as a conclusion of a molecular simulation study of oil/water systems employing atomistically-detailed force fields. Since the aromatic/water interfacial tension is in general lower than the corresponding alkane/water tension, the lower mixture tension is presumed to be driven by an accumulation of aromatics at the interface.…”

Section: Conclusion and Observationssupporting

confidence: 84%

Prediction of the water/oil interfacial tension from molecular simulations using the coarse-grained SAFT-γ Mie force field

Herdes

Ervik

Mejı́a

et al. 2018

Fluid Phase Equilibria

View full text Add to dashboard Cite

This work is framed within the Ninth Industrial Fluid Properties Simulation Challenge, with the aim of assessing the capability of molecular simulation methods and force fields to accurately predict the interfacial tension of oil + water mixtures at high temperatures and pressures. The challenge focused on predicting the liquid-liquid interfacial tension of binary mixtures of dodecane + water, toluene + water and a 50:50 (wt%) mixture of dodecane:toluene + water at 1.825 MPa (250 psig) and temperatures from 110 to 170 °C. In our entry for the challenge, we employed coarse-grained intermolecular models parametrized via a top-down technique in which an accurate equation of state is used to link experimentally observed macroscopic properties of fluids with the force-field parameters. The state-of-the-art version of the statistical associating fluid theory (SAFT) for potentials of variable range as reformulated in terms of the Mie potential is employed here. Interfacial tensions are calculated through a direct method, where an elongated simulation cell is sampled through molecular dynamics in the isobaric-isothermal constant area ensemble (NP zz AT). The coarse-grained nature of the force field allows for the accelerated calculation of relatively large systems. The binary interaction parameters that describe the crossinteractions have been obtained in previous works by fitting to interfacial tensions of the constituent binaries at lower pressures and temperatures; these are taken as constant for all conditions and mixtures studied. After disclosure of the challenge results, we observe that the interfacial properties of the mixtures are described with an error of less than 5 mN/m over the whole range of conditions, demonstrating the accuracy and transferability of the top-down SAFT-γ Mie force field approach.

show abstract

Section: Conclusion and Observationssupporting

confidence: 84%

Prediction of the water/oil interfacial tension from molecular simulations using the coarse-grained SAFT-γ Mie force field

Herdes

Ervik

Mejı́a

et al. 2018

Fluid Phase Equilibria

View full text Add to dashboard Cite

show abstract

“…As toluene accumulates at the interface, the DodTol/water IFT is lower than what the ideal mixture formula (2) could predict, explaining the apparent behavior of the errors of the calculated IFT values. This accumulation of toluene at the organic phase/water interface has been already observed in other aromatics+aliphatics/water systems and has been traced to the presence of weak hydrogen bonds between the water molecules and the aromatics [15].…”

Section: Resultssupporting

confidence: 62%

“…However, more recently, complex mixtures consisting of alkanes, cycloalkanes and aromatic molecules [15,16] even including an oil polar fraction [17] have been considered, recognizing the importance that the composition has in the properties of crude oils. These theoretical simulations allow us to understand structure and properties of the interface.…”

Section: Introductionmentioning

confidence: 99%

Molecular dynamics simulations of the role of salinity and temperature on the hydrocarbon/water interfacial tension

et al. 2017

View full text Add to dashboard Cite

Interfacial tension of some hydrocarbon/water systems, including a mixture of aliphatic and aromatic hydrocarbons, has been estimated on the basis of molecular dynamics simulations. The dependence of the interfacial properties on the salinity of the aqueous phase and the temperature has been simulated. Different concentrations in NaCl and CaCl 2 up to 2 M have been used. It is found that, in all considered cases, interfacial tension increases with salt concentration. This effect depends on the preference of the salt ions for the bulk of the aqueous phase that, in turns, results in an increased difficulty for the water molecules to be at the interface. The influence of salinity is fundamentally electrostatic in origin and does not depends on the chemical nature of the salt cation. Finally, the impact of temperature on the dodecane/brine interfacial tension has also been inspected. A decreasing of the values of the interfacial tension is found in agreement, both in trend and magnitude, with experimental available data.

show abstract

“…It is clear that the chemistry of the fluorophore which often bases on fused aromatic rings is different from any other chemistry in the system. It is known that aromatics prefer the interfaces between water and oil (alkanes) [43]. So we would expect as is seen here that the aromatic dye segments locate at the interface and may disrupt the lipid packing in their vicinity.…”

Section: Introductionmentioning

confidence: 53%

Molecular modeling of lipid probes and their influence on the membrane

Faller

2016

Biochimica et Biophysica Acta (BBA) - Biomembranes

View full text Add to dashboard Cite

In this review a number of Molecular Dynamics simulation studies are discussed which focus on the understanding of the behavior of lipid probes in biomembranes. Experiments often use specialized probe moieties or molecules to report on the behavior of a membrane and try to gain information on the membrane as a whole from the probe lipids as these probes are the only things an experiment sees. Probes can be used to make NMR, EPR and fluorescence accessible to the membrane and use fluorescent or spin-active moieties for this purpose. Clearly membranes with and without probes are not identical which makes it worthwhile to elucidate the differences between them with detailed atomistic simulations. In almost all cases these differences are confined to the local neighborhood of the probe molecules which are sparsely used and generally present as single molecules. In general, the behavior of the bulk membrane lipids can be qualitatively understood from the probes but in most cases their properties cannot be directly quantitatively deduced from the probe behavior.

show abstract

Self-Accumulation of Aromatics at the Oil−Water Interface through Weak Hydrogen Bonding

Cited by 199 publications

References 38 publications

Prediction of the water/oil interfacial tension from molecular simulations using the coarse-grained SAFT-γ Mie force field

Prediction of the water/oil interfacial tension from molecular simulations using the coarse-grained SAFT-γ Mie force field

Molecular dynamics simulations of the role of salinity and temperature on the hydrocarbon/water interfacial tension

Molecular modeling of lipid probes and their influence on the membrane

Contact Info

Product

Resources

About