Synthesis and characterization of imidazolium asphaltenes poly (ionic liquid) and application in asphaltene aggregation inhibition of heavy crude oil

El‐Hefnawy, Mohamed E.; Atta, Ayman M.; El‐Newehy, Mohamed H.; Ismail, Ali I.

doi:10.1016/j.jmrt.2020.10.038

Cited by 24 publications

(19 citation statements)

References 45 publications

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“…Major disadvantages of this process are asphaltene precipitation, wax deposition and gas hydrate formation. According to recent studies, ionic liquids have the capacity to control asphaltene precipitation, wax deposition and they act as methane gas hydrate inhibitors [31].…”

Section: Crude Oil Industrymentioning

confidence: 99%

Ionic liquids as alternative solvents for energy conservation and environmental engineering

2021

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Because of industrialization and modernization, phenomenal changes have taken place in almost all spheres of life. Consequently, the consumption of energy resources and the cases of environmental hazards have risen to an unprecedentedly high level. A development model with due consideration to nature and an efficient utilization of energy sources has become the need of the hour, in order to ensure a sustainable balance between the environmental and technological needs. Recent studies have identified the suitability of ionic liquids (ILs), often labeled as ‘green solvents’, in the efficient utilization of energy resources and activities such as bio-extraction, pollution control, CO2 capture, waste management etc. in an environmentally friendly manner. The advent of magnetic ionic liquids (MILs) and deep eutectic solvents (DESs) have opened possibilities for a circular economic approach in this filed. This review intends to analyze the environmental and energy wise consumption of a wide variety of ionic liquids and their potential towards future.

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Section: Crude Oil Industrymentioning

confidence: 99%

Ionic liquids as alternative solvents for energy conservation and environmental engineering

2021

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“…They reported that the aromatic ILs served as an asphaltene dispersing agent more than the aliphatic ILs. 33 Elhoshoudy et al used halogenated alkyl imidazolium ILs and their combination with Lewis acid as asphaltene dispersants. They found that hydrogen bonding and electrostatic interactions were the main forces for the dispersing ability of these ILs.…”

Section: Introductionmentioning

confidence: 99%

“…El-Hefnawy et al investigated the effect of ILs produced by the oxidation of asphaltene alkyl side chains on the dispersion of asphaltenes. They reported that the aromatic ILs served as an asphaltene dispersing agent more than the aliphatic ILs . El-hoshoudy et al used halogenated alkyl imidazolium ILs and their combination with Lewis acid as asphaltene dispersants.…”

Section: Introductionmentioning

confidence: 99%

Investigation on Asphaltene Dispersion Activity of Tetrabutylammonium Carboxylate Ionic Liquids

et al. 2023

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Asphaltene destabilization is still known as one of the main problems of the petroleum industry and imposes many costs on this industry during crude oil production, transportation, and refining. The most important solution to control this problem is using chemical compounds to disperse asphaltene aggregates. Ionic liquids, as an emerging industrial solvent and catalyst, have been used for this purpose in the last two decades. In this work, three ionic liquids having a tetrabutylammonium cation and oleate, stearate, and cinnamate anions were synthesized and used as asphaltene dispersants. The efficiency of the synthesized ionic liquids on the stability of asphaltene aggregates was investigated using cluster size, polydispersity index, zeta potential, and ultraviolet spectroscopy data. It was found that tetrabutylammonium cinnamate and tetrabutylammonium oleate (dispersion indices of 82.5 and 60.2, respectively) have a much higher efficiency than tetrabutylammonium stearate (dispersion index of 20.6). The results of cluster size, polydispersity index, and zeta potential analysis were confirmed by ultraviolet spectroscopy and optical microscopy data. For instance, the mean radius of asphaltene clusters was 2179.8 nm, reduced to 253, 680, and 1402 nm after adding tetrabutylammonium salt of cinnamate, oleate, and stearate, respectively. The same trend was observed in the results of the polydispersity index (0.417, 0.470, and 0.624) and zeta potential analysis (31.4, 1.81, and −0.56). The cinnamate, oleate, and stearate anions have four, one, and no carbon−carbon π bonds, respectively. It seems that the presence of π bonds that can form π−π interactions with π bonds of the asphaltene molecules is an essential factor in asphaltene stabilization by these ionic liquids. In addition, the results showed that the higher the net negative charge of the anion, the greater the ability of the anion to stabilize asphaltene aggregates. This stabilization, which was mainly done through electrostatic interactions between polar groups of asphaltene and the carboxylate anions, was confirmed by zeta potential data.

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“…EL-Hefnawy et al 26 functionalized asphaltenes with carboxylic acid groups to incorporate them into functional imidazolium ILs by conjugating asphaltene carboxylate anions with 1,3-diheptyl (aliphatic - AsIL) and 1,3-diheptyl-2-hydroxyphenyl (aromatic - AHIL) imidazolium cations. The interactions between pure IL and asphaltenes in different compositions of toluene/heptane binary mixture were studied by dynamic light scattering (DLS) and zeta potential measurements to evaluate the dispersion of asphaltenes and charge transfer between the IL and asphaltene heteroatoms, respectively.…”

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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Synthesis and characterization of imidazolium asphaltenes poly (ionic liquid) and application in asphaltene aggregation inhibition of heavy crude oil

Cited by 24 publications

References 45 publications

Ionic liquids as alternative solvents for energy conservation and environmental engineering

Ionic liquids as alternative solvents for energy conservation and environmental engineering

Investigation on Asphaltene Dispersion Activity of Tetrabutylammonium Carboxylate Ionic Liquids

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

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