With the projected increase in the production of heavy oil due to the energy crisis, asphaltene-related issues are likely to come to the forefront. This leads to operational problems, safety hazards, and oil production deficiencies, resulting in huge economic losses for the petroleum industry. Therefore, in this work, we aimed to inhibit asphaltene precipitation using ionic liquid (IL) compounds. ILs with long alkyl chains can inhibit the precipitation of asphaltene molecules due to the π–π* interactions between them and the formation of hydrogen bonds. A series of imidazolium-based ionic liquids, IL-0, IL-4, IL-10, and IL-16, were synthesized with yield percents of 79, 81, 80, and 83%, respectively. The prepared materials were characterized well using FTIR, 1H-NMR, and Elemental Analysis. The surface tension, interfacial tension (IFT), and different surface parameters were investigated at different temperatures to simulate the reservoir temperature. IL-0, IL-4, IL-10, and IL-16 displayed their γcmc values at 35, 34, 31, and 32 mN/m at 303 °K, respectively. It was found that the prepared ILs are good surfactants with low values of interfacial tension. Quantum structure–activity relationships using Density Functional Theory (DFT) were used to investigate the geometry optimization electronic structures, the energy gap (ΔE), and the reactivity of the cations of the prepared ILs. The synthesized ILs were evaluated as asphaltene dispersants using two different techniques. The viscometric technique showed that the asphaltene onset precipitation was 28.5 vol.%. This percent was postponed to 42.8, 50, 78.5, and 64.3 vol.%, after adding IL-0, IL-4, IL-10, and IL-16, respectively, and the spectroscopic technique confirmed the results.

Precipitation and deposition of asphaltene are considered as catastrophic issues facing the petroleum industry. Asphaltene deposition mainly occurs at variety places such as formation pore spaces, pumps, pipelines, wellbore, wellhead, tubing, surface facilities and safety valves causing operational problems, production deficiencies and enormous economic losses. This work aims to study the effect of series of synthesized aryl ionic liquids (ILs) containing different alkyl chains, named as R8-IL, R10-IL, R12-IL, and R14-IL, on the onset precipitation point of asphaltene in crude oil. R8-IL, R10-IL, R12-IL, and R14-IL were synthesized with high yields (the yield varied between 82 and 88%) and characterized via different tools of analysis (FTIR, 1H NMR, and Elemental Analysis). Their Thermal Gravimetric Analysis (TGA) was investigated and showed a reasonable degree of stability. It was found that R8-IL (short alkyl chain) has the highest stability, while R14-IL (long alkyl chain) is the lowest one. Quantum chemical calculations were conducted to study the reactivity and geometry of their electronic structures. Moreover, surface and interfacial tension of them were studied. It was found that the efficiency of the surface active parameters increased by increasing the length of the alkyl chain. The ILs were evaluated to delay the onset precipitation point of asphaltene using to different methods; the kinematic viscosity and the refractive index. Results from the two methods showed delaying of onset precipitation after the addition of the prepared ILs. The asphaltene aggregates was dispersed due to the π–π* interactions and hydrogen bonds formation with the ILs.

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Heavy and extra heavy oil exploitation has attracted attention in the last few years because of the decline in the production of conventional crude oil. The high viscosity of heavy crude oil is the main challenge that obstructs its extraction. Consequently, catalytic aquathermolysis may be an effective solution to upgrade heavy crude oil to decrease its viscosity in reservoir conditions. In this regard, a series of acidic ionic liquids, 1-butyl-1H-imidazol-3-ium 4-dodecylbenzenesulfonate (IL-4), 1-decyl-1H-imidazol-3-ium 4-dodecylbenzenesulfonate (IL-10), and 1-hexadecyl-1H-imidazol-3-ium 4-dodecylbenzenesulfonate (IL-16), were utilized in the aquathermolysis of heavy crude oil. Of each IL, 0.09 wt % reduced the viscosity of the crude oil by 89%, 93.7%, and 94.3%, respectively, after the addition of 30% water at 175 °C. ILs with alkyl chains equal to 10 carbon atoms or more displayed greater activity in viscosity reduction than that of ILs with alkyl chains lower than 10 carbon atoms. The molecular weight and asphaltene content of the crude oil were decreased after catalytic aquathermolysis. The compositional analysis of the crude oil before and after catalytic aquathermolysis showed that the molar percentage of lighter molecules from tridecanes to isosanes was increased by 26–45%, while heavier molecules such as heptatriacontanes, octatriacontanes, nonatriacontanes, and tetracontanes disappeared. The rheological behavior of the crude oil before and after the catalytic aquathermolytic process was studied, and the viscosity of the crude oil sample was reduced strongly from 678, 29.7, and 23.4 cp to 71.8, 16.9, and 2.7 cp at 25, 50, and 75 °C, respectively. The used ILs upgraded the heavy crude oil at a relatively low temperature.

The disastrous consequences for society—economically, environmentally, and socially—caused by oil spills encouraged us to treat this problem. The target of this work is to synthesize new amphiphilic dicationic ionic liquids (Ia, Ib, and Ic) and evaluate them spectroscopically and gravimetrically as potential oil spill dispersants at different temperatures to cover cold and warm areas. The synthesized ILs were well characterized by different tools for analysis of their surface activity and thermal stability. Ia, Ib, and Ic showed good dispersion effects, which were recorded to be 5.32, 20.45, and 33.61% for Ia, Ib, and Ic, respectively, at 10 °C and 12.28, 52.55, and 66.80% for Ia, Ib, and Ic, respectively, at 30 °C with a dispersant-to-oil ratio (DOR) of 0.8:10 (wt.%). Acute toxicity tests were elucidated against Nile tilapia and Oreochromis niloticus fish and confirmed their slight toxicity by determining a LC50 value greater than 100 ppm after 96 h, which recorded 13.25, 17.75, and 37.5 mg/L for Ia, Ib, and Ic, respectively. Overall, the new synthesized ILs can be represented as sustainable materials for toxic chemicals to disperse oil spills.