Investigation the effect of different ionic liquids based-aryl imidazole on the onset precipitation of asphaltene

Abstract

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.

Evaluation of ionic liquids based imidazolium salts as an environmentally friendly corrosion inhibitors for carbon steel in HCl solutions

“…The resultant spectrum was compared to the FT-IR spectrum of the R 10 -IL. The R 10 -IL constitutes of benzene unit, imidazole ring and alkyl chain 30 . The FT-IR spectrum of vacuum dried R 10 -IL is shown in Fig.…”

“…NMR spectra ( 1 H-NMR and 13 C-NMR) for the studied ILs; R 8 -IL, R 10 -IL, and R 12 -IL were investigated on a BRUKER NMR Spectrometer at frequency equal at 400 MHz and showed a similarity in the chemical shifts for the three ionic liquids. 1 H-NMR spectroscopy were discussed in the previous work as shown before 30 . 13 C-NMR (DMSO-d6) ppm for R 8 -IL, R 10 -IL, and R 12 -IL were expressed in Figs.…”

“…Three different ionic liquids (ILs) were prepared according to the method described elsewhere, as shown in Fig. 1 , 30 . The synthesis method, in brief, was conducted by refluxing an equivalent amount of 1-(chloromethyl)-4-methylbenzene and 1-alkyl imidazole derivatives containing different alkyl chains for 6 h at 80 °C to produce 3-(4-methylbenzyl)-1-octyl-1-H-imidazolium chloride, 3-(4-methylbenzyl)-1-Decyl-1-H-imidazolium chloride, and 3-(4-methylbenzyl)-1-dodecyl-1-H-imidazolium chloride.…”

Experimental and computational studies of novel cyclic ammonium based ionic liquids as corrosion inhibitors for carbon steel in acid medium

“…Non-toxic corrosion inhibitors are desperately needed because organic traditional inhibitors have a negative impact on the surrounding environment. Biopolymers, surfactants, amino acids, natural products, lanthanides and ionic liquids (ILs) 21 – 25 , all are proposed as novel environmentally benign corrosion inhibitors. ILs are made up of ions, normally melts at ambient temperatures (below 100 °C).…”

Research Progress in Nanoparticle Inhibitors for Crude Oil Asphaltene Deposition

“…The inhibitors based on ionic liquids exhibit remarkably low vapor pressure, a low melting point, excellent thermal stability, non-flammability, and favorable solubility in various solvents. However, the production scale and intricate synthesis mechanism of these ionic liquids render them more costly compared with commercially available asphaltene inhibitors [ 26 , 27 , 28 ]. Moreover, compared with traditional organic asphaltene inhibitors (such as sodium dodecyl benzene sulfonate and phenol), it has significant advantages.…”