Synthesis and application of geminal dicationic ionic liquids and poly (ionic liquids) combined imidazolium and pyridinium cations as demulsifiers for petroleum crude oil saline water emulsions

Atta, Ayman M.; Al‐Lohedan, Hamad A.; Ezzat, Abdelrahman O.

doi:10.1016/j.molliq.2020.115264

Cited by 30 publications

(11 citation statements)

References 54 publications

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“…The presence of natural emulsifiers, such as asphaltenes, resins, and solid particles, as constituents in crude oil composition aids in the formation of stable crude oil emulsions with formation water during crude oil production [ 1 , 2 ]. In addition, the added amphiphilic chemicals such as surfactants during enhanced oil recovery, along with a high shear rate at reservoir conditions (high pressure and high temperature), enhances the stability of the formed crude oil emulsions [ 2 , 3 ]. The presence of crude oil in emulsion form leads to several operational issues, e.g., an increased crude oil viscosity, making its transportation very difficult, the corrosion of different equipment such as tanks, pipelines, and pumps, as well as the poisoning of catalysts during the refining process due to the presence of salts in the formation water.…”

Section: Introductionmentioning

confidence: 99%

“…ILs are organic salts with low vapor pressure, high thermal stability, a low melting point (below 100 °C), and low toxicity. AILs have a great tendency to reduce the interfacial tension between crude oil and water even in harsh conditions; they disperse the asphaltenes’ interfacial film surrounding the water droplets, leading to phase separation [ 3 , 20 ].…”

Section: Introductionmentioning

confidence: 99%

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New Amphiphilic Ionic Liquids for the Demulsification of Water-in-Heavy Crude Oil Emulsion

et al. 2022

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This work aimed to use abietic acid (AA), as a widely available natural product, as a precursor for the synthesis of two new amphiphilic ionic liquids (AILs) and apply them as effective demulsifiers for water-in-crude oil (W/O) emulsions. AA was esterified using tetraethylene glycol (TEG) in the presence of p-toluene sulfonic acid (PTSA) as a catalyst obtaining the corresponding ester (AATG). AATG was reacted with 1-vinylimidazole (VIM) throughout the Diels–Alder reaction, forming the corresponding adduct (ATI). Following this, ATI was quaternized using alkyl iodides, ethyl iodide (EI), and hexyl iodide (HI) to obtain the corresponding AILs, ATEI-IL, and ATHI-IL, respectively. The chemical structure, surface activity, thermal stability, and relative solubility number (RSN) were investigated using different techniques. The efficiency of ATEI-IL and ATHI-IL to demulsify W/O emulsions in different crude oil: brine volumetric ratios were evaluated. ATEI-IL and ATHI-IL achieved promising results as demulsifiers. Their demulsification efficiency increased as the brine ratios decreased where their efficiency reached 100% at the crude oil: brine ratio (90:10), even at low concentrations.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

New Amphiphilic Ionic Liquids for the Demulsification of Water-in-Heavy Crude Oil Emulsion

et al. 2022

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“…[1,2] Therefore, in the process of oil production, in order to improve the oil recovery rat, a series of stimulation measures such as alkaline water, fracturing and polymer flooding are often adopted, [3,4] which lead to the continuous increase of water content of heavy oil produced liquid. [5] Water in crude oil emulsion can corrode pipelines and equipment during transportation, [6] and easily lead to catalyst deactivation in petroleum processing. [7] Therefore, demulsification and removal of water from crude oil are of great significance.…”

Section: Introductionmentioning

confidence: 99%

“…[8][9][10][11][12][13][14] At present, chemical demulsification is the most commonly used demulsification method. [15][16][17] The chemical demulsifier is a kind of surfactant. Adding a small amount to the crude oil will make the interface properties unstable, break the kinetic and thermodynamic equilibrium, rapidly and rapidly induce the fusion of droplets, so that water can be separated from the crude oil.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Research of Highly Efficient Polyether Demulsifier

2022

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Separation of oil and water has always been a top priority in the oil industry. In this study, bisphenol A phenolamine resin (BPA) was synthesized from bisphenol A, diethylenetriamine and formaldehyde. With KOH as a catalyst, the initiator, ethylene oxide (EO) and propylene oxide (PO) were polycondensed into triblock polyethers with different molecular weights, and then crosslinked to increase the molecular weight. The target product was determined by 1 HNMR and FT-IR, and the synthesis process of triblock polyether demulsifier was optimized by changing the ratio of initiator to head PO, PO to EO and head PO to tail PO. Then, the important influential factors for the demulsification such as the demulsifier concentration, standing time, temperature, pH and Hydrophile-lip-ophile balance (HLB) values were investigated. The results suggestted that the optimal synthesis ratio of BPA type triblock polyether demulsifier was as follows: initiator/PO = 1 : 109, PO/ EO = 2 : 1, head PO/ tail PO = 1 : 3. Under demulsification conditions, the dehydration temperature was 50 °C, the dosage was 75 mg ⋅ L À 1 , pH was 7.6 and HLB was 9.1, and the dehydration rate reached 92.5 % in 90 minutes. Compared with the existing demulsifier, the demulsifier has a lower demulsification temperature and higher demulsification efficiency. Therefore, it can be concluded that the polyether demulsifier has potential application for the crude oil dehydration, and the current work may be helpful to explore the demulsification development.

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“…Numerous studies elucidating the effectiveness of ILs for demulsification activity of water/oil separation have been reported in the literature. − Pyridinium is a new class of ILs with unique features and has been tested for many scientific applications. − Specifically, pyridinium ILs are attracting considerable attention as demulsifying chemicals for stable emulsions. Recently, Atta et al synthesized novel geminal dicationic ILs composed of pyridinium and imidazolium cations for the purpose of demulsifying heavy emulsions produced from seawater and crude oil. The result of their study showed that the pyridinium ILs brought about water/oil separation using a range of concentrations (100–250 ppm), and the demulsification activity was completed within a short period.…”

Section: Introductionmentioning

confidence: 99%

Demulsification of Heavy Petroleum Emulsion Using Pyridinium Ionic Liquids with Distinct Anion Branching

et al. 2021

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The challenges associated with heavy crude oil emulsions during hydrocarbon exploitation cannot be overemphasized. As such, water/crude oil separation in oil fields becomes necessary before conveyance to the refinery. In this study, we investigated new classes of pyridinium ionic liquids (ILs) demulsifiers, 1-butyl-4-methylpyridinium tetrafluoroborate, 1-butyl-4-methylpyridinium hexafluorophosphate, and 1-butyl-4-methylpyridinium iodide, designated as BMPT, BMPH, and BMPI, with unique anions (BF4 –, PF6 –, and I–), respectively. The effects of concentration dosages (100–1000 ppm) and anions of these ILs on the demulsification of produced emulsions were assessed using the bottle test technique at 75 °C. Viscosity and shear stress determination as well as interfacial tension (IFT) measurements were applied to affirm the effectiveness of these ILs to separate water/oil into phases. Bottle test results revealed that BMPT, BMPH, and BMPI demulsifiers removed water from the emulsion effectively, and the demulsification efficiency (% DE) increased with increasing dosage. BMPT, BMPH, and BMPI achieved the best % DE of 84%, 99%, and 59%, respectively, at 1000 ppm after 60 min. The highest water separation was recorded in PF6 – anion because of its high hydrophobic nature. Viscosity and shear stress time-sweep measurements indicated the reduction in viscosities and shear stresses after injection of the demulsifiers. Also, the dynamic IFT results showed that these demulsifiers could mix with water–oil at the interface, break asphaltenes and resins molecules, and reduced the IFT from 16.01 to 12.47 mN/m. Optical microscopic emulsion images before and after demulsifier injection and the demulsification mechanism describing the water/oil separation stages are also discussed.

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Synthesis and application of geminal dicationic ionic liquids and poly (ionic liquids) combined imidazolium and pyridinium cations as demulsifiers for petroleum crude oil saline water emulsions

Cited by 30 publications

References 54 publications

New Amphiphilic Ionic Liquids for the Demulsification of Water-in-Heavy Crude Oil Emulsion

New Amphiphilic Ionic Liquids for the Demulsification of Water-in-Heavy Crude Oil Emulsion

Synthesis and Research of Highly Efficient Polyether Demulsifier

Demulsification of Heavy Petroleum Emulsion Using Pyridinium Ionic Liquids with Distinct Anion Branching

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