Application of New Ammonium-Based Ionic Liquids for Dehydration of Crude Oil Emulsions

Abdullah, Mahmood M. S.; Sajid Ali, Mohd; Al-Lohedan, Hamad A.

doi:https://doi.org/10.1155/2023/8711570

Journal of Chemistry

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Abstract Introduction Experimental Results and Discussion Conclusion Data Availability Conflicts of Interest Authors’ Contributions Acknowledgments References Copyright Related Articles

Research Article | Open Access

Volume 2023 | Article ID 8711570 | https://doi.org/10.1155/2023/8711570

Application of New Ammonium-Based Ionic Liquids for Dehydration of Crude Oil Emulsions

Mahmood M. S. Abdullah,¹Mohd Sajid Ali,¹and Hamad A. Al-Lohedan¹

Academic Editor: Eulogio J. Llorent Mart Nez

Received30 Mar 2023

Revised26 May 2023

Accepted01 Jul 2023

Published07 Jul 2023

Abstract

Crude oil emulsions are prevalent in the petroleum industries due to different natural emulsifiers in crude oil. In addition, adding amphiphilic compounds for enhanced oil recovery at high temperatures and pressure under extreme shear stress conditions improved the stability of these emulsions. However, these emulsions are not desirable because they cause different operational problems. Herein, this work aims to synthesize and characterize two novel ionic liquids (ILs) and apply them to the dehydration of water-in-crude oil (W/O) emulsions. For that, tetraethylene glycol (TEG) was reacted with thionyl chloride (TC), yielding dialkyl halide (TEC). After that, TEC was reacted with 4-hexylaniline (HA) or 4-tetradecylaniline (TA) in the presence of sodium carbonate, obtaining the amines TC-HA and TC-TA, respectively. Finally, TC-HA and TC-TA were reacted with acetic acid, yielding the corresponding ionic liquids, THA-IL and TTA-IL. Chemical structure, surface tension (ST), interfacial tension (IFT), thermal stability, and micelle size were investigated using various techniques. The conventional bottle test was used to evaluate the performance of these ILs for dehydration W/O emulsion at different crude oil/brine ratios (ranging from 90/10 to 50/50). The results indicated that the dehydration performance (DP) increased with an increase in IL concentration. In addition, DP improved with increased water contents, reaching 100% for THA-IL and 80% for TTA-IL, respectively, at a crude oil/brine ratio of 50/50. Furthermore, TTA-IL showed higher DP and separated more clear water than THA-IL, which could be linked to its higher ability to reduce IFT due to a longer alkyl chain than THA-IL. The results showed that the synthesized ILs could serve as demulsifiers in the petroleum industry.

1. Introduction

Despite efforts being made to search for alternative energy sources for crude oil, such as solar energy, hydrogen resulting from splitting water, and wind energy, crude oil still represents one of the most significant global energy sources. In addition, crude oil is an essential resource for various petrochemical industries. Oil demand has continuously climbed during the previous 20 years, rising from 60 to 84 million barrels per day [1]. In the early years of the 21st century, global crude oil demand grew by 3.4% yearly due to the explosive expansion of consumption and industry in emerging countries such as China and India [2]. As conventional oil and gas resources have declined, unconventional resources have been promoted, developed, and utilized, particularly heavy oil and oil sands [3]. Heavy crude oil represents half of the world’s oil reserves [4]. However, heavy crude oil production transportation, storage, and refining are associated with many problems. It commonly contains higher amounts of natural emulsifiers such as asphaltene, resin, naphthenic acids, and solid particles than light and medium crude oils. These components facilitate the formation of very stable emulsions with brine [5–7]. These emulsions increase crude oil viscosity and cause corrosion in various pieces of equipment such as pipelines, pumps, and tanks. Furthermore, the ions in these emulsions poison downstream catalysts [8, 9]. Therefore, dehydration of these emulsions is crucial to avoid these issues. Various methods have been applied to dehydrate crude oil emulsions, including chemical, physical/mechanical, and biological [10, 11]. However, using chemicals is the most applicable method due to its low cost and short dehydration time [12, 13]. Surface active agents are the most common chemicals used to dehydrate crude oil emulsions. However, they have limitations, such as limited solubility under harsh conditions, e.g., high salinity, high temperature, and toxicity [14–16].

Over the past few years, ionic liquids (ILs) have received much attention for dehydrating crude oil emulsions because of their unique properties [12, 17]. Due to their ionic nature and organic components, they can work even in harsh conditions where traditional chemicals cannot function [18, 19]. In addition, they can dissolve in several organic and organic solvents [20]. The performance of ILs to dehydrate crude oil emulsion depends on the choice of the appropriate cations and anions. IL performance increases as they migrate across water/oil interfaces and reduce IFT without aggregation [21, 22].

For the synthesis of ILs in the current work, first, tetraethylene glycol (TEG) was reacted with thionyl chloride (TC), producing dialkyl halide (TEC). Following this, TEC was reacted with amines, hexylaniline (HA), or tetradecylaniline (TA), obtaining amines, TC-HA, and TC-TA, respectively. Next, TC-HA and TC-TA were quaternized with acetic acid, yielding the corresponding ionic liquids, THA-IL and TTA-IL. The yielded ILs were characterized using different techniques. Furthermore, the performance of these ILs in dehydration water-in-crude oil emulsions was investigated.

The novelty of this work is that low-cost raw materials were used to synthesize two new ammonium-based ILs under mild preparation conditions through a short route, which reduced the production cost of the obtained demulsifiers when compared with conventional demulsifiers such as poly (propylene -b- ethylene oxide). Using synthesized ILs as demulsifiers for crude oil emulsion, dehydration will significantly solve crude oil emulsion problems in the petroleum industries.

2. Experimental

2.1. Materials

Tetraethylene glycol (TEG, 99%), sodium carbonate (Na₂CO₃, ≥99.7%), dimethylformamide (DMF, 99.8%), and thionyl chloride (TC, ≥99%) were supplied by Merck Co. 4-hexylaniline (HA, 98%) and 4-tetradecylaniline (TA, 97%) were provided by Tokyo Chemical Industry Co. Acetic acid (≥99%), xylene, absolute ethanol, and 1,4-dioxane were also supplied by Merck Co.

Heavy crude oil (HCO) was supplied by Saudi Aramco Co., Riyadh, Saudi Arabia. Its API and SARA contents are 20.8°, 16.3%, 25.3%, 48.1%, 8.3%, and 0.145%, respectively. The complete specifications of HCO were reported in our earlier work [23]. Sodium chloride was dissolved in distilled water to prepare a saline solution (35 g/L).

2.2. Characterization

Fourier-transform infrared (FTIR) and nuclear magnetic resonance spectroscopies were employed to verify THA-IL and TTA-IL chemical structures. The pendant drop technique was used to investigate the surface tension (ST) and interfacial tension (IFT) of THA-IL and TTA-IL at air/water and oil/water interfaces. Thermal gravimetric analysis was conducted to investigate THA-IL and TTA-IL thermal stability. The relative solubility number (RSN) was used to evaluate the solubility properties of THA-IL and TEC-AP as follows: IL (1 g) was dissolved in 30 mL of dioxane: toluene mixture (96 : 4 vol.%). The obtained solution was treated with double distilled water until the appearance of continual turbidity; at this point, the volume of consumed water in mL equals the RSN. Dynamic light scattering (DLS) was utilized for measuring the micelle size (MS) and polydispersity index (PDI).

2.3. Preparation of W-in-HCO Emulsions

Water-in-HCO emulsions were prepared as reported in our earlier work [7]. Briefly, different ratios of crude oil/saline solution (90/10, 70/30, and 50/50) were mixed using a homogenizer at 4000 rpm for 20 min.

2.4. Dehydration of W-HCO Emulsions

The dehydration of W-HCO emulsions was tested using the conventional bottle test method as follows: the freshly prepared emulsions were transferred to quick-fit cylinders (25 mL), injected with a suitable dose of IL solution (500 mg dissolved in 2 mL of xylene/ethanol volumetric ratio 75/25) via a micropipette, closed, shaken 100 times on an oscillating shaker, and placed in a hot water bath (60°C). The following equation was used for dehydration performance (DP%) calculation:where DW is a volume of dehydrated water and EW is a volume of emulsified water.

2.5. Synthesis of THA-IL and TTA-IL

An excess amount of TC was added to TEG (10 g, 51.49 mmol.) gradually at 30°C for 1 h, followed by reflux for 4 h. Then, the excess amount of TC was evaporated under reduced pressure to produce dialkyl chloride (TEC). Following this, a mixture of TEC (28.2 mmol.) and Na₂CO₃ (1.5 g) with HA or TA (28.2 mmol.) was dissolved in 20 mL of dimethylformamide and stirred at ambient temperature for 5 h. Dimethylformamide was evaporated using a rotary evaporator, and the mixture was dissolved in 2-propanol. The produced solution was filtered, followed by the evaporation of 2-propanol, yielding the corresponding amines, TC-HA and TC-TA. Ionic liquids, THA-IL and TTA-IL, were obtained from reacting amines, TC-HA and TC-TA, respectively, with a stoichiometric ratio of acetic acid. Scheme 1 presents the synthesis route for THA-IL and TTA-IL.

A schematic illustration of the synthesis, characterization, and application of THA-IL and TTA-IL in the dehydration of W-HCO emulsions is presented in Figure 1.

3. Results and Discussion

3.1. Chemical Structures of THA-IL and TTA-IL

Figures 2(a), 2(b), 3(a), and 3(b) present the chemical structures of THA-IL and TTA-IL verified using FTIR and ¹H-NMR. In FTIR spectra (Figures 2(a) and 2(b)), the stretching absorption band of aromatic C-H appeared at 3050 cm⁻¹ [24]. In contrast, the stretching absorption bands of saturated aliphatic C-H appeared at around 2925 cm⁻¹ and 2850 cm⁻¹ [25]. The stretching bands of the aromatic double band (C=C) occurred between 1620 cm⁻¹ and 1500 cm⁻¹ [26]. The bending absorption band of aliphatic C-H was observed at 1465 cm⁻¹. The stretching bands of C-O-C were noticed at around 1124 cm⁻¹ [27]. In ¹H-NMR spectra (Figures 3(a) and 3(b)), the protons of the alkyl chain were observed between 0.75 and 2.6 ppm, as indicated in the figure. The methyl protons of CH₃COO⁻ were noticed at 1.85 ppm [28], while the protons of TEC were noticed at 3.4 ppm and 3.65 ppm [29]. The proton of aromatic rings resonated at 7.05 ppm and 7.25 ppm [30], whereas the protons of quaternized amine appeared at 7.85 ppm [31].

(a)

(b)

(a)

(b)

3.2. Thermal Stability of THA-IL and TTA-IL

The thermal stability of THA-IL and TTA-IL was evaluated using TGA, as shown in Figure 4. The decomposition of THA-IL and TTA-IL seems similar, which could be due to their similar chemical structure. The decomposition up to 150°C is caused by the loss of physisorbed water [32]. The primary decomposition for both ILs occurred between 150 and 450°C, which could be referred to as the degradation of the alkyl chains and oxyethylene units. The slight increase in thermal stability of THA-IL can be attributed to its structure containing shorter alkyl chains than TTA-IL [33].

3.3. Surface Activity of THA-IL and TTA-IL

The surface activity is an essential parameter for demulsifier selection, where its molecules can migrate through a continuous phase, reaching the crude oil/brine interface and replacing the naturally occurring rigid film. This replacement facilitates the coagulation of water droplets, leading to emulsion dehydration [7, 34, 35]. A pendant drop technique was used to measure the ST and IFT of THA-IL and TTA-IL at air/water and oil/water interfaces. This technique is one of the primary and most feasible methods for measuring IFT [36]. Figure 5 shows ST against the natural logarithm of THA-IL and TTA-IL concentrations. ST decreases as concentrations increase, reaching critical micelle concentration (CMC). After that, ST remains constant with increasing IL concentrations, indicating micelle formation. THA-IL and TTA-IL surface activity parameters are shown in Table 1. The surface excess concentration () and the minimum surface area occupied per molecule are used to indicate surface-active compounds’ behavior. Gibbs adsorption isotherm equations were used to calculate these parameters:where R is the general gas constant, T is the measurement temperature in Kelvin, is the straight line slope in Figure 5, and N is Avogadro’s constant. The lower CMC value of TTA-IL shows its lower solubility in water than THA-IL, which could be ascribed to its chemical structure, where it has longer alkyl chains than THA-IL [14, 34]. The higher value and the lower value of TTA-IL confirm its greater tendency to self-assemble at the air/water interface than in bulk aqueous solution. These data also indicated that TTA-IL molecules could pack themselves tighter than THA-IL molecules [37, 38]. Table 1 also presents the RSN values for THA-IL and TTA-IL. The RSN values indicated the solubility of amphiphilic compounds in aqueous and organic solvents, where a value > 17 indicates the solubility of a compound in water, and as the value increases, the solubility of the compound in water increases. The low RSN value <13 demonstrates compound solubility in organic solvents [39]. The higher RSN value of THA-IL confirmed its higher solubility in water than that of TTA-IL, which could be linked to short alkyl chains compared with TTA-IL. These data are compatible with CMC values.

The DLS technique was used for measuring MS and PDI of THA-IL and TTA-IL in bulk aqueous solutions. Figures 6(a) and 6(b) show the DLS histograms of THA-IL and TTA-IL. The MS and PDI were 388.2 nm and 0.072 for THA-IL and 457.5 nm and 0.053 for TTA-IL, respectively. In both ILs, the MS and PDI values are low, indicating that they form uniform micelles [40]. Furthermore, a decrease in the MS value of THA-IL indicates its tighter packing than in TTA-IL.

(a)

(b)

However, nonionic surfactants are commonly used as additives to reduce IFT; their performance is affected significantly under harsh conditions, e.g., high salinity and high pressure [28, 41]. The synthesized ILs can act as nonionic surfactants due to the presence of oxyethylene units and alkyl chains. Moreover, these ILs can work even under harsh conditions due to their ionic nature. The IL ions can neutralize salts’ ions, leading to their molecule accumulation at the oil/water interface, decreasing IFT [22]. In this respect, the IFT at the crude oil/brine interface was measured, as presented in Table 2. THA-IL and TTA-IL showed efficient performance in reducing IFT, where their performance increased as their concentrations increased. THA-IL and TTA-IL reduced IFT at this interface from 33.5 mN//M to 4.2 mN//M and 3.6 mN//M at 1000 ppm, respectively. The data indicated that TTA-IL showed higher relative IFT reduction performance, which is due to a longer alkyl chain than that of THA-IL, where increasing the alkyl chain length improves the accumulation of IL molecules at the crude oil/brine interface, thus reducing IFT [42].

3.4. Dehydration Performance of THA-IL and TTA-IL

However, poly (propylene -b- ethylene oxide) copolymers are one of the most applied demulsifiers for crude oil dehydration [43]; they have some drawbacks, e.g., high production cost and low performance under harsh conditions [44]. This work focused on synthesizing two novel ILs under mild synthesis conditions through a short route. Their dehydration performance was evaluated using the conventional bottle test at 60°C, as reported in the Experimental section. The type of prepared emulsion was confirmed using the drop dilution method. The dispersion of all prepared emulsions in low polar organic solvents, e.g., toluene and chloroform, with no dispersion in water, confirmed the formation of water-in-oil (W/O) emulsions. The stability of the prepared emulsions was tested by dealing with the blank samples at the same sample condition except for the addition of IL. The blank samples were placed in a hot water bath (60°C). These samples showed no separation for a couple of weeks, indicating the stability of the prepared emulsions. Figure 7(a) illustrates the microscopy photo of blank emulsion droplets after two weeks with an average diameter of 2 µ, indicating these emulsions’ stability. Table 3 shows the dehydration performance (DP) of THA-IL and TTA-IL and dehydration time (DT) for various W/O emulsion ratios at 60°C.

(a)

(b)

(c)

The data show that the DP increased as the THA-IL and TTA-IL concentrations increased. Moreover, the DT decreased as the concentration increased. Figures 8(a)–8(c) display the DP of TTA-IL at different concentrations versus DT. The data showed increased DP and DT as the crude oil ratio decreased. Increasing the IL concentration in W-HCO emulsion enhances the number of its molecules adsorbed at a crude oil/brine interface, weakening and rupturing the asphaltene and resin natural film, thus facilitating water droplet coalescence.

(a)

(b)

(c)

However, THA-IL and TTA-IL exhibited high DP; they take long dehydration time compared to conventional demulsifiers, which could be linked to their ionic nature, where their presence in ionic form obstructs their diffusion in a continuous phase (crude oil) [12].

Due to an environmental issue, selecting an effective demulsifier for dehydrating clean water is essential when the obtained water is disposed of in the environment [12]. Figures 9(a) and 9(b) show optical images of dehydrated water using THA-IL and TTA-IL in different concentrations at a crude oil/brine ratio 50/50. As depicted in Figure, THA-IL and TTA-IL can dehydrate clean water. However, TTA-IL succeeded in dehydrating more clean water than THA-IL, which may be due to its higher ability for IFT reduction than THA-IL due to the presence of a longer alkyl chain than that of THA-IL [14]. These results suggest that TTA-IL can be effectively applied to dehydrate clean water in the petroleum industry.

(a)

(b)

3.5. Dehydration Mechanism

The dehydration mechanism of crude oil emulsions using ILs occurs via two main steps: diffusion of IL in the continuous phase followed by adsorption of IL molecules at the oil/water interface [45, 46]. In W/O emulsions, the diffusion of IL in crude oil as a continuous phase takes a long time due to the ionic nature of ILs obstructing their dispersion in crude oil. The number of molecules adsorbing at the crude oil/brine interface increases as IL concentrations increase. The adsorption of these IL molecules at this interface occurs due to their orientation, where the hydrophilic part is oriented toward brine. In contrast, the lipophilic part is oriented toward crude oil. As a result, the hydrophilic and hydrophobic parts interact with crude oil components and water molecules via different interactions. These interactions include hydrogen bonding between oxyethylene units in IL and those in natural asphaltene and resin films. In addition, these interactions include Van der Waals and π-π stacking between alkyl chains and phenyl rings of ILs and corresponding in asphaltene rigid films [47]. These interactions neutralize the imbalanced forces between water and crude oil phases and result in IFT reduction (Table 2), thus facilitating asphaltene interfacial film rupture and water droplet coalescence.

Furthermore, the interaction of IL ions with the opposite salt ions (in the brine) reduces the repulsion of IL molecules at the crude oil/brine interface, and thus, it facilitates IL molecule accumulation at this interface [22]. Such interactions reduce IFT and facilitate IL molecules’ penetration into the asphaltene rigid film. When IL molecules penetrate this rigid film, they change their chemical properties, disrupting and softening it and encouraging its replacement. The replacement of this film destabilizes the emulsion droplets, allowing water droplet coalescence. Figures 7(b) and 7(c) show microscopic photos of an emulsion containing TTA-IL 500 ppm after 2 and 3 hrs. The figure illustrates how the emulsion droplet size increased over time due to the coalescence of tiny water droplets into a larger one.

4. Conclusion

Two novel ILs were synthesized and applied to W/O emulsions dehydration. First, TEG was converted to dialkyl halide (TEC) using TC. Following this, TEC was reacted with HA or TA to obtain the corresponding amines, TC-HA and TC-TA. Next, ILs, THA-IL and TTA-IL, were obtained by reacting TC-HA or TC-TA with a stoichiometric ratio of acetic acid. Then, the synthesized ILs, THA-IL and TTA-IL, were characterized using FTIR, ¹H-NMR, TGA, and DLS. For crude oil emulsion dehydration, surface activity is crucial. The surface activity parameter showed that THA-IL and TTA-IL exhibited efficient ST and IFT reductions. Moreover, TTA-IL showed higher performance than THA-IL, possibly due to longer alkyl chains of TTA-IL than those of THA-IL.

Thanks to the surface activity of THA-IL and TTA-IL, their performance in the dehydration of W/O emulsions was investigated. Both ILs showed significant performance in crude oil emulsion dehydration. Their performance improved with concentration. Furthermore, TTA-IL displayed higher DP and shorter DT than THA-IL, possibly due to the longer alkyl chains of TTA-IL that increase diffusion into a continuous phase (crude oil). The first step in dehydration involves IL diffusion, followed by adsorption at the oil/water interface. Due to their ionic nature, IL diffusion in crude oil can take a long time. However, alkyl chains and aromatic rings in synthesized ILs facilitate their diffusion in crude oil. The adsorption of THA-IL and TTA-IL at the oil/water interface occurs via different interactions, including hydrogen bonding, van der Waals, π-π stacking, and electrostatic interactions. These interactions weaken the asphaltene rigid film and facilitate its replacement allowing water droplet coalescence.

Data Availability

All data were included in the manuscript.

Conflicts of Interest

The authors declare that they have no conflicts of interest.

Authors’ Contributions

Mahmood M. S. Abdullah investigated the study, proposed the methodology, conceptualized the study, wrote the original draft, and wrote, reviewed, and edited the manuscript. Mohd Sajid Ali investigated the study and reviewed and edited the manuscript. Hamad A. Al‐Lohedan proposed the methodology, conceptualized the study, and was responsible for resources.

Acknowledgments

The authors acknowledge the financial support through Researchers Supporting Project number (RSPD2023R688), King Saud University, Riyadh, Saudi Arabia.

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Copyright © 2023 Mahmood M. S. Abdullah et al. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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