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![The synthesis of N-substituted pyrroles catalyzed by [hmim][HSO4].](publication/258401320/figure/fig1/AS:324334599065609@1454338802402/The-synthesis-of-N-substituted-pyrroles-catalyzed-by-hmimHSO4_Q320.jpg)
A new procedure to synthesize the N-substituted pyrrole derivatives by Clauson Kaas reaction catalyzed by acidic ionic liquid under microwave irradiation was developed. This procedure provides several advantages such as high yield, clean product formation, and short reaction time.
Citations
... This adsorption significantly reduces the interfacial tension, and changes the wettability between crude oil and reservoir rock surface. The surfactants facilitate the formation of stable oil-in-water (O/W) emulsion with low viscosity, enabling easier flow through reservoir rock pores and ultimately leading to enhanced oil recovery [12][13][14]. However, in practical applications, surfactants can be deactivated in acidic environments, and lose their effective concentration due to adsorption on the rock surfaces [15][16][17]. ...
Oil is a critical raw material for energy and industry, the depletion of conventional oil reserves necessitates efficient extraction and production of unconventional resources like acidic crude oil. However, its high viscosity poses significant challenges for transportation and processing. To address these challenges, this study developed a novel emulsion viscosity reducer. We designed a nanofluid based on a synergistic polyetheramine/nanofluid system consisting of alkyl ethoxy polyglycosides (AEG) as a green surfactant, SiO 2 nanoparticles, and an organic alkali polyetheramine. The mixture was evaluated for its viscosity reduction and emulsification performance with acidic crude oi obtained from Qinghe oil production plant in Shengli Oilfield. The results showed that the optimized viscosity reducer achieved a remarkable reduction rate of 98.1% at 50◦C in crude oil viscosity from 6862 mPa·s to 129 mPa·s. This demonstrated the reducer effectively transformed acidic crude oil into a low viscosity oil-in-water (O/W) emulsion with high stability. Furthermore, the core imbibition simulation tests demonstrated that the viscosity reducer could improve the recovery of acidic crude oil from 29.6% to 49.4%, indicating the potential application of the optimized viscosity reducer in the exploitation of acidic crude oil. In conclusion, this study developed a novel emulsion viscosity reducer, which can reduce the viscosity and improve recovery of acidic crude oil by emulsifying into O/W emulsion. The optimized formula has potential for practical application in the exploitation of acidic crude oil.
... At the same time, microwave heating results in an order of magnitude improvement in the separation time. The study by Martínez-Palou et al. 6 showed that with the increase of microwave power, the demulsification efficiency was improved. However, the application of microwave demulsification alone often fails to meet the standard of dehydration. ...
... The contact angle of pure Fe 3 O 4 @CPAM was As can be seen from the above results, with a prolongation in irradiation time, the contact angle of Fe 3 O 4 @CPAM initially increased; this was because the hydrogen bonds of water molecules were weakened or partially destroyed by the microwave electromagnetic field, resulting in a decrease in the number of hydrogen bonds. 6 The interaction between molecules was weakened, resulting in the enhancement of the hydrophobic effect of the magnetic nanoparticles, making it easier to replace the original emulsifier molecules and adsorb onto the oil−water interface, finally promoting demulsification. However, if the microwave irradiation time was extended beyond the optimal irradiation time, the Fe 3 O 4 @CPAM contact angle decreased and its hydrophilicity was enhanced, which was harmful to the adsorption of MNPS on the surface of oil droplets, so the corresponding water separation rate also decreased. ...
In this study, cationic polyacrylamide (CPAM)-coated magnetic nanoparticles (MNPs) Fe3O4@CPAM were synthesized for treating heavy O/W emulsions. This Fe3O4@CPAM was characterized by Fourier transform infrared spectroscopy (FTIR), X-ray diffraction (XRD), thermogravimetric analysis (TGA), and vibrating sample magnetometry (VSM) techniques, and its synergistic performances with microwaves were evaluated in detail with respect to the microwave radiation power, radiation time, and magnetic nanoparticle concentration. On this basis, the distribution of oil droplets and the wettability and chargeability of magnetic nanoparticles were measured without or with microwave radiation using biomicroscopy, contact angle measurement instrument, and a ζ-potential analyzer, thus revealing the synergistic demulsification mechanism between microwave and magnetic nanoparticles. The results showed that excessively high or low microwave radiation parameters had an inhibitory effect on the magnetic nanoparticle demulsification, and microwave promoted the magnetic nanoparticle demulsification only when the radiation parameters were in the optimal range. In addition, the water separation rate showed an increasing and then decreasing trend with the increase of magnetic nanoparticles concentration, with or without microwave action. As an example, the water separation rate of the emulsion for 1 h was 21.34% when the Fe3O4 concentration was 175 mg/L without microwave action, while it increased to 55.56% with microwave action. In contrast, when the concentration of Fe3O4@CPAM was 175 mg/L, the water separation rate was 42.86% without microwave radiation, while it was further increased to 77.38% under microwave radiation. These results indicate that magnetic nanoparticles and their complexes significantly affect the water separation process under different conditions. There is a more obvious coupling synergistic effect between Fe3O4@CPAM and microwave. This was due to the lower absolute potential of Fe3O4@CPAM and its higher hydrophobicity.
... Salts have a direct impact on the emulsion IFT and stability [252]. Generally, water salinity tends to decrease surfactant hydrophilicity by reducing water and surfactant interactions in the interfacial film [253]. Binks et al. [254] studied the relationship between salt concentration, IFT, and droplet size at higher pH values. ...
Crude oil emulsions are commonly encountered in oilfield-related industries. Some of these emulsions are formed in-situ during the tertiary enhanced oil recovery process. Additionally, some recent studies reported that the formulation of emulsions ex-situ and injecting them as emulsion flooding could recover more crude oil than the traditional chemical flooding using surfactant/polymer aqueous solutions. The successful application of emulsion flooding would require the formulation of stable emulsions with specific characteristics. Thus, this article aims to review the effects of various emulsification factors (emulsification method, emulsifier type and concentration, oil type and oil/water ratio, salinity, pH, and temperature) on the key emulsion characteristics (droplet size and distribution, zeta potential, interfacial tension (IFT), flowability, and stability). Furthermore, with the growing interest in sustainability and environment protection, the replacement of chemical surfactants with biosurfactants is expected. The latter class, in addition to being environmentally-friendly and can be produced sustainably, might provide superior performance and a better tolerance to the reservoir harsh conditions relative to chemical surfactants. Thus, the available studies on the emulsion formulation using bioemulsifiers and the characteristics of the produced emulsions have also been reviewed. Moreover, some research gaps have been identified, and future research to address them has been proposed.
... However, oily wastewater often contains interfacial-active materials, resulting in the formation of highly stable oil-water emulsions, which makes treatment quite difficult. Various effective treatment techniques have been developed for oily wastewater treatment [9][10][11][12][13][14][15][16][17][18][19], such as flotation and chemical coagulation [9][10][11][12][13], advanced oxidation processes [12,14,15], demulsification [16][17][18], membrane separation [17,19,20], freeze/thaw treatment [21,22], ment techniques have been developed for oily wastewater treatment [9][10][11][12][13][14][15][16][17][18][19], such as flotation and chemical coagulation [9][10][11][12][13], advanced oxidation processes [12,14,15], demulsification [16][17][18], membrane separation [17,19,20], freeze/thaw treatment [21,22], etc. Although these technologies are quite effective, they still have some limitations. ...
... However, oily wastewater often contains interfacial-active materials, resulting in the formation of highly stable oil-water emulsions, which makes treatment quite difficult. Various effective treatment techniques have been developed for oily wastewater treatment [9][10][11][12][13][14][15][16][17][18][19], such as flotation and chemical coagulation [9][10][11][12][13], advanced oxidation processes [12,14,15], demulsification [16][17][18], membrane separation [17,19,20], freeze/thaw treatment [21,22], ment techniques have been developed for oily wastewater treatment [9][10][11][12][13][14][15][16][17][18][19], such as flotation and chemical coagulation [9][10][11][12][13], advanced oxidation processes [12,14,15], demulsification [16][17][18], membrane separation [17,19,20], freeze/thaw treatment [21,22], etc. Although these technologies are quite effective, they still have some limitations. ...
... However, oily wastewater often contains interfacial-active materials, resulting in the formation of highly stable oil-water emulsions, which makes treatment quite difficult. Various effective treatment techniques have been developed for oily wastewater treatment [9][10][11][12][13][14][15][16][17][18][19], such as flotation and chemical coagulation [9][10][11][12][13], advanced oxidation processes [12,14,15], demulsification [16][17][18], membrane separation [17,19,20], freeze/thaw treatment [21,22], ment techniques have been developed for oily wastewater treatment [9][10][11][12][13][14][15][16][17][18][19], such as flotation and chemical coagulation [9][10][11][12][13], advanced oxidation processes [12,14,15], demulsification [16][17][18], membrane separation [17,19,20], freeze/thaw treatment [21,22], etc. Although these technologies are quite effective, they still have some limitations. ...
To design more environmentally friendly, economical, and efficient demulsifiers for oily wastewater treatment, hydrophobic octadecylphosphonic acid (ODPA)-modified Fe3O4 nanoparticles (referred to as Fe3O4@ODPA) were prepared by condensation of hydroxyl groups between ODPA and Fe3O4 nanoparticles using the co-precipitation method. The prepared magnetite nanoparticles were characterized by X-ray diffraction (XRD), transmission electron microscopy (TEM), scanning electron microscope (SEM), Fourier transform infrared (FTIR) spectroscopy, and thermogravimetric/differential thermogravimetric (TG/DTG) analysis. The water contact angles (θW) of Fe3O4@ODPA nanoparticles were more than 120°, indicating hydrophobic nature, and the diameter of the obtained spherical-shaped magnetite nanoparticles was 12–15 nm. The ODPA coating amount (AO) (coating weight per gram Fe3O4) and specific surface area (SO) of Fe3O4@ODPA were 0.124–0.144 g·g−1 and 78.65–91.01 m2·g−1, respectively. To evaluate the demulsification ability, stability, and reusability, the magnetite nanoparticles were used to demulsify an n-hexane-in-water nanoemulsion. The effects of the magnetite nanoparticle dosage (CS), pH value of nanoemulsion, and NaCl or CaCl2 electrolytes on the demulsification efficiency (RO) were investigated. The RO of Fe3O4@ODPA samples was found to be higher than that of bare Fe3O4 samples (S0, ST, and SN) under all CS values. With the increase in CS, the RO of Fe3O4@ODPA samples initially increased and then approached equilibrium value at Cs = 80.0 g·L−1. A maximum RO of ~93% was achieved at CS = 100.0 g·L−1 for the Fe3O4@ODPA sample S2. The pH and two electrolytes had a minor effect on RO. The Fe3O4@ODPA nanoparticles maintained high RO even after being reused for demulsification 11 times. This indicates that the hydrophobic Fe3O4@ODPA samples can be used as an effective magnetite demulsifer for oil-in-water nanoemulsions.
... Algunos autores atribuyen la aceleración considerable de las reacciones y procesos bajo calentamiento dieléctrico por microondas al fenómeno conocido como "efecto de microondas específico", que es un efecto no térmico producido por la radiación de microondas generalmente asociado con la absorción selectiva de la energía de microondas por moléculas polares, [15][16][17] mientras que otros han tratado de demostrar que el efecto es meramente térmico, 18,19 pero aun cuando los fenómenos han sido objeto de estudio en el caso de las reacciones químicas, estos efectos no se han evaluado cuidadosamente en el proceso de desemulsificación y, hasta ahora no se ha investigado cómo acelerar el proceso de desemulsificación de emulsiones O/W, 20 es por esta razón que se ha decidido estudiar la desemulsificación de una emulsión de aceite en agua (O/W), obtenida a partir de un crudo pesado mexicano por medio del uso de microondas. ...
Información del artículo: recibido: enero 2013-aceptado: abril de 2014 Resumen Se describe una tecnología integral para el transporte de crudo pesados mediante la formación de una emulsión de aceite en agua (O/W) con el empleo de un biotensoactivo y la evaluación de las condiciones para la ruptura de la emulsión. El biotensoactivo requerido para formar la emulsión y desemulsificante empleado para romper la emulsión fueron sintetizados en los laboratorios del IMP y son biodegradables y de bajo costo. Abstract An integrated technology for the transport of heavy crude oil by means the formation of a oil-in-water emulsion(O/W) using a surfactant is described. The conditions for emulsion breaking were also evaluated. The surfactants required forming the emulsion and the demulsifiers used for breaking them were synthesized in the IMP's laboratory and are cheap and biodegradable.
... The main methods for phase separation include mechanical, electrical, thermal, and chemical processes (Issaka et al., 2015;Kocherginsky et al., 2003;Lesaint et al., 2009;Mart'ınez-Palou et al., 2013;Wu et al., 2003). Of these, thermal and chemical demulsification methods have become the popular method for treating crude oil produced as macroemulsions (Azizi & Nikazar, 2015;Peña et al., 2005). ...
Nonionic surfactants are increasingly being applied in oil recovery processes due to their stability and low adsorption onto mineral surfaces. However, these surfactants lead to the production of emulsified oil that is extremely stable and difficult to separate by conventional methods. This research characterizes the stability of crude oil mixed with a nonionic surfactant, L24–22, in a brine solution. When subjected to gravity separation, a middle oil‐rich and bottom water‐rich emulsion are generated for various water–oil ratios. Thermal treatments can effectively break oil‐rich emulsions, but the bottom water layer remains contaminated with micron‐sized crude oil droplets. A magnetic nanoparticle treatment is shown to demulsify the crude oil emulsions, dropping the total organic carbon (TOC) in the water layer from 1470 to 30 ppm.
... The results showed that the demulsification efficiency increased with decreasing pH value. Martínez-Palou et al. 3 observed that compared with the traditionally heated oil droplets, those under microwave irradiation have a larger particle size and more uneven distribution. Yang 4 studied the effects of the demulsifier concentration, microwave power, and water content of emulsions on microwave demulsification. ...
Owing to the difficulty in the demulsification of heavy oil-in-water (O/W) emulsions, the demulsification rules of magnetic nanoparticles, microwave radiation, and magnetic-nanoparticle-assisted microwaves were investigated in this study. The surface potential and droplet size of the emulsion under different demulsification conditions were investigated by using a ζ potentiometer and polarizing microscopy to reveal the mechanism of demulsification. The results showed that γ-Fe2O3 exhibited the best demulsification performance among the six magnetic nanoparticles used for demulsification. With an increase in the concentration of γ-Fe2O3, the water separation of the heavy O/W emulsion first increased and then decreased, and with a decrease in pH, the demulsification performance gradually increased. The experimental results showed that microwave demulsification had an optimal power. The demulsification efficiency was significantly improved at the synergistic action between magnetic nanoparticles and the microwave, proving that magnetic nanoparticles had a promoting effect on microwave demulsification. In addition, the recycling experiment results showed that the magnetic nanoparticles exhibited good recyclability and reusability. Finally, a temperature field model of the emulsion under the synergistic effect of microwaves and magnetic nanoparticles was established and evaluated. Both before and after the addition of the magnetic nanoparticles, the theoretical temperature of the heavy O/W emulsion was consistent with the experimental temperature at different microwave powers and radiation times.
... The former involves the use of chemical agents to destabilize the emulsified droplets, which, however, could be expensive and introduce secondary pollution for some operations [4,[9][10][11]. Physical demulsification applies external fields such as electricity, heat, ultrasound, and microwave to facilitate the coalescence and aggregation of the emulsified droplets [4,6,[12][13][14]. These techniques avoid introducing expensive chemicals and show a great potential in practical applications. ...
Hypothesis: The droplet-medium interfaces of petroleum emulsions are often stabilized by the indigenous surface-active compounds (e.g., asphaltenes), causing undesired issues. While demulsification by electric field is a promising technique, fundamental study on the droplet-medium interface influenced by electric field is limited. Molecular dynamics (MD) simulations are expected to provide microscopic insights into the nano-scaled water/oil interface.
Methods
MD simulations are conducted to study the adsorption of model asphaltene molecules (represented by N-(1-hexylheptyl)-N'-(5-carboxylicpentyl) perylene-3,4,9,10-tetracarboxylic bisimide (C5Pe)) on a water-toluene interface under various strengths of electric field. The adsorption amount and structural feature of C5Pe molecules at water-toluene interface are investigated, and the effects of electric field and salt are discussed.
Findings: C5Pe molecules tend to adsorb on the water-oil interface. As the electric field strength increases, the adsorption amount first slightly increases (or remains constant) and then decreases. The electric field disrupts the compact π-π stacking between C5Pe molecules and increases their mobility, causing a dispersed distribution of the molecules with a wide range of orientations relative to the interface. Within the studied range, the addition of salt ions appears to stabilize the interface at high electric field. These results provide useful insights into the mechanism and feasibility of demulsification under electric field.
... Consequently, different methods of dehydration of water-in-oil emulsions have been studied. These include physical [13][14][15][16], chemical [3,17] and biological [18][19][20] approaches. Physical dewatering processes like electrostatic [13], thermal [14], membranes [15] and ultrasound [16] constitute an important portfolio in the coalescence operation. ...
... These include physical [13][14][15][16], chemical [3,17] and biological [18][19][20] approaches. Physical dewatering processes like electrostatic [13], thermal [14], membranes [15] and ultrasound [16] constitute an important portfolio in the coalescence operation. This is because the physical route could overcome the challenges of extended time requirement for separation with biological methods which could hamper oil production processes. ...
In this study, a numerical assessment of the coalescence of binary water droplets in water-in-oil emulsion was conducted. The investigation addressed the effect of various parameters on the acoustic pressure and coalescence time of water droplets in oil phase. These include transducer material, initial droplet diameter (0.05-0.2 in), interfacial tension (0.012-0.082 N/m), dynamic viscosity (10.6-530 mPas), temperature (20-100 °C), US (ultra sound) frequency (26.04-43.53 kHz) and transducer power (2.5-40 W). The materials assessed are lead zirconate titanate (PZT), lithium niobate (LiNbO3), zinc oxide (ZnO), aluminum nitride (AlN), polyvinylidene fluoride (PVDF), and barium titanate (BaTiO3). The numerical simulation of the binary droplet coalescence showed good agreement with experimental data in the literature. The US implementation at a fixed frequency produced enhanced coalescence (t = 5.9-8.5 ms) as compared to gravitational settling (t = 9.8 ms). At different ultrasound (US) frequencies and transducer materials, variation in the acoustic pressure distribution was observed. Possible attenuation of the US waves, and the subsequent inhibitive coalescence effect under various US frequencies and viscosities, were discussed. Moreover, the results showed that the coalescence time reduced across the range of interfacial tensions which was considered. This reduction can be attributed to the fact that lower interfacial tension produces emulsions which are relatively more stable. Hence, at lower interface tension between the water and crude oil, there was more resistance to the coalescence of the water droplets due to their improved emulsion stability. The increment of the Weber number at higher droplet sizes leads to a delay in the recovery of the droplet to spherical forms after their starting deformation. These findings provide significant insights that could aid further developments in demulsification of crude oil emulsions under varying US and emulsion properties.
... Rheology type System of study Sztukowski et al. [184] Interface toluene\water Chang et al. [143,185] Interface toluene\decane\water Rane et al. [186] Interface Crude oil\toluene\water Oldham et al. [59] Bulk Crude oil Moncayo-Riascos et al. [103] Bulk Crude oil and p-xylene Lin et al. [154] Interface Decane\water Nguele and Okawa [104] Bulk Crude oil Moncayo-Riascos et al. [185] Bulk p-xylene and toluene Gorbacheva and Ilyin [105] Interface Ester oil\water Ariza et al. [147] Bulk Crude oil Li et al. [187] Bulk Crude oil Oliveira et al. [158] Interface Xylene\water far are the application of copolymer of ethylene oxide and propylene oxide [152,[193][194][195], conventional heating [196], microwave radiation [197][198], freeze-thaw method [199], aliphatic alcohol nonionic polyether, [200] ionic liquids polymers [201][202], nano-titania [203], and varied methods [204][205][206]. ...
Asphaltene is a component of crude oil that has been linked to serious production and transportation issues. It is a solid oil component with various shapes and molecular compositions. Deposition\aggregation\precipitation of asphaltene generates substantial flow assurance issues with considerable financial ramifications. Furthermore, emulsion formation is also found to be a serious challenge in the petroleum business. The increased viscosity of the crude oil is due to emulsified water droplets in the system. We will look at the difficulty that the petroleum sector is facing with asphaltene via a rheology lens. In this review study, we provide a brief introduction to asphaltene for the interested reader, followed by a review of the literature on asphaltene flow behavior in diverse mediums including waxy matrix, polymer matrix, oil\water emulsions, and so on. More than 150 references were used to compile this review paper including papers that explore interfacial rheology, bulk rheology, rheological modeling, and simulations.
