Ionic Liquid Surfactant Research Articles

Intensifying Stabilization and Dissolution Capacity of Polyacrylamide Emulsion Drag Reducers Using a pH-Switchable Four-Tailed Ionic Liquid Surfactant.

To balance the stability and dissolution of polyacrylamide (PAM), emulsion drag reducers dominate the successful operation of volumetric fracturing. Herein, a pH-switchable four-tailed ionic liquid surfactant (OA/Cyclen) is synthesized by oleic acid (OA) and 1,4,7,10-tetraazacyclododecane (Cyclen). The four-tailed structure of OA/Cyclen enhances the stability of the emulsion polymerization reactor and supplies enough switchable sites for triggering the intensified release of the PAM emulsion. The surface activity of OA/Cyclen varied under different pH conditions due to the interionic proton transfer between OA and Cyclen. The OA/Cyclen-stabilized monomer emulsion thus posed controllable stability. A pH-switchable PAM emulsion is produced through polymerization of this monomer emulsion, which shows a storage stability for 60 days at a pH value of 7.5. It is completely released to the aqueous solution within 20 s at a pH value of 12.03, achieving a maximum viscosity of 63 mPa·s at a polymer concentration of 0.5 wt % and a drag reduction of 61.2% at a polymer concentration of 0.05 wt %. The construction of OA/Cyclen is expected to supply an alternative for the development of drag reducer products.

Extraction of aromatic compounds by water-rich aqueous two-phase system comprising surface-active ionic liquid and cationic surfactant

Extraction of aromatic compounds by water-rich aqueous two-phase system comprising surface-active ionic liquid and cationic surfactant

The surface activity exploration of novel trisubstituted imidazolium-based ionic liquids surfactants with hexanoic acid chain

The surface activity exploration of novel trisubstituted imidazolium-based ionic liquids surfactants with hexanoic acid chain

Influence of imidazole-based ionic liquid surfactants on the wetting effect of long-flame coals

In order to study the wetting effect of C12MImBF4, C12MImBr and C12MImCl on long-flame coal, and their mechanism of action on coal-water bonding, physical experiments, molecular dynamics simulation and DFT theoretical calculation were combined in this work. It is confirmed that the imidazole ionic liquid surfactant optimizes the wetting effect by forming hydrogen bonds, reducing the surface tension of water, and increasing the number of free hydroxyl groups in coal. After the wettability test, the concentration of 4 g/L of the three ionic liquid surfactants had the best wetting effect on long-flame coal, and the contact angle at this concentration was reduced by more than 40 % compared with water within 0.2 s after dripping on the coal. Due to the difference in the anionic head group of the three surfactants, there are differences in the number and strength of hydrogen bonds formed between the three surfactants and water molecules, the results of wettability C12MImBF4 > C12MImCl > C12MImBr were presented. Combined with these characteristics of imidazole ionic liquids on long-flame coal, the reasonable application in the wet dust removal process of actual coal mine production can optimize the efficiency of droplet capture of coal particles, so as to effectively improve the dust removal capacity.

Pseudomorphic synthesis of pore size-tunable mesoporous silica spherical particles and their application for the fraction of low-molecular-weight heparin.

In this study, spherical silica with pore size varied from 30 to 200 Å was synthesized by pseudomorphic transformation at atmospheric pressure. 40-80 Å silica particles with a narrow pore distribution were obtained by using quaternary amine cationic surfactants and different kinds of swelling agents, including polypropylene glycol, 1,3,5-trimethylbenzene, alkanes, and alkanols. Alkyl imidazolium ionic liquid surfactants were used to synthesize large pore size distribution silica spheres with pore sizes in the range of 110-200 Å. All these silica particles can be synthesized under mild conditions within 12h, which provides a facile synthesis method for the preparation of a chromatographic matrix with tunable pore size. The method is reproducible and the relative standard deviation of silica sphere pore structure parameters in scaled-up preparations is less than 6%. The pore size on the fraction of low-molecular-weight heparin (LMWH) was investigated in size exclusion chromatography. Matrixes with different pore size distributions have various size exclusion regions. By using UPS-60-Diol columns in a twin-column recirculation separation process, LMWH with>85% heparin with molecular weight within the range of 3000-8000Da were separated in five-column volumes.

Qualifying interfacial properties of crude oil−water system with the synergistic action of a nano Gemini ionic liquid and conventional surfactants

Surface-active ionic liquids (SAILs) have gained much attention due to their green, stable, and efficient properties. The high costs associated with SAILs have raised concerns in their applications; however, blending with conventional surfactants like sodium dodecyl benzene sulfonate (SDBS) can bring about desired outcomes. Gemini surface-active ionic liquids (GSAILs) have been recognized as more efficient surfactants. Accordingly, this study investigates the influence of a mixture of an imidazolium-based GSAIL, [C4im-C6-imC4][Br2], and SDBS on different aspects of crude oil−water interfacial properties. The findings show remarkable synergy in interfacial tension (IFT) reduction up to 98.8% together with incredibly low IFT value of 0.05 mN m−1. This was with an optimal GSAIL mole fraction of 0.2 in the mixture. Further, the surfactant mixture gives synergies of 52.6% in emulsification and 51.8% in wettability of a quartz surface. These amazing results can be explained by the dominant interactions between the oppositely charged components. In theoretical study, the adsorption of individual surfactants and their mixtures was analyzed based on the Frumkin isotherm and the Rosen model, respectively, further supporting the findings.

Utilizing Deep Eutectic Solvent in Microemulsion for Eco‐Friendly Synthesis of Fluorescent Carbon Nanoparticles and their Highly Sensitive Sensing of Antibiotics and Nitroaromatic Compounds

AbstractMicroemulsions (MEs) comprising of cholinium dodecylbenzene sulphonate Cho[DBS], a bio‐based ionic liquid surfactant as an emulsifier, hydrophobic deep eutectic solvent (HDES) as nonpolar phase, and water as a polar component are constructed. Negative value of ∆G estimated from isothermal titration calorimetry (ITC) plots indicate spontaneous aggregation of Cho[DBS] both in water and HDES. The aggregates of Cho[DBS] in HDES and water show the critical micellar concentration (cmc) of ≈4.26 and ≈2.4 mMm, respectively. Cho[DBS] shows a better emulsifying capacity with a high monophasic region in the ternary phase diagram. MEs are utilized as nanoreactors for the sustainable synthesis of nano‐sized fluorescent carbon nanoparticles (FCNPs) with precise control over size and morphology. FCNPs are characterized using PXRD, Raman, XPS, HR‐TEM, UV–vis, and Fluorescence spectroscopic techniques. FCNPs exhibited remarkable properties viz. adjustable luminescence, good solubility, and biocompatibility. FCNPs are applied for fluorometric sensing of nitroaromatic compounds (NACs) and antibiotics through a quenching response originating from the inner filter effect, with a fast response nanomolar detection, and are found highly selective toward TNP (NAC), NFT, and NZF (antibiotics).

Impact of surface-active ionic solutions on the structure and function of laccase from trametes versicolor: Insights from molecular dynamics simulations

Many protein-ionic liquid investigations have examined laccase interactions. Laccases are a class of poly-copper oxidoreductases that retain significant biotechnological relevance owing to their notable oxidative capabilities and their application in the elimination of synthetic dyes, phenolic compounds, insecticides, and various other substances. This study investigates the impact of surface active ionic liquids (SAILs), namely, decyltrimethylammonium bromide [N10111][Br] and 1-decyl-3-methylimidazolium chloride [C10mim][Cl] as cationic surfactant ionic liquids and cholinium decanoate [Chl][Dec], an anionic surfactant ionic liquid, on the structure and function of laccase from the fungus Trametes versicolor (TvL) by the molecular dynamics (MD) simulation method. In summary, this study showed that laccase solvent-accessible surface area increased in the ionic liquid [Chl][Dec] while it decreased in the other two ionic liquids. Interestingly, [Chl][Dec] ionic liquid components formed hydrogen bonds with laccase, while [N10111][Br] and [C10mim][Cl] components were unable to form hydrogen bonds with laccase. The quantity of hydrogen bonds formed between water molecules and the enzyme was also diminished in the presence of [Chl][Dec] in comparison to the other two ionic liquids. especially at a concentration of 250 mM. In 250 mM concentrations of [N10111][Br] and [C10mim][Cl], clusters of long-chain cations are likely to form near the copper T1 site. However, even at low [Chl][Dec] concentrations, long [Dec]- chains were observed to penetrate the enzyme near the copper T1 site, and at 250 mM [Chl][Dec], a large cluster of anions occupied the opening of the active site. The results of the analysis also show that the interaction between the [Dec]- anion and the enzyme is stronger than the interaction between [N10111]+ and [C10mim]+ with laccase; in addition, the [Dec]- anion, compared to [Br]- and [Cl]- has a much greater tendency to bind with the enzyme residues.

An inclusive comparison regarding aggregation of surface active ionic liquid and conventional surfactant with a cationic dye Acridine Red exposed in view of spectroscopic and theoretical study

The investigation was conducted on the interaction of acridine red (AR) with sodium dodecyl sulfate (SDS) and 1-butyl-3-methyl imidazolium octyl sulfate (BMImOS) in both premicellar and post micellar concentrations. The interaction between AR and room temperature ionic liquid (RTIL) 1-butyl-3-methyl imidazolium bromide (BMImBr) was studied to understand the effect of imidazolium cation on micellization. Spectroscopic experiments, such as UV–visible absorption spectroscopy, steady-state fluorescence spectroscopy, time-resolved fluorescence spectroscopy, and dynamic light scattering, have been introduced. Various important parameters like spectral shifts, anisotropy, and aggregation number have been determined spectroscopically. However, a fresh insight into density functional theory calculations has also been provided. The observed results have been explained in terms of the aggregation behavior of the amphiphiles. A prominent redshift accompanied by a change in intensity is observed in the presence of surfactant and SAIL. However, in the case of BMImBr, no such spectral shift has been observed; only a decrease in spectral intensity highlights the quenching ability of the imidazolium cation. Average lifetime also provides some additional information regarding the difference in the formation of aggregates by SDS and BMImOS, which is further established from particle size density obtained from DLS. The salt like role of 1-butyl-3-methyl imidazolium cation also has been logically explained by anisotropy measurement and the determination of aggregation number. Using Gauss View 5.0 and Gaussian 09 package, the energy of optimization of each set of amphiphiles along with dye has been determined to follow the interaction at the molecular level. TDDFT calculations have also been performed to determine the structure of HOMO and LUMO.

Effect of protic surfactant ionic liquids based on ethanolamines on solubility of acetaminophen at several temperatures: measurement and thermodynamic correlation

Absolute qualifications with the application of protic ionic liquids (PILs) and a recognition of the numerous thermophysical features of these materials are required in various processes. Due to the wonderful applications of these compounds and their high potential in the chemical and pharmaceutical industries, there is a particular eagerness to utilize these PILs in drug solubility and delivery area. The aim of this investigation was to explore the solubility of the acetaminophen (ACP) in three PILs base on ethanolamine laurate [(2-hydroxyethylammonium laurate [MEA]La), (bis(2-hydroxyethyl)ammonium laurate [DEA]La), and ( tris(2-hydroxyethyl)ammonium laurate [TEA]La)]. The shake flask method has been employed in this study, and the conditions were set at T = (298.15–313.15) K and atmospheric pressure. Moreover, the experimental solubility data was correlated using a variety of empirical and thermodynamic models, encompassing e-NRTL and Wilson activity coefficient models and the empirical models such as Van’t Hoff-Jouyban-Acree and Modified Apelblat-Jouyban-Acree. Their performance for the system containing [MEA]La follow the trend for activity coefficient models and empirical respectively: the Wilson > e-NRTL and Modified Apelblat–Jouyban–Acree > Van’t Hoff–Jouyban–Acree. On the other hand, [DEA]La and [TEA]La PILs followed slightly different trend for activity coefficient models and empirical respectively: the Wilson > e-NRTL and Van’t Hoff–uyban–Acree > Modified Apelblat–Jouyban–Acree. The Van’t Hoff and Gibbs equations were used to determine the thermodynamic properties of dissolution in the studied systems.

Exploring the Properties of Unilamellar Vesicle Bilayers Formed by Ionic Liquid Surfactants for Future Applications in Nanomedicine.

Two ionic liquids (ILs) with amphiphilic properties composed of 1-butyl-3-methylimidazolium dioctylsulfosuccinate (bmim-AOT) and 1-hexyl-3-methylimidazolium dioctylsulfosuccinate (hmim-AOT) form unilamellar vesicles spontaneously simply by dissolving the IL-like surfactant in water. These novel vesicles were characterized using two different and highly sensitive fluorescent probes: 6-propionyl-2-(dimethylaminonaphthalene) (PRODAN) and trans-4-[4-(dimethylamino)-styryl]-1-methylpyridinium iodide (HC). These fluorescent probes provide information about the physicochemical properties of the bilayer, such as micropolarity, microviscosity, and electron-donor capacity. In addition, the biocompatibility of these vesicles with the blood medium was evaluated, and their toxicity was determined using Dictyostelium discoideum amoebas. First, using PRODAN and HC, it was found that the bilayer composition and the chemical structure of the ions at the interface produced differences between both amphiphiles, making the vesicles different. Thus, the bilayer of hmim-AOT vesicles is less polar, more rigid, and has a lower electron-donor capacity than those made by bmim-AOT. Finally, the results obtained from the hemolysis studies and the growth behavior of unicellular amoebas, particularly utilizing the D. discoideum assay, showed that both vesicular systems do not produce toxic effects up to a concentration of 0.02 mg/mL. This elegant assay, devoid of animal usage, highlights the potential of these newly organized systems for the delivery of drugs and bioactive molecules of different polarities.

Effective Synergistic Action of Benzimidazolium Nano Gemini Ionic Liquid and Conventional Surfactant for Chemical Enhanced Oil Recovery.

Blends of newly developed Gemini surface-active ionic liquids (GSAILs) and conventional surfactants offer significant enhancements to the interfacial properties between crude oil and water, providing economic benefits in chemically enhanced oil recovery. In this study, the mixtures of a benzimidazolium cationic GSAIL, [C4benzim-C6-benzimC4][Br2], and sodium dodecyl benzenesulfonate (SDBS) were successfully utilized for improving crude oil-water interfacial properties. The research revealed synergistic effects of up to 99.6% in reducing interfacial tension (IFT), achieving a low IFT value of 0.04 mN m-1 corresponding to an optimal GSAIL mole fraction of 0.2 for the mixture of surfactants. Additionally, significant synergies of 53.4 and 74% were observed in oil-water emulsification and in surface wettability when using a GSAIL mole fraction of 0.2. These results showcase the importance of the dominant interaction between the opposite-charged surfactants. The Frumkin isotherm and the Rosen model were employed for the theoretical study of adsorption behavior of individual surfactants and their mixture at the interface, demonstrating reasonable parameter variations. The overall findings emphasize the potential of utilizing these unique blends to enhance oil recovery processes through tailored interfacial properties.

One-Pot synthesis and interfacial activity of imidazolium ionic liquid surfactants with double-chain hydrophobic

Three double-chain imidazolium ionic liquid surfactants (ILS) with varying alkyl lengths, namely [C10mimC10][OAc], [C12mimC12][OAc], and [C14mimC14][OAc], were synthesized via the one-step Debus-Radziszewskireaction. The chemical structures of these three ILS were confirmed through FT-IR, 1H NMR and ESI-MS analyses. Their surface/interface activity, wetting ability, thermal stability, and aggregation properties were investigated. The results indicated that the presence of double-chain hydrophobic groups in ILS exerted a significant influence on their surface/interface activity. Surface activity and micellization properties were assessed using surface tension measurements, revealing that the micellization process of double-chain ILS was more favorable compared to single-chain ILS. Among the three ILS examined, [C14mimC14][OAc] exhibited the lowest surface tension and critical micelle concentration (CMC) values, measuring 29.07 mN/m and 1.64 × 10-2 mmol/L, respectively. Solutions containing approximately 50 ppm of these ILS could reduce interfacial tension to below 1 mN/m. Additionally, the contact angle decreased to less than 90° within 90 s. The formation of aggregates in aqueous solutions was found to be influenced by the number of CH2 units present in the different ILS molecules.

Insights into the Efficient Release of the Polyacrylamide Drag Reducer via a pH-Responsive Inverse Polymer Emulsion.

The enormous demand for petroleum consumption has resulted in the shortage of fossil resources, prompting the need to explore unconventional reservoirs. Polyacrylamide emulsion drag reducers are capable of inhibiting the turbulence of fracturing fluids for enhancing the reservoir stimulation results, but the poor dissolution efficiency of polyacrylamide emulsion drag reducers is the primary limitation to their large-scale application. Here, a pH-responsive ionic liquid surfactant, oleic acid/cyclohexanediamine (HOA/HMDA), is synthesized by using oleic acid (HOA) and cyclohexanediamine (HMDA). HOA/HMDA shows a remarkable pH-responsive behavior due to the pH-induced deconstruction of the HOA/HMDA structure. Interestingly, the HOA/HMDA-stabilized monomer emulsion exhibits an obvious pH-induced emulsion structure transformation behavior. In addition, the HOA/HMDA-stabilized monomer emulsion possesses excellent dynamic and storage stability, supporting the inverse emulsion polymerization of the polymer P(AM/AMPS/AA). The obtained P(AM/AMPS/AA) polymer inverse emulsions maintained stability for 30 days. Our finding proposes that the structure of the P(AM/AMPS/AA) polymer inverse emulsions changes with pH stimulation, which is capable of facilitating the release of polymers. P(AM/AMPS/AA) is released from the P(AM/AMPS/AA) polymer inverse emulsions within 30 s at a pH value of 12.06, along with a drag reduction rate of 62.54%. Obviously, the HOA/HMDA-stabilized P(AM/AMPS/AA) polymer inverse emulsions eliminate the contradiction between the stability and release of polyacrylamide emulsion drag reducers, which is promising for meeting the demands of reservoir stimulation.

Surfactant ionic liquids alter the stabilities of G-quadruplex DNA and RNA structures

Surfactant ionic liquids alter the stabilities of G-quadruplex DNA and RNA structures

Density and Speed of Sound for Dilute Binary and Ternary Mixtures of Gabapentin with Surfactant Ionic Liquids Based on Ethanolamine Laurate in Aqueous Solutions at Different Temperatures

Density and Speed of Sound for Dilute Binary and Ternary Mixtures of Gabapentin with Surfactant Ionic Liquids Based on Ethanolamine Laurate in Aqueous Solutions at Different Temperatures

A green alternative to replace anionic viscoelastic surfactant based fracturing fluid with enhanced properties

Ionic liquid surfactant (ILS) presents a promising alternative for balancing the conflicting relationship of hydrophobicity and water solubility in anionic surfactants. Despite this potential, the utilization of ultra-long chain anionic ILS in viscoelastic surfactant (VES) fracturing fluids has been infrequently reported. In our previous research, we successfully prepared a viscoelastic wormlike micelles (WLMs) by employing an ultra-long chain ILS known as Adamantyl trimethyl ammonium erucate (AdEr) with potassium chloride (KCl). This novel system opens up promising avenues for its application in fracturing fluids. This study aims to comprehensively investigate the impact of temperature on the behavior of AdEr/KCl wormlike micelles, thereby evaluating the fracturing fluid performance. In rheological experiments, we observed that the zero-shear viscosity (η0) of AdEr/KCl WLMs remains at ∼103mPa·s at 90 °C, demonstrating excellent thermal resistance. Molecular dynamic (MD) simulations demonstrated that, as the temperature increased, it initially resulted in the disintegration of the aggregate structure, followed by a remarkable reformation of the same structure. This observed behavior can be attributed to the gradual decrease in polarity of the adamantyl groups as the temperature increases. Finally, the AdEr/KCl-based fracturing fluids, AE-1 and AE-2, not only exhibit outstanding temperature resistance (90 °C and 130 °C, respectively) but also demonstrate exceptional proppant-carrying and oil-induced gel-breaking capabilities. This study promotes the utilization of anionic ILSs in the formulation of environmentally-friendly fracturing fluids, emphasizing the crucial role of understanding temperature-induced changes through MD simulations.

Experimental investigation of combined carbon nanoparticles (CNPs), ionic liquid (I.L), and low salinity water to enhance oil recovery (EOR) at Iraq's southern oil fields

By 2030, global energy demand is expected to increase by 50% with respect to 2020. However, supplies of natural gas and oil are steadily depleting. Therefore, implementing innovative enhanced oil recovery (EOR) technology in producing reservoirs is essential to meeting the growing energy demand.EOR is a technique that has currently been in use to increase the rate of oil production. This research demonstrates the novel opportunities of combining carbon nanoparticles, ionic liquid surfactant (dodecyl pyridinium chloride), and low-salinity water to improve oil recovery from carbonate reservoirs. A series of experimental works, comprising sedimentation technique, zeta potential analysis, contact angle measurements, and surface tension tests, were conducted to study the stability and choose the optimal nanofluid for application in EOR.It was discovered that by adding various concentrations of an ionic liquid to a 50 ppm nanocarbon solution, the density of the nanofluid formulations could be slightly reduced, the surface tension could be changed, and the wettability of carbonate rocks could be altered from an oil-wet to a water-wet system. Core-flooding tests were carried out for optimum nanofluid formulation (50 ppm of nanocarbon with 250 ppm of ionic liquid) at different flow rates. Additional oil recoveries of 8.46 % and 20.5 % of the original oil in place were achieved at flow rates of 0.667 cm3/min and 0.334 cm3/min, respectively. This study is one of the first to be conducted in Iraq's oil fields to investigate the potential for EOR using carbon nanoparticles, ionic liquid, and low-salinity water. The results of this research highlight the potential of hybrid nanofluids as a new type of injection fluid for EOR.

Synergism in mixtures of nano benzimidazolium Gemini ionic liquid and sodium dodecyl sulfate surfactants in tuning interfacial properties of crude oil−water system

The high price of newly explored surfactants is a concern in applications, but their mixture with conventional surfactants can bring about desired outcomes. Gemini surface active ionic liquids (GSAILs) have emerged as unique materials in tuning interface properties. Surfactants like sodium dodecyl sulfate (SDS), on the other hand, are known effective and commercially available. This study investigates the simultaneous effects of a benzimidazolium cationic GSAIL, [C4benzim-C6-benzimC4][Br2], and SDS surfactants on the interfacial tension (IFT), emulsification, and wettability alteration of the crude oil−water system. The results demonstrate amazing synergies up to 97.6 % in the IFT reduction. An ultra-low IFT of 0.16 mN·m−1 was achieved with an optimum GSAIL mole fraction of 0.4, attributed to the attractive interaction between the cationic GSAIL and the anionic SDS. Mixtures also give 54.3 and 72.8 % synergies in emulsification and wettability alteration, respectively. The adsorption of individual and mixture of surfactants were theoretically analyzed using the Frumkin adsorption isotherm and the non-ideal interactions of the binary mixtures (NIBM) theory. The corresponding determined parameters were consistent. To have a more comprehensive analysis, the results were compared with those obtained with an analogous structure imidazolium GSAIL.

Pore-scale investigation on the flow behavior and oil displacement of ultralow IFT surfactant flooding based on CFD simulation

In order to investigate the flow behavior and oil displacement of ultralow interfacial tension (IFT) surfactant flooding, the experimentally validated computational fluid dynamics simulation model is constructed by coupling the Navier-Stokes equations and the Cahn-Hilliard equation. The mixed surfactant solution is prepared using the ionic liquid surfactant and the nonionic surfactant, and the fluid parameters are measured experimentally. Due to the reduced oil-water IFT, the low pressure drop in porous medium and the decreased oil viscosity, ultralow IFT surfactant contributes to increasing the mobility ability of the fluid front in pores, and its optimal injection velocity is 0.01 m/s. In addition, the sweep area of surfactant flooding in oil-wet porous medium is significantly larger than that of brine flooding because of wettability alteration. Finally, for different porosity models, the residual oil content and the pressure drop of surfactant flooding show a 66.7% and 71.4% decrease than those of brine flooding, respectively, proving its better displacement performance.