Imidazolium-based Ionic Liquids Research Articles

Spatial organization of the ions at the free surface of imidazolium-based ionic liquids

HypothesisExperimental information on the molecular scale structure of ionic liquid interfaces is controversial, giving rise to two competing scenarios, namely the double layer-like and “chessboard”-like structures. This issue can be resolved by computer simulation methods, at least for the underlying molecular model. Systematically changing the anion type can elucidate the relative roles of electrostatic interactions, hydrophobic (or, strictly speaking, apolar) effects and steric restrictions on the interfacial properties. SimulationsMolecular dynamics simulation is combined with intrinsic analysis methods both at the molecular and atomic levels, supplemented by Voronoi analysis of self-association. FindingsWe see no evidence for the existence of a double-layer-type arrangement of the ions, or for their self-association at the surface of the liquid. Instead, our results show that cation chains associate into apolar domains that protrude into the vapour phase, while charged groups form domains that are embedded in this apolar environment at the surface. However, the apolar chains largely obscure the cation groups, to which they are bound, while the smaller and more mobile anions can more easily access the free surface, leading to a somewhat counterintuitive net excess of negative charge at the interface. Importantly, this excess charge could only be identified by applying intrinsic analysis.

A comparative study on the solubility of CH3SH and H2S in imidazolium-based ionic liquids: A connectionist approach between free volume and thermodynamics

Sulfur contaminants in industrial gas streams, such as hydrogen sulfide and mercaptans, must be eliminated due to safety and environmental considerations. Ionic liquids, as a new class of chemical compounds, are an alternative to conventional aqueous alkanolamine solutions currently used in absorption gas treatment processes. In this work, the solubilities of methyl mercaptan (CH3SH) and hydrogen sulfide gases in 1-butyl-3-methylimidazolium-based ionic liquids with tetrafluoroborate ([C4mim][BF4]), hexafluorophosphate ([C4mim][PF6]), trifluoromethanesulfonate ([C4mim][OTf]), and bis(trifluoromethylsulfonyl)imide ([C4mim][Tf2N]) anions have been studied using molecular dynamics (MD) simulation and a recently developed OPLS all-atom (OPLS-AA-0.8) force field. A new concept, the induced free volume, has been introduced in this work, which provides a realistic and precise connection between the thermodynamic entropic contributions to the dissolution process of CH3SH and H2S in the ionic liquids, on one hand, and the microscopic free/void volume induced as a result of the entrance of a gas solute molecule into the liquid structure, on the other hand. The thermodynamic energetic contributions were correlated to the CH3SH/H2S interaction with the ionic species of the ionic liquids. Quantum chemical energy decomposition analysis (EDA) was employed to calculate and analyze the binding interaction and nature of CH3SH/H2S interactions with the ionic species of ionic liquids. It was found that the van der Waals contributions to the interaction of CH3SH with ionic liquids are more significant compared to that of H2S, while the opposite conclusion could be deduced for the corresponding electrostatic contributions. Both CH3SH and H2S established equivalent hydrogen bonding interactions with the ionic liquids studied in this work. The diffusion coefficients of the ionic species, as well as the excess chemical potentials and Henry’s constants for the dissolution of CH3SH and H2S in the ionic liquids, were calculated by free energy perturbation technique (FEP) and compared with the MD simulated and experimental data, reported in the literature. It was concluded that the OPLS-AA-0.8 force field yields Henry’s constants and diffusivities that are in better agreement with the reliable experimental data corresponding to other OPLS versions reported to date.

Enhanced corrosion resistance performance of the novel tripodal imidazolium-based ionic liquid: Experimental and theoretical investigations

The imidazolium-based ionic liquids (ILs) were widely recognized as the eco-friendly corrosion inhibitors. Many literatures focused on enhancing the corrosion inhibition efficacy via the modification of various functional groups to ILs. The present study investigated the corrosion resistance performance of the novel synthesized tripodal IL ([(C4im)3TA][Cl3]) with a triazine spacer and three imidazolium cations for mild steel (MS) in 1 M HCl solution. The inhibition efficiencies of [(C4im)3TA][Cl3] at the concentrations of 0.1 mM (55.7 ppm, 80 %) and 0.5 mM (278.5 ppm, 86 %) were found to be comparable to, and higher than that of conventional imidazolium-based ILs 1‑butyl‑3-methylimidazolium chloride (C4mimCl) at 10 mM (1747 ppm, 81 %), respectively. The adsorption behavior of [(C4im)3TA][Cl3] at the metal surface was reflected through X-ray photoelectron spectroscopy, and the adsorption mechanism was further investigated using quantum chemical calculations and molecular dynamics simulations. The results indicated the greater ability of [(C4im)3TA][Cl3] to form chemical bonds with Fe atoms, which induced the generation of the more stable hydrophobic protection film at the surface. This study presented the novel concept for the structural design of high-efficiency corrosion inhibitors based on imidazolium ILs.

Imidazolium-Based Polymeric Ionic Liquids with Short Alkyl Chains as Green Corrosion Inhibitors for Mild Steel in 1 M HCl: Experimental and Theoretical Investigations.

A novel polymeric ionic liquid (PDBA-IL-NH2) using imidazolium ionic liquids with short alkyl chains as monomers and two control ionic liquids (PDBA-IL-OH and PIL-NH2) were synthesized. Their inhibition properties and mechanisms were explored via surface analysis, weight loss tests, electrochemical studies, and adsorption isotherm analysis. The corrosion inhibition efficiency (CIE) of PDBA-IL-NH2 gradually increased with increasing concentration, and the largest efficiency was 94.67% at 100 ppm. At the same concentration (50 ppm), the corrosion inhibition abilities of inhibitors were in the order of PDBA-IL-NH2 > PDBA-IL-OH > PIL-NH2 > IL-NH2. Based on the experimental investigation, the synergistic effect of electrostatic interaction, protonation, and electron donor-acceptor interaction facilitated the intensive entanglement and coverage of PDBA-IL-NH2 with the reticulated form on the metal, and the generated densest films protected the metal from the corrosive media. Ultimately, the theoretical results of molecular dynamics simulations and quantum chemical study were in high agreement with the experimental data, which confirmed the proposed inhibition mechanisms on the microscopic scale. This study contributed valuable perspectives to the design of efficient and ecofriendly corrosion inhibitors.

Enhancing the Cycle Life of Zinc–Iodine Batteries in Ionic Liquid‐Based Electrolytes

AbstractAqueous zinc–iodine (Zn−I2) batteries are gaining significant attention due to their low‐cost, high safety and high theoretical capacity. Nevertheless, their long cycle and durability have been hampered due to the use of aqueous media that, over time, lead to Zn dendrite formation, hydrogen evolution reaction, and polyiodide dissolution. Xiao et al. recently reported the addition of an imidazolium‐based ionic liquid (IL) to an aqueous electrolyte and found that the IL plays a key role in modifying the solvation of Zn2+ ions in the bulk electrolyte and the inner Helmholtz plane, repelling H2O molecules away from the Zn anode surface. UV/Vis and NMR spectroscopy also indicates a strong interaction between imidazolium cation [EMIM]+ and I3−, thereby reducing polyiodide shuttling and enhancing the cycle life of the battery. Overall, a capacity decay rate of only 0.01 % per cycle after over 18,000 cycles at 4 A g−1, is observed, making the use of IL additives in aqueous electrolytes highly promising candidates for Zn−I2 batteries.

Enhancing the Cycle Life of Zinc-Iodine Batteries in Ionic Liquid-Based Electrolytes.

Aqueous zinc-iodine (Zn-I2) batteries are gaining significant attention due to their low-cost, high safety and high theoretical capacity. Nevertheless, their long cycle and durability have been hampered due to the use of aqueous media that, over time, lead to Zn dendrite formation, hydrogen evolution reaction, and polyiodide dissolution. Xiao et al. recently reported the addition of an imidazolium-based ionic liquid (IL) to an aqueous electrolyte and found that the IL plays a key role in modifying the solvation of Zn2+ ions in the bulk electrolyte and the inner Helmholtz plane,repelling H2O molecules away from the Zn anode surface. UV/Vis and NMR spectroscopy also indicates a strong interaction between imidazolium cation [EMIM]+ and I3 -, thereby reducing polyiodide shuttling and enhancing the cycle life of the battery. Overall, a capacity decay rate of only 0.01 % per cycle after over 18,000 cycles at 4 A g-1, is observed, making the use of IL additives in aqueous electrolytes highly promising candidates for Zn-I2 batteries.

Polymerization-induced self-assembly amino acid ionic liquid/poly(ethylene oxide) thin-film composite membranes for CO2 separation

It is well known that crosslinking poly(ethylene oxide) (PEO) membranes exhibit high CO2/N2 solubility selectivity, and are suitable for separating CO2 from flue gas. However, the high CO2/N2 selectivity is temperature sensitive and decreases rapidly with increasing temperature. To overcome this deficiency, imidazolium-based amino acid ionic liquids (AAILs) are introduced into the PEO membranes. A series of (AAILs-PEO)/PAN thin-film composite (TFC) membranes were prepared by a polymerization-induced self-assembly process. Due to the hydrogen and Coulomb interactions between the imidazolium ring of AAILs and the ether groups of PEO monomers, the morphology of the selective layer changed from micellar to granular upon the introduction of the AAILs into the PEO membranes, while the chain-segment flexibility and interspacing of the PEO are also changed. Compared with the original PEO/PAN TFC membrane, the (AAILs-PEO)/PAN TFC membranes show much higher CO2/N2 selectivity, which increases from ∼41 to ∼ 74. In addition, the AAILs show strong hydrophilicity, which leads to a significant increase in CO2/N2 selectivity under the wet-gas feed, reaching ∼105. Compared with the original PEO/PAN TFC membranes with CO2/N2 selectivity of ∼10 at 70 °C, the (AAILs-PEO)/PAN TFC membranes show the selectivity of ∼30, coupled with CO2 permeance of ∼1300 GPU at 70 °C. Under the 40: 60 mixtures of CO2: N2, which is a common lime kiln exhaust gas, by using the (AAILs-PEO)/PAN TFC membrane, the CO2 concentration on the downstream side can reach over 90 % at 20 °C and over 70 % at 70 °C, respectively, under a pressure ratio of 5.

Erratum for Gomes et al., "Boosting Cosmeceutical Peptides: Coupling Imidazolium-Based Ionic Liquids to Pentapeptide-4 Originates New Leads with Antimicrobial and Collagenesis-Inducing Activities".

Erratum for Gomes et al., "Boosting Cosmeceutical Peptides: Coupling Imidazolium-Based Ionic Liquids to Pentapeptide-4 Originates New Leads with Antimicrobial and Collagenesis-Inducing Activities".

Imidazole-Based Ionic Liquid Engineering for Perovskite Solar Cells with High Efficiency and Excellent Stability.

Despite the remarkable progress of perovskite solar cells (PSCs), the substantial inherent defects within perovskites restrict the achievement of higher efficiency and better long-term stability. Herein, we introduced a novel multifunctional imidazole analogue, namely, 1-benzyl-3-methylimidazolium bromide (BzMIMBr), into perovskite precursors to reduce bulk defects and inhibit ion migration in inverted PSCs. The electron-rich environment of -N- in the BzMIMBr structure, which is attributed to the electron-rich adjacent benzene ring-conjugated structure, effectively passivates the uncoordinated Pb2+ cations. Moreover, the interaction between the BzMIMBr additive and perovskite can effectively hinder the deprotonation of formamidinium iodide/methylammonium iodide (FAI/MAI), extending the crystallization time and improving the quality of the perovskite precursors and films. This interaction also effectively inhibits ion migration to subsequent deposited films, leading to a noteworthy decrease in trap states. Various characterization studies show that the BzMIMBr-doped films exhibit superior film morphology and surface uniformity and reduced nonradiative carrier recombination, consequently enhancing crystallinity by reducing bulk/surface defects. The PSCs fabricated on the BzMIMBr-doped perovskite thin film exhibit a power conversion efficiency of 23.37%, surpassing that of the pristine perovskite device (20.71%). Additionally, the added BzMIMBr substantially increased the hydrophobicity of perovskite, as unencapsulated devices still retained 93% of the initial efficiency after 1800 h of exposure to air (45% relative humidity).

Technoeconomic and environmental impact assessment of industrial scale biodiesel production process from algal oil using a reusable basic ionic liquid magnetic nanocatalyst

A unique magnetically reusable basic ionic liquid nanocatalyst was designed to convert algal oil into biodiesel. The imidazolium-based basic ionic liquid (BIL) was immobilized onto the magnetic nanocomposite (Fe3O4-SiO2), resulting in Fe3O4-SiO2-BIL nanocatalyst with notable properties of large surface area (21.963 m2/g), high saturation magnetization (28.78 emu/g) and high thermal stability. The nanocatalyst effectively facilitated algal oil transesterification with 96.94 % biodiesel yield under methanol: oil ratio of 8.58:1 and a catalyst dosage of 4.59 % at 60.60 °C for 87.42 min. The transesterification reaction proceeded with pseudo-first-order kinetics, featuring a relatively low activation energy. The nanocatalyst showed excellent reusability for eight recycles. A techno-economic analysis demonstrated that industrial-scale biodiesel production from algal feedstock was economically viable with a minimum payback of 2.25 years. The environmental analysis revealed a low carbon footprint with the emission of 0.074 kg CO2 per kg of biodiesel produced. This research presents a sustainable approach for biodiesel production from algal feedstock facilitated by Fe3O4–SiO2–BIL nanocatalyst, offering both environmental and economic benefits.

Mo-MOF-based ionanofluids for highly efficient extraction coupled catalytic oxidative desulfurization

Ionanofluids as newly introduced types of nanofluids with promising potential for diverse applications are created through dispersing nanoparticles into ionic liquids. Ionanofluids capitalize on both the catalytic ability of nanoparticles and the rapid mass transfer along with the extraction performance of ionic liquids. Herein, a novel kind of ionanofluids (denoted Mo-INFs) was constructed by employing a Mo-MOF as the nanoparticle and an imidazole-based ionic liquid ([BDIM][NTF2]) as the base fluid. As the efficiency of Mo-INFs (97.9 %) surpassed the summarized efficiency of Mo-MOF and [BDIM][NTF2], a synergistic effect between the Mo-MOF moiety and the [BDIM][NTF2] moiety in Mo-INFs did exist. Under optimum reaction conditions, the Mo-INFs exhibited remarkable selectivity and recyclability in desulfurization. A possible desulfurization mechanism was proposed that aromatic sulfur compounds in the model oil phase were initially extracted into ionanofluids phase via C-H···π and π···π interactions and subsequently oxidized by peroxo species that formed in the presence of H2O2 and Mo-MOF.

Insight into the Inflection Point of Surface Tension in Aqueous Solution of Imidazolium-Based Ionic Liquids

Insight into the Inflection Point of Surface Tension in Aqueous Solution of Imidazolium-Based Ionic Liquids

Computational study of Capturing CO2 and SO2 gases using imidazolium-based ionic liquids

Computational study of Capturing CO2 and SO2 gases using imidazolium-based ionic liquids

Evaluation of chemical reactivity and polarity of imidazolium-based ionic liquids using quantum chemical calculations.

By using the DFT theory, the orbital energies of twenty-five ionic liquids were estimated. To comprehend their molecular stability and chemical reactivity, the orbital energy values, orbital energy gap (HOMO-LUMO energy gap), chemical hardness (η), chemical softness (S), electronegativity (χ), and electrophilicity index (ω) were computed. The interaction energies between all of the cations and anions under study were then computed and examined. Finally, using quantum chemical calculations, the molecular polarity of all 25 ionic liquids was examined using the sigma profile and sigma potential. Using the lowest orbital energy of the molecules, HF/6-31G* level of theory quantum chemical calculation were carried out using the MOLDEN and GAUSSIAN03 software. The B3LYP DFT approach produced a COSMO file that contained the species optimal SCD.

Extraction of Dibenzyl Disulfide from Transformer Oils by Acidic Ionic Liquid.

In recent years, dibenzyl disulfide (DBDS) in transformer oils has caused many transformer failures around the world, and its removal has attracted more attention. In this work, nine imidazolium-based ionic liquids (ILs) were applied as effective, green desulfurization extractants for DBDS-containing transformer oil for the first time. The results show that the desulfurization ability of the ILs for DBDS followed the order of [BMIM]FeCl4 > [BMIM]N(CN)2 > [BMIM]SCN > [BMIM](C4H9O)2PO2 > [BMIM]MeSO4 > [BMIM]NTf2 > [BMIM]OTf > [BMIM]PF6 > [BMIM]BF4. Especially, [BMIM]FeCl4 ionic liquid had excellent removal efficiency for DBDS, with its S partition coefficient KN (S) being up to 2642, which was much higher than the other eight imidazolium-based ILs. Moreover, the extractive performance of [BMIM]FeCl4 increased with an increasing molar ratio of FeCl3 to [BMIM]Cl, which was attributed to its Lewis acidity and fluidity. [BMIM]FeCl4 ionic liquid could also avail in the desulfurization of diphenyl sulfide (DPS) from model oils. The experimental results demonstrate that π-π action, π-complexation, and Lewis acid-base interaction played important roles in the desulfurization process. Finally, the ([BMIM]FeCl4) ionic liquid could be recycled five times without a significant decrease in extractive ability.

Addition of Imidazolium-Based Ionic Liquid to Improve Methanol Production in Polyamine-Assisted CO2 Capture and Conversion Systems Using Pincer Catalysts.

Ionic liquids have been studied as CO2 capture agents. However, they are rarely used in combined CO2 capture and conversion processes. Utilizing imidazolium-based ionic liquids, the conversion of CO2 to methanol was greatly improved in polyamine assisted systems catalyzed by homogeneous pincer catalysts with Ru and Mn metal centers. Among the ionic liquids tested, [BMIM]OAc was found to perform the best under the given reaction conditions. Among the polyamine tested, pentaethylenehexamine (PEHA) led to the highest conversion rates. Ru-Macho and Ru-Macho-BH were the most active catalysts. Direct air capture utilizing PEHA as the capture material was also demonstrated and produced an 86 % conversion of the captured CO2 to methanol in the presence of [BMIM]OAc.

Atomistic molecular dynamics simulation and COSMO-SAC approach for enhanced 1,3-propanediol extraction with imidazolium-based ionic liquids.

1,3-Propanediol (1,3-PDO) is a key chemical in various industries, including pharmaceuticals and material sciences, and is projected to see significant market growth. However, the current challenges in its downstream processing, particularly in terms of cost and efficiency, highlight the need for innovative solutions. Our study delves into using ionic liquids (ILs) as a potential alternative, aiming to address these critical separation challenges more sustainably and efficiently. In this study, we utilized molecular dynamics (MD) simulations and the COSMO-SAC to examine 1,3-propanediol (1,3-PDO) extraction using four imidazolium-based ionic liquids with 1-butyl-3-methylimidazolium [Bmim] cation and with different anions bis(pentafluoroethanesulfonyl)imide [NPF2]-, bis(trifluoromethylsulfonyl)imide [NTF2]-, thiocyanate [SCN]-, and trifluoromethanesulfonate [TFO]-. Molecular dynamics simulations, incorporating analysis of radial distribution functions (RDF) and spatial distribution functions (SDF), revealed that [Bmim][SCN] and [Bmim][TFO] exhibit enhanced interactions with 1,3-PDO. Notably, [Bmim][SCN] formed the most hydrogen bonds, averaging 1.639 per molecule, due to its coordinating [SCN]- anion. This was in contrast to the fewer hydrogen bonds formed by non-coordinating anions in [Bmim][NPF2] and [Bmim][NTF2]. In ternary systems, [Bmim][SCN] and [Bmim][TFO] demonstrated superior selectivity for 1,3-PDO extraction compared to the other ionic liquids, with selectivity values around 29. These findings, supported by COSMO-SAC predictive modeling, highlight the potential of [Bmim][SCN] as a promising candidate for 1,3-PDO extraction, emphasizing the importance of anion selection in optimizing ionic liquid properties for this application. In our study, we employed MD simulations, incorporating the OPLS-AA force field, and COSMO-SAC to investigate the extraction of 1,3-PDO using imidazolium-based ionic liquids: [Bmim][NTF2], [Bmim][NPF2], [Bmim][SCN], and [Bmim][TFO]. The MD simulations were conducted using LAMMPS software, focusing on elucidating the RDF, SDF, and hydrogen bonding. Analysis of the distribution coefficient (β) and selectivity (S) for the ternary mixture was also conducted. These aspects of the simulation were analyzed using TRAVIS and VMD software. Additionally, the COSMO-SAC model was employed to determine the activity coefficients of 1,3-PDO in the ionic liquids, with molecular optimization conducted using Gaussian16 and sigma profile calculations performed using COSMO-SAC.

Role of ionic liquids in ibuprofen-based eutectic systems: Aqueous solubility, permeability, human cytotoxicity, hemolytic activity and anti-inflammatory activity

Eutectic systems, as well as ionic liquids (ILs), offer a potential solution to the challenges associated with low solubility, polymorphism, and limited bioavailability of active pharmaceutical ingredients (APIs). Herein, we prepared twelve pharmaceutically active eutectics based on ibuprofen (Ibu), a widely accessible without prescription non-steroidal anti-inflammatory drug (NSAID), and imidazolium-based ILs ([C2C1Im]Cl, [C2(OH)C1Im]Cl and [C2C1Im][C1CO2]) and cholinium salt ([N1112(OH)]Cl) at different molar ratio (2:1, 1:1, 1:2 and 1:5). All eutectic systems were characterized by DSC and NMR, and their polarity was assessed using the Kamlet-Taft approach to characterize the non-specific (polarity/polarizability) and specific (hydrogen bonding ability) interactions. An upgrade of the aqueous solubility (water and biological simulated fluids) for the Ibu-based eutectics relatively to ibuprofen was verified. Also, the assessment of ionicity (viscosity, conductivity, and density) was attained, confirming the formation of ion-pairs or clusters, that increase the potential of these liquids to be more membrane diffusive. The biocompatibility of the Ibu-based eutectics was evaluated up to 3 mM (well above the ibuprofen maximum plasma concentration) through a hemolytic activity assay and in vitro cytotoxicity as-says with two human cell lines (Caco-2 colon carcinoma cells and HepG2 hepatocellular carcinoma cells), without impairing their hemolytic and cytotoxic response. Additionally, the anti-inflammatory activity was evaluated by the inhibition of bovine serum albumin (BSA) denaturation and inhibition of cyclooxygenases (COX-1 and COX-2) enzymes, showing that the ibuprofen eutectic formulations maintain the anti-inflammatory response of ibuprofen with the opportunity to improve the selectivity towards COX-2, allowing the development of safer NSAIDs.

Beta-Irradiation of pure 1-alkyl-3-methylimidazolium-based ionic liquids

1-Alkyl-3-methylimidazolium ionic liquids are common cellulose solvents and biomass pretreatment agents, while beta-irradiation (“e-beaming”) is often used to decrease the recalcitrance of biomass towards hydrolysis or saccharification. Aiming at the general goal of elucidating the interaction between lignocellulosics, imidazolium-based ionic liquids, and beta-irradiation, we studied the effect of beta-irradiation on the pure ILs 1-ethyl-3-methylimidazolium and 1-butyl-3-methylimidazolium, both as chloride and acetate. Contrary to the expectation of inertness, irradiation caused degradation of the ILs, which was proportional to irradiation dosage, i.e., to irradiation time and intensity. At a dosage of 2400 kGy, 0.2% (2000 ppm) of the IL were chemically altered. The main degradation pathway is the formation of imidazole and N-methylimidazole with concomitant dealkylation. The cleaved-off alkyl groups, apparently in cationic form, react with the anions present, accounting for the formation of alkyl chlorides and alkyl acetates from the chloride ILs and acetate ILs, respectively. A second, minor pathway comprises the degradation of the imidazole ring under conversion of the C2-unit from the former C4-C5 moiety into ethylenediamine and reaction of the C1-unit from the former C2 with the IL anions. Because of the non-neglible byproduct formation, the degradation of the ILs upon beta-irradiation and possible side reactions of the resulting byproducts need to be kept in mind for all setups that involve beta-irradiation and imidazolium ILs simultaneously.Graphical abstract

Incorporating porous carbon materials into ionic liquid for high efficiency extraction of polycyclic aromatic hydrocarbons

Ionic liquid is an ideal candidate in the extraction of aromatic compounds. The design and construction of ionic liquids with high extraction efficiency and selectivity towards to the specific aromatics remain crucial question. In this paper, with the aid of orthogonal array experiment, the imidazolium-based ionic liquids with long alkyl chain on the cations were determined to possess high aromatics extraction efficiency. Furthermore, the Lewis acid anion was introduced into the ionic liquid to form 1-dodecyl-3-methylimidazolium ferric chloride ([C12mim][FeCl4]) and performed 62 % and 100 % extractant efficiency of naphthalene (NAP) and anthracene (ANT), respectively. Then the porous carbon materials (P1-1000) derived from hyper-crosslinked porous polymers (HCP) which possessed high BET surface area (1186 m2/g) was dispersed in [C12mim][FeCl4] to form porous ionic liquid. The single extraction efficiency of NAP improved from 62 % to 77 %. The great single extraction efficiency was attributed to the high porosity, additional adsorption sites provided by the Lewis acid anions and the hydrophobic long alkyl chain on the cations. After three times extraction, the concentration of NAP dropped down to 0. The porous ionic liquids also showed good recycle performance. The construction of porous ionic liquids provided an efficient approach for extraction of polycyclic aromatic hydrocarbons from aliphatic hydrocarbon.