4303-67-7Relevant academic research and scientific papers
Aggregation behavior of zwitterionic surface active ionic liquids with different counterions, cations, and alkyl chains
Sun, Panpan,Shi, Lijuan,Lu, Fei,Zheng, Liqiang
, p. 27370 - 27377 (2016)
A group of zwitterionic surface active ionic liquids (SAILs) with different counterions, cations and alkyl chains, 3-(1-alkyl-3-imidazolio)propanesulfonate β-naphthalene sulfonate, (CnIPS-Nsa, n = 12, 14), 3-(1-dodecyl-3-imidazolio)propanesulfonate benzenesulfonate (C12IPS-Bsa), and dodecyl-N,N-dimethylammonio-3-propane sulfonate β-naphthalene sulfonate (SB-12-Nsa), were synthesized. Their aggregation behaviors in aqueous solutions were systematically investigated by surface tension, dynamic light scattering (DLS) and 1H NMR spectroscopy. Surface tension and DLS results illustrated that the surface properties, micelle size, and micellization behavior of zwitterionic SAILs in aqueous solutions are significantly affected by the anion type, anionic structure and the hydrophobicity of the alkyl chain. The SAILs with more hydrophobic anions and long alkyl chains are expected to favor the micellization. The steric hindrance and hydrophobicity of the cations, as well as the binding strength of the cations with the anions, also play important roles in the aggregation of zwitterionic SAILs. Additionally, the micelle formation mechanism was acquired by detailed analysis of the 1H NMR spectra. The existence of π-π stacking between imidazolium and counterions was proved. The enhanced π-π stacking and hydrophobic effect of Nsa- can promote the aggregation of zwitterionic SAILs. Density functional theory (DFT) calculations illustrated that the negative interaction energy of the complexes were C12IPS-Bsa/H2O > SB-12-Nsa/H2O > C12IPS-Nsa/H2O > C14IPS-Nsa/H2O. It is more difficult to form micelles in complexes with more negative interaction energy. The counterion electronegativity of Nsa- is smaller than that of Bsa-, which favors the formation of micelles.
Supernucleophilic systems based on functionalized surfactants in the decomposition of 4-nitrophenyl esters derived from phosphorus and sulfur acids: I. Reactivity of a hydroxyimino derivative of gemini imidazolium surfactant
Kapitanov,Belousova,Shumeiko,Kostrikin,Prokop'Eva,Popov
, p. 1291 - 1299 (2013)
A new functionalized gemini surfactant, 3,3′-[2-(hydroxyimino) propane-1,3-diyl]bis(1-dodecyl-1H-imidazol-3-ium) dichloride, and its non-micelle-forming methyl analog, were synthesized. Nucleophilicity of the oximate group in these compounds in the decomposition of 4-nitrophenyl esters derived from phosphorus and sulfur acids follows Bronsted relations for monomeric functionalized surfactants and non-micelle-forming oximes. As compared to the single-chained analog, the gemini surfactant ensured the same observed rate of substrate decomposition at lower concentration and lower pH. Micellar effects of the gemini surfactant in these reactions attain a value of ～103 and are determined mainly by substrate concentration in the micellar pseudophase.
Synthesis and assessment of new cationic gemini surfactants as inhibitors for carbon steel corrosion in oilfield water
El-Taib Heakal,Deyab,Osman,Nessim,Elkholy
, p. 47335 - 47352 (2017)
Three gemini surfactants were synthesized having the same length of terminal chain but differing in the spacer chain length and they were evaluated as corrosion inhibitors for carbon steel in oilfield water using weight loss, EIS, potentiodynamic polarization and open-circuit potential measurements. These measurements revealed that the synthesized materials have served as effective mixed-type corrosion inhibitors. Their adsorption on a carbon steel surface was well described by means of the Langmuir adsorption isotherm. The activation parameters for the dissolution of carbon steel in solutions of oilfield water in the absence and presence of these inhibitors were calculated. The effect of immersion time on the stability and durability of protective films adsorbed on a carbon steel surface was studied using weight loss method. Ex situ inspection, i.e. post-exposure analysis, for the treated carbon steel surface has been performed using SEM, EDX and FT-IR tools.
Ionic conduction and dielectric response of poly(imidazolium acrylate) ionomers
Choi, U Hyeok,Lee, Minjae,Wang, Sharon,Liu, Wenjuan,Winey, Karen I.,Gibson, Harry W.,Colby, Ralph H.
, p. 3974 - 3985 (2012)
We use X-ray scattering to investigate morphology and dielectric spectroscopy to study ionic conduction and dielectric response of imidazolium-based single-ion conductors with two different counterions [hexafluorophosphate (PF6-) or bis(trifluoromethanesulfonyl)imide (F3CSO2NSO 2CF3- = Tf2N-)] with different imidazolium pendant structures, particularly tail length (n-butyl vs n-dodecyl). A physical model of electrode polarization is used to separate ionic conductivity of the ionomers into number density of conducting ions and their mobility. Tf2N- counterions display higher ionic conductivity and mobility than PF6- counterions, as anticipated by ab initio calculations. Ion mobility is coupled to polymer segmental motion, as these are observed to share the same Vogel temperature. Ionomers with the n-butyl tail impart much larger static dielectric constant than those with the n-dodecyl tail. From the analysis of the static dielectric constant using Onsager theory, there is more ionic aggregation in ionomers with the n-dodecyl tails than in those with the n-butyl tails, consistent with X-ray scattering, which shows a much stronger ionic aggregate peak for the ionomers with dodecyl tails on their imidazolium side chains.
Synthesis of dicationic alkyl imidazolium peroxopolyoxotungsten-based phase transfer catalyst and its catalytic activity for olefin epoxidation
Wu, Jianghao,Jiang, Pingping,Leng, Yan,Ye, Yuanyuan,Qin, Xiaojie
, p. 2236 - 2244 (2013)
Peroxopolyoxotungsten-based hybrid catalysts modified by dicationic long-chain alkyl imidazolium cations have been synthesized and characterized. The catalytic activity of the catalysts was measured for the epoxidation of olefins with H2O2. These catalysts proved to be high catalytic activity phase transfer catalysts. In particular, for the catalyst [D12min]1.5PW4O24 modified by the dodecyl dicationic imidazolium cation, the conversion of cyclohexene and selectivity for epoxycyclohexane were 97.7% and 96.3%, respectively. After the reaction, the catalyst could be recovered simply by filtration and reused four times. The conversion of cyclohexene and selectivity for epoxycyclohexane were still 72.4% and 97.2%, respectively, after recycling the catalyst four times. In addition, this phase transfer catalyst can be applied to the epoxidation of a wide range of olefins.
Synthesis of triethoxysilane imidazolium based ionic liquids and their application in the preparation of mesoporous ZSM-5
Kore, Rajkumar,Srivastava, Rajendra
, p. 11 - 15 (2012)
Triethoxysilane containing imidazole based ionic liquids were synthesized. These ionic liquids were utilized as a structure directing agent for the synthesis of mesoporous ZSM-5. ZSM-5 was characterized by a complementary combination of X-ray diffraction, N2 adsorption/desorption, Scanning electron microscopy, Transmission electron microscopy, Temperature programmed desorption techniques, Infrared spectroscopy and Nuclear Magnetic Resonance spectroscopy. The resultant zeolites were mesoporous and showed unique characteristics of a fully crystalline microporous MFI zeolite framework. Mesoporous ZSM-5 synthesized from imidazole based ionic liquids exhibited higher catalytic activity than conventional ZSM-5 in alkylation and cracking reactions. Significantly high catalytic activity of the mesoporous ZSM-5 suggests that large external surface area and accessible acid sites are beneficial for catalytic reactions involving large organic molecules.
1,2-Bis[N-(N′-alkylimidazolium)]ethane salts as new guests for crown ethers and cryptands
Lee, Minjae,Niu, Zhenbin,Schoonover, Daniel V.,Slebodnick, Carla,Gibson, Harry W.
, p. 7077 - 7082 (2010)
1,2-Bis[N-(N′-alkylimidazolium)ethane salts form complexes presumed to be pseudorotaxanes with crown ether and cryptand hosts. The association constants of 1,2-bis[N-(N′-butylimidazolium)]ethane bis(hexafluorophosphate) with dibenzo-24-crown-8 and a dibenzo-24-crown-8-based pyridyl cryptand were estimated as 24 (±1) and 348 (±30) M -1, respectively, in acetonitrile at 25 °C. The pseudorotaxane-like structure of the 1:2 complex of the N′-methyl analog with the cryptand was observed by X-ray crystallography. Replacement of the ethylene spacer with propylene and butylene spacers resulted in Ka values an order of magnitude smaller.
The structure – Activity correlation in the family of dicationic imidazolium surfactants: Antimicrobial properties and cytotoxic effect
Gumerova, Syumbelya K.,Kotenko, Alla A.,Kulik, Natalia V.,Mikhailov, Vasilii A.,Mirgorodskaya, Alla B.,Prokopyeva, Tatiana M.,Sapunova, Аnastasiia S.,Sinyashin, Oleg G.,Voloshina, Alexandra D.,Zakharova, Lucia Ya
, (2020)
Background: The development of new effective microbicide surfactants and the search for the structure–biological activity relationship is an important and promising problem. Surfactants containing imidazolium fragment attract attention of researchers in the field of chemotherapy, because these compounds often exhibit high antimicrobial activity. The aim of this work is to identify the newly synthesized surfactants from the viewpoint of their potential usefulness in pharmacology and medicine. For this purpose, a detailed study of antimicrobial, hemolytic and cytotoxic activity of dicationic alkylimidazolium surfactants of the m-s-m (Im) series with a variable length of a hydrocarbon tail (m = 10, 12) and a spacer fragment (s = 2, 3, 4) was carried out. Methods: Aggregation of surfactants in solutions was estimated by tensiometry and conductivity. Antimicrobial activity was determined by the serial dilution technique. Cytotoxic effects of the test compounds on human cancer and normal cells were estimated by means of the multifunctional Cytell Cell Imaging system. Cell Apoptosis Analysis was made by flow cytometry. Results: The test compounds show high antimicrobial activity against a wide range of test microorganisms and do not possess high hemolytic activity. Importantly, some of them display a bactericidal activity comparable to ciprofloxacin fluoroquinolone antibiotic against Gram-positive bacteria, including methicillin-resistant strains of S. aureus (MRSA). The cytotoxicity of the compounds against normal and tumor human cell lines has been tested as well, with cytotoxic effect and selectivity strongly controlled by structural factor and kind of cell line. Superior results were revealed for compound 10–4-10 (Im) in the case of HuTu 80 cell line (duodenal adenocarcinoma), for which IC50 value at the level of doxorubicin and a markedly higher selectivity index (SI 7.5) were demonstrated. Flow cytometry assay shows apoptosis-inducing effect of this compound on HuTu 80 cells, through significant changes in the potential of mitochondrial membrane. Major conclusions: Antibacterial properties are shown to be controlled by alkyl chain length, with the highest activity demonstrated by surfactants with decyl tail, with the length of the spacer fragment showing practically no effect. The results indicate that the mechanism of cytotoxic effect of the compounds can be associated with the induction of apoptosis via the mitochondrial pathway. General significance: Selectivity against pathogenic microorganisms and low toxicity against eukaryotic cells allow considering dicationic imidazolium surfactants as new effective antimicrobial agents. At the same time, high selectivity against some cancer cell lines indicates the prospect of their using as components of new anticancer drugs.
Mono and co-immobilization of imidazolium ionic liquids on silica: Effects of the substituted groups on the adsorption behavior of 2,4-dinitrophenol
Wang, Zhike,Ge, Honglian,Wang, Xueyuan,Ye, Cunling,Fan, Shunli
, p. 32425 - 32434 (2019)
Ionic liquid modified silicas with high adsorption capacity for phenols prompt us to deeply explore the contribution of interactions between the adsorbent and adsorbate, with a particular focus on hydrophobicity, π-π, electrostatic and acid-base interactions. Herein, by introducing a series of typical substituent groups including N,N-dimethylaminopropyl (A), benzyl (B), dodecyl (D) and naphthylmethyl (N) in an imidazole ring (Im), three mono-immobilized and two co-immobilized imidazolium ionic liquid modified silicas, namely SilprAImCl, SilprBImCl, SilprNImCl, SilprDBImCl and SilprDAImCl, werre synthesized for removal and recovery of 2,4-dinitrophenol (2,4-DNP) from aqueous solutions. Adsorption kinetics, isotherms, thermodynamic analysis and desorption experiments have been carried out. The experimental results reveal that the substituent groups such as N,N-dimethylaminopropyl, benzyl and naphthylmethyl on the imidazole ring can significantly enhance the adsorption of 2,4-DNP via the acid-base interaction or π-π interaction and the adsorption capacity of 2,4-DNP follows the order: SilprNImCl > SilprAImCl > SilprBImCl. Furthermore, SilprDBImCl exhibits the largest adsorption capacity and SilprDAImCl has the lowest among the five adsorbents. These interesting finds indicate that the combination of hydrophobicity and π-π interactions lead to enhanced adsorption performance towards 2,4-DNP, while the combination of the hydrophobicity and acid-base interactions can restrain greatly adsorption of 2,4-DNP from aqueous medium. Adsorption mechanisms of 2,4-DNP on the five adsorbents have been clarified. These results will provide a deeper insight for efficient removal of phenols from water environments.
Ruthenium complex immobilized on supported ionic-liquid-phase (SILP) for alkoxycarbonylation of olefins with CO2
Xia, Shi-Ping,Ding, Guang-Rong,Zhang, Rui,Han, Li-Jun,Xu, Bao-Hua,Zhang, Suo-Jiang
supporting information, p. 3073 - 3080 (2021/05/05)
In this study, the heterogeneously catalyzed alkoxycarbonylation of olefins with CO2based on a supported ionic-liquid-phase (SILP) strategy is reported for the first time. An [Ru]@SILP catalyst was accessed by immobilization of ruthenium complex on a SILP, wherein imidazolium chloride was chemically integrated at the surface or in the channels of the silica gel support. An active Ru site was generated through reacting Ru3(CO)12with the decorated imidazolium chloride in a proper microenvironment. Different IL films, by varying the functionality of the side chain at the imidazolium cation, were found to strongly affect the porosity, active Ru sites, and CO2adsorption capacity of [Ru]@SILP, thereby considerably influencing its catalytic performance. The optimized [Ru]@SILP-A-2 displayed enhanced catalytic performance and prominent substrate selectivity compared to an independent homogeneous system under identical conditions. These findings provide the basis for a novel design concept for achieving both efficient and stable catalysts in the coupling of CO2with olefins.
