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Insight into the Hydration of Cationic Surfactants: A Thermodynamic and Dielectric Study of Functionalized Quaternary Ammonium Chlorides

Hydrophobic interactions are one of the main thermodynamic driving forces in self-assembly, folding, and association processes. To understand the dehydration-driven solvent exposure of hydrophobic surfaces, the micellization of functionalized decyldimethylammonium chlorides, XC10Me2N+Cl-, with a polar functional group, X = C2OH, C2OMe, C2OC2OMe, C2OOEt, together with the "reference" compound decyltrimethylammonium chloride, C10Me3N+Cl-, was investigated in aqueous solution by density measurements, isothermal titration calorimetry (ITC), and dielectric relaxation spectroscopy (DRS). From the density data, the apparent molar volumes of monomers and micelles were estimated, whereas the ITC data were analyzed with the help of a model equation, yielding the thermodynamic parameters and aggregation number. From the DRS spectra, effective hydration numbers of the free monomers and micelles were deduced. The comprehensive analysis of the obtained results shows that the thermodynamics of micellization are strongly affected by the nature of the functional group. Surprisingly, the hydration of micelles formed by surfactant cations with a single alkyl chain on quaternary ammonium is approximately the same, regardless of the alkyl chain length or functionalization of the headgroup. However, notable differences were found for the free monomers where increasing polarity lowers the effective hydration number

Correction: Carbon dioxide uptake from natural gas by binary ionic liquid–water mixtures

Correction for ‘Carbon dioxide uptake from natural gas by binary ionic liquid–water mixtures’ by Kris Anderson et al., Green Chem., 2015, DOI: 10.1039/c5gc00720h

Physicochemical Characterization of Ionic Liquid Binary Mixtures Containing 1-Butyl-3-methylimidazolium as the Common Cation

FCT/MEC (Portugal), through "Investigador FCT 2014" (IF/00190/2014 to A.B.P and IF/00210/2014 to J.M.M.A.),; Projects PTD C/EQU-EQU/29737/2017; PTDC/QEQFTT/32,89/2014; IF/00210/2014/CP1244/CT0003. This work was also supported by the Associate Laboratory for Green Chemistry LAQV (financed by national funds from FCT/MCTES (UID/QUI/50006/2019)) and cofinanced by the ERDF under the PT2020 Partnership Agreement (POCI-01-0145-FEDER-007265).Mixing ionic liquids (as well as mixing an inorganic salt in an ionic liquid) constitutes an easy, elegant methodology for obtaining new ionic materials. In this study, 3 ionic liquids (ILs) sharing a common cation were synthesized and mixed in 9 different proportions giving rise to 27 binary mixtures. Specifically, 1-butyl-3-methylimidazolium nitrate, [C4C1Im][NO3], 1-butyl-3-methylimidazolium chloride, [C4C1Im]Cl, and 1-butyl-3-methylimidazolium methanesulfonate, [C4C1Im][CH3SO3], were synthesized and characterized. They all share 1-butyl-3-methylimidazolium as the common archetypal cation. None of them (or any of their binary mixtures) is liquid at room temperature (T = 298.15 K), and two of them are only in the liquid state above temperatures of 343-353 K. Despite belonging to commonly used families of ILs, their handling and the study of their liquid properties (neat and mixtures) have become particularly difficult, mainly because of their tendency to solidify and their high viscosity (caused by hydrogen-bonded networks). The main goal of this work is to evaluate the thermal, dynamic, and volumetric properties of these compounds and their mixtures as well as the solid-liquid equilibria of their binary mixtures. Thermal properties, such as melting and glass-transition temperatures, were determined or calculated. Therefore, both density and viscosity have been measured and were used for the calculation of the isobaric thermal expansion coefficient, molar volumes, excess molar volumes, and viscosity deviations to linearity.authorsversionpublishe

Ionic Liquids–Cobalt(II) Thermochromic Complexes: How the Structure Tunability Affects “Self-Contained” Systems

With the aim of obtaining thermochromic systems with potential applications in solar energy storage, we evaluated the behavior of some sugar-based ionic liquids (ILs) 12Co(NTf2)2 complexes, in IL solution, as a function of temperature. Different structural changes on the cation, the nature of the anion, and the nature of the IL used as the solvent were considered. The analysis of the above factors was carried out through a combined approach of different techniques, that is, variable temperature UV 12vis and NMR spectroscopies, conductivity, and thermal gravimetric analysis. The thermochromic systems were analyzed both as solutions and as thin films, and the data collected highlight the defining role played by both the cation structure and the solvent nature in determining their performance. Most of the investigated systems show a chromogenic transition from pink to blue, occurring in a temperature range suitable for practical applications (40 1260 \ub0C). Interestingly, when embedded in a polymeric matrix, thin films with high recyclability and long life are also described

Carbon dioxide uptake from natural gas by binary ionic liquid water mixtures

[EN] Carbon dioxide solubility in a set of carboxylate ionic liquids formulated with stoicheiometric amounts of water is found to be significantly higher than for other ionic liquids previously reported. This is due to synergistic chemical and physical absorption. The formulated ionic liquid/water mixtures show greatly enhanced carbon dioxide solubility relative to both anhydrous ionic liquids and aqueous ionic liquid solutions, and are competitive with commercial chemical absorbers, such as activated N-methyldiethanolamine or monoethanolamine.The authors would like to acknowledge PETRONAS for financial support of this research, and Cytec (especially Dr Al Robertson) for supplying some of the phosphonium ionic liquids used.Anderson, K.; Atkins, MP.; Estager, J.; Kuah, Y.; Ng, S.; Oliferenko, AA.; Plechkova, NV.... (2015). Carbon dioxide uptake from natural gas by binary ionic liquid water mixtures. 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G.Compton and C.Hardacre, Chloride Determination in Ionic Liquids, in Ionic Liquids IIIB: Fundamentals, Progress, Challenges, and Opportunities - Transformations and Processes, ed. R. D. Rogers and K. R. Seddon, ACS Symp. Ser., Vol. 902, American Chemical Society, Washington D.C., 2005, vol. 902, pp. 244–258J. L. Anthony , E. J.Maginn and J. F.Brennecke, Gas Solubilities in 1-n-Butyl-3-methylimidazolium Hexafluorophosphate, in Ionic Liquids: Industrial Applications to Green Chemistry, ed. R. D. Rogers and K. R. Seddon, ACS Symp. Ser, Vol. 818, American Chemical Society, Washington D.C., 2002, vol. 818, pp. 260–269J. H. Davis Jr. , Working Salts: Syntheses and Uses of Ionic Liquids Containing Functionalized Ions, in Ionic Liquids: Industrial Applications to Green Chemistry, ed. R. D. Rogers and K. R. Seddon, ACS Symp. Ser, Vol. 818, American Chemical Society, Washington D.C., 2002, vol. 818, pp. 247–259Bates, E. D., Mayton, R. D., Ntai, I., & Davis, J. H. (2002). CO2Capture by a Task-Specific Ionic Liquid. Journal of the American Chemical Society, 124(6), 926-927. doi:10.1021/ja017593dWang, C., Luo, X., Zhu, X., Cui, G., Jiang, D., Deng, D., … Dai, S. (2013). The strategies for improving carbon dioxide chemisorption by functionalized ionic liquids. RSC Advances, 3(36), 15518. doi:10.1039/c3ra42366bRamdin, M., de Loos, T. W., & Vlugt, T. J. H. (2012). State-of-the-Art of CO2Capture with Ionic Liquids. Industrial & Engineering Chemistry Research, 51(24), 8149-8177. doi:10.1021/ie3003705Zhang, X., Zhang, X., Dong, H., Zhao, Z., Zhang, S., & Huang, Y. (2012). Carbon capture with ionic liquids: overview and progress. Energy & Environmental Science, 5(5), 6668. doi:10.1039/c2ee21152aYokozeki, A., & Shiflett, M. B. (2009). Separation of Carbon Dioxide and Sulfur Dioxide Gases Using Room-Temperature Ionic Liquid [hmim][Tf2N]. Energy & Fuels, 23(9), 4701-4708. doi:10.1021/ef900649cCabaço, M. I., Besnard, M., Danten, Y., & Coutinho, J. A. P. (2012). Carbon Dioxide in 1-Butyl-3-methylimidazolium Acetate. I. Unusual Solubility Investigated by Raman Spectroscopy and DFT Calculations. The Journal of Physical Chemistry A, 116(6), 1605-1620. doi:10.1021/jp211211nCarvalho, P. J., Álvarez, V. H., Schröder, B., Gil, A. M., Marrucho, I. M., Aznar, M., … Coutinho, J. A. P. (2009). Specific Solvation Interactions of CO2on Acetate and Trifluoroacetate Imidazolium Based Ionic Liquids at High Pressures. The Journal of Physical Chemistry B, 113(19), 6803-6812. doi:10.1021/jp901275bGoodrich, B. F., de la Fuente, J. C., Gurkan, B. E., Zadigian, D. J., Price, E. A., Huang, Y., & Brennecke, J. F. (2011). Experimental Measurements of Amine-Functionalized Anion-Tethered Ionic Liquids with Carbon Dioxide. Industrial & Engineering Chemistry Research, 50(1), 111-118. doi:10.1021/ie101688aGoodrich, B. F., de la Fuente, J. C., Gurkan, B. E., Lopez, Z. K., Price, E. A., Huang, Y., & Brennecke, J. F. (2011). Effect of Water and Temperature on Absorption of CO2by Amine-Functionalized Anion-Tethered Ionic Liquids. The Journal of Physical Chemistry B, 115(29), 9140-9150. doi:10.1021/jp2015534Ferguson, J. L., Holbrey, J. D., Ng, S., Plechkova, N. V., Seddon, K. R., Tomaszowska, A. A., & Wassell, D. F. (2011). A greener, halide-free approach to ionic liquid synthesis. Pure and Applied Chemistry, 84(3), 723-744. doi:10.1351/pac-con-11-07-21Shiflett, M. B., Kasprzak, D. J., Junk, C. P., & Yokozeki, A. (2008). Phase behavior of {carbon dioxide+[bmim][Ac]} mixtures. The Journal of Chemical Thermodynamics, 40(1), 25-31. doi:10.1016/j.jct.2007.06.003Shiflett, M. B., & Yokozeki, A. (2009). Phase Behavior of Carbon Dioxide in Ionic Liquids: [emim][Acetate], [emim][Trifluoroacetate], and [emim][Acetate] + [emim][Trifluoroacetate] Mixtures. Journal of Chemical & Engineering Data, 54(1), 108-114. doi:10.1021/je800701jShiflett, M. B., Drew, D. W., Cantini, R. A., & Yokozeki, A. (2010). Carbon Dioxide Capture Using Ionic Liquid 1-Butyl-3-methylimidazolium Acetate. Energy & Fuels, 24(10), 5781-5789. doi:10.1021/ef100868aCabaço, M. I., Besnard, M., Danten, Y., & Coutinho, J. A. P. (2011). Solubility of CO2in 1-Butyl-3-methyl-imidazolium-trifluoro Acetate Ionic Liquid Studied by Raman Spectroscopy and DFT Investigations. The Journal of Physical Chemistry B, 115(13), 3538-3550. doi:10.1021/jp111453aGurau, G., Rodríguez, H., Kelley, S. P., Janiczek, P., Kalb, R. S., & Rogers, R. D. (2011). Demonstration of Chemisorption of Carbon Dioxide in 1,3-Dialkylimidazolium Acetate Ionic Liquids. Angewandte Chemie International Edition, 50(50), 12024-12026. doi:10.1002/anie.201105198Besnard, M., Cabaço, M. I., Vaca Chávez, F., Pinaud, N., Sebastião, P. J., Coutinho, J. A. P., … Danten, Y. (2012). CO2 in 1-Butyl-3-methylimidazolium Acetate. 2. NMR Investigation of Chemical Reactions. The Journal of Physical Chemistry A, 116(20), 4890-4901. doi:10.1021/jp211689zJaniczek, P., Kalb, R. 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Alkyltributylphosphonium chloride ionic liquids: synthesis, physicochemical properties and crystal structure. Dalton Transactions, 41(27), 8316. doi:10.1039/c1dt10466gM. B. Shiflett and A.Yokozeki, Phase Behaviour of Gases in Ionic Liquids, in Ionic Liquids UnCOILed: Critical Expert Overviews, ed. N. V. Plechkova and K. R. Seddon, Wiley, Hoboken, New Jersey, 2013, pp. 349–398Ibrahim, A. Y., Ashour, F. H., Ghallab, A. O., & Ali, M. (2014). Effects of piperazine on carbon dioxide removal from natural gas using aqueous methyl diethanol amine. Journal of Natural Gas Science and Engineering, 21, 894-899. doi:10.1016/j.jngse.2014.10.011Anonymous , Piperazine – Why It's Used And How It Works, The Contractor (Optimized Gas Treating, Inc.), Houston, 2008, 2 [4], http://www.ogtrt.com/files/contactors/vol_2_issue_4.pd

Mycobiota of silk-faced ancient Mogao Grottoes manuscripts belonging to the Stein collection in the British library

Silking, a conservation technique which involved gluing silk gauze over the face of a manuscript was popular in the mid-20th Century, especially for treating early Chinese documents. The method is now little used, and the question as to whether silking interventions should be reversed is controversial, given the high economic cost of active intervention, and there are few scientific studies as to the long-term consequences of the technique. Silk-facing materials from documents of the Stein collection were analysed using scanning electron microscopy coupled with energy dispersive X-ray spectroscopy. The mycobiota diversity was unravelled through the combination of culture dependent methods and amplicon sequencing analyses. The SEM micrographs showed smooth regular nodules of ca. 3–5 μm diameter on both silk threads and glue paste. This morphology differs from the irregular and the crystalline morphologies of glue paste and inorganic crystallites, respectively, but it is consistent with that of small-sized conidia (asexual spores of fungi) or yeasts. Glue paste demonstrated three fungal strains: Aspergillus tubingensis, Penicillium crustosum and Chrysonilia sitophila which display cellulolytic activity, except for the last one. Amplicon sequencing revealed that silk threads and glue paste host distinct mycobiota. Here, we preliminary show that the silking method may be affecting the overall integrity of the silk-faced manuscripts, principally due to contamination with cellulolytic fungal strains. Unless the silk facing is removed, irreversible damage to the documents is highly probable

Structure and dynamics in protic ionic liquids: a combined optical Kerr-effect and dielectric relaxation spectroscopy study

The structure and dynamics of ionic liquids (ILs) are unusual due to the strong interactions between the ions and counter ions. These microscopic properties determine the bulk transport properties critical to applications of ILs such as advanced fuel cells. The terahertz dynamics and slower relaxations of simple alkylammonium nitrate protic ionic liquids (PILs) are here studied using femtosecond optical Kerr-effect spectroscopy, dielectric relaxation spectroscopy, and terahertz time-domain spectroscopy. The observed dynamics give insight into more general liquid behaviour while comparison with glass-forming liquids reveals an underlying power-law decay and relaxation rates suggest supramolecular structure and nanoscale segregation