Liquid-Liquid equilibria of ternary mixtures of alkane (C8 or C12) + thiophene + three methylimidazolium dicyanamide (DCA)-based ionic liquids

Chemical Thermodynamics and Thermal Analysis - Tập 10 - Trang 100112 - 2023
Adel F. Alenzi1, Khaled H.A.E. Alkhaldi1, Adel S. Al-Jimaz1, Mohammad S. AlTuwaim1
1Chemical Engineering Department, College of Technological Studies, PAAET, P.O. Box 42325, Shuwaikh 70654, Kuwait

Tài liệu tham khảo

Van, 2019, Global impacts of recent IMO regulations on marine fuel oil refining processes and ship emissions, Transp. Res. D Transp. Environ., 70, 123, 10.1016/j.trd.2019.04.001 Holbrey, 1999, Ionic liquids, Fukugo Biseibutsukei no Sangyo Riyo to Shinsangyo Soshutsu, 1, 223 Chauvin, 1995, Nonaqueous ionic liquids as reaction solvents, ChemTech, 25, 26 Chauvin, 1996, Two-phase catalysis in nonaqueous ionic liquids, Actual. Chim., 44 Freemantle, 1998, Designer solvents – Ionic liquids may boost clean technology development, Chem. Eng. News., 76, 32, 10.1021/cen-v076n013.p032 Freemantle, 1998, Ionic liquids show promise for clean separation technology, Chem. Eng. News., 76, 12, 10.1021/cen-v076n034.p012 Freemantle, 1999, Ionic liquids prove increasingly versatile, Chem. Eng. News., 77, 23, 10.1021/cen-v077n001.p023 Hussey, 1983, Ionic Liquids, Adv. Molten Salt Chem., 5, 185 Hussey, 1988, Room-temperature haloaluminate ionic liquids – novel solvents for transition metal solution chemistry, Pure Appl. Chem., 60, 1763, 10.1351/pac198860121763 Seddon, 1996, Room-temperature ionic liquids: neoteric solvents for clean catalysis, Kinet. Catal., 37, 693 Welton, 1999, Room-temperature ionic liquids, Solvents for synthesis and catalysis, Chem. Rev., 99, 2071, 10.1021/cr980032t Seddon, 1997, Ionic liquids for clean technology, J. Chem. Tech. Biotech., 68, 351, 10.1002/(SICI)1097-4660(199704)68:4<351::AID-JCTB613>3.0.CO;2-4 Seddon, 1998, Ionic liquids for clean technology: an update, 53 Alonso, 2008, Solvent extraction of thiophene from n-alkanes (C7, C12, and C16) using the ionic liquid [C8mim][BF4], J. Chem. Thermodyn., 40, 966, 10.1016/j.jct.2008.01.025 Alonso, 2008, Thiophene separation from aliphatic hydrocarbons using the 1-ethyl-3-methylimidazolium ethylsulfate ionic liquid, Fluid Phase Equilib., 270, 97, 10.1016/j.fluid.2008.06.012 Kumar, 2009, Thiophene separation with ionic liquids for desulphurization: a quantum chemical approach, Fluid Phase Equilib., 278, 1, 10.1016/j.fluid.2008.11.019 Kedra-Krolik, 2011, Extraction of thiophene or pyridine from n-heptane using ionic liquids, gasoline and diesel desulfurization, Ind. Eng. Chem. Res., 50, 2296, 10.1021/ie101834m Marciniak, 2012, Ternary (liquid+liquid) equilibria of trifluorotris (perfluoroethyl) phosphate based ionic liquids + thiophene + heptane, J. Chem. Thermodyn., 49, 154, 10.1016/j.jct.2012.01.026 Domanska, 2013, Separation of thiophene from heptane with ionic liquids, J. Chem. Thermodyn., 61, 126, 10.1016/j.jct.2013.01.033 Song, 2016, Effect of cation alkyl chain length on liquid-liquid equilibria of {ionic liquids + thiophene + heptane}: COSMO-RS prediction and experimental verification, Fluid Phase Equilib., 425, 244, 10.1016/j.fluid.2016.06.016 Baelhadj, 2017, Liquid−liquid equilibria for the ternary systems dodecane + toluene or thiophene or pyridine + 1ethyl-3-methylimidazolium methyl sulfate, J. Chem. Eng. Data, 62, 1749, 10.1021/acs.jced.6b00437 Heintz, 2001, J. Chem. Eng. Data, 46, 1526, 10.1021/je0101348 Meindersma, 2005, Fuel Process. Technol., 87, 59, 10.1016/j.fuproc.2005.06.002 Meindersma, 2008, Chem. Eng. Res. Des., 86, 745, 10.1016/j.cherd.2008.02.016 Meindersma, 2010, Ind. Eng. Chem. Res., 49, 7530, 10.1021/ie100703p Heintz, 2001, Thermodynamic properties of mixtures containing ionic liquids. 1. activity coefficients at infinite dilution of alkanes, alkenes, and alkylbenzenes in 4-methyl-n-butylpyridinium tetrafluoroborate using gas−liquid chromatography, J. Chem. Eng. Data, 46, 1526, 10.1021/je0101348 Meindersma, 2005, Selection of ionic liquids for the extraction of aromatic hydrocarbons from aromatic/aliphatic mixtures, Fuel Process. Technol., 87, 59, 10.1016/j.fuproc.2005.06.002 Meindersma, 2008, Conceptual process design for aromatic/aliphatic separation with ionic liquids, Chem. Eng. Res. Des., 86, 745, 10.1016/j.cherd.2008.02.016 Meindersma, 2010, Ionic liquids for aromatics extraction. Present status and future outlook, Ind. Eng. Chem. Res., 49, 7530, 10.1021/ie100703p Canales, 2016, Comparison of ionic liquids to conventional organic solvents for extraction of aromatics from aliphatics, J. Chem. Eng. Data, 61, 1685, 10.1021/acs.jced.6b00077 Brancker, 1941, Mixed solvent extraction, Ind. Eng. Chem., 33, 880, 10.1021/ie50379a014 Alkhaldi, 2011, Separation of propylbenzene and n-alkanes from their mixtures using 4-methyl-N-butylpyridinium tetrafluoroborate as an ionic solvent at several temperatures, Fluid Phase Equilib., 309, 102, 10.1016/j.fluid.2011.06.036 AlTuwaim, 2011, Extraction of propylbenzene or butylbenzene from dodecane using 4-methyl-N-butylpyridinium tetrafluoroborate, (mebupy)(BF4), as an ionic liquid at different temperatures, J. Chem. Thermodyn., 43, 1804, 10.1016/j.jct.2011.06.009 AlTuwaim, 2012, Extraction of propylbenzene from its mixtures with heptadecane using 4-methyl-N-butylpyridinium tetrafluoroborate, Fluid Phase Equilib., 315, 21, 10.1016/j.fluid.2011.11.008 Fandary, 2012, Evaluation of (bmim)(PF6) as an ionic solvent for the extraction of propylbenzene from aliphatic compounds, J. Chem. Thermodyn., 54, 322, 10.1016/j.jct.2012.05.010 Al-Rashed, 2012, Extraction of butylbenzene from dodecane using hexafluorophosphate-based ionic liquids: effect of cation change, J. Chem. Eng. Data, 57, 2907, 10.1021/je3002305 Al-Jimaz, 2013, Study on the separation of propylbenzene from alkanes using two methylsulfate-based ionic liquids at (313 and 333) K, Fluid Phase Equilib., 354, 29, 10.1016/j.fluid.2013.06.010 Alkhaldi, 2017, Evaluation of 1-ethyl-3-methylimidazolium methylsulfate and 1,3-dimethylimidazolium methylsulfate as solvents for extraction of alkylbenzenes from hexadecane at 313 and 333K, Fluid Phase Equilib., 454, 35, 10.1016/j.fluid.2017.09.011 Alkhaldi, 2018, Effect of solvent cation alkyl-chain length on the separation of butylbenzene from ntetradecane using hexafluorophosphate-based ionic liquids at (313.15 and 333.15) K and 101.3, J. Chem. Eng. Data, 63, 3751, 10.1021/acs.jced.8b00356 Alkhaldi, 2019, Liquid extraction of toluene from heptane, octane, or nonane using mixed ionic solvents of 1ethyl-3-methylimidazolium methylsulfate and 1hexyl-3-methylimidazolium hexafluorophosphate, J. Chem. Eng. Data, 64, 169, 10.1021/acs.jced.8b00669 Al-Tuwaim, 2019, Separation of alkylbenzenes from nheptane using binary mixtures of ionic solvents, J. Chem. Eng. Data, 64, 1187, 10.1021/acs.jced.8b01100 Aliaga, 2007, Sum frequency generation spectroscopy of dicyanamide based room-temperature ionic liquids. Orientation of the cation and the anion at 168 Applications of Ionic Liquids in Science and Technology the gas-liquid interface, J. Phys. Chem. B, 111, 9733, 10.1021/jp072899d MacFarlane, 2001, Low viscosity ionic liquids based on organic salts of the dicyanamide anion, Chem. Commun., 16, 1430, 10.1039/b103064g Paucar, 2021, Ionic liquids for the removal of sulfur and nitrogen compounds in fuels: a review, Environ. Chem. Lett., 19, 1205, 10.1007/s10311-020-01135-1 Hansmeier, 2011, Desulfurization and denitrogenation of gasoline and diesel fuels by means of ionic liquids, Green Chem., 13, 1907, 10.1039/c1gc15196g Butt, 2020, Fuel oil desulfurization with dual functionalized imidazolium based ionic liquids, Sep. Purif. Technol., 248, 10.1016/j.seppur.2020.116959 Wilfred, 2012, Effect of temperature on extractions, Fuel Process. Technol., 93, 85, 10.1016/j.fuproc.2011.09.018 Wang, 2007, Desulfurization of gasoline by extraction with N-alkyl-pydinium-based ionic liquids, Ranliao Huaxue Xuebao, 35, 293 Wang, 2005, Extractive removal of thiophene sulfide from diesel using ionic liquids, 273 Cheruku, 2012, Liquid–liquid equilibrium data for 1-ethyl-3-methylimidazolium acetate–thiophene–diesel compound: experiments and correlations, J. Solution Chem., 41, 898, 10.1007/s10953-012-9840-5 Rogosic, 2016, Liquid-liquid equilibria in the ternary and multicomponent systems involving hydrocarbons, thiophene or pyridine and ionic liquid (1-benzyl-3-metylimidazolium bis(trifluorometylsulfonyl)imide), Fluid Phase Equilib., 412, 39, 10.1016/j.fluid.2015.12.025 Cheng, 2018, Effects of interaction with Sulphur compounds and free volume in imidazolium-based ionic liquid on desulphurization: a molecular dynamics study, Mol. Simul., 44, 55, 10.1080/08927022.2017.1337273 Hansmeier, 2011, Desulfurization and denitrogenation of gasoline and diesel fuels by means of ionic liquids, Green Chem., 13, 1907, 10.1039/c1gc15196g Abrams, 1975, Statistical thermodynamics of liquid mixtures: a new expression for the excess Gibbs energy of partly or completely miscible systems, AIChE J., 21, 116, 10.1002/aic.690210115 Renon, 1968, Local compositions in thermodynamic excess functions for liquid mixtures, AIChE J., 14, 135, 10.1002/aic.690140124 Sorensen, 1980, Liquid-liquid equilibrium data collection, Dechema Chem. Data Series, Dechema. Vol. V Part, 2