Abstract View

Author(s): Mahbub Alam1, Md. Shahriar Hasan2, Md. Abu Bin Hasan Susan3, Muhammed Shah Miran*4

Email(s): 1shahmiran@du.ac.bd


    Department of Chemistry, University of Dhaka, Dhaka-1000, Bangladesh

Published In:   Volume - 3,      Issue - 2,     Year - 2023

DOI: 10.55878/SES2023-3-2-1  

 View HTML        View PDF

Please allow Pop-Up for this website to view PDF file.

In this study, a protic ionic liquid (PIL), diethylmethylammonium trifluoroacetate was synthesized through neutralization of a tertiary amine, diethylmethylamine (dema) with trifluoroacetic acid (CF3COOH).Binary mixtures of [demaH] CF3COO- with a wide range of compositions with ethanol, 1-propanol, 1-butanol, and 1-pentanol were prepared and the density, viscosity, and ionic conductivity of the PIL and binary mixtures were measuredat 30°C. Excess properties were investigated byfitting density and viscosity data to the Redlich-Kister equation. An increase in the mole fraction of [demaH] CF3COO-was found to increase the density and viscosity, while a decrease was apparent with increase in the alkyl chain length of alcohols. For all compositions, binary mixtures of alcohols with shorter alkyl chains showed better conductivity when the chain length was less than five carbons. [demaH]CF3COO-and its binary mixtures were found to be poor PILs with low ionicityowing tothe low pKa(10.0) value of the constituent acid and amine of the PIL.

Cite this article:
Mahbub Alam, Md. Shahriar Hasan, Md. Abu Bin Hasan Susan, Muhammed Shah Miran* (2023), Effect of alkyl chain length of alcohols on the physicochemical properties of their binary mixtures with diethylmethylammonium trifluoroacetate, Spectrum of Emerging Sciences, 3(2), pp. 1-8. 10.55878/SES2023-3-2-1DOI: https://doi.org/10.55878/SES2023-3-2-1


[1]Wasserscheid P, Welton T, editors. Ionic liquids in synthesis. Wiley; 2007. https://doi.org/10.1002/9783527621194.

[2]Miran MS, Hoque M, Yasuda T, Tsuzuki S, Ueno K, Watanabe M. Key factor governing the physicochemical properties and extent of proton transfer in protic ionic liquids: ΔpKa or chemical structure? Phys Chem Chem Phys 2019;21:418–26. https://doi.org/10.1039/c8cp06973e.

[3]Yoshizawa M, Xu W, Angell CA. Ionic liquids by proton transfer: vapor pressure, conductivity, and the relevance of ΔpKa from aqueous solutions. J Am Chem Soc 2003;125:15411–9. https://doi.org/10.1021/ja035783d.

[4]Silva W, Zanatta M, Ferreira AS, Corvo MC, Cabrita EJ. Revisiting ionic liquid structure‐property relationship: A critical analysis. Int J Mol Sci 2020;21:1–37. https://doi.org/10.3390/ijms21207745.

[5]Bhanuprakash P, Jyothi NVV, Narasimharao C, Raveendra M, Sivakumar K. Temperature and composition dependence of the volumetric and acoustic properties of ionic liquid [emim][HSO4] with polar protic and aprotic co-solvents. J Chem Thermodyn 2018;122:113–24. https://doi.org/10.1016/j.jct.2018.03.007.

[6]Berga L, Bruce I, Nicol TWJ, Holding AJ, Isobe N, Shimizu S, Walker AJ, Reid JESJ. Cellulose dissolution and regeneration using a non-aqueous, non-stoichiometric protic ionic liquid system. Cellulose 2020;27:9593–603. https://doi.org/10.1007/s10570-020-03444-8.

[7]Stettner T, Balducci A. Protic ionic liquids in energy storage devices: past, present and future perspective. Energy Storage Mater 2021;40:402–14. https://doi.org/10.1016/j.ensm.2021.04.036.

[8]Arumugam V, Rajamanikandan R, Ilanchelian M, Moodley KG, Redhi GG. Investigation of binding interactions between BSA and [EPMpyr][Sal] through spectroscopy studies, thermophysical and thermodynamic properties. Spectrochim Acta - Part A Mol Biomol Spectrosc 2019;210:299–307. https://doi.org/10.1016/j.saa.2018.11.024.

[9]Greaves TL, Drummond CJ. Protic ionic liquids: properties and applications. Chem Rev 2008;39:206–37. https://doi.org/10.1002/chin.200818249.

[10]Miran MS, Kinoshita H, Yasuda T, Susan MABH, Watanabe M. Physicochemical properties determined by ΔpKa for protic ionic liquids based on an organic super-strong base with various Brønsted acids. Phys Chem Chem Phys 2012;14:5178–86. https://doi.org/10.1039/c2cp00007e.

[11]Boli E, Katsavrias T, Voutsas E. Viscosities of pure protic ionic liquids and their binary and ternary mixtures with water and ethanol. Fluid Phase Equilib 2020;520:112663. https://doi.org/10.1016/j.fluid.2020.112663.

[12]Rauber D, Philippi F, Becker J, Zapp J, Morgenstern B, Kuttich B, Kraus T, Hempelmann R, Hunt P, Welton T, Kay CWM. Anion and ether group influence in protic guanidinium ionic liquids. Phys Chem Chem Phys 2023;25:6436–53. https://doi.org/10.1039/d2cp05724g.

[13]Musale SP, Babalsure PS, Pawar DD. Volumetric properties, viscosity coefficients and aggregation behaviour of DBU-acetate protic ionic liquid in molecular solvents. J Mol Liq 2020;319:114197. https://doi.org/10.1016/j.molliq.2020.114197.

[14]Reddy TDN, Mallik BS. Hydrogen Bond Kinetics, Ionic dynamics, and voids in the binary mixtures of protic ionic liquids with alkanolamines. J Phys Chem B 2021;125:5587–600. https://doi.org/10.1021/acs.jpcb.0c10658.

[15]Reid JESJ, Shimizu S, Walker AJ. Connecting precursors to a protic ionic liquid: effects of hydrogen bond synergy in acid-base binary mixtures on the solvent-solute interactions. J Mol Liq 2020;297:111746. https://doi.org/10.1016/j.molliq.2019.111746.

[16]Saikat MSH, Islam MM, Mollah MYA, Susan MABH, Miran MS. Thermal and electrochemical properties of protic ionic liquids and their binary mixtures with water. Mater Today Proc 2019;15:498–503. https://doi.org/10.1016/j.matpr.2019.04.113.

[17]Ortiz-Martínez VM, Ortiz A, Fernández-Stefanuto V, Tojo E, Colpaert M, Améduri B, Ortiz I. Fuel cell electrolyte membranes based on copolymers of protic ionic liquid [HSO3-BVIm][TfO] with MMA and hPFSVE. Polymer 2019;179:121583. https://doi.org/10.1016/j.polymer.2019.121583.

[18]Keshapolla D, Ijardar SP, Gardas RL. Temperature dependent apparent molar properties of trihexylammonium carboxylate based protic ionic liquids in toluene and dodecane. J Mol Liq 2018;272:1058–69. https://doi.org/10.1016/j.molliq.2018.10.114.

[19]Ingenmey J, Von Domaros M, Perlt E, Verevkin SP, Kirchner B. Thermodynamics and proton activities of protic ionic liquids with quantum cluster equilibrium theory. J Chem Phys 2018;148. https://doi.org/10.1063/1.5010791.

[20]Mazan V, Boltoeva M. Aqueous N-H acid bis(trifluoromethylsulfonyl) imide solution - [C4mim][Tf2N] ionic liquid biphasic system: an original investigation by diffusion ordered spectroscopy nuclear magnetic resonance. J Fluor Chem 2021;245. https://doi.org/10.1016/j.jfluchem.2021.109782.

[21]Otero-Mato JM, Rivera-Pousa A, Montes-Campos H, Cabeza O, Heuer A, Diddens D, Varela LM. Computational study of the structure of ternary ionic liquid/salt/polymer electrolytes based on protic ionic liquids. J Mol Liq 2021;333. https://doi.org/10.1016/j.molliq.2021.115883.

[22]Kobzar YL, Azzouz G, Albadri H, Levillain J, Dez I, Gaumont AC, Lecamp L, Chappey C, Marais S, Fatyeyeva K. Novel ionic conducting composite membrane based on polymerizable ionic liquids. Polymers 2021;13. https://doi.org/10.3390/polym13213704.

[23]Wojnarowska Z, Lange A, Taubert A, Paluch M. Ion and proton transport in aqueous/nonaqueous acidic ionic liquids for fuel-cell applications - insight from high-pressure dielectric studies. ACS Appl Mater Interfaces 2021;13:30614–24. https://doi.org/10.1021/acsami.1c06260.

[24]Marium M, Rahman MM, Mollah MYA, Susan MABH. Molecular level interactions in binary mixtures of 1-ethyl 3-methylimidazolium tetrafluoroborate and water. RSC Adv 2015;5:19907–13. https://doi.org/10.1039/c5ra00083a.

[25]Miran MS, Yasuda T, Susan MABH, Dokko K, Watanabe M. Binary protic ionic liquid mixtures as a proton conductor: High fuel cell reaction activity and facile proton transport. J Phys Chem C 2014;118:27631–9. https://doi.org/10.1021/jp506957y.

[26]Anouti M, Jacquemin J, Porion P. Transport properties investigation of aqueous protic ionic liquid solutions through conductivity, viscosity, and NMR self-diffusion measurements. J Phys Chem B 2012;116:4228–38. https://doi.org/10.1021/jp3010844.

[27]Majstorović DM, Mirković MR, Kijevčanin ML, Živković EM. Analysis of thermophysical properties of binary systems containing ethyl acetate and 1-propanol or 1-butanol. Hem Ind 2020;74:163–85. https://doi.org/10.2298/HEMIND191203017M.

[28]Rilo E, Ferreira AGM, Fonseca IMA, Cabeza O. Densities and derived thermodynamic properties of ternary mixtures 1-butyl-3-methyl-imidazolium tetrafluoroborate+ethanol+water at seven pressures and two temperatures. Fluid Phase Equilib 2010;296:53–9. https://doi.org/10.1016/j.fluid.2010.03.039.

[29]Iglesias M, Torres A, Gonzalez-Olmos R, Salvatierra D. Effect of temperature on mixing thermodynamics of a new ionic liquid: {2-Hydroxy ethylammonium formate (2-HEAF) + short hydroxylic solvents}. J Chem Thermodyn 2008;40:119–33. https://doi.org/10.1016/j.jct.2007.05.011.

[30]Zhao Y, Zhang X, Zeng S, Zhou Q, Dong H, Tian X, Zhang S. Density, viscosity, and performances of carbon dioxide capture in 16 absorbents of amine + ionic liquid + H2O, ionic liquid + H2O, and amine + H2O systems. J Chem Eng Data 2010;55:3513–9. https://doi.org/10.1021/je100078w.

[31]Raabe G, Köhler J. Thermodynamical and structural properties of binary mixtures of imidazolium chloride ionic liquids and alcohols from molecular simulation. J Chem Phys 2008;129. https://doi.org/10.1063/1.2990653.

[32]Ueno K, Tokuda H, Watanabe M. Ionicity in ionic liquids: correlation with ionic structure and physicochemical properties. Phys Chem Chem Phys 2010;12:1648–1648. https://doi.org/10.1039/c001176m.

[33]Sengupta A, Kumar S, Kamaz M, Jebur M, Wickramasinghe R. Synthesis and characterization of antibacterial poly ionic liquid membranes with tunable performance. Sep Purif Technol 2019;212:307–15. https://doi.org/10.1016/j.seppur.2018.11.027.

[34]Anderson JL, Clark KD. Ionic liquids as tunable materials in (bio) analytical chemistry. Anal Bioanal Chem 2018;410:4565–6. https://doi.org/10.1007/s00216-018-1125-4.

[35]Blahut A, Dohnal V, Vrbka P. Interactions of volatile organic compounds with the ionic liquid 1-ethyl-3-methylimidazolium tetracyanoborate. J Chem Thermodyn 2012;47:100–8. https://doi.org/10.1016/j.jct.2011.09.028.

[36]Anouti M, Jacquemin J, Lemordant D. Transport properties of protic ionic liquids, pure and in aqueous solutions: effects of the anion and cation structure. Fluid Phase Equilib 2010;297:13–22. https://doi.org/10.1016/j.fluid.2010.05.019.

[37]Martínez-Crespo P, Otero-Lema M, Cabeza O, Montes-Campos H, Varela LM. Structure, dynamics and ionic conductivities of ternary ionic liquid/lithium salt/DMSO mixtures. J Mol Liq 2022;359:0–8. https://doi.org/10.1016/j.molliq.2022.119188.

[38]Costa F, Paixão FS, Zimmermann AS, da Silva ACM, Mattedi S. Physical and chemical properties of binary mixtures of dibutylammonium-based ionic liquids and water. Brazilian J Chem Eng 2022;39:843–56. https://doi.org/10.1007/s43153-021-00174-7.

[39]Soman DP, Kalaichelvi P, Radhakrishnan TK. Thermal conductivity enhancement of aqueous ionic liquid and nanoparticle suspension. Brazilian J Chem Eng 2019;36:855–68. https://doi.org/10.1590/0104-6632.20190362s20180436.

[40]Cao Q, Lu X, Wu X, Guo Y, Xu L, Fang W. Density, viscosity, and conductivity of binary mixtures of the ionic liquid N -(2-hydroxyethyl)piperazinium propionate with water, methanol, or ethanol. J Chem Eng Data 2015;60:455–63. https://doi.org/10.1021/je500380x.

[41]Al-Zohbi F, Jacquemin J, Ghamouss F, Schmaltz B, Abarbri M, Cherry K, Tabcheh MF, Tran-Van F. Impact of the aqueous pyrrolidinium hydrogen sulfate electrolyte formulation on transport properties and electrochemical performances for polyaniline-based supercapacitor. J Power Sources 2019;431:162–9. https://doi.org/10.1016/j.jpowsour.2019.05.018.

[42]Kobrak MN, Yager KG. X-Ray scattering and physicochemical studies of trialkylamine/carboxylic acid mixtures: nanoscale structure in pseudoprotic ionic liquids and related solutions. Phys Chem Chem Phys 2018;20:18639–46. https://doi.org/10.1039/c8cp02854k.

[43]Yaghini N, Abdurrokhman I, Hasani M, Martinelli A. Transport properties and intermolecular interactions in binary mixtures based on the protic ionic liquid ethylimidazolium triflate and ethylene glycol. Phys Chem Chem Phys 2018;20:22980–6. https://doi.org/10.1039/c8cp03093f.

[44]Jacquemin J, Anouti M, Lemordant D. Physico-chemical properties of non-newtonian shear thickening diisopropyl-ethylammonium-based protic ionic liquids and their mixtures with water and acetonitrile. J Chem Eng Data 2011:556–64. https://doi.org/10.1021/je101191e.

[45]Soldatović D, Vuksanović J, Radović I, Višak Z, Kijevčanin M. Excess molar volumes and viscosity behaviour of binary mixtures of aniline/or N,N-dimethylaniline with imidazolium ionic liquids having triflate or bistriflamide anion. J Chem Thermodyn 2017;109:137–54. https://doi.org/10.1016/j.jct.2017.02.007.

[46]Fernandes RL, Hoga HE, Torres RB. Molecular interactions of ionic liquid {n-butylammonium methanoate (N4Met) + alcohols} at several temperatures: thermodynamic and spectroscopic properties. J Chem Thermodyn 2020;148:106140. https://doi.org/10.1016/j.jct.2020.106140.

[47]Nascimento AD, Reis RD, Santos JPS, Mattedi S, Senna LF. Thermophysical properties of diethylammonium (acetate + water) mixtures at different temperatures. J Chem Thermodyn 2020;145:106093. https://doi.org/10.1016/j.jct.2020.106093.

[48]Ali MA, Susan MABH. Volumetric and spectroscopic studies of 1-ethyl-3-methylimidazolium ethylsulfate/propane-1-ol binary mixtures at different temperatures. Spectr Emerg Sci 2023;2:17–28. https://doi.org/10.55878/ses2022-2-2-5.

[49]Gonzalez EJ, Alonso L, Dominguez A. Physical properties of binary mixtures of the ionic liquid 1-methyl-3-octylimidazolium chloride with methanol, ethanol, and 1-propanol at T ) (298.15, 313.15, and 328.15) K and at P ) 0.1 MPa. J Chem Eng Data 2006;51:1446–52. https://doi.org/10.1021/je060123k.

[50]Baker EN, Hubbard RE. Hydrogen bonding in globular proteins. Prog Biophys Mol Biol 1984;44:97–179. https://doi.org/10.1016/0079-6107(84)90007-5.

[51]Angell CA, Ansari Y, Zhao Z. Ionic liquids: past, present and future. Faraday Discuss 2012;154:9–27. https://doi.org/10.1039/c1fd00112d.

[52]Schreiner C, Zugmann S, Hartl R, Gores HJ. Fractional walden rule for ionic liquids: Examples from recent measurements and a critique of the so-called ideal KCl line for the walden plot. J Chem Eng Data 2010;55:1784–8. https://doi.org/10.1021/je900878j.

[53]Augusto FF, Francisco M, Stephen E, Jason H, Luuk VDW, Geert-Jan W, Bruno FM. Physicochemical characterization of two protic hydroxyethylammonium carboxylate ionic liquids in water and their mixture. J Chem Eng Data 2022;67:1309–25. https://doi.org/10.1021/acs.jced.1c00687.

[54]Anouti M, Caillon-Caravanier M, Dridi Y, Galiano H, Lemordant D. Synthesis and characterization of new pyrrolidinium based protic ionic liquids. Good and superionic liquids. J Phys Chem B 2008;112:13335–43. https://doi.org/10.1021/jp805992b.

[55]Chakraborty M, Barik S, Mahapatra A, Sarkar M. Binary mixtures of ionic liquids: Ideal, non-ideal, or quasi-ideal? J Chem Phys 2021;154. https://doi.org/10.1063/5.0051417.





Related Images:

Recent Images

Comparing the antibacterial activity of plants against bacteria
Industrial algae mediated development and evaluation of Titanium Oxide nanoparticles, their ability to fight bacteria, and environmental application
Bacterial mediated synthesis and characterization of copper oxide nanoparticles and their antimicrobial and dye remediation applications
Fungal mediated synthesis and characterization of mixed iron- manganese oxide nanoparticles and their antimicrobial and dye remediation applications
Effect of alkyl chain length of alcohols on the physicochemical properties of their binary mixtures with diethylmethylammonium trifluoroacetate,
Catalysing sustainability by harnessing microbial activities and technologies to improve sustainability for wide-scale implementation and prevent disease,
Cutting-edge breakthroughs in the acetone-butanol-ethanol fermentation technology
Probabilistic Machine Learning and Artificial Intelligence
A Study on Genetic Inheritance of Mutations in Drosophila Melanogaster
Synthesis of potassium salts from derivatives of natural acids


Recomonded Articles:

Author(s): Samrat Paudel; Rekina Shrestha; Pramod Poudel; Rameshwar Adhikari

DOI: 10.55878/SES2022-2-1-1         Access: Open Access Read More

Author(s): Parag Jain; Puneet Pal Singh

DOI: 10.55878/SES2021-1-1-1         Access: Open Access Read More

Author(s): Binod Shrestha, Sambridhi Shah, Khagendra Chapain, Rajendra Joshi, Rajesh Pandit

DOI: 10.55878/SES2022-2-1-7         Access: Open Access Read More

Author(s): Sushant Bindra; Mehak Piplani

DOI:         Access: Open Access Read More

Author(s): Reena Rawat

DOI:         Access: Open Access Read More

Author(s): Anand Pathak; Saurabh Deshmukh

DOI:         Access: Open Access Read More

Author(s): Bhupendra Kande, Prachi Parmar

DOI: 10.55878/SES2022-2-1-3         Access: Open Access Read More

Author(s): B. D. Patel

DOI:         Access: Open Access Read More

Author(s): Ruchi Sharma

DOI: 10.55878/SES2022-2-1-5         Access: Open Access Read More

Author(s): Jaya V Gade

DOI:         Access: Open Access Read More

Author(s): Vania Munjar

DOI: 10.55878/SES2021-1-1-12         Access: Open Access Read More

Author(s): Shubhangi Jha, Pragya Kulkarni and Anamika Sharma

DOI: 10.55878/SES2022-2-2-3         Access: Open Access Read More

Author(s): Roli Jain

DOI: 10.55878/SES2022-2-1-6         Access: Open Access Read More

Author(s): Shathya Pranav Sujithra Rajesh Kannan

DOI: 10.55878/SES2022-2-2-1         Access: Open Access Read More

Author(s): Sonam Tamang, Anu Surendran, Kamal P. Sharma, Jyoti Giri, Sabu Thomas, Takahiro Maruyama, Sabita Shrestha, Rameshwar Adhikari

DOI: 10.55878/SES2023-3-1-2         Access: Open Access Read More