ACS Publications. Most Trusted. Most Cited. Most Read
Thermodynamic Properties of Mixtures Containing Ionic Liquids. 7. Activity Coefficients of Aliphatic and Aromatic Esters and Benzylamine in 1-Methyl-3-ethylimidazolium Bis(trifluoromethylsulfonyl) Imide Using the Transpiration Method

OR SEARCH CITATIONS

My Activity
Publications

Figure 1Loading Img
Download Hi-Res ImageDownload to MS-PowerPointCite This:J. Chem. Eng. Data 2006, 51, 1, 213-218
    Article

    Thermodynamic Properties of Mixtures Containing Ionic Liquids. 7. Activity Coefficients of Aliphatic and Aromatic Esters and Benzylamine in 1-Methyl-3-ethylimidazolium Bis(trifluoromethylsulfonyl) Imide Using the Transpiration Method
    Click to copy article linkArticle link copied!

    View Author Information
    Department of Physical Chemistry, University of Rostock, Hermannstrasse 14, D-18055 Rostock, Germany
    Faculty of Chemistry, Physical Chemistry Division, Warsaw University of Technology, Warsaw, Poland
    Other Access Options

    Journal of Chemical & Engineering Data

    Cite this: J. Chem. Eng. Data 2006, 51, 1, 213–218
    Click to copy citationCitation copied!
    https://doi.org/10.1021/je050334+
    Published November 4, 2005
    Copyright © 2006 American Chemical Society
    Request reuse permissions

    Abstract

    Click to copy section linkSection link copied!

    Vapor−liquid equilibria of binary mixtures containing the high boiling solutes (dimethyl adipate, ethyl benzoate, and benzylamine) with the ionic liquid 1-methyl-3-ethylimidazolium bis(trifluoromethylsulfonyl) imide [EMIM][NTf2] were studied using the transpiration method. VLE measurements were carried out over the whole concentration range at temperatures between 298 K and 318 K. Activity coefficients (γi) of these solvents in the ionic liquid were determined from these data and are correlated by the NRTL equation. In addition, vapor pressures of the pure solutes dimethyl adipate and ethyl benzoate have been measured as a function of temperature, and their enthalpies of vaporization have been derived.

    Copyright © 2006 American Chemical Society

    Subjects

    what are subjects

    Read this article

    To access this article, please review the available access options below.

    Get instant access

    Purchase Access

    Read this article for 48 hours. Check out below using your ACS ID or as a guest.

    Recommended

    Access through Your Institution

    You may have access to this article through your institution.

    Your institution does not have access to this content. Add or change your institution or let them know you’d like them to include access.

    *

     Corresponding author. E-mail:  andreas.heintz@ uni-rostock.de.

    Cited By

    Click to copy section linkSection link copied!

    This article is cited by 42 publications.

    1. Sergey P. Verevkin, Arina V. Elbakari, Sergey V. Vostrikov, Ruslan N. Nagrimanov, Mikhail A. Varfolomeev. Renewable Platform Chemicals: Evaluation of Experimental Data for Alkyl Benzoates with Complementary Measurements, Structure–Property Correlations, and Quantum Chemical Calculations. Journal of Chemical & Engineering Data 2024, 69 (2) , 380-399. https://doi.org/10.1021/acs.jced.3c00310
    2. Sayeed Ashique Ahmed, Aninda Chatterjee, Banibrata Maity, and Debabrata Seth . Thermodynamic Behavior of Binary Mixtures of 1-Butyl-1-methylpyrrolidinium Iodide and Alcohols. Journal of Chemical & Engineering Data 2015, 60 (8) , 2301-2307. https://doi.org/10.1021/acs.jced.5b00184
    3. Chang-Hao Li, Kai-Xuan Gao, Yu-Ning Meng, Xian-Kun Wu, Feng Zhang, and Zhi-Xiang Wang . Solution Thermodynamics of Imidazolium-Based Ionic Liquids and Volatile Organic Compounds: Benzene and Acetone. Journal of Chemical & Engineering Data 2015, 60 (6) , 1600-1607. https://doi.org/10.1021/je500986b
    4. Wenxiu Li, Dezhang Sun, Tao Zhang, Yanhong Huang, Lin Zhang, and Zhigang Zhang . Phase Equilibrium Study of Binary and Ternary Mixtures of Ionic Liquids + Acetone + Methanol. Journal of Chemical & Engineering Data 2014, 59 (12) , 3975-3981. https://doi.org/10.1021/je500418f
    5. Zhigang Lei, Chengna Dai, Xing Liu, Li Xiao, and Biaohua Chen . Extension of the UNIFAC Model for Ionic Liquids. Industrial & Engineering Chemistry Research 2012, 51 (37) , 12135-12144. https://doi.org/10.1021/ie301159v
    6. Jason P. Hallett and Tom Welton . Room-Temperature Ionic Liquids: Solvents for Synthesis and Catalysis. 2. Chemical Reviews 2011, 111 (5) , 3508-3576. https://doi.org/10.1021/cr1003248
    7. Hemayat Shekaari and Sedighehnaz S. Mousavi. Osmotic Coefficients and Refractive Indices of Aqueous Solutions of Ionic Liquids Containing 1-Butyl-3-methylimidazolium Halide at T = (298.15 to 328.15) K. Journal of Chemical & Engineering Data 2009, 54 (3) , 823-829. https://doi.org/10.1021/je800609u
    8. Zhigang Lei, Jiguo Zhang, Qunsheng Li and Biaohua Chen. UNIFAC Model for Ionic Liquids. Industrial & Engineering Chemistry Research 2009, 48 (5) , 2697-2704. https://doi.org/10.1021/ie801496e
    9. Yusuke Shimoyama, Takeshi Hirayama and Yoshio Iwai. Measurement of Infinite Dilution Activity Coefficients of Alcohols, Ketones, and Aromatic Hydrocarbons in 4-Methyl-N-butylpyridinium Tetrafluoroborate and 1-Butyl-3-methylimidazolium Hexafluorophosphate by Gas−Liquid Chromatography. Journal of Chemical & Engineering Data 2008, 53 (9) , 2106-2111. https://doi.org/10.1021/je800246v
    10. Alan R. Katritzky, Minati Kuanar, Iva B. Stoyanova-Slavova, Svetoslav H. Slavov, Dimitar A. Dobchev, Mati Karelson and William E. Acree, Jr. . Quantitative Structure–Property Relationship Studies on Ostwald Solubility and Partition Coefficients of Organic Solutes in Ionic Liquids. Journal of Chemical & Engineering Data 2008, 53 (5) , 1085-1092. https://doi.org/10.1021/je700607b
    11. Tengfang Wang,, Changjun Peng,, Honglai Liu, and, Ying Hu, , Jianwen Jiang. Equation of State for the Vapor−Liquid Equilibria of Binary Systems Containing Imidazolium-Based Ionic Liquids. Industrial & Engineering Chemistry Research 2007, 46 (12) , 4323-4329. https://doi.org/10.1021/ie061577d
    12. Laura Sprunger,, Michael Clark,, William E. AcreeJr., and, Michael H. Abraham. Characterization of Room-Temperature Ionic Liquids by the Abraham Model with Cation-Specific and Anion-Specific Equation Coefficients. Journal of Chemical Information and Modeling 2007, 47 (3) , 1123-1129. https://doi.org/10.1021/ci7000428
    13. A. Vicent Orchillés,, Pablo J. Miguel,, Ernesto Vercher, and, Antoni Martínez-Andreu. Isobaric Vapor−Liquid Equilibria for Methyl Acetate + Methanol + 1-Ethyl-3-methylimidazolium Trifluoromethanesulfonate at 100 kPa. Journal of Chemical & Engineering Data 2007, 52 (3) , 915-920. https://doi.org/10.1021/je600518s
    14. Vladimir N. Emel'yanenko,, Sergey P. Verevkin, and, Andreas Heintz. The Gaseous Enthalpy of Formation of the Ionic Liquid 1-Butyl-3-methylimidazolium Dicyanamide from Combustion Calorimetry, Vapor Pressure Measurements, and Ab Initio Calculations. Journal of the American Chemical Society 2007, 129 (13) , 3930-3937. https://doi.org/10.1021/ja0679174
    15. A. Vicent Orchillés,, Pablo J. Miguel,, Ernesto Vercher, and, Antoni Martínez-Andreu. Ionic Liquids as Entrainers in Extractive Distillation:  Isobaric Vapor−Liquid Equilibria for Acetone + Methanol + 1-Ethyl-3-methylimidazolium Trifluoromethanesulfonate. Journal of Chemical & Engineering Data 2007, 52 (1) , 141-147. https://doi.org/10.1021/je0603170
    16. Sergey P. Verevkin,, Svetlana A. Kozlova, and, Vladimir N. Emel'yanenko, , Eugene D. Nikitin and, Alexander P. Popov, , Eugen L. Krasnykh. Vapor Pressures, Enthalpies of Vaporization, and Critical Parameters of a Series of Linear Aliphatic Dimethyl Esters of Dicarboxylic Acids. Journal of Chemical & Engineering Data 2006, 51 (5) , 1896-1905. https://doi.org/10.1021/je0602418
    17. Andreas Heintz and, Sergey P. Verevkin, , Daniel Ondo. Thermodynamic Properties of Mixtures Containing Ionic Liquids. 8. Activity Coefficients at Infinite Dilution of Hydrocarbons, Alcohols, Esters, and Aldehydes in 1-Hexyl-3-methylimidazolium Bis(trifluoromethylsulfonyl) Imide Using Gas−Liquid Chromatography. Journal of Chemical & Engineering Data 2006, 51 (2) , 434-437. https://doi.org/10.1021/je0503554
    18. Andreas Heintz,, Tatiana V. Vasiltsova,, Javid Safarov,, Eckard Bich, and, Sergey P. Verevkin. Thermodynamic Properties of Mixtures Containing Ionic Liquids. 9. Activity Coefficients at Infinite Dilution of Hydrocarbons, Alcohols, Esters, and Aldehydes in Trimethyl-butylammonium Bis(trifluoromethylsulfonyl) Imide Using Gas−Liquid Chromatography and Static Method. Journal of Chemical & Engineering Data 2006, 51 (2) , 648-655. https://doi.org/10.1021/je050440b
    19. Airat A. Notfullin, Dmitrii N. Bolmatenkov, Mikhail I. Yagofarov, Ilya S. Balakhontsev, Marat A. Ziganshin, Boris N. Solomonov. Vaporization thermodynamics of normal alkyl benzoates. Journal of Thermal Analysis and Calorimetry 2022, 147 (24) , 14631-14647. https://doi.org/10.1007/s10973-022-11643-7
    20. Boris N. Solomonov, Mikhail I. Yagofarov, Ruslan N. Nagrimanov. Additivity of vaporization enthalpy: Group and molecular contributions exemplified by alkylaromatic compounds and their derivatives. Journal of Molecular Liquids 2021, 342 , 117472. https://doi.org/10.1016/j.molliq.2021.117472
    21. Rudolf Naef, William E. Acree. Calculation of the Vapour Pressure of Organic Molecules by Means of a Group-Additivity Method and Their Resultant Gibbs Free Energy and Entropy of Vaporization at 298.15 K. Molecules 2021, 26 (4) , 1045. https://doi.org/10.3390/molecules26041045
    22. Chunli Zhi, Yang Tang, Jinru Wan, Xingming Liu, Honglin Chen, Xunqiu Wang. Determination and correlation of ternary isobaric vapour-liquid equilibrium data of (dimethyl succinate + dimethyl glutarate + dimethyl adipate) at 2, 5 and 8 kPa. The Journal of Chemical Thermodynamics 2020, 143 , 106047. https://doi.org/10.1016/j.jct.2019.106047
    23. Honglin Chen, Lei Zhang, Yulan Huang, Jingjing Lu, Zhijian Zhao, Xunqiu Wang. Isobaric vapor–liquid equilibrium of three binary systems containing dimethyl succinate, dimethyl glutarate and dimethyl adipate at 2, 5.2 and 8.3 kPa. The Journal of Chemical Thermodynamics 2019, 133 , 100-110. https://doi.org/10.1016/j.jct.2019.02.006
    24. Anne-Marie Bonsa, Jochen K. Lehmann, Andreas Heintz. Partial molar enthalpies of organic solutes in the ionic liquid [EMIM][EtSO4]. Journal of Molecular Liquids 2017, 226 , 96-99. https://doi.org/10.1016/j.molliq.2016.09.020
    25. Sayeed Ashique Ahmed, Aninda Chatterjee, Banibrata Maity, Debabrata Seth. Osmotic properties of binary mixtures 1-butyl-1-methylpyrrolidinium dicyanamide and 1-methyl-3-octylimidazolium chloride with water: Effect of aggregation of ions. The Journal of Chemical Thermodynamics 2015, 81 , 227-236. https://doi.org/10.1016/j.jct.2014.10.008
    26. A. Vahid, E. J. Maginn. Monte Carlo simulation and SAFT modeling study of the solvation thermodynamics of dimethylformamide, dimethylsulfoxide, ethanol and 1-propanol in the ionic liquid trimethylbutylammonium bis(trifluoromethylsulfonyl)imide. Physical Chemistry Chemical Physics 2015, 17 (11) , 7449-7462. https://doi.org/10.1039/C4CP05961A
    27. Sayeed Ashique Ahmed, Aninda Chatterjee, Banibrata Maity, Debabrata Seth. Osmotic properties of binary mixtures of 1-butyl-1-methylpyrrolidinium iodide and water. Journal of Molecular Liquids 2014, 200 , 349-353. https://doi.org/10.1016/j.molliq.2014.10.022
    28. Debasmita Dash, Shekhar Kumar, C. Mallika, U. Kamachi Mudali. Thermophysical, Volumetric, and Excess Properties of Aqueous Solutions of 1-Hexyl-3-methyl Imidazolium Bromide at 298.15 K and 0.1 MPa. ISRN Physical Chemistry 2013, 2013 , 1-7. https://doi.org/10.1155/2013/475296
    29. Brock C. Roughton, Brianna Christian, John White, Kyle V. Camarda, Rafiqul Gani. Simultaneous design of ionic liquid entrainers and energy efficient azeotropic separation processes. Computers & Chemical Engineering 2012, 42 , 248-262. https://doi.org/10.1016/j.compchemeng.2012.02.021
    30. Zhigang Lei, Li Xiao, Chengna Dai, Biaohua Chen. Group contribution lattice fluid equation of state (GCLF EOS) for ionic liquids. Chemical Engineering Science 2012, 75 , 1-13. https://doi.org/10.1016/j.ces.2012.03.002
    31. Hemayat Shekaari, Amir Kazempour. Solution Properties of Ternary D-Glucose + 1-Ethyl-3-methylimidazolium Ethyl Sulfate + Water Solutions at 298.15 K. Journal of Solution Chemistry 2011, 40 (9) , 1582-1595. https://doi.org/10.1007/s10953-011-9738-7
    32. Laura M. Grubbs, Shulin Ye, Mariam Saifullah, McCoy Cornelius McMillan-Wiggins, William E. Acree, Michael H. Abraham, Pamela Twu, Jared L. Anderson. Correlations for describing gas-to-ionic liquid partitioning at 323K based on ion-specific equation coefficient and group contribution versions of the Abraham model. Fluid Phase Equilibria 2011, 301 (2) , 257-266. https://doi.org/10.1016/j.fluid.2010.12.005
    33. Pei-Fang Yan, Qing-Shan Liu, Miao Yang, Xiu-Mei Liu, Zhi-Cheng Tan, Urs Welz-Biermann. Activity coefficients at infinite dilution of organic solutes in N-alkylpyridinium bis(trifluoromethylsulfonyl)imide ([CnPY][NTf2], n=2,4,5) using gas–liquid chromatography. The Journal of Chemical Thermodynamics 2010, 42 (12) , 1415-1422. https://doi.org/10.1016/j.jct.2010.06.009
    34. Lourdes F. Vega, Oriol Vilaseca, Fèlix Llovell, Jordi S. Andreu. Modeling ionic liquids and the solubility of gases in them: Recent advances and perspectives. Fluid Phase Equilibria 2010, 294 (1-2) , 15-30. https://doi.org/10.1016/j.fluid.2010.02.006
    35. Hemayat Shekaari, Sedighehnaz S. Mousavi. Volumetric properties of ionic liquid 1,3-dimethylimidazolium methyl sulfate+molecular solvents at T=(298.15–328.15)K. Fluid Phase Equilibria 2010, 291 (2) , 201-207. https://doi.org/10.1016/j.fluid.2010.01.002
    36. Urszula Domańska, Marek Królikowski, Kamil Paduszyński. Phase equilibria study of the binary systems (N-butyl-3-methylpyridinium tosylate ionic liquid+an alcohol). The Journal of Chemical Thermodynamics 2009, 41 (8) , 932-938. https://doi.org/10.1016/j.jct.2009.03.008
    37. Hemayat Shekaari, Sedighehnaz S. Mousavi. Measurement and modeling of osmotic coefficients of aqueous solution of ionic liquids using vapor pressure osmometry method. Fluid Phase Equilibria 2009, 279 (1) , 73-79. https://doi.org/10.1016/j.fluid.2009.02.007
    38. Hemayat Shekaari, Sedighehnaz S. Mousavi, Yagoub Mansoori. Thermophysical Properties of Ionic Liquid, 1-Pentyl-3-methylimidazolium Chloride in Water at Different Temperatures. International Journal of Thermophysics 2009, 30 (2) , 499-514. https://doi.org/10.1007/s10765-009-0566-6
    39. Svetlana A. Kozlova, Sergey P. Verevkin, Andreas Heintz, Tim Peppel, Martin Köckerling. Activity coefficients at infinite dilution of hydrocarbons, alkylbenzenes, and alcohols in the paramagnetic ionic liquid 1-butyl-3-methyl-imidazolium tetrachloridoferrate(III) using gas–liquid chromatography. The Journal of Chemical Thermodynamics 2009, 41 (3) , 330-333. https://doi.org/10.1016/j.jct.2008.09.004
    40. Hemayat Shekaari, Sedighehnaz S. Mousavi. Influence of alkyl chain on the thermodynamic properties of aqueous solutions of ionic liquids 1-alkyl-3-methylimidazolium bromide at different temperatures. The Journal of Chemical Thermodynamics 2009, 41 (1) , 90-96. https://doi.org/10.1016/j.jct.2008.07.011
    41. Hemayat Shekaari, Mohammed Taghi Zafarani-Moattar. Osmotic coefficients of some imidazolium based ionic liquids in water and acetonitrile at temperature 318.15K. Fluid Phase Equilibria 2007, 254 (1-2) , 198-203. https://doi.org/10.1016/j.fluid.2007.03.019
    42. Andreas Heintz, Sergey P. Verevkin, Jochen K. Lehmann, Tatiana V. Vasiltsova, Daniel Ondo. Activity coefficients at infinite dilution and enthalpies of solution of methanol, 1-butanol, and 1-hexanol in 1-hexyl-3-methyl-imidazolium bis(trifluoromethyl-sulfonyl) imide. The Journal of Chemical Thermodynamics 2007, 39 (2) , 268-274. https://doi.org/10.1016/j.jct.2006.07.006
    Download PDF
    Go to Journal of Chemical & Engineering Data
    Get e-Alerts
    Get e-Alerts

    Journal of Chemical & Engineering Data

    Cite this: J. Chem. Eng. Data 2006, 51, 1, 213–218
    Click to copy citationCitation copied!
    https://doi.org/10.1021/je050334+
    Published November 4, 2005
    Copyright © 2006 American Chemical Society
    Request reuse permissions

    Article Views

    571

    Altmetric

    -

    Citations

    42
    Learn about these metrics

    Article Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.

    Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.

    The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated.