ACS Publications. Most Trusted. Most Cited. Most Read
My Activity
CONTENT TYPES

Figure 1Loading Img

Extraction of Benzene from Aliphatic Compounds Using Commercial Ionic Liquids as Solvents: Study of the Liquid–Liquid Equilibrium at T = 298.15 K

View Author Information
Advanced Separation Processes Group, Department of Chemical Engineering, University of Vigo, Campus Lagoas-Marcosende, 36310 Vigo, Spain
LSRE-Laboratory of Separation and Reaction Engineering, Associate Laboratory LSRE/LCM, Department of Chemical Engineering, Faculty of Engineering, University of Porto, Rua Dr. Roberto Frias s/n, Porto 4200-465, Portugal
E-mail: [email protected]. Tel.: +34 986 812 422. Fax: +34 986 812 382.
Cite this: J. Chem. Eng. Data 2011, 56, 8, 3376–3383
Publication Date (Web):July 22, 2011
https://doi.org/10.1021/je200334e
Copyright © 2011 American Chemical Society

    Article Views

    941

    Altmetric

    -

    Citations

    LEARN ABOUT THESE METRICS
    Other access options
    Supporting Info (1)»

    Abstract

    In this paper, the liquid extraction of benzene from aliphatic compounds (heptane, octane, cyclooctane, and methylcyclohexane) using commercial ionic liquids (ILs; 1-propyl-3-methylimidazolium bis{trifluoromethylsulfonyl}imide, [PMim][NTf2], and 1-butyl-3-methylimidazolium bis{trifluoromethylsulfonyl}imide, [BMim][NTf2]) as solvents was studied. The liquid–liquid equilibrium (LLE) data for five ternary systems (aliphatic compound + benzene + IL) are reported at T = 298.15 K and atmospheric pressure. The cloud point method was used to determine the solubility curves, and the tie-line compositions were obtained by density measurements. From the experimental LLE data, the selectivity and the solute distribution ratio were calculated. The degree of consistency of the tie-lines was tested using the Othmer–Tobias equation, and the experimental LLE data were correlated using nonrandom two-liquid (NRTL) and universal quasichemical (UNIQUAC) thermodynamic models. Moreover, a systematic study about the influence of the size of the aliphatic and IL on the aromatic extraction was carried out.

    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. You can change your affiliated institution below.

    Supporting Information

    ARTICLE SECTIONS
    Jump To

    Solubility curves, validation points, and Othmer–Tobias parameters, at T = 298.15 K and atmospheric pressure. This material is available free of charge via the Internet at http://pubs.acs.org.

    Terms & Conditions

    Most electronic Supporting Information files are available without a subscription to ACS Web Editions. Such files may be downloaded by article for research use (if there is a public use license linked to the relevant article, that license may permit other uses). Permission may be obtained from ACS for other uses through requests via the RightsLink permission system: http://pubs.acs.org/page/copyright/permissions.html.

    Cited By

    This article is cited by 41 publications.

    1. Abdullah Aljasmi, Adel S. AlJimaz, Khaled H. A. E. AlKhaldi, Mohammad S. AlTuwaim. Dependency of Physicochemical Properties of Imidazolium Bis(Trifluoromethylsulfonyl)Imide-Based Ionic Liquids on Temperature and Alkyl Chain. Journal of Chemical & Engineering Data 2022, 67 (4) , 858-868. https://doi.org/10.1021/acs.jced.1c00919
    2. Suyong Han, Keshav Raghuvanshi, Milad Abolhasani. Accelerated Material-Efficient Investigation of Switchable Hydrophilicity Solvents for Energy-Efficient Solvent Recovery. ACS Sustainable Chemistry & Engineering 2020, 8 (8) , 3347-3356. https://doi.org/10.1021/acssuschemeng.9b07304
    3. Roberto I. Canales and Joan F. Brennecke . Comparison of Ionic Liquids to Conventional Organic Solvents for Extraction of Aromatics from Aliphatics. Journal of Chemical & Engineering Data 2016, 61 (5) , 1685-1699. https://doi.org/10.1021/acs.jced.6b00077
    4. Sandra Corderí, Elena Gómez, Noelia Calvar, and Ángeles Domínguez . Measurement and Correlation of Liquid–Liquid Equilibria for Ternary and Quaternary Systems of Heptane, Cyclohexane, Toluene, and [EMim][OAc] at 298.15 K. Industrial & Engineering Chemistry Research 2014, 53 (22) , 9471-9477. https://doi.org/10.1021/ie500973k
    5. Monika Geppert-Rybczyńska and Magdalena Sitarek . Acoustic and Volumetric Properties of Binary Mixtures of Ionic Liquid 1-Butyl-3-methylimidazolium Bis(trifluoromethylsulfonyl)imide with Acetonitrile and Tetrahydrofuran. Journal of Chemical & Engineering Data 2014, 59 (4) , 1213-1224. https://doi.org/10.1021/je400781b
    6. Luís Fernández, Diego Montaño, Juan Ortega, and Francisco J. Toledo . Binary Liquid–Liquid Equilibria for Systems of Mono- or Disubstituted Haloalkanes (Cl, Br) and Pyridinium-Based Ionic Liquids. Advances in the Experimentation and Interpretation of Results. Industrial & Engineering Chemistry Research 2013, 52 (33) , 11758-11766. https://doi.org/10.1021/ie401710f
    7. Abdullah Aljasmi, Adel S. AlJimaz, Khaled H. A. E. AlKhaldi, Mohammad S. AlTuwaim, Meshal F. Alhasan, Abdulaziz Alnajjar. Temperature and Alkyl Chain Dependence of Physicochemical Properties of Pyrrolidinium‑ and Imidazolium-Based Ionic Liquids. Journal of Solution Chemistry 2024, 111 https://doi.org/10.1007/s10953-023-01358-0
    8. Abdullah Aljasmi, Adel S. AlJimaz, Khaled H.A.E. AlKhaldi, Mohammad S. AlTuwaim. Effect of temperature and alkyl chain length on the physicochemical properties of pyridinium bis(trifluoromethylsulfonyl)imide-based ionic liquids. Chemical Thermodynamics and Thermal Analysis 2022, 8 , 100099. https://doi.org/10.1016/j.ctta.2022.100099
    9. Xinxin Wang, Qing Zhou. Refractive Index of Ionic Liquids. 2022, 1161-1167. https://doi.org/10.1007/978-981-33-4221-7_104
    10. Abdullah Aljasmi, Khaled Alkhaldi, Adel Aljimaz, Mohammad Altuwaim. Effect of Temperature and Alkyl Chain Length on the Physicochemical Properties of Pyridinium Bis(Trifluoromethylsulfonyl)Imide-Based Ionic Liquids. SSRN Electronic Journal 2022, 72 https://doi.org/10.2139/ssrn.4156496
    11. Chen Liu, Di Zhao, Haiyong Zhang, Yonggang Wang, Hongcun Bai, Qian Liu. Cumene extraction separation from alkanes using DMSO: Influence of the alkane structure. Fluid Phase Equilibria 2021, 550 , 113236. https://doi.org/10.1016/j.fluid.2021.113236
    12. Chen Liu, Haiyong Zhang, Yonggang Wang, Hongcun Bai, Di Zhao, Qian Liu. The physical nature of the interaction in DMSO extraction separation of C 8 H 10 isomer/ n -decane systems. Physical Chemistry Chemical Physics 2021, 23 (39) , 22629-22639. https://doi.org/10.1039/D1CP03128G
    13. Santosh R. P. Bandlamudi, Jimmie L. McGehee, Albaraa D. Mando, Mohammad Soltani, C. Heath Turner, James H. Davis, Kevin N. West, Brooks D. Rabideau. Understanding liquid–liquid equilibria in binary mixtures of hydrocarbons with a thermally robust perarylphosphonium-based ionic liquid. RSC Advances 2021, 11 (50) , 31328-31338. https://doi.org/10.1039/D1RA06268A
    14. Bukke Vani, Swayampakula Kalyani, Manideep Pabba, Sundergopal Sridhar. Forward osmosis aided concentration of lycopene carotenoid from watermelon juice. Journal of Chemical Technology & Biotechnology 2021, 96 (7) , 1960-1973. https://doi.org/10.1002/jctb.6720
    15. Zhiyun Chen, Doudou Liu, Yuxiao Bai, Tianxiang Yin, Weiguo Shen. Liquid–Liquid Phase Equilibria of Binary Solutions of {1-Butyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide + 1-Butanol or 2-Methyl-1-propanol}. Journal of Solution Chemistry 2021, 50 (3) , 299-314. https://doi.org/10.1007/s10953-021-01053-y
    16. Yicang Guo, Fengming Shi, Qipeng Shu, Xiaoyong Yue, Cheng Wang, Lei Tao, Jinlong Li. Liquid-liquid equilibrium for n-hexane + benzene + sulfolane, + 1-ethyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide ([EMIM][NTf2]), + 1-ethyl-3-methylimidazolium ethylsulfate ([EMIM][EtSO4]) and + the mixtures of [EMIM][NTf2] and [EMIM][EtSO4]. Fluid Phase Equilibria 2021, 529 , 112882. https://doi.org/10.1016/j.fluid.2020.112882
    17. Xinxin Wang, Qing Zhou. Refractive Index of Ionic Liquids. 2020, 1-8. https://doi.org/10.1007/978-981-10-6739-6_104-1
    18. L.M. Ramenskaya, E.P. Grishina, N.O. Kudryakova. Physicochemical features of short-chain 1-alkyl-3-methylimidazolium bis(trifluoromethylsulfonyl)-imide ionic liquids containing equilibrium water absorbed from air. Journal of Molecular Liquids 2018, 272 , 759-765. https://doi.org/10.1016/j.molliq.2018.10.005
    19. Sraddha Agrawal, Hemant K. Kashyap. Structures of binary mixtures of ionic liquid 1-butyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide with primary alcohols: The role of hydrogen-bonding. Journal of Molecular Liquids 2018, 261 , 337-349. https://doi.org/10.1016/j.molliq.2018.03.124
    20. K. Oster, C. Hardacre, J. Jacquemin, A.P.C. Ribeiro, A. Elsinawi. Understanding the heat capacity enhancement in ionic liquid-based nanofluids (ionanofluids). Journal of Molecular Liquids 2018, 253 , 326-339. https://doi.org/10.1016/j.molliq.2018.01.025
    21. Danijela Soldatović, Jelena Vuksanović, Ivona Radović, Zoran Višak, Mirjana Kijevčanin. Excess molar volumes and viscosity behaviour of binary mixtures of aniline/or N,N-dimethylaniline with imidazolium ionic liquids having triflate or bistriflamide anion. The Journal of Chemical Thermodynamics 2017, 109 , 137-154. https://doi.org/10.1016/j.jct.2017.02.007
    22. Fariborz Shaahmadi, Mohammad Amin Anbaz. The prediction of liquid-liquid equilibria for benzene/alkane/ionic liquids mixtures using intelligent models. Journal of Molecular Liquids 2017, 232 , 396-407. https://doi.org/10.1016/j.molliq.2017.02.108
    23. M.J. Salar-García, V.M. Ortiz-Martínez, F.J. Hernández-Fernández, A.P. de los Ríos, J. Quesada-Medina. Ionic liquid technology to recover volatile organic compounds (VOCs). Journal of Hazardous Materials 2017, 321 , 484-499. https://doi.org/10.1016/j.jhazmat.2016.09.040
    24. Ismael Díaz, José Palomar, Manuel Rodríguez, Juan de Riva, Víctor Ferro, Emilio J. González. Ionic liquids as entrainers for the separation of aromatic–aliphatic hydrocarbon mixtures by extractive distillation. Chemical Engineering Research and Design 2016, 115 , 382-393. https://doi.org/10.1016/j.cherd.2016.07.012
    25. Snežana Papović, Marija Bešter-Rogač, Milan Vraneš, Slobodan Gadžurić. The effect of the alkyl chain length on physicochemical features of (ionic liquids +γ-butyrolactone) binary mixtures. The Journal of Chemical Thermodynamics 2016, 99 , 1-10. https://doi.org/10.1016/j.jct.2016.03.034
    26. Sandra Corderí, Elena Gómez, Ángeles Domínguez, Noelia Calvar. (Liquid+liquid) equilibrium of ternary and quaternary systems containing heptane, cyclohexane, toluene and the ionic liquid [EMim][N(CN)2]. Experimental data and correlation. The Journal of Chemical Thermodynamics 2016, 94 , 16-23. https://doi.org/10.1016/j.jct.2015.10.018
    27. Jesse R. Vanderveen, Roberto I. Canales, Yi Quan, Courtney B. Chalifoux, Mark A. Stadtherr, Joan F. Brennecke, Philip G. Jessop. Non-random two-liquid modelling of switchable-hydrophilicity solvent systems: N,N -Dimethylcyclohexanamine, water, and toluene. Fluid Phase Equilibria 2016, 409 , 150-156. https://doi.org/10.1016/j.fluid.2015.09.032
    28. Naved I. Malek, Sushma P. Ijardar. Binary mixtures of ([C 4 mim][NTf 2 ] + molecular organic solvents): Thermophysical, acoustic and transport properties at various compositions and temperatures. The Journal of Chemical Thermodynamics 2016, 93 , 75-85. https://doi.org/10.1016/j.jct.2015.09.022
    29. Snežana Papović, Milan Vraneš, Slobodan Gadžurić. A comprehensive study of {γ-butyrolactone + 1-methyl-3-propylimidazolium bis(trifluoromethylsulfonyl)imide} binary mixtures. The Journal of Chemical Thermodynamics 2015, 91 , 360-368. https://doi.org/10.1016/j.jct.2015.07.048
    30. Indra Bahadur, Mbongeni Mabaso, Gan Redhi, Prashant Singh, Sudharsan Kumar, Kandasamy Moodley. Separation of aromatic solvents from oil refinery reformates by a newly designed ionic liquid using gas chromatography with flame ionization detection. Journal of Separation Science 2015, 38 (6) , 951-957. https://doi.org/10.1002/jssc.201400990
    31. Ke Yuan, Haining Kang, Zhenfeng Yue, Lihua Yang, Li Lin, Xiaowei Wang, Tiangang Luan. Determination of 13 endocrine disrupting chemicals in sediments by gas chromatography–mass spectrometry using subcritical water extraction coupled with dispersed liquid–liquid microextraction and derivatization. Analytica Chimica Acta 2015, 866 , 41-47. https://doi.org/10.1016/j.aca.2015.02.011
    32. Soo-Hyun You, In-Yong Jeong, So-Jin Park. Liquid–liquid equilibria in the ternary systems {hexadecane+BTX aromatics+2-methoxyethanol or acetonitrile} at 298.15K. Fluid Phase Equilibria 2015, 389 , 9-15. https://doi.org/10.1016/j.fluid.2015.01.002
    33. Irene Domínguez, Emilio J. González, Ángeles Domínguez. Liquid extraction of aromatic/cyclic aliphatic hydrocarbon mixtures using ionic liquids as solvent: Literature review and new experimental LLE data. Fuel Processing Technology 2014, 125 , 207-216. https://doi.org/10.1016/j.fuproc.2014.04.001
    34. Gholamreza VAKİLİ-NEZHAAD, Mostafa VATANİ. Application of Genetic Algorithm to Calculation of Three-Suffix Margules Parameters in Ternary Extraction Ionic Liquid Systems. International Journal of Thermodynamics 2014, 17 (1) , 1-6. https://doi.org/10.5541/ijot.76986
    35. Sarwono Mulyono, Hanee F. Hizaddin, Inas M. Alnashef, Mohd A. Hashim, Anis H. Fakeeha, Mohamed K. Hadj-Kali. Separation of BTEX aromatics from n-octane using a (tetrabutylammonium bromide + sulfolane) deep eutectic solvent – experiments and COSMO-RS prediction. RSC Advances 2014, 4 (34) , 17597. https://doi.org/10.1039/c4ra01081g
    36. Noelia Calvar, Irene Domínguez, Elena Gómez, Jose Palomar, Ángeles Domínguez. Evaluation of ionic liquids as solvent for aromatic extraction: Experimental, correlation and COSMO-RS predictions. The Journal of Chemical Thermodynamics 2013, 67 , 5-12. https://doi.org/10.1016/j.jct.2013.07.011
    37. Sandra Corderí, Emilio J. González, Noelia Calvar, Ángeles Domínguez. Application of [HMim][NTf2], [HMim][TfO] and [BMim][TfO] ionic liquids on the extraction of toluene from alkanes: Effect of the anion and the alkyl chain length of the cation on the LLE. The Journal of Chemical Thermodynamics 2012, 53 , 60-66. https://doi.org/10.1016/j.jct.2012.04.015
    38. Raquel G. Seoane, Emilio J. González, Begoña González. 1-Alkyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide ionic liquids as solvents in the separation of azeotropic mixtures. The Journal of Chemical Thermodynamics 2012, 53 , 152-157. https://doi.org/10.1016/j.jct.2012.04.026
    39. Mostafa Vatani, Morteza Asghari, Gholamreza Vakili-Nezhaad. Application of Genetic Algorithm to the calculation of parameters for NRTL and Two-Suffix Margules models in ternary extraction ionic liquid systems. Journal of Industrial and Engineering Chemistry 2012, 18 (5) , 1715-1720. https://doi.org/10.1016/j.jiec.2012.03.008
    40. Maciej Zawadzki, Urszula Domańska. Thermodynamic properties of the N-octylquinolinium bis{(trifluoromethyl)sulfonyl}imide. The Journal of Chemical Thermodynamics 2012, 48 , 276-283. https://doi.org/10.1016/j.jct.2011.12.037
    41. Raquel G. Seoane, Elena Gómez, Emilio J. González, Ángeles Domínguez. (Liquid + liquid) equilibria for the ternary mixtures (alkane + toluene + ionic liquid) at T= 298.15 K: Influence of the anion on the phase equilibria. The Journal of Chemical Thermodynamics 2012, 47 , 402-407. https://doi.org/10.1016/j.jct.2011.11.027

    Pair your accounts.

    Export articles to Mendeley

    Get article recommendations from ACS based on references in your Mendeley library.

    Pair your accounts.

    Export articles to Mendeley

    Get article recommendations from ACS based on references in your Mendeley library.

    You’ve supercharged your research process with ACS and Mendeley!

    STEP 1:
    Click to create an ACS ID

    Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

    Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

    Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

    MENDELEY PAIRING EXPIRED
    Your Mendeley pairing has expired. Please reconnect