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Liquid Properties of Ionic Liquids Based on Phosphonium Cations with (Alkylthio)alkyl Groups

  • Hideaki Shirota*
    Hideaki Shirota
    Department of Chemistry, Chiba University, 1-33 Yayoi, Inage-ku, Chiba 263-8522, Japan
    *E-mail: [email protected]
  • Kotaro Takahashi
    Kotaro Takahashi
    Department of Chemistry, Chiba University, 1-33 Yayoi, Inage-ku, Chiba 263-8522, Japan
  • Masatoshi Ando
    Masatoshi Ando
    Department of Chemistry, Chiba University, 1-33 Yayoi, Inage-ku, Chiba 263-8522, Japan
  • , and 
  • Shohei Kakinuma
    Shohei Kakinuma
    Department of Chemistry, Chiba University, 1-33 Yayoi, Inage-ku, Chiba 263-8522, Japan
Cite this: J. Chem. Eng. Data 2019, 64, 11, 4701–4707
Publication Date (Web):April 19, 2019
https://doi.org/10.1021/acs.jced.9b00033
Copyright © 2019 American Chemical Society

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    Abstract

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    Herein, we report the liquid properties, that is, densities, viscosities, electrical conductivities, surface tensions, melting points, and glass transition temperatures, of 18 novel sulfur-containing phosphonium cation- (triethyl[(methylthio)methyl]phosphonium, triethyl[2-(methylthio)ethyl]phosphonium, triethyl[2-(ethylthio)ethyl]phosphonium, tributyl[(methylthio)methyl]phosphonium, tributyl[2-(methylthio)ethyl]phosphonium, tributyl[2-(ethylthio)ethyl]phosphonium) based ionic liquids with bis(trifluoromethylsulfonyl)amide, bis(fluorosulfonyl)amide, and tetrafluoroborate anions. The effects of the (alkylthio)alkyl groups on the viscosity and surface tension of the ionic liquids are very different from those of common alkyl groups in typical ionic liquids.

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    The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acs.jced.9b00033.

    • Details of synthetic procedures including analytical results (1H NMR and elemental analysis) and water contents of the ILs in this study (PDF)

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    Cited By

    This article is cited by 8 publications.

    1. Masatoshi Ando, Maharoof Koyakkat, Tadashi Ueda, Taketoshi Minato, Hideaki Shirota. Wettability and Surface Tension of Imidazolium, Ammonium, and Phosphonium Bis(fluorosulfonyl)amide Ionic Liquids: Comparison between Pentyl, Ethoxyethyl, and Ethylthioethyl Groups. Langmuir 2023, 39 (34) , 12090-12098. https://doi.org/10.1021/acs.langmuir.3c01375
    2. Raphael Ogbodo, Waruni V. Karunaratne, Gobin Raj Acharya, Matthew S. Emerson, Mehreen Mughal, Ho Martin Yuen, Nicole Zmich, Shameir Nembhard, Furong Wang, Hideaki Shirota, Sharon I. Lall-Ramnarine, Edward W. Castner, Jr., James F. Wishart, Andrew J. Nieuwkoop, Claudio J. Margulis. Structural Origins of Viscosity in Imidazolium and Pyrrolidinium Ionic Liquids Coupled with the NTf2– Anion. The Journal of Physical Chemistry B 2023, 127 (28) , 6342-6353. https://doi.org/10.1021/acs.jpcb.3c02604
    3. Masatoshi Ando, Kaoru Ohta, Tateki Ishida, Ryohei Koido, Hideaki Shirota. Physical Properties and Low-Frequency Polarizability Anisotropy and Dipole Responses of Phosphonium Bis(fluorosulfonyl)amide Ionic Liquids with Pentyl, Ethoxyethyl, or 2-(Ethylthio)ethyl Group. The Journal of Physical Chemistry B 2023, 127 (2) , 542-556. https://doi.org/10.1021/acs.jpcb.2c07466
    4. Nedher Sánchez-Ramírez, Ivonne E. Monje, Daniel Bélanger, Pedro H.C. Camargo, Roberto M. Torresi. High rate and long-term cycling of silicon anodes with phosphonium-based ionic liquids as electrolytes for lithium-ion batteries. Electrochimica Acta 2023, 439 , 141680. https://doi.org/10.1016/j.electacta.2022.141680
    5. Sepideh Jalali-Mola, Morteza Torabi, Meysam Yarie, Mohammad Ali Zolfigol. Acidic tributyl phosphonium-based ionic liquid: an efficient catalyst for preparation of diverse pyridine systems via a cooperative vinylogous anomeric-based oxidation. RSC Advances 2022, 12 (53) , 34730-34739. https://doi.org/10.1039/D2RA04631H
    6. Alexis E. Langtry, Kaitlyn B. Thompson, Neil D. Redeker, Ashlee S. Quintana, Denise L. Bui, Kevin T. Greeson, Nicolas Cena, Jacob C. Marcischak, Levi M. J. Moore, Kamran B. Ghiassi. Fluorinated phosphonium salts and ionic liquids prepared via thiol-ene click chemistry: a physical and thermal property study. Journal of Molecular Liquids 2022, 359 , 119282. https://doi.org/10.1016/j.molliq.2022.119282
    7. Hideaki Shirota, Masatoshi Ando, Shohei Kakinuma, Kotaro Takahashi. Ultrafast Dynamics in Nonaromatic Cation Based Ionic Liquids: A Femtosecond Raman-Induced Kerr Effect Spectroscopic Study. Bulletin of the Chemical Society of Japan 2020, 93 (12) , 1520-1539. https://doi.org/10.1246/bcsj.20200198
    8. Tehreem Naveed, Rehan Zahid, Riaz Ahmad Mufti, Muhammad Waqas, Muhammad Talha Hanif. A review on tribological performance of ionic liquids as additives to bio lubricants. Proceedings of the Institution of Mechanical Engineers, Part J: Journal of Engineering Tribology 2020, 38 , 135065012097380. https://doi.org/10.1177/1350650120973805

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