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Electrospray ionization mass spectrometry of ionic liquids and determination of their solubility in water

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Abstract

Electrospray ionization mass spectrometry is used to detect both the cations (C+) and the anions (A−) of ionic liquids (CA). In this study, the ionic liquids are diluted with aqueous methanol before injection. In addition to the main peaks of the parent ions, fragmentation products are observed upon increasing the cone voltage, whereas aggregates of the parent ion with one or more ionic liquid molecules (e.g., C(CA)n +, A(CA)n −) are observed upon decreasing the cone voltage. The ions of several ionic liquids in a mixture are also detected and the ratios of their concentrations estimated. A method is developed to determine quantitatively the concentration of an ionic liquid in solution by using the cation and anion of another ionic liquid as internal standards. By using this method, the solubilities in water at room temperature (22±1 °C) of three typical hydrophobic ionic liquids have been determined: 0.70±0.08 g L−1 for methyltributylammonium bis(trifluoromethylsulfonyl)imide (MeBu3NNTf2), 6.0±0.5 g L−1 for butylmethylpyrrolidinium bis(trifluoromethylsulfonyl)imide (BuMePyrNTf2), and 18.6±0.7 g L−1 for 1-butyl-3-methylimidazolium hexafluorophosphate (BMIPF6).

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Acknowledgements

We thank Drs. Stephen Stein and Michael Welch for helpful discussions.

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Author notes

  1. Z. B. Alfassi

    Present address: Ben Gurion University of the Negev, Beer Sheva, Israel

  2. B. L. Milman

    Present address: D.I. Mendeleyev Institute for Metrology, St. Petersburg, Russia

Authors and Affiliations

  1. Physical and Chemical Properties Division, National Institute of Standards and Technology, Gaithersburg, MD, 20899, USA

    Z. B. Alfassi, R. E. Huie, B. L. Milman & P. Neta

Authors
  1. Z. B. Alfassi
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  2. R. E. Huie
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  3. B. L. Milman
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  4. P. Neta
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Corresponding author

Correspondence to P. Neta.

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Alfassi, Z.B., Huie, R.E., Milman, B.L. et al. Electrospray ionization mass spectrometry of ionic liquids and determination of their solubility in water. Anal Bioanal Chem 377, 159–164 (2003). https://doi.org/10.1007/s00216-003-2033-8

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  • DOI: https://doi.org/10.1007/s00216-003-2033-8

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