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Phosphonium ionic liquids as new, reactive extractants of lactic acid

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Abstract

Solvent properties of ionic liquids with trihexyltetradecylphosphonium cation and bis(2,4,4-trimethylpentyl)phosphinate anion (Cyphos IL-104) or chloride anion (Cyphos IL-101) were studied. IL-104 effectively extracted lactic acid (LA) with distribution coefficients above 40 at low acid concentrations. IL-104 extracted only undissociated acid (LAH) what supported the coordination mechanism of lactic acid extraction via H-bonding. In the extraction of lactic acid by phosphonium chloride (IL-101) an ion-exchange mechanism contributed remarkably to the extraction especially at basic pH where anionic form of this acid predominated. A high solubility of water in hydrophobic IL-104 up to 14.4 mass % was connected with the formation of reverse micelles. A dual mechanism of water extraction to phosphonium ionic liquids was identified, which consisted of water incorporation into reverse micelles and the inclusion of water into the hydrated complex of lactic acid with ionic liquid (IL). The extraction of lactic acid caused splitting of reverse micelles with liberation of water from the solvent. In the saturated solvent only hydration water remained in the complex of lactic acid with phosphonium ionic liquid, with the suggested structure (LAH)p(IL)(H2O)2, where the value of p ranged from 1 to 3.

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References

  1. Rogers, R. D. and Seddon, K. R., Ionic Liquids. Industrial Applications to Green Chemistry, ACS Symp. Ser., Vol. 818. ACS, Washington, 2002.

    Google Scholar 

  2. Wasserscheid, P. and Welton, T., Ionic Liquids in Synthesis. Wiley-VCH, Weinheim, 2003.

    Google Scholar 

  3. Huddleston, J. G., Willauer, H. D., Swatloski, R. P., Visser, A. E., and Rogers, R. D., Chem. Commun. 1998, 1765.

  4. Cull, S. G., Holbrey, J. D., Vargas-Mora, V., Seddon, K. R., and Lye, G. J., Biotechnol. Bioeng. 69, 227 (2000).

    Article  CAS  Google Scholar 

  5. Visser, A. E., Holbrey, J. D., and Rogers, R. D., Chem. Commun. 2001, 2484.

  6. Matsumoto, M., Mochiduki, K., Fukunishi, K., and Kondo, K., Sep. Purif. Technol. 40, 97 (2004).

    Article  CAS  Google Scholar 

  7. McFarlane, J., Ridenour, W. B., Luo, H., Hunt, R. D., DePaoli, D. W., and Ren, R. X., Sep. Sci. Technol. 40, 1245 (2005).

    CAS  Google Scholar 

  8. Marták, J. and Schlosser, Š., in Proc. PERMEA 2005, p. 11, full text on CD ROM, Polanica, 2005.

  9. Visser, A. E., Swatloski, R. P., Reichert, W. M., Griffin, S. T., and Rogers, R. D., Ind. Eng. Chem. Res. 39, 3596 (2000).

    Article  CAS  Google Scholar 

  10. Nakashima, K., Kubota, F., Maruyama, T., and Goto, M., Ind. Eng. Chem. Res. 44, 4368 (2005).

    Article  CAS  Google Scholar 

  11. Smirnova, S. V., Torocheshnikova, I. I., Formanovsky, A. A., and Pletnev, I. V., Anal. Bioanal. Chem. 378, 1369 (2004).

    Article  CAS  Google Scholar 

  12. Bradaric, C. J., Downard, A., Kennedy, C., Robertson, A. J., and Zhou, Y. H., Green Chemistry 5, 143 (2003).

    Article  CAS  Google Scholar 

  13. Marták, J. and Schlosser, Š., accepted for publication in Sep. Purif. Technol.

  14. Cardoso, M. M., Barradas, M. J., Kroner, K. H., and Crespo, J. G., J. Chem. Technol. Biotechnol. 74, 801 (1999).

    Article  CAS  Google Scholar 

  15. Schlosser, Š., Kertész, R., and Marták, J., Sep. Purif. Technol. 41, 237 (2005).

    Article  CAS  Google Scholar 

  16. Marták, J. and Schlosser, Š., Desalination 199, 518 (2006).

    Article  Google Scholar 

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Authors and Affiliations

  1. Institute of Chemical and Environmental Engineering, Faculty of Chemical and Food Technology, Slovak University of Technology, Radlinského 9, 812 37, Bratislava, Slovakia

    J. Marták & Š. Schlosser

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  1. J. Marták
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  2. Š. Schlosser
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Marták, J., Schlosser, Š. Phosphonium ionic liquids as new, reactive extractants of lactic acid. Chem. Pap. 60, 395–398 (2006). https://doi.org/10.2478/s11696-006-0072-2

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  • DOI: https://doi.org/10.2478/s11696-006-0072-2

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