Skip to main content
SpringerLink
Log in

Solvent Extraction of Some Univalent Cations into Nitrobenzene by Using Cesium Dicarbollylcobaltate and Four Bis(crown-6) Ether Derivatives of Calix[4]arene

  • Published:
Journal of Solution Chemistry Aims and scope Submit manuscript

Abstract

On the basis of extraction experiments and \(\gamma\)-activity measurements, the exchange extraction constants corresponding to the general equilibrium M+(aq) + CsL+(nb) ⇌ ML+(nb) + Cs+(aq) occurring in the two-phase water–nitrobenzene system (M+ = K+, Rb+, Ag+, Tl+; L = bis(crown-6) ether derivatives of calix[4]arene, where aq = aqueous phase and nb = nitrobenzene phase) were evaluated. Moreover, the stability constants of the proven ML+ complexes in water-saturated nitrobenzene were calculated and are discussed.

Graphical Abstract

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Scheme 1
Scheme 2

Similar content being viewed by others

References

  1. Böhmer, V.: Calixarenes, macrocycles with (almost) unlimited possibilities. Angew. Chem. Int. Ed. Engl. 34, 713–745 (1995)

    Article  Google Scholar 

  2. Gutsche, C.D.: Calixarenes Revisited. The Royal Society of Chemistry, Cambridge (1998)

    Google Scholar 

  3. Alfieri, C., Dradi, E., Pochini, A., Ungaro, R., Andreetti, G.D.: Synthesis, and X-ray crystal and molecular structure of a novel macro-bicyclic ligand: crowned p-t-butyl-calix[4]arene. J. Chem. Soc. Chem. Commun. 19, 1075–1077 (1983)

    Article  Google Scholar 

  4. Asfari, Z., Wenger, S., Vicens, J.: Calixcrowns and related molecules. J. Incl. Phenom. 19, 137–148 (1994)

    Article  CAS  Google Scholar 

  5. Kim, J.S., Vicens, J.: Progress of calixcrowns chemistry. J. Incl. Phenom. Macrocycl. Chem. 63, 189–193 (2009)

    Article  CAS  Google Scholar 

  6. Ungaro, R., Casnati, A., Ugozzoli, F., Pochini, A., Dozol, J.F., Hill, C., Rouquette, H.: 1,3-Dialkoxycalix[4]arene-crowns-6 in 1,3-alternate conformation: cesium-selective ligands that exploit cation-arene interactions. Angew. Chem. Int. Ed. Engl. 33, 1506–1509 (1994)

    Article  Google Scholar 

  7. Casnati, A., Pochini, A., Ungaro, R., Ugozzoli, F., Arnaud, F., Fanni, S., Schwing, M.J., Egberink, R.J.M., de Jong, F., Reinhoudt, D.N.: Synthesis, complexation, and membrane transport studies of 1,3-alternate calix[4]arene-crown-6 conformers: a new class of cesium selective ionophores. J. Am. Chem. Soc. 117, 2767–2777 (1995)

    Article  CAS  Google Scholar 

  8. Thuéry, P., Nierlich, M., Bryan, J.C., Lamare, V., Dozol, J.F., Asfari, Z., Vicens, J.: Crown ether conformations in 1,3-calix[4]arene bis(crown ethers): crystal structures of a caesium complex and solvent adducts and molecular dynamics simulations. J. Chem. Soc. Dalton Trans. 22, 4191–4202 (1997)

    Article  Google Scholar 

  9. Deng, Y., Sachleben, R.A., Moyer, B.A.: Equilibrium aspects of the extraction of caesium nitrate by dicyclohexano-21-crown-7, dibenzo-21-crown-7 and bis-[tert-alkylbenzo]-21-crown-7 in 1,2-dichloroethane. J. Chem. Soc. Faraday Trans. 91, 4215–4222 (1995)

    Article  CAS  Google Scholar 

  10. Sachleben, R.A., Bonnesen, P.V., Descazeaud, T., Haverlock, T.J., Urvoas, A., Moyer, B.A.: Surveying the extraction of cesium nitrate by 1,3-alternate-calix[4]arene-crown-6 ethers in 1,2-dichloroethane. Solvent Extr. Ion Exch. 17, 1445–1459 (1999)

    Article  CAS  Google Scholar 

  11. Haverlock, T.J., Bonnesen, P.V., Sachleben, R.A., Moyer, B.A.: Analysis of equilibria in the extraction of cesium nitrate by calix[4]arene-bis(t-octylbenzo-crown-6) in 1,2-dichloroethane. J. Incl. Phenom. Macrocycl. Chem. 36, 21–37 (2000)

    Article  CAS  Google Scholar 

  12. Wintergerst, M.P., Levitskaia, T.G., Moyer, B.A., Sessler, J.L., Delmau, L.H.: Calix[4]pyrrole: a new ion-pair receptor as demonstrated by liquid–liquid extraction. J. Am. Chem. Soc. 130, 4129–4139 (2008)

    Article  CAS  PubMed  Google Scholar 

  13. Makrlík, E., Vaňura, P.: Applications of the dicarbollylcobaltate(III) anion in the water/nitrobenzene extraction system. Talanta 32, 423–429 (1985)

    Article  PubMed  Google Scholar 

  14. Makrlík, E., Vaňura, P., Selucký, P.: Stability constants of some univalent cation complexes of 2,3-naphtho-15-crown-5 in nitrobenzene saturated with water. J. Solution Chem. 38, 1129–1138 (2009)

    Article  CAS  Google Scholar 

  15. Makrlík, E., Vaňura, P., Selucký, P.: Solvent extraction of europium and americium into phenyltrifluoromethyl sulfone by using synergistic mixture of hydrogen dicarbollylcobaltate and ‘‘classical’’ CMPO. J. Radioanal. Nucl. Chem. 283, 571–575 (2010)

    Article  CAS  Google Scholar 

  16. Toman, P., Makrlík, E., Vaňura, P., Kašička, V.: Protonation of benzo-18-crown-6: extraction and DFT study. Z. Phys. Chem. 225, 265–270 (2011)

    Article  CAS  Google Scholar 

  17. Makrlík, E., Toman, P., Vaňura, P.: Experimental and theoretical study on the complexation of the cesium cation with dibenzo-30-crown-10. J. Radioanal. Nucl. Chem. 292, 1137–1140 (2012)

    Article  CAS  Google Scholar 

  18. Makrlík, E., Spíchal, Z., Vaňura, P., Selucký, P.: Synergistic extraction of europium and americium into nitrobenzene by using hydrogen dicarbollylcobaltate and bis(diphenylphosphino)methane dioxide. J. Radioanal. Nucl. Chem. 295, 2135–2140 (2013)

    Article  CAS  Google Scholar 

  19. Romanovskiy, V.N., Smirnov, I.V., Babain, V.A., Todd, T.A., Herbst, R.S., Law, J.D., Brewer, K.N.: The universal solvent extraction (UNEX) process. I. Development of the UNEX process solvent for the separation of cesium, strontium and the actinides from acidic radioactive waste. Solvent Extr. Ion Exch. 19, 1–21 (2001)

    Article  CAS  Google Scholar 

  20. Law, J.D., Herbst, R.S., Todd, T.A., Romanovskiy, V.N., Babain, V.A., Esimantovskiy, V.M., Smirnov, I.V., Zaitsev, B.N.: The universal solvent extraction (UNEX) process. II. Flowsheet development and demonstration of the UNEX process for the separation of cesium, strontium and actinides from actual acidic radioactive waste. Solvent Extr. Ion Exch. 19, 23–36 (2001)

    Article  CAS  Google Scholar 

  21. Asfari, Z., Bressot, C., Vicens, J., Hill, C., Dozol, J.-F., Rouquette, H., Eymard, S., Lamare, V., Tournois, B.: Doubly crowned calix[4]arenes in the 1,3-alternate conformation as cesium-selective carriers in supported liquid membranes. Anal. Chem. 67, 3133–3139 (1995)

    Article  CAS  Google Scholar 

  22. Lamare, V., Dozol, J.F., Fuangswasdi, S., Arnaud-Neu, F., Thuéry, P., Nierlich, M., Asfari, Z., Vicens, J.: A new calix[4]arene-bis(crown ether) derivative displaying an improved caesium over sodium selectivity: molecular dynamics and experimental investigation of alkali-metal ion complexation. J. Chem. Soc. Perkin Trans. 2, 271–284 (1999)

    Article  Google Scholar 

  23. Hawthorne, M.F., Young, D.C., Andrews, T.D., Howe, D.V., Pilling, R.L., Pitts, A.D., Reintjes, M., Warren Jr., L.F., Wegner, P.A.: π–Dicarbollyl derivatives of the transition metals. Metallocene analogs. J. Am. Chem. Soc. 90, 879–896 (1968)

    Article  CAS  Google Scholar 

  24. Rais, J.: Individual extraction constants of univalent ions in the system water–nitrobenzene. Collect. Czech. Chem. Commun. 36, 3253–3262 (1971)

    Article  CAS  Google Scholar 

  25. Makrlík, E., Božek, F.: Individual extraction constants of some univalent cations in the water–nitrobenzene system. Pol. J. Chem. 72, 949–952 (1998)

    Google Scholar 

  26. Daňková, M., Makrlík, E., Vaňura, P.: Stability of the valinomycin–rubidium complex in water saturated nitrobenzene. J. Radioanal. Nucl. Chem. 221, 251–253 (1997)

    Article  Google Scholar 

  27. Makrlík, E., Vaňura, P.: Extraction of sodium picrate into nitrobenzene in the presence of valinomycin. ACH Models Chem. 135, 213–218 (1998)

    Google Scholar 

  28. Makrlík, E., Vaňura, P.: Experimental evidence for a valinomycin–proton complex. Monatsh. Chem. 137, 157–161 (2006)

    Article  CAS  Google Scholar 

  29. Makrlík, E., Böhm, S., Vaňura, P.: Interaction of the cesium cation with hexaethyl calix[6]arene hexaacetate: extraction and DFT study. J. Mol. Liq. 209, 134–137 (2015)

    Article  CAS  Google Scholar 

  30. Pedersen, C.J.: Cyclic polyethers and their complexes with metal salts. J. Am. Chem. Soc. 89, 2495–2496 (1967)

    Article  CAS  Google Scholar 

  31. Pedersen, C.J.: Cyclic polyethers and their complexes with metal salts. J. Am. Chem. Soc. 89, 7017–7036 (1967)

    Article  CAS  Google Scholar 

  32. Hofmanová, A., Koryta, J., Březina, M., Ryan, T.H., Angelis, K.: Electrochemical reduction of monovalent cation complexes of macrocyclic ionophores. Inorg. Chim. Acta 37, 135–140 (1979)

    Article  Google Scholar 

  33. Ehala, S., Kašička, V., Makrlík, E.: Determination of stability constants of valinomycin complexes with ammonium and alkali metal ions by capillary affinity electrophoresis. Electrophoresis 29, 652–657 (2008)

    Article  CAS  PubMed  Google Scholar 

  34. Kolthoff, I.M.: Application of macrocyclic compounds in chemical analysis. Anal. Chem. 51, 1R–22R (1979)

    Article  CAS  Google Scholar 

  35. Hay, B.P., Hancock, R.D.: The role of donor group orientation as a factor in metal ion recognition by ligands. Coord. Chem. Rev. 212, 61–78 (2001)

    Article  CAS  Google Scholar 

Download references

Acknowledgements

This work was supported by the Grant Agency of Faculty of Environmental Sciences, Czech University of Life Sciences, Prague, Project No. 42900/1312/3114 entitled “Environmental Aspects of Sustainable Development of Society”, and by the Czech Ministry of Education, Youth, and Sports (Project MSMT No.: 20/2015).

Author information

Authors and Affiliations

  1. Faculty of Environmental Sciences, Czech University of Life Sciences, Kamýcká 129, 165 21, Prague 6, Suchdol, Czech Republic

    Emanuel Makrlík

  2. Department of Analytical Chemistry, University of Chemistry and Technology, Technická 5, 166 28, Prague 6, Czech Republic

    Petr Vaňura

  3. Laboratoire de Chimie Analytique et Sciences Séparatives, Institut Pluridisciplinaire, Hubert Curien, UMR 7178 IPHC–DSA, ECPM, 25 Rue Becquerel, 67087, Strasbourg Cedex, France

    Zouhair Asfari

Authors
  1. Emanuel Makrlík
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Petr Vaňura
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Zouhair Asfari
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Emanuel Makrlík.

Additional information

Publisher's Note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Makrlík, E., Vaňura, P. & Asfari, Z. Solvent Extraction of Some Univalent Cations into Nitrobenzene by Using Cesium Dicarbollylcobaltate and Four Bis(crown-6) Ether Derivatives of Calix[4]arene. J Solution Chem 48, 445–454 (2019). https://doi.org/10.1007/s10953-019-00858-2

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10953-019-00858-2

Keywords

Search

Navigation