Skip to main content
Log in

Extraction of monocarboxylic acids with binary extracting agents based on amines and quaternary ammonium bases

  • Organic Technology
  • Published:
Theoretical Foundations of Chemical Engineering Aims and scope Submit manuscript

Abstract

The distribution of monocarboxylic acids is reported for extraction systems with binary extracting agents, namely, amine and quaternary ammonium base (QAB) salts of organic acids with widely varied acid dissociation constants (pK a 1.5–10). Monocarboxylic acid extractability orders have been obtained for systems with binary extracting agents based on trioctylmethylammonium and trioctylammonium (TOA). The best extractability is shown by acids with long hydrocarbon radicals (butyric and caproic acids). Lactic acid is the least extractable. Extractive power orders have been obtained for QAB- and TOA-based binary extracting agents. For monocarboxylic acid extraction with QAB salts, the extractive power order correlates with the acid dissociation constants of the parent organic acids: trioctylmethylammonium p-tert-butylphenolate ≫ caprylate > dialkylphosphinate > dialkylmonothiophosphinate > dialkylphosphate > dinonylnaphthalene sulfonate > dialkyldithiophosphinate. The extractive power of the QAB-based binary extracting agents is much higher than that of the TOA salts.

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

Access this article

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

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. Playne, M.J., Propionic and Butyric Acids, in Comprehensive Biotechnology, Moo-Young, M., Ed., Oxford: Pergamon, 1985, vol. 3, p. 731.

    Google Scholar 

  2. Kertes, A.S. and King, C.J., Extraction Chemistry of Fermentation Product Carboxylic Acid, Biotechnol. Bioeng., 1986, vol. 28, p. 269.

    Article  CAS  Google Scholar 

  3. Wódzki, R. and Nowaczyk, J., Extraction and Separation of Propionic and Acetic Acid by Permeation in a Hybrid Membrane System Composed of Liquid and Ion-Exchange Polymer, Solvent Extr. Ion Exch., 1997, vol. 15, no. 6, p. 1085.

    Article  Google Scholar 

  4. Zeikus, J.G., Jain, M.K., and Elankovan, P., Biotechnology of Succinic Acid Production and Markets for Derived Industrial Products, Appl. Microbiol. Biotechnol., 1999, vol. 51, p. 545.

    Article  CAS  Google Scholar 

  5. Wasewar, K.L., Heesink, A.B.M., Versteeg, G.F., and Pangarkar, V.G., Intensification of Enzymatic Conversion of Glucose to Lactic Acid by Reactive Extraction, Chem. Eng. Sci., 2003, vol. 58, p. 3385.

    Article  CAS  Google Scholar 

  6. Yang, S.T., White, S.A., and Hsu, S.T., Extraction of Carboxylic Acid with Tertiary and Quaternary Amines: Effect of pH, Ind. Eng. Chem. Res., 1991, vol. 30, no. 6, p. 1335.

    Article  CAS  Google Scholar 

  7. Yankov, D., Molinier, J., and Albert, J., Lactic Acid Extraction from Aqueous Solutions with Tri-n-Octylamine Dissolved in Decanol and Dodecane, Biochem. Eng. J., 2004, vol. 21, p. 63.

    Article  CAS  Google Scholar 

  8. Kyuchoukov, G., Yankov, D., Albet, J., and Molinier, I., Mechanism of Lactic Acid Extraction with Quaternary Ammonium Chloride (Aliqual 336), Ind. Eng. Chem. Res., 2005, vol. 44, p. 5733.

    Article  CAS  Google Scholar 

  9. Matsumoto, M., Otono, Ò., and Kondo, K., Synergistic Extraction of Organic Acids with Tri-n-Octylamine and Tri-N-Butylphosphate, Sep. Purif. Technol., 2001, vol. 24, p. 337.

    Article  CAS  Google Scholar 

  10. Kyuchoukov, G., Marinova, M., and Albet, J., Extraction of Lactic Acid by Means of a Mixed Extractant, Ind. Eng. Chem. Res., 2001, vol. 40, p. 5635.

    Article  CAS  Google Scholar 

  11. Khol’kin, A.I. and Kuz’min, V.I., Binary Extraction, Zh. Neorg. Khim., 1982, vol. 27, no. 8, p. 2070.

    Google Scholar 

  12. Khol’kin, A.I., Kuz’min, V.I., and Protasova, N.V., Binary Exraction of Acids, Zh. Neorg. Khim., 1986, vol. 31, no. 5, p. 1245.

    Google Scholar 

  13. Sizova, N.L., Eal’, A., and Vitner, A., Exraction of Carbolic Acids by Binary Extractants, in Khimiya i tekhnologiya ekstraktsii (Extraction Chemistry and Technology), Moscow: Ross. Khim.-Tekhnol. Univ. im. D. I. Mendeleeva, 2001, p. 331.

    Google Scholar 

  14. Khol’kin, A.I., Binary Exraction. Part II: Extraction of Acids and Metal Hydroxides, Khim. Tekhnol., 2000, no. 6, p. 37.

  15. Syzova, N., Eyal, A.M., Vitner, A., and Hazan, B., Interactions between the Components of ABC Extractants and Extraction of Monoearboxylic Acids by These Extraclants, Solvent Extr. Ion Exch., 2004, vol. 22, no. 1, p. 31.

    Article  CAS  Google Scholar 

  16. Belova, V.V., Kulichenkov, S.A., Voshkin, A.A., Khol’kin, A.I., Kuvaeva, Z.I., and Soldatov, V.S., Extraction of Mineral Acids with Methyltrioctylammonium Dinonylnaphthalenesulfonate, Russ. J. Inorg. Chem., 2007, vol. 52, no. 3, p. 460.

    Article  Google Scholar 

  17. Belova, V.V., Zhidkova, T.I., Zakharov, N.A., and Khol’kin, A.I., Synthesis of Tetraalkylammonium Salts of Organic Acids and Study of Their Physicochemical Properties, in Sovremennye problemy khimii i tekhnologii ekstraktsii (Current Topics in Extraction Chemistry and Technology), Moscow, 1999, vol. 2, p. 20.

    Google Scholar 

  18. Kratkii spravochnik khimika (Chemist’s Concise Handbook), Nekrasov, B.V., Ed., Moscow: Goskhimizdat, 1954.

    Google Scholar 

  19. Syzova, N., Eyal, A.M., Vitner, A., and Hazan, B., Extraction of Carboxylic Acids by ABC Extractants: Effects of Temperature, the Polarity of the Diluent, and the Ratio between Extractant Components, Solvent Extr. Ion Exch., 2004, vol. 22, no. 1, p. 69.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to V. V. Belova.

Additional information

Original Russian Text © Yu.A. Zakhodyaeva, A.A. Voshkin, V.V. Belova, A.I. Khol’kin, 2010, published in Khimicheskaya Tekhnologiya, 2010, Vol. 11, No. 7, pp. 407–412.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Zakhodyaeva, Y.A., Voshkin, A.A., Belova, V.V. et al. Extraction of monocarboxylic acids with binary extracting agents based on amines and quaternary ammonium bases. Theor Found Chem Eng 45, 739–743 (2011). https://doi.org/10.1134/S0040579511050186

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S0040579511050186

Keywords

Navigation