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Derivatization of carboxylic acids with 9-bromomethylacridine using micellar phase-transfer catalysis

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Summary

Micellar phase-transfer catalysis (MPTC) offers the opportunity to derivatize carboxylic acids directly in an aqueous matrix without prior extraction of the acids into a suitable aprotic solvent. The currently developed MPTC system consists of a non-ionic surfactant, Arkopal N-130, an ion-pair agent, tetrakis-(decyl)-ammonium bromide, and a novel fluorescence reagent, 9-bromomethylacridine. The MPTC system can be applied to the derivatization of many types of carboxylic acids. The reaction rate is affected by the lipophilicity of the acid and by the presence of other functional groups. For lipophilic carboxylic acids the reaction is complete within 5 min at 60°C and pH 7.0.

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References

  1. A. Hulshoff, H. Lingeman, inS. G. Schulman (Ed.), Molecular Luminescence Spectroscopy, Methods and Applications, Wiley, New York, p. 621.

  2. F. A. L. van der Horst, M. H. Post, J. J. M. Holthuis, J. Chromatogr.,456, 201 (1988).

    Google Scholar 

  3. F. A. L. van der Horst, J. M. Reijn, M. H. Post, A. Bult, J. J. M. Holthuis, U. A. Th. Brinkman, J. Chromatogr., accepted for publication.

  4. F. A. L. van der Horst, G. G. Eikelboom, J. J. M. Holthuis, J. Chromatogr.,456, 191 (1988).

    Google Scholar 

  5. E. V. Dehmlow, S. S. Dehmlow, Phase-Transfer Catalysis, Verlag Chemie, Weinheim, 1980.

    Google Scholar 

  6. C. M. Starks, C. Liotta, Phase-Transfer Catalysis, Principles and Techniques, Academic Press, New York, 1978.

    Google Scholar 

  7. F. A. L. van der Horst, J. J. M. Holthuis, J. Chromatogr.,426, 267 (1988).

    Google Scholar 

  8. K. Akasaka, T. Suzuki, H. Ohrui, H. Meguro, Y. Shindo, H. Takahash, Anal. Lett.,20, 1581 (1987).

    Google Scholar 

  9. O. Tsuge, M. Nishinohara, M. Tashiro, Bull. Chem. Soc. Japan,36, 1477 (1963).

    Google Scholar 

  10. A. Leo, C. Hansch, D. Elkins, Chem. Rev.,71, 525 (1971).

    Google Scholar 

  11. J. Wisniak, A. Tami, Liquid-Liquid Equilibrium and Extraction. Elsevier, Amsterdam, 1980, Part 1.

    Google Scholar 

  12. J. Wisniak, A. Tamir, Liquid-Liquid Equilibrium and Extraction. Elsevier, Amsterdam, 1985, Supplement 1.

    Google Scholar 

  13. B. L. van Buuren, Chem. Rev.,3, 325 (1963).

    Google Scholar 

  14. N. Mataga, Y. Kaifu, M. Koizumi, Bull. Chem. Soc. Japan,29, 375 (1956).

    Google Scholar 

  15. T. Wolff, J. Colloid Intert. Sci.,83, 658 (1981).

    Google Scholar 

  16. F. A. L. van der Horst, M. H. Post, J. J. M. Holthuis, U. A. Th. Brinkman, J. Chromatogr., accepted for publication.

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van der Horst, F.A.L., Post, M.H., Holthuis, J.J.M. et al. Derivatization of carboxylic acids with 9-bromomethylacridine using micellar phase-transfer catalysis. Chromatographia 28, 267–273 (1989). https://doi.org/10.1007/BF02260773

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  • DOI: https://doi.org/10.1007/BF02260773

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