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Russian Chemical Bulletin

, Volume 55, Issue 8, pp 1440–1447 | Cite as

Mono and bis[N-aryl(benzyl)]amides of phosphorylacetic acids. One-pot synthesis and extraction of actinides from nitric acid solutions

  • O. I. Artyushin
  • E. V. Sharova
  • I. L. Odinets
  • K. A. Lyssenko
  • D. G. Golovanov
  • T. A. Mastryukova
  • G. A. Pribylova
  • I. G. Tananaev
  • G. V. Myasoedova
Article

Abstract

A one-pot synthetic route to phosphorylacetic acid N-aryl(alkylaryl)amides, including those containing two phosphorylmethylcarbamoyl moieties attached to the arene framework, has been developed. The method is based on reactions of amines with the corresponding acid chlorides generated in situ with the use of phosphorus trichloride as a mild chlorinating agent. The compositions and structures of the compounds obtained and their extraction ability toward AmIII were determined. Suggestions were made about the compositions of the extracted complexes with phosphorylacetic acid N-aryl(alkylaryl)amides.

Key words

aromatic amines phenylenediamines xylylenediamines phosphorylacetic acids phosphorylacetic acid amides carbamoylmethylphosphine oxides actinides, americium extraction 

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References

  1. 1.
    T. Ya. Medved’, M. K. Chmutova, N. P. Nesterova, O. E. Koiro, N. E. Kochetkova, B. F. Myasoedov, and M. I. Kabachnik, Izv. Akad. Nauk SSSR, Ser. Khim., 1981, 2121 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1981, 30 (Engl. Transl.)].Google Scholar
  2. 2.
    E. P. Horwitz, D. G. Kalina, H. Diamond, D. G. Vandergrift, and W. W. Schultz, Solvent Extr. Ion. Exch., 1985, 3, 75.Google Scholar
  3. 3.
    E. P. Horwitz and W. W. Schulz, in Metal Ion Separation and Preconcentration: Progress and Opportunities, Eds A. H. Bond, M. L. Dietz, and R. D. Rogers, Am. Nucl. Soc., Oxford University Press, Oxford, USA, 1998, Ch. 20.Google Scholar
  4. 4.
    V. N. Romanovskiy, I. V. Smirnov, A. Y. Shadrin, and B. F. Myasoedov, Spectrum’98, Proc. Int. Topic. Meet. Nuclear and Hazardous Waste Management (La Grange Park, Illinois), Am. Nucl. Soc., La Grange Park, Illinois, 1998, 576.Google Scholar
  5. 5.
    F. Arnaud-Neu, V. Bëhmer, J.-F. Dozol, C. Grüttner, R. A. Jakobi, D. Kraft, O. Mauprivez, H. Rouquette, M.-J. Schwing-Weill, N. Simon, and W. Vogt, J. Chem. Soc., Perkin Trans. 2, 1996, 1175.Google Scholar
  6. 6.
    M. W. Peters, E. J. Werner, and M. J. Scott, Inorg. Chem., 2002, 41, 1707.CrossRefGoogle Scholar
  7. 7.
    R. Bernard, D. Cornu, B. Grüner, J.-F. Dozol, P. Miele, and B. Bonnetot, J. Organometal. Chem., 2002, 657, 83.CrossRefGoogle Scholar
  8. 8.
    O. I. Artyushin, E. V. Sharova, I. L. Odinets, S. V. Lenevich, V. P. Morgalyuk, I. G. Tananaev, G. V. Pribylova, G. V. Myasoedova, T. A. Mastryukova, and B. F. Myasoedov, Izv. Akad. Nauk, Ser. Khim., 2004, 2395 [Russ. Chem. Bul., Int. Ed., 2004, 53, 2499].Google Scholar
  9. 9.
    V. P. Morgalyuk, G. A. Pribylova, D. E. Drozhko, L. A. Ivanova, R. M. Kalyanova, O. I. Artyushin, M. V. Logunov, I. G. Tananaev, T. A. Mastryukova, and B. F. Myasoedov, Radiokhimiya, 2004, 46, 128 [Radiochemistry, 2004, 46 (Engl. Transl.)].Google Scholar
  10. 10.
    L. F. Tietze and T. Eicher, Reactionen und Synthesen im Organisch-Chemischen Praktikum und Forschungslaboratorium, Georg Thieme Verlag, Stuttgart-New York, 1991 (and references therein).CrossRefGoogle Scholar
  11. 11.
    I. L. Odinets, P. V. Kazakov, R. U. Amanov, M. Yu. Antipin, L. V. Kovalenko, and T. A. Mastryukova, Izv. Akad. Nauk, Ser. Khim., 1992, 1879 [Bull. Russ. Acad. Sci., Div. Chem. Sci., 1992, 41, 1466 (Engl. Transl.)].Google Scholar
  12. 12.
    J.-F. Devaux, S. V. O’Neil, N. Guillo, and L. A. Paquette, Collect. Czech. Chem. Commun., 2000, 65, 490.CrossRefGoogle Scholar
  13. 13.
    P. Coutrot and A. Ghribi, Synthesis, 1986, 661.Google Scholar
  14. 14.
    Y. M. Kulyako, D. A. Malikov, M. K. Chmutova, M. N. Litvina, and B. F. Myasoedov, J. All. Comp., 1998, 760.Google Scholar
  15. 15.
    A. M. Rozen, A. S. Nikiforov, Z. I. Nikolotova, and N. A. Kartashova, Atomnaya energiya [Atomic Energy], 1985, 59, 413 (in Russian); A. M. Rozen, V. I. Volk, A. Yu. Vakhrushin, B. S. Zakharkin, N. A. Kartasheva, B. V. Krupnov, and Z. I. Nikolotova, Radiokhimiya, 1999, 41, 205 [Radiochem., 1999, 41 (Engl. Transl.)].Google Scholar
  16. 16.
    A. M Rozen and B. V. Krupnov, Usp. Khim., 1996, 65, 1052 [Russ. Chem. Rev., 1996, 65 (Engl. Transl.)].Google Scholar
  17. 17.
    E. N. Tsvetkov, R. A. Malevannaya, and M. I. Kabachnik, Zh. Obshch. Khim., 1967, 37, 695 [J. Gen. Chem. USSR, 1967, 37 (Engl. Transl.)].Google Scholar
  18. 18.
    J. Michalski and S. Musierowicz, Angew. Chem., 1967, 79, 1070.Google Scholar
  19. 19.
    G. M. Sheldrick, SHELXTL, Version 5, Software Reference Manual, Siemens Industrial Automation, Madison, WI, 1994.Google Scholar

Copyright information

© Springer Science+Business Media, Inc. 2006

Authors and Affiliations

  • O. I. Artyushin
    • 1
  • E. V. Sharova
    • 1
  • I. L. Odinets
    • 1
  • K. A. Lyssenko
    • 1
  • D. G. Golovanov
    • 1
  • T. A. Mastryukova
    • 1
  • G. A. Pribylova
    • 2
  • I. G. Tananaev
    • 2
  • G. V. Myasoedova
    • 2
  1. 1.A. N. Nesmeyanov Institute of Organoelement CompoundsRussian Academy of SciencesMoscowRussian Federation
  2. 2.V. I. Vernadsky Institute of Geochemistry and Analytical ChemistryRussian Academy of SciencesMoscowRussian Federation

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