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α- and β-diphenylphosphorylated secondary alkanols: I. general method of synthesis and extraction properties towards f-elements

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Abstract

A simple and effective general method of synthesis of α- and β-diphenylphosphorylated secondary alkanols by the reduction of the corresponding phosphorylalkanones with NaBH4 was developed. The extraction properties of the resulting phosphorylalkanols Ph2P(O)(CR2)nCH2CH(OH)Me (n = 0, 1; R = H, Me) were studied in the recovery of f-elements (LaIII, NdIII, HoIII, YbIII, UVI, ThIV) from nitric acid solutions into chloroform and compared with those of both related phosphorylketones and known extractants (n-BuO)3PO, (n-C8H17)3PO, and Ph2P(O)CH2C(O)N(n-Bu)2.

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References

  1. A Book on Ion Exchange, Adsorption and Solvent Extraction (Chemistry Research and Applications), Naushad, M. and Al Othman, Z.A., Eds., New York: Nova Science, 2013.

  2. Kislik, V.S., Solvent Extraction: Classical and Novel Approaches, Oxford: Elsevier, 2012.

    Google Scholar 

  3. Solvent Extraction Principles and Practice, Rydberg, J., Cox, M., Musikas, C., and Choppin, G.R., Eds., Boca Raton: CRC, 2004.

  4. Ion Exchange and Solvent Extraction: A Series of Advances, Moyer, B.A., Ed., Boca Raton: CRC, 2010, vol.19.

  5. Mastryukova, T.A., Artyushin, O.I., Odinets, I.L., and Tananaev, I.G., Mendeleev Chem. J., 2005, vol. 49, no. 2, p.86.

    CAS  Google Scholar 

  6. Rozen, A.M. and Krupnov, B.V., Russ. Chem. Rev., 1996, vol. 65, no. 11, p. 973. DOI: 10.1070/RC1996v065n11ABEH000241.

    Article  Google Scholar 

  7. Sharova, E.V., Artyushin, O.I., and Odinets, I.L., Russ. Chem. Rev., 2014, vol. 83, no. 1, p. 95. DOI: 10.1070/RC2014v083n02ABEH004384.

    Article  Google Scholar 

  8. Safiulina, A.M., Matveeva, A.G., Dvoryanchikova, T.K., Sinegribova, O.A., Tu, A.M., Tatarinov, D.A., Kostin, A.A., Mironov, V.F., and Tananaev, I.G., Russ. Chem. Bull., 2012, vol. 61, no. 2, p. 392. DOI: 10.1007/s11172-012-0055-0.

    Article  CAS  Google Scholar 

  9. Matveeva, A.G., Tu, A.M., Safiulina, A.M., Bodrin, G.V., Goryunov, E.I., Goryunova, I.B., Sinegribova, O.A., and Nifant’ev, E.E., Russ. Chem. Bull., 2013, vol. 62, no. 6, p. 1309. DOI: 10.1007/s11172-013-0184-0.

    Article  CAS  Google Scholar 

  10. Matveeva, A.G., Goryunov, E.I., Tu, A.M., Safiulina, A.M., Goryunova, I.B., Bodrin, G.V., Lesiv, A.V., Sinegribova, O.A., and Brel, V.K., Russ. Chem. Bull., 2014, vol. 63, no. 11, p. 2493. DOI: 10.1007/s11172-014-0767-4.

    Article  CAS  Google Scholar 

  11. Elisratova, Yu.G., Mustafina, A.R., Tatarinov, D.A., Mironov, V.F., Burilov, V.A., Tananaev, I.G., and Konovalov, A.I., Russ. Chem. Bull., 2011, vol. 60, no. 5, p. 790. DOI: 10.1007/s11172-011-0126-7.

    Article  Google Scholar 

  12. Safiulina, A.M., Matveeva, A.G., Lizunov, A.V., Bodrin, G.V., Goryunov, E.I., Grigor’ev, M.S., Semenov, A.A., Brel, V.K., and Nifant’ev, E.E., Doklady Chem., 2015, vol. 460, part 2, p. 57. DOI: 10.7868/S0869565215060146.

    Article  CAS  Google Scholar 

  13. Safiulina, A.M., Matveeva, A.G., Evtushenko, A.V., Lizunov, A.V., Goryunov, E.I., Goryunova, I.B., Bodrin, G.V., Semenov, A.A., and Brel, V.K., Russ. J. Gen. Chem., 2015, vol. 85, no. 9, p. 2128. DOI: 10.1134/S1070363215090170.

    Article  CAS  Google Scholar 

  14. Timofeeva, G.I., Matveeva, A.G., Safiulina, A.M., Ivanets, D.V., Kudryavtsev, E.M., Baulin, V.E., and Tsivadze, A.Yu., Russ. Chem. Bull., 2015, vol. 64, no. 1, p. 224. DOI: 10.1007/s11172-015-0847-0.

    Article  CAS  Google Scholar 

  15. Nash, K.L., Barrans, R.E., Chiarizia, R., Dietz, M.L., Jensen, M.P., Rickert, P.G., Moyer, B.A., Bonnesen, P.V., Bryan, J.C., and Sachleben, R.A., Solvent Extr. Ion Exch., 2000, vol. 18, no. 4, p. 605. DOI: 10.1080/07366290008934700.

    Article  CAS  Google Scholar 

  16. Barrans, R.E., McAlister, D.R., Jr., Herlinger, A.W., and Ferraro, J.R., Solvent Extr. Ion Exch., 1999, vol. 17, no. 5, p. 1195. DOI: 10.1080/07366299908934643.

    Article  CAS  Google Scholar 

  17. Chiarizia, R., Barrans, R.E., Ferraro, J.R., Jr., Herlinger, A.W., and McAlister, D.R., Sep. Sci. Technol., 2001, vol. 36, nos. 5–6, p. 687. DOI: 10.1081/SS-100103615.

    Article  CAS  Google Scholar 

  18. Chiarizia, R., McAlister, D.R., and Herlinger, A.W., Sep. Sci. Technol., 2005, vol. 40, p. 69. DOI: 10.1081/SS-200041762.

    Article  CAS  Google Scholar 

  19. Gannaz, B., Antonio, M.R., Chiarizia, R., Hill, C., and Cote, G., Dalton Trans., 2006, no. 38, p. 4553. DOI: 10.1039/b609492a.

    Article  Google Scholar 

  20. Goryunov, E.I., Bodrin, G.V., Goryunova, I.B., Nelyubina, Yu.V., Petrovskii, P.V., Strelkova, T.V., Peregudov, A.S., Matveeva, A.G., Pasechnik, M.P., Matveev, S.V., and Nifant’ev, E.E., Russ. Chem. Bull., 2013, vol. 62, no. 3, p. 780. DOI: 10.1007/s11172-013-0106-1.

    Article  CAS  Google Scholar 

  21. Keough, P.T. and Grayson, M., J. Org. Chem., 1962, vol. 27, no. 5, p. 1817. DOI: 10.1021/jo01052a082.

    Article  CAS  Google Scholar 

  22. Issleib, K. and Roloff, H.-R., J. Prakt. Chem., 1970, vol. 312, no. 4, p. 578. DOI: 10.1002/prac.19703120406.

    Article  CAS  Google Scholar 

  23. Gonzalez-Nogal, A.M., Cuadrado, P., and Sarmentero, M.A., Eur. J. Org. Chem., 2009, no. 6, p. 850. DOI: 10.1002/ejoc.200800984.

    Article  Google Scholar 

  24. Rey, P., Taillades, J., Rossi, J.C., and Gros, G., Tetrahedron Lett., 2003, vol. 44, no. 32, p. 6169. DOI: 10.1016/S0040-4039(03)01467-9.

    Article  CAS  Google Scholar 

  25. Conant, J.B., Braverman, J.B.S., and Hussey, R.E., J. Am. Chem. Soc., 1923, vol. 45, no. 1, p. 165. DOI: 10.1021/ja01654a024.12.

    Article  CAS  Google Scholar 

  26. Bell, A., Davidson, A.H., Earnshaw, C., Norrish, H.K., Torr, R.S., Trowbridge, D.B., and Warren, S., J. Chem. Soc., Perkin Trans. 1, 1983, no. 12, p. 2879. DOI: 10.1039/P19830002879.

    Article  Google Scholar 

  27. Mikolajczyk, M. and Zatorski, A., J. Org. Chem., 1991, vol. 56, no. 3, p. 1217. DOI: 10.1021/jo00003a051.

    Article  CAS  Google Scholar 

  28. Arnold, P., US Patent 2009/0198038 A1.

  29. Zhou, L., Bao, M., and He, R., Fenzi Kexue Xuebao, 2009, vol. 25, p.19.

    CAS  Google Scholar 

  30. Safiulina, A.M., Matveeva, A.G., Ivanets, D.V., Kudryavtsev, E.M., Grigor’ev, M.S., Baulin, V.E., and Tsivadze A.Yu., Russ. Chem. Bull., 2015, vol. 64, no. 1, p. 161. DOI: 10.1007/s11172-015-0837-2.

    Article  CAS  Google Scholar 

  31. Safiulina, A.M., Matveeva, A.G., Ivanets, D.V., Kudryavtsev, E.M., Baulin, V.E., and Tsivadze, A.Yu., Russ. Chem. Bull., 2015, vol. 64, no. 1, p. 169. DOI: 10.1007/s11172-015-0838-1.

    Article  CAS  Google Scholar 

  32. Medved’, T.Ya., Polikarpov, Yu.M., Yudina, K.S., and Kabachnik, M.I., Izv. Akad. Nauk SSSR, Ser. Khim., 1965, no. 9, p. 1707.

    Google Scholar 

  33. Weissberger, A., Proskauer, E.S., Riddick, J.A., and Toops, E.E., Organic Solvents: Physical Properties and Methods of Purification, New York: Interscience, 1955, 2 ed.

    Google Scholar 

  34. Sharova, E.V., Artyushin, O.I., Shaplov, A.S., Myasoedova, G.V., and Odinets, I.L., Tetrahedron Lett., 2008, vol. 49, no. 10, p. 1641. DOI: 10.1016/j.tetlet.2008.01.007.

    Article  CAS  Google Scholar 

  35. Lemport, P.S., Bodrin, G.V., Pasechnik, M.P., Matveeva, A.G., Petrovskii, P.V., Vologzhanina, A.V., and Nifant’ev, E.E., Russ. Chem. Bull., 2007, vol. 56, no. 9, p. 1911. DOI: 10.1007/s11172-007-0293-8.

    Article  CAS  Google Scholar 

  36. Wallace, P. and Warren, S., J. Chem. Soc., Perkin Trans. 1, 1988, no. 11, p. 2971. DOI: 10.1039/P19880002971.

    Article  Google Scholar 

  37. Savin, S.B., Arsenazo III, Moscow: Atomizdat, 1966.

    Google Scholar 

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Authors and Affiliations

  1. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, ul. Vavilova 28, Moscow, 119991, Russia

    E. I. Goryunov, A. G. Matveeva, I. B. Goryunova, G. V. Bodrin & V. K. Brel

  2. Uralchem United Chemical Company, Open Joint-Stock Company, Presnenskaya nab. 6/2, Moscow, 123317, Russia

    A. M. Safiulina

Authors
  1. E. I. Goryunov
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  2. A. G. Matveeva
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  3. A. M. Safiulina
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  4. I. B. Goryunova
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  6. V. K. Brel
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Correspondence to E. I. Goryunov.

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Original Russian Text © E.I. Goryunov, A.G. Matveeva, A.M. Safiulina, I.B. Goryunova, G.V. Bodrin, V.K. Brel, 2016, published in Zhurnal Obshchei Khimii, 2016, Vol. 86, No. 3, pp. 489–498.

To the 100th Anniversary of A.N. Pudovik

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Goryunov, E.I., Matveeva, A.G., Safiulina, A.M. et al. α- and β-diphenylphosphorylated secondary alkanols: I. general method of synthesis and extraction properties towards f-elements. Russ J Gen Chem 86, 629–638 (2016). https://doi.org/10.1134/S1070363216030208

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  • DOI: https://doi.org/10.1134/S1070363216030208

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