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Cascade synthesis of polyorganosiloxanes in an organodichlorosilane—acetone—carbamide non-aqueous system

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Abstract

Нydrolytic polycondensation of organochlorosilanes (OCS) RR´SiCl2, where R,R´= Me, Et, C2H3, and H, in an acetone—carbamide non-aqueous system was studied. It was found by GLC, GPC, 29Si NMR spectroscopy, mass spectrometry, and elemental analysis that linear and cyclic oligoorganosiloxanes were formed in a quantitative yield as a result of hydrolysis. The mechanism of the process includes conjugate mutually dependent reactions: (i) generation of water via dehydrocondensation of acetone and carbamide involving HCl and (ii) hydrolysis of OCS to form HCl. This determines the cascade character of the overall process. The hydrolysis of OCS in the system studied develops with autoacceleration like branched cascade processes because of peculiarities of stoichiometry of the dehydrocondensation of acetone and carbamide.

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References

  1. E. A. Chernyshev, V. N. Talanov, Khimiya elementoorganicheskikh monomerov i polimerov [Chemistry of Organoelement Monomers and Polymers], KolosS, Moscow, 2011, 440 pp. (in Russian).

    Google Scholar 

  2. Silicon Containing Polymers. The Science and Technology of Their Synthesis and Applicattons, Springer Verlag, 2013, 792 pp.

  3. M. Butts, J. Cella, C. Wood, G. Gilette, in Encyclopedia of Polymer Science and Technology, 3rd ed., Eds H. F. Mark, J. I. Kroschwitz, Wiley-Intersci. Publ., Hoboken, 2004, Vol. 11, p. 765.

    Google Scholar 

  4. L. M. Khananashvili, Khimiya i tekhnologiya elementoorganicheskikh monomerov i polimerov [Chemistry and Technology of Organoelement Monomers and Polymers], Khimiya, Moscow, 1998, 528 pp. (in Russian).

    Google Scholar 

  5. P. V. Ivanov, Doct. Sci. (Chem.) Thesis, Author´s Abstract, Moscow, 1998, 48 pp. (in Russian).

    Google Scholar 

  6. P. V. Ivanov, O. V. Mlackovskaya, E. A. Chernyshev, L. V. Kostikova, A. S. Mozzhukhin, N. M. Busyreva, Russ. Chem. Bull. (Int. Ed.), 1997, 46, 719 [Izv. Akad. Nauk, Ser. Khim., 1997, 750].

    Article  CAS  Google Scholar 

  7. P. V. Ivanov, Vysokomol. Soedin., Ser. A, 1995, 37, 417 [Polym. Sci., Ser. A (Engl. Transl.), 1995, 37].

    CAS  Google Scholar 

  8. E. A. Chernyshev, P. V. Ivanov, D. N. Golubykh, Russ. Chem. Bull. (Int. Ed.), 2001, 50, 1998 [Izv. Akad. Nauk, Ser. Khim., 2001, 1909].

    Article  CAS  Google Scholar 

  9. P. V. Ivanov, Vestn. MITKhT [Bulletin of Moscow Institute of Fine Chemical Technology], 2011, 6, 3 (in Russian).

    CAS  Google Scholar 

  10. V. V. Zuev, A. V. Kalinin, Phosphorus, Sulfur Silicon, 2003, 178, 1280.

    Google Scholar 

  11. V. S. Fikhtengol´ts, A. L. Klebanskii, K. A. Rzhendzinskaya, Zh. Org. Khim., 1957, 27, 2984 [J. Org. Chem. USSR (Engl. Transl.), 1957, 27].

    Google Scholar 

  12. S. V. Basenko, M. G. Voronkov, Dokl. Akad. Nauk, 1994, 339, 486 [Dokl. Chem. (Engl. Transl.) 1994, 339].

    CAS  Google Scholar 

  13. N. S. Leznov, L. A. Sabun, K. A. Andrianov, Zh. Org. Khim., 1959, 29, 1518 [J. Org. Chem. USSR (Engl. Transl.), 1959, 29].

    CAS  Google Scholar 

  14. E. V. Egorova, N. G. Vasilenko, N. V. Demchenko, E. A. Tatarinova, A. M. Muzafarov, Dokl. Chem. (Engl. Transl.), 2009, 424, 15 [Dokl. Akad. Nauk, 2009, 424, 200].

    CAS  Google Scholar 

  15. A. A. Bychkova, F. V. Soskov, A. I. Demchenko, P. A. Storozhenko, A. M. Muzafarov, Russ. Chem. Bull. (Int. Ed.), 2011, 60, 2384 [Izv. Akad. Nauk, Ser. Khim., 2011, 2337].

    Article  CAS  Google Scholar 

  16. S. A. Milenin, A. A. Kalinina, N. V. Demchenko, N. G. Vasilenko, A. M. Muzafarov, Russ. Chem. Bull. (Int. Ed.), 2013, 62, 705 [Izv. Akad. Nauk, Ser. Khim., 2013, 705].

    Article  CAS  Google Scholar 

  17. A. G. Ivanov, V. M. Kopylov, V. L. Ivanova, V. A. Kovyazin, I. B. Sokol´skaya, I. I. Khazanov, Russ. J. Gen. Chem. (Engl. Transl.), 2012, 82, 66 [Zh. Obshch. Khim., 2012, 82, 69].

    Article  CAS  Google Scholar 

  18. N. S. Bredov, E. Yu. Shporta, L. Yanqing, V. V. Kireev, R. S. Borisov, M. V. Gorlov, V. F. Posokhova, V. P. Chuev, Polym. Sci., Ser. B (Engl. Transl.), 2013, 55, 472 [Vysokomol. Soedin., Ser. B, 2013, 55, 1122].

    Article  CAS  Google Scholar 

  19. S. V. Basenko, L. V. Klyba, M. G. Voronkov, Russ. J. Gen. Chem. (Engl. Transl.), 2000, 70, 1358 [Zh. Obshch. Khim., 2000, 70, 1459].

    Google Scholar 

  20. M. G. Voronkov, I. P. Tsyrendorzhieva, N. P. Ivanova, E. I. Dubinskaya, Russ. J. Gen. Chem. (Engl. Transl.), 1998, 68, 658 [Zh. Obshch. Khim., 1998, 68, 699].

    CAS  Google Scholar 

  21. M. Ando, M. Ikeno, Chem. Lett., 1980, 1255.

    Google Scholar 

  22. T. Takiguchi, J. Org. Chem., 1958, 23, 1216.

    Article  CAS  Google Scholar 

  23. E. G. Rochow, K. Gingold, J. Am. Chem. Soc., 1954, 76, 4852.

    Article  CAS  Google Scholar 

  24. V. F. Traveń, Organicheskaya khimiya: uchebnik dlya vuzov [Organic Chemistry: Textbook for Higher Educational Institutions], Akademkniga, Moscow, 2008, Vol. 1, 727 pp. (in Russian).

  25. B. G. Zavin, E. S. Trankina, A. M. Muzafarov, Russ. Chem. Bull. (Int. Ed.), 2013, 62, 1459 [Izv. Akad. Nauk, Ser. Khim., 2013, 1459].

    Article  Google Scholar 

  26. H. H. Hatt, A. C. K. Triflatt, Chem. Commun., 1965, 439.

    Google Scholar 

  27. G. Zigeuner, E. Fuchs, H. Sterk, Monatsh. Chem., 1966, 97, 36.

    Article  CAS  Google Scholar 

  28. A. R. Butler, I. Hussain, J. Chem. Soc., Perkin Trans. 2, 1980, 232.

    Google Scholar 

  29. A. Fontana, P. De Mario, G. Siani, M. Perini, S. Cerritelli, R. Ballini, Eur. J. Org. Chem., 2000, 1641.

    Google Scholar 

  30. C. W. Lentz, Inorg. Chem., 1964, 3, 574.

    Article  CAS  Google Scholar 

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Authors and Affiliations

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

    B. G. Zavin, E. S. Trankina, A. A. Kondrashova, N. D. Kagramanov, N. S. Ikonnikov & A. M. Muzafarov

Authors
  1. B. G. Zavin
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  2. E. S. Trankina
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  3. A. A. Kondrashova
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  4. N. D. Kagramanov
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  5. N. S. Ikonnikov
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  6. A. M. Muzafarov
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Correspondence to B. G. Zavin.

Additional information

Dedicated to Academician of the Russian Academy of Sciences V. M. Novotortsev on the occasion of his 70th anniversary.

Based on the materials of the XIII Andrianov Conference "Organosilicon Compounds: Synthesis, Properties, and Application" (to the 110th anniversary of Academician К. А. Andrianov, June 28—July 1, 2015, Moscow).

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 3, pp. 0767—0773, March, 2016.

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Zavin, B.G., Trankina, E.S., Kondrashova, A.A. et al. Cascade synthesis of polyorganosiloxanes in an organodichlorosilane—acetone—carbamide non-aqueous system. Russ Chem Bull 65, 767–773 (2016). https://doi.org/10.1007/s11172-016-1371-6

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  • DOI: https://doi.org/10.1007/s11172-016-1371-6

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