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Catalytic synthesis of aziridine from 1,2-diaminoethane

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The contact conversion of 1,2-diaminoethane over a tungsten trioxide catalyst at 240–580°C has been studied by an impulse chromatographic method. The basic reaction path under these conditions is unimolecular deaminocyclization to give aziridine (31–35%). Piperazine and triethylenediamine, products of bi- and trimolecular deaminocyclization, are present as products. The deamination process is accompanied by coupled dehydrogenation and hydrogenolysis reactions. Addition of the acid anhydrides SiO2, P2O5 and B2O3 to the catalyst increases its activity but has only a negligible affect on the activation energy of the process.

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References

  1. P. A. Gembitskii, D. S. Zhuk, and V. A. Kargin. Chemistry of Ethyleneimine [in Russian], Nauka, Moscow, (1966).

    Google Scholar 

  2. M. Polievka and M. Pavlovic, Petrochemia, 10, No. 6, 207 (1970).

    Google Scholar 

  3. USSR Pat. 230 166, M. K. Sile, A. A. Avots, M. V. Shimanskaya, I. I. Ioffe, and G. S. Idlis, Byull. Izobret., No. 34, 31 (1968).

    Google Scholar 

  4. M. K. Sile, A. A. Avots, M. V. Shimanskaya, and I. I. Ioffe, Izv. Akad. Nauk LatvSSR, Ser. Khim., No. 4, 501 (1971).

    Google Scholar 

  5. M. K. Sile, A. A. Avots, M. V. Shimanskaya, and I. I. Ioffe, Izv. Akad. Nauk LatvSSR, Ser. Khim., No. 1, 54 (1972).

    Google Scholar 

  6. M. K. Sile, A. A. Avots, M. V. Shimanskaya, and I. I. Ioffe, Izv. Akad. Nauk LatvSSR, Ser. Khim., No. 2, 218 (1972).

    Google Scholar 

  7. Jap. Pat. 6 330 394, Yu. Ito, Yo. Takahashi, and R. Uejima; Chem. Abs., 111, 7209 (1989).

    Google Scholar 

  8. Jap. Pat. 7 510 593, T. Agawa, Yo. Ohki, and K. Hotta; Chem. Abs., 83, 163983 (1975).

    Google Scholar 

  9. US Pat. 4 289 656, W. W. Hayes and D. L. Childress; Chem. Abs., 96, 19944 (1982).

    Google Scholar 

  10. US Pat 4 301 036, D. L. Childress and W. W. Hayes; Chem. Abs., 96, 52166 (1982).

    Google Scholar 

  11. US Pat. 4 337 175, E. G. Ramirez; Chem. Abs., 97, 72237h (1982).

    Google Scholar 

  12. US Pat. 4 477 591, E. G. Ramirez; Chem. Abs., 101, 230343 (1984).

    Google Scholar 

  13. Eur. Pat. 227 461, Yo. Hino, Yu. Shimasaki and M. Ueshima; Chem. Abs., 108, 94390 (1988).

    Google Scholar 

  14. Eur. Pat. 228 898, Yo. Hino, Yu. Shimasaki, M. Ueshima, H. Tuneki and H. Yano; Chem. Abs., 107, 200904 (1987).

    Google Scholar 

  15. Eur. Pat. 230 776, Yu. Shimasaki, M. Ueshima, H. Tuneki and K. Ariyoshi; Chem. Abs., 107, 178633 (1987).

    Google Scholar 

  16. Jap. Pat. 6 323 744, Yu. Shimasaki and R. Uejima; Chem. Abs., 109, 39742.

  17. PCT Pat. 8 807 038 Int. Appl. WO, Yu. Morimoto, Yu. Shimasaki, H. Tsuneki, K. Yamamoto, T. Kamei and M. Ueshima; Chem. Abs., 110, 137486 (1989).

    Google Scholar 

  18. Jap Pat. 0 196 167, H. Tsuneki, T. Kamei, Yu. Morimoto and R. Uejima; Chem. Abs., 111, 153599 (1989).

    Google Scholar 

  19. US Pat. 4 833 248, Yu. Shimasaki, H. Tuneki, Yo. Hino, H. Yano and M. Ueshima; Ref. Zhur. Khim., 12N253P (1990).

  20. US Pat. 4 841 061, Yu. Shimasaki, M. Ueshima, H. Tuneki and K. Ariyoshi: Chem. Abs., 112, 35665 (1990).

    Google Scholar 

  21. Jap. Pat. 0 115 7952, H. Tsuneki, H. Yano and R. Uejima; Chem. Abs., 112, 55575 (1990).

    Google Scholar 

  22. PCT Pat. 8 906 229 Int. Appl. WO, K. D. Olson, and S. W. Kaiser; Chem. Abs., 112, 9011 (1990).

    Google Scholar 

  23. PCT Pat. 8 905 797 Int. Appl. WO, K. D. Olson, and S. W. Kaiser; Chem. Abs., 112, 9005 (1990).

    Google Scholar 

  24. M. Ueshima, Yu. Shimasaki, Yo. Hino and H. Tsuneki. Acid-Base Catalysis. Proc. Inst. Symp. 1988, K. Tanabe (ed.), Kodansha, Tokyo (1989), p. 41.

    Google Scholar 

  25. M. Ueshima and Yu. Shimasaki, Kagaku to Kogyo, 43, No. 3, 349 (1990).

    Google Scholar 

  26. Eur. Pat. 370 795, Yu. Shimasaki, H. Tsuneki, Yo. Hino and M. Ueshima; Chem. Abs., 113, 152233 (1990).

    Google Scholar 

  27. Jap. Pat. 0 275 349, K. Ariyoshi, Yo. Hino, H. Tsuneki and R. Uejima; Chem. Abs., 113, 78145 (1990).

    Google Scholar 

  28. US Pat. 4 966 980, T. Kamei, Yu. Shimasaki, H. Tsuneki, K. Yamamoto, Yu. Morimoto and M. Ueshima; Ref. Zhur. Khim., 10N138P (1992).

  29. A. A. Anderson, S. P. Yurel' and M. V. Shimanskaya. Heterogeneous Catalysis in the Preparation and Conversion of Heterocyclic Compounds [in Russian], Zinatne, Riga (1971), p. 175.

    Google Scholar 

  30. S. P. Yurel', A. A. Anderson and M. V. Shimanskaya, Izv. Akad. Nauk LatvSSR, Ser. Khim., No. 6, 729 (1974).

    Google Scholar 

  31. Ya. F. Oshis, A. A. Anderson and M. V. Shimanskaya, Izv. Akad. Nauk LatvSSR, Ser. Khim., No. 6, 675 (1984).

    Google Scholar 

  32. A. A. Anderson, S. P. Yurel' and M. V. Shimanskaya, Izv. Akad. Nauk LatvSSR, Ser. Khim., No. 6, 683 (1968).

    Google Scholar 

  33. V. V. Yushchenko and T. V. Antipina, Zh. Fiz. Khim., 43, 540 (1969).

    Google Scholar 

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1324–1332, October, 1993.

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Anderson, A.A., Simonyan, S.P. & Shimanskaya, M.V. Catalytic synthesis of aziridine from 1,2-diaminoethane. Chem Heterocycl Compd 29, 1134–1141 (1993). https://doi.org/10.1007/BF00538056

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  • DOI: https://doi.org/10.1007/BF00538056

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