Skip to main content
SpringerLink
Log in

Catalysts for the Direct Synthesis of Organotin Compounds, Part 1: Reactions between Organohalides and Tin Alloys

  • CATALYSIS IN CHEMICAL AND PETROCHEMICAL INDUSTRY
  • Published:
Catalysis in Industry Aims and scope Submit manuscript

Abstract

This review is the first part of a series of reviews devoted to the direct synthesis of organotin compounds. The conditions for and results from the reaction between tin alloys and organohalides are considered. The efficiency of catalysts and the prospects for using tin alloys in the synthesis of organotin compounds are analyzed, and some possible mechanisms of these processes are discussed.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1.
Fig. 2.
Fig. 3.
Fig. 4.
Fig. 5.
Fig. 6.
Fig. 7.
Fig. 8.
Fig. 9.
Fig. 10.
Fig. 11.
Fig. 12.
Fig. 13.

Similar content being viewed by others

REFERENCES

  1. Van der Kerk, G.J.M., Chem. Ind., 1970, vol. 20, pp. 644–647.

    Google Scholar 

  2. Aylett, B.J., in Organometallic Compounds, vol. 1: The Main Group Elements, London: Chapman & Hall, 1979, pp. 177–377.

  3. Evans, C.J. and Karpel, S.J., J. Organomet. Chem. Libr., 1985, vol. 16, pp. 1–279.

    Google Scholar 

  4. Omae, I., J. Organomet. Chem. Libr., 1989, vol. 21, pp. 1–355.

    Google Scholar 

  5. Finnegan, C., Ryan, D., Enright, A.-M., and Garcia-Cabellos, G., Crit. Rev. Environ. Sci. Technol., 2018, vol. 48, no. 1, pp. 77–118. https://doi.org/10.1080/10643389.2018.1443669

    Article  CAS  Google Scholar 

  6. Shiryaev, V.I. and Storozhenko, P.A., Vse Mater., 2011, no. 10, pp. 23–35.

  7. Shiryaev, V.I. and Storozhenko, P.A., Vse Mater., 2011, no. 11, pp. 42–49.

  8. Shiryaev, V.I. and Storozhenko, P.A., Vse Mater., 2012, no. 1, pp. 34–47.

  9. Luijten, J.G.A., in Organotin Compounds, Sawyer, A.K., Ed., New York: Marcel Dekker, 1972 vol. 3, ch. 12, pp. 931–974.

    Google Scholar 

  10. Shiryaev, V.I., Agrokhimiya, 2010, no. 3, pp. 83–94.

  11. Shiryaev, V.I. and Storozhenko, P.A., Vse Mater., 2011, no. 12, pp. 38–52.

  12. Gitlitz, M.H., in Organotin Compounds: New Chemistry and Application, Zucherman, J.J., Ed., Washington, DC: Amer. Chem. Soc., 1976, pp. 167–176.

    Google Scholar 

  13. Storozhenko, P.A., Veselov, A.V., Grachev, A.A., Kirilina, N.I., and Shiryaev, V.I., Catal. Ind., 2020, vol. 12, no. 4, pp. 292–303. https://doi.org/10.1134/S2070050420040078

    Article  Google Scholar 

  14. Storozhenko, P.A., Magdeev, K.D., Grachev, A.A., Kirilina, N.I., and Shiryaev, V.I., Catal. Ind., 2020, vol. 12, no. 4, pp. 304–315. https://doi.org/10.1134/S207005042004008X

    Article  Google Scholar 

  15. Storozhenko, P.A., Grachev, A.A., Magdeev, K.D., and Shiryaev, V.I., Catal. Ind., 2021, vol. 13, no. 2, pp. 132–142. https://doi.org/10.1134/S2070050421020112

    Article  Google Scholar 

  16. Otera, J., Esterification. Methods, Reactions, and Applications, Weinheim: Wiley-VCH, 2003.

    Google Scholar 

  17. Bailar, J.C.Jr., Catal. Rev., 1974, vol. 10, no. 1, pp. 17–36.

    Article  CAS  Google Scholar 

  18. Otera, J., Biesemans, M., Pinoie, V., Poelmans, K., and Willem, R., in Tin Chemistry: Fundamentals, Frontiers, and Applications, Davies, A.G., Gielen, M., Pannell, K.H., and Tiekink, E.R.T., Eds., New York: Wiley. 2008, ch. 6.1, pp. 667–680.

    Google Scholar 

  19. Omae, I., in Application of Organometallic Compounds, Chichester: Wiley & Sons, 1998, ch. 10, pp. 185–214.

    Google Scholar 

  20. Sawyer, A.K., Organotin Compounds, New York: Marcel Dekker, 1971, vols. 1–3.

    Google Scholar 

  21. Davies, A.G., Organotin Chemistry, Weinheim: Wiley-VCH, 2004.

    Book  Google Scholar 

  22. Saxena, A.K., Appl. Organomet. Chem., 1987, vol. 1, no. 1, pp. 39–56.

    Article  CAS  Google Scholar 

  23. Poller, R.C., in Organotin Compounds: New Chemistry and Applications, Zuckerman, J.J., Ed., Washington, DC: Amer. Chem. Soc., 1976, pp. 177–185.

  24. Von Blunden, S.J., Cusack, P.A., and Hill, R., Industrial Uses of Tin Chemicals, London: Royal Soc. Chem., 1985.

    Google Scholar 

  25. Zuckerman, J.J., Organotin Compounds: New Chemistry and Applications, Washington, DC: Amer. Chem. Soc., 1976.

    Book  Google Scholar 

  26. Evans, C.J., in Chemistry of Tin, Smith, P.J., Ed. London: Blackie, 1998, pp. 442–479.

    Google Scholar 

  27. Tsangaris, J.M. and Williem, D.K., Appl. Organomet. Chem., 1992, vol. 6, no. 1, pp. 3–18.

    Article  CAS  Google Scholar 

  28. Commission’s Scientific Committee on Health and Environmental Risks (SCHER). http://ec.europa.eu/ health/ph_risk/committees/04_scher/scher_opinions_ eu.htm. Cited November 30, 2006.

  29. Kocheshkov, K.A., Zemlyanskii, N.N., Sheverdina, N.I., and Panov, E.M., Metody elementoorganicheskoi khimii. Germanii, olovo, svinets (Methods of Organoelement Chemistry: Germanium, Tin, Lead), Moscow: Nauka, 1968.

  30. Kustov, L.M. and Beletskaya, I.P., Ross. Khim. Zh., 2004, vol. 48, no. 6, pp. 3–12.

    CAS  Google Scholar 

  31. Löwig, C.J., Ann. Chem. Pharm., 1852, vol. 84, no. 3, pp. 308–333.

    Article  Google Scholar 

  32. Von Frankland, E., Ann. Chem. Pharm., 1849, vol. 71, no. 2, pp. 171–213.

    Article  Google Scholar 

  33. Ingam, R., Rozenberg, S., and Gil’man, G., Olovoorganicheskie i germaniiorganicheskie soedineniya (Organotin and Organogermanium Compounds), Moscow: IL, 1962.

    Google Scholar 

  34. Neumann, W.P., Die organische chemie des zinns, Stuttgart: Ferdinand Enke Verlag, 1967.

    Google Scholar 

  35. Tsangaris, J.M., Willem, R., and Gielen, M., in The Chemistry of Organic Germanium, Tin, and Lead Compounds, Patai, S., Ed., Chichester: Wiley & Sons, 1995, ch. 10, pp. 453–535.

    Google Scholar 

  36. Nicholson, J.W., J. Chem. Educ., 1989, vol. 66, no. 8, p. 621.

    Article  CAS  Google Scholar 

  37. Van der Kerk, G.J.M., Luijten, J.G.A., and Noltes, J.G., Angew. Chem., 1958, vol. 70, no. 10, pp. 298–306.

    Article  CAS  Google Scholar 

  38. Neumann, W.P., Gemeinsam, N.A., Burkhardt, M.G., Heymann, E., Kleiner, F., König, K., Niermann, H., Pedain, J., Schick, R., Sommer, R., and Weller, H., Angew. Chem., 1963, vol. 75, no. 5, pp. 225–235.

    Article  CAS  Google Scholar 

  39. Rochow, E.G., J. Chem. Educ., 1966, vol. 43, no. 2, p. 58.

    Article  CAS  Google Scholar 

  40. Poller, R.C., Chemistry of Organotin Compounds, London: Logos Press/New York: Academic Press, 1970.

    Google Scholar 

  41. Van der Kerk, G.J.M., Ann. N. Y. Acad. Sci., 1974, vol. 239, no. 1, pp. 244–261.

    Article  CAS  Google Scholar 

  42. Voronkov, M.G. and Abzoeva, K.A., The Chemistry of Organic Germanium, Tin, and Lead Compounds, Rappoport, Z., Ed., New York: Wiley & Sons, 2002, vol. 2, ch. 1, pp. 1–130.

    Google Scholar 

  43. Luijten, J.G.A., Organomet. Chem. Rev., Sect. B, 1968, vol. 4, no. 3, pp. 359–393.

    CAS  Google Scholar 

  44. Luijten, J.G.A., Organomet. Chem. Rev., Sect. B, 1969, vol. 5, no. 4, pp. 687–735.

    CAS  Google Scholar 

  45. Luijten, J.G.A., Organomet. Chem. Rev., Sect. B, 1970, vol. 6, no. 2, pp. 486–540.

    CAS  Google Scholar 

  46. Bulten, E.J., Organomet. Chem. Rev., Sect. B, 1972, vol. 9, no. 2, pp. 248–338.

    CAS  Google Scholar 

  47. Bulten, E.J., J. Organomet. Chem., 1973, vol. 53, no. 1, pp. 1–96.

    Article  CAS  Google Scholar 

  48. Harrison, P.G., J. Organomet. Chem., 1973, vol. 58, no. 1, pp. 49–152.

    Article  CAS  Google Scholar 

  49. Harrison, P.G., J. Organomet. Chem., 1974, vol. 79, no. 1, pp. 17–174.

    Article  CAS  Google Scholar 

  50. Harrison, P.G., J. Organomet. Chem., 1976, vol. 109, no. 2, pp. 241–362.

    Article  CAS  Google Scholar 

  51. Harrison, P.G., J. Organomet. Chem. Libr., 1977, vol. 4, pp. 367–494.

    CAS  Google Scholar 

  52. Shiryaev, V.I., Stepina, E.M., and Mironov, V.F., in Elementoorganicheskie soedineniya (Organoelement Compounds), Moscow: Minkhimprom, 1976, vol. 3, pp. 5–82.

  53. Murphy, J. and Poller, R.C., J. Organomet. Chem. Libr., 1980, vol. 9, p. 189.

    Google Scholar 

  54. Kizlink, J., Chem. Listy, 1984, vol. 78, no. 2, pp. 134–145.

    CAS  Google Scholar 

  55. Cahours, A., C. R. Acad. Sci., Paris, 1852, vol, 35, p. 93.

  56. Cahours, A., Ann. Chem. Pharm., 1860, vol. 114, no. 2, pp. 227–255.

    Article  Google Scholar 

  57. Cahours, A., Ann. Chem. Pharm., 1860, vol. 114, no. 3, pp. 354–382.

    Article  Google Scholar 

  58. Cahours, A., Ann. Chem. Pharm., 1862, vol. 122, no. 1, pp. 48–71.

    Article  Google Scholar 

  59. Cahours, A., C. R. Acad. Sci., Paris, 1873, vol. 76, p. 133.

  60. Cahours, A. and Demarcay, E., C. R. Acad. Sci., Paris, 1879, vol. 88, p. 1112.

  61. Cahours, A. and Demarcay, E., C. R. Acad. Sci., Paris, 1879, vol. 89, p. 68.

  62. Cahours, A. and Demarcay, E., Bull. Soc. Chim. Fr., 1880, vol. 34, p. 474.

    Google Scholar 

  63. Grimm, A., J. Pract. Chem., 1954, vol. 62, p. 385.

    Article  Google Scholar 

  64. Ladenburg, A., Chem. Ber., 1870, vol. 3, p. 353.

    Article  Google Scholar 

  65. Ladenburg, A., Ann. Suppl., 1872, vol. 8, p. 55.

    Google Scholar 

  66. Frankland, E. and Lawrence, A., J. Chem. Soc., 1879, vol. 35, p. 130.

    Article  CAS  Google Scholar 

  67. Hjortdahl, M., Krist. Mineral., 1879, vol. 4, p. 286.

    Google Scholar 

  68. Werner, A. and Pfeiffer, P., Z. Anorg. Allg. Chem., 1898, vol. 17, no. 1, pp. 82–110.

    Article  CAS  Google Scholar 

  69. Emmert, B. and Eller, W., Chem. Ber., 1911, vol. 44, p. 388.

    Article  Google Scholar 

  70. Harada, T., Bull. Chem. Soc. Jpn., 1929, vol. 4, no. 11, pp. 266–270.

    Article  CAS  Google Scholar 

  71. Karantassis, T. and Basillides, K., C. R. Acad. Sci., Paris, 1937, vol. 205, p. 460.

  72. Karantassis, T. and Basillides, K., C. R. Acad. Sci., Paris, 1938, vol. 206, p. 842.

  73. Siebert, H., Z. Anorg. Allg. Chem., 1950, vol. 263, nos. 1–3, pp. 82–86.

  74. Okawara, R., Kagaku Ryoike, 1964, vol. 18, p. 3.

    Google Scholar 

  75. Harada, T., Repr. Sci. Res. Inst. (Tokyo), 1948, vol. 43, p. 31.

    CAS  Google Scholar 

  76. Neiman, M.B. and Shushunov, V.A., Zh. Fiz. Khim., 1948, vol. 22, no. 2, p. 145.

    CAS  Google Scholar 

  77. Neiman, M.B. and Shushunov, V.A., Dokl. Akad. Nauk SSSR. Ser. Fiz. Khim., 1948, vol. 60, no. 8, pp. 1347–1350.

    Google Scholar 

  78. Polis, A., Chem. Ber., 1889, vol. 22, p. 2915.

    Article  Google Scholar 

  79. Chambers, R.F. and Scherer, P.C., J. Am. Chem. Soc., 1926, vol. 48, no. 4, pp. 1054–1062.

    Article  CAS  Google Scholar 

  80. GB Patent 854776, 1960.

  81. Nad’, M.M. and Kocheshkov, K.A., Zh. Obshch. Khim., 1938, vol. 8, p. 42.

    Google Scholar 

  82. US Patent 2852543, 1958.

  83. Talalaeva, T.V. and Kocheshkov, K.A., Zh. Obshch. Khim., 1938, vol. 8, p. 1831.

    CAS  Google Scholar 

  84. Talalaeva, T.V. and Kocheshkov, K.A., Zh. Obshch. Khim., 1942, vol. 12, p. 403.

    CAS  Google Scholar 

  85. Sisido, K., Kozima, S., and Tuzi, T., J. Organomet. Chem., 1967, vol. 9, no. 1, pp. 109–115.

    Article  CAS  Google Scholar 

  86. US Patent 3651108, 1972.

  87. Galli, R. and Giannaccari, B.M., J. Organomet. Chem., 1970, vol. 25, no. 3, pp. 429–432.

    Article  CAS  Google Scholar 

  88. CA Patent 226140, 1926

  89. US Patent 1639947, 1927.

  90. Castel, P. and Gras, G., Trav. Soc. Pharm. Montpellier, 1957, vol. 17, p. 205.

    CAS  Google Scholar 

  91. GB Patent 469518, 1937.

  92. Zietz, J.R.Jr., Blitzer, S.M., Redman, H.E., and Ro-binson, G.C., J. Org. Chem., 1957, vol. 22, no. 1, pp. 60–62.

    Article  CAS  Google Scholar 

  93. Harada, T., Bull. Chem. Soc. Jpn., 1927, vol. 2, no. 4, pp. 105–109.

    Article  CAS  Google Scholar 

  94. Harada, T., Sci. Pap. Inst. Phys. Chem. Res. (Tokyo), 1940, vol. 38, p. 146.

    CAS  Google Scholar 

  95. Harada, T., Sci. Pap. Inst. Phys. Chem. Res. (Tokyo), 1939, vol. 35, p. 290.

    CAS  Google Scholar 

  96. Harada, T., Repr. Sci. Res. Inst. (Tokyo), 1948, vol. 24, p. 177.

    CAS  Google Scholar 

  97. Arntzene, C.E., Iowa State Coll. J. Sci., 1943, vol. 18, p. 6.

    Google Scholar 

  98. Gilman, H. and Arntzene, C.E., J. Org. Chem., 1950, vol. 15, no. 5, pp. 994–1002.

    Article  CAS  Google Scholar 

  99. GB Patent 736822, 1955.

  100. Thayer, J.S., Adv. Organomet. Chem., 1995, vol. 38, pp. 59–78.

    Article  CAS  Google Scholar 

  101. Luijten, J.G.A. and van der Kerk, G.J.M., in Organometallic Compounds of the Group IV Elements, McDiarmid, A.G., Ed., New York: Marcel Dekker, 1968, vol. 1, part 2, pp. 91–189.

    Google Scholar 

  102. Van der Kerk, G.J.M. and Luijten, J.G.A., J. Appl. Chem. (London, U. K.), 1954, vol. 4, no. 6, pp. 307–313.

    Article  CAS  Google Scholar 

  103. Luijten, J.G.A. and van der Kerk, G.J.M., Investigations in the Field of Organotin Chemistry, Greenford, Middlesex, UK: Tin Res. Inst., 1955.

    Google Scholar 

  104. GB Patent 713727, 1954.

  105. GB Patent 761357, 1956.

  106. Katsumura, T., Nippon Kagaku Zasshi, 1962, vol. 83, no. 6, p. 724.

    Article  CAS  Google Scholar 

  107. DE Patent 946447, 1956.

  108. USSR Inventor’s Certificate no. 137519, 1961.

  109. US Patent 3211769, 1965.

  110. Letts, E.A. and Collie, J.N., Proc. Chem. Soc., 1886, vol. 2, p. 166.

    Google Scholar 

  111. Letts, E.A. and Collie, J.N., Philos. Mag., 1886, vol. 22, no. 5, p. 41.

    Article  Google Scholar 

  112. Smith, A.C. and Rochow, E.G., J. Am. Chem. Soc., 1953, vol. 75, no. 16, p. 4103–4105.

    Article  CAS  Google Scholar 

  113. US Patent 2625559, 1953.

  114. US Patent 2679505, 1954.

  115. Unni, I.R. and Eapen, M.J., Indian J. Technol., 1977, vol. 15, p. 170.

    CAS  Google Scholar 

  116. US Patent 2679506, 1954.

  117. Rochow, E.G., Adv. Organomet. Chem., 1970, vol. 9, pp. 1–19.

    CAS  Google Scholar 

  118. Zaera, F., Acc. Chem. Res., 1992, vol. 25, no. 6, pp. 260–265.

    Article  CAS  Google Scholar 

  119. Mathewson, C.H., Z. Anorg. Allg. Chem., 1905, vol. 46, no. 1, pp. 94–112.

    Article  Google Scholar 

  120. Kurnakov, N.S., Vvedenie v fiziko-khimicheskii analiz (Introduction to Physicochemical Analysis), Leningrad: Izd. Akad. Nauk SSSR, 1940.

  121. Krause E. and von Grosse, A., Die chemie der metal-organischen Verbindungen, Berlin: Gebrüder Borntraeger, 1937, pp. 311–372.

    Google Scholar 

  122. Grure, G., Z. Anorg. Allg. Chem., 1905, vol. 46, no. 1, pp. 76–84.

    Article  Google Scholar 

  123. Mezbahul-Islam, M., Mostafa, A.O., and Madzaj, M., J. Mater., 2014. https://doi.org/10.1155/2014/704283

  124. Dvoinye i mnogokomponentnye sistemy na osnove medi (Binary and Multicomponent Copper Based Systems), Shukhardin, S.V., Ed., Moscow: Nauka, 1979.

    Google Scholar 

  125. Zakharkin, L.I. and Okhlobystin, O.Yu., Izv. Akad. Nauk SSSR, Ser. Khim., 1963, no. 12, pp. 2202–2204.

  126. Hurd, D.T. and Rochow, E.G., J. Am. Chem. Soc., 1945, vol. 67, no. 11, pp. 1057–1059.

    Article  CAS  Google Scholar 

  127. Klebanskii, A.L. and Fikhtengol’ts, V.S., Zh. Obshch. Khim., 1956, vol. 26, no. 9, pp. 2502.

    CAS  Google Scholar 

  128. Lewis, K.M., McLeod, D., Kanner, B. Falconer, J.L., and Frank, T.C., in Studies in Organic Chemistry, Lewis, K.M. and Rethwisch, D.G., Eds., Amsterdam: Elsevier, 1993, ch. 16, pp. 333–440.

    Google Scholar 

  129. Bažant, V. and Chvalovsky, J., Rathousky Organosilicon Compounds, New York: Academic Press, 1965, vol. 1.

    Google Scholar 

  130. Seyferth, D., Organometallics, 2001, vol. 20, no. 24, pp. 4978–4992. https://doi.org/10.1021/om0109051

    Article  CAS  Google Scholar 

  131. Shiryaev, V.I. and Mironov, V.F., Russ. Chem. Rev., 1983, vol. 52, no. 2, pp. 184–200.

    Article  Google Scholar 

  132. US Patent 2219463, 1940.

  133. BG Patent 813239, 1974.

Download references

Author information

Authors and Affiliations

  1. State Research Institute for the Chemistry and Technology of Organoelement Compounds, 105118, Moscow, Russia

    P. A. Storozhenko, K. D. Magdeev, A. A. Grachev & V. I. Shiryaev

Authors
  1. P. A. Storozhenko
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. K. D. Magdeev
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. A. A. Grachev
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. V. I. Shiryaev
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding authors

Correspondence to P. A. Storozhenko, K. D. Magdeev, A. A. Grachev or V. I. Shiryaev.

Additional information

Translated by E. Glushachenkova

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Storozhenko, P.A., Magdeev, K.D., Grachev, A.A. et al. Catalysts for the Direct Synthesis of Organotin Compounds, Part 1: Reactions between Organohalides and Tin Alloys. Catal. Ind. 13, 216–229 (2021). https://doi.org/10.1134/S2070050421030107

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S2070050421030107

Keywords:

Search

Navigation