Skip to main content
Log in

Catalysts in the Direct Synthesis of Organotin Compounds, Part 2: Reactions between Alkyl Halides and Metallic Tin

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

Abstract

The second part of a series of reviews on the direct synthesis of organotin compounds is presented. In this part, the conditions and results of the reaction between metallic tin and allkyl halides are considered. The efficiency of application is analyzed for different catalysts along side with their systematization, 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

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

Instant access to the full article PDF.

Fig. 1.
Fig. 2.
Fig. 3.
Fig. 4.
Fig. 5.
Fig. 6.
Fig. 7.
Fig. 8.
Fig. 9.

Similar content being viewed by others

REFERENCES

  1. Davies, A.G. and Smith, P.J., in Comprehensive Organometallic Chemistry, Oxford: Pergamon Press: Oxford, 1982, vol. 2, pp. 519–627.

  2. Sawyer, A.K., in Organotin Compounds, New York: Marcel Dekker, 1971, vol. 3, pp. 625–1077.

    Google Scholar 

  3. Craig, P.J., in Environmental Aspects of Organometallic Chemistry, Oxford: Pergamon Press, 1982, vol. 2, ch. 18, pp. 979–1020.

    Google Scholar 

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

    Google Scholar 

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

    Google Scholar 

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

    CAS  Google Scholar 

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

    CAS  Google Scholar 

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

    Google Scholar 

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

    Google Scholar 

  10. 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 

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

    CAS  Google Scholar 

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

    CAS  Google Scholar 

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

    CAS  Google Scholar 

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

    CAS  Google Scholar 

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

    CAS  Google Scholar 

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

    CAS  Google Scholar 

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

    CAS  Google Scholar 

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

    CAS  Google Scholar 

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

    CAS  Google Scholar 

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

  21. Murphy, J. and Poller, R.C., J. Organomet. Chem. Libr., 1980, vol. 9, pp. 189–222.

    Google Scholar 

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

    CAS  Google Scholar 

  23. Holland, F.S., Appl. Organomet. Chem., 1987, vol. 1, no. 5, pp. 449–458.

    CAS  Google Scholar 

  24. Storozhenko, P.A., Magdeev, K.D., Grachev, A.A., and Shiryaev, V.I., Catal. Ind., 2021, vol. 13, no. 3, pp. 216–229. https://doi.org/10.1134/S2070050421030107

    Article  Google Scholar 

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

    Google Scholar 

  26. Von Frankland, E., Ann. Chem. Pharm., 1849, vol. 71, no. 2, pp. 213–216.

    Google Scholar 

  27. Von Frankland, E., Ann. Chem. Pharm., 1853, vol. 85, no. 3, pp. 329–373.

    Google Scholar 

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

    Google Scholar 

  29. Cahours, A., Ann. Chem. Pharm., 1860, vol. 114, no. 2, p. 244.

    Google Scholar 

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

    Google Scholar 

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

    CAS  Google Scholar 

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

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

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

    CAS  Google Scholar 

  35. Smith, A.C. and Rochow, E.G., J. Am. Chem. Soc., 1953, vol. 75, no. 16, p. 4105–4106.

    CAS  Google Scholar 

  36. CA Patent 504424, 1953.

  37. US Patent 2679506, 1954.

  38. Van der Kerk, G.J.M. and Luijten, G.J.A., Chimia, 1962, vol. 16, no. 2, pp. 36–42.

    CAS  Google Scholar 

  39. Jpn. Patent 13738, 1966.

  40. Nosek, J., Collect. Czech. Chem. Commun., vol. 29, no. 12, pp. 3173–3175.

  41. US Patent 3404167, 1968.

  42. Jpn. Patent 6626, 1953.

  43. Sisido, K., Takeda, Y., and Kinugawa, Z.J., J. Amer. Chem. Soc., 1961, vol. 83, no. 3, pp. 538–541. https://doi.org/10.1021/ja01464a008

    Article  Google Scholar 

  44. Matsuda, S. and Matsuda, H.J., J. Chem. Soc. Japan, Ind. Chem. Sect., 1960, vol. 63, pp. 114–118.

    CAS  Google Scholar 

  45. Matsuda, S. and Matsuda, H.J., J. Chem. Soc. Japan, Ind. Chem. Sect., 1960, vol. 63, pp. 1958–1960.

    CAS  Google Scholar 

  46. Matsuda, S. and Matsuda, H.J., J. Chem. Soc. Japan, Ind. Chem. Sect., 1960, vol. 63, p. 1965.

    CAS  Google Scholar 

  47. Matsuda, H., Taniquchihi, H., and Matsuda, S.J., J. Chem. Soc. Japan, Ind. Chem. Sect., 1961, vol. 64, no. 2, pp. 541–543.

    CAS  Google Scholar 

  48. Matsuda, S., Matsuda, H.J., and Nakamura, M.J., JChem. Soc. Japan, Ind. Chem. Sect., 1961, vol. 64, p. 1948.

    CAS  Google Scholar 

  49. Matsuda, S., Matsuda, H.J., and Hayashi, J.J., J. Chem. Soc. Japan, Ind. Chem. Sect., 1961, vol. 64, p. 1951.

    CAS  Google Scholar 

  50. Matsuda, S. and Matsuda, H.J., Bull. Chem. Soc. Jpn., 1962, vol. 35, no. 2, pp. 208–211.

    Google Scholar 

  51. Jpn. Patent 25664, 1963.

  52. Jpn. Patent 19115, 1963.

  53. Jpn. Patent 7810, 1960.

  54. Jpn. Patent 26194, 1964.

  55. Jpn. Patent 13732, 1965.

  56. Jpn. Patent 17669, 1963.

  57. Jpn. Patent 36730, 1970.

  58. Jpn. Patent 21289, 1968.

  59. DE Patent 1050336, 1959.

  60. Jpn. Patent 19116, 1963.

  61. Jpn. Patent 19117, 1963.

  62. Oakes, V. and Hutton, R.E., J. Organomet. Chem., 1965, vol. 3, no. 6, pp. 472–477.

    CAS  Google Scholar 

  63. Oakes, V. and Hutton, R.E., J. Organomet. Chem., 1966, vol. 6, no. 2, pp. 133–140.

    CAS  Google Scholar 

  64. GB Patent 1021426, 1966.

  65. GB Patent 1118170, 1968.

  66. GB Patent 1081823, 1967.

  67. Ugo, R., Chiesa, A., and Fusi, A., J. Organomet. Chem., 1987, vol. 330, no. 1, pp. 25–30.

    CAS  Google Scholar 

  68. Kijima, T., Asakawa, A., and Kanisawa, H., J. Chem. Soc. Japan, Ind. Chem. Sect., 1969, vol. 72, no. 6, pp. 1353–1357.

    CAS  Google Scholar 

  69. GB Patent 1053996, 1967.

  70. Jpn. Patent 1615, 1966.

  71. Jpn. Patent 3164, 1971.

  72. US Patent 3661958, 1972.

  73. GB Patent 1276321, 1972.

  74. US Patent 3745183, 1973.

  75. Jpn. Patent 3618, 1966.

  76. CA Patent 785318, 1968.

  77. GB Patent 1115646, 1968.

  78. GB Patent 1168456, 1969.

  79. Matshiner, H., Voigländer, R., and Tzschach, A., J. Organomet. Chem., 1974, vol. 70, no. 3, pp. 387–391.

    Google Scholar 

  80. Chee, O.G. and Kumar Das, V.G., Appl. Organomet. Chem., 1988, vol. 2, no. 2, pp. 109–114.

    CAS  Google Scholar 

  81. Sisido, K., Kosima, S., and Tusi, T., J. Organomet. Chem., 1967, vol. 9, no. 1, pp. 109–115.

    CAS  Google Scholar 

  82. Jpn. Patent 24958, 1964.

  83. Jpn. Patent 6738, 1966.

  84. Jpn. Patent 6739, 1966.

  85. Jpn. Patent 3617, 1966.

  86. Jpn. Patent 42-2341, 1967.

  87. US Patent 3857868, 1974.

  88. US Patent 3901824, 1975.

  89. Shiryaev, V.I., Stepina, E.M., Gladchenko, A.F., and Mironov, V.F., Available from. ONIITEKhIM, 1974, Cherkassy, 302/74.

  90. US Patent 5258531, 1993.

  91. US Patent 3970679, 1967.

  92. DE Patent 2108966, 1974.

  93. US Patent 3880743, 1975.

  94. Sisido, K. and Kozima, S., J. Organomet. Chem., 1968, vol. 11, pp. 503–513.

    CAS  Google Scholar 

  95. US Patent 3547965, 1970.

  96. US Patent 4510095, 1985.

  97. US Patent 3471539, 1969.

  98. US Patent 3475472, 1969.

  99. US Patent 4092340, 1978.

  100. US Patent 4179458, 1970.

  101. Nicholson, J.W., Douek, J.A., and Collins, J.D., J. Organomet. Chem., 1982, vol. 233, no. 2, pp. 169–172.

    CAS  Google Scholar 

  102. US Patent 3519665, 1970.

  103. NL Patent 6709983, 1969.

  104. Van der Kerk, G.J.M., Luijten, J.G.A., and Noltes, J.G., Chimia, 1969, vol. 23, p. 9.

    Google Scholar 

  105. Van der Kerk, G.J.M., Luijten, J.G.A., and Noltes, J.G., Chimia, 1969, vol. 23, pp. 313–322.

    CAS  Google Scholar 

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

    Google Scholar 

  107. Kochergin, V.P., Shiryaev, V.I., and Mironov, V.F., Zh. Obshch. Khim., 1978, vol. 48, no. 6, p. 1428.

    CAS  Google Scholar 

  108. USSR Inventor’s Certificate no. 763348, Byull. Izobret., 1980, no. 34.

  109. GB Patent 1275843, 1972.

  110. GB Patent 1313485, 1971.

  111. DE Patent 1217951, 1966.

  112. US Patent 3387012, 1968.

  113. USSR Inventor’s Certificate no. 457325, Byull. Izobret., 1983, no. 25.

  114. Kocheshkov, K.A., Skoldinov, A.P., and Zemlyanskii, N.N., Metody elementoorganicheskoi khimii. Sur’ma, vismut (Methods of Organoelement Chemistry: Antimony, Bismuth) Moscow: Nauka, 1976.

  115. DE Patent 79015, 1971.

  116. Jpn. Patent 78109, 1972.

  117. Shiryaev, V.I., Stepina, E.M., Makhalkina, L.V., and Mironov, V.F., Available from VINITI, Moscow, 1975, no. 321/75.

  118. Shiryaev, V.I., Stepina, E.M., Makhalkina, L.V., and Mironov, V.F., Available from ONIITEKhIM, Cherkassy, 1972, no. 519/75.

  119. Fostein, P. and Pommier, J.C., J. Organomet. Chem., 1976, vol. 114, no. 1, pp. C7–C10.

    CAS  Google Scholar 

  120. Stepina, E.M., Shiryaev, V.I., Kuptsova, T.S., and Mironov, V.F., Available from ONIITEKhIM, Cherkassy, 1979, no. 2082/79.

  121. USSR Inventor’s Certificate no. 447043, Byull. Izobret., 1983, no. 25.

  122. GB Patent 1275842, 1972.

  123. DE Patent 2225322, 1973.

  124. Weisfeld, L.B., Kunstoffe, 1975, vol. 65, no. 5, pp. 298–299.

    CAS  Google Scholar 

  125. Stapfer, Ch., Plast. Mod. Elastomers, 1974, vol. 26, no. 9, pp. 82–85.

    Google Scholar 

  126. Feshin, V.P., Mironov, V.F., Mikhailyants, S.A., and Gar, T.K., Zh. Obshch. Khim., 1971, vol. 41, no. 10, pp. 2211–2217.

    Google Scholar 

  127. Klimsch, P., Plaste Kautsch., 1977, vol. 24, p. 380.

    CAS  Google Scholar 

  128. DE Patent 1239687, 1967.

  129. CZ Patent 148776, 1968.

  130. US Patent 3792059, 1974.

  131. Shiryaev, V.I., Stepina, E.M., Makhalkina, L.V., and Mironov, V.F., Zh. Prikl. Khim., 1973, vol. 46, no. 5, p. 1149.

    CAS  Google Scholar 

  132. US Patent 4052426, 1977.

  133. US Patent 3954820, 1976.

  134. US Patent 4129584, 1978.

  135. USSR Inventor’s Certificate no. 721444, Byull. Izobret., 1980, no. 10.

  136. Stepina, E.M., Afanas’ev, A.I., Shiryaev, V.I., Kovaleva, E.A., and Mironov, V.F., in Elementoorganicheskie soedineniya (Organoelement Compounds), Moscow: NIITEKhIM, 1979, no. 3.

  137. Lindsell, W.E., in Comprehensive Organometallic Chemistry, Oxford: Pergamon Press, 1982, vol. 1, ch. 4, pp. 155–252.

    Google Scholar 

  138. Zakharkin, L.I. and Okhlobystin, O.Yu., Izv. Akad. Nauk SSSR, Otd. Khim. Nauk, 1963, no. 1, p. 193.

  139. Norman, A., Usp. Khim., 1970, vol. 39, no. 6, pp. 990–1049.

    Google Scholar 

  140. Stepina, E.M., Studies on the chemistry and technology of the direct synthesis of organotin compounds, Cand. Sci. (Chem) Dissertation, Moscow, 1973.

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

    CAS  Google Scholar 

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

    CAS  Google Scholar 

  143. Ruby, S.L., Kalvins, G.M., Beard, G.B., and Snyder, R.E., Phys. Rev., 1967, vol. 159, no. 2, pp. 239–245.

    CAS  Google Scholar 

  144. Albert, M.R. and Yates, J.T., The Surface Scientist’s Guide to Organometallic Chemistry, Washington, DC: Amer. Chem. Soc., 1987.

    Google Scholar 

  145. Micklitz, H. and Barrett, P.H., Appl. Phys. Lett., 1972, vol. 20, no. 10, pp. 387–389.

    CAS  Google Scholar 

  146. Bos, A. and Ogden, J.C., J. Phys. Chem., 1973, vol. 77, no. 12, pp. 1513–1519.

    CAS  Google Scholar 

  147. Hauge, R.H., Kauffman, J., and Margrave, J.L., Abstract of Papers, Proc. 179th ACS Nat. Meet., Houston, TX, 1980.

  148. Bos, A., Chem. Commun., 1972, no. 1, pp. 26–27.

  149. Meier, P.F., Perry, D.L., Hauge, R.H., and Margrave, J.L., Inorg. Chem., 1979, vol. 18, no. 7, pp. 2051–2053.

    CAS  Google Scholar 

  150. Neumann, W.P., in The Organometallic and Coordination Chemistry of Germanium, Tin, and Lead, Tel-Aviv: Freund, 1978, pp. 51–74.

  151. Nefedov, O.M., Kolesnikov, S.P., and Ioffe, A.I., J. Organomet. Chem. Libr., 1977, vol. 5, pp. 181–217.

    CAS  Google Scholar 

  152. Ioffe, A.I. and Nefedov, O.M., Zh. Vses. Khim. O-va im. D. I. Mendeleeva, 1979, vol. 24, no. 5, pp. 475–484.

    CAS  Google Scholar 

  153. Shiryaev, V.I. and Mironov, V.F., Usp. Khim., 1983, vol. 52, no. 2, pp. 321–347.

    CAS  Google Scholar 

  154. Kirk-Othmer Encyclopedia of Chemical Technology, New York: Wiley, 1969, vol. 20, pp. 312–314.

  155. Abel, E.W., in Comprehensive Inorganic Chemistry, Oxford: Pergamon Press, 1973, vol. 2, pp. 43–104.

    Google Scholar 

  156. Holleman, A.F., and Wiberg, E., in Inorganic Chemistry, New York: Academic Press, 2001, ch. 15, pp. 778–928.

    Google Scholar 

  157. Ergan, S., Nature (London), Phys. Sci., 1973, vol. 241, pp. 65–67. https://doi.org/10.1038/phissci2410665bo

    Article  Google Scholar 

  158. Barian, A., Dore, J.C., and Jurkiewicz, K., Rep. Prog. Phys., 2019, vol. 82, no. 1, https://doi.org/10.1088/1361-6633/aad6ab

  159. Pearson, R.J., Usp. Khim., 1971, vol. 40, no. 7, pp. 1259–1282.

    Google Scholar 

  160. Pomeshchikov, V.D., Study of some intermediate stages in the reaction between butyl halides and tin, Cand. Sci. (Chem.) Dissertation, Moscow, 1974.

  161. Pozdeev, V.V., Kinet. Katal., 1975, vol. 16, no. 3, pp. 624–628.

    CAS  Google Scholar 

  162. Kochergin, V.P., Shiryaev, V.I., Makhalkina, L.V., and Mironov, V.F., Available from ONIITEKhIM, Cherkassy, 1976, no. 1034/76.

  163. Dehmlow, E.V., Angew. Chem., Int. Ed. Engl., 1974, vol. 13, p. 170.

    Google Scholar 

  164. Dehmlow, E.V., Angew. Chem., Int. Ed. Engl., 1977, vol. 16, p. 493.

    Google Scholar 

  165. Stepina, E.M., Shiryaev, V.I., Kuptsova, T.S., and Mironov, V.F., in Elementoorganicheskie soedineniya (Organoelement Compounds), Moscow: NIITEKhIM, 1978, no. 10.

  166. Shiryaev, V.I., Stepina, E.M., Gladchenko, A.F., and Mironov, V.F., Chem. Abstr., 1976, no. 8Zh410.

  167. Shiryaev, V.I., Stepina, E.M., Makhalkina, L.V., and Mironov, V.F., Chem. Abstr., 1975, no. 22Zh300.

  168. Stepina, E.M., Shiryaev, V.I., Kuptsova, T.S., and Mironov, V.F., Chem. Abstr., 1979, no. 10Zh74.

  169. Hauge, R.H., Kauffman, J., and Margrave, J.L., Chem. Abstr., 1982, no. 2V107.

  170. Kochergin, V.P., Shiryaev, V.I., Makhalkina, L.V., and Mironov, V.F., Chem. Abstr., 1977, no. 4S476.

Download references

Author information

Authors and Affiliations

Authors

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 in the Direct Synthesis of Organotin Compounds, Part 2: Reactions between Alkyl Halides and Metallic Tin. Catal. Ind. 13, 337–351 (2021). https://doi.org/10.1134/S2070050421040127

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S2070050421040127

Keywords:

Navigation