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.
Similar content being viewed by others
REFERENCES
Davies, A.G. and Smith, P.J., in Comprehensive Organometallic Chemistry, Oxford: Pergamon Press: Oxford, 1982, vol. 2, pp. 519–627.
Sawyer, A.K., in Organotin Compounds, New York: Marcel Dekker, 1971, vol. 3, pp. 625–1077.
Craig, P.J., in Environmental Aspects of Organometallic Chemistry, Oxford: Pergamon Press, 1982, vol. 2, ch. 18, pp. 979–1020.
Poller, R.C., in Organotin Compounds: New Chemistry and Applications, Ed. Zuckerman, J.J., Ed., Washington, DC: Amer. Chem. Soc., 1976, pp. 177–185.
Von Blunden, S.J., Cusack, P.A., and Hill, R., Industrial Uses of Tin Chemicals, London: Royal Soc. Chem., 1985.
Bailar, J.C.Jr., Catal. Rev., 1974, vol. 10, no. 1, pp. 17–36.
Saxena, A.K., Appl. Organomet. Chem., 1987, vol. 1, no. 1, pp. 39–56.
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.
Davies, A.G., Organotin Chemistry, Weinheim: Wiley-VCH, 2004.
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.
Luijten, J.G.A., Organomet. Chem. Rev., Sect. B, 1968, vol. 4, no. 3, pp. 359–393.
Luijten, J.G.A., Organomet. Chem. Rev., Sect. B, 1969, vol. 5, no. 4, pp. 687–735.
Luijten, J.G.A., Organomet. Chem. Rev., Sect. B, 1970, vol. 6, no. 2, pp. 486–540.
Bulten, E.J., Organomet. Chem. Rev., Sect. B, 1972, vol. 9, no. 2, pp. 248–338
Bulten, E.J., J. Organomet. Chem., 1973, vol. 53, no. 1, pp. 1–96.
Harrison, P.G., J. Organomet. Chem., 1973, vol. 58, no. 1, pp. 49–152.
Harrison, P.G., J. Organomet. Chem., 1974, vol. 79, no. 1, pp. 17–174.
Harrison, P.G., J. Organomet. Chem., 1976, vol. 109, no. 2, pp. 241–362.
Harrison, P.G., J. Organomet. Chem. Libr., 1977, vol. 4, pp. 367–494.
Shiryaev, V.I., Stepina, E.M., and Mironov, V.F., in Elementoorganicheskie soedineniya (Organoelement Compounds), Moscow: Minkhimprom, 1976, vol. 3, pp. 5–82.
Murphy, J. and Poller, R.C., J. Organomet. Chem. Libr., 1980, vol. 9, pp. 189–222.
Kizlink, J., Chem. Listy, 1984, vol. 78, no. 2, pp. 134–145.
Holland, F.S., Appl. Organomet. Chem., 1987, vol. 1, no. 5, pp. 449–458.
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
Von Frankland, E., Ann. Chem. Pharm., 1849, vol. 71, no. 2, pp. 171–213
Von Frankland, E., Ann. Chem. Pharm., 1849, vol. 71, no. 2, pp. 213–216.
Von Frankland, E., Ann. Chem. Pharm., 1853, vol. 85, no. 3, pp. 329–373.
Cahours, A., Ann. Chem. Pharm., 1860, vol. 114, no. 2, pp. 227–255.
Cahours, A., Ann. Chem. Pharm., 1860, vol. 114, no. 2, p. 244.
Cahours, A., Ann. Chem. Pharm., 1860, vol. 114, no. 3, pp. 354–382.
Werner, A. and Pfeiffer, P., Z. Anorg. Allg. Chem., 1898, vol. 17, no. 1, pp. 82–110.
Karantassis, T. and Basillides, K., C. R. Acad. Sci., Paris, 1937, vol. 205, p. 460.
Karantassis, T. and Basillides, K., C. R. Acad. Sci., Paris, 1938, vol. 206, p. 842.
Smith, A.C. and Rochow, E.G., J. Am. Chem. Soc., 1953, vol. 75, no. 16, p. 4103–4105.
Smith, A.C. and Rochow, E.G., J. Am. Chem. Soc., 1953, vol. 75, no. 16, p. 4105–4106.
CA Patent 504424, 1953.
US Patent 2679506, 1954.
Van der Kerk, G.J.M. and Luijten, G.J.A., Chimia, 1962, vol. 16, no. 2, pp. 36–42.
Jpn. Patent 13738, 1966.
Nosek, J., Collect. Czech. Chem. Commun., vol. 29, no. 12, pp. 3173–3175.
US Patent 3404167, 1968.
Jpn. Patent 6626, 1953.
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
Matsuda, S. and Matsuda, H.J., J. Chem. Soc. Japan, Ind. Chem. Sect., 1960, vol. 63, pp. 114–118.
Matsuda, S. and Matsuda, H.J., J. Chem. Soc. Japan, Ind. Chem. Sect., 1960, vol. 63, pp. 1958–1960.
Matsuda, S. and Matsuda, H.J., J. Chem. Soc. Japan, Ind. Chem. Sect., 1960, vol. 63, p. 1965.
Matsuda, H., Taniquchihi, H., and Matsuda, S.J., J. Chem. Soc. Japan, Ind. Chem. Sect., 1961, vol. 64, no. 2, pp. 541–543.
Matsuda, S., Matsuda, H.J., and Nakamura, M.J., J. Chem. Soc. Japan, Ind. Chem. Sect., 1961, vol. 64, p. 1948.
Matsuda, S., Matsuda, H.J., and Hayashi, J.J., J. Chem. Soc. Japan, Ind. Chem. Sect., 1961, vol. 64, p. 1951.
Matsuda, S. and Matsuda, H.J., Bull. Chem. Soc. Jpn., 1962, vol. 35, no. 2, pp. 208–211.
Jpn. Patent 25664, 1963.
Jpn. Patent 19115, 1963.
Jpn. Patent 7810, 1960.
Jpn. Patent 26194, 1964.
Jpn. Patent 13732, 1965.
Jpn. Patent 17669, 1963.
Jpn. Patent 36730, 1970.
Jpn. Patent 21289, 1968.
DE Patent 1050336, 1959.
Jpn. Patent 19116, 1963.
Jpn. Patent 19117, 1963.
Oakes, V. and Hutton, R.E., J. Organomet. Chem., 1965, vol. 3, no. 6, pp. 472–477.
Oakes, V. and Hutton, R.E., J. Organomet. Chem., 1966, vol. 6, no. 2, pp. 133–140.
GB Patent 1021426, 1966.
GB Patent 1118170, 1968.
GB Patent 1081823, 1967.
Ugo, R., Chiesa, A., and Fusi, A., J. Organomet. Chem., 1987, vol. 330, no. 1, pp. 25–30.
Kijima, T., Asakawa, A., and Kanisawa, H., J. Chem. Soc. Japan, Ind. Chem. Sect., 1969, vol. 72, no. 6, pp. 1353–1357.
GB Patent 1053996, 1967.
Jpn. Patent 1615, 1966.
Jpn. Patent 3164, 1971.
US Patent 3661958, 1972.
GB Patent 1276321, 1972.
US Patent 3745183, 1973.
Jpn. Patent 3618, 1966.
CA Patent 785318, 1968.
GB Patent 1115646, 1968.
GB Patent 1168456, 1969.
Matshiner, H., Voigländer, R., and Tzschach, A., J. Organomet. Chem., 1974, vol. 70, no. 3, pp. 387–391.
Chee, O.G. and Kumar Das, V.G., Appl. Organomet. Chem., 1988, vol. 2, no. 2, pp. 109–114.
Sisido, K., Kosima, S., and Tusi, T., J. Organomet. Chem., 1967, vol. 9, no. 1, pp. 109–115.
Jpn. Patent 24958, 1964.
Jpn. Patent 6738, 1966.
Jpn. Patent 6739, 1966.
Jpn. Patent 3617, 1966.
Jpn. Patent 42-2341, 1967.
US Patent 3857868, 1974.
US Patent 3901824, 1975.
Shiryaev, V.I., Stepina, E.M., Gladchenko, A.F., and Mironov, V.F., Available from. ONIITEKhIM, 1974, Cherkassy, 302/74.
US Patent 5258531, 1993.
US Patent 3970679, 1967.
DE Patent 2108966, 1974.
US Patent 3880743, 1975.
Sisido, K. and Kozima, S., J. Organomet. Chem., 1968, vol. 11, pp. 503–513.
US Patent 3547965, 1970.
US Patent 4510095, 1985.
US Patent 3471539, 1969.
US Patent 3475472, 1969.
US Patent 4092340, 1978.
US Patent 4179458, 1970.
Nicholson, J.W., Douek, J.A., and Collins, J.D., J. Organomet. Chem., 1982, vol. 233, no. 2, pp. 169–172.
US Patent 3519665, 1970.
NL Patent 6709983, 1969.
Van der Kerk, G.J.M., Luijten, J.G.A., and Noltes, J.G., Chimia, 1969, vol. 23, p. 9.
Van der Kerk, G.J.M., Luijten, J.G.A., and Noltes, J.G., Chimia, 1969, vol. 23, pp. 313–322.
Van der Kerk, G.J.M., Chem. Ind., 1970, vol. 20, pp. 644–647.
Kochergin, V.P., Shiryaev, V.I., and Mironov, V.F., Zh. Obshch. Khim., 1978, vol. 48, no. 6, p. 1428.
USSR Inventor’s Certificate no. 763348, Byull. Izobret., 1980, no. 34.
GB Patent 1275843, 1972.
GB Patent 1313485, 1971.
DE Patent 1217951, 1966.
US Patent 3387012, 1968.
USSR Inventor’s Certificate no. 457325, Byull. Izobret., 1983, no. 25.
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.
DE Patent 79015, 1971.
Jpn. Patent 78109, 1972.
Shiryaev, V.I., Stepina, E.M., Makhalkina, L.V., and Mironov, V.F., Available from VINITI, Moscow, 1975, no. 321/75.
Shiryaev, V.I., Stepina, E.M., Makhalkina, L.V., and Mironov, V.F., Available from ONIITEKhIM, Cherkassy, 1972, no. 519/75.
Fostein, P. and Pommier, J.C., J. Organomet. Chem., 1976, vol. 114, no. 1, pp. C7–C10.
Stepina, E.M., Shiryaev, V.I., Kuptsova, T.S., and Mironov, V.F., Available from ONIITEKhIM, Cherkassy, 1979, no. 2082/79.
USSR Inventor’s Certificate no. 447043, Byull. Izobret., 1983, no. 25.
GB Patent 1275842, 1972.
DE Patent 2225322, 1973.
Weisfeld, L.B., Kunstoffe, 1975, vol. 65, no. 5, pp. 298–299.
Stapfer, Ch., Plast. Mod. Elastomers, 1974, vol. 26, no. 9, pp. 82–85.
Feshin, V.P., Mironov, V.F., Mikhailyants, S.A., and Gar, T.K., Zh. Obshch. Khim., 1971, vol. 41, no. 10, pp. 2211–2217.
Klimsch, P., Plaste Kautsch., 1977, vol. 24, p. 380.
DE Patent 1239687, 1967.
CZ Patent 148776, 1968.
US Patent 3792059, 1974.
Shiryaev, V.I., Stepina, E.M., Makhalkina, L.V., and Mironov, V.F., Zh. Prikl. Khim., 1973, vol. 46, no. 5, p. 1149.
US Patent 4052426, 1977.
US Patent 3954820, 1976.
US Patent 4129584, 1978.
USSR Inventor’s Certificate no. 721444, Byull. Izobret., 1980, no. 10.
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.
Lindsell, W.E., in Comprehensive Organometallic Chemistry, Oxford: Pergamon Press, 1982, vol. 1, ch. 4, pp. 155–252.
Zakharkin, L.I. and Okhlobystin, O.Yu., Izv. Akad. Nauk SSSR, Otd. Khim. Nauk, 1963, no. 1, p. 193.
Norman, A., Usp. Khim., 1970, vol. 39, no. 6, pp. 990–1049.
Stepina, E.M., Studies on the chemistry and technology of the direct synthesis of organotin compounds, Cand. Sci. (Chem) Dissertation, Moscow, 1973.
Zaera, F.A., Acc. Chem. Res., 1992, vol. 25, no. 6, pp. 260–265.
Thayer, J.S., Adv. Organomet. Chem., 1995, vol. 38, pp. 59–78.
Ruby, S.L., Kalvins, G.M., Beard, G.B., and Snyder, R.E., Phys. Rev., 1967, vol. 159, no. 2, pp. 239–245.
Albert, M.R. and Yates, J.T., The Surface Scientist’s Guide to Organometallic Chemistry, Washington, DC: Amer. Chem. Soc., 1987.
Micklitz, H. and Barrett, P.H., Appl. Phys. Lett., 1972, vol. 20, no. 10, pp. 387–389.
Bos, A. and Ogden, J.C., J. Phys. Chem., 1973, vol. 77, no. 12, pp. 1513–1519.
Hauge, R.H., Kauffman, J., and Margrave, J.L., Abstract of Papers, Proc. 179th ACS Nat. Meet., Houston, TX, 1980.
Bos, A., Chem. Commun., 1972, no. 1, pp. 26–27.
Meier, P.F., Perry, D.L., Hauge, R.H., and Margrave, J.L., Inorg. Chem., 1979, vol. 18, no. 7, pp. 2051–2053.
Neumann, W.P., in The Organometallic and Coordination Chemistry of Germanium, Tin, and Lead, Tel-Aviv: Freund, 1978, pp. 51–74.
Nefedov, O.M., Kolesnikov, S.P., and Ioffe, A.I., J. Organomet. Chem. Libr., 1977, vol. 5, pp. 181–217.
Ioffe, A.I. and Nefedov, O.M., Zh. Vses. Khim. O-va im. D. I. Mendeleeva, 1979, vol. 24, no. 5, pp. 475–484.
Shiryaev, V.I. and Mironov, V.F., Usp. Khim., 1983, vol. 52, no. 2, pp. 321–347.
Kirk-Othmer Encyclopedia of Chemical Technology, New York: Wiley, 1969, vol. 20, pp. 312–314.
Abel, E.W., in Comprehensive Inorganic Chemistry, Oxford: Pergamon Press, 1973, vol. 2, pp. 43–104.
Holleman, A.F., and Wiberg, E., in Inorganic Chemistry, New York: Academic Press, 2001, ch. 15, pp. 778–928.
Ergan, S., Nature (London), Phys. Sci., 1973, vol. 241, pp. 65–67. https://doi.org/10.1038/phissci2410665bo
Barian, A., Dore, J.C., and Jurkiewicz, K., Rep. Prog. Phys., 2019, vol. 82, no. 1, https://doi.org/10.1088/1361-6633/aad6ab
Pearson, R.J., Usp. Khim., 1971, vol. 40, no. 7, pp. 1259–1282.
Pomeshchikov, V.D., Study of some intermediate stages in the reaction between butyl halides and tin, Cand. Sci. (Chem.) Dissertation, Moscow, 1974.
Pozdeev, V.V., Kinet. Katal., 1975, vol. 16, no. 3, pp. 624–628.
Kochergin, V.P., Shiryaev, V.I., Makhalkina, L.V., and Mironov, V.F., Available from ONIITEKhIM, Cherkassy, 1976, no. 1034/76.
Dehmlow, E.V., Angew. Chem., Int. Ed. Engl., 1974, vol. 13, p. 170.
Dehmlow, E.V., Angew. Chem., Int. Ed. Engl., 1977, vol. 16, p. 493.
Stepina, E.M., Shiryaev, V.I., Kuptsova, T.S., and Mironov, V.F., in Elementoorganicheskie soedineniya (Organoelement Compounds), Moscow: NIITEKhIM, 1978, no. 10.
Shiryaev, V.I., Stepina, E.M., Gladchenko, A.F., and Mironov, V.F., Chem. Abstr., 1976, no. 8Zh410.
Shiryaev, V.I., Stepina, E.M., Makhalkina, L.V., and Mironov, V.F., Chem. Abstr., 1975, no. 22Zh300.
Stepina, E.M., Shiryaev, V.I., Kuptsova, T.S., and Mironov, V.F., Chem. Abstr., 1979, no. 10Zh74.
Hauge, R.H., Kauffman, J., and Margrave, J.L., Chem. Abstr., 1982, no. 2V107.
Kochergin, V.P., Shiryaev, V.I., Makhalkina, L.V., and Mironov, V.F., Chem. Abstr., 1977, no. 4S476.
Author information
Authors and Affiliations
Corresponding authors
Additional information
Translated by E. Glushachenkova
Rights and permissions
About this article
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
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S2070050421040127