Abstract
The kinetics of phosphine hydroxymethylation with formaldehyde is studied. In the absence of a catalyst, phosphine reacts slowly with formaldehyde under normal conditions. Taken separately, amines, hydrochloric acid, and nickel chloride have a low catalytic activity, but the addition of a primary aliphatic amine to nickel chloride effectively increases the hydroxymethylation rate. A probable reaction mechanism is suggested.
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References
Erastov, O.V. and Nikonov, G.E., Funktsional’nye zameshchennye fosfiny i ikh proizvodnye (Functionalized Phosphines and Their Derivatives), Moscow: Nauka, 1986.
Petrov, K.A. and Parshina, V.A., Usp. Khim., 1968, vol. 37, no. 7, p. 1218.
German Patent 1035 135, 1959.
Shaikhutdinova, I.T., Cand. Sci. (Chem.) Dissertation, Alma-Ata: Inst. of Organic Catalysis and Electrochemistry, 1986.
Reid, R.C., Prausnitz, J.M., and Sherwood, T.K., The Properties of Gases and Liquids, New York: McGraw-Hill, 1977.
Zhigach, A.F. and Stasinevich, D.S., Khimiya gidridov (Hydride Chemistry), Leningrad: Khimiya, 1969.
Moelwyn-Hughes, E.A., The Chemical Statics and Kinetics of Solution, London: Academic, 1971.
Ogorodnikov, S.K., Formal’degid (Formaldehyde), Leningrad, 1984.
Mazor, L., Methods of Organic Analysis, Budapest: Akadémiai Kiadö, 1983.
Purdela, D. and Vilceanu, R., Chimia compusilor organici ai fosforului si ai acizilor luj, Timishoara, Romania, 1965.
Corbridge, D., Phosphorus: An Outline of Its Chemistry, Biochemistry, and Technology, Amsterdam: Elsevier, 1980.
Nifant’ev, E.E. and Vasyanina, L.K., Spektroskopiya YaMR 31 P (31P NMR Spectroscopy), Moscow: Mosk. Gos. Pedagog. Inst., 1986.
Nakanisi, K., Infrared Absorption Spectroscopy, San Francisco: Holden-Day, 1962.
Gordon, A.J. and Ford, R.A., The Chemist’s Companion, New York: Wiley, 1972.
Hartley, F.R., Burgess, C., and Alcock, R.M., Solution Equilibria, New York: Ellis Horwood, 1980.
Fluck, E. and Novobilsky, V., Chem. Forsch., 1969, vol. 13, p. 125.
USSR Inventor’s Certificate No. 1145022, Byull. Izobret., 1985, no. 10.
Schmid, R. and Sapunov, V., Non-formal Kinetics, Weinheim: Chemie, 1982.
Sokol’skii, D.V. and Dorfman, Ya.A., Kataliz ligandami v vodnykh rastvorakh (Catalysis by Ligands in Aqueous Solutions), Alma-Ata: Nauka, 1972.
Knowles, W.S., Sabacky, M.J., and Vineyard, B.D., Ann. N. Y. Acad. Sci., 1970, vol. 172, no. 9, p. 232.
Bogdanovic, B., Adv. Organomet. Chem., 1979, vol. 17, p. 105.
Dorfman, Ya.A., Levina, L.V., and Grekov, L.I., Zh. Obshch. Khim., 1995, vol. 65, no. 9, p. 1459.
Dorfman, Ya.A., Levina, L.V., Grekov, L.I., and Korolev, A.V., Kinet. Katal., 1989, vol. 30, no. 3, p. 662.
Beck, M.T. and Nagypal, I., Chemistry of Complex Equilibria, Budapest: Akadémiai Kiadö, 1989.
German Pat. Appl. 2636558, 1978.
Trofimov, B.A., Arbuzova, S.N., and Gusarova, N.K., Usp. Khim., 1999, vol. 68, no. 3, p. 240.
Gunderman, K. and Garming, A., Chem. Ber., 1969.
Rauhut, M.M. and Hechenblekner, J., J. Am. Chem. Soc., 1959, vol. 81, p. 1103.
Bjerrum, Ya., Metal Ammine Formation in Aqueous Solution, Copenhagen: Haase, 1957.
Kukushkin, Yu.N., Reaktsionnaya sposobnost’ koordinatsionnykh soedinenii (Reactivity of Coordination Compounds), Leningrad: Khimiya, 1987.
Grekov, L.I., Novakov, I.A., and Tuzhikov, O.I., Khim. Prom-st. Segodnya, 2003, no. 12, p. 9.
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Original Russian Text © L.I. Grekov, I.A. Novakov, 2006, published in Kinetika i Kataliz, 2006, Vol. 47, No. 3, pp. 364–372.
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Grekov, L.I., Novakov, I.A. Kinetics of phosphine hydroxymethylation with formaldehyde. Kinet Catal 47, 358–366 (2006). https://doi.org/10.1134/S0023158406030062
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DOI: https://doi.org/10.1134/S0023158406030062