Study of a reduction step during the continuous synthesis of N-amino-3-azabicyclo[3.3.0]octane. Kinetics, modelling, and optimization
Tóm tắt
The reduction of N-chloro-3-azabicyclo[3.3.0]octane with sodium borohydride at different pH values and variable concentrations of the haloamine and reducing agent was studied. The reaction was found to be second order and exhibited a specific acid catalysis. The enthalpy and entropy of activation were determined at pH 12.89. A mathematical treatment of the kinetic data allowed a complete characterization of the final state and the determination of percentage of haloamine reduced as a function of temperature, [NaBH4]/[haloamine] ratio, arid pH. A reaction mechanism is proposed.
Tài liệu tham khảo
Martin, H. and Worthing, C.R., Pesticide Manuel, Nottingham: British Crop Protection Council, 1977.
Thomson, W.T., Insecticides, Herbicides, Fungicides, Fresno, Calif.: Thompson, 1977.
Kolla, V.E. and Berdinskii, I.S., Farmakologiya i khimiya proizvodnykh gidrazina (Pharmacology and Chemistry of Hydrazine Derivatives), Yoshkar-Ola: Mariiskoe Knizhnoe Izd., 1976.
Schmidt, E.W., Hydrazine and Its Derivatives: Preparation, Properties, Applications, New York: Wiley, 2001.
Wright, J.B. and Willette, R.E., J. Med. Pharm. Chem., 1962, vol. 5, p. 815.
Brown, E.V., Caglioti, L., Paolucci, G., Rosini, G., and Sucrow, W., Methodicum Chimicum, New York: Academic, 1975, p. 73.
Audrieth, L.F. and Ogg, B.A., Chemistry of Hydrazines, New York: Wiley, 1953.
Powel, P., Hydrazine Manufacturing Processes, New York: Wiley, 1968.
Kost, A.N. and Sagitullin, R.S., Russ. Chem. Rev., 1959, vol. 33, p. 159.
Ohme, R. and Zubek, A., Z. Chem., 1968, vol. 8, no. 2, p. 41.
Raschig, F., Chem.-Ztg., 1907, vol. 31, p. 926.
Raschig, F., Angew. Chem., 1907, vol. 20, p. 2065.
Raschig, F., Ber. D. Chem. Ges., 1907, vol. 40, p. 4580.
Elkhatib, M., Thèse de Ddoctorat ès Sciences no. 89-94, Lyon: Claude Bernard University Lyon 1, 1994.
Elkhatib, M., Marchand, A., Peyrot, L., Counioux, J.J., and Delalu, H., Int. J. Chem. Kinet., 1997, vol. 29, p. 89.
Elkhatib, M., Peyrot, L., Scharff, J.P., and Delalu, H., Int. J. Chem. Kinet., 1998, vol. 30, p. 129.
Lyttle, D.A., Jensen, E.H., and Struck, W.A., Anal. Chem., 1952, vol. 24, p. 1843.
Elkhatib, M., Marchand, A., Counioux, J.J., and Delalu, H., Int. J. Chem. Kinet., 1995, vol. 27, p. 757.
Schlesinger, H.I., Brown, H.C., Finholt, A.E., Gilbreath, J.R., Hoekstra, H.R., and Hyde, E.K., J. Am. Chem. Soc., 1953, vol. 75, p. 215.
Prokopcikas, A. and Salkauskiene, J., Russ. J. Phys. Chem., 1970, vol. 44, p. 1678.
Kreevoy, M.M. and Jacobson, R.W., Ventron Alembic, 1979, vol. 15, p. 2.
Kaufman, C.M. and Buddhadev, S., J. Chem. Soc., Dalton Trans., 1985, vol. 2, p. 307.
Miller, V.R., Ryschkewitsch, G.E., and Chandra, S., Inorg. Chem., 1970, vol. 9, p. 1427.
Lumbroso, H., Bull. Soc. Chim. Fr., 1963, vol. 11, p. 2519.
Allenstein, E., Z. Anorg. Allg. Chem., 1961, vol. 308, p. 1.
Delalu, H., Thèse de Doctorat d’État ès Science no. 77-29, Lyon: Claude Bernard University Lyon 1, 1977.