Abstract
Oxidative carbonylation of benzene and toluene catalyzed by Pd or Rh compounds in the presence of Cu, Fe, V, or Mo compounds in a mixture of trifluoroacetic acid and its anhydride at 125-150°C and partial pressures of carbon monoxide of 0.6-4.7 MPa and oxygen of 0.2-0.8 MPa leads to the corresponding aromatic acids with the yields of up to ca. 50% and 1800 mol per g-atom of the platinum group metal which is tens times higher than that achievable in the absence of oxygen. With the use of IR spectroscopy in situ it was shown that an acyl complex of Pd is formed, and the possibility of determination of the oxidation state of the cation of Cu in the course of oxidative carbonylation was demonstrated.
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REFERENCES
US Patent no. 3 920 734, 1975; Ref. Zh. Khim., 1977, 5 N 173 P.
Kalinovskii, I.O., Pogorelov, V.V., Gel'bshtein, A.I., and Akhmedov, N.G., Zh. Obshch. Khim., 2001, vol. 71, no. 9, pp. 1539–1544.
Fujiwara, Y., Kawanchi, T., and Taniguchi, H., Chem. Commun., 1980, no. 5, p. 220.
Masters, C., Homogeneous Transition–metal Catalysis, London: Chapman and Hall, 1981. Translated under the title Gomogennyi kataliz perekhodnymi metallami, Moscow: Mir, 1983, p. 300.
Moiseev, I.I., Vargaftik, M.N., and Syrkin, Ya.K., Dokl. Akad. Nauk SSSR, 1960, vol. 130, no. 4, pp. 820–823.
US Patent no. 4 431 839, 1984; Ref. Zh. Khim., 1984, 22 N 150 P.
Kalinovskii, I.O., Leshcheva, A.A., Kuteinikova, M.M., and Cel'bshtein, A.I., Zh. Obshch. Khim., 1990, vol. 60, no. 1, pp. 123–130.
Zhizhinas, E.G., Matveev, K.I., and Kuznetsova, L.I., Kinet. Katal., 1985, vol. 26, no.2, pp. 461–465.
Arzoumanidis, G.G. and Rauch, F.C., J. Mol. Catal., 1980, vol. 9, no. 3, pp. 335–338.
Kalinovskii, I.O., Leshcheva, A.A., Pogorelov, V.V., and Gel'bshtein, A.I., Khim. Tverd. Topl., 1993, no. 2, pp. 8–10.
Leshcheva, A.A., Kalinovskii, I.O., Pogorelov, V.V., Noskov, Yu.G., and Gel'bshtein, A.I., Kinet. Katal., 1998, vol. 39, no. 3, pp. 389–398.
Carrou, P.E. and Heck, R.F., J. Am. Chem. Soc., 1976, vol. 98, no. 14, pp. 4115–4127.
Collman, J.P., Hegedus, L.S., Norton, J.R., and Finke, R.G., Principles and Applications of Organotransition Metal Chemistry, Mill Valley, CA: University Science Books, 1987. Translated under the title Metalloorganicheskaya khimiya perekhodnykh metallov, Moscow: Mir, 1989, vol. 1, pp. 108–113.
Scott, A.F., Wilkening, L.L., and Rubin, B., Inorg. Chem., 1969, vol. 8, no. 11, pp. 2533–2534.
Stephenson, T.A., Morehouse, S.M., Powell, A.R., Heffer, J.P., and Wilkinson, G., J. Chem. Soc., 1965, no. 6, pp. 3632–3640.
Henry, P.M., Palladium–catalysed organic reactions, Adv. Organometal. Chem., 1975, vol. 13, pp. 363–452.
Inorganic synthesis, New York: McGraw–Hill, 1966, vol. 8, pp. 211–213.
Patel, K.S. and Fanisan, J.A., J. Inorg. Nucl. Chem., 1976, vol. 38, no. 5, pp. 1001–1005
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Kalinovskii, I.O., Gel'bshtein, A.I. & Pogorelov, V.V. Oxidative Carbonylation of Benzene and Toluene Catalyzed by Compounds of Pd or Rh in Trifluoroacertic Acid and its Anhydride in the Presence of Cu, Fe, V, or Mo Compounds, with Oxygen as an Oxidant. Russian Journal of General Chemistry 71, 1463–1466 (2001). https://doi.org/10.1023/A:1013922523320
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DOI: https://doi.org/10.1023/A:1013922523320