Abstract
The Schiff base [1,2-bis(salicylidene amino)phenylene]cobalt(II) complex, chemically bonded to a carbamate-modified silica gel catalyst, has been prepared by a four step procedure. The oxidation of cyclohexane was studied in the presence of this catalyst under relatively mild conditions (150–200 °C, 15–20 atm) using molecular oxygen. The catalyst was found to be very selective for the production of cyclohexanol, with cyclohexanone formed in only a small amount (45:1). This is in contrast to the commercially available processes in which cyclohexanol and cyclohexanone are both formed in appreciable amounts. The t.g.a. analysis shows the catalyst to be stable up to 211 °C and atomic absorption spectroscopy indicated negligible metal loss during 50 h use of the catalyst up to 180 °C.
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H. Arakawa, M. Aresta, J.N. Armor, M.A. Barteau, E.J. Beckman, A.T. Bell, J.E. Bercaw, C. Creutz, E. Dinjus, D.A. Dixon, K. Domen, D.L. DuBois, J. Eckert, E. Fujita, D.H. Gibson, W.A. Goddard, D. Wayne Goodman, J. Keller, G.J. Kubas, H.H. Kung, J.E. Lyons, L.E. Manzer, T.J. Marks, K. Morokuma, K.M. Nicholas, R. Periana, L. Que, J.R. Nielson, W.M.H. Sachtler, L.D. Schmidt, A. Sen, G.A. Somorjai, P.C. Stair and B. Ray Stults, Chem. Rev., 101, 953 (2001).
N. Perkas, Y. Holypin, O. Patalik, A. Gedonken and S. Chandrasekhran, Appl. Catal. A Gen., 209, 125 (2001).
W.B. Fisher, J.F. Van Repper and M. Grayson (ed.), Krik-Othmer Encyclo. Tech., 3rd edit., Wiley, New York, 1979, vol. 7, p. 411.
K. Weissermel and H.J. Horpe, Industrial Organic Chemistry, 2nd edit., VCH press, Weinheim, 1993.
C.J. Moody and J. O'Connell, Chem. Commun., 1311 (2000).
C.B. Almquist and P. Biswas, Appl. Catal. A: Gen, 214, 259 (2001).
A. Sakthivel and P. Selvam, J. Catal., 211, 134 (2002).
U. Schuchardt, D. Cardoso, R. Sercheli, R. Pereira, R.S. da Cruz, M.C. Guerreiro, D. Mandelli, E.V. Spinace´ and E.L. Pires, J. Appl. Catal. A: Gen., 211, 1 (2001).
W.A. Carvalho, P.B. Varaldo, M. Wallau and U. Schuchardt, Zeolites, 18, 408 (1997).
U. Schuchardt, D. Cardoso and R. Sercheli et al., Appl. Catal A: Gen., 211, 01 (2001).
S.S. Lin and H.S. Weng, Appl. Catal. A: Gen., 118, 21(1994).
S. Kulkarni, M. Alurkar and A. Kumar, Appl. Catal. A: Gen., 142, 243 (1996).
R. Neumann and A.M. Khenkin, Inorg. Chem., 34, 5753 (1995).
N. Komiya, S. Noji and S.I. Murahashi, Chem. Commun., 65 (2001).
R. Raja, G. Shankar and J.M. Thomas, J. Am. Chem. Soc., 121, 11926 (1999).
G.S. Mishra and A. Kumar, J. Mol. Catal. A: Chem., 192, 275 (2003).
R.S. Drago, S.C. Petrousius and C.W. Chronister, Inorg. Chem., 33, 367 (1994).
J.D. Robert and M. Caserio, Basic Principal of Organic Chemistry, W.A. Benjamin Inc., New York, 1965, pp. 656 and 686.
S. Siggia, Quantitative Organic Analysis., 3rd edit., Wiley, New York, 1963, p. 558.
D.A. Atwood, Coord. Chem. Rev., 165, 267 (1997).
A. Nishinga, S. Yamazaki and T. Matsura, Tetrahedron. Lett., 29, 4118 (1998).
G.S. Mishra and A. Kumar, Catal. Lett., 81, 113 (2002).
M. Hartmann and S. Ernst, Angew. Chem. Int. Ed., 39, 888 (2000).
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Kumar, A., Mishra, G.S. & Kumar, A. Oxidation of cyclohexane with molecular oxygen using a Schiff base cobalt complex bonded to carbamate-modified silica gel. Transition Metal Chemistry 28, 913–917 (2003). https://doi.org/10.1023/A:1026334921387
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DOI: https://doi.org/10.1023/A:1026334921387