Abstract
Liquid-phase hydroxylation of phenol with H2O2 to a mixture of catechol and hydroquinone in acetonitrile has been reported using oxovanadium(IV) Schiff base complexes encapsulated in zeolite-Y as catalysts. Reaction conditions have been optimized by considering the concentration of substrate and oxidant, amount of catalyst, volume of solvent and temperature. Under the optimized reaction conditions, [VO(sal-1,3-pn)]-Y (H2sal-1,3-pn = N,N'-bis(salicylidene)propane-1,3-diamine) has shown the highest conversion of 34.3% after 6 h, [VO(salen)]-Y (H2salen = N,N'-bis(salicylidene)ethane-1,2-diamine) and [VO(saldien)]-Y (H2saldien = N,N'-bis(salicylidene)- diethylenetriamine) have comparable catalytic activity (∼33% conversion) while [VO(sal-1,2-pn)]-Y (H2sal-1,2-pn = N,N'-bis(salicylidene)propane-1,2-diamine) has the poorest performance (10.6% conversion). All these catalysts are more selective (90%) toward catechol formation except [VO(sal-1,3-pn)]-Y, which only gives ∼68% selectivity.
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References
H. Sigel and A. Sigel (Eds.) Vanadium and Its Role in Life, Metal Ions in Biological Systems, Vol. 31 (Marcel Dekker, New York, 1995).
A. Butler, Coord. Chem. Rev. 187 (1999) 17.
H. B. ten Brink, A. Tuynman, H. L. Dekker, W. Hemrika, Y. Izumi, T. Oshiro, H. E. Schoemaker and R. Wever, Inorg. Chem. 37 (1998) 6780.
M. A. Andersson and S. G. Allenmark, Tetrahedron 54 (1998) 15293.
G. B. Shul'pin and G. Suss-Fink, J. Chem. Soc. Perkin Trans. 2 (1995) 1459.
D. R. Pesiri, D. K. Morita, T. Walker and W. Tumas, Organometallics 18 (1999) 4916.
L. J. Csanyi, K. Jaky and G. Galbacs, J. Mol. Catal. A: Chemical 179 (2002) 65.
C.-Y. Chu, D.-R. Hwang, S.-K. Wang and B.-J. Uang, Chem. Commun. (2001) 980.
D. M. Boghaei and S. Mohebi, J. Mol. Catal. A: Chemical 179 (2002) 41.
A. Kozlov, K. Asakura and Y. Iwasawa, J. Chem. Soc. Faraday Trans. 94 (1998) 809.
N. Ulagappan and V. Krishnasamy, Indian J. Chem. 35A (1996) 787.
K. J. Balkus Jr., A. K. Khanmamedova, K. M. Dixon and F. Bedioui, Appl. Catal. A: General 143 (1996) 159.
G. S. Mishra and A. Kumar, Catal. Lett. 81 (2002) 113.
D. L. Hughes, U. Kleinkes, G. J. Leigh, M. Maiwald, J. R. Sanders, C. Sudbrake and J. Weisner, J. Chem. Soc. Dalton Trans. (1993) 3093.
M. R. Maurya, S. J. J. Titinchi and S. Chand, Appl. Catal. A: General 228 (2002) 177.
M. R. Maurya, S. J. J. Titinchi, S. Chand and I. M. Mishra, J. Mol. Catal. A: Chemical 180 (2002) 201.
C. Ratnasamy, A. Murugkar, S. Padhye and S. A. Pardhy, Indian J. Chem. 35A (1996) 1.
M. R. Maurya, S. Khurana, W. Zhang and D. Rehder, Eur. J. Inorg. Chem. (2002) 1749.
M. R. Maurya, S. J. J. Titinchi and S. Chand, J. Mol. Catal. A: Chemical (in press).
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Maurya, M.R., Kumar, M., Titinchi, S.J. et al. Oxovanadium(IV) Schiff Base Complexes Encapsulated in Zeolite-Y as Catalysts for the Liquid-Phase Hydroxylation of Phenol. Catalysis Letters 86, 97–105 (2003). https://doi.org/10.1023/A:1022619310956
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DOI: https://doi.org/10.1023/A:1022619310956