Abstract
A series of transition metal complexes of 3-[N,N′-bis-3-(salicylidenamino)ethyltriamine] (salten) immobilized on MCM-41 were prepared for the solvent and additive-free selective oxidation of cyclohexanol with 30 % hydrogen peroxide (H2O2). The immobilized complexes were effective catalysts and exhibited much higher catalytic performance than their homogeneous analogues. Moreover, the metal centers were found to play important roles in the catalytic performance of immobilized complexes. When the immobilized chromium complex was used as catalyst, the optimal cyclohexanol conversion could reach 90.5 % with 100 % of the selectivity to cyclohexanone. In addition, the catalytic performance remained after being recycled five times.
Graphical Abstract
Owing to the different 3d electronic numbers of metal centers, eight kinds of immobilized Schiff base complexes exhibited significantly different catalytic performance in the selective oxidation of cyclohexanol with 30 % H2O2. The optimal cyclohexanol conversion could reach 90.5 % with 100 % of the selectivity to cyclohexanone over immobilized chromium complex.
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Markó IE, Giles PR, Tsukazaki M, Brown SM, Urch CJ (1996) Science 274:2044
Thorp HH (2000) Science 289:882
Bakac A (1995) In: Karlin DK (ed) Mechanistic and kinetics aspects of transition metal oxygen chemistry in progress in inorganic chemistry, vol 43. Wiley, New York, p 297
Hong LS (2001) The Hong Kong Polytechnic University, Doctoral dissertation
Balbinot L, Schuchardt U, Vera C, Sepúlveda J (2008) Catal Commun 9:1878
Jana SK, Kubota Y, Tatsumi T (2008) J Catal 225:40
Shul’pin GB, Matthes MG, Romakh VB, Barbosa MIF, Aoyagi JLT, Mandelli D (2008) Tetrahedron 64:2143
Stamatis A, Doutsi P, Vartzouma Ch, Christoforidis KC, Deligiannakis Y, Louloudi M (2009) J Mol Catal A 297:44
Arunachalam S, Padma Priya N, Jayabalakrishnan C, Chinnusamy V (2009) Spectrochim Acta A 74:591
Andrews M, Laye RH, Pope’s JA (2009) Transit Met Chem 34:493
Parida KM, Sahoo M, Singha S (2010) J Mol Catal A 329:7
Ayala V, Corma A, Iglesias M, Sánchez F (2004) J Mol Catal A 221:201
Karandikar P, Dhanya KC, Deshpande S, Chandwadkar AJ, Sivasanker S, Agashe M (2004) Catal Commun 5:69
Mac Leod TCO, Kirillova MV, Pombeiro AJL, Schiavon MA, Assis MD (2010) Appl Catal A 372:191
Seyedi SM, Sandaroos R, Zohuri GH (2010) Chin Chem Lett 21:1303
Ulaganatha Raja M, Ramesh R (2012) J Organomet Chem 699:5
Ramakrishna D, Bhat BR (2011) Inorg Chem Commun 14:690
Muthu Tamizh M, Mereiter K, Kirchner K, Karvembu R (2012) J Organomet Chem 700:194
Kresge CT, Leonowicz ME, Roth WJ, Vartuli JC, Beck JS (1992) Nature 359:710
Wang XL, Wu GD, Li JP, Zhao N, Wei W, Sun YH (2007) Stud Surf Sci Catal 170:1374
Wang XL, Wu GD, Li JP, Zhao N, Wei W, Sun YH (2007) J Mol Catal A 276:86
Lim MH, Stein A (1999) Chem Mater 11:3285
Sing KSW, Everett DH, Haul RAW, Moscow L, Pierotti RA, Rouquerol T, Siemienewska T (1985) Pure Appl Chem 57:603
Brunel D, Bellocq N, Sutra P, Cauvel A, Laspéras M, Moreau P, Renzo FD, Galarneau A, Fajula F (1998) Coord Chem Rev 180:1085
Wu GD, Wang XL, Li JP, Zhao N, Wei W, Sun YH (2008) Catal Today 131:402
Acknowledgments
The authors acknowledge the financial supports from the National Natural Science Foundation of China (21003073, 21203093), the Program to Cultivate Outstanding Young Key Teachers of Colleges and Universities of Jiangsu Province, the Collegiate Natural Science Fund of Jiangsu Province (12KJD150007) and the Innovation Technology Funding Project of Nanjing Institute of Technology (CKJ2010012).
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Wang, X., Wu, G., Xue, Y. et al. Catalytic Roles of Metal Centers in the Selective Oxidation of Cyclohexanol by Cr(salten) Complexes Immobilized on MCM-41. Catal Lett 143, 219–224 (2013). https://doi.org/10.1007/s10562-012-0934-x
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DOI: https://doi.org/10.1007/s10562-012-0934-x