Oxidation of styrene over polymer- and nonpolymer-anchored Cu(II) and Mn(II) complex catalysts
Sweta Sharma
Department of Chemical Engineering, Indian Institute of Technology Roorkee, Roorkee 247667, Uttarakhand, India
Search for more papers by this authorCorresponding Author
Shishir Sinha
Department of Chemical Engineering, Indian Institute of Technology Roorkee, Roorkee 247667, Uttarakhand, India
Department of Chemical Engineering, Indian Institute of Technology Roorkee, Roorkee 247667, Uttarakhand, India===Search for more papers by this authorPrakash Biswas
Department of Chemical Engineering, Indian Institute of Technology Roorkee, Roorkee 247667, Uttarakhand, India
Search for more papers by this authorMannar R. Maurya
Department of Chemistry, Indian Institute of Technology Roorkee, Roorkee 247667, Uttarakhand, India
Search for more papers by this authorShri Chand
Department of Chemical Engineering, Indian Institute of Technology Roorkee, Roorkee 247667, Uttarakhand, India
Search for more papers by this authorSweta Sharma
Department of Chemical Engineering, Indian Institute of Technology Roorkee, Roorkee 247667, Uttarakhand, India
Search for more papers by this authorCorresponding Author
Shishir Sinha
Department of Chemical Engineering, Indian Institute of Technology Roorkee, Roorkee 247667, Uttarakhand, India
Department of Chemical Engineering, Indian Institute of Technology Roorkee, Roorkee 247667, Uttarakhand, India===Search for more papers by this authorPrakash Biswas
Department of Chemical Engineering, Indian Institute of Technology Roorkee, Roorkee 247667, Uttarakhand, India
Search for more papers by this authorMannar R. Maurya
Department of Chemistry, Indian Institute of Technology Roorkee, Roorkee 247667, Uttarakhand, India
Search for more papers by this authorShri Chand
Department of Chemical Engineering, Indian Institute of Technology Roorkee, Roorkee 247667, Uttarakhand, India
Search for more papers by this authorAbstract
Catalytic oxidation of styrene was investigated over polymer- and nonpolymer-anchored Cu(II) and Mn(II) complex catalysts prepared by schiff base tridentate ligands. The effect of temperature, styrene to H2O2 mole ratio and catalyst amount on the catalytic activity and product selectivity was investigated. Further, the catalysts were characterized by various techniques, such as elemental analysis, atomic absorption spectroscopy (AAS), FTIR, FE-SEM, EDAX, TGA, and UV–vis spectrophotometer. The elemental analysis, EDAX and AAS results confirmed the formation of Cu(II) and Mn(II) complexes, and it was found that the metal loading in the polymer-anchored complex catalysts were in the range of 0.53–3.74 %. FTIR results showed the co-ordination bond formation between the polymer ligands and metal ion. The catalytic data showed that, over all the catalysts, the main reaction products were benzaldehyde, styrene oxide, and benzoic acid. The polymer-anchored complex catalysts were found to be much more active when compared with nonpolymer-anchored catalysts. The maximum conversion of styrene (92.3%) was obtained over PS-[Cu(Hfsal-aepy)Cl] catalyst with benzaldehyde selectivity to 69% at the styrene to H2O2 mole ratio of 1 : 4 at 75°C. Although the PS-[Mn(Hfsal-aepy)Cl] catalyst was less active, it was highly selective to benzaldehyde. © 2012 Wiley Periodicals, Inc. J. Appl. Polym. Sci., 2013
References
- 1 Swern, D. Organic Peroxides; Wiley Interscience: New York, 1971.
- 2 Joseph, T.; Srinivas, D.; Gopinath, C. S.; Halligudi, S. B. Catal. Lett. 2002, 83, 209.
- 3 Hamilton, D. E.; Drago, R. S.; Zombeck, A. J. Am. Chem. Soc. 1987, 109, 374.
- 4 Hulea, V.; Dumitriu, E. Appl. Catal. A Gen. 2004, 277, 99.
- 5 Arends, I. W. C. E.; Sheldon, R. A.; Wallau, M.; Schuchardt, U. Angew. Chem. Int. Ed. Engl. 1997, 36, 1144.
- 6 Rinaldi, R., Schuchardt, U. J. Catal. 2004, 227, 109.
- 7 Rayati, S.; Koliaei, M.; Ashouri, F.; Mohebbi, S.; Wojtczak, A.; Kozakiewicz, A. Appl. Catal. A Gen. 2008, 346, 65.
- 8 Patil, N. S.; Jha, R.; Uphade, B. S.; Bhargava, S. K.; Choudhary, V. R. Appl. Catal. A Gen. 2004, 275, 87.
- 9 Liu, G.; Hou, M.; Song, J.; Zhang, Z.; Wu, T.; Han, B. J. Mol. Catal. A Chem. 2010, 316, 90.
- 10 Meng, X.; Sun, Z.; Wang, R.; Lin, S.; Sun, J.; Yang, M.; Lin, K.; Jiang, D.; Xiao, F.S. Catal. Lett. 2001, 76, 105.
- 11 Lu, X.; Yuan, Y. Appl. Catal. A Gen. 2009, 365, 180.
- 12 Saux, C.; Pierella, L. B. Appl. Catal. A Gen. 2011, 400, 117.
- 13
Shuttleworth, J.;
Allin, S. M.;
Wilson, R. D.;
Nasturica, D.
Synthesis
2000,
8,
1035.
10.1055/s-2000-6310 Google Scholar
- 14 Gupta, K. C.; Sutar, A. K.; Lin, C. C. Coord. Chem. Rev. 2009, 253, 1926.
- 15 De, B. B.; Lohray, B. B.; Sivaram, S.; Dhal, P. K. Macromolecules 1994, 27, 1291.
- 16 Wang, R. M.; Hao, C. J.; He, Y. F.; Xia, C. G.; Wang, J. R. J. Appl. Polym. Sci. 2000, 75, 1138.
- 17 Jain, S.; Reiser, O.; Chem. Sus. Chem. 2008, 1, 534.
- 18 Sherrington, D. C.; Simpson, S. React. Polym. 1993, 19, 13.
- 19 Miller, M. M.; Sherrington, D. C.; Simpson, S. J. Chem. Soc. Perkin Trans. 1994, 2, 2091.
- 20 Miller, M. M.; Sherrington, D. C. J. Catal. 1995, 152, 368.
- 21 Antony, R.; Tembe, G. L.; Ravindranathan, M.; Ram, R. N. Polymer 1998, 39, 4327.
- 22 Antony, R.; Tembe, G. L.; Ravindranathan, M.; Ram, R. N. Eur. Polym. J. 2000, 36, 1579.
- 23 Valodkar, V. B.; Tembe, G. L.; Ravindranathan, M.; Rama, H. S. J. Mol. Catal. A Chem. 2004, 223, 31.
- 24 Chang, Y.; Lv, Y.; Lu, F.; Zha, F.; Lei, Z. J. Mol. Catal. A Chem. 2010, 320, 56.
- 25 Maurya, M. R.; Arya, A.; Kumar, U.; Kumar, A.; Avecilla, F.; Pessoa, J. C. Dalton Trans. 2009, 43, 9555.
- 26 Karmakar, R.; Choudhury, C. R.; Hughes, D. L.; Yap, G. P. A.; Fallah, M. S. E.; Desplanches, C.; Sutter, J. P.; Mitra, S. Inorg. Chim. Acta 2006, 359, 1184.
- 27 Tandon, S. S.; Chander, S.; Thompson, L. K. Inorg. Chim. Acta 2000, 300–302, 683.
- 28 Pearly, S. C.; Sridevi, N.; Yusuff, K. K. M. J. Appl. Polym. Sci. 2007, 105, 997.
- 29 Cazaux, I.; Caz, C.; Eur. Polym. J. 1993, 29, 1615.
- 30 Olason, G.; Sherrington, D. C. React. Funct. Polym. 1999, 42, 163.
- 31 Liu, Z. S.; Rempel, G. L. J. Appl. Polym. Sci. 2008, 108, 3262.
- 32 Maurya, M. R.; Arya, A.; Adao, P.; Pessoa, J. C. Appl. Catal. A Gen. 2008, 351, 239.
- 33 Arroyo, P.; Gil, S.; Munoz, A.; Palanca, P.; Sanchis, J.; Sanz, V. J. Mol. Catal. A Chem. 2000, 160, 403.
- 34 Maurya, M. R.; Kumar, M.; Arya, A. Catal. Commun. 2008, 10, 187.
- 35 Suja, N. R.; Yusuff, K. K. M. J. Appl. Polym. Sci. 2004, 91, 3710.
- 36 Muratua, S.; Mirata, K.; Kidena, K.; Nomura, M. Energy Fuels 2004, 18, 116.
- 37 Syamal, A.; Kale, S. Inorg. Chem. 1979, 18, 992.
- 38 Prasetyanto, E. A.; Park, S. E. Bull. Korean Chem. Soc. 2008, 29, 1033.
- 39 Trakarnpruk, W.; Kanjina, W. Ind. Eng. Chem. Res. 2008, 47, 964.
- 40 Sangeeta, N. R.; Pal, S. Polyhedron 2000, 19, 1593.
- 41 Maurya, M. R.; Kumar, M.; Kumar, U. J. Mol. Catal. A Chem. 2007, 273, 133.
- 42 Hu, J.; Li, K.; Li, W.; Ma, F.; Guo, Y. Appl. Catal. A Gen. 2009, 364, 211.
- 43 Maurya, M. R.; Chandrakar, A. K.; Chand, S. J. Mol. Catal. A Chem. 2007, 278, 12.
- 44 Levenspiel, O. Chemical Reaction Engineering, 3rd ed.; USA, 2006.
- 45 Choudhary, V. R.; Patil, N. S.; Chaudhari, N. K.; Bhargava, S. K. J. Mol. Catal. A Chem. 2005, 227, 2172.
- 46 Maurya, M. R.; Singh, B.; Adao, P.; Avecilla, F.; Pessoa, J. C. Eur. J. Inorg. Chem. 2007, 5720.
- 47 Gupta, K. C.; Sutar, A. K. Coord. Chem. Rev. 2008, 252, 1420.
- 48 Tang, Q.; Zhang, Q.; Wu, H.; Wang, Y. J. Catal. 2005, 230, 384.