Abstract
The liquid-phase hydrogenation of m-dinitrobenzene to m-phenylenediamine was studied over silica-supported nickel catalyst. The effects of Ni loading, calcination temperature, and reduction temperature on the physicochemical characteristics and activity of the catalyst were investigated by XRD, TEM, TPR, and activity tests. The results show that the silica-supported nickel catalysts exhibited high catalytic property, which depended on the particle size of Ni and the reduction degree of NiO. The optimal Ni loading, calcination temperature and reduction temperature of the catalyst for m-dinitrobenzene hydrogenation were found to be 20 wt%, 773 K in air and 723 K, respectively. Under this condition, 97.2% conversion of m-dinitrobenzene and 88.9% yield of m-phenylenediamine were obtained at 373 K and 2.6 MPa hydrogen pressure. The particle size of nickel species increased with the increase in Ni loading or calcination temperature. In addition, it was found that the catalyst could not be completely reduced at low reduction temperature, whereas high reduction temperature led to the sintering of Ni.
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References
Bird, A. J. and Thompson, D. T., Catalysis in organic syntheses, Academic Press, New York (1980).
Chang, F.W., Kuo, M. S., Tsay, M. T. and Hsieh, M. C., “Effect of calcination temperature on catalyst reducibility and hydrogenation reactivity in rice husk ash-alumina supported nickel systems,” J. Chem. Technol. Biotechnol., 79, 691 (2004).
Chang, F.W., Kuo, M. S., Tsay, M. T. and Hsieh, M. C., “Hydrogenation of CO2 over nickel catalysts on rice husk ash-alumina prepared by incipient wetness impregnation,” Appl. Catal. A: General, 247, 309 (2003).
Choi, Y. H. and Lee, W.Y., “Effect of Ni loading and calcination temperature on catalyst performance and catalyst deactivation of Ni/SiO2 in the hydrodechlorination of 1,2&dash: Dichloropropane into propylene,” Catal. Lett., 67, 155 (2000).
Diskin, A. M., Cunningham, R. H. and Ormerod, R. M., “The oxidative chemistry of methane over supported nickel catalysts,” Catal. Today, 46, 147 (1998).
Li, H. X., Wang, W. J. and Deng, J. F., “Glucose hydrogenation to sorbitol over a skeletal Ni-P amorphous alloy catalyst (Raney Ni-P),” J. Catal., 191, 257 (2000).
Mäki-Arvela, P., Tiainen, L. P., Neyestanaki, A. K., Sjölm R., Rantakylä, T. K., Laine, E., Salmi, T. and Murzin, D.Y., “Liquid phase hydrogenation of citral: suppression of side reactions,” Appl. Catal. A: General, 237, 181 (2002).
Mizuta, H., Nishimura, T., Wada, M. and Nagata, T., Method for the preparation of pure m-phenylenediamine from crude m-dinitrobenzene, JP Patent 0609551 (1994).
Mizuta, H., Nishimura, T., Wada, M. and Nagata, T., Preparation of highly pure m-phenylenediamine, JP Patent 05331113 (1993).
Pawelec, B., Daza, L., Fierro, J. L.G. and Anderson, J. A., “Regeneration of Ni-USY catalysts used in benzene hydrogenation,” Appl. Catal. A: General, 145, 307 (1996).
Sato, S., Takahashi, R., Sodesawa, T., Nozaki, F., Jin, X. Z., Suzuki, S. and Nakayama, T., “Mass-transfer limitation in mesopores of Ni-MgO catalyst in liquid-phase hydrogenation,” J. Catal., 191, 261 (2000).
Shimazu, K., Tatrno, Y. and Magara, M., Hydrogenation of organic compounds with recyclable lump raney nickel catalyst, JP patent, 09132536 (1997).
Song, C. J., Park, T. J. and Moon, S. H., “Properties of the Ni Kieselguhr catalysts prepared by precipitation method,” Korean J. Chem. Eng., 9, 159 (1992).
Suh, D. J., Park, T. J., Lee, S. H. and Kim, K. L., “Nickel-alumina composite aerogels as liquid-phase hydrogenation catalysts,” J. Non.-Cryst. Solids, 285, 309 (2001).
Takahashi, T., Iwaishi, S., Yanagimoto, Y. and Kai, T., “Hydrogenation of 1-hexenes and 1-octenes over nickel catalyst supported on porous glass prepared from borosilicate glass,” Korean J. Chem. Eng., 14, 459 (1997).
Tobicík, J. and Cerveny, L., “Hydrogenation of alkyl-substituted phenols over nickel and palladium catalysts,” J. Mol. Catal. A: Chemical, 194, 249 (2003).
van de Loosdrecht, J., van der Kraan, A. M., van Dillen, A. J. and Geus, J.W., “Metal-support interaction: titania-supported and silica-supported nickel catalysts,” J. Catal., 170, 217 (1997).
Xu, Z., Li, Y.M., Zhang, J.Y., Chang, L., Zhou, R. Q. and Duan, Z. T., “Bound-state Ni species — a superior form in Ni-based catalyst for CH4/CO2 reforming,” Appl. Catal. A: General, 210, 45 (2001).
Yu, Z.K., Liao, S. J., Xu, Y., Yang, B. and Yu, D. R., “Hydrogenation of nitroaromatics by polymer-anchored bimetallic palladium-ruthenium and palladium-platinum catalysts under mild conditions,” J. Mol. Catal. A: Chem., 120, 247 (1997).
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Liu, Y., Wei, Z. & Zhang, J. Synthesis of m-phenylenediamine from m-dinitrobenzene over silica-supported nickel catalyst. Korean J. Chem. Eng. 23, 902–907 (2006). https://doi.org/10.1007/s11814-006-0006-2
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DOI: https://doi.org/10.1007/s11814-006-0006-2