High selectivity to p-chloroaniline in the hydrogenation of p-chloronitrobenzene on Ni modified carbon nitride catalyst

doi:10.1016/S1872-2067(15)60904-4

Abstract

Abstract:

A nanocomposite composed of Ni modified carbon nitride was synthesized and used in the hydrogenation of p-chloronitrobenzene. H/D exchange demonstrated that the hydrogen chemisorbed on the surface of this nanocomposite catalyst had a hydrogen atom density of 0.65/nm². It was active for hydrogenation but its activity was inferior to the hydrogen adsorbed on a Ni/Al₂O₃ catalyst. Catalytic tests showed that this catalyst possessed a lower activity than Ni/Al₂O₃ but the selectivity towards p-chloroaniline was above 99.9%. Even at high conversion, the catalyst maintained high selectivity, which was attributed to the unique surface property of the catalyst and the absence of a site for the adsorption of p-chloronitrobenzene, which prevents the C-Cl bond from breaking.

Key words: Hydrogenation, p-Chloronitrobenzene, Carbon nitride, Nickel, Selectivity

Teng Fu, Pei Hu, Tao Wang, Zhen Dong, Nianhua Xue, Luming Peng, Xuefeng Guo, Weiping Ding. High selectivity to p-chloroaniline in the hydrogenation of p-chloronitrobenzene on Ni modified carbon nitride catalyst[J]. Chinese Journal of Catalysis, 2015, 36(11): 2030-2035.

×
share this article

Add to citation manager EndNote|Ris|BibTeX

URL: https://www.cjcatal.com/EN/10.1016/S1872-2067(15)60904-4

https://www.cjcatal.com/EN/Y2015/V36/I11/2030

References

[1] Fan G Y, Zhang L, Fu H Y, Yuan M L, Li R X, Chen H, Li X J. Catal Commun, 2010, 11: 451
[2] Shen J H, Chen Y W. J Mol Catal A, 2007, 273: 265
[3] Baumeister P, Blaser H U, Scherrer W. Stud Surf Sci Catal, 1991, 59: 321
[4] Mo M, Han L, Lv J G, Zhu Y, Peng L M, Guo X F, Ding W P. Chem Commun, 2010, 46: 2268
[5] Liang M H, Wang X D, Liu H Q, Liu H C, Wang Y. J Catal, 2008, 255: 335
[6] Liu H Q, Liang M H, Xiao C, Zheng N, Feng X H, Liu Y, Xie J L, Wang Y. J Mol Catal A, 2009, 308: 79
[7] Cárdenas-Lizana F, Gómez-Quero S, Keane M A. Catal Commun, 2008, 9: 475
[8] Han X X, Chen Q, Zhou R X. J Mol Catal A, 2007, 277: 210
[9] Han X D, Zhou R X, Lai G H, Zheng X M. Catal Today, 2004, 93: 433
[10] Liu A Y, Cohen M L. Science, 1989, 245: 841
[11] Kaner R B, Gilman J J, Tolbert S H. Science, 2005, 308: 1268
[12] Lee J S, Wang X Q, Luo H M, Baker G A, Dai S. J Am Chem Soc, 2009, 131: 4596
[13] Wang E G. Prog Mater Sci, 1997, 41: 241
[14] Wang Y, Wang X C, Antonietti M. Angew Chem Int Ed, 2012, 51: 68
[15] Teter D M, Hemley R J. Science, 1996, 271: 53
[16] Jin X, Balasubramanian V V, Selvan Sahthievel T, Sawant Dhanashri P, Chari Murugulla A, Lu G Q, Vinu A. Angew Chem Int Ed, 2009, 48: 7884
[17] Wang X C, Maeda K, Thomas A, Takanabe K, Xin G, Carlsson J M, Domen K, Antonietti M. Nat Mater, 2009, 8: 76
[18] Zhang J, Grzelczak M, Hou Y D, Maeda K, Domen K, Fu X Z, Antonietti M, Wang X C. Chem Sci, 2012, 3: 443
[19] Cui Y J, Huang J H, Fu X Z, Wang X C. Catal Sci Technol, 2012, 2: 1396
[20] Zheng Y, Jiao Y, Chen J, Liu J, Liang J, Du A J, Zhang W M, Zhu Z H, Smith S C, Jaroniec M, Lu G Q, Qiao S Z. J Am Chem Soc, 2011, 133: 20116
[21] Gong Y T, Zhang P F, Xu X, Li Y, Li H R, Wang Y. J Catal, 2013, 297: 272
[22] Gong Y T, Li M M, Li H R, Wang Y. Green Chem, 2015, 17: 715
[23] Wang Y, Yao J, Li H R, Su D S, Antonietti M. J Am Chem Soc, 2011, 133: 2362
[24] Bian S W, Ma Z, Song W G. J Phys Chem C, 2009, 113: 8668
[25] Li X H, Wang X C, Antonietti M. Chem Sci, 2012, 3: 2170
[26] Xiao P, Zhao Y X, Wang T, Zhan Y Y, Wang H H, Li J L, Thomas A, Zhu J J. Chem Eur J, 2014, 20: 2872
[27] Gong Y T, Li M M, Wang Y. ChemSusChem, 2015, 8: 931
[28] Wang Y, Zhang J S, Wang X C, Antonietti M, Li H R. Angew Chem Int Ed, 2010, 49: 3356
[29] Wang Y, Li H R, Yao J, Wang X C, Antonietti M. Chem Sci, 2011, 2: 446
[30] Wang X C, Chen X F, Thomas A, Fu X Z, Antonietti M. Adv Mater, 2009, 21: 1609
[31] Lin Z Z, Wang X C. Angew Chem Int Ed, 2013, 52: 1735
[32] Zhang Y J, Mori T, Ye J H, Antonietti M. J Am Chem Soc, 2010, 132: 6294
[33] Fu T, Wang M, Cai W M, Cui Y M, Gao F, Peng L M, Chen W, Ding W P. ACS Catal, 2014, 4: 2536
[34] Qiu Y, Gao L. Chem Commun, 2003: 2378
[35] Hellgren N, Guo J H, Luo Y, Såthe C, Agui A, Kashtanov S, Nordgren J, Ågren H, Sundgren J E. Thin Solid Films, 2005, 471: 19
[36] Arrigo R, Havecker M, Schlogl R, Su D S. Chem Commun, 2008: 4891