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Preparation of Salicylic Nitrile through Direct Catalytic Dehydration of Salicylamide with Immobilized Phosphoric Acid as Catalyst
Corresponding Author(s) : Zhao-Sheng Cai
Asian Journal of Chemistry,
Vol. 32 No. 5 (2020): Vol 32 Issue 5
Abstract
Salicylic nitrile was prepared through direct catalytic dehydration of salicylamide under high temperature using immobilized phosphoric acid as catalyst. The catalytic performances of different catalysts were evaluated according to the analytic results of GC-MS, and the feasibility about the preparation of salicylic nitrile by direct catalytic dehydration of salicylamide was investigated according to the composition of product determinated by GC analysis (area nomalization). Experimental results indicated the comprehensive property of silica gel supported phosphoric acid was the best one among all of the catalysts utilized in this study. When the temperature of catalyst bed was 480 ± 10º and silica gel supported phosphoric acid was utilized as catalyst, the conversion ratio of salicylamide was 88.79%, the selectivity to salicylic nitrile was 97.97% and the yields of salicylic nitrile could up to 86.99%. Meanwhile, the experimental results showed the increase of temperature of catalyst bed could result in the increase of the conversation of salicylamide, but much more by-product could be formed when the temperature of catalyst bed was too high.
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References
Z. Huang, Pharm. Ind., 18, 339 (1987).
D. Jie, D. Liao, J. Lou and H. Pi, Fine Chem. Intermed., 37, 25 (2007).
Z. Yong, H. Wei, Y. Zang, W. Yu, C. Ming and W. Yan, Fine Chem. Intermed., 45, 9 (2015).
C. Qiang, W. Liao and Z. Liu, Modern Agrochem., 6, 21 (2007).
J.-H. Noh and J. Kim, J. Org. Chem., 80, 11624 (2015); https://doi.org/10.1021/acs.joc.5b02333
S. Laulhé, S.S. Gori and M.H. Nantz, J. Org. Chem., 77, 9334 (2012); https://doi.org/10.1021/jo301133y
E. Whiting, M.E. Lanning, J.A. Scheenstra and S. Fletcher, J. Org. Chem., 80, 1229 (2015); https://doi.org/10.1021/jo502396u
P. Tamilselvan, Y. Basavaraju, E. Sampathkumar and R. Murugesan, Catal. Commun., 10, 716 (2009); https://doi.org/10.1016/j.catcom.2008.11.025
H. Ehrich, W. Schwieger and K. Jähnisch, Appl. Catal. A Gen., 272, 311 (2004); https://doi.org/10.1016/j.apcata.2004.06.003
S. Ouyang, H. Zhang, D. Li, T. Yu, J. Ye and Z. Zou, J. Phys. Chem. B, 110, 11677 (2006); https://doi.org/10.1021/jp055924t
M.V. Landau, M.L. Kaliya and M. Herskowitz, Appl. Catal. A Gen., 208, 21 (2001); https://doi.org/10.1016/S0926-860X(00)00700-6
W. Kleemiss. Process for the Preparation of Hydroybenzonitrile, US 6248917B1 (2001).
J.-J. Deng, T. Lu and S. Huang, Shanghai Chem. Ind., 29, 24 (2009).
W. He, J. Guo and Y. Zhou, Shanghai Chem. Ind., 37, 10 (2012).
R. Möller, M. Gómez, K. Einmayr, J. Hildbrand, H.-G. Eeben and H.-P. Krimmer, Method for Producing Amino- or Hydroxybenzonitriles, US Patent 7629486B2 (2009)
X. Guo, C. Liu, X. Xu, X. Huang and H. Li, Fine Chem. Intermed., 49,16 (2019).
E. Chen, L. Wei, X. Zhang, X. Liu, W. Feng, H. Yan and E. Yan-peng, Agrochemicals, 57, 870 (2018).
Z. Shi, N. Wang, D.-X. Hou and J.-D. Huang, Dyestuffs and Coloration, 56, 23 (2019).
L. Wang, Z. Song, G. Wang, D. Xu and B. Hua, Zhejiang Chem. Ind.,43, 33 (2012).
Y. Ye, E. Wu, C. Yu, F. Yu and Y. Xue, Agrochemicals, 50, 730 (2011).