Hydrochloric acid immobilized on nano‐titanium dioxide: a novel and efficient nanocatalyst for the synthesis of tetrahydrobenzo[b]pyrans

Document Type : Original Article

Authors

1 Faculty of Chemistry, Semnan University, Semnan, Iran

2 Semnan University

Abstract

Hydrochloric acid was immobilized onto the surface of amine functionalized nano‐titania. For this purpose, 2,4‐toluene diisocyanate (TDI) as a bi‐functional covalent linker was grafted onto a nano‐titania and next, the unreacted isocyanate groups were then reduced with water and finally, the prepared amine group in the previous step was reacted with hydrochloric acid in order to producing ammonium chloride salt. This efficient nanocatalyst was evaluated in the synthesis of tetrahydrobenzo[b]pyrans, which affords high yields (67-93%) and short reaction time (15-30 min). The synthesized nanocatalyst was characterized by Fourier transform infrared spectroscopy, X-ray diffraction, field emission scanning electron microscopy, thermogravimetric analysis, and Mohr method titration.

Keywords

Main Subjects


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[1] A.T. Bell, Science, 299 (2003) 1688.
[2] P. Gupta, S. Paul, Catalysis Today, 236 (2014) 153.
[3] J.H. Clark, Accounts of chemical research, 35 (2002) 791.
[4] T. Okuhara, Chemical Reviews, 102 (2002) 3641.
[5] R.A. Sheldon, R.S. Downing, Applied Catalysis A: General, 189 (1999) 163.
[6] J. Heveling, Journal of Chemical Education, 89 (2012) 1530.
[7] A. Corma, H. Garcia, Advanced Synthesis & Catalysis, 348 (2006) 1391.
[8] F. Cozzi, Advanced Synthesis & Catalysis, 348 (2006) 1367.
[9] V. Polshettiwar, R.S. Varma, Green Chemistry, 12 (2010) 743.
[10] R. Schlögl, S.B. Abd Hamid, Angewandte Chemie International Edition, 43 (2004) 1628.
[11] R.N. Baig, R.S. Varma, Green Chemistry, 15 (2013) 398.
[12] A. Ying, S. Liu, Z. Li, G. Chen, J. Yang, H. Yan, S. Xu, Advanced Synthesis & Catalysis, 358 (2016) 2116.
[13] A. Ying, S. Liu, Y. Ni, F. Qiu, S. Xu, W. Tang, Catalysis Science & Technology, 4 (2014) 2115.
[14] M. Dabiri, M. Bahramnejad, M. Baghbanzadeh, Tetrahedron, 65 (2009) 9443.
[15] B. Nozière, P. Dziedzic, A. Córdova, Physical Chemistry Chemical Physics, 12 (2010) 3864.
[16] D.W. Brown, A.J. Floyd, R.G. Kinsman, Y. Ali, Journal of chemical technology and biotechnology, 32 (1982) 920.
[17] X. Cao, S.P. Teong, D. Wu, G. Yi, H. Su, Y. Zhang, Green Chemistry, 17 (2015) 2348.
[18] S.P. Teong, G. Yi, X. Cao, Y. Zhang, ChemSusChem, 7 (2014) 2120.
[19] T. Shamsi, A. Amoozadeh, S.M. Sajjadi, E. Tabrizian, Applied Organometallic Chemistry, (2016).
[20] E. Tabrizian, A. Amoozadeh, Catalysis Science & Technology, (2016) 6267.
[21] E. Tabrizian, A. Amoozadeh, RSC Advances, 6 (2016) 96606.
[22] E. Tabrizian, A. Amoozadeh, S. Rahmani, RSC Advances, 6 (2016) 21854.
[23] E. Tabrizian, A. Amoozadeh, T. Shamsi, Reaction Kinetics, Mechanisms and Catalysis, 119 (2016) 245.
[24] A. Amoozadeh, S. Golian, S. Rahmani, RSC Advances, 5 (2015) 45974.
[25] A. Amoozadeh, S. Rahmani, Journal of Molecular Catalysis A: Chemical, 396 (2015) 96.
[26] A. Amoozadeh, S. Rahmani, M. Bitaraf, F.B. Abadi, E. Tabrizian, New Journal of Chemistry, 40 (2016) 770.
[27] S. Rahmani, A. Amoozadeh, E. Kolvari, Catalysis Communications, 56 (2014) 184.
[28] J. Chen, M. Liu, L. Zhang, J. Zhang, L. Jin, Water Research, 37 (2003) 3815.
[29] B. Ou, D. Li, Q. Liu, Z. Zhou, B. Liao, Materials Chemistry and Physics, 135 (2012) 1104.
[30] S.M. Alahmadi, S. Mohamad, M. Jamil Maah, Advances in Materials Science and Engineering, 2013 (2013).
[31] Y.S. Chun, K. Ha, Y.-J. Lee, J.S. Lee, H.S. Kim, Y.S. Park, K.B. Yoon, Chemical Communications, (2002) 1846.
[32] M. Yang, Y. Gao, J. He, H. Li, Express Polymer Letters, 1 (2007) 433.
[33] N. Venkatachalam, M. Palanichamy, V. Murugesan, Journal of Molecular Catalysis A: Chemical, 273 (2007) 177.
[34] F. Solymosi, J. Raskó, Journal of Catalysis, 63 (1980) 217.
[35] D.L. Pavia, G.M. Lampman, G.S. Kriz, J.A. Vyvyan, Cengage Learning, 2008.
[36] L. Zhang, Q. Jin, L. Shan, Y. Liu, X. Wang, J. Huang, Applied Clay Science, 47 (2010) 229.
[37] S.V. Atghia, S.S. Beigbaghlou, Journal of Nanostructure in Chemistry, 3 (2013) 1.
[38] C. Dubois, M. Rajabian, D. Rodrigue, Polymer Engineering & Science, 46 (2006) 360.
[39] H.-J. Song, Z.-Z. Zhang, X.-h. Men, Surface and Coatings Technology, 201 (2006) 3767.
[40] S.S. Pourpanah, S.M. Habibi-Khorassani, M. Shahraki, Chinese Journal of Catalysis, 36 (2015) 757.
[41] F.N. Sadeh, M.T. Maghsoodlou, N. Hazeri, M. Kangani, Research on Chemical Intermediates, 41 (2015) 5907.
[42] Y.B. Wagh, Y.A. Tayade, S.A. Padvi, B.S. Patil, N.B. Patil, D.S. Dalal, Chinese Chemical Letters, 26 (2015) 1273.
[43] M. Moghaddas, A. Davoodnia, Research on Chemical Intermediates, 41 (2015) 4373.
[44] F. Shirini, M. Abedini, S. Zarrabzadeh, M. Seddighi, Journal of the Iranian Chemical Society, 12 (2015) 2105.
[45] B. Maleki, S.S. Ashrafi, RSC Advances, 4 (2014) 42873.
[46] J.K. Rajput, G. Kaur, Catalysis Science & Technology, 4 (2014) 142.
[47] D. Fang, H.B. Zhang, Z.L. Liu, Journal of Heterocyclic Chemistry, 47 (2010) 63.
[48] M. Abdollahi-Alibeik, F. Nezampour, Reaction Kinetics, Mechanisms and Catalysis, 108 (2013) 213.
[49] A. Alizadeh, M.M. Khodaei, M. Beygzadeh, D. Kordestani, M. Feyzi, Bulletin of the Korean Chemical Society, 33 (2012) 2546.