An environmentally friendly approach to the synthesis of azo dyes based on 2-naphthol using kaolin-SO3H nanoparticles
الموضوعات : Iranian Journal of Catalysis
Abdolhamid Bamoniri
1
(Department of Organic Chemistry, Faculty of Chemistry, University of Kashan, Kashan, I.R. Iran.)
Bi Bi Fatemeh Mirjalili
2
(Department of Chemistry, College of Science, Yazd University, Yazd, I.R. Iran.)
Nahid Yaghmaeiyan-Mahabadi
3
(Department of Organic Chemistry, Faculty of Chemistry, University of Kashan, Kashan, I.R. Iran.)
الکلمات المفتاحية: Nanoparticles, Diazonium salt, 2-Naphthol, Solvent-free, Kaolin-SO3H, Diazo coupling,
ملخص المقالة :
Kaolin-SO3H nanoparticles were prepared via reaction of kaolin and chlorosulfonic acid and characterized by FT-IR, XRD, FESEM, TEM, XRF, EDS, BET and TGA. The activity of this green catalyst was probed by the synthesis of aryl diazonium salts as the starting reactant and then, their diazo coupling with 2-naphthol to form azo dyes in a solvent-free medium at room temperature. The work-up of the reaction was easy, and the catalyst was removed from the products by simple filtration. The reaction proceeded in a short time, easy purification technique, high yields, and was environmentally friendly furthering approaches to green chemistry. The products were characterized by FT-IR and NMR spectroscopy.
[1] A. Bamoniri, B.F. Mirjalili, S. Nazemian, N.Y. Mahabadi, Bulg. Chem. Commun. 46 (2014) 79-84.
[2] B.F. Mirjalili, A. Bamoniri, N. Mohaghegh, Curr. Chem. Lett. 2 (2013) 35-42.
[3] A. Zarei, A.R. Hajipour, L. Khazdooz, B.F. Mirjalili, A.N. Chermahini, Dyes Pigm. 81 (2009) 240-244.
[4] A. Bamoniri, N. Moshtael-Arani, RSC Adv. 5 (2015) 16911-16920.
[5] J. Safaei-ghomi, R. Masoomi, RSC Adv. 5 (2015) 15591-15596.
[6] A. Bamoniri, N.S. Fouladgar, RSC Adv. 5 (2015) 78483-78490.
[7] R. Rani, S. Arya, P. Kilaru, S.M. Sondhi, Green Chem. Lett. Rev. 5 (2012) 545-575
[8] K. Sato, T. Ozu, N. Takenaga, Tetrahedron Lett. 54 (2013) 66-664.
[9] D. Talukdar, A.J. Thakur, Green Chem. Lett. Rev. 6 (2013) 55-61.
[10] S. Kumar, Green Chem. Lett. Rev. 7 (2014) 95-99.
[11] G. Brahmachari, S. Das, RSC Adv. 4 (2014) 7380-7388.
[12] A. Bamoniri, B.F. Mirjalili, N. Moshtael-Arani, Green Chem. Lett. Rev. 7 (2014) 393-403.
[13] P. Gregory, Ink Jet Printing. In: High Technology Applications of Organic Colorants, Plenum: New York, 1991.
[14] R. Steinsträsser, L. Pohl, Angew. Chem. Int. Ed. 12 (1973) 617–630.
[15] Y. Kubo, S. Maeda, S. Tokita, M. Kubo, Nature 382 (1996) 522–524.
[16] R.D. Little, M.G. Venegas, J. Org. Chem. 43 (1978) 2921-2923.
[17] T. Ikeda, O. Tsutumi, Science 268 (1995) 1873-1875.
[18] I.J. Mohammed, A. Mustapha, Molecules 15 (2010) 7498-7508.
[19] A. Aras, M. Albayrak, M. Arikan, K. Sobolev, Clay Miner. 42 (2007) 233-244.
[20] H. Murray, Appl. Clay Sci. 17 (2000) 207-221.
[21] F. Cravero, I. Gonzalez, E. Galan, E. Dominguez, Appl. Clay Sci. 12 (1997) 27-42.
[22] H. Murray, J. Kogel, 2005. Appl. Clay Sci. 27 (2005) 199-206.
[23] J.R. Schupp, E. Fallahi, I.J. Chun, Acta Hort. (ISHS) 636 (2004) 551-556.
[24] B.F. Mirjalili, H. Akrami, Iran. J. Catal. 5 (2015) 129-134.
[25] H. Valizadeh, A. Shomali, Dyes Pigm. 92 (2012) 1138-1143.
[26] Colour Index, Society of Dyers and Colourists, Bradford, U.K. 1971.
[27] B.F. Mirjalili, A. Bamoniri, A. Akbari, Curr. Chem. Lett. 1 (2012) 109-114.
[28] T. Yamada, N. Tanaka, T. Morisawa, M. Nishikuri, A. Kaji, Bull. Chem. Soc. Jpn. 43 (1970) 908-921.
[29] H. Valizadeh, A. Shomali, S. Nourshargh, R. Mohammad Rezaei, Dyes Pigm. 113 (2015) 522-528.
