Smectite Clays: Green, Heterogeneous and Recyclable catalyst in Solvent-free Synthesis of Triaryl Cyanurates Using Grinding Method

Document Type : Original Article

Authors

Abstract

Triaryl cyanurates are important chemicals used in various fields such as polymer, dyes and pharmaceuticals. In this research, synthesis of some triaryl cyanurates derivatives on smectite clays such as  montmorillonites  K10 and  KSF,  hectorite and bentonite as green, recyclable and heterogeneous catalysts using grinding method without any organic solvents has been evaluated. This present method is superior since it is eco-friendly, advantageous over previously described methods in yield, requires no special apparatus, there is simplicity of operation, and is non-hazardous, simple and convenient. In addition, the simple experimental and product isolation procedures combined with the easy recovery and reuse of these worthwhile natural clays play an important role in development of the clean and environmentally friendly strategy in this new and benign method.

Keywords


[1] A. Ningawa, M. Kawazoe, H. Mastuda, Makromol. Chem. 180 (1979) 2123.
[2] a) H. Klinkenberg, E. Peterson, W. Sehmidt, Ger. Offen. (1975)  2356771; b) Dynamit  Nobel, AG, C. A. 83 (1975) 115984.
[3] A. Furushita, A. Sakata, A. Sasaki, Japanese Pat. 740 (1974) 7574; Unitika Ltd, C. A. 81 (1974) 122598.
[4] a) J. H. A. Row, British. Pat. (1968) 1102012; British Peteroleurn Co. Ltd., C. A. 69 (1968) 36184. b).
[5] Z. Rostami, N. Sarmasti, A. Khazaei, M. A. Zolfigol, J. Yousefiseyf, J. Appl. Chem. 8 (2013) 11.
[6] T. Hosai, H. Tsugawa, (Nippon Kayaku Co Ltd) Jpn Kokai Tokkyo Koho JP 02,293,181(90,293,181); Chem. Abstr. 115 (1991) 146695.
[7] K. Kamamoto, J. Hibino, (Untika Ltd) Jpn Kokai Tokkyo Koho JP 04,153,315 (92,153,35); Chem. Abstr. 117 )1992( 152716.
[8] Y. Tamura, (Mitsubishi Petrochemical Co. Ltd) Jpn Kokai Tokkyo Koho JP 60,285,256 (85,258,256) Chem. Abstr. 105 (1986) 44019.
[9] M. Arai, Y. Tsuda, (Kancho. Ltd) Jpn Kokai Tokkyo Koho JP 06,287,806 (94,287,806) Chem Abstr, 122 (1995) 293314.
[10] a) E. Grigat, R. Puetter, German Pat. (1964) 1183507; b) Farbenfabriken Bayer A. G, C. A. 62 (1965) 14705.
[11] F. C. Schaefer, J. T. Thurston, J. R. Dubley,  J. Am. Chem. Soc. 73 (1951) 2990.
[12] a) F. J. Allan, G. G. Allan, T. Mittila, P. Mauranen, Acta Chim. Scand. 23 (1969) 1903. b) A. D. Sagar, D. S. Patil, B. P. Bandgar, Synth. Commun. 30(10) (2000) 1719.
[13] a)  J. P. Zimmermann, French Pat. (1969) 1566675; b) Societe d’ Etudes Chimiques Pour I’Industrie et I’ Aqriculture, C. A. 72 (1970) 79107.
[14] M. T. Thorat, R. B. Mane, M. H. Jagadale, M. M. Salunkhe, P. P. Wadgaonkar, Eu. Polym. J. 24 (1988) 399.
[15] B. P. Kavitake, S.V. Patil, M. M. Salunkhe, P. P. Wadgaonkar, Bull. Soc. Chim. Belg. 104 (1995) 675.
[16] M. Kalmutzki, M. Ströbele, F. Wackenhut, A. J. Meixner, H. -J. Meyer,  Inorg. Chem. 53 (2014) 12540.
[17] K. Yamada, H. Fujita, M. Kitamura, M. Kunishima. Synthesis 45 (2013) 2989.
[18] S. T. Asundaria, V. B. Patel, K. C. Patel, Russ. J. Gen. Chem. 81 (2011) 2183.
[19] a) R. Ballini, G. Bosica, R. Maggi, M. Ricciutelli, P. Righi, G. Sartori, R. Sartorio,  Green Chem. 3 (2001) 178; b) G. Sartori, F. Bigi, R. Maggi, A. Mazzacani, G. Oppici, Eur. J. Org. Chem. (2001) 2513.
[20] a) P. Berteau, B. Delmon, Catal. Today 5 (1989) 121; b) S. Brunauer, P. H. Emmett, E. Teller, J. Am. Chem. Soc. 60 (1938) 309.
[21] a) J. H. A. Row, British. Pat. 1968, 1102012; b) British Peteroleurn Co. Ltd., C. A. 69 (1968) 36184. 
[22] E. Grigat, R. Puetter, German Pat. (1964) 1183507; Farbenfabriken Bayer A. G, C. A. 62 (1965) 14705.
[23] F. C. Schaefer, J. T. Thurston, J. R. Dubley, J. Am. Chem. Soc. 73 (1951) 2990.
[24] M. T. Thorat, R. B. Mane, M. H. Jagdale, M. M. Salunkhe, P. P. Wadgaonkar, Eur. Polym. J. 24 (1988) 399.
[25] A. D. Sagar, D. S. Patil, B. P. Bandgar, Synth. Commun. 30 (2000) 1719.
[26] N. D. Ghatge, S. D. Yadav, Makromol, Chem. 124 (1969) 167