CiteScore: 1.9     h-index: 21

Document Type : Original Research Article

Authors

Department of Chemistry, Osmania University, Hyderabad (T.S)-500007 India

Abstract

A green protocol is described for sulfonation of aromatic compounds that has been accomplished using sodium bisulfite (NaHSO3) in the presence of reusable green heterogeneous SiO2/HClO4 and SiO2/KHSO4 (Silica-supported HClO4 and KHSO4 catalysts) under conventional and solvent-free microwave irradiation.  The reactions afforded very good yields of products within 3 to 5 hour under conventional conditions. However, the reaction times in microwave-assisted protocol are drastically reduced to 3 to 5 minutes (from 3 to 5 hour under conventional conditions) followed by increasing product yields. Moreover, the developed silica-supported catalysts could be  recycled for at least three to four times.

Graphical Abstract

Silica-supported HClO4 and KHSO4 as reusable green catalysts for sulfonation of aromatic compounds under solvent-free conditions

Keywords

Main Subjects

[1]. Gilbert E.E., Sulfonation and Related Reactions, Wiley, NY, 1965
[2]. Cerfontain H.J.A., Schaasberg Z.R.H., Coombes R.G., Hadjigeorgion P., Tucker G.P.  J. Chem. Soc. Perkin Trans., 1985, 2:659
[3]. Gilbert E.E. Chem. Rev., 1962, 62:549
[4]. Cerfontain H.  Mechanistic Aspects in Aromatic Sulfonation and Desulfonation, Interscience Publishers, New York, 1965
[5]. Sülzle D., Verhoeven M., Terlouw J.K., Schwarz H. Angew. Chem. Int. Ed. Engl., 1988, 27:1533
[6]. Umemoto T., Tomozwaza G.J. Org. Chem., 1995, 60:6563
[7]. Cerfontain H., Lambrechts H.J.A., Schaasberg Z.R.H., Coombes R.G., Hadjigeorgion P., Tucker G.P.J., Chem. Soc. Perkin Trans., 1985, 2:659
[8]. Wuts P.G.M., Wilson K.E. Synthesis, 1998, 1593
[9]. Corby B.W., Gary A.D., Meaney P.J., Falvey M., Lawrence G.P., Smyth T.P.J. Chem. Res. Synop., 2002, 7:326
[10]. Bochkareva T.P., Yakovlev I.P., Passet B.V., Sheiko M.A.J. Org. Chem., 1989, 25:1346
[11]. Mirjalili B.F., Zolfigol M.A., Bamoniri A.H., Zarei A. Phosphorus, Sulfur Silicon Relat. Elem., 2003, 178:1845
[12]. Smith M.B., March J. Advanced Organic Chemistry: Reactions, Mechanisms, and Structure (6th ed.), New York: Wiley-Interscience, 2007
[13]. Suter C.M., Weston A.W. Org. React., Doi: 10.1002/0471264180.or003.04
[14]. Breton G.W.J. Org. Chem., 1997, 62:8952
[15]. Ramesh C., Ravindranath N.,  Das B.J. Org. Chem., 2003, 68:7101
[16]. Sharma U., Katoch D., Sood S., Kumar N., Singh B., Thakur A., Gulati A. Indian J. Chem., 2013, 52B:1431
[17]. Sheldon R.A., Arends I.W.C.E., Hanefeld U. Green Chemistry and Catalysis, Doi: 10.1002/9783527611003.ch2
[18]. Kaur M., Sharma S., Bedi P.M.S. Chin. J. Cat., 2015, 36:520
[19]. Baghernejad B. European J. Chem., 2012, 3:125
[20]. Wang B., Gu Y., Luo C., Yang T., Yang L., Suo J. Tetrahedron Lett., 2004, 45:3369
[21]. Wilson K., Clark J.H., Pure Appl. Chem., 2000, 72:1313
[22]. Siddiqui Z.N., Farooq F. J. Mol. Cat. A: Chemical., 2012, 363-364:451
[23]. Siddiqui Z.N. Arabian J. Chem., Doi: org/10.1016/j.arabjc.2015.06.013
[24]. Hemanth Sriram Y., Fatima T., Satish Kumar M., Rajanna K.C., Venkateswarlu M., Sai Sudhakar M., Raju R.M., Iran. Chem. Commun., 2017, 5:352 
[25]. Anastas P., Warner J. In Green Chemistry: Theory and Practice; Oxford University Press: New York, 1998
[26]. Anastas P.T., Kirchhoff M.M. Acc. Chem. Res., 2002, 35:686
[27]. Lidström P., Tierney J., Wathey B., Westman J. Tetrahedron., 2001, 5:9225
[28]. Varma R.S. Green Chem., 1999, 1:43.
[29]. Vivek P., Varma R.S. Chem. Res., 2008, 41:629
[30]. Oliver Kappe C.  Angew. Chem. Int. Ed., 2004, 43:6250
[31]. Oliver Kappe C., Pieber B., Dallinger D. Angew. Chem. Int. Ed., 2013, 52:1088