Abstract
The preparation, characterization, and catalytic properties of acid treated clay (ATC) are reported. ATC has been characterized by XRD (basal spacing, 14.82 Å), specific surface area (66 m2/g), pore volume and pore width using BET method, UV–Vis DRS, TGA, SEM, and surface acidity by TPD of NH3. The activity of was investigated by the reaction of benzil with o-phenylene diamine. Among the catalysts, ATC was found to be more active. The reaction of various substituted o-phenylenediamines with benzil was studied on ATC to obtain corresponding quinoxalines in good yields. The regeneration and reusability of ATC has also been investigated.
Similar content being viewed by others
References
B. Vijayakumar, Synlett 2, 388 (2004)
G. Nagendrappa, Appl. Clay Sci. 53, 106 (2011)
A. Vaccari, Appl. Clay Sci. 14, 161 (1999)
B. Vijayakumar, G. Nagendrappa, B.S. Jai Prakash, Catal. Lett. 128, 183 (2009)
N. Kaur, D. Kishore, J. Chem. Pharm. Res. 4, 991 (2012)
C.N. Rhodes, D.R. Brown, J. Chem. Soc. Faraday 91, 1031 (1995)
M. Frenkel, Clays Clay Miner. 22, 435 (1974)
E.L. Foletto, G.C. Colazzo, C. Volzone, L.M. Porto, Braz. J. Chem. Eng. 28, 169 (2011)
P. Komadel, M. Janek, J. Madejova, A. Weekes, C. Breen, J. Chem. Soc. Faraday Trans. 93, 4207 (1997)
W.P. Gates, J.S. Anderson, M.D. Raven, G.J. Churchman, Appl. Clay Sci. 20, 189 (2002)
M.P. Hart, D.R. Brown, J. Mol. Catal. A Chem. 212, 315 (2004)
E.L. Foletto, D.S. Paz, A. Gündel, Appl. Clay Sci. 83–84, 63 (2013)
D. Woumfo, R. Kamga, F. Figueras, D. Njopwouo, Appl. Clay Sci. 37, 149 (2007)
T. Yang, X.-D. Wen, J. Li, L. Yang, Appl. Surf. Sci. 252, 6154 (2006)
M.I. Zaki, M. Abdel-Khalik, G.M. Habashy, Colloids Surf. 17, 241 (1986)
R. Mokaya, W. Jones, M.E. Davies, M.E. Whittle, J. Solid State Chem. 111, 157 (1994)
D.R. Brown, C.N. Rhodes, Catal. Lett. 45, 35 (1997)
G.E. Christidis, P.W. Scott, A.C. Dunham, Appl. Clay Sci. 12, 329 (1997)
D. Doulia, Ch. Leodopoulos, K. Gimouhopoulos, F. Rigas, J. Colloid Interface Sci. 340, 131 (2009)
B. Tyagi, C.D. Chudasama, R.V. Jasra, Appl. Clay Sci. 31, 16 (2006)
M.M. Kashani Motlagh, A.A. Youzbashi, Z. Amiri Rigi, Iran J. Mater. Sci. Eng. 8(4), 50 (2011)
J. Temuujin, T. Jadambaa, G. Burmaa, S. Erdenechimeg, J. Amarsanaa, K.J.D. MacKenzie, Ceram. Int. 30, 251 (2004)
R.O. Ajemba, O.D. Onukwuli, Int. J. Eng. Trans. B 26, 495 (2013)
N. Bes̨ün, F. Özkan, G. Gündüz, Appl. Catal. A Gen. 224, 285 (2002)
T. Alemdaroglu, G. Akkus, M. Onal, Y. Sarikaya, Turk. J. Chem. 27, 675 (2003)
L.E. Seitz, W.J. Suling, R.C. Reynolds, J. Med. Chem. 45, 5604 (2002)
C.W. Lindsley, Z. Zhao, W.H. Leister, R.G. Robinson, S.F. Barnett, D. Defeo-Jones, R.E. Jones, G.D. Hartman, J.R. Huff, H.E. Huber, M.E. Duggan, Bioorg. Med. Chem. Lett. 15, 761 (2005)
M. Loriga, S. Piras, P. Sanna, G. Paglietti, Farmaco 52, 157 (1997)
Y.B. Kim, Y.H. Kim, J.Y. Park, S.K. Kim, Bioorg. Med. Chem. Lett. 14, 541 (2004)
N.D. Sonawane, D.W. Rangnekar, J. Heterocycl. Chem. 39, 303 (2002)
S. Dailey, J.W. Feast, R.J. Peace, I.C. Sage, S. Till, E.L. Wood, J. Mater. Chem. 11, 2238 (2001)
J.-J. Cai, J.-P. Zou, X.-Q. Pan, W. Zhang, Tetrahedron Lett. 49, 7386 (2008)
T.M. Potewar, S.A. Ingale, K.V. Srinivasan, Synth. Commun. 38, 3601 (2008)
B.C. Raju, N.D. Theja, J.A. Kumar, Synth. Commun. 39, 175 (2008)
Tai-kun Huang, Rui Wang, Lin Shi, Lu Xiao-xia, Catal. Commun. 9, 1143 (2008)
Y.S. Beheshtiha, M.M. Heravi, M. Saeedi, N. Karimi, M. Zakeri, N. Tavakoli-Hossieni, Synth. Commun. 40, 1216 (2010)
J.-Y. Liu, J. Liu, J.-D. Wang, D.-Q. Jiao, H.-W. Liu, Synth. Commun. 40, 2047 (2010)
Y. Venkateswarlu, P. Leelavathi, Lett. Org. Chem. 7, 208 (2010)
T. Huang, D. Jiang, J. Chen, W. Gao, J. Ding, H. Wu, Synth. Commun. 41, 3334 (2011)
M. Jafarpour, A. Rezaeifard, M. Heidari, Lett. Org. Chem. 8, 202 (2011)
A. Dhakshinamoorthy, K. Kanagaraj, K. Pitchumani, Tetrahedron Lett. 52, 69 (2011)
M. Jafarpour, A. Rezaeifard, M. Danehchin, Appl. Catal. A Gen. 394, 48 (2011)
A. Venkat Narsaiah, J. Kranthi Kumar, Synth. Commun. 42, 883 (2012)
B. Vijayakumar, C.R. Reddy, P. Iyengar, G. Nagendrappa, B.S.J. Prakash, Indian J. Chem. Technol. 12, 316 (2005)
R. Mokaya, W. Jones, J. Catal. 153, 76 (1995)
B. Vijayakumar, Synthesis of industrially important esters using eco-friendly clay catalysts, Ph.D. Thesis, Visvesvaraya Technological University, Belgaum, India, 2005
O.M. Sadek, W.K. Mekhamer, Thermochim. Acta 363, 47 (2000)
K.S.W. Sing, D.H. Everett, R.A.W. Haul, L. Moscou, R.A. Pierotti, J. Rouquerol, T. Siemieniewska, Pure Appl. Chem. 57, 603 (1985)
B. Vijayakumar, G. Ranga, Rao. J. Porous Mater. 19, 233 (2012)
Acknowledgments
This work is funded by the Department of Science and Technology, New Delhi, India, under Fast Track Scheme for Young Scientists (Project No. SR/FTP/CS-11/2006). The author is grateful to Prof. G. Ranga Rao, Department of Chemistry, IIT Madras, Chennai, India for his support and encouragement. Thanks are also due to the Sophisticated Analytical Instrument Facility, Indian Institute of Technology Madras for IR, HRMS, 1H and 13C NMR spectra.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Badathala, V. Acid treated clays: preparation, characterization and catalytic activity for synthesis of quinoxaline derivatives. J Porous Mater 22, 779–786 (2015). https://doi.org/10.1007/s10934-015-9951-7
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10934-015-9951-7