Abstract
The coupling of 4-aminoantipyrine (4-AAP) with aniline derivatives catalyzed by ruthenium nanoparticles (Rnp) has been studied by UV-Vis spectroscopy in aqueous medium. The rate constant for antipyrilquinoneimine dye formation depends on the nature of the aniline substituent and the pH, ionic strength and temperature of the reaction medium. The maximum rate constant of the dye formation reaction is observed at pH 3.6. Aniline derivatives with electron donating substituents show higher rate constant values than those with electron withdrawing substituents, with increasing rate constant values in the order: N,N-dimethyl aniline > o-toluidine > o-chloroaniline > m-chloroaniline. With pseudo first order kinetics, the total order is 1.0 + 1.0 + 1.0 = 3.0, which includes the orders with respect to amine, 4-AAP and Rnp. Studies on these effects help to complete the kinetic analysis as well as propose the reaction pathway. Furthermore, TEM measurement confirms that the nanoscalar size of the Rnp is 7 nm.
Similar content being viewed by others
References
L.S. Debruin, J.B. Pawliszyn, P.D. Josephy, Chem. Res. Toxicol. 12 (1999) 78.
S. Mishra, V. Singh, A. Jain, K.K. Verma, Analyst 126 (2001) 1663.
E.A. Clark, R. Anliker, O. Hutzinger, The Handbook of Environmental Chemistry Berlin: Springer-Verlag 3A (1980) 181.
D.A. Villalobos, I.D. Buchanan, J. Environ. Eng. Sci. 1 (2002) 65.
M. Oyama, K. Kirihara, Electrochimica. Acta 49 (2004) 3801.
M. Kadar, Z. Nagy, T. Karancsi, G. Farsang, Electrochimica. Acta 46 (2001) 1297.
E. Pramauro, A.B. Prevot, V. Augugliaro, L. Palmisano, Analyst 120 (1995) 237.
E.H. Seymour, N.S. Lawrence, E.L. Beckett, J. Davis, R.G. Compton, Talanta 57 (2002) 233.
E. Brillas, E. Mur, R. Sauleda, L. Sanchez, J. Peral, X. Domenech, J. Casado, Appl. Catal. B: Environ. 16 (1998) 31.
N. Rajendiran, J. Santhanalakshmi, J. Mol. Catal. A: Chem. 245 (2006) 185.
C. Degrand, B. Limoges, A.-M. Martre, B. Schollhorn, Analyst 126 (2001) 887.
W.W. Yu, H. Liu, J. Mol. Catal. A: Chem. 243 (2006) 120.
M. Cerro-Alarcon, A. Maroto-Valiente, I. Rodrýguez-Ramos, A. Guerrero-Ruiz, Carbon 43 (2005) 2711.
A. Spitaleri, P. Pertici, N. Scalera, G. Vitulli, M. Hoang, T.W. Turney, M. Gleria, Inorganica. Chimica. Acta 352 (2003) 61.
A. Roucoux, J. Schulz, H. Patin, Chem. Rev. 102 (2002) 3757.
X. Yan, H. Liu, K.Y. Liew, J. Mater. Chem. 11 (2001) 3387.
F. Bonet, V. Delmas, S. Grugeon, R. Herrera Urbina, P.-Y. Silvert, T.-K. Elhsissen, Nano Str Materials 11 (1999) 1277.
K. Tamaoku, Y. Murao, K. Akiura, Y. Ohkura, Anal. Chem. Acta 136 (1982) 121.
W. Sun, H. Jiang, K. Jiao, J. Chem. Sci. 117 (2005) 317.
S. Premsingh, N.S. Venkataramanan, S. Rajagopal, S.P. Mirza, M. Vairamani, S. Rao, K. Velavan, Inorg. Chem. 43 (2004) 5744.
O.S. Feria, S. Duron, Int. J. Hydrogen Energy 27 (2002) 451.
A.M. Grana, J.M. H-Ramon, R.A. Mosquera, Chem. Phys. Lett 412 (2005) 106.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Kasthuri, J., Santhanalakshmi, J. & Rajendiran, N. Antipyrilquinoneimine dye formation by coupling aniline derivatives with 4-aminoantipyrine in the presence of ruthenium nanoparticles. JICS 5, 436–444 (2008). https://doi.org/10.1007/BF03246000
Received:
Accepted:
Issue Date:
DOI: https://doi.org/10.1007/BF03246000