Commenced in January 2007
Frequency: Monthly
Edition: International
Paper Count: 32726
Comparative Kinetic Study on Alkylation of p-cresol with Tert-butyl Alcohol using Different SO3-H Functionalized Ionic Liquid Catalysts

Authors: Pandian Elavarasan, Kishore Kondamudi, Sreedevi Upadhyayula


Ionic liquids are well known as green solvents, reaction media and catalysis. Here, three different sulfonic acid functional ionic liquids prepared in the laboratory are used as catalysts in alkylation of p-cresol with tert-butyl alcohol. The kinetics on each of the catalysts was compared and a kinetic model was developed based on the product distribution over these catalysts. The kinetic parameters were estimated using Marquadt's algorithm to minimize the error function. The Arrhenius plots show a curvature which is best interpreted by the extended Arrhenius equation.

Keywords: Alkylation, p-cresol, tert-butyl alcohol, kinetics, activation parameter, extended Arrhenius equation.

Digital Object Identifier (DOI):

Procedia APA BibTeX Chicago EndNote Harvard JSON MLA RIS XML ISO 690 PDF Downloads 2382


[1] G.A. Olah, "Friedel-Crafts and Related Reactions," 1st ed., Interscience Publishers, New York, 1963.
[2] A. Knopp, L.A. Pilato, Phenolic Resins, Chemistry, Applications and Performance-Future directions, 1st ed., Springer, Berlin, 1985.
[3] J. Pospisil, "Mechanistic action of phenolic antioxidants in polymersÔÇöA review," Polym. Degrad. Stab., vol. 20, pp. 181-202 (3-4), 1988.
[4] J. Murphy, "Additives for plastics handbook," 2ed., Elsevier, Amsterdam, 2001.
[5] R.D. Kirk and D.F. Othmer, "Kirk-Othmer Encyclopedia of Chemical Technology," vol. 2, 3rd, Wiley Interscience, New York, pp. 57-70, 1978.
[6] A.A. Carlton, Alkylation of phenol with t-butyl alcohol in the presence of perchloric acid, J. Org. Chem., vol. 13 (1), pp. 120-122, Jan. 1948.
[7] M.A. Harmer and Q. Sen, Solid acid catalysis using ion-exchange resins, Appl. Catal. A., vol. 221(1-2), pp. 45-62, Nov. 2001.
[8] M. Selvaraj and S. Kawi, t-Butylation of p-cresol with t-butyl alcohol over mesoporous Al-MCM-41 molecular sieves, Micro. Meso. Mater., vol. 98 (1-3), pp.143-149, Jan 2007.
[9] G.D. Yadav and T.S. Thorat, Kinetics of Alkylation of p-Cresol with Isobutylene Catalyzed by Sulfated Zirconia, Ind. Eng. Chem. Res., vol. 35 (3), pp. 721-731, Mar. 1996.
[10] K. Zhang, H. Zhang, G. Xiang, D. Xu, S. Liu and H. Li, Alkylation of phenol with tert-butyl alcohol catalyzed by large pore zeolites, Appl.Catal. A., vol. 207, pp.183-190, Feb. 2001.
[11] K. Usha Nandhini, B. Arabindoo, M. Palanichamy and V. Murugesan, t- Butylation of phenol over mesoporous aluminophosphate and heteropolyacid supported aluminophosphate molecular sieves, J. Mol. Catal. A., vol. 223, pp. 201-210, Dec. 2004.
[12] T. Welton, Room-temperature ionic liquids. Solvents for synthesis and catalysis, Chem. Rev., vol. 99 (8), pp. 2071-2083, Aug. 1999.
[13] R. Sheldon, Catalytic reactions in ionic liquids, Chem. Commun., vol. 1, pp. 2399-2407, 2001.
[14] K. Kondamudi, P. Elavarasan, P. J. Dyson, S. Upadhyayula, Alkylation of p-cresol with tert-butyl alcohol using benign Bronsted acidic ionic liquid catalyst, J. Mol. Catal. A., DOI:10.1016/j.molcata.2010.01.016
[15] P. Elavarasan, K. Kondamudi, S. Upadhyayula, Statistical optimization of process variables in batch alkylation of p-cresol with tert-butyl alcohol using ionic liquid catalyst by response surface methodology, Chem. Eng. J., vol. 155 (1-2), pp.355-360, Dec. 2009.
[16] X. Liu, J. Zhou, X. Guo, M. Lin, X. Ma, C. Song and C. wang, SO3HFunctionalized Ionic Liquids for Selective Alkylation of p-Cresol with tert-Butanol, Ind. Eng. Chem. Res., vol. 47 (1), pp. 5298-5303, Jun. 2008.
[17] M. Yuceer, I. Atasoy and R. Berber, A software for parameter estimation in dynamic models, Braz. J. Chem. Eng., vol. 25 (4), pp. 813 - 821, Oct. 2008.
[18] F. G. Helfferich, Kinetics of multistep reactions, 2nd ed., Elsevier, Amsterdam, pp. 429-444, 2004.
[19] S. Wold and P. Ahlberg, Evaluation of Activation Parameters for a First Order Reaction from One Kinetic Experiment. Theory, Numerical Methods, and Computer Program, Acta. Chem. Scand., vol. 24, pp. 618- 632, 1970.