The Kinetic Study of Oleamide Synthesis: Effect of Oleic Acid Molar Ratio, Temperature and Catalyst Concentration

Document Type : Research Paper


Chemical Process Design Research Group, ACECR, Faculty of Engineering, University of Tehran, P.O. Box 1417943851, Tehran, Iran


Oleamide is amide derivative of oleic acid that is frequently used as slip agent in polymer industry. The present study explores the kinetic of oleamide synthesis by ammonolysis reaction between oleic acid and urea instead of ammonia gas at atmospheric pressure in the presence of AlCl3 catalyst. The effect of oleic acid : urea molar ratio, temperature and catalyst concentration on the reaction kinetic was investigated and reaction rate constants were calculated. At low molar ratio of oleic acid:urea (i.e. up to 1:2), the reaction followed an overall second order kinetic and at higher molar ratio (i.e. 1:4 and 1:5), the pseudo first order dependence of rate respect to oleic acid was dominant at three examined temperatures and catalyst concentrations. The values of rate constant were increased by increasing the temperature and urea as well as AlCl3 concentration in which the highest amount was attributed to the operational condition of oleic acid: urea molar ratio of 1:4, temperature of 200 °C and AlCl3 catalyst concentration of 1 wt% that was selected as optimum condition for oleamide synthesis.


[1] F. Coelho, L. Vieira, R. Benavides, M. Paula, A.M. Bernardin, R.F. Magnago, L. Silva, J. Polym. Process. Soc., 30, 574 (2015).
[2] I. Quijada-Garrido, J.M. Barrales-Rienda, J.M. Pereña, G.Frutos, Polymer., 38, 5125 (1997).
[3] M. Tolinski, Additives for Polyolefins: Getting the Most out of Polypropylene, Polyethylene and TPO, William Andrew, USA (2015).
[4] J. Markarian, Plastic. Addit. Compound., 9, 32 (2007).
[5] H. J. Harwood, J. Am. Oil Chem. Soc., 31, 559 (1954).
[6] K.S. Markley, Fatty Acids, Interscience Publishers, New York (1964).
[7] P. Patel, N. Savargaonkar, Plast. Eng., 63, 48 (2007).
[8] G. Wypych, Handbook of Antiblocking, Release, and Slip Additives, Chem. Tec. Publishing, Canada (2005).
[9] R.P. Singh, P. Yadav, Brassica., 5, 73 (2003).
[10] C.W. Peloso, M.J. O’Connor, S.W. Bigger, J. Scheirs, J. Polym. Degrad. Stab., 62, 285 (1998).
[11] M.C. Zoete, A.C. Kock-Von Dalen, F. Van-Rantwijk, R.A. Sheldon, J. Mol. Catal. B Enzym., 1, 141 (1996).
[12] N.P. Awasthi, V. Tripathi, R.P. Singh, Brassica., 8, 113 (2006).
[13] N.P. Awasthi, R.P. Singh, J. Oleo. Sci., 9, 507 (2007).
[14] R. Opsahl, In Kirk-Othmer Encyclopedia of Chemical Technology, Wiley, New York (1992).
[15] J.J. Litjens, A.J.J. Straathof, J.A. Jongejan, J. J. Heijnen, Chem. Commun., 13, 1255 (1999).
[16] G.P. Mueller, W.J. Driscoll, Vitam. Horm., 81, 55 (2009).
[17] O.A. Anyebe, K.I. Ekpenyong, Eur. J. Sci. Res., 16, 474 (2007).
[18] S. Nakamura, Solar to Chemical Energy Conversion: Fundamentals of Chemical Reaction Kinetics, Springer, New York (2016).
[19] M.A. Pearson, R.P. Hausinger, P.A. Karplus, J. Inorg. Biochemi., 67, 179 (1997).
[20] R.T. Morrison, R.N. Boyd, Organic chemistry, Allyn and bacon, inc., boston (1996)
[21] L.W. McKeen, Permeability Properties of Plastics and Elastomers (Fourth Edition), William Andrew, Amsterdam (2016).