Oxidation of vanillin by peroxomonosulphate-thermodynamic and kinetic investigation

S. Kutti Rani; S. Nirmal Kumar; Crystal Y. Wilson; A. Gopi; D. Easwaramoorthy

Journal of Industrial and Engineering Chemistry, Vol.15, No.6, 898-901, November, 2009

DOI10.1016/j.jiec.2009.09.020 Export Citation

Oxidation of vanillin by peroxomonosulphate-thermodynamic and kinetic investigation

S. Kutti Rani, S. Nirmal Kumar¹, Crystal Y. Wilson, A. Gopi¹, and D. Easwaramoorthy^†

B.S. Abdur Rahman University, Chennai 600 048, India
¹Thiru Seven Hills Polytechnic College, Maduravoyal, Chennai 602 102, India

E-mail:

The oxidation of vanillin by peroxomonosulphate (PMS) in acetic acid.sodiumacetate bufferedmedium was carried out at 308 K. The rate was first order with respect to [vanillin] and [PMS]. The rate increased with increase in pH and the rate was too fast to be measured at pH 5.2. The rate increased with increase in [acetate] and the plot of k(obs) versus [acetate] was a straight line with positive intercept. Variation of ionic strength had no effect on the rate of the reaction. Effects of polarity were studied with five different solvents and in all the cases, log kobs versus 1/ε were linear with negative slope. The reaction had been carried out at four different temperatures and the activation and thermodynamic parameters were calculated. The product of oxidation was confirmed as vanillic acid by IR, 1H NMR and GC-MS spectral analysis. Based on the results obtained a reaction scheme had been proposed and the rate law was derived.

Keywords:Kinetics and oxidation;Peroxomonosulphate;Vanillin;Vanillic acid

[References]

Davidson PM, Naidu AS, in: Naidu AS (Ed.), Phyto-phenols, Natural Food Antimicrobial Systems, CRC Press, USA, 2000, p. 265.
Kathari C, Pol P, Nandibewoor S, Turk. J. Chem., 26, 229 (2002)
Jose P, Nandibewoor S, Suresh M, J. Solut. Chem., 35, 51 (2006)
Hiremath DC, Kiran TS, Nandibewoor S, Int. J. Chem. Kinet., 39, 236 (2007)
Puttaswamy, Suresha N, Jagadeesh R, Vaz N, Syn. React. Inorg., Metal-Org. Nanometal Chem., 35, 845 (2005)
Sachdev D, Dubey A, Mishra BG, Kannan S, Catal. Commun., 9, 391 (2008)
Narsaiah AV, Synlett, 7, 1178 (2002)
Wozniak LA, Stec WJ, Tetrahedron Lett., 40, 2637 (1999)
Chen MY, Patkar LN, Chen HT, Lin CC, Carbohyd. Res., 338, 1327 (2003)
Mohajer D, Iranpoor N, Rezaeifard A, Tetrahedron Lett., 45, 631 (2004)
Webb KS, Ruszkay SJ, Tetrahedron Lett., 54, 401 (1998)
Johnson P, Taylor RJK, Tetrahedron Lett., 38, 5873 (1997)
Brik ME, Tetrahedron Lett., 36, 5519 (1995)
Sundar M, Easwaramoorthy D, Kutti Rani S, Palanichamy M, J. Solut. Chem., 36, 1129 (2007)
Kirkwood JG, J. Chem. Phys., 2, 351 (1934)
Gopalakrishnan G, Hogg JL, J. Org. Chem., 50, 1206 (1985)

[1] Davidson PM, Naidu AS, in: Naidu AS (Ed.), Phyto-phenols, Natural Food Antimicrobial Systems, CRC Press, USA, 2000, p. 265.

[2] Kathari C, Pol P, Nandibewoor S, Turk. J. Chem., 26, 229 (2002)

[3] Jose P, Nandibewoor S, Suresh M, J. Solut. Chem., 35, 51 (2006)

[4] Hiremath DC, Kiran TS, Nandibewoor S, Int. J. Chem. Kinet., 39, 236 (2007)

[5] Puttaswamy, Suresha N, Jagadeesh R, Vaz N, Syn. React. Inorg., Metal-Org. Nanometal Chem., 35, 845 (2005)

[6] Sachdev D, Dubey A, Mishra BG, Kannan S, Catal. Commun., 9, 391 (2008)

[7] Narsaiah AV, Synlett, 7, 1178 (2002)

[8] Wozniak LA, Stec WJ, Tetrahedron Lett., 40, 2637 (1999)

[9] Chen MY, Patkar LN, Chen HT, Lin CC, Carbohyd. Res., 338, 1327 (2003)

[10] Mohajer D, Iranpoor N, Rezaeifard A, Tetrahedron Lett., 45, 631 (2004)

[11] Webb KS, Ruszkay SJ, Tetrahedron Lett., 54, 401 (1998)

[12] Johnson P, Taylor RJK, Tetrahedron Lett., 38, 5873 (1997)

[13] Brik ME, Tetrahedron Lett., 36, 5519 (1995)

[14] Sundar M, Easwaramoorthy D, Kutti Rani S, Palanichamy M, J. Solut. Chem., 36, 1129 (2007)

[15] Kirkwood JG, J. Chem. Phys., 2, 351 (1934)

[16] Gopalakrishnan G, Hogg JL, J. Org. Chem., 50, 1206 (1985)