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RESEARCH ARTICLE
Contents Vol 66(7)

A Much-Needed Mechanism and Reaction Rate for the Oxidation of Phenols with ClO2: A Joint Experimental and Computational Study

Carlos Alberto Huerta Aguilar A , Jayanthi Narayanan B , Mariappan Manoharan C , Narinder Singh D E and Pandiyan Thangarasu A E
+ Author Affiliations
- Author Affiliations

A Facultad de Química, Universidad Nacional Autónoma de México (UNAM), Ciudad Universitaria, Coyoacán, 04510 México D.F., México.

B División de Nanotecnología, Universidad Politécnica del Valle de México, Av. Mexiquense, C.P. 54910 Tultitlan, Estado de México, México.

C School of Science, Engineering and Mathematics, Bethune-Cookman University, Daytona Beach, Florida 32114, USA.

D Department of Chemistry, Indian Institute of Technology Ropar, Rupnagar, Panjab 140001, India.

E Corresponding authors. Email: nsingh@iitpr.ac.in; pandiyan@servidor.unam.mx

Australian Journal of Chemistry 66(7) 814-824 https://doi.org/10.1071/CH13101
Submitted: 16 January 2013  Accepted: 5 April 2013   Published: 26 April 2013

Abstract

The oxidation of phenols with chlorine dioxide, a powerful means to eliminate phenol pollutants from drinking water, is explored. Kinetic experiments reveal that 2,4,6-trichlorophenol exhibits a lower oxidation rate than other phenols because the chlorine atoms (σ = 0.22) at ortho and para-positions decrease the benzene’s electron density, in agreement with the Hammett plot. The oxidation of phenol was found to be second order with respect to phenol and first order with respect to ClO2 and a possible mechanism is proposed. The phenol/ClO2 oxidation was found to be pH-dependent since the reaction rate constant increases with increasing pH. The oxidation rate was also significantly enhanced with an increasing methanol ratio in water. The oxidation products, such as benzoquinones, were analysed and confirmed by liquid chromatography and gas chromatography–mass spectrometry. Density functional theory computations at both the B3LYP/6-311+G(d,p) and M06-2X.6-311+G(d,p) levels with the SCRF-PCM solvation model (i.e. with water) further supported the proposed mechanisms in which activation barriers predicted the right reactivity trend as shown by the kinetic experiments.


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