Chloramine-T Assisted Oxidative Decolourization of Tartrazine (Food Dye) in Acid Medium: Kinetic and Mechanistic Investigations

Authors

  • Harsha Muddegowda Department of Chemistry, PES College of Engineering, Mandya 571401, Karnataka, India
  • Charan Kumar Hunsur Chandrashekar Department of Chemistry, PES College of Engineering, Mandya 571401, Karnataka, India
  • Kumara Manikyanahalli Narasigowda Department of Chemistry, Manasagangotri, University of Mysore, Mysuru 5700 06, Karnataka, India

DOI:

https://doi.org/10.48048/tis.2022.6184

Keywords:

Tartrazine, Chloramine-T, Kinetics, Reaction mechanism, Oxidative decolorization

Abstract

Tartrazine (TAZ) is a food color additive. It has been found to be contaminated with Benzidine or other carcinogens. It causes hypersensitivity reactions. The metabolites which are formed during digestion are responsible for the problems caused by these dyes. So, in the present work the kinetic and mechanistic aspects of oxidation of tartrazine have been studied with the help of mild oxidizing agent chloramine-T (CAT) in acid medium at 26 °C. The reaction exhibited 2nd-order dependence of rate with (CAT), inverse fractional order dependence of rate with (TAZ) and (H+). Solvent composition shows negative effect indicating the involvement of negative ion-dipolar molecule in the rate determining step. Variation of ionic strength of the medium and addition of halide ions had no effect on the reaction rate. Addition of p-toluenesulphonamide (PTS), the reduction product retards the rate of reaction. Oxidation products were identified as 4-(5-Hydroxy-4-nitoso-pyrazol-1-yl)- benzenesulphonic acid and 4-amino-benzene sulphonic acid which are often allergic to human beings. These oxidation products were characterized by LC-MS. Activation parameters have been evaluated from Arrhenius-Eyring plots. The observed results have been explained by plausible mechanism and related rate law have been deduced.

HIGHLIGHTS

  • The kinetics of oxidation of Tartrazine has been studied in acid medium by using CAT as an oxidizing agent
  • Effects of different parameters like ionic strength, addition of reduction product, halide ions and temperature were studied as supporting data for the mechanism proposed for the oxidation of Tartrazine
  • Products were isolated after complete oxidation and were characterized with the help of suitable technique
  • A rate equation is derived and a suitable mechanism is proposed for the oxidation of the substrate


GRAPHICAL ABSTRACT

Downloads

Download data is not yet available.

References

YI Hassan, NHM Saeed. Kinetics and mechanism of oxidation of diethyl ether by chloramine-T in acidic medium. J. Chem. 2012; 9, 957405.

Sukhdev and Puttaswamy. Oxidation of tricyclic antidepressant drugs with chloramine-T in acidic solutions: kinetic, mechanistic and thermodynamic studies. Springer Plus. 2013; 2, 30.

XL Armesto, LM Canle, MV Garcia and JA Santaballa. Aqueous chemistry of N-halo- compounds. Chem. Soc. Rev. 1998; 27, 453-60.

D Gupta, I Sharma and PD Sharma. Kinetics and mechanism of osmium (VIII) catalyzed oxidation of propane-1, 3-diol by chloramine T in aqueous alkaline medium. J. Chem. Res. 1998; 762, 3377-92.

Puttaswamy, RV Jagadeesh and N Vaz. Oxidation of some catecholamines by sodium N-chloro-p-toluenesulfonamide in acid medium: A kinetic and mechanistic approach. Cent. Eur. J. Chem. 2005; 3, 326-46.

H Ramachandra, KS Rangappa and NMM Gowda. Oxidation of substituted phenethyl alcohols by sodium N-chloro-4-toluenesulfonamide, a kinetic study. Monatsh Chem. 1996; 127, 241-55.

KN Vinod, Puttaswamy and KN Ningegowda. Oxidative decolorization of triphenylmethane dyes by chloramine-T in alkaline medium catalyzed by Pd (II): A comparative spectrophotomeric kinetic and mechanistic approach. J. Mol. Catalysis A: Chemical. 2009; 298, 60-8.

PA Prashanth, BK Kempegowda, S Ananda, KS Rangappa and MN Kumara. Ru(III) chloride-catalysed oxidation of some α-amino acids by CAT in hydrochloric acid medium: Mechanistic investigation and kinetic modeling. J. Mol. Catalysis A: Chem. 2014; 383-384, 203-8.

S Nadupalli, N Koorbanally, S B Jonnalagadda. Kinetics and mechanism of the oxidation of amaranth with hypochlorite. J. Phys. Chem. A. 2011; 115, 7948-54.

CH Wu, CL Chang and CY Kuo. Decolorization of amaranth by advanced oxidation process. React. Kinet. Mech. Catal. 2005; 86, 37-43.

P Dachipally and SB Jonnalagadda. Kinetics of ozone- initiated oxidation of textile dye, amaranth in aqueous systems. J. Environ. Sci. Health, Part A. 2011; 46, 887-97.

AH Gemeay, AM Habib and MAB El-Din. Kinetics and mechanism of the uncatalyzed and Ag (I)-catalyzed oxidative decolorization of Sunset Yellow and Ponceau 4R with peroxydisulfate. Dyes Pigm. 2007; 74, 458-63.

KNV Puttaswamy and KNN Gowda. Mechanistic aspects for the oxidation of sunset yellow dye by Chloramine-T in the presence of perchloric acid and in sodium hydroxide catalyzed by Os(VIII): A spectrophotometric approach. Inorganica Chim. Acta 2009; 362, 2044-51.

MA Salem and AH Gemeay. Kinetics of the oxidation of tartrazine with peroxydisulfate in the presence and absence of catalyst. Monatsh. fuer Chem. 2000; 131, 117-29.

M Darwish, A Mohammadi and A Navid. Microwave-assisted polyol synthesis and characterization of pyp-capped CdS nanoparticles for the photolytic degradation of tartrazine. Mater. Res. Bull. 2016; 74, 387-96.

WRP Barros, SA Alves, PC Franco, JR Steter, RS Rocha and MRV Lanza. Electrochemical degradation of tartrazine dye in aqeous solution using a modified diffusion electrode. J. Electrochem. Soc. 2014; 161, H438-H442.

P Oancea and V Meltzer, Photo-Fenton process for the degradation of tartrazine (E102) in aqeous medium. J. Taiwan Inst. Chem. Eng. 2013; 44, 990-4.

N Seok-Eun, J Sang-Gu, J Ga-Seop, K Di-Young and J Chang-Sik. Preparation of Zinc oxide by Hydrothermal precipitation and degradation of tartrazine. Korean Inst. Chem. Eng. 2011; 49, 752-7.

N Bellakhal, M Dachraoui, N Oturan and MA Oturan. Degradation of tartrazine in water by electro-Fenton process, J. Soc. Chim. Tunisie. 2006; 8, 223-8.

J C Morris, JR Salazar and MA Winemann. Equilibrium studies on chloro compounds; the ionization constant of N-chloro-p-toluene-sulfonamide. J. Am. Chem. Soc. 1948; 70, 2036.

AI Vogel. Text book of quantitative inorganic analysis. 4th eds., Longman Sc & Tech, London, 1980.

JN Bronsted. Die Bedeutung des Aktivitatsbegriffes fur die chemische Reaktiongeschwindigkeit. Z. Physik. Chem., 1992; 102, 169.

KS Kanse, SD Chavan, CS Mali, AC Kumbharkhane and SC Mchrotra. Structural study of methanol-water mixture from dielectric parameters. Indian J. Phys. 2006; 80, 265-9.

EA Moelwyn-Hughes. The kinetics of reaction in solutions. Clarendon Press, Oxford, 1947.

AA Frost and RG Pearson. Kinetics and mechanism. 2nd eds., Wiley, New York, 1961.

GF Jeyanthi, G Vijayakumar and KP Elango. The effect of solvent on the kinetics of the oxidation of benzaldehydes by quinolinium chlorochromate in aqueous organic solvent media. J. Serb. Chem. Soc. 2002; 67, 803-8.

KK Ghosh, KK Krishnani and S Ghosh. Effect of solvents on the kinetics and mechanism of the acidic and alkaline hydrolysis of hydroxamic acids. Indian J. Chem. 1999; 38B, 337-42.

ES Amis and G Jaffe. J. Chem. Phys. 1942; 10, 598.

RM Nielson, GE McManis, LK Safford and MJ Weaver. Solvent and electrolyte effects on the kinetics of ferrocenium-ferrocene self-exchange. A reevaluation. J. Phys. Chem. 1989; 93, 2152-7.

E Bishop and VJ Jennings. Analytical applications of chloramine-T. Crit. Rev. Anal. Chem. 2008; 3, 407-19.

CB Susha and JI Bhat. Ion-solvation studies of chloramine-T species in water, acetonitrile, DMF and their mixture by conductometry. Indian J. Chem. 1996, 35A, 1052-5.

JI Bhat and NV Sabitha. Solvation behavior of Chloramine-T in solvent mixtures at different temperature. Indian J. Chem. Technol. 2004; 11, 17-22.

SS Narayana and VRS Rao. Chlorine isotopic exchange reaction between chloramine-T and chloride ion. Radio Chem. Acta 1983; 32, 1082.

Downloads

Published

2022-10-03