Abstract
The oxidation process of aminophenols in acidic and alkaline media was investigated in order to better understand their stoichiometry and reaction pathways. The mechanistic contemplation was found to be dependent on hydrogen ion concentration. The reaction behaved as second order in the range of pH 6.0–8.0 and first order in the range of pH 10.5–12.0. The speciation of aminophenols and peroxymonosulfate ion have been explored. The stoichiometry indicates one mole of each ortho-aminophenol (OAP) and para-aminophenol (PAP) reacts with 2 mol of peroxomonosulfate. Besides, mechanism and rate law of the oxidation process of aminophenols have been proposed to explain the pH dependence. A structural investigation of intermediates and degradation products was also carried out. This research may establish a framework for anticipating the oxidation reaction process of different aminophenols in wastewater treatment.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Anbia M, Rezaie M (2017) Generation of sulfate radicals by supported ruthenium catalyst for phenol oxidation in water. Res Chem Intermed 43:245–257. https://doi.org/10.1007/s11164-016-2618-4
Andreozzi R, Caprio V, Marotta R, Vogna D (2003) Paracetamol oxidation from aqueous solutions by means of ozonation and H2O2/UV system. Water Res 37:993–1004. https://doi.org/10.1016/S0043-1354(02)00460-8
Ball DL, Edwards JO (1956) The Kinetics and mechanism of the decomposition of Caro’s acid. I J Am Chem Soc 78:1125–1129. https://doi.org/10.1021/ja01587a011
Bernadou J, Bonnafous M, Labat G et al (1991) Model systems for metabolism studies: biomimetic oxidation of acetaminophen and ellipticine derivatives with water-soluble metalloporphyrins associated to potassium monopersulfate. Drug Metab Dispos 19:360–365
Fleury PF, Lange J (1933) Determination of periodic acid in the presence of iodic acid
Iturmendi A, Iglesias M, Munárriz J et al (2017) Efficient preparation of carbamates by Rh-catalysed oxidative carbonylation: unveiling the role of the oxidant. Chem Commun 53:404–407. https://doi.org/10.1039/C6CC09133D
Jordá LS-J, Martín MMB, Gómez EO et al (2011) Economic evaluation of the photo-Fenton process. Mineralization level and reaction time: the keys for increasing plant efficiency. J Hazard Mater 186:1924–1929. https://doi.org/10.1016/j.jhazmat.2010.12.100
Kolthoff IM, Sandell EB (1944) Textbook of quantitative inorganic analysis. John Wiley & Sons, Ltd
Lerner L (2011) Identity of a purple dye formed by peroxidic oxidation of p-aminophenol at low pH. J Phys Chem A 115:9901–9910. https://doi.org/10.1021/jp2045806
Manila K, Bhatt N (2017) Applications of oxone in chemical kinetics, synthetic chemistry and environmental chemistry: a review. Environ Conserv J 18:135–140
Manila, Kaushik RD, Bhatt N et al (2020a) A kinetic spectrophotometric analysis of oxidation of a potential pollutant ortho aminophenol by potassium monopersulfate for its conversion into less toxic compound. Rasayan J Chem 13:1424–1437
Manila N, Pal A, Sharma S (2020b) Uncatalyzed peroxomonosulphate degradation of para aminophenol, a potential pollutant. Pollut Res 39:461–467
Munusamy S, Muralidharan VP, Iyer SK (2017) Direct oxidative cascade cyclisation of 2-aminobenzoic acid and arylaldehydes to aryl 4H–3,1-benzoxazin-4-ones with oxone. Tetrahedron Lett 58:520–523. https://doi.org/10.1016/j.tetlet.2016.12.072
Najafpour MM, Moghaddam NJ (2017) An efficient nickel oxides/nickel structure for water oxidation: a new strategy. New J Chem 41:1909–1913. https://doi.org/10.1039/C6NJ02842J
Oancea D, Puiu M (2003) Temperature and pH effects on the kinetics of 2-aminophenol auto-oxidation in aqueous solution. Open Chem 1:233–241. https://doi.org/10.2478/BF02476226
Panorel I, Preis S, Kornev I et al (2013) Oxidation of aqueous paracetamol by pulsed corona discharge. Ozone Sci Eng 35:116–124. https://doi.org/10.1080/01919512.2013.760415
Reddy KR, Kannaboina P, Das P (2017) Palladium-catalyzed chemoselective switch: synthesis of a new class of indenochromenes and pyrano[2,3- c ]carbazoles. Asian J Org Chem 6:534–543. https://doi.org/10.1002/ajoc.201600530
Rivas FJ, Beltrán FJ, Carvalho F, Alvarez PM (2005) Oxone-promoted wet air oxidation of landfill leachates. Ind Eng Chem Res 44:749–758. https://doi.org/10.1021/ie0401511
Rivas FJ, García R, García-Araya JF, Gimeno O (2008) Promoted wet air oxidation of polynuclear aromatic hydrocarbons. J Hazard Mater 153:792–798. https://doi.org/10.1016/j.jhazmat.2007.09.025
Shu H-Y, Huang S-W, Tsai M-K (2016) Comparative study of acid blue 113 wastewater degradation and mineralization by UV/persulfate and UV/Oxone processes. Desalin Water Treat 57:29517–29530. https://doi.org/10.1080/19443994.2016.1172031
Skoumal M, Cabot P-L, Centellas F et al (2006) Mineralization of paracetamol by ozonation catalyzed with Fe2+, Cu2+ and UVA light. Appl Catal B Environ 66:228–240. https://doi.org/10.1016/j.apcatb.2006.03.016
Sun M, Yao R, You Y et al (2007) Degradation of 4-aminophenol by hydrogen peroxide oxidation using enzyme from Serratia marcescens as catalyst. Front Environ Sci Eng China 1:95–98. https://doi.org/10.1007/s11783-007-0018-0
Yang J-CE, Yuan B, Cui H-J et al (2017) Modulating oxone-MnOx/silica catalytic systems towards ibuprofen degradation: Insights into system effects, reaction kinetics and mechanisms. Appl Catal B Environ 205:327–339. https://doi.org/10.1016/j.apcatb.2016.12.046
Acknowledgements
We thank Department of chemistry, Gurukula Kangri (Deemed to be University), for help during the course of studies.
Funding
This research did not receive any specific grant from funding agencies in the public, commercial, or not-for-profit sectors.
Author information
Authors and Affiliations
Corresponding author
Ethics declarations
Conflict of interest
The authors declare that they have no conflict of interest
Additional information
Editorial responsibility: Maryam Shabani.
Rights and permissions
About this article
Cite this article
Kashni, M., Singh, J. & Kaushik, R.D. Oxidation of aminophenols in acidic and alkaline solutions by oxone: stoichiometry and mechanism. Int. J. Environ. Sci. Technol. 20, 3901–3909 (2023). https://doi.org/10.1007/s13762-022-04151-6
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s13762-022-04151-6