Temperature and pH effects on the kinetics of 2-aminophenol auto-oxidation in aqueous solution

• Authors: Dumitru Oancea , Mihaela Puiu
• Languages of publication: EN

Abstracts

EN

The kinetics of the auto-oxidation of 2-aminophenol (OAP) to 2-amino-phenoxazin-3-one (APX) was followed in air-saturated aqueous solutions and the influence of temperature and pH on the auto-oxidation rate was studied. The kinetic analysis was based on a spectrophotometric method following the increase of the absorbance of APX. The process follows first order kinetics according to the rate law-d[OAP]/dt=k′[OAP]. The experimental data, within the pH range 4–9.85, were analyzed using both differential and incremental methods. The temperature variation of the overall rate constant was studied at pH=9.85 within the range 25–50°C and the corresponding activation energy was evaluated.

Keywords

EN

auto-oxidation; aminophenol; phenoxazinone

• Publisher: De Gruyter Open
• Journal: Open Chemistry
• Year: 2003
• Volume: 1
• Issue: 3
• Pages: 233-241

Dates

published

1 - 9 - 2003

online

1 - 9 - 2003

Contributors

author

Dumitru Oancea

• Department of Physical Chemistry, University of Bucharest, 4-12 bd. Elisabeta, sector 3, 70346, Bucharest, Romania

author

Mihaela Puiu

• Department of Physical Chemistry, University of Bucharest, 4-12 bd. Elisabeta, sector 3, 70346, Bucharest, Romania

References

• [1] J. Kochany and J.R. Bolton: “Mechanism of photodegradation of aqueous organic pollutants”, J. Phys. Chem., Vol. 13, (1991), pp. 5116–5120. http://dx.doi.org/10.1021/j100166a039[Crossref]
• [2] C. Prat, M. Vicente, S. Esplugas: “Treatment of bleaching waters in the paper industry by hydrogen peroxide and ultraviolet radiation”, Water Res., Vol. 22, (1988), pp. 663–668. http://dx.doi.org/10.1016/0043-1354(88)90176-5[Crossref]
• [3] W.H. Glaze and J.W. Kang: “The chemistry of water treatment involving ozone, hydrogen peroxide and ultraviolet radiation”, Ozone Sci. Eng., Vol. 9, (1987), pp. 352–353.
• [4] W.H. Glaze and J.W. Kang: “Advanced oxidation processes”, Ind. Eng. Chem. Res., Vol. 28, (1989), pp. 1580–1587. http://dx.doi.org/10.1021/ie00095a002[Crossref]
• [5] H.J. Fenton: “Oxidation of tartaric acid in the presence of iron”, J. Chem. Soc., Vol. 65, (1894), pp. 899–902. [Crossref]
• [6] H.R. Eisenhauer: “Oxidation of phenolic wastes”, J. Water. Pollut. Control. Fed., Vol. 36, (1964), pp. 1116–1120.
• [7] J. Hoigné and H. Bader: “Ozonization of water: role of hydroxyl radicals as oxidizing intermediates”, Env. Sci. Technol., Vol. 109, (1975), pp. 4216–4225.
• [8] H. Paillard, R. Brunet, M. Dore: “Optimal conditions for applying an ozone-hydrogen peroxide oxidizing system”, Water Res., Vol. 22, (1988), pp. 91–103. http://dx.doi.org/10.1016/0043-1354(88)90135-2[Crossref]
• [9] N. Getoff: “Radiation- and photoinduced degradation of pollutants in water”, Radiat. Phys. Chem., Vol. 37, (1991), pp. 673–678.
• [10] F.J. Rivas, S.T. Kolaczkowski, Beltrán, D.B. McLurgh: “Development of a model for the wet air oxidation of phenol based on a free radical mechanism”, Chem. Eng. Sci, Vol. 53:14, (1998), pp. 2575–2586. http://dx.doi.org/10.1016/S0009-2509(98)00060-8[Crossref]
• [11] U. Hollstein: “Actinomycin. Chemistry and mechanism of action”, Chem. Rev., Vol. 74, (1974), pp. 625–652. http://dx.doi.org/10.1021/cr60292a002[Crossref]
• [12] C.E. Barry, G.N. Parmesh, T.P. Begley: “Phenoxazinone synthase: enzymatic catalysis of an aminophenol oxidative cascade”, J. Am. Chem. Soc., Vol. 110, (1988), pp. 3333. http://dx.doi.org/10.1021/ja00218a072[Crossref]
• [13] W. Prinz and N. Savage: “A simple, non-enzymatic synthesis of cinnabarinic acid (2-amino-3H-phenoxazine-1, 9-dicarboxilic acid)”, Hoppe-Seyler’s Z. Physiol. Chem., Vol. 358, (1977), pp. 1161–1163.
• [14] W. Schäfer: “The chemistry of phenoxazones”, Prog. Org. Chem., Vol. 6, (1964), pp. 135–163.
• [15] O. Toussaint and K. Lerch: “Catalytic oxidation of 2-aminophenols and ortho hydroxylation of aromatic amines by tyrosinase”, Biochemistry, Vol. 26, (1987), pp. 8567–8571. http://dx.doi.org/10.1021/bi00400a011[Crossref]
• [16] C.E. Barry, G.N. Parmesh, T.P. Begley: “Phenoxazinone synthase: mechanism for the formation of the phenoxazinone chromophore of actinomycin”, Biochemistry, Vol. 28, (1989), pp. 6323–6333. http://dx.doi.org/10.1021/bi00441a026[Crossref]
• [17] L. Prati, M. Rossi, N. Ravasio: “Interaction of molecular oxygen with aminophenols mediated by copper metal and copper compounds”, J. Mol. Cat., Vol. 75, (1992), pp. 347–355. http://dx.doi.org/10.1016/0304-5102(92)80136-5[Crossref]
• [18] A. Tomoda, E. Shirasawa, S. Nagao, M. Minami, Y. Yoneyama: “Involvement of oxidoreductive reactions of intracellular hemoglobin in the metabolism of 3-hydroxyanthranilic acid in human erythrocytes”, Biochem. J. Vol. 22, (1984), pp. 755–760.
• [19] J. Kaizer, R. Csonka, G. Speier: “TEMPO-initiated oxidation of 2-aminophenol to 2-aminophenoxazin-3-one”, J. Mol. Cat., Vol. 180, (2002), pp. 91–96. http://dx.doi.org/10.1016/S1381-1169(01)00443-5[Crossref]
• [20] V. Stuzka and E. Sinderlarova: “Electronic spectra of phenoxazine dyestuffs and substituent effects on the position of long-wave absorption bands”, Collection Czech. Chem. Commun., Vol. 42, (1977), pp. 13333–13337.
• [21] K. Ebert, H. Ederer, T.L. Isenhour: Computer Applications in Chemistry, VCH, Weinheim, 1989, pp. 359–387.
• [22] J.F. Rusling and T.F. Kumosinski: Nonlinear Computer Modeling of Chemical and Biochemical Data, Academic Press, New York, 1996, pp. 3–31.
• [23] J.H. Espenson: Chemical Kinetics and Reaction Mechanisms, McGraw-Hill Inc. New York, 1995, pp. 26–27.
• [24] M.J. Pilling and P.W. Seakins: Reaction Kinetics, Oxford Science Publications, 1995, pp. 16–18.
• [25] C.H. Bamford and C.H.F. Tipper: Chemical Kinetics, Vol. 16, Elsevier, Amsterdam, 1980, pp. 180–190.
• [26] IUPAC: Solubility Data Series-Oxygen and Ozone, Vol. 7, Pergamon Press, New York, 1981.
• [27] T. Nogami, T. Hishida, M. Yamada, H. Milkawa, Y. Shirota: “Formation and reactions of o-benzoquinone mono- and di- imines”, Bull. Chem. Soc. Jpn., Vol. 48, (1975), pp. 3709–3714. http://dx.doi.org/10.1246/bcsj.48.3709[Crossref]

Identifiers

DOI

10.2478/BF02476226