Abstract
Kinetics and mechanism of the reaction of ozone with 2-acetoxytoluene in acetic anhydride in the presence of sulfuric acid were studied. It was shown that the prevailing reaction route under these conditions is ozonolysis (89%), and the selectivity of the oxidation of the substrate by the methyl group is no higher 9%. However, in the presence of manganese(II) sulfate as a catalyst, the selectivity increases to 76%. The major reaction products were 2-acetoxybenzyl acetate (59%) and 2-acetoxybenzylidene diacetate (17%). In the presence of a manganese bromide catalyst, the oxidation depth increases, and the major reaction product is already 2-acetoxybenzylidene (66%), while the yield of 2-acetoxybenzyl acetate is 15%. The mechanism of the redox catalysis is considered, that explains the experimental results.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Galstyan, G.A., Zh. Fiz. Khim., 1992, vol. 66, no. 4, p. 75.
Galstyan, G.A., Tyupalo, N.F., and Razumovskii, S.D., Ozon i ego reaktsii s aromaticheskimi soedineniyami (Ozone and Its Reactions with Aromatic Compounds), Lugansk: Vost. Ukr. Gos. Univ., 2004.
Razumovskii, S.D. and Zaikov, G.E., Ozon i ego reaktsii s organicheskimi soedineniyami (Ozone and Its Reactions with Organic Compounds), Moscow: Nauka, 1974, p. 229.
Bailey, P.S., Ozonation in Organic Chemistry, Vol. 2. Nonolefinic Compounds, New York: Academic, 1982, p. 19.
Pryor, W.A., Norio, O., and Church, D.F., J. Am. Chem. Soc., 1982, vol. 104, p. 5813.
Zakharov, I.V. and Galetii, Yu.V., Neftehimiya, 1978, vol. 18, no. 4, p. 615.
Denisov, E.T., Konstanty skorosti gomoliticheskih zhid kofaznyh reaktsii (Rate Constants of Homolytic Liquid-Phase Reactions), Moscow: Nauka, 1971.
Emanuel’, N.M., Denisov, E.T., and Maizus, E.K., Tsepnye reaktsii okisleniya uglevodorodov v zhidkoi faze (Chain Oxidation of Hydrocarbons in the Liquid Phase), Moscow: Nauka, 1965.
Kamiya, Y., J. Catal., 1974, vol. 33, no. 3, p. 480.
Galstyan, A.G, Sedikh, G.O, and Galstyan, G.A., Ukr. Khim. Zh., 2007, vol. 73, nos. 5–6, p. 104.
Agranomov, A.E. and Shabarov, Yu.S., Laboratornye raboty v organicheskom praktikume (Laboratory Man ual on Organic Chemistry), Moscow: Mosk. Gos. Univ., 1971.
Weygand-Hilgetag Organisch-chemische Experimen tierkunst, Hilgetag, G. and Martini, A., Eds., Leipzig: Barth, 1964, 3rd ed.
Becker, H. and Berger, W., Organikum, Berlin: Wis sennschaften, 1976. Translated under the title Manual on Organic Chemistry, Moscow: Mir, 1979, vol. 2.
Author information
Authors and Affiliations
Corresponding author
Additional information
Original Russian Text © A.G. Galstyan, 2008, published in Zhurnal Obshchei Khimii, 2008, Vol. 78, No. 9, pp. 1457–1462.
Rights and permissions
About this article
Cite this article
Galstyan, A.G. Oxidation of 2-acetoxytoluene with ozone in acetic anhydride. Russ J Gen Chem 78, 1690–1694 (2008). https://doi.org/10.1134/S1070363208090089
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S1070363208090089