Abstract
p-tert-Butyphenol is a valuable product of basic organic synthesis, widely used in various branches of industry. The relationships of acid decomposition of p-tert-butylcumene hydroperoxide to p-tert-butylphenol and acetone as one of the key steps of the alternative method for p-tert-butylphenol synthesis were studied. The influence exerted by temperature, catalyst concentration, and initial concentration of p-tert-butylcumene hydroperoxide on its acid decomposition was examined. Conditions ensuring preparation of p-tert-butylphenol in 92% yield were found. A kinetic model of the acid decomposition of p-tert-butylcumene hydroperoxide in the presence of concentrated sulfuric acid was constructed; it adequately describes the experimental data and allows substantiation of the reaction mechanism.
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Saha, M., Hossain, M.K., Ashaduzzama, M., Afroza, S.T., Galib, M., and Sharif, N., Bangladesh J. Sci. Ind. Res., 2009, vol. 44, no. 1, pp. 131–136. https://doi.org/10.3329/bjsir.v44i1.2722
Atwood, J.L., Barbour, L.J., Thallapally, P.K., and Wirsig, T.B., Chem. Commun., 2005, pp. 51–53. https://doi.org/10.1039/B416752J
Voronin, I.O., Nesterova, T.N., Zhuravskii, E.A., and Strelchik, B.S., Kinet. Catal., 2014, vol. 55, no. 6, pp. 705–711. https://doi.org/10.1134/S0023158414060147
Zakoshanskii, V.M., Fenol i atseton: Analiz tekhnologii, kinetiki i mekhanizma osnovnykh reaktsii (Phenol and Acetone: Analysis of the Technology, Kinetics, and Mechanism of the Main Reactions), St. Petersburg: Khimizdat, 2009, pp. 149–189.
Kurganova, E.A., Koshel', G.N., and Dakhnavi, E.M., Petrol. Chem., 2017, vol. 57, no. 3, pp. 262–266. https://doi.org/10.1134/S0965544117020189
Koshel', G.N., Glazyrina, I.I., Bychkov, B.N., and Farberov, N.I., Zh. Prikl. Khim., 1978, vol. 51, no. 10, pp. 2325–2329.
Glazyrina, I.I., Shapiro, Yu.E., Koshel', G.N., and Shutova, I.V., Zh. Org. Khim., 1979, vol. 49, no. 2, pp. 444–448.
Vodnár, J., React. Kinet. Catal. Lett., 1979, vol. 10, no. 3, pp. 237–241. https://doi.org/10.1007/BF02068990
Vodnár, J., Fejes, P., Varga, K., and Berger, F., Appl. Catal. A: General, 1995, vol. 122, pp. 33–40. https://doi.org/10.1016/0926-860X(94)00212-6
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Russian Text © The Author(s), 2019, published in Zhurnal Prikladnoi Khimii, 2019, Vol. 92, No. 11, pp. 1427-1434.
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Yarkina, E.M., Kurganova, E.A., Frolov, A.S. et al. Acid Decomposition of p-tert-Butylcumene Hydroperoxide to p-tert-Butylphenol and Acetone. Russ J Appl Chem 92, 1524–1530 (2019). https://doi.org/10.1134/S1070427219110090
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DOI: https://doi.org/10.1134/S1070427219110090