Abstract
Liquid-phase catalytic oxidation into acids by air was studied for the following hydrocarbons: isomers of cyclohexyltoluenes and cyclohexyl derivatives of para-xylene, mesitylene, pseudocumene, cyclopentyltoluene, cyclohexyladamantane, 4-methylbiphenyl, 2,4-, 2,5- and 3,4-dimethylbiphenyls, hydroxymethylbiphenyls, and hydroxymethylbenzenes. The oxidation of cyclohexyltoluenes involves a methyl group and proceeds without participation of the α-CH bond of the cyclohexyl fragment in the oxidative conversions. The reactivity of the hydrocarbons increases in the order ortho < meta < para. Consecutive conversions of the methyl groups to carboxyls occur during the oxidation of dimethylbiphenyls. In 3,4- and 2,5-dimethylbiphenyls, the methyl groups in the para and ortho positions, respectively, are first oxidized, whereas the reactivity of both of the methyl groups in 2,4-dimethylbiphenyl is virtually the same. The mechanism of the oxidation of hydroxymethylbiphenyls and hydroxymethylbenzenes involves the formation of an unstable cation radical, which is then stabilized by emitting a proton, giving hydroxybenzyl, a more stable radical.
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REFERENCES
S.G. Koshel E.K. Rudkovsky G. Poli et al. (1998) Chim. Ind. 80 IssueID2 183
Koshel’, S.G., Obukhova, T.A., Krylova, N.N., et al., Neftekhimiya, 1989, no. 2, p. 257.
T.A. Obukhova S.G. Koshel’ A.I. Rusakov (1991) Izv. Vyssh. Uchebn. Zaved., Ser. Khim. Khim. Tekhnol. 34 IssueID9 68
S.G. Koshel’ I.V. Shutova Yu.E. Shapiro et al. (1992) Zh. Org. Khim. 28 IssueID2 363
T.A. Obukhova A.I. Rusakov S.G. Koshel’ et al. (1992) Zh. Org. Khim. 28 IssueID4 756
G.N. Koshel’ T.B. Krestinina Yu.E. Shapiro et al. (1988) Zh. Org. Khim. 24 IssueID7 1499
N.G. Digurov (1982) Doctoral (Chem.) Dissertation Moscow Inst. of Chemical Technology Moscow
S.G. Koshel’ N.V. Lebedeva E.K. Rudkovskii et al. (1997) Zh. Org. Khim. 33 IssueID1 65
S.G. Koshel’ N.V. Lebedeva E.K. Rudkovskii et al. (1996) Bashk. Khim. Zh. 3 IssueID7 18
S.G. Koshel’ N.V. Lebedeva E.K. Rudkovskii et al. (1998) Zh. Org. Khim. 34 IssueID2 254
S.G. Koshel’ V.V. Voronenkov G.N. Koshel’ et al. (1997) Zh. Org. Khim. 33 IssueID7 1114
G.N. Koshel’ P. Magan’ini S.G. Koshel’ et al. (2001) Zh. Org. Khim. 37 IssueID6 877
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Translated from Kinetika i Kataliz, Vol. 45, No. 6, 2004, pp. 872–876.
Original Russian Text Copyright © 2004 by G. Koshel’, S. Koshel’, Postnova, Lebedeva, Kuznetsova, Belysheva, Yun’kova.
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Koshel’, G.N., Koshel’, S.G., Postnova, M.V. et al. Liquid-phase catalytic oxidation of methyl derivatives of biphenyl. Kinet Catal 45, 821–825 (2004). https://doi.org/10.1007/s10975-005-0044-5
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DOI: https://doi.org/10.1007/s10975-005-0044-5