Abstract
The present study considered the influence of various factors on the catalytic activity of systems based on a combination of tetrakis(oxodiperoxotungsto)phosphate(3−) with quaternary ammonium cations, for example, with methyltri-n-octylammonium [Me(n-C8H17)3N]+. The catalysts were tested in oxidation of cycloolefins (cyclohexene and cyclooctene), alcohols (octan-1-ol and phenylmethanol), and unsaturated fatty acids (cis-9-octadecenoic and 12-hydroxy-9Z-octadecenoic acids) with a 30% hydrogen peroxide solution. These reactions proceed under mild conditions (atmospheric pressure, 80–90 °C) to give carboxylic acids. The catalytic systems were characterized by vibrational (IR and Raman) spectroscopy. The state of the systems formed from various precursors, viz., polyoxometallates and phase-transfer catalysts, was studied. It was demonstrated for the first time that the structure formation of peroxo complexes depends on the nature of the halide anion of the quaternary ammonium salt used. The melting points of individual catalytic complexes were determined. The optimal conditions for oxidation were found.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
H. C. Godt, Jr., and J. F. Quinn, J. Am. Chem. Soc., 1956, 78, 1461.
V. I. Trubnikova, V. A. Preobrazhenskii, A. M. Gol'dman, M. S. Furman, and V. N. Kostina, Khim. Prom. [Chem. Indust.], 1970, No. 1, 12 (in Russian).
C. Venturello and M. Gambaro, J. Org. Chem., 1991, 56, 5924.
Y. Ishii, K. Yamawaki, T. Ura, H. Yamada, T. Yoshida, and M. Ogawa, J. Org. Chem., 1988, 53, 3587.
K. Sato, M. Aoki, J. Takagi, and R. Noyori, J. Am. Chem. Soc., 1997, 119, 12386.
S. E. Turnwald, M. A. Lorier, L. J. Wright, and M. R. Mucalo, J. Mater. Sci. Lett., 1998, 17, 1305.
I. Kozhevnikov, Catalysis for Fine Chemical Synthesis, Vol. 2, Catalysis by Polyoxometalates, John Wiley and Sons Ltd, Chichester, 2002, 201 pp.
B. N. Tyutyunnikov, Khimiya zhirov [Chemistry of Fats], Pishchevaya prom-st', Moscow, 1966, 632 pp. (in Russian).
C. Aubry, G. Chottard, N. Platzer, J.-M. Bregeault, R. Thouvenot, F. Chauveau, C. Huet, and H. Ledon, Inorg. Chem., 1991, 30, 4409.
C. Venturello and R. D'Aloisio, J. Org. Chem., 1988, 53, 1553.
M. N. Timofeeva, Z. P. Pai, A. G. Tolstikov, G. N. Kustova, N. V. Selivanova, P. V. Berdnikova, K. P. Brylyakov, A. B. Shangina, and V. A. Utkin, Izv. Akad. Nauk, Ser. Khim., 2003, 458 [Russ. Chem. Bull., Int. Ed., 2003, 52, 480].
V. A. Rabinovich and Z. Ya. Khavin, Kratkii khimicheskii spravochnik [Short Handbook of Chemistry], Khimiya, Leningrad, 1978, 392 pp. (in Russian).
S. S. Yufit, Mekhanizm mezhfaznogo kataliza [Mechanism of Phase-Transfer Catalysis], Nauka, Moscow, 1984, 264 pp. (in Russian).
B. Ying-li, Zh. Mei-juan, H. Hong-yu, W. Chang-ping, L. Wen-xing, and Zh. Kai-ji, React. Kinet. Catal. Lett., 2001, 72, 73.
E. Antonelli, R. D'Aloisio, M. Gambaro, T. Fiorani, and C. Venturello, J. Org. Chem., 1998, 63, 7190.
Author information
Authors and Affiliations
Additional information
__________
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 8, pp. 1794–1801, August, 2005.
Rights and permissions
About this article
Cite this article
Pai, Z.P., Tolstikov, A.G., Berdnikova, P.V. et al. Catalytic oxidation of olefins and alcohols with hydrogen peroxide in a two-phase system giving mono- and dicarboxylic acids. Russ Chem Bull 54, 1847–1854 (2005). https://doi.org/10.1007/s11172-006-0047-z
Received:
Revised:
Issue Date:
DOI: https://doi.org/10.1007/s11172-006-0047-z