Aerobic Oxidation of Dihydroxyarenes Substrates Catalyzed by Polymer- Supported RuII-Pheox/Silica-Gel: A Beneficial Route for Purification of Industrial Water

Page: [236 - 243] Pages: 8

  • * (Excluding Mailing and Handling)

Abstract

A broad class of dihydroxyarenes were easily oxidized by aerobic oxygen to quinone products in excellent yields under the catalytic effect of polymer-supported RuII-Pheox/silica-gel catalyst. By using this combined catalyst, hydroquinone and catechol derivatives with electron-donating groups were easily oxidized by molecular oxygen to quinone products in 90% to >99% yield, while in the case of electron-withdrawing group, only 70% was obtained. The biologically useful 1,4-Naphthoqinone products were obtained in 83% to 90%. The catalyst was easily obtained and reused many times without a significant decrease in reactivity. Interestingly, a sample of industrial water contaminated with phenolic compounds was subjected to aerobic oxidation by using this catalyst, and the resultant quinones were detected within one day and the catalyst was removed and reused several times with different contaminating samples with the same efficiency. Other catalytic oxidations by using this promising catalyst were investigated.

Keywords: Polymer-supported catalysts, quinones, dihydroxy arenes, aerobic oxidation, ruthenium catalyst.

Graphical Abstract

[1]
Wu, W.E.; Ge, H.G.; Zhang, K.F. wastewater biological treatment technology, 2003.
[2]
Leahy, J.G. Microbiol. Rev., 1990, 54, 305-315.
[http://dx.doi.org/10.1128/MMBR.54.3.305-315.1990] [PMID: 2215423]
[3]
Patai, S., Ed.; The Chemistry of Quinonoid Compounds, Part 1; Wiley: New York, 1974. Patai, S., Ed.; The Chemistry of Quinonoid Compounds, Part 2; Wiley: New York, , 1988.
[4]
Miyamura, H.; Shiramizu, M.; Matsubara, R.; Kobayashi, S. Angew. Chem. Int. Ed., 2008, 47, 8093-8095.
[http://dx.doi.org/10.1002/anie.200802192]
[5]
(a) Villemin, D.; Hammadi, M.; Hachemi, M. Synth. Commun., 2002, 32, 1501-1516.
[http://dx.doi.org/10.1081/SCC-120004139]
(b) Muralidharan, S.; Freiser, H. J. Mol. Catal., 1989, 50, 181-193.
[http://dx.doi.org/10.1016/0304-5102(89)85061-8]
(c) Van Sickle, D.E.; Myers, G.L.; Nottingham, W.D.; Jones, G.C.U.S.U.S. Patent 5118823 1992.
[6]
Abu-Elfotoh, A-M.; Phomkeona, K.; Shibatomi, K.; Iwasa, S. Angew. Chem. Int. Ed., 2010, 49, 8439-8443.
[http://dx.doi.org/10.1002/anie.201002240]
[7]
Abu-Elfotoh, A-M.; Tsuzuki, K.; Nguyen, T.B.; Chanthamath, S.; Shibatomi, K.; Iwasa, S. Tetrahedron, 2013, 69, 8612-8617.
[http://dx.doi.org/10.1016/j.tet.2013.07.069]
[8]
Pinho, B.R.; Sousa, C.; Oliveira, J.M.A.; Valentao, P.; Andrade, P.B. Naphthoquinones’ biological activities and toxicological effects.Bioactive compounds: Type, biological activities and health effects; Bitterlich, A; Fischl, S., Ed.; Nova Science Publishers: New York, 2012, pp. 181-218.
[9]
Kim, S.; Kim, D. Park. J. Adv. Synth. Catal., 2009, 351, 2573-2578.
[http://dx.doi.org/10.1002/adsc.200900347]
[10]
(a) Shimizu, M.; Hayakawa, T.; Hayakawa, T.; Takehira, K. Tetrahedron Lett 1989, 30, 471-474.
[http://dx.doi.org/10.1016/S0040-4039(00)95231-6]
(b) Korenskii, V.I.; Skobeleva, V.D.; Kharchuk, V.G.; Kolenko, I.P.; Volkov, V.L.; Zakharova, G.S.; Vinogradova, V.N.J. Gen. Chem. USSR, 1985, 55, 1750-1755.
[11]
Takata, T.; Tajima, R.; Ando, W. J. Org. Chem., 1983, 48, 4764-4766.
[http://dx.doi.org/10.1021/jo00172a059]