Olefin epoxidation with H2O2 in the presence of Mn(II) dicarboxylate coordination polymer catalysts |
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Authors: | Hassan Hosseini Monfared Azar Mohajeri Ali Morsali and Christoph Janiak |
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Institution: | (1) Department of Chemistry, Zanjan University, 45195-313, Zanjan, Islamic Republic of Iran;(2) Department of Chemistry, Faculty of Sciences, Tarbiat Modares University, P.O. Box 14115-175, Tehran, Islamic Republic of Iran;(3) Institut f?r Anorganische und Analytische Chemie, Universit?t Freiburg, Albertstr. 21, 79104 Freiburg, Germany |
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Abstract: | Abstract The Mn(II) dicarboxylate coordination polymers Mn(μ-terephthalate)(H2O)2]
n
, Mn(μ-oxalate)(H2O)2]
n
, and Mn(μ-d-(−)-tartrate)]
n
were prepared in water and characterized by FT-IR spectroscopy and CHN analysis. Particles of the terephthalate catalyst
were also synthesized, by reaction of terephthalic acid and MnCl2·4H2O by a sonochemical method. The catalytic potential of these coordination polymers as slow-release sources of catalytically
active Mn species was tested in the oxidation of cyclooctene to its epoxide in acetonitrile, using hydrogen peroxide as oxygen
source. For the terephthalate species the catalytic activity was found to increase with increasing dielectric constant and
dipole moment of the solvent (being highest in acetonitrile), with reaction temperature to a maximum at 60 °C, and with an
imidazole co-catalyst (highest activity found for a imidazole-to-catalyst molar ratio of 20:1). Good activity with more than
64% conversion in 24 h was obtained for epoxidation of cyclooctene and cyclohexene, whereas low yields only were obtained
from aryl-substituted olefins. Some exo versus endo regioselectivity was found for norbornene. |
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Keywords: | |
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