Designing a dimeric phthalocyanine-supported catalyst for the selective oxidation of aromatic compounds |
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| Affiliation: | 1. Laboratoire de Chimie et Physique Approche Multi-échelle de Milieux Complexes (LCP-A2MC), ICPM, Département de Chimie, Université de Lorraine, 1, Bd Arago, Metz-Technopôle, 57078 Metz, France;2. Université de Bourgogne Franche-Comté, Team ‘Biochemistry of the Peroxisome, Inflammation and Lipid Metabolism’ EA 7270/Inserm, Faculté des Sciences Gabriel, 6 Bd Gabriel, 21000 Dijon, France;3. Department of Chemistry, College of Sciences, Shiraz University, Shiraz 71454, Iran;1. Institute of Animal Reproduction and Food Research, Polish Academy of Sciences, Tuwima 10, 10-748 Olsztyn, Poland;2. Institute of Biochemistry and Biophysics, Polish Academy of Sciences, Pawińskiego 5A, 02-106 Warsaw, Poland;3. University of Leuven, Department of Chemistry, Celestijnenlaan 200F, B-3001 Leuven, Belgium;1. Department of Chemistry, ACS College of Engineering, Bangalore 560074, India;2. Department of Studies in Chemistry, Bangalore University, Bangalore 560001, India;1. Chemistry Department, University of Education, The University of DaNang, Ton Duc Thang 459, Da Nang, Viet Nam;2. Molecular Design and Synthesis, Department of Chemistry, KU Leuven, Celestijnenlaan 200F, B-3001 Leuven, Belgium;3. Department of Cellular and Molecular Medicine, KU Leuven, Herestraat 49, Box 901, 3000 Leuven, Belgium;4. Belarusian State Technological University, Physics Department, Sverdlov Str., 13a, Minsk 220006, Belarus |
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| Abstract: | The synthesis of new modified phthalocyanine-supported catalysts has been designed in order to stabilise more active and selective dimeric form by the covalent link of two phthalocyanine molecules through N,N′-diethyl-1,3-propanediamine spacer. The catalytic performance of these modified supported catalysts was tested for the aromatic oxidation of 2,3,6-trimethylphenol (TMP), naphthalene, 2-methylnaphthalene (2MN) and 2,3-dimethylnaphthalene and compared with that of iron phthalocyanine-supported catalysts having SO3H, SO2OSiPh3 and SO2NiPr2 substituents on the grafted phthalocyanine. Diamine modified catalyst was more active and selective in the oxidation of the above substrates to corresponding quinones. Trimethyl-1,4-benzoquinone (precursor of vitamin E) was obtained with 84 % yield at 96 % conversion of TMP. More demanding oxidation of 2MN afforded 34 % yield of 2-methyl-1,4-naphthoquinone (vitamin K3). |
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