Selective Oxidation of Pseudocumene and 2-Methylnaphthalene with Aqueous Hydrogen Peroxide Catalyzed by γ-Keggin Divanadium-Substituted Polyoxotungstate Full article
| Journal |
Journal of Organometallic Chemistry
ISSN: 0022-328X |
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| Output data | Year: 2015, Volume: 793, Pages: 210-216 Pages count : 7 DOI: 10.1016/j.jorganchem.2015.04.020 | ||||
| Tags | 2-Methylnaphthalene, Homogeneous catalysis, Hydrogen peroxide, Pseudocumene, Selective aromatic oxidation, Vanadium | ||||
| Authors |
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| Affiliations |
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Funding (2)
| 1 | Russian Foundation for Basic Research | 14-03-31431 |
| 2 | Russian Foundation for Basic Research | 13-03-12042 |
Abstract:
The catalytic performance of a γ-Keggin divanadium-substituted phosphotungstate, (Bu4N)4[γ-PW10O38V2(μ-O)(μ-OH)], has been evaluated in the selective oxidation of 1,2,4-trimethylbenzene (pseudocumene, PC) and 2-methylnaphthalene with the green oxidant, 35% aqueous hydrogen peroxide. Under conditions of H2O2 deficiency ([PC]/[H2O2] = 17–22), PC oxidation proceeded with unusually high chemo- and regioselectivity, producing exclusively 2,4,5-trimethylphenol (2,4,5-TMP) and 2,3,5-TMP in a molar ratio of 7.3/1 and a yield of 73% based on the oxidant. Isomeric 2,3,6-trimethylphenol was found in trace amounts. Under conditions of H2O2 excess ([H2O2]/[PC] = 8), 2,3,5-trimethyl-1,4-benzoquinone (TMBQ, vitamin E key intermediate) formed with 41% selectivity at 41% substrate conversion. Atypical regioselectivity was also found in the oxidation of 2-methylnaphthalene which gave predominantly 6-methyl-1,4-naphthoquinone (6-MNQ) rather than isomeric 2-MNQ. The ratio between the isomers could be altered by varying the catalyst and oxidant amounts.
Cite:
Zalomaeva O.V.
, Evtushok V.Y.
, Maksimov G.M.
, Kholdeeva O.A.
Selective Oxidation of Pseudocumene and 2-Methylnaphthalene with Aqueous Hydrogen Peroxide Catalyzed by γ-Keggin Divanadium-Substituted Polyoxotungstate
Journal of Organometallic Chemistry. 2015. V.793. P.210-216. DOI: 10.1016/j.jorganchem.2015.04.020 WOS Scopus РИНЦ ANCAN OpenAlex
Selective Oxidation of Pseudocumene and 2-Methylnaphthalene with Aqueous Hydrogen Peroxide Catalyzed by γ-Keggin Divanadium-Substituted Polyoxotungstate
Journal of Organometallic Chemistry. 2015. V.793. P.210-216. DOI: 10.1016/j.jorganchem.2015.04.020 WOS Scopus РИНЦ ANCAN OpenAlex
Dates:
| Submitted: | Dec 30, 2014 |
| Accepted: | Apr 7, 2015 |
| Published online: | Apr 23, 2015 |
| Published print: | Sep 1, 2015 |
Identifiers:
| Web of science: | WOS:000360026000024 |
| Scopus: | 2-s2.0-84939573570 |
| Elibrary: | 24413057 |
| Chemical Abstracts: | 2015:720663 |
| Chemical Abstracts (print): | 163:283016 |
| OpenAlex: | W2027636393 |