Catalytic Way of Transforming 2,3-Dimethylphenol to para-Quinone with the Use of Vanadium-Containing Heteropoly Acids Full article
| Journal |
Applied Catalysis A: General
ISSN: 0926-860X , E-ISSN: 1873-3875 |
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| Output data | Year: 2018, Volume: 549, Pages: 216-224 Pages count : 9 DOI: 10.1016/j.apcata.2017.09.022 | ||
| Tags | Benzoquinone, Biphasic system, Heteropoly acid, Homogeneous catalysis, Selective oxidation | ||
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| Affiliations |
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Funding (1)
| 1 | Federal Agency for Scientific Organizations | V.44.2.4. |
Abstract:
2,3-Dimethyl-p-benzoquinone (2,3-Me2BQ) is a valuable chemical that is applied as a soft oxidizing and dehydrogenating agent and also as a synthon in preparing different complex products including pharmaceutical and biochemical substances. Keggin- and modified-type aqueous solutions of Mo-V-phosphoric heteropoly acids (Mo-V-P HPAs) with the gross compositions H3+xPMo12-xVxO40 (HPA-x) and HaPzMoyVx’Ob (HPA-x’), respectively, possessing high oxidation potential and simplicity of regeneration can serve as effective soft oxidants for obtaining such para-quinone from 2,3-dimethylphenol (2,3-Me2P). The synthesized HPA catalysts with different vanadium content were characterized by a number of analysis techniques, such as 31P and 51V NMR spectroscopy, potentiometry, titrimetry, and pH measurement. It was found that the predominant formation of 2,3-Me2BQ instead of corresponding diphenoquinone (DPQ) at one-electron oxidation is achieved by a consecutive optimization of reaction conditions, the most important among them being organic solvent and molar ratio of vanadium(V) to substrate. As was shown, the substitution of HPA-x by HPA-x’ allows one to increase the quinone selectivity and to decrease the optimal molar ratio of vanadium(V) to substrate. The highest yield of the desired quinone (97%) at total substrate conversion was obtained by using the biphasic water-benzene system at molar vanadium(V) to substrate ratio of 12. The temperature of 50 °C and an inert atmosphere were established to be the optimal reaction conditions. The aqueous HPA-10’ solution including the highest content of VO2+ ions proved to be the most efficient catalyst among investigated HPAs. Carrying out catalyst regeneration at a separate stage provides the preservation of its activity and selectivity at the initial level for at least ten cycles.
Cite:
Rodikova Y.A.
, Zhizhina E.G.
, Pai Z.P.
Catalytic Way of Transforming 2,3-Dimethylphenol to para-Quinone with the Use of Vanadium-Containing Heteropoly Acids
Applied Catalysis A: General. 2018. V.549. P.216-224. DOI: 10.1016/j.apcata.2017.09.022 WOS Scopus РИНЦ ANCAN OpenAlex
Catalytic Way of Transforming 2,3-Dimethylphenol to para-Quinone with the Use of Vanadium-Containing Heteropoly Acids
Applied Catalysis A: General. 2018. V.549. P.216-224. DOI: 10.1016/j.apcata.2017.09.022 WOS Scopus РИНЦ ANCAN OpenAlex
Dates:
| Submitted: | Jul 21, 2017 |
| Accepted: | Sep 19, 2017 |
| Published online: | Oct 9, 2017 |
| Published print: | Jan 1, 2018 |
Identifiers:
| Web of science: | WOS:000417008800024 |
| Scopus: | 2-s2.0-85031304321 |
| Elibrary: | 31083109 |
| Chemical Abstracts: | 2017:1664777 |
| Chemical Abstracts (print): | 167:530580 |
| OpenAlex: | W2761192112 |