Reaction Kinetics, Mechanisms and Catalysis

, Volume 124, Issue 2, pp 469–485 | Cite as

Phosphomolybdovanadic acid catalyzed oxidation of 2,6-dimethylphenol into para-quinone in a biphasic system

  • Yulia A. RodikovaEmail author
  • Elena G. Zhizhina
  • Zinaida P. Pai


In this paper, we disclose the results of our extended investigations on the reactivity of modified-type vanadium-containing heteropoly acids \({\text{H}}_{\text{a}} {\text{P}}_{\text{z}} {\text{Mo}}_{\text{y}} {\text{V}}_{{{\text{x}}^{\prime}}} {\text{O}}_{\text{b}}\) (HPA-x′) towards the oxidation of 2,6-dimethylphenol (2,6-Me2P). This reaction is of great value as an effective way to the corresponding 2,6-dimethyl-1,4-benzoquinone (2,6-Me2BQ), practically avoiding the formation of diphenoquinone, which is interesting from the standpoint of its potential application as a sensitizer and ‘platform molecule’. The overall process is based on two reactions: the oxidation of 2,6-Me2P by \({\text{V}}^{\text{V}} {\text{O}}_{2}^{ + } \leftrightarrow {\text{V}}^{\text{V}} {\text{ - HPA}}\) and the oxidation of reduced VIV-HPA ↔ VIVO2+ by dioxygen to the initial state. Special attention was given to the former process with regard to the influence of the reaction parameters on the product distribution. The desired quinone was efficiently synthesized in good yield (95%) at total substrate conversion, carrying out the oxidation in a biphasic water–trichloroethene system at 70 °C under nitrogen atmosphere in the presence of HPA-10′ solution (H17P3Mo16V10O89). The increase in vanadium content favored the selectivity of 2,6-Me2BQ due to faster electron transfer. The multicycle tests of catalyst showed its stability to V2O5·nH2O deposition.


Benzoquinones Heteropoly acids Homogeneous catalysis Selective oxidation Biphasic system 



This work was conducted within the Framework of Budget Project No. AAAA-A17-117041710081-1 for Boreskov Institute of Catalysis.

Supplementary material

11144_2018_1367_MOESM1_ESM.rar (836 kb)
Supplementary material 1 (RAR 836 kb)
11144_2018_1367_MOESM2_ESM.rar (701 kb)
Supplementary material 2 (RAR 700 kb)


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Copyright information

© Akadémiai Kiadó, Budapest, Hungary 2018

Authors and Affiliations

  1. 1.Department of Fine Organic Synthesis and Renewable Energy SourcesBoreskov Institute of Catalysis of the Siberian Branch of the Russian Academy of SciencesNovosibirskRussian Federation

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