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Modern Research in Catalysis 2013年第3期2卷 90-92页

作者： Leonid Gogin elena zhizhina Boreskov Institute of Catalysis Novosibirsk Russia

Acid-catalytic 1,3-butadiene condensation with para-quinones followed by the obtained product oxidation may be performed in one stage as one-pot process, if assisted by the aqueous solutions of Mo-V-P heteropoly acids with a composition of HaPzMoyVxOb. 1,4-naphthoquinone condensation with 1,3-butadiene in the HPA solutions with no organic solvents yields 9,10-anthraquinone (AQ) mixed with tetrahydro-AQ (THA) and dihydro-AQ (DHA). However, AQ yield and its purity may be considerably improved by using water-mixable organic solvents, e.g., acetone, 1,4-dioxane, as well as high vanadium content HPA such as H15P4Mo18V7O89 and H17P3Mo16V10O89. Process optimization provides 70% yield of reaction product containing no less than 90% AQ.

关键词： 9 10-Anthraquinone Mo-V-P Heteropoly Acids Diene Synthesis Organic Solvents

One-Pot Production of Substituted Anthraquinones via the Diene Synthesis in the Presence of Mo-V-P Heteropoly Acid Solutions

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Modern Research in Catalysis 2014年第2期3卷 575-61页

作者： Leonid Gogin elena zhizhina Boreskov Institute of Catalysis Novosibirsk Russia

Acid-catalytic 1,3-butadiene condensation with para-quinones followed by the obtained product oxidation may be performed in one stage as one-pot process, if assisted by the aqueous solutions of Mo-V-P heteropoly acids with a composition of HaPzMoyVxOb. 1,4-naphthoquinone (NQ) condensation with 1,3-butadiene in HPA solutions (brutto-composition H15P4Mo18V7O89 and H17P3Mo16V10O89) in the presence of hydrophylic organic solvents (acetone, 1,4-dioxane) provides 70% yield of 9,10-anthraquinone (AQ) containing no less than 90% AQ. In the same conditions reaction NQ with substituted 1,3-butadienes in the presence of the aqueous H17P3Mo16V10O89 (HPA-10) solution allows to prepare substituted AQ with yield up to 90% and purity up to 99%. The catalysts are regenerated by oxygen in separate stage and are reused.

关键词： Substituted 9 10-Anthraquinones Diene Synthesis Mo-V-P Heteropoly Acids Bifunctional Catalysts

Trimethyl-1,4-Benzoquinone Synthesis via 2,3,6-Trimethylphenol Catalytic Oxidation by Oxygen in the Presence of Non-Keggin-Type Mo-V-Phosphoric Heteropoly Acid Solutions

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Journal of Chemistry and Chemical Engineering 2013年第9期7卷 808-820页

作者： Yulia Anatohevna Rodlkova elena Georgievna zhizhina Department of Catalytic Processes of Fine Organic Synthesis Boreskov Institute of Catalysis Siberian Branch of Russian Academyof Sciences Novosibirsk 630090 Russia

In the present study, the modified （non-Keggin-type） aqueous solutions of Mo-V-phosphoric heteropoly acids HaPzMoyVx,Oh （HPA-x＇） were applied as homogeneous catalysts for the two-stage oxidation of TMP （2,3,6-trimethylphenol） by oxygen into TMQ （2,3,5-trimethyl-l,4-benzoquinone）, the latter being the key intermediate in the synthesis of vitamin E. The TMQ yield was analyzed regarding solvent type, reaction temperature, molar HPA-x ＇：TMP ratio, and the concentration of vanadium （V） in the HPA-x＇ solution. The TMQ yield was found to depend strongly on the catalyst redox potential and the rate of electron transfer. The results obtained enabled to establish the optimal reaction conditions as well as to suggest the reaction mechanism. In the target reaction, which proceeds in the two-phase system, the TMQ yield is higher than 99%. After phase separation, the catalyst is rapidly regenerated by oxygen and reused.

关键词： Trimethyl-1 4-benzoquinone catalytic oxidation heteropoly acid homogeneous catalysis.

One-Pot Process of Naphthoquinones Synthesis from Hydroquinone in the Presence of Solutions of Mo-V-P Heteropolyacids as Bifunctional Catalysts

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Modern Research in Catalysis 2019年第1期8卷 1-9页

作者： Leonid L. Gogin elena G. zhizhina Zinaida P. Pai Federal Research Center Boreskov Institute of Catalysis Novosibirsk Russia

1,4-Naphthoquinones (NQ) is a class of organic compounds with a number of important properties. However, the existing methods of their synthesis either give a low NQ yield or multistage and require a lot of time. In the present work new one-pot process of NQ synthesis from hydroquinone (HQ) and substituted 1,3-dienes at room temperature is proposed. The solution of heteropolyacid H7PMo8V4O40 (HPA-4) is used as a bifunctional (acid and redox) catalyst for this process. The influence of a number of factors on key process parameters has been studied. It is demonstrated that unsubstituted and a number of alkyl substituted NQ with the yields of 50% - 80% and purity of 92% - 99% can be obtained by this method. The results obtained allow to significantly simplify the synthesis of NQ directly from HQ in comparison with the described similar methods.

关键词： Hydroquinone Naphthoquinones Heteropolyacid Diene Synthesis