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Prospects of application of Mo–V-phosphoric heteropolyacid solutions as bifunctional catalysts for syntheses of anthraquinones and their substituted derivatives

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Abstract

The acid-catalyzed condensation of 1,3-butadienes with p-quinones and oxidation of the obtained adducts can be carried out as one-pot process in the presence of aqueous solutions of Mo–V–P-heteropolyacids (HPA) of the general composition HaPzMoyVxOb. These solutions act as bifunctional catalysts, since they simultaneously behave as strong Brönsted acids and fairly strong reversible oxidants. The condensation of 1,4-naphthoquinone (NQ) with 1,3-butadiene in solutions of high-vanadium HPA of the empirical compositions H15P4Mo18V7O89 and H17P3Mo16V10O89 in the presence of water-miscible organic solvents (acetone, 1,4-dioxane) affords 9,10-anthraquinone in a yield of ~70% and purity up to 97% at a complete conversion of NQ. Under similar conditions, the reactions of NQ and substituted 1,3-butadienes afford substituted anthraquinones in the yields up to 90% and purity up to 99%. The catalysts are regenerated with oxygen in an individual step and can be reused.

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Authors and Affiliations

  1. G. K. Boreskov Institute of Catalysis, Russian Academy of Sciences, 5 prosp. Akad. Lavrent’eva, 630090, Novosibirsk, Russian Federation

    L. Gogin, E. G. Zhizhina, Z. P. Pai & V. N. Parmon

  2. Novosibirsk State University, 2 ul. Pirogova, 630090, Novosibirsk, Russian Federation

    V. N. Parmon

Authors
  1. L. Gogin
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  2. E. G. Zhizhina
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  3. Z. P. Pai
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  4. V. N. Parmon
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Correspondence to L. Gogin.

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Dedicated to Academician of the Russian Academy of Sciences N. S. Zefirov on the occasion of his 80th birthday.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 9, pp. 2069–2075, September, 2015.

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Gogin, L., Zhizhina, E.G., Pai, Z.P. et al. Prospects of application of Mo–V-phosphoric heteropolyacid solutions as bifunctional catalysts for syntheses of anthraquinones and their substituted derivatives. Russ Chem Bull 64, 2069–2075 (2015). https://doi.org/10.1007/s11172-015-1119-8

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  • DOI: https://doi.org/10.1007/s11172-015-1119-8

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