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Synthesis of 1,4-Dimethyl-9,10-Anthraquinone from 1,4-Naphthoquinone and 2,4-Hexadiene in the Presence of Heteropoly Acids

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Abstract

The synthesis of 1,4-dimethyl-9,10-anthraquinone (DMAQ) from 1,4-naphthoquinone and 2,4‑hexadiene was studied based on a new one-step method developed by the authors for the synthesis of substituted anthraquinones. A solution of high-vanadium heteropoly acid with the empirical formula H17P3Mo16V10O89 (HPA-10) was used as a bifunctional (acid and oxidation) catalyst. It was found that a reaction with 2,4-hexadiene, unlike other methylbutadienes, does not proceed so smoothly, and it leads to the formation of a mixture of DMAQ, its dihydro derivative, and tarry products. Possible reasons for the results obtained are discussed.

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ACKNOWLEDGMENTS

This work was performed at the Boreskov Institute of Catalysis, Siberian Branch, Russian Academy of Sciences in accordance with a state contract (project no. AAAA-A17-117041710081-1).

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Authors and Affiliations

  1. Boreskov Institute of Catalysis, Siberian Branch, Russian Academy of Sciences, 630090, Novosibirsk, Russia

    L. L. Gogin, E. G. Zhizhina & Z. P. Pai

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  1. L. L. Gogin
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  2. E. G. Zhizhina
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  3. Z. P. Pai
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Correspondence to L. L. Gogin.

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Translated by V. Makhlyarchuk

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Gogin, L.L., Zhizhina, E.G. & Pai, Z.P. Synthesis of 1,4-Dimethyl-9,10-Anthraquinone from 1,4-Naphthoquinone and 2,4-Hexadiene in the Presence of Heteropoly Acids. Kinet Catal 60, 69–73 (2019). https://doi.org/10.1134/S0023158419010087

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  • DOI: https://doi.org/10.1134/S0023158419010087

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