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

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 H 17 P 3 Mo 16...

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Bibliographic Details
Published in:Kinetics and catalysis 2019, Vol.60 (1), p.69-73
Main Authors: Gogin, L. L., Zhizhina, E. G., Pai, Z. P.
Format: Article
Language:English
Subjects:
Anthraquinones
Catalysis
Chemistry
Chemistry and Materials Science
Hexadiene
Oxidation
Physical Chemistry
Synthesis
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Summary: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 H 17 P 3 Mo 16 V 10 O 89 (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.
ISSN:0023-1584
1608-3210
DOI:10.1134/S0023158419010087