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

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DOI: 10.4236/mrc.2014.32008    3,527 Downloads   5,140 Views   Citations

ABSTRACT

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.

Conflicts of Interest

The authors declare no conflicts of interest.

Cite this paper

Gogin, L. and Zhizhina, E. (2014) One-Pot Production of Substituted Anthraquinones via the Diene Synthesis in the Presence of Mo-V-P Heteropoly Acid Solutions. Modern Research in Catalysis, 3, 575-61. doi: 10.4236/mrc.2014.32008.

References

[1] Gorelik, M.V. (1983) Chemistry of Anthraquinones and Their Derivatives. Khimia, Moscow.
[2] (2005) Anthraquinone Dyes and Intermediates. In: Ullmann’s Encyclopedia of Industrial Chemistry, Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.
[3] (2006) Anthraquinone. In: Kirk-Othmer Encyclopedia of Chemical Technology, 5th Edition, John Wiley & Sons, New York, 419-427.
[4] Ju, H.S., Ju, Y.J., Kim, J.E. and Won, J.I. (2001) Preparation of Napthoquinone and Anthraquinone Using Oxidizing Agent. KR Patent No. 2001004856.
[5] Ju, H.S., Ju, Y.J., Kim, J.E. and Won, J.I. (2000) Method of Manufacturing Anthraquinone from 1,4-Napthoquinone and 1,3-Butadiene. KR Patent No. 2000001821.
[6] (1942) Organic Syntheses. John Wiley & Sons, New-York.
[7] Kozhevnikov, I.V. (1998) Catalysis by Heteropoly Acids and Multicomponent Polyoxometal-lates in Liquid-Phase Reactions. Chemical Reviews, 98, 171-198. http://dx.doi.org/10.1021/cr960400y
[8] Zhizhina, E.G., Matveev, K.I. and Russkikh, V.V. (2004) 1,4-Naphtoand 9,10-Anthraquinone Catalytic Preparation by Diene Synthesis Reaction for Cellulose-Paper Industry. Khimiya v Interesakh Ustoichivogo Razvitiya, 12, 47-51.
[9] Zhizhina, E.G., Simonova, M.V., Odyakov, V.F. and Matveev, K.I. (2005) Catalytic Synthesis of 9,10-Anthraquinone in the Presence of Mo-V-Phosphoric Heteropoly Acids Solutions. Catalysis in Industry, 12-17.
[10] Zhizhina, E.G. and Odyakov, V.F. (2012) Aqueous Solutions of Mo-V-P Heteropoly Acids as Bifunctional Catalysts for Preparation of 9,10-Anthraquinone and Its Hydrogenated Derivatives. ChemCatChem, 4, 1405-1410.
http://dx.doi.org/10.1002/cctc.201200039
[11] Gogin, L.L., Zhizhina, E.G. and Pai, Z.P. (2013) Low-Waste One-Pot Process of Anthraquinone Production via Diene Synthesis in the Presence of Heteropoly Acids Solutions. Khimiya v Interesakh Ustoichivogo Razvitiya, 21, 123-127.
[12] Weygand-Hilgetag (1968) Methods of Experiment in Organic Chemistry. Khimia, Moscow.
[13] Odyakov, V.F., Zhizhina, E.G. and Maksimovskaya, R.I. (2008) Synthesis of Molybdovanadophos-Phoric Heteropoly Acid Solutions Having Modified Composition. Applied Catalysis A: General, 342, 126-130.
http://dx.doi.org/10.1016/j.apcata.2008.03.008
[14] Selling, A., Andersson, I., Grate, J.H. and Pettersson, L. (2000) A Potentiometric and (31P, 51V) NMR Study of the Aqueous Molybdovanadophosphate System. European Journal of Inorganic Chemistry, 2000, 1509-1521.
[15] Zhizhina, E.G., Odyakov, V.F. and Matveev, K.I. (1999) Thermochemical Study of Reduction and Oxidation Reactions of Molybdovanadophosphoric Heteropoly Acids in Aqueous Solutions. European Journal of Inorganic Chemistry, 1999, 1009-1014.
[16] Zhizhina, E.G., Simonova, M.V., Odyakov, V.F. and Matveev, K.I. (2004) Regeneration of Catalysts Based on Aqueous Solutions of Mo-V-P Heteropoly Acids. Khimiya v Interesakh Ustoichivogo Razvitiya, 6, 683-688.
[17] Kozhevnikov, I.V. and Matveev, K.I. (1982) Heteropoly Acids in Catalysis. Russian Chemical Reviews, 51, 1875-1896.

  
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