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One-pot production of substituted anthraquinones via the diene synthesis in the presence of Mo-VP heteropoly acid solutions
Abstract
Acid-catalyzedcondensationofsubstituted1,3-butadienewith p-uinones
and oxidation of resulting adducts was carried out as a single process in the presence of aqueous solutions of Mo-VP heteropoly acids (HPAs) of the total composition HaPzMoyVxOb. Th bifunctional catalytic properties, being both strong Brшnsted acids and quite strong reversible oxidants. Condensation of 1,4-naphthoquinone (NQ) with 1,3-butadiene in a solution of high-vanadium HPAs with total compositions H15P4Mo18V7O89 and H17P3Mo16V10O89 in the presence of water-miscible organic solvents (acetone, 1,4-dioxane) results in a formation of 9,10-anthraquinone (AQ) with a yield of about 70 % and a selectivity up to 97 % at complete conversion of NQ. The reaction between NQ and substituted 1,3-butadiene under analogous conditions produces substituted anthraquinones with the yields up to 90 % and selectivities up to 99 %. Catalysts are regenerated with oxygen in a separate step and can be used repeatedly.
About the Authors
L. L. Gogin
Институт катализа им. Г.К. Борескова СО РАН, г. Новосибирск
Russian Federation
Russian Federation
E. G. Zhizhina
Институт катализа им. Г.К. Борескова СО РАН, г. Новосибирск
Russian Federation
Russian Federation
References
1. Полотнюк О.-В.Я. // Катализ в промышленности. 2013. № 5. С. 59.
2. Anthraquinone Dyes and Intermediates, in Ullmann’s Encyclopedia of Industrial Chemistry, Vol. A, 2007.
3. Anthraquinone, in Kirk-Othmer Encyclopedia of chemical technology, 5th Ed, Vol. 2, 2006.
4. Chang J.B., Yuk S.B., Park J.S., Kim J.P. // Dyes and Pygments. 2012. Vol. 98. Is. 1. P. 737.
5. Valim R.B., Reis R.M., Castro P.S., Lima A.S., Rocha R.S., Bertotti M., Lanza M.R.V. // Carbon. 2013. Vol. 61. P. 236.
6. Abdel-Yamid A.M., Solbiati J.O., Cann I.R.O. // Advances in Appl. Microbiology. 2013. Vol. 82. P. 1.
7. Zhang C., Kim S.K. // Advances in Food and Nutrition. 2012. Vol. 65. P. 415.
8. Caldiran Z., Deniz A.R., Coskun M., Ayudogan S., Yesildaz A., Ekinei D. // J. Alloys and Compounds. 2014. Vol. 584. P. 652.
9. Патент 2001004856 Южной Кореи. Preparation of Naphtoquinone and Anthraquinone Using Oxidizing Agent / H.S. Ju, Y.J. Ju, J.E. Kim, J.I. Won. 2001.
10. Патент 2000001821 Южной Кореи. Method of Manufacturing Anthraquinone from 1,4-Naphtoquinone and 1,3-Butadiene / H.S. Ju, Y.J. Ju, J.E. Kim, J.I. Won. 2000.
11. Синтезы органических препаратов. Сб. 3. М.: Изд-во Иностранной литературы, 1952.
12. Kozhevnikov I.V. // Chem. Rev. 1998. Vol. 98. P. 171.
13. Zhizhina E.G., Simonova M.V., Odyakov V.F., Matveev K.I. // Appl. Catal. A: General. 2007. Vol. 319. P. 91.
14. Жижина E.Г., Симонова M.В., Одяков В.Ф. // Кинетика и катализ. 2008. Т. 49. С. 773.
15. Жижина E.Г., Матвеев К.И., Русских В.В. // Химия в интересах устойчивого развития. 2004. Т. 12. С. 47.
16. Жижина E.Г., Симонова M.В., Русских В.В., Матвеев К.И. // Катализ в промышленности. 2005. № 1.
17. С. 12.
18. Zhizhina E.G., Odyakov V.F. // ChemCatChem. 2012. Vol. 4. P. 1405.
19. Гогин Л.Л., Жижина Е.Г., Пай З.П. // Химия в интересах устойчивого развития. 2013. Т. 21. С. 123.
20. Кожевников И.В., Матвеев К.И. // Успехи химии. 1982. Т. 51. Вып. 11. С. 1875.
21. Вейганд-Хильгетаг. Методы эксперимента в органической химии. М.: Химия, 1968.
22. Odyakov V.F., Zhizhina E.G., Maksimovskaya R.I. //Applied Catalysis A: General. 2008. Vol. 342. P. 126.
23. Zhizhina E.G., Odyakov V.F., Matveev K.I. // Eur. J. Inorganic Chemistry. 1999. №. 6. Р. 1009.
24. Selling A., Andersson I., Grate J.H., Pettersson L. // Eur. J. Inorg. Chem. 2000. Vol. 7. P. 1509.
25. Жижина E.Г., Симонова M.В., Одяков В.Ф., Матвеев К.И. // Химия в интересах устойчивого развития.
26. Т. 6. С. 683.
27. Pagan I. // Chem.Biol.Interact. 2001. Vol. 135—136. P. 155.
Review
For citations:
Gogin L.L., Zhizhina E.G. One-pot production of substituted anthraquinones via the diene synthesis in the presence of Mo-VP heteropoly acid solutions. Kataliz v promyshlennosti. 2014;(4):33-38. (In Russ.)
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