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 condensation with 1,3-butadiene in the HPA solutions with no organic solvents yields 9,10-anthraquinone (AQ) mixed with tetrahydro-AQ (THA) and dihydro-AQ (DHA). However, AQ yield and its purity may be considerably improved by using water-mixable organic solvents, e.g., acetone, 1,4-dioxane, as well as high vanadium content HPA such as H15P4Mo18V7O89 and H17P3Mo16V10O89. Process optimization provides 70% yield of reaction product containing no less than 90% AQ.
Highlights
9,10-Anthraquinone (AQ) is a quite important product of organic synthesis [1]
Earlier [4,5] we suggested to use the aqueous solutions of Mo-V-P heteropoly acids (HPA), which are simultaneously acid catalysts and oxidizers, to produce AQ via 1,4-naphthoquinone reaction with 1,3-butadiene
As we have already mentioned [4,5], when we performed the one-pot process under P = 0.1 MPa and at T = 80 ̊C 90 ̊C without organic solvents or in the presence of solvents poorly mixing with water, we obtained the mixtures of 4 products, AQ content never being higher than 50%
Summary
Diene synthesis is known as one of industrial processes for producing AQ This method bases on the 1,4-naphthoquinone (NQ) reaction with 1,3-butadiene [1]. In the previous studies [4,5] butadiene reaction with NQ in the HPA solution is shown to yield the product mixtures containing AQ and its partially hydrogenated derivatives THA and 1,4-dihydroAQ (DHA). With this regard, in the present work we tried to optimize the onepot process to obtain practically pure AQ. We have specified conditions, allowing almost complete shift of the adduct oxidation towards the AQ synthesis
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