Catalytic oxidation of α-alkenes with hydrogen peroxide to carboxylic acids in the presence of peroxopolyoxotungstate complexes

• Published in: Catalysis communications Vol. 88; pp. 45 - 49
• Main Authors: Pai, Z.P., Selivanova, N.V., Oleneva, P.V., Berdnikova, P.V., Beskopyl'nyi, A.M.
• Format: Journal Article
• Language: English
• Published: Elsevier B.V 05-01-2017
• Subjects: Alpha-alkenes; Carboxylic acids; Peroxotungstate complexes; Phase-transfer catalysis; Quaternary ammonium cations; Alpha-alkenes; Carboxylic acids; Phase-transfer catalysis; Quaternary ammonium cations; Peroxotungstate complexes
• ISSN: 1566-7367; 1873-3905
• DOI: 10.1016/j.catcom.2016.09.019

Fine organic synthesis investigation has been performed, focusing on the possibility of efficient oxidation of α-alkenes by hydrogen peroxide under conditions of phase transfer catalysis using bifunctional metal complex catalysts based on peroxotungsten compounds of general formula Q3{PO4[WO(O2)2]4}, where Q is organic cation containing quaternary nitrogen atom.
Catalysts screening has been done at oxidation of octene-1, decene-1 and dodecene-1 by 30% aqueous hydrogen peroxide to obtain carboxylic acids: heptanoic, nonanoic and undecanoic acids being of importance since used as precursors in the synthesis of various organic and biologically active compounds. This approach to the synthesis of carboxylic acids may be of interest for the processes of “green chemistry” occurring under mild conditions (Т<100°С, Р – atm) in one stage without organic solvents, and providing high target product yields (86–97%).
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•α-Alkenes were oxidized in a two-phase system by H2O2 in the presence of metal complex catalysts.•Carboxylic acids (С7, С9 and С11) were found to form with high yields (86–97%).•This approach as for carboxylic acids synthesis may be of interest for “green chemistry” processes.