Clean and Selective Oxidation of Alcohols with Oxone and Phase-Transfer Catalysts in Water
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lean and Selective Oxidation of Alcohols with Oxone and Phase-Transfer Catalysts in Water Y. X. Yanga,b,*, M. Kanga,b, X. Q. Ana,b, W. Zenga,b, Z. W. Yanga,b, and H. C. Maa,b a
Key Laboratory of Eco-functional Polymer Materials of the Ministry of Education, Northwest Normal University, Lanzhou, Gansu, 730070 China b
Key Laboratory of Eco-environmental Polymer Materials, College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou, Gansu, 730070 China *e-mail: [email protected] Received May 20, 2020; revised June 1, 2020; accepted June 14, 2020
Abstract—A new, simple, metal-free, and eco-friendly procedure has been proposed for the oxidation of alcohols with Oxone (potassium peroxymonosulfate) in water in the presence of six phase-transfer catalysts (PTC). Phase-transfer catalysts were found to display high catalytic activity in water solution. Furthermore, the oxidation of alcohols was also carried out with relatively good conversion and selectivity in water without any catalyst. Keywords: alcohols, oxidation, phase-transfer catalyst, aldehydes, ketones
DOI: 10.1134/S1070428020100206 INTRODUCTION The oxidation of alcohols to the corresponding carbonyl compounds is a fundamental transformation in organic synthesis and is of major importance in both laboratory and industrial synthetic chemistry [1–3]. The oxidation of alcohols was traditionally carried out with the use of large amounts of noxious transition metal compounds such as chromates and permanganates [4, 5] or organic solvent [6, 7] or complicated reaction conditions were required [8–10]. In an attempt to provide a more environmentally benign process for alcohol oxidation, a variety of catalytic oxidation procedures using water as the only solvent have been investigated [11–15]. Bolm et al. [16] presented a metal-free oxidation system for the oxidation of alcohols using TEMPO/Oxone® in the presence of a catalytic amount of Bu4NBr. Surendra et al. [17, 18] reported a transition metal-free catalytic system for the oxidation of alcohols with o-iodoxybenzoic acid (IBX) or N-bromosuccinimide (NBS) catalyzed by β-cyclodextrin in aqueous acetone. Thottumkara et al. [19] reported a highly efficient oxidation of alcohols using IBX/Oxone® oxidation system in aqueous acetonitrile. Wu et al. [20] reported AlCl3/Oxone oxidation of alcohols in aqueous medium to attain excellent conversion and selectivity. Moriyama et al. [21] described a halidecatalyzed selective oxidation of alcohols with KBr/Oxone in aqueous acetone. Some of these pro-
cesses also generated equivalent amounts of metal waste, which are environmentally undesirable. Therefore, development of green, selective, and efficient catalysts for the oxidation of alcohols is important for both economic and environmental reasons. Oxone is a white crystalline solid which is easy to handle, nontoxic, soluble in water, cheap, and stable. Therefore, it has received much attention in the field of oxidation of alcohols [22–24]. Phase-transfer catalysts (PTC) facilitate reactant transport from
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