Abstract
Abstract The results of the studies on the influence of the phase transfer catalyst on the epoxidation of (Z,E,E)-1,5,9-cyclododecatriene (CDT) to 1,2-epoxy-5,9-cyclododecadiene (ECDD) in the H2O2/H3PW12O40 system by a method of phase transfer catalysis (PTC) were presented. The following quaternary ammonium salts were used as phase transfer catalysts: methyltributylammonium chloride, (cetyl)pyridinium bromide, methyltrioctylammonium chloride, (cetyl)pyridinium chloride, dimethyl[dioctadecyl(76%)+dihexadecyl(24%)] ammonium chloride, tetrabutylammonium hydrogensulfate, didodecyldimethylammonium bromide and methyltrioctylammonium bromide. Their catalytic activity was evaluated on the basis of the degree of CDT and hydrogen peroxide conversion and the selectivities of transformation to ECDD in relation to consumed CDT and hydrogen peroxide. The most effective PT catalysts were selected based on the obtained results. Among the onium salts under study, the epoxidation of CDT with hydrogen peroxide proceeds the most effectively in the presence of methyltrioctylammonium chloride (Aliquat® 336) and (cetyl)pyridinium chloride (CPC). The relatively good results of CDT epoxidation were also achieved in the presence of Arquad® 2HT and (cetyl)pyridinium bromide
Highlights
A search of economically effective and environmentally friendly methods of production is one of the fundamental objectives of modern organic synthesis[1]
The objective of this work was to investigate the catalytic activity of selected ammonium salts in the epoxidation of (Z,E,E)-1,5,9-cyclododecatriene (CDT) to 1,2-epoxy-5,9-cyclododecadiene (ECDD) in the H2O2/H3PW12O40 system by the phase transfer catalysis (PTC) method
The epoxidation process of CDT with 30% hydrogen peroxide under the PTC conditions was carried out according to the following procedure: a 25 cm[3], three necked flask (1) fitted with a thermometer (2) and mechanical stirrer (3) was charged with a determined amount of solid H3O40PW12·xH2O and with a 30% aqueous solution of hydrogen peroxide
Summary
A search of economically effective and environmentally friendly methods of production is one of the fundamental objectives of modern organic synthesis[1]. This relates to the processes for the preparation of epoxides. As with the application of organic peracids as the oxidant, it is associated with a relative large hazard resulting from the explosive properties of these compounds For these reasons, new methods for the preparation of epoxides that could limit or eliminate toxic and/or dangerous oxidants are required[1]. New methods for the preparation of epoxides that could limit or eliminate toxic and/or dangerous oxidants are required[1] In this context, hydrogen peroxide deserves particular attention. It possesses a high content of potentially active oxygen and the methods of its production ensure its high purity and moderate price
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