4.2 Article

Epoxidation of 1,5,9-cyclododecatriene with hydrogen peroxide under phase-transfer catalysis conditions: influence of selected parameters on the course of epoxidation

Journal

REACTION KINETICS MECHANISMS AND CATALYSIS
Volume 132, Issue 2, Pages 983-1001

Publisher

SPRINGER
DOI: 10.1007/s11144-021-01960-7

Keywords

1,5,9-Cyclododecatriene; Epoxidation; 1,2-Epoxy-5,9-cyclododecadiene; Hydrogen peroxide; Phase-transfer catalysis (PTC)

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This study investigates the epoxidation of 1,5,9-cyclododecatriene using hydrogen peroxide as the oxidizing agent under phase transfer catalysis conditions. The highest yield of 1,2-epoxy-5,9-cyclododecadiene is achieved at 54.9 mol% with the conversion of CDT reaching 72.3 mol%. Further research is needed to develop a more efficient and environmentally friendly method for obtaining this compound.
This work presents the studies on the epoxidation of 1,5,9-cyclododecatriene (CDT) with hydrogen peroxide as the oxidizing agent, under conditions of the phase transfer catalysis (PTC), and with the following catalytic system: H2WO4/H3PO4/[CH3(CH2)(7)](3)CH3N+HSO4- (compounds were mixed at the ratio of 2:1:1). The influence of the following parameters on the course of this process was investigated: catalyst content, molar ratio of H2O2:CDT, temperature and type of solvent. The highest yield of 1,2-epoxy-5,9-cyclododecadiene (ECDD) (54.9 mol%), at the conversion of CDT reached 72.3 mol%, was obtained at the temperature of 50 degrees C, for the catalyst content of 0.45 mol% (in relation to the introduced CDT), for the molar ratio of H2O2:CDT 1.5:1, with toluene as the solvent and after the reaction time of 30 min. Considering the he obtained results and numerous applications of ECDD, further research should be developed to provide a more efficient and environmentally friendly way of obtaining this compound. [GRAPHICS] .

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