Epoxidation of 1,5,9-cyclododecatriene with H₂O₂ in the presence of tungstophosphoric acid (H₃PW₁₂O₄₀)

Abstract

The influence of the technological parameters on the epoxidation of 1,5,9-cyclododecatriene (CDT) to 1,2-epoxy-5,9-cyclododecadiene (ECDD) by the phase-transfer catalysis method (PTC) in the presence of tungstophosphoric heteropolyacid (H 3 PW 12 O 40 ) and hydrogen peroxide as the oxidizing agent has been presented. The phase-transfer catalyst was Aliquat ® 336 (methyltrioctylammonium chloride). The epoxidation of CDT to ECDD in the PTC system proceed under the relatively mild condition: low temperature, lack of solvent, short reaction time. The effect of: the mixing velocity, the molar ratio of CDT:H 2 O 2 and H 2 O 2 :H 3 PW 12 O 40 , the nature of the solvent and its concentration, was studied. The most advantageous technological parameters were: the mixing rate 400 -600 rpm, the molar ratio of CDT:H 2 O 2 = 3:1 -1.5:1, the molar ratio of H 2 O 2 :H 3 PW 12 O 40 = 200:1 -400:1, the temperature 40 -50°C, solvent: dichloromethane or lack of the solvent, dichloromethane concentration: 10 -50 vol%, reaction time 35 -50 min. The application of the above-mentioned parameters allows to achieve the yield of 44 -47% ECDD in relation to introduced CDT.

Epoxidation of 1,5,9-Cyclododecatriene with Hydrogen Peroxide over Ti-MCM-41 Catalyst

“…The PTC oxidation catalyst consists of two parts: the first is responsible for interphase transport (most often it is the onium salt), and the second is responsible for oxidation (often these are compounds formed as a result of the reaction of tungsten acid or its salt with hydrogen peroxide). There is already a large amount of information available in the literature on the obtainment of ECDD under these conditions [9,[18][19][20].…”