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Application of the design of experiments in the epoxidation process of 1,5,9-cyclododecatriene

100%
Lewandowski G., Ćwirko J.
Polish Journal of Chemical Technology
|
2007
|
vol. 9
|
issue 4
68-71
EN
An influence of the molar ratio of cis, trans, trans-1,5,9-cyclododecatriene to tert-butyl hydroperoxide, the concentration of the catalyst and the reaction time on the performance of the epoxidation process of cis, trans, trans-1,5,9-cyclodecatriene with tert-butyl hydroperoxide at the presence of molybdenum hexacarbonyl Mo(CO)6 was examined. Examinations were performed using statistical methods of the design of experiments. A mathematical model describing the influence of the parameters on conversion cis, trans, trans-1,5,9-cyclododecatriene was obtained. An analysis of the data and rests was performed and an optimal value of conversion of cis, trans, trans-1,5,9-cyclododecatriene was established.
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Epoxidation of 1,5,9-cyclododecatriene with H2O2in the presence of tungstophosphoric acid (H3PW12O40)

88%
Wołosiak A., Lewandowski G.
Polish Journal of Chemical Technology
|
2010
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vol. 12
|
issue 3
40-44
EN
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 (H3PW12O40) 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:H2O2 and H2O2:H3PW12O40, 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:H2O2 = 3:1 - 1.5:1, the molar ratio of H2O2:H3PW12O40 = 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.
3
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Comparison of the methods of the phase transfer catalysis and hydroperoxide in the epoxidation of 1,5,9-cyclododecatriene

88%
Lewandowski G.
Polish Journal of Chemical Technology
|
2007
|
vol. 9
|
issue 3
101-104
EN
The process of the epoxidation of cis, trans, trans-1,5,9-cyclododecatriene (CDT) to 1,2-epoxy-5,9-cyclododecadiene (ECDD) with the 30% aqueous hydrogen peroxide under the phase transfer conditions and with tert-butyl hydroperoxide under the homogeneous conditions was investigated. Onium salts such as Aliquat® 336, Arquad® 2HT, methyltrioctylammonium bromide and the Na2WO4/H3PO4 catalyst system are very active under the phase transfer catalysis (PTC) conditions for the selective epoxidation of cis, trans, trans-1,5,9-cyclododecatiene (PTC method). These catalytic systems were found to be as active and selective as the homogeneous phase system Mo(CO)6/TBHP (hydroperoxide method).
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