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

Wołosiak A., Lewandowski G.

Polish Journal of Chemical Technology

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2010

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Vol. 12, nr 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 AliquatŽ 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.

2

Wybór optymalnego modelu matematycznego procesu na przykładzie konwersji wodoronadtlenku tert-butylu w reakcji epoksydowania 1,5,9-cyklododekatrienu w obecności Mo(CO)6

Lewandowski G., Ćwirko J.

Przemysł Chemiczny

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2009

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T. 88, nr 9

1011-1018

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Comparison of the methods of the phase transfer catalysis and hydroperoxide in the epoxidation of 1,5,9-cyclododecatriene

Lewandowski G.

Polish Journal of Chemical Technology

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2007

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Vol. 9, nr 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 AliquatŽ 336, ArquadŽ 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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Application of the design of experiments in the epoxidation process of 1,5,9-cyclododecatriene

Lewandowski G., Ćwirko J.

Polish Journal of Chemical Technology

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2007

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Vol. 9, nr 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.