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2010 | 12 | 3 | 40-44
Tytuł artykułu

Epoxidation of 1,5,9-cyclododecatriene with H2O2in the presence of tungstophosphoric acid (H3PW12O40)

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Warianty tytułu
Języki publikacji
EN
Abstrakty
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.
Wydawca

Rocznik
Tom
12
Numer
3
Strony
40-44
Opis fizyczny
Daty
wydano
2010-01-01
online
2010-09-27
Twórcy
  • Institute of Chemical Organic Technology, West Pomeranian University of Technology, ul. Pułaskiego 10, 70-322 Szczecin, Poland
  • Institute of Chemical Organic Technology, West Pomeranian University of Technology, ul. Pułaskiego 10, 70-322 Szczecin, Poland
Bibliografia
  • Lewandowski, G. & Rytwińska, E. (2004). Epoxidation of 1,5,9-cyclododecatriene to 1,2-epoxy-5,9-cyclododecadiene. Przem. Chem., 83 (11), 559-563 (in Polish).
  • Sasson, Y. & Neumann, R. (1997). Handbook of Phase Transfer Catalysis. Blackie Academic & Professional.
  • Witczak, T., Grzesik, M., Witczak, M. & Skrzypek, J. (2007). Heteropolyacids as modern catalysts for esterification reactions, Przem. Chem., 86 (1), 43-47. (in Polish).
  • Kabisch, G. DR., Trube, R., Wittmann, H., Raupach, S. & Malitius, H. (1981). Process for the preparation of 1,2-epoxy- 5,9-cyclododecadiene. EP Patent No. 0033763 (B1).
  • Lecloux, A., Declerck, C. & Legrand, F. (1992). Process for the manufacture of epoxides. US Patent No. 5086189.
  • Venturello, C., Alneri, E. & Lana, G. (1986). Procédé d'époxydation d'oléfines par une réaction d'oxydation catalytique en phase liquide. IT Patent No. 1122214 (B).
  • Venturello, C., Aloisio Rino, D. & Ricci, M. (1984). Peroxide compositions based on tungsten and phosphorus or arsenic, and a process for preparing the same. EP Patent No. 0109273 (A1).
  • Teshigahara, S. & Yoshiaki, K. (1993). Epoxidation of alicyclic olefin. JP Patent No. 5213919 (A).
  • Kuroda, N., Yamanaka, M., Yamazaki, O., Takemoto, H., Ninomiya, K., Kugimoto, J., Kaiso, K. & Shimomura, H. (1999). Process for producing 1,2-Epoxy-5, 9-cyclododecadiene. EP Patent No. 0950659 (A2).
  • Kozhevnikow, I. V. (1995). Heteropolyacids and Related Compounds as Catalysts for Fine Chemical Synthesis. Catal. Rev.- Sci. Eng. 37 (2), 311-352.[Crossref]
  • Ishii, Y., Yamawaki, K. Ura, T., Yamada, H., Yoshida, T. & Ogawa, M. (1988). Hydrogen Peroxide Oxidation Catalyzed by Heteropolyacids Combined with Cetylpiridinium Chloride: Epoxidation of Olefins and Allylic Alcohols, Ketonization of Alcohols and Diols, and Oxidative Cleavage of 1,2-Diols and Olefins. J. Org. Chem. 53, 3587-3593. DOI: 10.1021/jo00250a032.[Crossref]
  • Wypych, G. (Editor) (2010, February) Effect of solvent on chemical reactions and reactivity. Handbook of solvents, ChemTec Publishing, 2001, Retrieved February 1, 2010, from:
Typ dokumentu
Bibliografia
Identyfikatory
Identyfikator YADDA
bwmeta1.element.-psjd-doi-10_2478_v10026-010-0032-z
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