Efficiency of selected phase transfer catalysts for the synthesis of 1,2-epoxy-5,9-cyclododecadiene in the presence of H2O2/H3PW12O40 as catalytic system

• Autorzy: Lewandowski G.
• Języki publikacji: EN

Abstrakty

EN

The results of the studies on the influence of the phase transfer catalyst on the epoxidation of (Z,E,E)-1,5,9-cyclododecatriene (CDT) to 1,2-epoxy-5,9-cyclododecadiene (ECDD) in the H2O2/H3PW12O40 system by a method of phase transfer catalysis (PTC) were presented. The following quaternary ammonium salts were used as phase transfer catalysts: methyltributylammonium chloride, (cetyl)pyridinium bromide, methyltrioctylammonium chloride, (cetyl)pyridinium chloride, dimethyl[dioctadecyl(76%)+dihexadecyl(24%)] ammonium chloride, tetrabutylammonium hydrogensulfate, didodecyldimethylammonium bromide and methyltrioctylammonium bromide. Their catalytic activity was evaluated on the basis of the degree of CDT and hydrogen peroxide conversion and the selectivities of transformation to ECDD in relation to consumed CDT and hydrogen peroxide. The most effective PT catalysts were selected based on the obtained results. Among the onium salts under study, the epoxidation of CDT with hydrogen peroxide proceeds the most effectively in the presence of methyltrioctylammonium chloride (Aliquat® 336) and (cetyl)pyridinium chloride (CPC). The relatively good results of CDT epoxidation were also achieved in the presence of Arquad® 2HT and (cetyl)pyridinium bromide.

Słowa kluczowe

EN

epoxidation; (Z,E,E)-1,5,9-cyclododecatriene; 1,2-epoxy-5,9-cyclododecadiene; H2O2/H3PW12O40 catalytic system; phase transfer catalysis

• Wydawca: West Pomeranian University of Technology. Publishing House
• Czasopismo: Polish Journal of Chemical Technology
• Rocznik: 2013
• Tom: Vol. 15, nr 3
• Strony: 96--99
• Opis fizyczny: Bibliogr. 11 poz., wykr., wz.

Twórcy

autor

Lewandowski G.

• West Pomeranian University of Technology, Szczecin, Institute of Chemical Organic Technology, ul. Pułaskiego 10, 70-322 Szczecin, Poland

Bibliografia

• 1. Sato, K., Aoki, M., Ogawa, M., Hashimoto, T., Panyella, D. & Noyori, R. (1997). A halide-free method for olefin epoxidation with 30 % hydrogen peroxide. Bull. Chem. Soc. Jpn. 70, 905-915. Retrieved March 15, 2013, from http://www.csj.jp/journals/bcsj/J-STAGE/7004/pdf/70_905.pdf. DOI: 10.1246/ bcsj.70.905.
• 2. Venturello, C. & D’Aloisio, R. (1988). Quaternary ammonium tetrakis(diperoxotungsto)phosphates(3-) as a new class of catalysts for efficient alkene epoxidation with hydrogen peroxide. J. Org. Chem. 53, 1553-1557. Retrieved March 15, 2013, from http://pubs.acs.org. DOI: 10.1021/jo00242a041.
• 3. Venturello, C., D’Aloisio, R., Bart, J.C.J. & Ricci, M. (1985). A new peroxotungsten heteropoly anion with special oxidizing properties: synthesis and structure of tetrahexylammonium tetra (diperoxotungsto) phosphate (3-). J. Mol. Catal., 32, 107-110.
• 4. Ishii, Y., Yamawaki, K., Ura, T., Yamada, H., Yoshida, T. & Ogawa, M. (1988). Hydrogen peroxide oxidation catalyzed by heteropoly acids combined with cetylpyridinium 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. Retrieved March 15, 2013, from http://pubs.acs.org. DOI: 10.1021/jo00250a032.
• 5. Sakaguchi, S., Nishiyama, Y. & Ishii, Y. (1996). Selective oxidation of monoterpenes with hydrogen peroxide catalyzed by peroxotungstophosphate (PCWP). J. Org. Chem. 61, 5307-5311. Retrieved March 15, 2013, from http://pubs.acs.org. DOI: 10.1021/jo960275q.
• 6. Młochowski, J. (1994). Chemistry of heterocyclic compounds, Warszawa, Wydawnictwo Naukowe PWN (in Polish).
• 7. Zhao, W., Ding, Y., Zhang, Zh., Ma, B., Qiu, W. (2011). [(C18H37)2(CH3)2N]7[PW11O39]: a temperaturecontrolled phase transfer catalyst for olefin epoxidation. Reac. Kinet. Mech. Cat. 102, 93-102. DOI: 10.1007/s11144-010-0242-7.
• 8. Mahha, Y., Salles, L., Piquemal, J.M., Briot, E., Atlamsani, A., Brégeault, J.M. (2007). Environmentally friendly epoxidation of olefins under phase-transfer catalysis conditions with hydrogen peroxide. J. Catal., 249, 338-348. DOI: 10.1016/j. jcat.2007.05.001.
• 9. Lewandowski, G. (2001). Cyclotrimerization of 1,3-butadiene to 1,5,9-cyclododecatriene. Synthesis of cyclododecane and cyclooctadiene. Przem. Chem., 80 (11), 507-513 (in Polish).
• 10. Lewandowski, G. & Rytwińska, E. (2006). Reactions and applications of trans-1,2-epoxy-(Z,E)-cyclododeca-5,9-diene. Chem. Pap. 60 (2), 160-168. DOI: 10.2478/s11696-006-0029-5.
• 11. Gruszkowska, E. & Lewandowski, G. (2004). Epoxidation of 1,5,9-cyclododecatriene (CDT) to 1,2-epoxy-5,9-cyclododecadiene (ECDD). Przem. Chem. 83 (11), 559-563 (in Polish).