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

Open access

Abstract

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

If the inline PDF is not rendering correctly, you can download the PDF file here.

  • 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 12-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 13-butadiene to 159-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-12-epoxy-(ZE)-cyclododeca-59-diene. Chem. Pap. 60 (2) 160-168. DOI: 10.2478/s11696-006-0029-5.

  • 11. Gruszkowska E. & Lewandowski G. (2004). Epoxidation of 159-cyclododecatriene (CDT) to 12-epoxy-59-cyclododecadiene (ECDD). Przem. Chem. 83 (11) 559-563 (in Polish).

Search
Journal information
Impact Factor

IMPACT FACTOR 2018: 0.975
5-year IMPACT FACTOR: 0.878

CiteScore 2018: 1

SCImago Journal Rank (SJR) 2018: 0.269
Source Normalized Impact per Paper (SNIP) 2018: 0.46

Cited By
Metrics
All Time Past Year Past 30 Days
Abstract Views 0 0 0
Full Text Views 326 119 4
PDF Downloads 277 193 21