Research ArticleOpen AccessGoogle Scholar indexed
Styrene Epoxidation in Aqueous over Triazine-Based Microporous Polymeric Network as a Metal-Free Catalyst
Laboratory of Nano-Green Catalysis and Nano Center for Fine Chemicals Fusion Technology, Department of Chemistry, Inha University, Incheon, Korea
Laboratory of Nano-Green Catalysis and Nano Center for Fine Chemicals Fusion Technology, Department of Chemistry, Inha University, Incheon, Korea
Laboratory of Nano-Green Catalysis and Nano Center for Fine Chemicals Fusion Technology, Department of Chemistry, Inha University, Incheon, Korea
- 1 Laboratory of Nano-Green Catalysis and Nano Center for Fine Chemicals Fusion Technology, Department of Chemistry, Inha University, Incheon, Korea
- 2 Laboratory of Nano-Green Catalysis and Nano Center for Fine Chemicals Fusion Technology, Department of Chemistry, Inha University, Incheon, Korea
- 3 Laboratory of Nano-Green Catalysis and Nano Center for Fine Chemicals Fusion Technology, Department of Chemistry, Inha University, Incheon, Korea
Green and Sustainable Chemistry·Volume 02 (2012)·Pages 1–7·Published 17 February 2012·DOI10.4236/gsc.2012.21001
Copy link · social · email
Abstract
Tirazine based microporous polymeric (TMP) network was found to be an efficient metal-free catalyst for the epoxidation of styrene. The reactions were performed in water as an environmentally benign medium using H2O2 as a green oxidant at ambient temperature. The reaction afforded higher yield with 90% conversion of styrene and 98% selectivity to styrene oxide in 6 h. The triazine based microporous polymeric network can be readily recovered and reused up to 4 cycles without significant loss in catalytic activity and selectivity.
KeywordsTriazine Microporous Polydendritic NetworkMetal-Free CatalystAqueous MediumEpoxidationStyrene
- S. Fioravanti, L. Pellacani, P. A. Tardella and M. C. Ver- gari, “Facile and Highly Stereoselective One-Pot Synthe- sis of Either (E)- or (Z)-Nitro Alkenes,” Organic Letters, Vol. 10, No. 7, 2008, pp. 1449-1451. doi:10.1021/ol800224k
- C. D. Gutsche, R. S. Buriks, K. Nowotny and H. Grassner, “Tertiary Amine Catalysis of the Aldol Condensation,” Journal of the American Chemical Society, Vol. 84, No. 19, 1962, pp. 3775-3777. doi:10.1021/ja00878a040
- I. G. Rios, E. Novarino, S. van der Veer, B. Hessen and M. W. Bouwkamp, “Amine Catalyzed Solvent C-H Bond Activation as Deactivation Route for Cationic Decame- thylzirconocene Olefin Polymerization Catalysts,” Jour- nal of the American Chemical Society, Vol. 131, No. 46, 2009, pp. 16658-16659. doi:10.1021/ja908330v
- I. T. Glover, G. W. Cushing and C. M. Windsor, “Amine- catalyzed Isomerization of Diethylmaleate to Diethylfu- marate,” Journal of Chemical Education, Vol. 55, No. 12, 1978, p. 812. doi:10.1021/ed055p812
- Y. Imada, H. Iida, S. Ono and S.-I. Murahashi, “Flavin Catalyzed Oxidations of Sulfides and Amines with Mo- lecular Oxygen,” Journal of the American Chemical So- ciety, Vol. 125, No. 10, 2003, pp. 2868-2869. doi:10.1021/ja028276p
- V. K. Aggarwal, C. Lopin and F. Sandrinelli, “New Insights in the Mechanism of Amine Cata-lyzed Epoxidation: Dual Role of Protonated Ammonium Salts as Both Phase Transfer Catalysts and Activators of Oxone,” Journal of the American Chemical Society, Vol. 125, No. 25, 2003, pp. 7596-7601. doi:10.1021/ja0289088
- A. C. Blanc, S. Valle, G. Renard, D. Brunel, D. J. Mac- quarrie and C. R. Quinn, “The Preparation and Use of Novel Immobilised Guani-dine Catalysts in Base-Cata- lysed Epoxidation and Condensa-tion Reactions,” Green Chemistry, Vol. 2, No. 6, 2000, pp. 283-288. doi:10.1039/b005929n
- M. Wang, L. X. Gao, W. P. Mai, A. X. Xia, F. Wang and S. B. Zhang, “Enantioselective Iodolac-tonization Catalyzed by Chiral Quaternary Ammonium Salts Derived from Cinchonidine,” The Journal of Organic Chemistry, Vol. 69, No. 8, 2004, pp. 2874-2876. doi:10.1021/jo035719e
- A. G. Wenzel and E. N. Jacobsen, “Asymmetric Catalytic Mannich Reactions Catalyzed by Urea Derivatives: En- antioselective Synthesis of β-Aryl-β-Amino Acids,” Jour- nal of the American Chemical Society, Vol. 124, No. 44, 2002, pp. 12964-12965. doi:10.1021/ja028353g
- A. Cordova, W. Zou, I. Ibrahem, E. Reyes, M. Engqvist and W.-W. Liao, “Acyclic Amino Acid-Catalyzed Direct Asymmetric Aldol Reactions: Alanine, the Simplest Ste- reoselective Organo-catalyst,” Chemical Communications, No. 28, 2005, pp. 3586-3588.