Epoxidation of dicyclopentadiene under phase transfer catalysis conditions: Pseudo steady state hypothesis approach

Journal of Chemical Engineering of Japan

Volumn 36, Issue 3, 2003, Pages 231-242

  Wang, Maw Ling ^a   Huang, Tsuan Hsuan ^b  

^a TUNGHAI UNIVERSITY   (Taiwan)

^b NATIONAL TSING HUA UNIVERSITY   (Taiwan)

Author keywords

Cocatalyst; Dicyclopentadiene; Epoxidation; Hydrogen peroxide; Phase transfer catalysis

Indexed keywords

CATALYSIS; HYDROGEN PEROXIDE; ORGANIC SOLVENTS; OXIDATION; PHASE TRANSITIONS; SALTS;

EPOXIDATION;

AROMATIC HYDROCARBONS;

PHASE CHANGE;

EID: 0042567548     PISSN: 00219592     EISSN: None     Source Type: Journal    
DOI: 10.1252/jcej.36.231     Document Type: Article

References (21)

1. Angellitti, E., P. Tundo, P. Venturello and F. Trotta; "Synthetic Opportunities of Gas-Liquid Phase-Transfer Catalysis," British Polymer J., 16, 219-221 (1984)
2. Aubry, C., G. Chottard, N. Platzer, J.-M. Bregeault, R. Thouuvenot, F. Chauveau, C. Huet and H. Ledon; "Reinvestigation of Epoxidation Using Tungstate-Based Precursors and Hydrogen Peroxide in a Biphase Medium," Inorg. Chem., 30, 4409-4415 (1991)
3. Bartolina, O., M. Momenteau and B. Meunier; "Definitive Evidence for Proximal Effect of Pyridine in the NaOCl/Mn(porphyrin)X/ Pyridine Catalytic Oxygenation System," Tetrahedron Lett., 25, 5733-5776 (1984)
4. Collmann, J. P., J. L. Brauman, B. Meunier, T. Hayashi, T. Kodadek and S. A. Raybuck; "Epoxidation of Olefins by Cytochrome P-450 Model Compound: Kinetics and Stereochemistry of Oxygen Atom Transfer and Origin of Shape Selectivity," J. Am. Chem. Soc., 107, 2000-2005 (1985)
5. Dehmlow, E. V. and S. S. Dehmlow; Phase Transfer Catalysis, Verlag Chemie, Weinheim, Germany (1983)
6. Freedman, H. H.; "Industrial Applications of Phase Transfer Catalysis (PTC): Past, Present and Future," Pure Appl. Chem., 58, 857-868 (1986)
7. 2," Tetrahedron Lett., 23, 2767-2768 (1982)
8. Ishii, Y., K. Yamawaki, T. Ura, H. Yamada, T. Yoshida and M. Ogawa; "Oxidation of Olefins and Alcohols by Peroxo-molybdenum Complex Derived from Tris(cetylpyridinium) 12- Molybdophosphate and Hydrogen Peroxide," J. Org Chem., 52, 1868-1870 (1987)
9. Ishii, Y., K. Yamawaki, T. Ura, H. Yamada, T. Yoshida and M Ogawa; "Hydrogen Peroxide Oxidation Catalyzed by Heteropolyacids 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 (1988)
10. Jarrouse, J.; "The Influence of Quaternary Chemicals on the Reaction of Labile Hydrogen Compounds and Chlorine-Substituted Derivatives," C. R. Hebd. Seances Acad. Sci., Ser., C232, 1424-1434 (1951)
11. -) and Nitrobenzenesulfonyl Chlorides," J. Org. Chem., 48, 1562-1564 (1983)
12. Kluge, R., M. Schulz and S. Liebsch; "Diastereoselective Epoxidation of Olefins by Organosulfonic Peracids, II," Tetrahedron, 52, 2957-2976 (1996)
13. Menger, F. M.; "Reactivity of Organic Molecules at Phase Boundaries," Chem. Soc. Rev., 1, 229-240 (1972)
14. Montanari, F., M. Penso, S. Quici and P. Vigano; "Highly Efficient NaOCI Olefin Epoxidations Catalyzed by Imidazole or Pyridine Tailed Manganese Porphyrins under Two-Phase Conditions. Influence of pH and of the Anchored Axial Ligand," J. Am. Chem. Soc., 50, 4888-4893 (1985)
15. Quici, S. and R. L. Regen; "Evidence for Solid-Liquid Phase-Transfer Catalysis," J. Org. Chem., 45, 1700-1701 (1980)
16. Regen, S. L.; "Triphase Catalysis," Angew. Chem., Int. Ed. in English, 18, 421-429 (1979)
17. 2' System. Synthesis and X-ray Structure of Tetrabutylammonium (α-Hydrogen phosphato)bis(μ -peroxo)bis(oxoperoxotungstate)(2-): A Catalyst of Olefin Epoxidation in a Biphase Medium," Inorg. Chem., 33, 871-878 (1994)
18. Starks, C. M., C. L. Liotta and M. E. Halpern; Phase-Transfer Catalysis, Fundamentals, Applications and Industrial Perspectives, Chapman & Hall Book Co., New York, USA (1994)
19. Venturello, C. and R. D' Aloisio; "Quaternary Ammonium Tetrakis(diperoxotungsto)phosphate(3-) as a New Class of Catalysts for Efficient Alkene Epoxidation with Hydrogen Peroxide," J. Org. Chem., 53, 1553-1557 (1988)
20. Weber, W. P. and G. W. Gokel; Phase Transfer Catalysis in Organic Chemistry, Springer Verlag, New York, USA (1977)
21. Yoon, H. and C. J. Burrows; "Catalysis of Alkene by Nickel Salen Complexes Using NaOCl Under Phase-Transfer Conditions," J. Am. Chem. Soc., 110, 4087-4089 (1988)