Micellar catalysis for selective epoxidations of linear alkenes

Chemical Engineering and Processing

Volumn 42, Issue 3, 2003, Pages 223-230

  Heijnen, J H M ^a   De Bruijn, V G ^a   Van den Broeke, L J P ^a   Keurentjes, J T F ^a  

^a EINDHOVEN UNIVERSITY OF TECHNOLOGY   (Netherlands)

Author keywords

Epoxidation; Hydrogen peroxide; Micellar catalysis; Micelle; Olefin; Porphyrin catalyst; Surfactant

Indexed keywords

CATALYSIS; HYDROGEN PEROXIDE; OLEFINS; PORPHYRINS; TUNING; ULTRAFILTRATION;

SELECTIVE EPOXIDATION;

CHEMICAL ENGINEERING;

CATALYST;

EID: 0037332340     PISSN: 02552701     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0255-2701(02)00091-0     Document Type: Article

References (25)

1. Dautzenberg F.M., Mukherjee M. Process intensification using multifunctional reactors. Chem. Eng. Sci. 56:2001;251-267.
2. Goetheer E.L.V., Vorstman M.A.G., Keurentjes J.T.F. Opportunities for process intensification using reverse micelles in liquid and supercritical carbon dioxide. Chem. Eng. Sci. 54:1999;1589-1596.
3. Fendler J.H. Membrane Mimetic Chemistry. 1982;Wiley, New York.
4. Menger F.M., Portnoy C.E. On the chemistry proceeding inside molecular aggregates. J. Am. Chem. Soc. 89:1967;4698-4703.
5. Rabion A., Buchanan R.M., Seris J., Fish R. Biomimetic oxidation studies. 10. Cyclohexane oxidation reactions with active site methane monooxygenase enzyme models and t-butyl hydroperoxide in aqueous micelles: mechanistic insights and the role of t-butoxy radicals in the C-H functionalization reaction. J. Mol. Cat. A: Chem. 116:1997;43-47.
6. Karakanov E.A., Flippova T.Y., Martynova S.A., Maximov A.L., Predeina V.V., Topchieva I.N. New catalytic systems for selective oxidation of aromatic compounds by hydrogen peroxide. Catalysis Today. 44:1998;189-198.
7. Broxton T.J., Nasser A. Micellar catalysis of organic reactions. Part 37. A comparison of the catalysis of ester and amide hydrolysis by copper-containing micelles. Can. J. Chem. 75:1997;202-206.
8. Monti D., Tagliatesta P., Mancini G., Boschi T. Micelle-bound metalloporphyrins as highly selective catalysts for the epoxidation of alkenes. Angew. Chem. Int. Ed. 37:1998;1131-1133.
9. Scamehorn J.F., Harwell J.H., Surfactant-Based Separation Processes. Surfactant Science Series. 33:1989;Marcel Dekker, New York.
10. 2 catalyzed by manganese porphyrins and imidazole: selection of the best catalytic system and nature of the active oxygen species. J. Am. Chem. Soc. 110:1988;8462-8470.
11. 2 or NaOCl alkene epoxidation. J. Chem. Soc. Perkin Trans. 1:1993;1345-1357.
12. Banfi S., Cavalieri C., Cavazzini M., Trebicka A. Mn-tetraarylporphyrins bearing N-alkyl sulphonamido tails: effect of the length and polarity of the chains on physical properties and reactivity. J. Mol. Cat. A: Chem. 151:2000;17-28.
13. Iwanejko R., Mlodnicka T., Poltowicz J. Metalloporphyrin-catalyzed oxidation of some hydrocarbons with hydrogen peroxide. Bull. Pol. Acad. Sci. Chem. 43:1995;325-336.
14. Anelli P.L., Banfi S., Montanari F., Quici S. Synergistic effect of lipophilic carboxylic acids and heterocyclic axial ligands in alkene epoxidation by hydrogen peroxide catalysed by manganese(III) tetraarylporphyrins. J. Chem. Soc., Chem. Commun. 1989;779-780.
15. Thellend A., Battioni P., Mansuy D. Ammanium acetate as a very simple and efficient cocatalyst for manganese porphyrin-catalyzed oxygenation of hydrocarbons by hydrogen peroxide. J. Chem. Soc., Chem. Commun. 1994;1035-1036.
16. -, where P=the dianion of 5-(4-N-hexadecylpyridiniumyl)-10,15,20-triphenylporphyrin bromide and M=VO, Ni, or Cu. Inorg. Chem. 30:1991;1898-1905.
17. Gandidni S.C.M., Yushmanov V.E., Borissevitch I.E., Tabak M. Interaction of the tetra(4-sulfonatophenyl)porphyrin with ionic surfactants: aggregation and location in micelles. Langmuir. 15:1999;6233-6243.
18. Rossi S., Ristori S., Pozzi G., Martini G. Spectroscopic characterization of fluorinated/hydrogenated mixed vesicles containing fluorinated Mn(III)-porphyrin. Inorg. Chim. Act. 272:1998;274-282.
19. van Esch J.H., Feiters M.C., Peters A.M., Nolte R.J.M. UV-Vis, fluorescence and EPR studies of porphyrins in bilayers of dioctadecyldimethylammonium surfactants. J. Phys. Chem. 98:1994;5541-5551.
20. G. Legemaat, Epopxidation of alkenes by hydrogen peroxide, catalysed by metal porphyrin complexes, Ph.D. thesis Utrecht University, Utrecht, Netherlands, 1990.
21. 2+) in aqueous micellar media. Inorg. Chem. 28:1989;2725-2731.
22. Maiti N.C., Mazumdar S., Periasamy N. Dynamics of phorphyrin molecules in micelles. Picosecond time-resolved fluorescence anisotropy studies. J. Phys. Chem. 99:1995;10708-10715.
23. Schenning A.P.H.J., Hubert D.H.W., Feiters M.C., Nolte R.J.M. Control of aggregation and tuning of the location of porphyrins in synthetic membranes as mimics for cytochrome P450. Langmuir. 12:1996;1572-1577.
24. Mehra A. An overview of microphase catalysis. Curr. Sci. 59:1990;970-979.
25. Kirk-Othmer Encyclopedia of Chemical Technology, 4th edition, Wiley, New York, Vol. 20, 1991, pp. 271-302.