Fine-Tuning and Recycling of Homogeneous Tungstate and Polytungstate Epoxidation Catalysts

Mechanisms in Homogeneous and Heterogeneous Epoxidation Catalysis

Volumn , Issue , 2008, Pages 415-428

  Alsters, Paul L ^a   Witte, Peter T ^a   Neumann, Ronny ^b   Sloboda Rozner, Dorit ^b   Adam, Waldemar ^c,d   Zhang, Rui ^c   Reedijk, Jan ^e   Gamez, Patrick ^e   ten Elshof, Johan E ^f   Roy Chowdhury, Sankhanilay ^f  

^a Catalysis and Development   (Netherlands)

^b WEIZMANN INSTITUTE OF SCIENCE   (Israel)

^c UNIVERSITY OF WÜRZBURG   (Germany)

^d UNIVERSITY OF PUERTO RICO   (Puerto Rico)

^e LEIDEN UNIVERSITY   (Netherlands)

^f UNIVERSITY OF TWENTE   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84887539682     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1016/B978-0-444-53188-9.00016-X     Document Type: Chapter

References (28)

1. 12- (X = M = zinc or cobalt) and their M-substituted derivatives. Syntheses, chemical, structural and spectroscopic study of some D,L sodium and potassium salts. J. Chem. Soc. Dalton Trans 1991, 143.
2. Mizuno N., Misono M. Heterogeneous catalysis. Chem. Rev 1998, 98:199.
3. Hill C.L., Prosser-McCartha C.M. Homogeneous catalysis by transition metal oxygen anion clusters. Coord. Chem. Rev 1995, 143:407.
4. Kozhevinikov I.V. Catalysis by heteropoly acids and multicomponent polyoxometalates in liquid-phase reactions. Chem. Rev 1998, 98:171.
5. Neumann R. Polyoxometalate complexes in organic oxidation chemistry. Prog. Inorg. Chem 1998, 47:317.
6. Sloboda-Rozner D., Alsters P.L., Neumann R. A water-soluble and "self-assembled" polyoxometalate as a recyclable catalyst for oxidation of alcohols in water with hydrogen peroxide. J. Am. Chem. Soc 2003, 125:5280.
7. 12-, as a remarkably effective catalyst for hydrogen peroxide mediated oxidations. J. Am. Chem. Soc 1995, 117:5066.
8. Adam W., Alsters P.L., Neumann R., Saha-Möller C.R., Seebach D., Beck A.K., Zhang R. Chiral hydroperoxides as oxygen source in the catalytic stereoselective epoxidation of allylic alcohols by sandwich-type polyoxometalates: Control of enantioselectivity through a metal-coordinated template. J. Org. Chem 2003, 68:8222.
9. Sloboda-Rozner D., Witte P., Alsters P.L., Neumann R. Aqueous biphasic oxidation: A water-soluble polyoxometalate catalyst for selective oxidation of various functional groups with hydrogen peroxide. Adv. Synth. Cat 2004, 346:339.
10. 2] as an industrially attractive multi-purpose catalyst for oxidations with aqueous hydrogen peroxide. Org. Process Res. Dev 2004, 8:524.
11. Ishii Y., Yamawaki K., Ura T., Yamada H., Yoshida T., Ogawa M. 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 1988, 53:3587.
12. Venturello C., D'Aloisio R. Quaternary ammonium tetrakis(diperoxotungsto)phosphates(3-) as a new class of catalysts for efficient alkene epoxidation with hydrogen peroxide. J. Org. Chem 1988, 53:1553.
13. 3NMe]Cl was used as phase-transfer catalyst. Tetrahedron Lett 1986, 27:2617.
14. Satu K., Aoki M., Ogawa M., Hashimoto T., Noyori R. A practical method for epoxidation of terminal olefins with 30% hydrogen peroxide under halide-free conditions. J. Org. Chem 1996, 61:8310.
15. 4-based highly efficient biphasic catalyst towards alkene epoxidation, using dihydrogen peroxide as oxidant. J. Reedijk Adv. Synth. Cat 2005, 347:1759.
16. 2 as oxidant. J. Reedijk J. Mol. Cat. A 2006, 258:295.
17. Adam W., Alsters P.L., Neumann R., Saha-Möller C.R., Seebach D., Zhang R. Highly efficient catalytic asymmetric epoxidation of allylic alcohols by an oxovanadium-substituted polyoxometalate with a regenerative TADDOL-Derived hydroperoxide. Org. Lett 2003, 5:725.
18. Villa A.L., De Vos D.E., Verpoort F., Sels B.F., Jacobs P.A. A study of V-pillared layered double hydroxides as catalysts for the epoxidation of terpenic unsaturated alcohols. J. Catal 2001, 198:223.
19. Haanepen M.J., Van Hooff J.H.C. VAPO as catalyst for liquid phase oxidation reactions. Part I: preparation, characterization and catalytic performance. Appl. Catal. A 1997, 152:183.
20. Haanepen M.J., Elemans-Mehring A.M., Van Hooff J.H.C. VAPO as catalyst for liquid phase oxidation reactions. Part II: stability of VAPO-5 during catalytic operation. Appl. Catal. A 1997, 152:203.
21. Sharpless K.B., Michaelson R.C. High stereo- and regioselectivities in the transition metal catalyzed epoxidations of olefinic alcohols by tert-butyl hydroperoxide. J. Am. Chem. Soc 1973, 95:6136.
22. Michaelson R.C., Palermo R.E., Sharpless K.B. Chiral hydroxamic acids as ligands in the vanadium catalyzed asymmetric epoxidation of allylic alcohols by tert-butyl hydroperoxide. J. Am. Chem. Soc 1977, 99:1990.
23. Adam W., Alsters P.L., Neumann R., Saha-Möller C.R., Sloboda-Rozner D., Zhang R. A highly chemoselective, diastereoselective, and regioselective epoxidation of chiral allylic alcohols with hydrogen peroxide, catalyzed by sandwich-type polyoxometalates: Enhancement of reactivity and control of selectivity by the hydroxy group through metal-alcoholate bonding. J. Org. Chem 2003, 68:1721.
24. Adam W., Alsters P.L., Neumann R., Saha-Möller C.R., Sloboda-Rozner D., Zhang R. A new highly selective method for the catalytic epoxidation of chiral allylic alcohols by sandwich-type polyoxometalates with hydrogen peroxide. Synlett 2002, 2001.
25. See: . http://www.basf.com/businesses/consumer/cosmeticingredients/html/mquater nary.html.
26. Dijkstra H.P., van Klink G.P.M., van Koten G. The use of ultra- and nanofiltration techniques in homogeneous catalyst recycling. Acc. Chem. Res 2002, 35:798.
27. Witte P.T., Roy Chowdhury S., ten Elshof J.E., Sloboda-Rozner D., Neumann R., Alsters P.L. Highly efficient recycling of a "sandwich" type polyoxometalate oxidation catalyst using solvent resistant nanofiltration. Chem. Commun 2005, 1206.
28. Roy Chowdhury S., Witte P.T., Blank D.H.A., Alsters P.L., ten Elshof J.E. Recovery of homogeneous polyoxometalate catalysts from aqueous and organic media by a mesoporous ceramic membrane without loss of catalytic activity. Chem. Eur. J 2006, 12:3061.