Ultrasound and ionic liquid: An efficient combination to tune the mechanism of alkenes epoxidation

Ultrasonics Sonochemistry

Volumn 19, Issue 3, 2012, Pages 390-394

  Chatel, Gregory ^a,b   Goux Henry, Catherine ^b   Kardos, Nathalie ^a   Suptil, Joel ^a   Andrioletti, Bruno ^b   Draye, Micheline ^a  

^a UNIVERSITÉ DE SAVOIE   (France)

^b UNIVERSITÉ LYON 1   (France)

Author keywords

Alkenes; Epoxidation; Ionic liquids; Mn porphyrin; Ultrasound

Indexed keywords

EPOXIDATION; HYDROCARBONS; IRRADIATION; OLEFINS; OXIDATION; ULTRASONICS;

ALKENES EPOXIDATIONS; MN PORPHYRINS; OLEFIN OXIDATION; OXIDATION PROCESS; OXIDATION SYSTEMS; PROOF OF CONCEPT; ULTRASOUND IRRADIATION;

IONIC LIQUIDS;

ALKENE; IONIC LIQUID; MANGANESE DERIVATIVE; METALLOPORPHYRIN; MOLYBDENUM;

ARTICLE; CATALYSIS; CHEMICAL INTERACTION; EPOXIDATION; HYDROPHILICITY; IRRADIATION; OXIDATION KINETICS; PRIORITY JOURNAL; PROCESS OPTIMIZATION; REACTION TIME; ULTRASOUND;

EID: 84855260828     PISSN: 13504177     EISSN: 18732828     Source Type: Journal    
DOI: 10.1016/j.ultsonch.2011.10.007     Document Type: Article

References (23)

1. (a) H. Yao, D.E. Richardson, Epoxidation of alkenes with bicarbonate-activated hydrogen peroxide, J. Am. Chem. Soc. 122 (2000) 3220-3221;
2. (b) R. Noyori, M. Aoki, K. Sato, Green oxidation with aqueous hydrogen peroxide, Chem. Commun. 16 (2003) 1977-1986. (Pubitemid 36986592)
3. B. Balagam, R. Mitra, D.E. Richardson, Osmium-catalyzed asymmetric dihydroxylation by carbon dioxide-activated hydrogen peroxide and Nmethylmorpholine, Tetrahedron Lett. 49 (2008) 1071-1075.
4. (a) V.N. Kislenko, A.A. Berlin, Kinetics and mechanism of the oxidation of organic compounds with hydrogen peroxide, Russ. Chem. Rev. 60 (1991) 470-488;
5. (b) C.W. Jones, Applications of Hydrogen Peroxide and Derivates, Royal Society of Chemistry, Cambridge, 1999.
6. B.S. Lane, M. Vogt, V.J. DeRose, K. Burgess, Manganese-catalyzed epoxidations of alkenes in bicarbonate solutions, J. Am. Chem. Soc. 124 (2002) 11946-11954.
7. (a) B. Meunier, Metalloporphyrins as versatile catalysts for oxidation reactions and oxidative DNA cleavage, Chem. Rev. 92 (1992) 1411-1456;
8. (b) B.S. Lane, K. Burgess, Metal-catalyzed epoxidations of alkenes with hydrogen peroxide, Chem. Rev. 103 (2003) 2457-2474.
9. E. Rose, B. Andrioletti, S. Zrig, M. Quelquejeu-Ethève, Enantioselective epoxidation of olefins with chiral metalloporphyrin catalysts, Chem. Soc. Rev. 34 (2005) 573-583. (Pubitemid 40992745)
10. H.H. Monfared, V. Aghapoor, M. Ghorbanloo, P. Mayer, Highly selective olefin epoxidation with the bicarbonate activation of hydrogen peroxide in the presence of manganese(III) meso-tetraphenylporphyrin complex: optimization of effective parameters using the Taguchi method, Appl. Catal. A 372 (2010) 209-216.
11. (a) R. Rogers, R. Sheldon, Ionic Liquids as Green Solvents: Progress and Prospects, An American Chemical Society Publication, 2003.;
12. (b) K. Seddon, Catalytic reactions in ionic liquids, Chem. Commun. 23 (2001) 2399-2407.
13. P. Lignier, J. Estager, N. Kardos, L. Gravouil, J. Gazza, E. Naffrechoux, M. Draye, Swift and efficient sono-hydrolysis of nitriles to carboxylic acids under basic condition: role of the oxide anion radical in the hydrolysis mechanism, Ultrason. Sonochem. 18 (2011) 28-31.
14. P. Cintas, J.-L. Luche, Green chemistry: the sonochemical approach, Green Chem. 1 (1999) 115-125.
15. K.-H. Tong, K.-Y. Wong, T.H. Chan, Manganese/bicarbonate-catalyzed epoxidation of lipophilic alkenes with hydrogen peroxide in ionic liquids, Org. Lett. 5 (2003) 3423-3425. (Pubitemid 37487429)
16. D. Betz, A. Raith, M. Cokoja, F.E. Kühn, Olefin epoxidation with a new class of ansa-molybdenum catalysts in ionic liquids, ChemSusChem 3 (2010) 559-562.
17. S. Koda, T. Kimura, T. Sakamoto, T. Kondo, H. Mitome, A standard method to calibrate sonochemical efficiency of an individual reaction system, Ultrason. Sonochem. 10 (2003) 149-156. (Pubitemid 36506684)
18. (a) A.D. Adler, F.R. Longo, J.D. Finarelli, J. Goldmacher, J. Assour, L. Korsakoff, A simplified synthesis for meso-tetraphenylporphyrin, J. Org. Chem. 32 (1967) 476;
19. (b) A.D. Adler, F.R. Longo, F. Kampas, J. Kim, On the preparation of metalloporphyrins, Inorg. Nucl. Chem. 32 (1970) 2443-2445.
20. 2) provide a stable environment in oxidation conditions. See K.-P. Ho, W.-L. Wong, L.Y.S. Lee, K.- M. Lam, T.H. Chan, K.-Y. Wong, Manganese acetate in pyrrolidinium ionic liquid as a robust and efficient catalytic system for epoxidation of aliphatic terminal alkenes, Chem. Asian J. 5 (2010) 1970-1973.
21. N.N. Mahamuni, P. Gogate, A. Pandit, Ultrasound-accelerated green and selective oxidation of sulfides to sulfoxides, Ind. Eng. Chem. Res. 45 (2006) 8829-8836. (Pubitemid 46102168)
22. P. Battioni, J.P. Renaud, J.F. Bartoli, M. Reina-Artiles, M. Fort, D. Mansuy, Monooxygenase-like oxidation of hydrocarbons by hydrogen peroxide 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.
23. J.-P. Renaud, P. Battioni, J.-F. Bartoli, D. Mansuy, A very efficient system for alkene epoxidation by hydrogen peroxide: catalysis by manganese-porphyrins in the presence of imidazole, J. Chem. Soc. Chem. Commun. (1985) 888-889.