La complex@Fe-PILM offering resilient option for efficient and green processing toward epoxidation of cyclohexene

Industrial and Engineering Chemistry Research

Volumn 50, Issue 15, 2011, Pages 8973-8982

  Varadwaj, Guru Bishwa Bidita ^a   Sahu, Swagatika ^a   Parida, Kulamani ^a  

^a CSIR INSTITUTE OF MINERALS AND MATERIALS TECHNOLOGY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

ANALYTICAL CHARACTERIZATION; CATALYTIC APPLICATIONS; CATION-EXCHANGE MECHANISM; CYCLOHEXENE EPOXIDATION; CYCLOHEXENES; FTIR ANALYSIS; GREEN PROCESSING; HETEROGENEOUS CATALYST; PILLARED CLAY; PILLARED MONTMORILLONITE; POROUS STRUCTURES; SALEN COMPLEX; STRUCTURAL FEATURE; TERT-BUTYLHYDROPEROXIDE; XRD;

CALCINATION; CATALYSTS; CLAY MINERALS; EPOXIDATION; IRON; LANTHANUM; LANTHANUM ALLOYS; OLEFINS; REUSABILITY; SYNTHESIS (CHEMICAL);

IRON COMPOUNDS;

EID: 79960856223     PISSN: 08885885     EISSN: 15205045     Source Type: Journal    
DOI: 10.1021/ie2002445     Document Type: Article

References (42)

1. Lane, B. S.; Burgess, K. Metal-Catalyzed Epoxidations of Alkenes with Hydrogen Peroxide Chem. Rev. 2003, 103, 2457
2. Jacobsen, E. N.; Zhang, W.; Muci, A. R.; Ecker, J. R.; Deng, L. Highly enantioselective epoxidation catalysts derived from 1,2-diaminocyclohexane J. Am. Chem. Soc. 1991, 113, 7063
3. DeSimone, J. M. Practical Approaches to Green Solvents Science 2002, 297, 799
4. Jeon, S.-J.; Li, H.; Walsh, P. J. A Green Chemistry Approach to a More Efficient Asymmetric Catalyst: Solvent-Free and Highly Concentrated Alkyl Additions to Ketones J. Am. Chem. Soc. 2005, 127, 16416
5. Ovitt, T. M.; Coates, G. W. Stereoselective Ring-Opening Polymerization of meso-Lactide: Synthesis of Syndiotactic Poly(lactic acid) J. Am. Chem. Soc. 1999, 121, 4072
6. Mascarenhas, C. M.; Miller, S. P.; White, P. S.; Morken, J. P. First Catalytic Asymmetric Aldol-Tishchenko Reaction-Insight into the Catalyst Structure and Reaction Mechanism Angew. Chem., Int. Ed. 2001, 40, 601
7. O'Shaughnessy, P. N.; Knight, P. D.; Morton, C.; Gillespie, K. M.; Scott, P. Chiral-at-metal organolanthanides: enantioselective aminoalkene hydroamination/cyclisation with non-cyclopentadienyls Chem. Commun. 2003, 1770
8. 3 J. Org. Chem. 2007, 72, 8648
9. Salavati-Niasari, M.; Zamani, E.; Bazarganipour, M. Epoxidation of cyclohexene with K10-montmorillonite and Schiff-base macrocyclic copper complexes Appl. Clay Sci. 2007, 38, 9
10. Akelah, A.; Rehab, A.; Kenawy, E.-R.; Abou Zeid, M. S. Catalytic Activity of Polymer-Montmorillonite Composites in Chemical Reactions J. Appl. Polym. Sci. 2006, 101, 1121
11. Baj, S.; Siewniak, A.; Socha, B. Synthesis of dialkyl peroxides in the presence of polymer-supported phase-transfer catalysts Appl. Catal., A: Gen. 2006, 309, 85
12. Yoo, D.-W; Han, J.-H.; Nam, S. H.; Kim, H. J.; Kim, C.; Lee, J.-K. Efficient transesterification by polymer-supported zinc complexes: Clean and recyclable catalysts Inorg. Chem. Commun. 2006, 9, 654
13. Zimowska, M.; Michalik-Zym, A.; Poltowicz, J.; Bazarnik, M.; Bahranowski, K.; Serwicka, E. M. Catalytic oxidation of cyclohexene over metalloporphyrin supported on mesoporous molecular sieves of FSM-16 type-Steric effects induced by nanospace constraints Catal. Today 2007, 124, 55
14. Serwicka, E. M.; Poltowicz, J.; Bahranowski, K.; Olejniczak, Z.; Jones, W. Cyclohexene oxidation by Fe-, Co-, and Mn-metalloporphyrins supported on aluminated mesoporous silica Appl. Catal., A: Gen. 2004, 275, 9
15. Medina, J. C.; Gabriunas, N.; Paez-Mozo, E. Cyclohexene oxidation with an iron cyclam-type complex encapsulated in Y-zeolite J. Mol. Catal. A: Chem. 1997, 115, 233
16. Bedioui, F. Zeolite-encapsulated and clay-intercalated metal porphyrin, phthalocyanine and Schiff-base complexes as models for biomimetic oxidation catalysts: an overview Coord. Chem. Rev. 1995, 144, 39
17. Cooke, P. R.; Lindsay Smith, J. R. Alkene epoxidation catalysed by iron(III) and manganese(III) tetraarylporphyrins coordinatively bound to polymer and silica supports J. Chem. Soc., Perkin Trans. 1 1994, 1913
18. Lei, Z. Selective oxidation of cyclohexene catalyzed by polymer-bound ruthenium-2,2′-bipyridine complexes React. Funct. Polym. 2000, 43, 139
19. Campestrini, S.; Meunier, B. Olefin epoxidation and alkane hydroxylation catalyzed by robust sulfonated manganese and iron porphyrins supported on cationic ion-exchange resins Inorg. Chem. 1992, 31, 1999
20. Vaccari, A. Preparation and catalytic properties of cationic and anionic clays Catal. Today 1998, 41, 53
21. Letaief, S.; Casal, B.; Aranda, P.; Martin-Luengo, M. A.; Ruiz-Hitzky, E. Fe-containing pillared clays as catalysts for phenol hydroxylation Appl. Clay Sci. 2003, 22, 263
22. Caudo, S.; Centi, G.; Genovese, C.; Perathoner, S. Copper- and iron-pillared clay catalysts for the WHPCO of model and real wastewater streams from olive oil milling production Appl. Catal. B: Environ. 2007, 70, 437
23. Kurian, M.; Sugunan, S. Catalytic activity of iron pillared montmorillonites for benzylation of benzene with benzyl chloride Bull. Catal. Soc. India 2005, 4, 88
24. Bineesh, K. V.; Kim, S. Y.; Jermy, B. R.; Park, D. W. Synthesis, characterization and catalytic performance of vanadia-doped delaminated zirconia-pillared montmorillonite clay for the selective catalytic oxidation of hydrogen sulphide J. Mol. Catal. A: Chem. 2009, 308, 150
25. Protesescu, L.; Tudorache, M.; Neatu, S.; Grecu, M. N.; Kemnitz, E.; Filip, P.; Parvulescu, V. I.; Coman, S. M. Unusual Behavior of a Novel Heterogeneous Chiral Dimer Cr(III)-Salen Complex in the Epoxidation/Epoxide Ring-Opening Reaction of trans-Methylcinnamate Ester J. Phys. Chem. C 2011, 115, 1112
26. Brunauer, S.; Deming, L. S.; Deming, S. W.; Teller, E. On a theory of the van der Waals adsorption of gases J. Am. Chem. Soc. 1940, 62, 1723
27. Cardoso, B.; Pires, J.; Carvalho, A. P.; Kuzniarska-Biernacka, I.; Silva, A. R.; de Castro, B.; Freire, C. Mn(III) salen complex immobilised into pillared clays by in situ and simultaneous pillaring/encapsulation procedures. Application in the heterogeneous epoxidation of styrene Microporous Mesoporous Mater. 2005, 86, 295
28. Coudurier, G.; Lefebvre, F. Catalyst Characterisation: Physical Techniques for Solid Materials; Plenum Press: New York, 1994.
29. Flego, C.; Galasso, L.; Millini, R.; Kiricsi, I. The influence of the composition on the thermal and acid characteristics of multi-component oxide pillared montmorillonite Appl. Catal., A: Gen. 1998, 168, 323
30. Salerno, P.; Asenjo, M. B.; Mendiroz, S. Influence of preparation method on thermal stability and acidity of Al-PILCs Thermochim. Acta 2001, 379, 101
31. Kurian, M.; Sugunan, S. Liquid phase benzylation of o-xylene over pillared clays Indian J. Chem., Sect. A: Inorg., Bio-inorg., Phys., Theor. Anal. Chem. 2003, 42, 2480
32. Jacobsen, E. N.; Zhang, W.; Muci, A. R.; Ecker, J. R.; Deng, L. Highly enantioselective epoxidation catalysts derived from 1,2-diaminocyclohexane J. Am. Chem. Soc. 1991, 113, 7063
33. Irie, R.; Noda, K.; Ito, Y.; Matsumoto, N.; Katsuki, T. Catalytic asymmetric epoxidation of unfunctionalized olefins using chiral (salen)manganese(III) complexes Tetrahedron: Asymm. 1991, 2, 481
34. Li, C. Chiral Synthesis on Catalysts Immobilized in Microporous and Mesoporous Materials Catal. Rev. 2004, 46, 419
35. Li, C.; Zhang, H.; Jiang, D.; Yang, Q. Chiral catalysis in nanopores of mesoporous materials Chem. Commun. 2007, 547
36. Baleizao, C.; Garcia, H. Chiral Salen Complexes: An Overview to Recoverable and Reusable Homogeneous and Heterogeneous Catalysts Chem. Rev. 2006, 106, 3987
37. Maiti, S. K.; Dinda, S.; Nandi, M.; Bhaumik, A.; Bhattacharyya, R. Selective epoxidation of olefins catalyzed by oxodiperoxomolybdenum(VI) complexes immobilized over highly ordered 2D-hexagonal mesoporous silica J. Mol. Catal. A: Chem. 2008, 287, 135
38. Jana, S.; Dutta, B.; Bera, R.; Koner, S. Anchoring of Copper Complex in MCM-41 Matrix: A Highly Efficient Catalyst for Epoxidation of Olefins by tert-BuOOH Langmuir 2007, 23, 2492
39. Sheldon, R. A.; Kochi, J. K. Metal Catalysed Oxidation of Organic Compounds; Academic Press: New York, 1981.
40. Kumar, D.; Tahsini, L.; de Visser, S. P.; Kang, H. Y.; Kim, S. J.; Nam, W. Effect of Porphyrin Ligands on the Regioselective Dehydrogenation versus Epoxidation of Olefins by Oxoiron(IV) Mimics of Cytochrome P450 J. Phys. Chem. A 2009, 113, 11713
41. Lim, M. H.; Jin, S. W.; Lee, Y. J.; Jhon, G.-J.; Nam, W.; Kim, C. Electronic Effect of Iron(III) Porphyrin Complexes on the Epoxidation of Cyclohexene: Epoxidation versus Hydroxylation Bull. Korean Chem. Soc. 2001, 22, 93
42. Sheldon, R. A.; Van Doorn, J. A. Metal-catalyzed epoxidation of olefins with organic hydroperoxides: I. A comparison of various metal catalysts J. Catal. 1973, 31, 427