Catalizador de Jacobsen inmovilizado en Al-MCM-41 y en Si-MCM-41 modificada con grupos amino y su actividad en la epoxidación enantioselectiva heterogénea utilizando dimetildioxirano generado in situ como oxidante

Autores/as

  • Jairo Cubillos Universidad de Antioquia
  • Wolfgang Hölderich RWTH Aachen University

DOI:

https://doi.org/10.17533/udea.redin.19014

Palabras clave:

Epoxidación enantioselectiva, catalizador de Jacobsen, catalizador inmovilizado, DMD generado in situ, degradación del catalizador, reutilización

Resumen

The enantioselective epoxidation of three prochiral olefins over Jacobsen’s catalyst immobilized on Al-MCM-41 and NH2-Si-MCM-41 in the presence of in situ generated DMD as the oxygen source was investigated. Experimental results indicate that the catalyst did not significantly suffer any change in its chemical structure. Therefore, the reusability of catalyst could be successfully achieved when it was immobilized by chemical bonding of the salen ligand.

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Biografía del autor/a

Jairo Cubillos, Universidad de Antioquia

Departamento de Ingeniería Química

Wolfgang Hölderich, RWTH Aachen University

Department of Chemical Technology and Heterogeneous Catalysis

Citas

V. Schürig, V. Betschinger. “Metal-mediated enantiose-lective access to unfunctionalized aliphatic: oxiranes: prochiral and chiral recognition”. Chem. Rev. Vol. 92. 1992. pp. 873-888. DOI: https://doi.org/10.1021/cr00013a006

T. Katsuki, K. B. Sharpless. “The first practical method for asymmetric”. J. Am. Chem. Soc. Vol. 102. 1980. pp. 5974-5976. DOI: https://doi.org/10.1021/ja00538a077

W. Zhang, J. L. Loebach, S. R. Wilson, E. N. Jacobsen. “Enantioselective epoxidation of unfunctionalized olefins catalyzed by (salen) manganese complexes” J. Am. Chem. Soc. Vol. 112. 1990. pp. 2801-2803. DOI: https://doi.org/10.1021/ja00163a052

R. Irie, K. Noda, Y. Ito, N. Matsumoto, T. Katsuki. “Catalytic asymmetric epoxidation of unfunctionalized olefins”. Tetrahedron Lett. Vol. 31. 1990. pp. 7345-7348. DOI: https://doi.org/10.1016/S0040-4039(00)88562-7

C. Limberg. “The role of radicals in metal-assisted oxygenation reactions” Angew. Chemie. Int. Ed. Vol. 42. 2003. pp. 5932-5954. DOI: https://doi.org/10.1002/anie.200300578

J. F. Larrow, E. N. Jacobsen. “Asymmetric Processes Catalyzed by Chiral (Salen)Metal Complexes”. Organomet. Chem. Vol. 6. 2004. pp. 123-152. DOI: https://doi.org/10.1007/b11772

E. N. Jacobsen, W. Zhang, A. R. Muci, J. R. Ecker, L. Deng. “Highly enantioselective epoxidation catalysts derived from 1,2-diaminocyclohexane”. J. Am. Chem. Soc. Vol. 113. 1991. pp. 7063-7064. DOI: https://doi.org/10.1021/ja00018a068

M. Palucki, G. J. McCormick, E. N. Jacobsen. “Low temperature asymmetric epoxidation of unfunctionalized olefins catalyzed by (salen)Mn(III) complexes”. Tetrahedron Lett. Vol. 36. 1995. pp. 5457-5460. DOI: https://doi.org/10.1016/0040-4039(95)01088-Y

R. Irie, K. Noda, Y. Ito, N. Matsumoto, T. Katsuki. “Catalytic asymmetric epoxidation of unfunctionalized olefins using chiral (salen)manganese(III) complexes”. Tetrahedron: Asymm. Vol. 2. 1991, pp. 481-494. DOI: https://doi.org/10.1016/S0957-4166(00)86102-9

M. J. Porter, J. Skidmore. “Asymmetric epoxidation of electrondeficient olefins” Chem. Commun. 2000. pp. 1215-1225. DOI: https://doi.org/10.1039/b001780i

L. Canali, D. C. Sherrington. “Utilisation of homogeneous and supported chiral metal (salen) complexes in asymmetric catalysis”. Chem. Soc. Rev. Vol. 28. 1999. pp. 85-93. DOI: https://doi.org/10.1039/a806483k

W. Zhang, E. N. Jacobsen. “Asymmetric olefin epoxidation with sodium hypochlorite catalyzed by easily prepared chiral manganese(III) salen complexes” J. Org. Chem. Vol. 56. 1991. pp. 2296-2298. DOI: https://doi.org/10.1021/jo00007a012

J. M. Fraile, J. I. García, J. Massam, J. A. Mayoral. “Claysupported non-chiral and chiral Mn(salen) complexes as catalysts for olefin epoxidation”. J. Mol. Catal. A. Vol. 136. 1998. pp. 47-57. DOI: https://doi.org/10.1016/S1381-1169(98)00013-2

I. F. J. Vankelecom, P. A. Jacobs. “Catalyst immobilization on inorganic support” En: Eds. Wiley-VCH, Weinheim.

D. E. De Vos, I. F. J. Vankelecom, P. A. Jacobs, Chiral catalyst imobilization and recycling. 2000. pp. 28-40. DOI: https://doi.org/10.1002/9783527613144

Q-H. Fan, Y-M. Li, A. S. C, Chan. “Recoverable Catalysts for Asymmetric Organic Synthesis”. Chem. Rev. Vol. 102. 2002. pp. 3385-3466. DOI: https://doi.org/10.1021/cr010341a

C. T. Kresge, M .E. Leonowicz, J. C. Roth, J. C. Vartuli, J. S. Vartuli. “Ordered mesoporous molecular sieves synthesized by a liquidcrystal template mechanism” Nature. Vol. 359. 1992, pp. 710-711. DOI: https://doi.org/10.1038/359710a0

B. De Clercq, F. Lefebvre, F. Verpoort. “Immobilization of multifunctional Schiff base containing ruthenium complexes on MCM-41”. Appl. Catal A. General. Vol. 247. 2003. pp. 345-364. DOI: https://doi.org/10.1016/S0926-860X(03)00126-1

A. Corma, M. J. Sabater, A. Domenech, V. Fornés, H. García. “Chiral salen manganese complex encapsulated within zeolite Y: a heterogeneous enantioselective catalyst for the epoxidation of alkenes”. Chem. Commun. 1997. pp. 1285-1286. DOI: https://doi.org/10.1039/a701337j

C. R. Jacob, S. P. Varkey, P. Ratnasamy. “Selective oxidation over copper and manganese salens encapsulated in zeolites”. Micropor. Mesopor. Mater. Vol. 22. 1998. pp. 465-474. DOI: https://doi.org/10.1016/S1387-1811(98)00076-6

S. B. Ogunwumi, T. Bein. “Intrazeolite assembly of a chiral manganese salen epoxidation catalyst”. Chem. Commun. 1997. pp. 901-902. DOI: https://doi.org/10.1039/a607879f

X. S. Zhao, G. Q. Lu, A. K. Whittaker, G. J. Millar, H. Y. Zhu. “Comprehensive study of surface chemistry of MCM- 41 using 29Si CP/MAS NMR, FTIR, Pyridine-TPD, and TGA. J. Phys. Chem. B. Vol. 101. 1997. pp. 6525-6531. DOI: https://doi.org/10.1021/jp971366+

D. Brühwiler, G. Calzaferri. “Molecular sieves as host materials for supramolecular organization”. Micropor. Mesopor. Mater. Vol. 72. 2004. pp. 1-23. DOI: https://doi.org/10.1016/j.micromeso.2004.03.027

H. H. Wagner, H. Hausmann, W. F. Hölderich. “Immobilization of rhodium diphosphine complexes on mesoporous Al-MCM-41 materials: catalysts for enantioselective hydrogenation”. J. catal. Vol. 203. 2001. pp. 150-156. DOI: https://doi.org/10.1006/jcat.2001.3296

C. Baleizão, B. Gigante, H. García, A. Corma. “Chiral vanadyl Schiff base complex anchored on silicas as solid enantioselective catalysts for formation of cyanohydrins: optimization of the asymmetric induction by support modification”. J Catal. Vol. 215. 2003. pp. 199-207. DOI: https://doi.org/10.1016/S0021-9517(03)00007-1

P. McMorn, G. I. Hutching. “Heterogeneous enantioselective catalysts: strategies for the immobilisation of homogeneous catalysts” Chem. Soc. Rev. Vol. 33. 2004. pp. 108-122. DOI: https://doi.org/10.1039/b200387m

W. Adam, J. Jekö, A. Lévay, C. Nemes, T. Patonay, P. Sebök. “Enantioselective epoxidation of 2,2-dimethyl-2H-chromenes by dimethyldioxirane and jacobsen’s Mn(III)salen catalysts”. Tetrahedron Lett. Vol. 36. 1995. pp. 3669-3672. DOI: https://doi.org/10.1016/0040-4039(95)00599-8

W. Adam, R. T. Fell, A. Lévai, T. Patonay, K. Peters, A. Simon, G. Tóth. “Enantioselective epoxidation of isoflavones by Jacobsen’s Mn(III)salen catalysts and dimethyldioxirane oxygen-atom source”. Tetrahedron: asymm. Vol. 9. 1998, pp. 1121-1124. DOI: https://doi.org/10.1016/S0957-4166(98)00102-5

H. M. C. Ferraz, R. M. Muzzi, T-deO Vieira, H. Viertler. “A simple and efficient protocol for epoxidation of olefins using dimethyldioxirane”. Tetrahedron Lett. Vol. 41. 2000. pp. 5021-4023. DOI: https://doi.org/10.1016/S0040-4039(00)00769-3

P. Piaggio, P. Morn, D. Murphy, D. Bethell, P. C. B. Page, F. E. Hancock, C. Sly, O. J. Kerton, G. J. Hutchings. “Enantioselective epoxidation of (Z)-stilbene using a chiral Mn(III)-salen complex : effect of immobilisation on MCM-41 on product selectivity”. J. Chem. Soc. Perkin. Trans 2. 2000. pp. 2008-2015. DOI: https://doi.org/10.1039/b005752p

C. Baleizão, B. Gigante, M. J. Sabater, H. García, A. Corma. “On the activity of chiral chromium salen complexes covalently bound to solid silicates for the enantioselective epoxide ring opening”. Appl. Catal A: General. Vol. 228. 2002, pp. 279-288. DOI: https://doi.org/10.1016/S0926-860X(01)00979-6

G. J. Kim, J. H. Shin. “The catalytic activity of new chiral salen complexes immobilized on MCM-41 by multi-step grafting in the asymmetric epoxidation”. Tetrahedron Lett. Vol. 40. 1999. pp. 6827-6830. DOI: https://doi.org/10.1016/S0040-4039(99)01407-0

J. F. Larrow, E. N. Jacobsen, Y. Gao, Y. Hong, X. Nie, C. M. Zepp. “A practical method for the large-scale preparation of [N,N’-Bis(3,5-di-tertbutylsalicylidene)-1,2 cyclohexanediaminato(2-)]manganese(III) chloride, a highly enantioselective epoxidation catalyst”. J. Org. Chem. Vol. 59. 1994, pp. 1939-1942. DOI: https://doi.org/10.1021/jo00086a062

H-R. Chang, S. K. Larsen, D. W. Boyd, C. G. Pierpont, D. N. Hendrickson. “Valence trapping in mixed-valence manganese(II)-manganese(III) complexes of a macrocyclic binucleating ligand. J. Am. Chem. Soc. Vol. 110, 1988. pp. 4565-4576. DOI: https://doi.org/10.1021/ja00222a013

E. N. Jacobsen, L. Deng, Y. Furukawa, L. E. Martínez. “Enantioselective catalytic epoxidation of cinnamate esters”. Tetrahedron. Vol. 50. 1994. pp. 4323-4334. DOI: https://doi.org/10.1016/S0040-4020(01)89369-8

R. Ryoo, C. H. Ko, R. F. Howe. “Imaging the distribution of framework aluminum in mesoporous molecular sieve MCM-41”. Chem. Mater. Vol. 9. 1997. pp. 1607-1613. DOI: https://doi.org/10.1021/cm9700110

R. G. Konsler, J. Karl, E. N. Jacobsen. “Cooperative asymmetric catalysis with dimeric salen complexes”. J. Am. Chem. Soc. Vol. 120. 1998. pp. 10780-10781. DOI: https://doi.org/10.1021/ja982683c

P. Karandikar, K. C. Dhanya, S. Deshpande, A. J. Chandwadkar, S. Sivasanker, M. Agashe. “Cu/Co-salen immobilized MCM-41: characterization and catalytic reactions”. Catal. Commun. Vol. 5. 2004. pp. 69-74. DOI: https://doi.org/10.1016/j.catcom.2003.11.015

F. Bigi, L. Moroni, R. Maggi, G. Sartori. “Heterogeneous enantioselective epoxidation of olefins catalysed by unsymmetrical (salen)Mn(III) complexes supported on amorphous or MCM-41 silica through a new triazine-based linker”. Chem. Commun. 2002. pp. 716-717. DOI: https://doi.org/10.1002/chin.200233035

C. Dalton, K. M. Ryan, V. M. Wall, C. Bousquet, D. G. Gilheany. “Recent progress towards the understanding of metal–salen catalysed asymmetric alkene epoxidation”. Topics in Catalysis. Vol. 5. 1998. pp. 75-91. DOI: https://doi.org/10.1002/chin.199839299

K. Imagawa, T. Nakata, T. Yamada, T. Mukaiyama. “N-Alkyl imidazoles as Effective axial ligands in the aerobic asymmetric epoxidation of unfunctionalized olefins catalyzed by optically active manganese(III)-salen-type complex”. Chem. Lett. Vol. 23. 1994, pp. 527-530. DOI: https://doi.org/10.1246/cl.1994.527

P. Pietikäinen. “Asymmetric Mn(III)-salen catalyzed epoxidation of unfunctionalized alkenes with generated peroxycarboxylic acids”. J. Mol. Catal A: Chem. Vol 165. 2001, pp. 73-79. DOI: https://doi.org/10.1016/S1381-1169(00)00433-7

J. A. Cubillos. “Homogeneous asymmetric epoxidation of cis-ethylcinnamate over Jacobsen’s catalyst immobilized in inorganic porous materials”. PhD thesis. RWTH university. Aachen-Germany. 2000. pp. 99-101.

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Publicado

2014-03-31

Cómo citar

Cubillos, J., & Hölderich, W. (2014). Catalizador de Jacobsen inmovilizado en Al-MCM-41 y en Si-MCM-41 modificada con grupos amino y su actividad en la epoxidación enantioselectiva heterogénea utilizando dimetildioxirano generado in situ como oxidante. Revista Facultad De Ingeniería Universidad De Antioquia, (41), 31–47. https://doi.org/10.17533/udea.redin.19014