全部 标题 作者
关键词 摘要

OALib Journal期刊
ISSN: 2333-9721
费用:99美元

查看量下载量

相关文章

更多...

Magnetically Separable Base Catalysts: Heterogeneous Catalysis vs. Quasi-Homogeneous Catalysis

DOI: 10.3390/app2020260

Keywords: magnetic nanoparticles, sol-gel chemistry, heterogeneous catalysis, quasi-homogeneous catalysis, base catalysis

Full-Text   Cite this paper   Add to My Lib

Abstract:

The synthesis of magnetically separable quasi-homogeneous base catalyst and heterogeneous base catalyst is described. The quasi-homogeneous catalyst is achieved by supporting silane monomers functionalized with different amine groups directly on the surface of magnetite nanoparticles. The heterogeneous catalyst is prepared via a sol-gel process in which silane monomers containing different amine groups are copolymerized with tetraethoxysilane in the presence of magnetite nanoparticles functionalized with ionic liquid moieties. The reactivity of the quasi-homogeneous and the heterogeneous base catalysts is compared in the nitroaldol condensation.

References

[1]  Recoverable and Recyclable Catalysts; Benaglia, M., Ed.; John Wiley & Sons: Chichester, UK, 2009.
[2]  Lu, Z.; Lindner, E.; Mayer, H.A. Applications of sol-gel-processed interphase catalysts. Chem. Rev. 2002, 102, 3543–3578, doi:10.1021/cr010358t.
[3]  Marr, A.C.; Marr, P.C. Entrapping homogeneous catalysts by sol-gel methods: The bottom-up synthesis of catalysts that recycle and cascade. Dalton Trans. 2011, 40, 20–26, doi:10.1039/c0dt00888e.
[4]  Zamboulis, A.; Moitra, N.; Moreau, J.J.E.; Catto?n, X.; Wong Chi Man, M. Hybrid materials: Versatile matrices for supporting homogeneous catalysts. J. Mater. Chem. 2010, 20, 9322–9338, doi:10.1039/c000334d.
[5]  Ciriminna, R.; Demma Carà, P.; Sciortino, M.; Pagliaro, M. Catalysis with doped sol-gel silicates. Adv. Synth. Catal. 2011, 353, 677–687, doi:10.1002/adsc.201000731.
[6]  Ciriminna, R.; Pagliaro, M. Recent uses of sol-gel doped catalysts in the fine chemicals and pharmaceutical industry. Org. Process Res. Dev. 2006, 10, 320–326.
[7]  Sch?tz, A.; Reiser, O.; Stark, W.J. Nanoparticles as semi-heterogeneous catalyst supports. Chem. Eur. J. 2010, 16, 8950–8967, doi:10.1002/chem.200903462.
[8]  Astruc, D.; Lu, F.; Aranzaes, J.R. Nanoparticles as recyclable catalysts: The frontier between homogeneous and heterogeneous catalysis. Angew. Chem. Int. Ed. 2005, 44, 7852–7872, doi:10.1002/anie.200500766.
[9]  Gupta, A.K.; Curtis, A.S.G. Surface modified superparamagnetic nanoparticles for drug delivery: Interaction studies with human fibroblasts in culture. J. Mater. Sci. Mater. Med. 2004, 15, 493–496, doi:10.1023/B:JMSM.0000021126.32934.20.
[10]  Neuberger, T.; Schoepf, B.; Hofmann, H.; Hofmann, M.; von Rechenberg, B. Superparamagnetic nanoparticles for biomedical applications: possibilities and limitations of a new drug delivery system. J. Magn. Magn. Mater. 2005, 293, 483–496, doi:10.1016/j.jmmm.2005.01.064.
[11]  Pankhurst, Q.A.; Connolly, J.; Jones, S.K.; Dobson, J. Applications of magnetic nanoparticles in biomedicine. J. Phys. D: Appl. Phys. 2003, 36, R167–R181, doi:10.1088/0022-3727/36/13/201.
[12]  Perez, J.M.; Simeone, F.J.; Saeki, Y.; Josephson, L.; Weissleder, R. Viral-induced self-assembly of magnetic nanoparticles allows the detection of viral particles in biological media. J. Am. Chem. Soc. 2003, 125, 10192–10193.
[13]  Graham, D.L.; Ferreira, H.A.; Freitas, P.P. Magnetoresistive-based biosensors and biochips. Trends Biotechnol. 2004, 22, 455–462, doi:10.1016/j.tibtech.2004.06.006.
[14]  Wang, D.; He, J.; Rosenzweig, N.; Rosenzweig, Z. Nano Lett. 2004, 4, 409–413.
[15]  Xu, C.; Xu, K.; Gu, H.; Zheng, R.; Liu, H.; Zhang, X.; Guo, Z.; Xu, B. Dopamine as a robust anchor to immobilize functional molecules on the iron oxide shell of magnetic nanoparticles. J. Am. Chem. Soc. 2004, 126, 9938–9939.
[16]  Hiergeist, R.; Andra, W.; Buske, N.; Hergt, R.; Hilger, I.; Richter, U.; Kaiser, W. Application of magnetite ferrofluids for hyperthermia. J. Magn. Magn. Mater. 1999, 201, 420–422, doi:10.1016/S0304-8853(99)00145-6.
[17]  Jordan, A.; Scholz, R.; Wust, P.; Fahling, H.; Felix, R. Magnetic fluid hyperthermia (MFH): Cancer treatment with AC magnetic field induced excitation of biocompatible superparamagnetic nanoparticles. J. Magn. Magn. Mater. 1999, 201, 413–419, doi:10.1016/S0304-8853(99)00088-8.
[18]  Polshettiwar, V.; Luque, R.; Fihri, A.; Zhu, H.; Bouhrara, M.; Basset, J.M. Magnetically recoverable nanocatalysts. Chem. Rev. 2011, 111, 3036–3075, doi:10.1021/cr100230z.
[19]  Shyles, S.; Schünemann, V.; Thiel, W.R. Magnetically separable nanocatalysts: Bridges between homogeneous and heterogeneous catalysis. Angew. Chem. Int. Ed. 2010, 49, 3428–3459.
[20]  Zhu, Y.; Stubbs, L.P.; Ho, F.; Liu, R.; Ship, C.P.; Maguire, J.A.; Hosmane, N.S. Magnetic nanocomposites: A new perspective in catalysis. ChemCatChem 2010, 2, 365–374, doi:10.1002/cctc.200900314.
[21]  Polshettiwar, V.; Varma, R.S. Green chemistry by nano-catalysis. Green Chem. 2010, 12, 743–754, doi:10.1039/b921171c.
[22]  Kawamura, M.; Sato, K. Magnetically separable phase-transfer catalysts. Chem. Commun. 2006, 4718–4719, doi:10.1039/b611906a.
[23]  Lee, D.; Lee, J.; Lee, H.; Jin, S.; Hyeon, T.; Kim, B.M. Filtration-free recyclable catalytic asymmetric dihydroxylation using a ligand immobilized on magnetic mesocellular mesoporous silica. Adv. Synth. Catal. 2006, 348, 41–46, doi:10.1002/adsc.200505354.
[24]  Luo, S.; Zheng, X.; Xu, H.; Mi, X.; Zhang, L.; Cheng, J.P. Magnetic nanoparticle-supported Morita-Baylis-Hillman catalysts. Adv. Synth. Catal. 2007, 349, 2431–2434, doi:10.1002/adsc.200700318.
[25]  Dálaigh, C.ó.; Corr, S.A.; Gun'ko, Y.; Connon, S.J. A magnetic-nanoparticle-supported 4-N,N-dialkylaminopyridine catalyst: Excellent reactivity combined with facile catalyst recovery and recyclability. Angew. Chem. Int. Ed. 2007, 46, 4329–4332.
[26]  Luo, S.; Zheng, X.; Cheng, J.-P. Asymmetric bifunctional primary aminocatalysis on magnetic nanoparticles. Chem. Commun. 2008, 5719–5721.
[27]  Sch?tz, A.; Grass, R.N.; Stark, W.J.J.; Reiser, O. TEMPO supported on magnetic C/Co-nanoparticles: A highly active and recyclable organocatalyst. Chem. Eur. J. 2008, 14, 8262–8266.
[28]  Gleeson, O.; Tekoriute, R.; Gun'ko, Y.K.; Connon, S.J. The first magnetic nanoparticle-supported chiral DMAP analogue: Highly enantioselective acylation and excellent recyclability. Chem. Eur. J. 2009, 15, 5669–5673, doi:10.1002/chem.200900532.
[29]  Wang, B.G.; Ma, B.C.; Wang, Q.; Wang, W. Superparamagnetic nanoparticle-supported (S)-diphenyl-prolinol trimethylsilyl ether as a recyclable catalyst for asymmetric Michael addition in water. Adv. Synth. Catal. 2010, 352, 2923–2928, doi:10.1002/adsc.201000508.
[30]  Polshettiwar, V.; Baruwati, B.; Varma, R.S. Magnetic nanoparticle-supported glutathione: A conceptually sustainable organocatalyst. Chem. Commun. 2009, 1837–1839.
[31]  Polshettiwar, V.; Varma, R.S. Nano-organocatalyst: Magnetically retrievable ferrite-anchored glutathione for microwave-assisted Paal-Knorr reaction, aza-Michael addition, and pyrazole synthesis. Tetrahedron 2010, 66, 1091–1097, doi:10.1016/j.tet.2009.11.015.
[32]  Riente, P.; Mendoza, C.; Pericás, M.A. Functionalization of Fe3O4 magnetic nanoparticles for organocatalytic Michael reactions. J. Mater. Chem. 2011, 21, 7350–7355.
[33]  Abu-Reziq, R.; Alper, H.; Wang, D.; Post, M.L. Metal supported on dendronized magnetic nanoparticles: Highly selective hydroformylation catalysts. J. Am. Chem. Soc. 2006, 128, 5279–5282.
[34]  Abu-Reziq, R.; Wang, D.; Post, M.L.; Alper, H. Platinum nanoparticles supported on ionic liquid-modified magnetic nanoparticles: Selective hydrogenation catalysts. Adv. Synth. Catal. 2007, 349, 2145–2150, doi:10.1002/adsc.200700129.
[35]  Abu-Reziq, R.; Wang, D.; Post, M.L.; Alper, H. Separable catalysts in one-pot syntheses for greener chemistry. Chem. Mater. 2008, 20, 2544–2550.
[36]  Jones, G. The Knoevenagel condensation. Org. React. 1967, 15, 204–599.
[37]  Barret, A.G.M.; Graboski, G.G. Conjugated nitroalkenes: Versatile intermediates in organic synthesis. Chem. Rev. 1986, 86, 751–762.
[38]  Ballini, R.; Bosica, G.; Fiorini, D.; Palmieri, A. One-pot synthesis of 1,3-dinitroalkanes under heterogeneous catalysis. Synthesis 2004, 1938–1940.
[39]  Kantam, M.L.; Choudary, B.M.; Reddy, C.V.; Rao, K.K.; Figueras, F. Aldol and Knoevenagel condensations catalysed by modified Mg-Al hydrotalcite: A solid base as catalyst useful in synthetic organic chemistry. Chem Commun. 1998, 1033–1034.
[40]  Bulbule, V.J.; Deshpande, V.H.; Velu, S.; Sudalai, A.; Sivasankar, S.; Sathe, V.T. Heterogeneous Henry reaction of aldehydes: Diastereoselective synthesis of nitroalcohol derivatives over Mg-Al hydrotalcites. Tetrahedron 1999, 55, 9325–9332, doi:10.1016/S0040-4020(99)00494-9.
[41]  Akutu, K.; Kabashima, H.; Seki, T.; Hattori, H. Nitroaldol reaction over solid base catalysts. Appl. Catal.A 2003, 247, 65–74, doi:10.1016/S0926-860X(03)00124-8.
[42]  Khan, F.A.; Dash, J.; Satapathy, R.; Upadhyay, S.K. Hydrotalcite catalysis in ionic liquid medium: A recyclable reaction system for heterogeneous Knoevenagel and nitroaldol condensation. Tetraheron Lett. 2004, 45, 3055–3058.
[43]  Choudary, B.M.; Kantam, M.L.; Reddy, C.V.; Rao, K.K.; Figueras, F. Henry reactions catalysed by modified Mg-Al hydrotalcite: An efficient reusable solid base for selective synthesis of beta-nitroalkanols. Green Chem. 1999, 187–189.
[44]  Saito, T.; Goto, H.; Honda, K.; Fujii, T.T. Acid-base catalysts derived from weakly acidic ion-exchange resin:Efficiency in the Knoevenagel condensation. Tetrahedron Lett. 1992, 33, 7535–7538, doi:10.1016/S0040-4039(00)60817-1.
[45]  Hein, R.W.; Astle, M.J.; Shelton, J.R. Ion-exchange Resin Catalysis of the Knoevenagel Condensation of Ketones. J. Org. Chem. 1961, 26, 4874–4878, doi:10.1021/jo01070a022.
[46]  Ballini, R.; Bosica, G.; Forconi, P. Nitroaldol (Henry) reaction catalyzed by Amberlyst A-21 as a far superior heterogeneous catalyst. Tetrahedron 1996, 52, 1677–1684, doi:10.1016/0040-4020(95)00996-5.
[47]  Angeletti, E.; Canepa, C.; Martinetti, G.; Venturello, P. Amino-groups immobilized on silica-gel—An efficient reusable heterogeneous catalyst for the Knoevenagel condensation. J. Chem. Soc., Perkin Trans. 1989, 1, 105–107.
[48]  Ballini, R.; Bosica, G.; Livi, D.; Palmieri, A.; Maggi, R.; Sartori, G. Use of heterogeneous catalyst KG-60-NEt2 in Michael and Henry reactions involving nitroalkanes. Tetrahedron Lett. 2003, 44, 2271–2273.
[49]  Corma, A.; Fornes, V.; Martin-Aranda, R.M.; Garcia, H.; Primo, J. Zeolite as base catalysts— Condensation of aldehydes with derivatives of malonic esters. Appl. Catal. 1990, 59, 237–248, doi:10.1016/S0166-9834(00)82201-0.
[50]  Kubota, Y.; Nishizaki, Y.; Ikeya, H.; Saeki, M.; Hida, T.; Kawazu, S.; Yoshida, M.; Fujii, H.; Sugi, Y. Organic-silicate hybrid catalysts based on various defined structures for Knoevenagel condensation. Micropor. Mesopor. Mater. 2004, 70, 135–149, doi:10.1016/j.micromeso.2004.02.017.
[51]  Jaenicke, S.; Chuah, G.K.; Lin, X.H.; Hu, X.C. Organic-inorganic hybrid catalysts for acid- and base-catalyzed reactions. Micropor. Mesopor. Mater. 2000, 35-36, 143–153, doi:10.1016/S1387-1811(99)00215-2.
[52]  Inaki, Y.; Kajita, Y.; Yoshida, H.; Ito, K.; Hattori, T. New basic mesoporous silica catalyst obtained by ammonia grafting. Chem. Commun. 2001, 2358–2359.
[53]  Huh, S.; Chen, H.-T.; Wiench, J.W.; Pruski, M.; Lin, V.S.-Y. Controlling the selectivity of competitive nitroaldol condensation by using a bifunctionalized mesoporous silica nanosphere-based catalytic system. J. Am.Chem. Soc. 2004, 126, 1010–1011.
[54]  Rodriguez, I.; Iborra, S.; Corma, A.; Rey, F.; Jordá, J.L. MCM-41-Quaternary organic tetraalkylammonium hydroxide composites as strong and stable Bronsted base catalysts. Chem. Commun. 1999, 593–594.
[55]  Phan, N.T.S.; Jones, C.W. Highly accessible catalytic sites on recyclable organosilane-functionalized magnetic nanoparticles: An alternative to functionalized porous silica catalysts. J. Mol. Catal. A: Chem. 2006, 253, 123–131, doi:10.1016/j.molcata.2006.03.019.
[56]  Zhang, Y.; Zhao, Y.; Xia, C. Basic ionic liquids supported on hydroxyapatite-encapsulated γ-Fe2O3 nanocrystallites: An efficient magnetic and recyclable heterogeneous catalyst for aqueous Knoevenagel condensation. J. Mol. Catal. A: Chem. 2009, 306, 107–112, doi:10.1016/j.molcata.2009.02.032.
[57]  Gill, C.G.; Long, W.; Jones, C.W. Magnetic nanoparticle polymer brush catalysts: Alternative hybrid organic/inorganic structures to obtain high, local catalyst loadings for use in organic transformations. Catal. Lett. 2009, 131, 425–431, doi:10.1007/s10562-009-0099-4.
[58]  Gao, Z.; Zhou, J.; Cui, F.; Zhu, Y.; Hua, Z.; Shi, J. Superparamagnetic mesoporous Mg-Fe bi-metal oxides as efficient magnetic solid-base catalysts for Knoevenagel condensations. Dalton Trans. 2010, 39, 11132–11135.
[59]  Senapati, K.K.; Borgohain, C.; Phukan, P. Synthesis of highly stable CoFe2O4 nanoparticles and their use as magnetically separable catalyst for Knoevenagel reaction in aqueous medium. J. Mol. Catal. A: Chem. 2011, 339, 24–31, doi:10.1016/j.molcata.2011.02.007.

Full-Text

comments powered by Disqus

Contact Us

service@oalib.com

QQ:3279437679

WhatsApp +8615387084133