Magnetically Separable and Recyclable Fe3O4-Supported Ag Nanocatalysts for Reduction of Nitro Compounds and Selective Hydration of Nitriles to Amides in Water
As hybrid nanostructures have become more important in many fields of chemistry, Ag nanoparticles (NPs) are being increasingly immobilized onto Fe 3O 4 microspheres in situ. Structural characterization reveals that the Ag NPs are uniformly immobilized in the Fe 3O 4 microsphere-based supports. Moreover, Ag NPs are more stable in the hybrid structure than in the naked state and show high catalytic activity for the reduction of nitro compounds and hydration of nitriles to amides in water. The Fe 3O 4 microspheres were recycled several times using an external magnet.
References
[1]
Kaneda, K.; Mitsudome, T.; Mizugaki, T.; Jitsukawa, K. Development of heterogeneous olympic medal metal nanoparticle catalysts for environmentally benign molecular transformations based on the surface properties of hydrotalcite. Molecules 2010, 15, 8988–9007, doi:10.3390/molecules15128988.
[2]
Gan, N.; Hou, J.; Hu, F.; Zheng, L.; Ni, M.; Cao, Y. An amperometric immunosensor based on a polyelectrolyte/ gold magnetic nanoparticle supramolecular assembly-modified electrode for the determination of HIV p24 in serum. Molecules 2010, 15, 5053–5065, doi:10.3390/molecules15075053.
[3]
Kamat, P.V. Meeting the clean energy demand: Nanostructure architectures for solar energy conversion. J. Phys. Chem. C 2007, 111, 2834–2860, doi:10.1021/jp066952u.
[4]
Steiner, D.; Mokari, T.; Banin, U.; Millo, O. Electronic structure of metal-semiconductor nanojunctions in gold CdSe nanodumbbells. Phys. Rev. Lett. 2005, 95, 056805, doi:10.1103/PhysRevLett.95.056805.
[5]
Haruta, M.; Yamada, N.; Kobayashi, T.; Iijima, S. Gold catalysts prepared by coprecipitation for low-temperature oxidation of hydrogen and of carbon monoxide. J. Catal. 1989, 115, 301–309, doi:10.1016/0021-9517(89)90034-1.
[6]
Chen, M.S.; Goodman, D.W. The structure of catalytically active Au on titania. Science 2004, 306, 252–255, doi:10.1126/science.1102420.
[7]
Wang, H.; You, T.; Shi, W.; Li, J.; Guo, L. Au/TiO2/Au as a plasmonic coupling photocatalyst. J. Phys. Chem. C 2012, 116, 6490–6494, doi:10.1021/jp212303q.
[8]
Chen, S.; Si, R.; Taylor, E.; Janzen, J.; Chen, J. Synthesis of Pd/Fe3O4 hybrid nanocatalysts with controllable interface and enhanced catalytic activities for CO oxidation. J. Phys. Chem. C 2012, 116, 12969–12976, doi:10.1021/jp3036204.
Miller, M.M.; Prinz, G.A.; Cheng, S.F.; Bounnak, S. Detection of a micron-sized magnetic sphere using a ring-shaped anisotropic magnetoresistance-based sensor: A model for a magnetoresistance-based biosensor. Appl. Phys. Lett. 2002, 81, 2211–2213, doi:10.1063/1.1507832.
[11]
Jain, T.K.; Morales, M.A.; Sahoo, S.K.; Leslie-Pelecky, D.L.; Labhasetwar, V. Iron oxide nanoparticles for sustained delivery of anticancer agents. Mol. Pharm. 2005, 2, 194–205, doi:10.1021/mp0500014.
[12]
Chourpa, I.; Douziech-Eyrolles, L.; Ngaboni-Okassa, L.; Fouquenet, J.F.; Cohen-Jonathan, S.; Souce, M.; Marchais, H.; Dubois, P. Molecular composition of iron oxide nanoparticles, precursors for magnetic drug targeting, as characterized by confocal Raman microspectroscopy. Analyst 2005, 130, 1395–1403, doi:10.1039/b419004a.
[13]
Jang, Y.; Chung, J.; Kim, S.; Jun, S.W.; Kim, B.H.; Lee, D.W.; Kim, B.M.; Hyeon, T. Simple synthesis of Pd–Fe3O4 heterodimer nanocrystals and their application as a magnetically recyclable catalyst for Suzuki cross-coupling reactions. Phys. Chem. Chem. Phys. 2011, 13, 2512–2516, doi:10.1039/c0cp01680b.
[14]
Zhai, Q.-G.; Hu, M.-C.; Li, S.-N.; Jiang, Y.-C. Synthesis, structure and blue luminescent properties of a new silver(I) triazolate coordination polymer with 8210-a topology. Inorg. Chim. Acta 2009, 362, 1355–1357, doi:10.1016/j.ica.2008.05.014.
[15]
Lee, D.; Cohen, R.E.; Rubner, M.F. Antibacterial properties of Ag nanoparticle loaded multilayers and formation of magnetically directed antibacterial microparticles. Langmuir 2005, 21, 9651–9659, doi:10.1021/la0513306.
[16]
Luo, X.; Morrin, A.; Killard, A.J.; Smyth, M.R. Application of nanoparticles in electrochemical sensors and biosensors. Electroanalysis 2006, 18, 319–326, doi:10.1002/elan.200503415.
[17]
Mitsudome, T.; Mikami, Y.; Funai, H.; Mizugaki, T.; Jitsukawa, K.; Kaneda, K. Oxidant-free alcohol dehydrogenation using a reusable hydrotalcite-supported silver nanoparticle catalyst. Angew. Chem. 2008, 120, 144–147, doi:10.1002/ange.200703161.
[18]
Guan, Y.; Li, Y.; van Santen, R.A.; Hensen, E.J.M.; Li, C. Controlling reaction pathways for alcohol dehydration and dehydrogenation over FeSBA-15 catalysts. Catal. Lett. 2007, 117, 18–24, doi:10.1007/s10562-007-9151-4.
Cong, H.; Becker, C.F.; Elliott, S.J.; Grinstaff, M.W.; Porco, J.A., Jr. Silver nanoparticle-catalyzed Diels-Alder cycloadditions of 2'-hydroxychalcones. J. Am. Chem. Soc. 2010, 132, 7514–7518, doi:10.1021/ja102482b.
[21]
Narayanan, R.; El-Sayed, M.A. Catalysis with transition metal nanoparticles in colloidal solution: Nanoparticle shape dependence and stability. J. Phys. Chem. B 2005, 109, 12663–12676, doi:10.1021/jp051066p.
[22]
Motokura, K.; Fujita, N.; Mori, K.; Mizugaki, T.; Ebitani, K.; Kaneda, K. One-pot synthesis of α-alkylated nitriles with carbonyl compounds through consecutive aldol reaction/hydrogenation using a hydrotalcite-supported palladium nanoparticle as a multifunctional heterogeneous catalyst. Tetrahedron Lett. 2005, 46, 5507–5510, doi:10.1016/j.tetlet.2005.06.053.
Li, C.M.; Taneda, S.; Suzuki, A.K.; Furuta, C.; Watanabe, G.; Taya, K. Estrogenic and anti-androgenic activities of 4-nitrophenol in diesel exhaust particles. Toxicol. Appl. Pharmacol. 2006, 217, 1–6, doi:10.1016/j.taap.2006.06.010.
[25]
Pradhan, N.; Pal, A.; Pal, T. Catalytic reduction of aromatic nitro compounds by coinage metal nanoparticles. Langmuir 2001, 17, 1800–1802, doi:10.1021/la000862d.
[26]
Esumi, K.; Isono, R.; Yoshimura, T. Preparation of PAMAM- and PPI-metal (silver, platinum, and palladium) nanocomposites and their catalytic activities for reduction of 4-nitrophenol. Langmuir 2004, 20, 237–243, doi:10.1021/la035440t.
[27]
Zhang, P.; Shao, C.; Zhang, Z.; Zhang, M.; Mu, J.; Guoab, Z.; Liua, Y. In situ assembly of well-dispersed Ag nanoparticles (AgNPs) on electrospun carbon nanofibers (CNFs) for catalytic reduction of 4-nitrophenol. Nanoscale 2011, 3, 3357–3363, doi:10.1039/c1nr10405e.
[28]
Shimizua, K.; Imaiidab, N.; Sawabeb, K.; Satsuma, A. Hydration of nitriles to amides in water by SiO2-supported Ag catalysts promoted by adsorbed oxygen atoms. Appl. Catal. A-Gen. 2012, 421–422, 114–120.
[29]
Mitsudome, T.; Mikami, Y.; Mori, H.; Arita, S.; Mizugaki, T.; Jitsukawa, K.; Kaneda, K. Supported silver nanoparticle catalyst for selective hydration of nitriles to amides in water. Chem. Commun. 2009, 3258–3260.
[30]
Kim, A.Y.; Bae, H.S.; Park, S.; Park, S.; Park, K.H. Silver nanoparticle catalyzed selective hydration of nitriles to amides in water under neutral conditions. Catal. Lett. 2011, 141, 685–690, doi:10.1007/s10562-011-0561-y.
[31]
Liu, B.; Zhang, W.; Yang, F.; Feng, H.; Yang, X. Facile method for synthesis of Fe3O4@Polymer microspheres and their application as magnetic support for loading metal nanoparticles. J. Phys. Chem. C 2011, 115, 15875–15884, doi:10.1021/jp204976y.
[32]
Hu, H.; Wang, Z.; Pan, L.; Zhao, S.; Zhu, S. Ag-coated Fe3O4@SiO2 three-ply composite microspheres: Synthesis, characterization, and application in detecting melamine with their surface-enhanced raman scattering. J. Phys. Chem. C 2010, 114, 7738–7742, doi:10.1021/jp100141c.
[33]
Liu, P.; Zhao, M. Silver nanoparticle supported on halloysite nanotubes catalyzed reduction of 4-nitrophenol (4-NP). Appl. Surf. Sci. 2009, 255, 3989–3993.
[34]
Jana, S.; Ghosh, S.K.; Nath, S.; Pande, S.; Praharaj, S.; Panigrahi, S.; Basu, S.; Endo, T.; Pal, T. Synthesis of silver nanoshell-coated cationic polystyrene beads: A solid phase catalyst for the reduction of 4-nitrophenol. Appl. Catal. A-Gen. 2006, 313, 41–48, doi:10.1016/j.apcata.2006.07.007.
