Abstract
A series of highly porous metal organic framework ZIF-8 supported Au nanoparticles materials with different Au particle size were prepared through one-pot method at room temperature. The obtained heterogeneous catalysts were comprehensively characterized by powder X-ray diffraction, N2 adsorption, FTIR spectroscopy, scanning electron microscope and transmission electron microscopy. The intact crystallinity of ZIF-8 was found before and after the Au loading, and Au nanoparticles with different particle size were found homogeneously dispersed in ZIF-8. The obtained Au catalysts exhibited high activity and stability for hydrogenation of 4-nitrophenol, with excellent selectivity to aminophenol. It had been shown that the Au particle size played important roles in the activity. The as-prepared catalysts exhibit relatively excellent activity and selectivity in the reduction of p-nitrobenzonitrile to p-aminobenzonitrile, which is benefit from the high selectivity of Au particles.
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Eddaoudi M, Sava DF, Eubank JF, Adil K, Guillerm V (2015) Zeolite-like metal-organic frameworks (ZMOFs): design, synthesis, and properties. Chem Soc Rev 44:228–249
Yin DD, Li C, Ren HX, Shekhah O, Liu JX, Liang CH (2017) Efficient Pd@MIL-101 (Cr) hetero-catalysts for 2-butyne-1, 4-diol hydrogenation exhibiting high selectivity. RSC Adv 7:1626–1633
Ren HX, Li C, Yin DD, Liu JX, Liang CH (2016) Pd@MIL-101 as an efficient bifunctional catalyst for hydrodeoxygenation of anisole. RSC Adv 6:85659–85665
Ferey G (2008) Hybrid porous solids: past, present, future. Chem Soc Rev 37:191–214
Yaghi OM, O’Keeffe M, Ockwig NW, Chae HK, Eddaoudi M, Kim J (2003) Reticular synthesis and the design of new materials. Nature 423:705–714
Furukawa H, Cordova KE, O’Keeffe M, Yaghi OM (2013) The chemistry and applications of metal-organic frameworks. Science 341:1230444–1230445
Li JR, Kuppler RJ, Zhou HC (2009) Selective gas adsorption and separation in metal-organic frameworks. Chem Soc Rev 38:1477–1504
Chen LJ, Yan JQ, Tong ZX, Yu SY, Tang JT, Ou BL, Yue LJ, Tian L (2018) Nanofiber-like mesoporous alumina supported palladium nanoparticles as a highly active catalyst for base-free oxidation of benzyl alcohol. Microporous Mesoporous Mater 266:126–131
Dhakshinamoorthy A, Garcia H (2012) Catalysis by metal nanoparticles embedded on metal-organic frameworks. Chem Soc Rev 41:5262–5284
Isaeva VI, Eliseev OL, Chernyshev VV, Bondarenko TN, Vergun VV, Kustov LM (2019) Palladium nanoparticles embedded in MOF matrices: catalytic activity and structural stability in iodobenzene methoxycarbonylation. Polyhedron 158:55–64
Farrusseng D, Aguado S, Pinel C (2009) Metal-organic frameworks: opportunities for catalysis. Angew Chem Int Ed 48:7502–7513
Aijaz A, Akita T, Tsumori N, Xu Q (2013) Metal-Organic Framework-Immobilized Polyhedral Metal Nanocrystals: reduction at Solid-Gas Interface, Metal Segregation, Core-Shell Structure, and High Catalytic Activity. J Am Chem Soc 135:16356–16359
Zhang MM, Yang YB, Li C, Liu Q, Williams CT, Liang CH (2014) PVP-Pd@ZIF-8 as highly efficient and stable catalysts for selective hydrogenation of 1, 4-butynediol. Catal Sci Technol 4:329–332
Haruta M, Yamada N, Kobayashi T, Lijima S (1988) Gold catalysts prepared by coprecipitation for low-temperature oxidation of hydrogen and of carbon monoxide. J Catal 115:301–309
Qi C, Huang J, Bao S, Su H, Akita T, Haruta M (2011) Switching of reactions between hydrogenation and epoxidation of propene over Au/Ti-based oxides in the presence of H2 and O2. J Catal 281:12–20
Takei T, Akita T, Nakamura I, Fujitani T, Okumura M, Okazaki K, Huang J, Ishida T, Haruta M (2012) Heterogeneous catalysis by gold. Adv Catal 55:1–124
Rudolph M, Hashmi ASK (2012) Gold catalysis in total synthesis-an update. Chem Soc Rev 41:2448–2462
Chen X, Zhu HY, Zhao JC, Zheng ZF, Gao XP (2008) Visible-light-driven oxidation of organic contaminants in air with gold nanoparticle catalysts on oxide supports. Angew Chem Int Ed 47:5353–5356
Liu LL, Zhou XJ, Yan YM, Zhou J, Zhang WP, Tai XS (2018) Bimetallic gold-silver nanoparticles supported on zeolitic imidazolate framework-8 as highly active heterogenous catalysts for selective oxidation of benzyl alcohol into benzaldehyde. Polymer 10:1089–1094
Wang H, Fan WB, He Y, Wang JG, Kondo JN, Tatsumi T (2013) Selective oxidation of alcohols to aldehydes/ketones over copper oxide-supported gold catalysts. J Catal 299:10–19
Liu LL, Tai XS, Zhou XJ, Hou JX, Zhang ZH (2019) Bimetallic Au–Ni alloy nanoparticles in a metal–organic framework (MIL-101) as efficient heterogeneous catalysts for selective oxidation of benzyl alcohol into benzaldehyde. J Alloys Compd 790:326–336
Corma A, Gonzalez-Arellano C, Sanchez MIF (2009) Gold complexes as catalysts: chemoselective hydrogenation of nitroarenes. Appl Catal A 356:99–102
Corma A, Serna P (2006) Chemoselective hydrogenation of nitro compounds with supported gold catalysts. Science 313:332–334
Wang XD, Hao YF, Keane MA (2016) Selective gas phase hydrogenation of p-nitrobenzonitrile to p-aminobenzonitrile over zirconia supported gold. Appl Catal A 510:171–179
Sun LB, Sun X, Zheng YH, Lin QQ, Su HJ, Qi CX (2017) Fabrication and characterization of core-shell polystyrene/polyaniline/Au composites and their catalytic properties for the reduction of 4-nitrophenol. Synth Met 224:1–6
Yin DD, Li C, Ren HX, Liu JX, Liang CH (2018) Gold-palladium-alloy-catalyst loaded UiO-66-NH2 for reductive amination with nitroarenes exhibiting high selectivity. ChemistrySelect 3:5092–5097
Zhang MM, GaoY Li C, Liang CH (2015) Chemical vapor deposition of Pd (C3H5)(C5H5) for the synthesis of reusable Pd@ZIF-8 catalysts for the Suzuki coupling reaction. Chin J Catal 36:588–594
Ishida T, Ogihara Y, Ohashi H, Akita T, Honma T, Oji H, Haruta M (2012) Base-free direct oxidation of 1-octanol to octanoic acid and its octyl Ester over supported gold catalysts. Chemsuschem 5:2243–2248
Claus P (2005) Heterogeneously catalysed hydrogenation using gold catalysts. Appl Catal A 291:222–229
Zanella R, Louis C, Giorgio S, Touroude R (2004) Crotonaldehyde hydrogenation by gold supported on TiO2: structure sensitivity and mechanism. J Catal 223:328–339
Cárdenas-Lizana F, Gómez-Quero S, Idriss H, Keane MA (2009) Gold particle size effects in the gas-phase hydrogenation of m-dinitrobenzene over Au/TiO2. J Catal 268:223–234
Chen JC, Zhang RY, Han L, Tu B, Zhao DY (2013) One-pot synthesis of thermally stable gold@ mesoporous silica core-shell nanospheres with catalytic activity. Nano Res 6:871–879
Lee J, Park JC, Song HA (2008) Nanoreactor Framework of a Au@SiO2 Yolk/Shell Structure for Catalytic Reduction of p-Nitrophenol. Adv Mater 20:1523–1528
Koprivova K, Cerveny L (2008) Hydrogenation of nitrobenzonitriles using Raney nickel catalyst. Res Chem Intermed 34:93–101
Wang X, Perret N, Keane MA (2012) The role of hydrogen partial pressure in the gas phase hydrogenation of p-chloronitrobenzene over alumina supported Au and Pd: a consideration of reaction. Chem Eng J 210:103–113
Wang X, Perret N, Keane MA (2013) Gas phase hydrogenation of nitrocyclohexane over supported gold catalysts. Appl Catal A 467:575–584
Wang X, Perret N, Delgado JJ, Blanco G, Chen X, Olmos CM, Bernal S, Keane MA (2013) Reducible support effects in the gas phase hydrogenation of p-Chloronitrobenzene over gold. J Phys Chem C 117:994–1005
Chan CWA, Xie Y, Cailuo N, Yu KMK, Cookson J, Bishop P, Tsang SC (2011) New environmentally friendly catalysts containing Pd–interstitial carbon made from Pd–glucose precursors for ultraselective hydrogenations in the liquid phase. Chem Commun 47:7971–7973
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We gratefully acknowledge the financial support provided by the National Natural Science Foundation of China (21802118) and Shandong Provincial Natural Science Foundation, China (ZR2018BB041).
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Zhang, M., Liu, Q., Sun, L. et al. Synthesis of High Efficient and Stable Au@ZIF-8 with Difference Particle Size for Chemselective Hydrogenation of Nitro Compounds. Catal Lett 150, 438–449 (2020). https://doi.org/10.1007/s10562-019-02963-9
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DOI: https://doi.org/10.1007/s10562-019-02963-9