Abstract
Pt@MAF-6 was designed as a highly selective catalyst for cinnamaldehyde hydrogenation. The aperture of Pt@MAF-6 acted to sterically confine cinnamaldehyde, and 94% selectivity to cinnamic alcohol was obtained at a high conversion of 95%. Steric confinement was inefficient in trans-2-pentenal hydrogenation, showing that encapsulating active sites within a commensurate porous support is important for a steric effect catalyst.
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Li JR, Sculley J, Zhou HC (2012) Metal–organic frameworks for separations. Chem Rev 112:869–932
Kreno LE, Leong K, Farha OK, Allendorf M, Van Duyne RP, Hupp JT (2012) Metal–organic framework materials as chemical sensors. Chem Rev 112:1105–1125
Huxford RC, Della Rocca J, Lin W (2010) Metal–organic frameworks as potential drug carriers. Curr Opin Chem Biol 14:262–268
Zhao S-N, Song X-Z, Song S-Y, Zhang H-J (2017) Highly efficient heterogeneous catalytic materials derived from metal-organic framework supports/precursors. Coordin Chem Rev 337:80–96
Yang Q, Xu Q, Jiang HL (2017) Metal–organic frameworks meet metal nanoparticles: synergistic effect for enhanced catalysis. Chem Soc Rev 46:4774–4808
Liu J, Chen L, Cui H, Zhang J, Zhang L, Su CY (2014) Applications of metal–organic frameworks in heterogeneous supramolecular catalysis. Chem Soc Rev 43:6011–6061
Hu P, Morabito JV, Tsung C-K (2014) Core–shell catalysts of metal nanoparticle core and metal–organic framework shell. ACS Catal 4:4409–4419
Zhang W, Lu G, Cui C, Liu Y, Li S et al (2014) A family of metal-organic frameworks exhibiting size-selective catalysis with encapsulated noble-metal nanoparticles. Adv Mater 26:4056–4060
Chen Y-Z, Zhou Y-X, Wang H, Lu J, Uchida T et al (2015) Multifunctional PdAg@ MIL-101 for one-pot cascade reactions: combination of host–guest cooperation and bimetallic synergy in catalysis. ACS Catal 5:2062–2069
Gallezot P, Richard D (1998) Selective hydrogenation of α, β-unsaturated aldehydes. Catal Rev 40:81–126
Kliewer CJ, Bieri M, Somorjai GA (2009) Hydrogenation of the α, β-unsaturated aldehydes acrolein, crotonaldehyde, and prenal over Pt single crystals: a kinetic and sum-frequency generation vibrational spectroscopy study. J Am Chem Soc 131:9958–9966
Kennedy G, Baker LR, Somorjai GA (2014) Selective Amplification of C=O bond hydrogenation on Pt/TiO2: catalytic reaction and sum-frequency generation vibrational spectroscopy studies of crotonaldehyde hydrogenation. Angew Chem Int Ed Engl 53:3405–3408
Mäki-Arvela P, Hájek J, Salmi T, Murzin DY (2005) Chemoselective hydrogenation of carbonyl compounds over heterogeneous catalysts. Appl Catal A-Gen 292:1–49
Tian Z, Xiang X, Xie L, Li F (2012) Liquid-phase hydrogenation of cinnamaldehyde: enhancing selectivity of supported gold catalysts by incorporation of cerium into the support. Ind Eng Chem Res 52:288–296
Lan X, Wang T (2020) Highly selective catalysts for the hydrogenation of unsaturated aldehydes: a review. ACS Catal 10:2764–2790
Ide MS, Hao B, Neurock M, Davis RJ (2012) Mechanistic insights on the hydrogenation of α, β-unsaturated ketones and aldehydes to unsaturated alcohols over metal catalysts. ACS Catal 2:671–683
Ammari F, Milone C, Touroude R (2005) Selective hydrogenation of crotonaldehyde on Pt/ZnCl2/SiO2 catalysts. J Catal 235:1–9
Durndell LJ, Parlett CMA, Hondow NS, Isaacs MA, Wilson K, Lee AF (2015) Selectivity control in Pt-catalyzed cinnamaldehyde hydrogenation. Sci Rep 5:9425
Merlo AB, Machado BF, Vetere V, Faria JL, Casella ML (2010) PtSn/SiO2 catalysts prepared by surface controlled reactions for the selective hydrogenation of cinnamaldehyde. Appl Catal A-Gen 383:43–49
Neri G, Arrigo I, Corigliano F, De Luca L, Donato A (2011) Selective hydrogenation of cinnamaldehyde on Pt and Pt-Fe catalysts supported on zeolite P. Catal Lett 141:1590–1597
Prakash MG, Mahalakshmy R, Krishnamurthy KR, Viswanathan B (2016) Studies on Ni–M (M= Cu, Ag, Au) bimetallic catalysts for selective hydrogenation of cinnamaldehyde. Catal Today 263:105–111
Prashar AK, Mayadevi S, Nandini Devi R (2012) Effect of particle size on selective hydrogenation of cinnamaldehyde by Pt encapsulated in mesoporous silica. Catal Commun 28:42–46
Zheng R, Porosoff MD, Weiner JL, Lu S, Zhu Y, Chen JG (2012) Controlling hydrogenation of C=O and C=C bonds in cinnamaldehyde using silica supported Co-Pt and Cu-Pt bimetallic catalysts. Appl Catal A 419–420:126–132
Lan X, Wang T, Li X, Huang N, Wang J (2016) Pt@SnOx/SiO2 catalysts with enhanced selectivity to allyl alcohol for acrolein hydrogenation. Catal Sci Technol 6:7703–7707
Lan X, Xue K, Wang T (2019) Combined synergetic and steric effects for highly selective hydrogenation of unsaturated aldehyde. J Catal 372:49–60
Guo Z, Xiao C, Maligal-Ganesh RV, Zhou L, Goh TW et al (2014) Pt nanoclusters confined within metal–organic framework cavities for chemoselective cinnamaldehyde hydrogenation. ACS Catal 4:1340–1348
Lan X, Huang N, Wang J, Wang T (2017) Geometric effect in the highly selective hydrogenation of 3-methylcrotonaldehyde over Pt@ZIF-8 core–shell catalysts. Catal Sci Technol 7:2601–2608
Zhao M, Yuan K, Wang Y, Li G, Guo J et al (2016) Metal–organic frameworks as selectivity regulators for hydrogenation reactions. Nature 539:76–80
Gallezot P, Giroir-Fendler A, Richard D (1990) Chemioselectivity in cinnamaldehyde hydrogenation induced by shape selectivity effects in Pt-Y zeolite catalysts. Catal Lett 5:169
He CT, Jiang L, Ye ZM, Krishna R, Zhong ZS et al (2015) Exceptional hydrophobicity of a large-pore metal–organic zeolite. J Am Chem Soc 137:7217–7223
Bhadra BN, Seo PW, Khan NA, Jhung SH (2016) Hydrophobic cobalt-ethylimidazolate frameworks: phase-pure syntheses and possible application in cleaning of contaminated water. Inorg Chem 55:11362–11371
Meilikhov M, Yusenko K, Esken D, Turner S, Van Tendeloo G, Fischer RA (2010) Metals@MOFs—Loading MOFs with metal nanoparticles for hybrid functions. Eur J Inorg Chem 24:3701–3714
Teranishi T, Hosoe M, Tanaka T, Miyake M (1999) Size control of monodispersed Pt nanoparticles and their 2D organization by electrophoretic deposition. J Phys Chem B 103:3818–3827
Lu G, Li S, Guo Z, Farha OK, Hauser BG et al (2012) Imparting functionality to a metal–organic framework material by controlled nanoparticle encapsulation. Nat Chem 4:310–316
Lan X, Huang N, Wang J, Wang T (2018) A general and facile strategy for precisely controlling the crystal size of monodispersed metal–organic frameworks via separating the nucleation and growth. Chem Commun 54:584–587
Chen L, Zhan W, Fang H, Cao Z, Yuan C et al (2017) Selective catalytic performances of noble metal nanoparticle@ MOF composites: the concomitant effect of aperture size and structural flexibility of MOF matrices. Chemistry 23:11397–11403
Galvagno S, Capannelli G, Neri G, Donato A, Pietropaolo R (1991) Hydrogenation of cinnamaldehyde over Ru/C catalysts: effect of Ru particle size. J Mol Catal 64:237–246
Rudolf C, Dragoi B, Ungureanu A, Chirieac A, Royer S et al (2014) NiAl and CoAl materials derived from takovite-like LDHs and related structures as efficient chemoselective hydrogenation catalysts. Catal Sci Technol 4:179–189
Zheng Q, Wang D, Yuan F, Han Q, Dong Y, Liu Y et al (2016) An Effective Co-promoted platinum of Co–Pt/SBA-15 catalyst for selective hydrogenation of cinnamaldehyde to cinnamyl alcohol. Catal Lett 146:1535–1543
Wei S, Zhao Y, Fan G, Yang L, Li F (2017) Structure-dependent selective hydrogenation of cinnamaldehyde over high-surface-area CeO2-ZrO2 composites supported Pt nanoparticles. Chem Eng J 322:234–245
Acknowledgement
This work was supported by the National Natural Science Foundation of China (no. 21676155), PetroChina Innovation Foundation (2016D-5007–0507), China Postdoctoral Science Foundation (2019M660660), and Shuimu Tsinghua Scholar program.
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Xue, K., Lan, X., Wang, J. et al. Synthesis of Pt@MAF-6 as a Steric Effect Catalyst for Selective Hydrogenation of Cinnamaldehyde. Catal Lett 150, 3234–3242 (2020). https://doi.org/10.1007/s10562-020-03212-0
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DOI: https://doi.org/10.1007/s10562-020-03212-0