Acknowledgement
Supported by : National Natural Science Foundation of China, Fujian Province, Huaqiao University
References
- F. Meemken, A. Baiker, Recent progress in heterogeneous asymmetric hydrogenation of C=O and C=C bonds on supported noble metal catalysts, Chem. Rev. 117 (2017) 11522-11569. https://doi.org/10.1021/acs.chemrev.7b00272
- Y. Orito, S. Imai, S. Niwa, Asymmetric hydrogenation of methyl pyruvate using Pt-C catalyst modified with cinchonidine, Nippon Kagaku Kaishi 8 (1979) 1118-1120.
-
X. Li, C. Li, Enantioselective hydrogenation of ethyl-2-oxo-4-phenylbutyrate on cinchonidine-modified
$Pt/{\gamma}-Al_2O_3$ catalyst using a fixed-bed reactor, Catal. Lett. 77 (2001) 251-254. https://doi.org/10.1023/A:1013280116781 -
H. An, X. Hu, W. Zhao, B. Zhu, S. Wang, Characterization of Pt catalysts supported by three forms of
$TiO_2$ and their catalytic activities for hydrogenation, React. Kinet. Mech. Catal. 108 (2013) 117-126. https://doi.org/10.1007/s11144-012-0480-y -
M.U. Azmat, Y. Guo, Y. Guo, Y. Wang, G. Lu, An easy and effective approach towards heterogeneous
$Pt/SiO_2$ -cinchonidine catalyst system for enantioselective hydrogenation of ethyl pyruvate, J. Mol. Catal. Chem. 336 (2011) 42-50. https://doi.org/10.1016/j.molcata.2010.12.008 - T.J. Hall, J.E. Halder, G.J. Hutchings, R.L. Jenkins, P. Johnston, P. Mcmorn, P.B. Wells, R.P.K. Wells, Enantioselective hydrogenation of pyruvate esters in the mesoporous environment of Pt-MCM-41, Top. Catal. 11 (2000) 351-357.
- L.L. Lou, T. Yang, W. Yu, H. Qu, Y. Feng, H. Li, K. Yu, S. Liu, Effective and durable Pt nanocatalyst supported on three-dimensionally ordered macroporous carbon for asymmetric hydrogenation, Catal. Today 298 (2017) 197-202. https://doi.org/10.1016/j.cattod.2017.04.037
- S. Basu, M. Mapa, C.S. Gopinath, M. Doble, S. Bhaduri, G.K. Lahiri, MCM-41-supported platinum carbonyl cluster-derived catalysts for asymmetric and nonasymmetric hydrogenation reactions, J. Catal. 239 (2006) 154-161. https://doi.org/10.1016/j.jcat.2006.01.032
- L. Xing, F. Du, J.J. Liang, Y.S. Chen, Q.L. Zhou, Preparation of Pt/SWNTs for heterogeneous asymmetric hydrogenation of ethyl pyruvate, J. Mol. Catal. Chem. 276 (2007) 191-196. https://doi.org/10.1016/j.molcata.2007.07.003
- Z. Chen, Z. Guan, M. Li, Q. Yang, C. Li, Enhancement of the performance of a platinum nanocatalyst confined within carbon nanotubes for asymmetric hydrogenation, Angew. Chem. Int. Ed. 123 (2011) 5015-5019. https://doi.org/10.1002/ange.201006870
- B. Li, X. Li, H. Wang, P. Wu, Pt nanoparticles entrapped in ordered mesoporous carbon for enantioselective hydrogenation, J. Mol. Catal. Chem. 345 (2011) 81-89. https://doi.org/10.1016/j.molcata.2011.05.023
-
X. Zhang, Q. Li, M. Xiao, Y. Liu, Effective one-step reduction of Pt/alumina-carbon catalysts for asymmetric hydrogenation of
$\alpha$ -ketoesters, Appl. Catal. A Gen. 480 (2014) 50-57. https://doi.org/10.1016/j.apcata.2014.04.031 - T. Yang, L.L. Lou, W. Yu, Y. Feng, H. Li, K. Yu, S. Liu, Three-dimensionally ordered macroporous alumina-carbon nanocomposite supported Pt nanoparticles as effective and reusable catalysts for asymmetric hydrogenation, ChemCatChem 9 (2017) 458-464. https://doi.org/10.1002/cctc.201601179
- Y. Ji, V. Koot, A.M.J. Van Der Eerden, B.M. Weckhuysen, D.C. Koningsberger, D.E. Ramaker, A three-site Langmuir adsorption model to elucidate the temperature, pressure, and support dependence of the hydrogen coverage on supported Pt particles, J. Catal. 245 (2007) 415-427. https://doi.org/10.1016/j.jcat.2006.10.028
-
A.Y. Stakheev, Y. Zhang, A.V. Ivanov, G.N. Baeva, A.D.E. Ramaker, D.C. Koningsberger, Separation of geometric and electronic effects of the support on the CO and
$H_2$ chemisorption Properties of supported Pt particles: The effect of ionicity in modified alumina supports, J. Phys. Chem. C 111 (2007) 3938-3948. https://doi.org/10.1021/jp0651182 - B.L. Mojet, J.T. Miller, D.E. Ramaker, D.C. Koningsberger, A new model describing the metal-support interaction in noble metal catalysts, J. Catal. 186 (1999) 373-386. https://doi.org/10.1006/jcat.1999.2568
- M.K. Oudenhuijzen, J.A. Van Bokhoven, D.C. Koningsberger, Support-induced compensation effects in H/D exchange of cyclopentane, J. Catal. 219 (2003) 134-145. https://doi.org/10.1016/S0021-9517(03)00214-8
- F. Hoxha, B. Schimmoeller, Z. Cakl, A. Urakawa, T. Mallat, S.E. Pratsinis, A. Baiker, Influence of support acid-base properties on the platinum-catalyzed enantioselective hydrogenation of activated ketones, J. Catal. 271 (2010) 115-124. https://doi.org/10.1016/j.jcat.2010.02.012
- F. Hoxha, E. Schmidt, T. Mallat, B. Schimmoeller, S.E. Pratsinis, A. Baiker, Hydrogenation of acetophenone derivatives: tuning the enantioselectivity via the metal-support interaction, J. Catal. 278 (2011) 94-101. https://doi.org/10.1016/j.jcat.2010.11.025
- M. Yan, G. Dong, F. Zhang, Y. Shi, H. Yang, L. Zheng, C. Yu, T. Bo, D. Zhao, Ordered mesoporous polymers and homologous carbon frameworks: amphiphilic surfactant templating and direct transformation, Angew. Chem. Int. Ed. 44 (2005) 7053-7059. https://doi.org/10.1002/anie.200501561
-
C.H. Campos, C.C. Torres, A. Leyton, J. Belmar, C. Mella, P. Osorio-Vargas, D. Ruiz, J.L.G. Fierro, P. Reyes, A new non-cinchona chiral modifier immobilized on
$Pt/SiO_2$ catalysts for enantioselective heterogeneous hydrogenation, Appl. Catal. A Gen. 498 (2015) 76-87. https://doi.org/10.1016/j.apcata.2015.01.048 -
H. Hamdan, M.N.M. Muhid, S. Endud, E. Listiorini, Z. Ramli,
$^{29}Si$ MAS NMR, XRD and FESEM studies of rice husk silica for the synthesis of zeolites, J. Non-Cryst. Solids 211 (1997) 126-131. https://doi.org/10.1016/S0022-3093(96)00611-4 - X. Song, Y. Ding, W. Chen, W. Dong, Y. Pei, J. Zang, L. Yan, Y. Lu, Bimetal modified ordered mesoporous carbon as a support of Rh catalyst for ethanol synthesis from syngas, Catal. Commun. 19 (2012) 100-104. https://doi.org/10.1016/j.catcom.2011.12.015
- S.M. Glasauer, Inhibition of sintering by Si during the conversion of Si-rich ferrihydrite to hematite, Clay Clay Miner. 48 (2013) 51-56.
- E. Paparazzo, M. Fanfoni, E. Severini, S. Priori, Evidence of Si-OH species at the surface of aged silica, J. Vac. Sci. Technol. 10 (1992) 2892-2896. https://doi.org/10.1116/1.577726
- E. Miloskovska, C. Friedrichs, D. Hristova-Bogaerds, O. Persenair, M. Van Duin, M.R. Hansen, G. De With, Chemical mapping of silica prepared via sol-gel reaction in rubber nanocomposites, Macromolecules 48 (2015) 1093-1103. https://doi.org/10.1021/ma5020929
-
C. Tang, J. Zhu, Q. Zhou, J. Wei, R. Zhu, H. Heit, Surface heterogeneity of
$SiO_2$ polymorphs: an XPS investigation of alpha-quartz and alpha-cristobalite, J. Phys. Chem. C 118 (2014) 26249-26257. https://doi.org/10.1021/jp509338x -
J. Gao, J. Guo, D. Liang, Z. Hou, J. Fei, X. Zheng, Production of syngas via autothermal reforming of methane in a fluidized-bed reactor over the combined
$CeO_2-ZrO_2/SiO_2$ supported Ni catalysts, Int. J. Hydrogen Energy 33 (2008) 5493-5500. https://doi.org/10.1016/j.ijhydene.2008.07.040 - S.L. Chen, P. Dong, A. Guanghua Yang, J.J. Yang, Kinetics of formation of monodisperse colloidal silica particles through the hydrolysis and condensation of tetraethylorthosilicate, Ind. Eng. Chem. Res. 35 (1996) 4487-4493. https://doi.org/10.1021/ie9602217
- T. Hiemstra, W.H. Van Riemsdijk, G.H. Bolt, Multisite proton adsorption modeling at the solid/solution interface of (hydr)oxides: a new approach : I. Model description and evaluation of intrinsic reaction constants, J. Colloid Interface Sci. 133 (1989) 105-117. https://doi.org/10.1016/0021-9797(89)90285-3
- R. Liu, Y. Shi, Y. Wan, Y. Meng, F. Zhang, D. Gu, Z. Chen, B. Tu, D. Zhao, Triconstituent co-assembly to ordered mesostructured polymer-silica and carbon-silica nanocomposites and large-pore mesoporous carbons with high surface areas, J. Am. Chem. Soc. 128 (2006) 11652-11662. https://doi.org/10.1021/ja0633518
- H. Tang, S.P. Jiang, Self-assembled Pt/mesoporous silica-carbon electrocatalysts for elevated-temperature polymer electrolyte membrane fuel cells, J. Phys. Chem. C 112 (2008) 19748-19755. https://doi.org/10.1021/jp8066662
- R. Zhong, L. Peng, F. De Clippel, C. Gommes, B. Goderis, X. Ke, G. Van Tendeloo, P.A. Jacobs, B.F. Sels, An eco-friendly soft template synthesis of mesostructured silica-carbon nanocomposites for acid catalysis, ChemCatChem 7 (2015) 3047-3058. https://doi.org/10.1002/cctc.201500728
- C.J. Brinker, Hydrolysis and condensation of silicates: effects on structure, J. Non-Cryst. Solids 100 (1988) 31-50. https://doi.org/10.1016/0022-3093(88)90005-1
- N.B. Mckeown, S. Makhseed, P.M. Budd, Phthalocyanine-based nanoporous network polymers, Chem. Commun. 23 (2002) 2780-2781.
- Z. Sun, B. Sun, M. Qiao, J. Wei, Q. Yue, C. Wang, Y. Deng, K. Serge, D. Zhao, General chelate-assisted co-assembly to metallic nanoparticles-incorporated ordered mesoporous carbon catalysts for fischerâtropsch synthesis, J. Am. Chem. Soc. 134 (2012) 17653-17660. https://doi.org/10.1021/ja306913x
-
J.T. Wehrli, A. Baiker, D.M. Monti, H.U. Blaser, Enantioselective hydrogenation of
$\alpha$ -ketoesters: preparation and catalytic behavior of different alumina-supported platinum catalysts modified with cinchonidine, J. Mol. Catal. 61 (1990) 207-226. https://doi.org/10.1016/0304-5102(90)85156-C - D.Y. Murzin, E. Toukoniitty, Nanocatalysis in asymmetric hydrogenation, React. Kinet. Catal. Lett. 90 (2007) 19-25. https://doi.org/10.1007/s11144-007-5004-9
-
B. Torok, K. Balazsik, M. Torok, G. Szollosi, M. Bartok, Asymmetric sonochemical reactions enantioselective hydrogenation of
$\alpha$ -ketoesters over platinum catalysts, Ultrason. Sonochem. 7 (2000) 151-155. https://doi.org/10.1016/S1350-4177(00)00035-3 - E. Schmidt, A. Vargas, T. Mallat, A. Baiker, Shape-selective enantioselective hydrogenation on Pt nanoparticles, J. Am. Chem. Soc. 131 (2009) 12358-12367. https://doi.org/10.1021/ja9043328
- Q. Li, X. Zhang, M. Xiao, Y. Liu, Alumina incorporated with mesoporous carbon as a novel support of Pt catalyst for asymmetric hydrogenation, Catal. Commun. 42 (2013) 68-72. https://doi.org/10.1016/j.catcom.2013.07.044
-
M. Bartok, K. Balazsik, G. Szollosi, T. Bartok, Electrospray ionization-mass spectrometry in the enantioselective hydrogenation of ethyl pyruvate catalyzed by dihydrocinchonidine modified
$Pt/Al_2O_3$ in acetic acid, J. Catal. 205 (2002) 168-176. https://doi.org/10.1006/jcat.2001.3423 - T. Tri, J. Massardier, P. Gallezot, B. Imelik, Additives and support effects on Pt catalysts studied by the competitive hydrogenation of benzene and toluene, Stud. Surf. Sci. Catal. 11 (1982) 141-148.
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