Browse > Article
http://dx.doi.org/10.1016/j.cap.2018.09.001

Carbon-silica composites supported Pt as catalyst for asymmetric hydrogenation of ethyl 2-oxo-4-phenylbutyrate  

Mao, Cong (College of Chemical Engineering, Huaqiao University)
Zhang, Jie (College of Chemical Engineering, Huaqiao University)
Xiao, Meitian (College of Chemical Engineering, Huaqiao University)
Liu, Yongjun (College of Chemical Engineering, Huaqiao University)
Zhang, Xueqin (College of Chemical Engineering, Huaqiao University)
Publication Information
Current Applied Physics / v.18, no.12, 2018 , pp. 1480-1485 More about this Journal
Abstract
Mesoporous carbon-silica composites supported Pt nanoparticle catalysts (Pt/MCS) were firstly applied to the heterogeneous asymmetric hydrogenation of ethyl 2-oxo-4-phenylbutyrate (EOPB). A series of different silica contents were investigated in the fabrication of this mesoporous material. When the volume of added tetraethyl orthosilicate (TEOS) during the preparation of composites is 8 mL, Pt/MCS-8 holds carbon and silica as the main components and possesses relatively strong acidity, mesoporous structures with micropores, appropriate Pt nanoparticle size and high dispersibility showing by XRD, XPS, TPD, $N_2$ sorption and TEM. These properties cause its good catalytic performance in the heterogeneous asymmetric hydrogenation of EOPB with the enantiomeric excess value and conversion up to 85.6% and 97.8%, respectively.
Keywords
Carbon-silica materials; Mesoporous; Pt nanoparticles; Asymmetric hydrogenation;
Citations & Related Records
연도 인용수 순위
  • Reference
1 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.   DOI
2 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.   DOI
3 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.   DOI
4 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.   DOI
5 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.   DOI
6 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.   DOI
7 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.   DOI
8 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.   DOI
9 S.M. Glasauer, Inhibition of sintering by Si during the conversion of Si-rich ferrihydrite to hematite, Clay Clay Miner. 48 (2013) 51-56.
10 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.   DOI
11 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.   DOI
12 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.   DOI
13 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.   DOI
14 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.   DOI
15 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.   DOI
16 C.J. Brinker, Hydrolysis and condensation of silicates: effects on structure, J. Non-Cryst. Solids 100 (1988) 31-50.   DOI
17 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.   DOI
18 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.   DOI
19 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.   DOI
20 N.B. Mckeown, S. Makhseed, P.M. Budd, Phthalocyanine-based nanoporous network polymers, Chem. Commun. 23 (2002) 2780-2781.
21 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.   DOI
22 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.   DOI
23 D.Y. Murzin, E. Toukoniitty, Nanocatalysis in asymmetric hydrogenation, React. Kinet. Catal. Lett. 90 (2007) 19-25.   DOI
24 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.
25 E. Schmidt, A. Vargas, T. Mallat, A. Baiker, Shape-selective enantioselective hydrogenation on Pt nanoparticles, J. Am. Chem. Soc. 131 (2009) 12358-12367.   DOI
26 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.   DOI
27 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.   DOI
28 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.   DOI
29 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.   DOI
30 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.   DOI
31 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.   DOI
32 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.
33 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.   DOI
34 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.   DOI
35 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.   DOI
36 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.   DOI
37 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.   DOI
38 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.   DOI
39 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.   DOI
40 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.   DOI
41 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.   DOI
42 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.   DOI
43 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.