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

다국어 초록 (Multilingual 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, N2 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.

참고문헌 (Reference)

1 R. Liu, "Triconstituent co-assembly to ordered mesostructured polymer-silica and carbonsilica nanocomposites and large-pore mesoporous carbons with high surface areas" 128 : 11652-11662, 2006

2 T. Yang, "Three-dimensionally ordered macroporous alumina-carbon nanocomposite supported Pt nanoparticles as effective and reusable catalysts for asymmetric hydrogenation" 9 : 458-464, 2017

3 C. Tang, "Surface heterogeneity of SiO2polymorphs: an XPS investigation of alpha-quartz and alpha-cristobalite" 118 : 26249-26257, 2014

4 M. K. Oudenhuijzen, "Support-induced compensation effects in H/D exchange of cyclopentane" 219 : 134-145, 2003

5 E. Schmidt, "Shape-selective enantioselective hydrogenation on Pt nanoparticles" 131 : 12358-12367, 2009

6 A. Y. Stakheev, "Separation of geometric and electronic effects of the support on the CO and H2 chemisorption Properties of supported Pt particles: The effect of ionicity in modified alumina supports" 111 : 3938-3948, 2007

7 H. Tang, "Self-assembled Pt/mesoporous silica-carbon electrocatalysts for elevated-temperature polymer electrolyte membrane fuel cells" 112 : 19748-19755, 2008

8 F. Meemken, "Recent progress in heterogeneous asymmetric hydrogenation of C═O and C═C bonds on supported noble metal catalysts" 117 : 11522-11569, 2017

9 B. Li, "Pt nanoparticles entrapped in ordered mesoporous carbon for enantioselective hydrogenation" 345 : 81-89, 2011

10 J. Gao, "Production of syngas via autothermal reforming of methane in a fluidized-bed reactor over the combined CeO2-ZrO2/SiO2 supported Ni catalysts" 33 : 5493-5500, 2008

11 L. Xing, "Preparation of Pt/SWNTs for heterogeneous asymmetric hydrogenation of ethyl pyruvate" 276 : 191-196, 2007

12 N. B. Mckeown, "Phthalocyanine-based nanoporous network polymers" 23 : 2780-2781, 2002

13 M. Yan, "Ordered mesoporous polymers and homologous carbon frameworks: amphiphilic surfactant templating and direct transformation" 44 : 7053-7059, 2005

14 D. Y. Murzin, "Nanocatalysis in asymmetric hydrogenation" 90 : 19-25, 2007

15 T. Hiemstra, "Multisite proton adsorption modeling at the solid/solution interface of (hydr)oxides: a new approach : I. Model description and evaluation of intrinsic reaction constants" 133 : 105-117, 1989

16 S. Basu, "MCM-41-supported platinum carbonyl cluster-derived catalysts for asymmetric and nonasymmetric hydrogenation reactions" 239 : 154-161, 2006

17 S. L. Chen, "Kinetics of formation of monodisperse colloidal silica particles through the hydrolysis and condensation of tetraethylorthosilicate" 35 : 4487-4493, 1996

18 S. M. Glasauer, "Inhibition of sintering by Si during the conversion of Si-rich ferrihydrite to hematite" 48 : 51-56, 2013

19 F. Hoxha, "Influence of support acid-base properties on the platinum-catalyzed enantioselective hydrogenation of activated ketones" 271 : 115-124, 2010

20 C. J. Brinker, "Hydrolysis and condensation of silicates: effects on structure" 100 : 31-50, 1988

21 F. Hoxha, "Hydrogenation of acetophenone derivatives: tuning the enantioselectivity via the metal-support interaction" 278 : 94-101, 2011

22 Z. Sun, "General chelate-assisted co-assembly to metallic nanoparticles-incorporated ordered mesoporous carbon catalysts for fischerâtropsch synthesis" 134 : 17653-17660, 2012

23 E. Paparazzo, "Evidence of Si-OH species at the surface of aged silica" 10 : 2892-2896, 1992

24 Z. Chen, "Enhancement of the performance of a platinum nanocatalyst confined within carbon nanotubes for asymmetric hydrogenation" 123 : 5015-5019, 2011

25 J. T. Wehrli, "Enantioselective hydrogenation of α-ketoesters: preparation and catalytic behavior of different alumina-supported platinum catalysts modified with cinchonidine" 61 : 207-226, 1990

26 T. J. Hall, "Enantioselective hydrogenation of pyruvate esters in the mesoporous environment of Pt-MCM-41" 11 : 351-357, 2000

27 X. Li, "Enantioselective hydrogenation of ethyl-2-oxo-4-phenylbutyrate on cinchonidine-modified Pt/γ-Al2O3 catalyst using a fixed-bed reactor" 77 : 251-254, 2001

28 M. Bartók, "Electrospray ionization-mass spectrometry in the enantioselective hydrogenation of ethyl pyruvate catalyzed by dihydrocinchonidine modified Pt/Al2O3 in acetic acid" 205 : 168-176, 2002

29 X. Zhang, "Effective one-step reduction of Pt/alumina-carbon catalysts for asymmetric hydrogenation of α-ketoesters" 480 : 50-57, 2014

30 L. L. Lou, "Effective and durable Pt nanocatalyst supported on three-dimensionally ordered macroporous carbon for asymmetric hydrogenation" 298 : 197-202, 2017

31 E. Miloskovska, "Chemical mapping of silica prepared via sol-gel reaction in rubber nanocomposites" 48 : 1093-1103, 2015

32 H. An, "Characterization of Pt catalysts supported by three forms of TiO2 and their catalytic activities for hydrogenation" 108 : 117-126, 2013

33 X. Song, "Bimetal modified ordered mesoporous carbon as a support of Rh catalyst for ethanol synthesis from syngas" 19 : 100-104, 2012

34 B. Török, "Asymmetric sonochemical reactions enantioselective hydrogenation of α-ketoesters over platinum catalysts" 7 : 151-155, 2000

35 Y. Orito, "Asymmetric hydrogenation of methyl pyruvate using Pt-C catalyst modified with cinchonidine" 8 : 1118-1120, 1979

36 R. Zhong, "An eco-friendly soft template synthesis of mesostructured silica-carbon nanocomposites for acid catalysis" 7 : 3047-3058, 2015

37 M. U. Azmat, "An easy and effective approach towards heterogeneous Pt/SiO2-cinchonidine catalyst system for enantioselective hydrogenation of ethyl pyruvate" 336 : 42-50, 2011

38 Q. Li, "Alumina incorporated with mesoporous carbon as a novel support of Pt catalyst for asymmetric hydrogenation" 42 : 68-72, 2013

39 T. Tri, "Additives and support effects on Pt catalysts studied by the competitive hydrogenation of benzene and toluene" 11 : 141-148, 1982

40 Y. Ji, "A three-site Langmuir adsorption model to elucidate the temperature, pressure, and support dependence of the hydrogen coverage on supported Pt particles" 245 : 415-427, 2007

41 C. H. Campos, "A new non-cinchona chiral modifier immobilized on Pt/SiO2catalysts for enantioselective heterogeneous hydrogenation" 498 : 76-87, 2015

42 B. L. Mojet, "A new model describing the metal-support interaction in noble metal catalysts" 186 : 373-386, 1999

43 H. Hamdan, "29Si MAS NMR, XRD and FESEM studies of rice husk silica for the synthesis of zeolites" 211 : 126-131, 1997