High enantioselectivity in the asymmetric hydrogenation of ketones by a supported Pt nanocatalyst on a mesoporous modified MCM-41 support

doi:10.1016/S1872-2067(14)60279-5

Abstract

Abstract:

Catalysts containing metal nanotubes were prepared by the adsorption of platinum metal nanotubes onto functionalized and modified silica surfaces (MCM-41 and fumed silica). (3- Chloropropyl)trimethoxysilane and cinchonidine were used for functionalization and modification, respectively. Potassium chloroplatinate was used as the metal precursor to impregnate platinum metal nanotubes on the pretreated functionalized and modified silica surfaces. The solid catalysts were characterized by ESEM, TEM, EDAX, and XPS. The MCM-41 supported platinum nanotube catalyst showed >98% to ~100% enantioselectivity towards the hydrogenation of a range of pharmaceutically important chemicals such as methyl pyruvate, ethyl pyruvate, and acetophenone with nearly full conversion.

Key words: MCM-41, Platinum nanotube, Functionalized silica, Chiral modifier, Enantioselective hydrogenation

Susmit Basu. High enantioselectivity in the asymmetric hydrogenation of ketones by a supported Pt nanocatalyst on a mesoporous modified MCM-41 support[J]. Chinese Journal of Catalysis, 2015, 36(4): 634-638.

×
share this article

Add to citation manager EndNote|Ris|BibTeX

URL: https://www.cjcatal.com/EN/10.1016/S1872-2067(14)60279-5

https://www.cjcatal.com/EN/Y2015/V36/I4/634

References

[1] Iijima S. Nature, 1991, 354: 56
[2] Che G L, Lakshmi B B, Martin C R, Fisher E R. Langmuir, 1999, 15: 750
[3] Li Y D, Chen J L, Ma Y M, Zhao J B, Qin Y N, Chang L. Chem Commun, 1999: 1141
[4] Zhang Y, Zhang H B, Lin G D, Chen P, Yuan Y Z, Tsai K R. Appl Catal A, 1999, 187: 213
[5] De Jong K P, Geus J W. Catal Rev-Sci Eng, 2000, 42: 481
[6] Joo S H, Choi S J, Oh I, Kwak J, Liu Z, Terasaki O, Ryoo R. Nature, 2001, 412: 169
[7] Oshima Y, Koizumi H, Mouri K, Hirayama H, Takayanagi K, Kondo Y. Phys Rev B, 2002, 65: 121401
[8] Pawelec B, La Parola V, Navarro R M, Murcia-Mascaros S, Fierro J L G. Carbon, 2006, 44: 84
[9] Corma A, Garcia H. Top Catal, 2008, 48: 8
[10] Baglio V, Di Blasi A, D'Urso C, Antonucci V, Arico A S, Ornelas R, Morales-Acosta D, Ledesma-Garcia J, Godinez L A, Arriaga L G, Alvarez-Contreras L. J Electrochem Soc, 2008, 155: B829
[11] Tu W W, Lei J P, Ju H X. Electrochem Commun, 2008, 10: 766
[12] Nath D, Banerjee P. Environ Toxicol Pharmacol, 2013, 36: 997
[13] Jiao Q Z, Hao L, Shao Q Y, Zhao Y. Carbon, 2013, 61: 647
[14] Mubarak N M, Abdullah E C, Jayakumar N S, Sahu J N. J Ind Eng Chem, 2014, 20: 1186
[15] Conley M P, Coperet C, Thieuleux C. ACS Catal, 2014, 4: 1458
[16] Zhou H J, Zou F M, Koh K, Lee J. J Biomed Nanotechnol, 2014, 10: 2921
[17] Tang Q, Zhang Q E, Jiang Y, Li J S, Zheng J, Li Y H, Yang R H, Tan W H. ACS Appl Mater Interf, 2014, 6: 13470
[18] Bousslama W, Sieber B, Elhouichet H, Gelloz B, Addad A, Ferid M. J Phys D, 2013, 46: 505104
[19] Von Bargen C D, MacDermaid C M, Lee O S, Deria P, Therien M J, Saven J G. J Phys Chem B, 2013, 117: 12953
[20] Miller J. Phys Today, 2012, 65(6): 22
[21] Lee S H, Sung J H, Park T H. Ann Biomed Eng, 2012, 40: 1384
[22] Panthani M G, Korgel B A. Annu Rev Chem Biomol Eng, 2012, 3: 287
[23] Kameta N, Masuda M, Shimizu T. Kobunshi Ronbunshu, 2010, 67: 560
[24] Chakoli A N, Wan J, Feng J T, Amirian M, Sui J H, Cai W. Appl Surf Sci, 2009, 256: 170
[25] Hochbaum A I, Fan R, He R R, Yang P D. Nano Lett, 2005, 5: 457
[26] Shin J C, Kim D Y, Lee A, Kim H J, Kim J H, Choi W J, Kim H S, Choi K J. J Cryst Growth, 2013, 372: 15
[27] Togonal A S, He L N, Cabarrocas P R I, Rusli. Langmuir, 2014, 30: 10290
[28] Kato S, Kurokawa Y, Miyajima S, Watanabe Y, Yamada A, Ohta Y, Niwa Y, Hirota M. Nanoscale Res Lett, 2013, 8: 361
[29] Basu S, Mapa M, Gopinath C S, Doble M, Bhaduri S, Lahiri G K. J Catal, 2006, 239: 154
[30] Izumi Y, Konishi K, Tsukahara M, Obaid D M, Aika K I. J Phys Chem C, 2007, 111: 10073
[31] Barbaro P, Bianchini C, Dal Santo V, Meli A, Moneti S, Pirovano C, Psaro R, Sordelli L, Vizza F. Organometallics, 2008, 27: 2809
[32] Beckers N A, Huynh S, Zhang X J, Luber E J, Buriak J M. ACS Catal, 2012, 2: 1524
[33] Kung H H, Kung M C. Catal Lett, 2014, 144: 1643
[34] Chaplin A B, Dyson P J. J Organomet Chem, 2011, 696: 2485
[35] Dal Santo V, Liguori F, Pirovano C, Guidotti M. Molecules, 2010, 15: 3829
[36] Wagner H H, Hausmann H, Hölderich W F. J Catal, 2001, 203: 150
[37] Crosman A, Hölderich W F. J Catal, 2005, 232: 43
[38] Böttcher S, Hoffmann C, Räuchle K, Reschetilowski W. ChemCatChem, 2011, 3: 741
[39] Indra A, Doble M, Bhaduri S, Lahiri G K. ACS Catal, 2011, 1: 511
[40] Török B, Balázsik K, Török M, Szöllösi G, Bartók M. Ultrason Sonochem, 2000, 7: 151
[41] Bartók M, Balázsik K, Szöllösi G, Bartók T. J Catal, 2002, 205: 168
[42] Schmidt E, Vargas A, Mallat T, Baiker A. J Am Chem Soc, 2009, 131: 12358
[43] Schmidt E, Hoxha F, Mallat T, Baiker A. J Catal, 2010, 274: 117
[44] Hoxha F, Schimmoeller B, Cakl Z, Urakawa A, Mallat T, Pratsinis S E, Baiker A. J Catal, 2010, 271: 115
[45] Beck J S, Vartuli J C, Roth W J, Leonowicz M E, Kresge C T, Schmitt K D, Chu C T W, Olson D H, Sheppard E W, McCullen S B, Higgins J B, Schlenker J L. J Am Chem Soc, 1992, 114: 10834
[46] Jyothi T M, Kaliya M L, Herskowitz M, Landau M V. Chem Commun, 2001: 992
[47] Mokaya R. Chem Commun, 2001: 1092
[48] Basu S, Paul H, Gopinath C S, Bhaduri S, Lahiri G K. J Catal, 2005, 229: 298
[49] Apai G, Lee S T, Mason M G, Gerenser L J, Gardner S A. J Am Chem Soc, 1979, 101: 6880