Asymmetric Hydrogenation of Ethyl Pyruvate on Chirally Modified Pt Catalysts Supported on Al2O3@FDU-14 Mesoporous Composites

doi:10.1016/S1872-2067(10)60274-4

Abstract

Abstract: A series of Al₂O₃@FDU-14 composites with different alumina loadings were prepared using a solid state grinding method. The 4% Pt catalysts supported on Al₂O₃@FDU-14 were prepared by impregnation using H₂PtCl₆. X-ray diffraction, transmission electron microscopy, and nitrogen adsorption characterization of the Pt/Al₂O₃@FDU-14 catalysts indicated that the mesoporous features of the FDU-14 mesopolymer were retained. The Pt/Al₂O₃@FDU-14 catalysts were used in the asymmetric hydrogenation of ethyl pyruvate after they were chirally modified with cinchonidine. For Al₂O₃ loading from 5% to 15%, Al₂O₃ was uniformly dispersed inside the mesoporous channels of FDU-14 host. Ethyl pyruvate conversion and their ee values increased with increasing alumina loading, with a highest ee value of 80%. It was suggested that the alumina coating inside the mesoporous channels of FDU-14 decreased the surface electronic density of the FDU-14 mesopolymer so that cinchonidine can be easily adsorbed on the surface of Pt/Al₂O₃@FDU-14 catalysts. As compared with chirally modified Pt/FDU-14 catalysts, chirally modified Pt/Al₂O₃@FDU-14 catalysts gave higher ee values.

Key words: platinum, cinchonidine, ethyl pyruvate, asymmetric hydrogenation, periodic mesoporous resol, mesoporous alumina composite

WANG Hai-Hong, WANG Hong-Na, LI Xiao-Hong, WANG Yi-Meng, WU Peng. Asymmetric Hydrogenation of Ethyl Pyruvate on Chirally Modified Pt Catalysts Supported on Al2O3@FDU-14 Mesoporous Composites[J]. Chinese Journal of Catalysis, 2011, 32(11): 1677-1684.

×
share this article

Add to citation manager EndNote|Ris|BibTeX

URL: https://www.cjcatal.com/EN/10.1016/S1872-2067(10)60274-4

https://www.cjcatal.com/EN/Y2011/V32/I11/1677

References

1Mallat T, Orglmeister E, Baiker A. Chem Rev, 2007, 107: 4863
2Wehrli J T, Baiker A, Monti D M, Blaser H U. J Mol Catal, 1990, 61: 207
3Blaser H U, Jalett H P, Müller M, Studer M. Catal Today, 1997, 37: 441
4Zuo X B, Liu H F, Yue Ch. J Mol Catal A, 1999, 147: 63
5Török B, Felföldi K, Balázsik K, Bartók M. Chem Commun, 1999: 1725
6Bhaduri S, Lahiri G K, Munshi P, Munshi P, Mukesh D. Catal Lett, 2000, 65: 61
7Studer M, Blaser H U, Exner C. Adv Syn Catal, 2003, 345: 45
8Bürgi T, Baiker A. Acc Chem Res, 2004, 37: 909
9Balázsik K, Bartok M. J Mol Catal A, 2004, 219: 383
10姜鹏, 李晓红, 关业军, 应品良, 李灿. 分子催化 (Jiang P, Li X H, Guan Y J, Ying P L, Li C. J Mol Catal (China)), 2004, 18: 381
11Bartok M. Curr Org Chem, 2006, 10: 1533
12Balázsik K, Szöri K, Felföldi K, Török B, Bartók M. Chem Commun, 2000: 555
13韩涤非, 杨启华, 李灿. 催化学报 (Han D F, Yang Q H, Li C. Chin J Catal), 2008, 29: 789
14Balázsik K, Szöri K, Szöllösi G, Bartók M. Chem Commun, 2011, 47: 1551
15Tálas E, Margitfalvi J L, Egyed O. J Catal, 2009, 266: 191
16Török B, Szöllösi G, Balázsik K, Felföldi K, Kun I, Bartók M. Ultrasonics Sonochem, 1999, 6: 97
17Griffiths S P, Johnson P, Wells P B. Appl Catal A, 2000, 191: 193
18陈志坚, 李晓红, 李灿. 催化学报 (Chen Zh J, Li X H, Li C. Chin J Catal), 2011, 32: 155
19Wang H N, Li X H, Wang Y M, Wu P. ChemCatChem, 2010, 2: 1303
20Li X H, Shen Y L, Xing R, Liu Y M, Wu H H, He M Y, Wu P. Catal Lett, 2008, 122: 325
21沈亚丽, 李晓红, 宋丽英, 王红娜, 吴鹏. 高等学校化学学报 (Shen Y L, Li X H, Song L Y, Wang H N, Wu P. Chem J Chin Univ), 2009, 30: 1375
22Chen Z J, Guan Z H, Li M R, Yang Q H, Li C. Angew Chem, Int Ed, 2011, 50: 4913
23Xing L, Du F, Liang J J, Chen Y S, Zhou Q L. J Mol Catal A, 2007, 276: 191
24Li B, Li X H, Wang H N, Wu P. J Mol Catal A, 2011, 345: 81
25陶国忠, 卢冠忠, 郭耘, 王艳芹, 郭杨龙, 张志刚, 刘晓晖, 王筠松. 催化学报 (Tao G Z, Lu G Z, Guo Y, Wang Y Q, Guo Y L, Zhang Zh G, Liu X H, Wang Y S. Chin J Catal), 2009, 30: 391
26彭宗海, 马梦林, 付海燕, 陈华, 李贤钧. 催化学报 (Peng Z H, Ma M L, Fu H Y, Chen H, Li X J. Chin J Catal), 2010, 31: 191
27Zhang F Q, Meng Y, Gu D, Yan Y, Yu Ch Zh, Tu B, Zhao D Y. J Am Chem Soc, 2005, 127: 13508
28Zhang F Q, Meng Y, Gu D, Yan Y, Chen Zh X, Tu B, Zhao D Y. Chem Mater, 2006, 18: 5279
29Wang Y M, Wu Zh Y, Shi L Y, Zhu J H. Adv Mater, 2005, 17: 323

[1]	Yujie Li, Yuanyuan Liu, Zeyan Wang, Peng Wang, Zhaoke Zheng, Hefeng Cheng, Ying Dai, Baibiao Huang. Enhanced photocatalytic H2O2 production over Pt(II) deposited boron containing metal-organic framework via suppressing the simultaneous decomposition [J]. Chinese Journal of Catalysis, 2023, 45(2): 132-140.
[2]	Qing Yao, Jiabo Le, Shize Yang, Jun Cheng, Qi Shao, Xiaoqing Huang. A trace of Pt can significantly boost RuO₂ for acidic water splitting [J]. Chinese Journal of Catalysis, 2022, 43(6): 1493-1501.
[3]	Lili Zhang, Suyu Jiang, Wei Ma, Zhen Zhou. Oxygen reduction reaction on Pt-based electrocatalysts: Four-electron vs. two-electron pathway [J]. Chinese Journal of Catalysis, 2022, 43(6): 1433-1443.
[4]	Wei Xiong, Min Zhou, Hao Li, Zhao Ding, Da Zhang, Yaokang Lv. Electrocatalytic ammonia synthesis catalyzed by mesoporous nickel oxide nanosheets loaded with Pt nanoparticles [J]. Chinese Journal of Catalysis, 2022, 43(5): 1371-1378.
[5]	Francisco J. Sarabia, Víctor Climent, Juan M. Feliu. Effect of the interfacial electric field on the HER on Pt(111) modified with iron adatoms in alkaline media [J]. Chinese Journal of Catalysis, 2022, 43(11): 2826-2836.
[6]	Shipeng Tang, Yang Xia, Jiajie Fan, Bei Cheng, Jiaguo Yu, Wingkei Ho. Enhanced photocatalytic H₂ production performance of CdS hollow spheres using C and Pt as bi-cocatalysts [J]. Chinese Journal of Catalysis, 2021, 42(5): 743-752.
[7]	Hee Jin Kim, Yong-Deok Ahn, Jeonghyeon Kim, Kyoung-Su Kim, Yeon Uk Jeong, Jong Wook Hong, Sang-Il Choi. Surface elemental distribution effect of Pt-Pb hexagonal nanoplates for electrocatalytic methanol oxidation reaction [J]. Chinese Journal of Catalysis, 2020, 41(5): 813-819.
[8]	Hongling Guan, Yang Chen, Chongyan Ruan, Jian Lin, Yang Su, Xiaodong Wang, Lingbo Qu. Versatile application of wet-oxidation for ambient CO abatement over Fe(OH)_x supported subnanometer platinum group metal catalysts [J]. Chinese Journal of Catalysis, 2020, 41(4): 613-621.
[9]	Zhonghai Ji, Dengyun Miao, Lijun Gao, Xiulian Pan, Xinhe Bao. Effect of pH on the catalytic performance of PtSn/B-ZrO₂ in propane dehydrogenation [J]. Chinese Journal of Catalysis, 2020, 41(4): 719-729.
[10]	Xiaoying Sun, Meijun Liu, Yaoyao Huang, Bo Li, Zhen Zhao. Electronic interaction between single Pt atom and vacancies on boron nitride nanosheets and its influence on the catalytic performance in the direct dehydrogenation of propane [J]. Chinese Journal of Catalysis, 2019, 40(6): 819-825.
[11]	Sheng Zhang, Hai Liu, Na Zhang, Rong Xia, Siyu Kuang, Geping Yin, Xinbin Ma. Tuning the electronic structure of platinum nanocrystals towards high efficient ethanol oxidation [J]. Chinese Journal of Catalysis, 2019, 40(12): 1904-1911.
[12]	Shelly Kelly, Wharton Sinkler, Lijun Xu, Sergio Sanchez, Cem Akatay, Haiyan Wang, John Qianjun Chen. Advanced characterization for industrial catalysis applications [J]. Chinese Journal of Catalysis, 2019, 40(11): 1637-1654.
[13]	Yan Wan, Congcong Zheng, Xianchi Lei, Mengqi Zhuang, Jinhan Lin, Wenda Hu, Jingdong Lin, Shaolong Wan, Yong Wang. Oxidative esterification of acetol with methanol to methyl pyruvate over hydroxyapatite supported gold catalyst: Essential roles of acid-base properties [J]. Chinese Journal of Catalysis, 2019, 40(11): 1810-1819.
[14]	Lin Tao, Chunzhi Li, Yiqi Ren, He Li, Jian Chen, Qihua Yang. Synthesis of polymer/CNTs composites for the heterogeneous asymmetric hydrogenation of quinolines [J]. Chinese Journal of Catalysis, 2019, 40(10): 1548-1556.
[15]	Huimin Yang, Baiyan Zhang, Bin Zhang, Zhe Gao, Yong Qin. N-doped carbon modified Pt/CNTs synthesized by atomic layer deposition with enhanced activity and stability for methanol electrooxidation [J]. Chinese Journal of Catalysis, 2018, 39(6): 1038-1043.