Study on the Selective Hydrogenation of Quinoline Catalyzed by Composites of Metal-Organic Framework and Pt Nanoparticles※

doi:10.6023/A21120601

Acta Chimica Sinica ›› 2022, Vol. 80 ›› Issue (4): 467-475.DOI: 10.6023/A21120601 Previous Articles Next Articles

Special Issue: 中国科学院青年创新促进会合辑

Article

金属有机框架与Pt粒子复合材料催化喹啉选择性加氢性能研究^※

陈俊敏^a^,^b, 崔承前^b^,^c, 刘瀚林^b^,^c, 李国栋^a^,^b^,^c^,^*()

a 郑州大学化学学院郑州 450001
b 国家纳米科学中心中国科学院纳米系统与多级次制造重点实验室纳米科学卓越创新中心北京 100190
c 中国科学院大学纳米科学与技术学院北京 100049

投稿日期:2021-12-30 发布日期:2022-04-28
通讯作者: 李国栋
作者简介:
^※ 庆祝中国科学院青年创新促进会十年华诞.
† 共同第一作者
基金资助:
国家重点研发计划(2021YFA1500403); 中国科学院战略性先导科技专项B类研发(XDB36000000); 国家自然科学基金(22173024); 国家自然科学基金(21722102); 国家自然科学基金(51672053)

Study on the Selective Hydrogenation of Quinoline Catalyzed by Composites of Metal-Organic Framework and Pt Nanoparticles^※

Junmin Chen^a^,^b, Chengqian Cui^b^,^c, Hanlin Liu^b^,^c, Guodong Li^a^,^b^,^c()

a College of Chemistry, Zhengzhou University, Zhengzhou 450001
b Chinese Academy of Sciences Key Laboratory of Nanosystem and Hierarchical Fabrication, Chinese Academy of Sciences Center for Excellence in Nanoscience, National Center for Nanoscience and Technology, Beijing 100190
c School of Nanoscience and Technology, University of Chinese Academy of Sciences, Beijing 100049

Received:2021-12-30 Published:2022-04-28
Contact: Guodong Li
About author:
^※ Dedicated to the 10th anniversary of the Youth Innovation Promotion Association, CAS.
† These authors contributed equally to this work.
Supported by:
National Key Research & Development Program of China(2021YFA1500403); Strategic Priority Research Program of Chinese Academy of Sciences(XDB36000000); National Natural Science Foundation of China(22173024); National Natural Science Foundation of China(21722102); National Natural Science Foundation of China(51672053)

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Abstract

Selective hydrogenation of quinoline toward 1,2,3,4-tetrahydroquinoline shows great application potential in the production of medicine, pesticides and fine chemicals. However, the hydrogenation of quinoline is usually carried out under harsh reaction conditions such as high temperature and high pressure, and thus, it is a great challenge to achieve selective hydrogenation of quinoline under mild conditions. In this work, we construct platinum nanoparticles (Pt NPs) sandwiched in an inner core and an outer shell composed of a metal-organic framework synthesized by zirconium chloride and 2,2'-bipyridine-5,5'-dicarboxylic acid (known as UiO-67N). Different sandwich structures with shell thickness of 11, 28 and 42 nm are precisely prepared. The obtained catalysts were characterized by X-ray diffraction (XRD), scanning electron microscopy (SEM), transmission electron microscopy (TEM), X-ray photoelectron spectroscopy (XPS), inductively coupled plasma emission spectrometer (ICP-OES), Fourier transform infrared spectroscopy (FTIR) and nitrogen adsorption and desorption. Impressively, the selective hydrogenation of quinoline over Pt NPs is significantly enhanced by using UiO-67N as support in respect with UiO-67. Moreover, UiO-67N@Pt@UiO-67N exhibits the selective hydrogenation of quinoline with high conversion rate (>99%) and high selectivity of 1,2,3,4-tetrahydroisoquinoline (>99%) at room temperature. The shell thickness has significant influence on the catalytic activity of Pt NPs, and with increasing the shell thickness from 11 to 42 nm, the conversion rate decreases from 99% to 53.5% under the identical conditions, while the selectivity of 1,2,3,4-tetrahydroisoquinoline is well kept. When other derivatives of quinoline are used as substrates, the excellent activity and selectivity are also achieved over sandwich catalysts. Besides, the UiO-67N@Pt@UiO-67N catalyst could be used at least 5 times without obvious deactivation, but the significant deactivation happens over supported UiO-67N@Pt catalyst. XPS and FTIR measurements show that the excellent catalytic performance mainly originates from the electron transfer between UiO-67N and Pt NPs, and the strong interfacial interaction between UiO-67N and quinoline.

Key words: metal-organic framework, Pt nanoparticles, sandwich structure, electron transfer, hydrogenation of quinoline

Cite this article

Junmin Chen, Chengqian Cui, Hanlin Liu, Guodong Li. Study on the Selective Hydrogenation of Quinoline Catalyzed by Composites of Metal-Organic Framework and Pt Nanoparticles^※[J]. Acta Chimica Sinica, 2022, 80(4): 467-475.

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Fig. & Tab. 7

Figure 1. Scheme of synthesis of UiO-67N@Pt@UiO-67N

Figure 2. (a) and (b) TEM images of UiO-67N@Pt@UiO-67N(11). (c) High resolution image of Pt NPs. (d) Corresponding size histogram of the exterior shell thickness. (e) Element distribution images of UiO-67N@Pt@UiO-67N(11)

Figure 3. (a) XRD patterns of UiO-67N, UiO-67N@Pt and UiO-67N@Pt@UiO-67N(11). (b) N2 adsorption and desorption curves of UiO-67N, UiO-67N@Pt and UiO-67N@Pt@UiO-67N(11). Inset is pore-size distribution curves

Figure 4. XPS spectra of catalysts: (a) Pt 4f spectra of Pt NPs and UiO-67N@Pt. (b) N 1s spectra of UiO-67N and UiO-67N@Pt

No.	Catalyst	T/℃	t/h		Sel. of B^b/%	TOF^c/h^–1
1	UiO-67N@Pt@UiO-67N(11)	30	2.83	>99.0	>99	88.3
2	UiO-67N@Pt	30	2.50	>99.0	>99	100.0
3	UiO-67@Pt	30	2.50	72.0	>99	72.0
4	SiO₂@Pt	30	2.50	32.0	>99	32.0
5	UiO-67N@Pt@UiO-67N(28)	30	2.83	63.0	>99	55.7
6	UiO-67N@Pt@UiO-67N(42)	30	2.83	53.5	>99	47.3
7	Pt@UiO-67N	30	2.83	28.6	>99	25.3

Table 1. Selective hydrogenation of quinoline catalyzed by various catalysts

Figure 5. (a) Cyclic performance of selective hydrogenation of quinoline over UiO-67N@Pt catalyst. (b) and (c) TEM images of UiO-67N@Pt catalyst before and after the fifth cycle. (d) Cyclic performance of selective hydrogenation of quinoline over UiO-67N@Pt@UiO-67N(11) catalyst. (e) and (f) TEM images of UiO-67N@Pt@UiO-67N(11) catalyst before and after the fifth cycle

No.	t/h	Conv. ^b/%	Sel.^b/%	TOF^c/h^–1
1	2.83	>99	97.9	86.5
2	2.83	>99	98.1	86.7
3	2.83	97	98	83.9
4	5	97	93	45.1
5	2.83	>99	>99	88.3
6	5	97	99	48.5

Table 2. Performances of catalytic selective hydrogenation of quinoline derivatives by UiO-67N@Pt@UiO-67N(11)

References 49

[1]	Muthukrishnan, I.; Sridharan, V.; Carlos Menendez, J. Chem. Rev. 2019, 119, 5057. doi: 10.1021/acs.chemrev.8b00567 pmid: 30963764
[2]	Yadav, P.; Kumar, A.; Althagafi, I.; Nemaysh, V.; Rai, R.; Pratap, R. Curr. Top. Med. Chem. 2021, 21, 1587. doi: 10.2174/1568026621666210526164208
[3]	Cai, X.; Xie, B. Chem. Bull. 2012, 75, 7. (in Chinese)
	(蔡小华, 谢兵, 化学通报, 2012, 75, 7.)
[4]	Chen, R.; Yang, X.; Tian, H.; Wang, X.; Hagfeldt, A.; Sun, L. Chem. Mater. 2007, 19, 4007. doi: 10.1021/cm070617g
[5]	Li, C.; Ma, Y.; Liu, H.; Tao, L.; Ren, Y.; Chen, X.; Li, H.; Yang, Q. Chin. J. Catal. 2020, 41, 1288. doi: 10.1016/S1872-2067(20)63572-0
[6]	Guo, H.; Zhuang, Y.; Wang, Y.; Cao, J.; Guo, X.; Zhang, G. Chem. Ind. Eng. Prog. 2012, 31, 2288. (in Chinese)
	(郭辉, 庄玉伟, 王颖, 曹健, 郭晓战, 张国宝, 化工进展, 2012, 31, 2288.)
[7]	Rosales, M.; Jhonatan Bastidas, L.; Gonzalez, B.; Vallejo, R.; Baricelli, P. J. Catal. Lett. 2011, 141, 1305. doi: 10.1007/s10562-011-0641-z
[8]	Sun, S.; Nagorny, P. Chem. Commun. 2020, 56, 8432. doi: 10.1039/D0CC03088K
[9]	Rosales, M.; Castillo, S.; Gonzalez, A.; Gonzalez, L.; Molina, K.; Navarro, J.; Pacheco, I.; Perez, H. Transit. Metal Chem. 2004, 29, 221. doi: 10.1023/B:TMCH.0000019452.37770.e4
[10]	Wang, T.; Zhuo, L.-G.; Li, Z.; Chen, F.; Ding, Z.; He, Y.; Fan, Q.-H.; Xiang, J.; Yu, Z.-X.; Chan, A. S. C. J. Am. Chem. Soc. 2011, 133, 9878. doi: 10.1021/ja2023042
[11]	Gong, Y.; Zhang, P.; Xu, X.; Li, Y.; Li, H.; Wang, Y. J. Catal. 2013, 297, 272. doi: 10.1016/j.jcat.2012.10.018
[12]	Zhang, F.; Ma, C.; Chen, S.; Zhang, J.; Li, Z.; Zhang, X.-M. Mol. Catal. 2018, 452, 145.
[13]	Bai, L.; Wang, X.; Chen, Q.; Ye, Y.; Zheng, H.; Guo, J.; Yin, Y.; Gao, C. Angew. Chem., Int. Ed. 2016, 55, 15656. doi: 10.1002/anie.201609663
[14]	Zhu, D.; Jiang, H.; Zhang, L.; Zheng, X.; Fu, H.; Yuan, M.; Chen, H.; Li, R. ChemCatChem 2014, 6, 2954. doi: 10.1002/cctc.201402519
[15]	Yamaguchi, R.; Ikeda, C.; Takahashi, Y.; Fujita, K.-I. J. Am. Chem. Soc. 2009, 131, 8410. doi: 10.1021/ja9022623 pmid: 19480425
[16]	Guo, X.; Chen, X.; Su, D.; Liang, C. Acta Chim. Sinica 2018, 76, 22. (in Chinese) doi: 10.6023/A17070339
	(郭小玲, 陈霄, 苏党生, 梁长海, 化学学报, 2018, 76, 22.) doi: 10.6023/A17070339
[17]	Zhao, T.; Dong, M.; Zhao, Y.; Liu, Y. Prog. Chem. 2017, 29, 1252. (in Chinese)
	(赵田, 董茗, 赵熠, 刘跃军, 化学进展, 2017, 29, 1252.) doi: 10.7536/PC170541
[18]	Pan, Y.; Qian, Y.; Zheng, X.; Chu, S.-Q.; Yang, Y.; Ding, C.; Wang, X.; Yu, S.-H.; Jiang, H.-L. Natl. Sci. Rev. 2021, 8, 224.
[19]	Wu, Q.; Zhang, C.; Sun, K.; Jiang, H.-L. Acta Chim. Sinica 2020, 78, 688. (in Chinese) doi: 10.6023/A20050141
	(吴浅耶, 张晨曦, 孙康, 江海龙, 化学学报, 2020, 78, 688.) doi: 10.6023/A20050141
[20]	Jiao, L.; Wang, J.; Jiang, H.-L. Acc. Mater. Res. 2021, 2, 327. doi: 10.1021/accountsmr.1c00009
[21]	Choe, K.; Zheng, F.; Wang, H.; Yuan, Y.; Zhao, W.; Xue, G.; Qiu, X.; Ri, M.; Shi, X.; Wang, Y.; Li, G.; Tang, Z. Angew. Chem., Int. Ed. 2020, 59, 3650. doi: 10.1002/anie.201913453
[22]	Zhao, M.; Yuan, K.; Wang, Y.; Li, G.; Guo, J.; Gu, L.; Hu, W.; Zhao, H.; Tang, Z. Nature 2016, 539, 76. doi: 10.1038/nature19763
[23]	Zhang, J.-W.; Li, D.-D.; Lu, G.-P.; Deng, T.; Cai, C. ChemCatChem 2018, 10, 4980.
[24]	Wang, X.; Chen, W.; Zhang, L.; Yao, T.; Liu, W.; Lin, Y.; Ju, H.; Dong, J.; Zheng, L.; Yan, W.; Zheng, X.; Li, Z.; Wang, X.; Yang, J.; He, D.; Wang, Y.; Deng, Z.; Wu, Y.; Li, Y. J. Am. Chem. Soc. 2017, 139, 9419. doi: 10.1021/jacs.7b01686 pmid: 28661130
[25]	Chen, F.; Shen, K.; Chen, J.; Yang, X.; Cui, J.; Li, Y. ACS Central Sci. 2019, 5, 176. doi: 10.1021/acscentsci.8b00805
[26]	Shen, Y.; Pan, T.; Wang, L.; Ren, Z.; Zhang, W.; Huo, F. Adv. Mater. 2021, 33, 2007442. doi: 10.1002/adma.202007442
[27]	Dou, R.; Tan, X.; Fan, Y.; Pei, Y.; Qiao, M.; Fan, K.; Sun, B.; Zong, B. Acta Chim. Sinica 2016, 74, 503. (in Chinese) doi: 10.6023/A16020074
	(窦镕飞, 谭晓荷, 范义秋, 裴燕, 乔明华, 范康年, 孙斌, 宗保宁, 化学学报, 2016, 74, 503.) doi: 10.6023/A16020074
[28]	Ding, S.; Yan, Q.; Jiang, H.; Zhong, Z.; Chen, R.; Xing, W. Chem. Eng. J. 2016, 296, 146. doi: 10.1016/j.cej.2016.03.098
[29]	Ji, Z.; Shen, X.; Yang, J.; Zhu, G.; Chen, K. Appl. Catal. B 2014, 144, 454. doi: 10.1016/j.apcatb.2013.07.052
[30]	Sun, J.; Wang, H.; Gao, X.; Zhu, X.; Ge, Q.; Liu, X.; Han, J. Micropor. Mesopor. Mat. 2017, 247, 1. doi: 10.1016/j.micromeso.2017.03.040
[31]	Lin, L.; Liu, H.; Zhang, X. Chem. Eng. J. 2017, 328, 124. doi: 10.1016/j.cej.2017.07.016
[32]	Hester, P.; Xu, S.; Liang, W.; Al-Janabi, N.; Vakili, R.; Hill, P.; Muryn, C. A.; Chen, X.; Martin, P. A.; Fan, X. J. Catal. 2016, 340, 85. doi: 10.1016/j.jcat.2016.05.003
[33]	Huang, Y.; Liu, S.; Lin, Z.; Li, W.; Li, X.; Cao, R. J. Catal. 2012, 292, 111. doi: 10.1016/j.jcat.2012.05.003
[34]	Li, L.; Li, Z.; Yang, W.; Huang, Y.; Huang, G.; Guan, Q.; Dong, Y.; Lu, J.; Yu, S.-H.; Jiang, H.-L. Chem 2021, 7, 686. doi: 10.1016/j.chempr.2020.11.023
[35]	Chen, D.; Yang, W.; Jiao, L.; Li, L.; Yu, S.-H.; Jiang, H.-L. Adv. Mater. 2020, 32, 2000041. doi: 10.1002/adma.202000041
[36]	Dhakshinamoorthy, A.; Garcia, H. Chem. Soc. Rev. 2012, 41, 5262. doi: 10.1039/c2cs35047e pmid: 22695806
[37]	Fish, R. H.; Kim, H. S.; Fong, R. H. Organometallics 1991, 10, 770. doi: 10.1021/om00049a043
[38]	Fish, R. H.; Michaels, J. N.; Moore, R. S.; Heinemann, H. J. Catal. 1990, 123, 74. doi: 10.1016/0021-9517(90)90158-G
[39]	Li, X.; Van Zeeland, R.; Maligal-Ganesh, R. V.; Pei, Y.; Power, G.; Stanley, L.; Huang, W. ACS Catal. 2016, 6, 6324. doi: 10.1021/acscatal.6b01753
[40]	Cavka, J. H.; Jakobsen, S.; Olsbye, U.; Guillou, N.; Lamberti, C.; Bordiga, S.; Lillerud, K. P. J. Am. Chem. Soc. 2008, 130, 13850. doi: 10.1021/ja8057953
[41]	Zhang, S.; Gan, J.; Xia, Z.; Chen, X.; Zou, Y.; Duan, X.; Qu, Y. Chem 2020, 6, 2994. doi: 10.1016/j.chempr.2020.07.023
[42]	Huang, R.; Cao, C.; Liu, J.; Zheng, L.; Zhang, Q.; Gu, L.; Jiang, L.; Song, W. ACS Appl. Mater. Interf. 2020, 12, 17651. doi: 10.1021/acsami.0c03452
[43]	Shaikh, M. N.; Kalanthoden, A. N.; Ali, M.; Haque, M. A.; Aziz, M. A.; Abdelnaby, M. M.; Rani, S. K.; Bakare, A. I. Chemistryselect 2020, 5, 14827. doi: 10.1002/slct.202003178
[44]	Bravo-Sanabria, C. A.; Solano-Delgado, L. C.; Ospina-Ospina, R.; Martinez-Ortega, F.; Ramirez-Caballero, G. E. Micropor. Mesopor. Mat. 2020, 305, 110359. doi: 10.1016/j.micromeso.2020.110359
[45]	Ozel, A. E.; Buyukmurat, Y.; Akyuz, S. J. Mol. Struct. 2001, 565, 455.
[46]	Yu, H.; Zhang, L.; Gao, S.; Wang, H.; He, Z.; Xu, Y.; Huang, K. J. Catal. 2021, 396, 342. doi: 10.1016/j.jcat.2021.03.002
[47]	Zhan, T.; Liu, W.; Teng, J.; Yue, C.; Li, D.; Wang, S.; Tan, H. Chem. Commun. 2019, 55, 2620. doi: 10.1039/C8CC10273B
[48]	Yu, X.; Nie, R.; Zhang, H.; Lu, X.; Zhou, D.; Xia, Q. Micropor. Mesopor. Mat. 2018, 256, 10. doi: 10.1016/j.micromeso.2017.07.048
[49]	Li, L.; Tang, S.; Wang, C.; Lv, X.; Jiang, M.; Wu, H.; Zhao, X. Chem. Commun. 2014, 50, 2304. doi: 10.1039/c3cc48275h

金属有机框架与Pt粒子复合材料催化喹啉选择性加氢性能研究^※

Study on the Selective Hydrogenation of Quinoline Catalyzed by Composites of Metal-Organic Framework and Pt Nanoparticles^※

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金属有机框架与Pt粒子复合材料催化喹啉选择性加氢性能研究※

Study on the Selective Hydrogenation of Quinoline Catalyzed by Composites of Metal-Organic Framework and Pt Nanoparticles※

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Supporting Info.

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Abstract

Cite this article

share this article

Fig. & Tab. 7

References 49

Related Articles 15

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Comments

金属有机框架与Pt粒子复合材料催化喹啉选择性加氢性能研究^※

Study on the Selective Hydrogenation of Quinoline Catalyzed by Composites of Metal-Organic Framework and Pt Nanoparticles^※