Pd/Py-COF催化喹啉加氢的性能研究

张永欣, 石中亮, 郭淼, 胡雁鸣

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山西大学学报(自然科学版) ›› 2025, Vol. 48 ›› Issue (3) : 596-606. DOI: 10.13451/j.sxu.ns.2024099
化学

Pd/Py-COF催化喹啉加氢的性能研究

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The Promotion Effect of Pd/Py-COF in the Hydrogenation of Quinoline

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摘要

为了提升喹啉加氢制备1,2,3,4-四氢喹啉的反应活性,采用二维亚胺含芘共价有机骨架材料(Py-COF)为载体合成了Pd纳米颗粒催化剂(Pd/Py-COF),结果显示其在喹啉加氢中的活性是商用Pd/C催化剂的2.1倍。高分辨电镜、X射线光电子能谱、CO溶出伏安及对比实验等研究结果表明Pd/Py-COF的高活性来自富电子的Pd表面增加底物吸脱附及喹啉与Py-COF之间的弱相互作用。此外, Pd/Py-COF显示出了良好的循环使用性和底物适用性。该工作强调了采用COF骨架调控金属纳米粒子催化性能的重要性。

Abstract

In this paper, we report that pyrene-containing imine covalent organic framework material (Py-COF) supported Pd nanoparticles exhibit significantly high activity in the hydrogenation of quinoline to 1,2,3,4-tetrahydroquinoline, with a turnover frequency (TOF) value 2.1 times that of commercial Pd/C. Through techniques such as high-resolution electron microscopy, X-ray photoelectron spectroscopy, cyclic voltammetry of CO stripping, and control experiments, we have identified that the heightened activity of the Pd/Py-COF catalyst in quinoline hydrogenation stems from the electron-rich Pd surface, which facilitates substrate adsorption/desorption, and the weak interactions between quinoline and Py-COF. Furthermore, Pd/Py-COF demonstrates excellent recyclability and superior catalytic performance in the hydrogenation of various quinoline derivatives. This work underscores the significance of utilizing COFs to regulate the catalytic performance of metal catalysts.

关键词

共价有机骨架材料 / 钯纳米颗粒 / 喹啉 / 加氢

Key words

covalent organic framework material / Pd nanoparticle / quinoline / hydrogenation

中图分类号

O643

引用本文

导出引用
张永欣 , 石中亮 , 郭淼 , . Pd/Py-COF催化喹啉加氢的性能研究. 山西大学学报(自然科学版). 2025, 48(3): 596-606 https://doi.org/10.13451/j.sxu.ns.2024099
ZHANG Yongxin, SHI Zhongliang, GUO Miao, et al. The Promotion Effect of Pd/Py-COF in the Hydrogenation of Quinoline[J]. Journal of Shanxi University(Natural Science Edition). 2025, 48(3): 596-606 https://doi.org/10.13451/j.sxu.ns.2024099

参考文献

1
KARAKULINA A, GOPAKUMAR A, AKÇOK İ, et al. A Rhodium Nanoparticle-lewis Acidic Ionic Liquid Catalyst for the Chemoselective Reduction of Heteroarenes[J]. Angew Chem Int Ed, 2016, 55(1): 292-296. DOI: 10.1002/anie.201507945 .
2
LI S L, WANG L L, WU M M, et al. Measurable Surface d Charge of Pd as a Descriptor for the Selective Hydrogenation Activity of Quinoline[J]. Chin J Catal, 2020, 41(9): 1337-1347. DOI: 10.1016/s1872-2067(20)63580-x .
3
GUO M, DAI H C, YANG Q H. Promotion Effect of Pd in the Ru/C-catalyzed Hydrogenation of Benzofurans[J]. ACS Catal, 2024, 14(4): 2719-2729. DOI: 10.1021/acscatal.3c05429 .
4
MUTHUKRISHNAN I, SRIDHARAN V, MENÉNDEZ J C. Progress in the Chemistry of Tetrahydroquinolines[J]. Chem Rev, 2019, 119(8): 5057-5191. DOI: 10.1021/acs.chemrev.8b00567 .
5
GONG Y T, ZHANG P F, XU X, et al. A Novel Catalyst Pd@ompg-C3N4 for Highly Chemoselective Hydrogenation of Quinoline under Mild Conditions[J]. J Catal, 2013, 297: 272-280. DOI: 10.1016/j.jcat.2012.10.018 .
6
SUN B, KHAN F A, VALLAT A, et al. NanoRu@hectorite: A Heterogeneous Catalyst with Switchable Selectivity for the Hydrogenation of Quinoline[J]. Appl Catal A Gen, 2013, 467: 310-314. DOI: 10.1016/j.apcata.2013.07.037 .
7
GUO M, LI H, REN Y Q, et al. Improving Catalytic Hydrogenation Performance of Pd Nanoparticles by Electronic Modulation Using Phosphine Ligands[J]. ACS Catal, 2018, 8(7): 6476-6485. DOI: 10.1021/acscatal.8b00872 .
8
CHENG G H, JENTYS A, GUTIÉRREZ O Y, et al. Critical Role of Solvent-modulated Hydrogen-binding Strength in the Catalytic Hydrogenation of Benzaldehyde on Palladium[J]. Nat Catal, 2021, 4: 976-985. DOI: 10.1038/s41929-021-00701-2 .
9
WEI Z Z, SHAO F J, WANG J G. Recent Advances in Heterogeneous Catalytic Hydrogenation and Dehydrogenation of N-heterocycles[J]. Chin J Catal, 2019, 40(7): 980-1002. DOI: 10.1016/s1872-2067(19)63336-x .
10
BAI L C, WANG X, CHEN Q, et al. Explaining the Size Dependence in Platinum-nanoparticle-catalyzed Hydrogenation Reactions[J]. Angew Chem Int Ed, 2016, 55(50): 15656-15661. DOI: 10.1002/anie.201609663 .
11
LI S W, CAO R C, XU M Q, et al. Atomically Dispersed Ir/α-MOC Catalyst with High Metal Loading and Thermal Stability for Water-promoted Hydrogenation Reaction[J]. Natl Sci Rev, 2021, 9(1): nwab026. DOI: 10.1093/nsr/nwab026 .
12
GUO M, LI C, YANG Q H. Accelerated Catalytic Activity of Pd NPs Supported on Amine-rich Silica Hollow Nanospheres for Quinoline Hydrogenation[J]. Catal Sci Technol, 2017, 7(11): 2221-2227. DOI: 10.1039/C7CY00394C .
13
GUO J, JIANG D L. Covalent Organic Frameworks for Heterogeneous Catalysis: Principle, Current Status, and Challenges[J]. ACS Cent Sci, 2020, 6(6): 869-879. DOI: 10.1021/acscentsci.0c00463 .
14
YUSRAN Y, LI H, GUAN X Y, et al. Covalent Organic Frameworks for Catalysis[J]. EnergyChem, 2020, 2(3): 100035. DOI: 10.1016/j.enchem.2020.100035 .
15
GUO M, JAYAKUMAR S, LUO M F, et al. The Promotion Effect of Π-Π Interactions in Pd NPs Catalysed Selective Hydrogenation[J]. Nat Commun, 2022, 13(1): 1770. DOI: 10.1038/s41467-022-29299-0 .
16
LI C Z, REN X M, GUO M, et al. Highly Active Ultrafine Pd NPs Confined in Imine-linked COFs for Nitrobenzene Hydrogenation[J]. Catal Sci Technol, 2021, 11(11): 3873-3879. DOI: 10.1039/D1CY00129A .
17
GUO M, KONG X T, LI C Z, et al. Hydrogenation of Benzoic Acid Derivatives over Pt/TiO2 Under Mild Conditions[J]. Commun Chem, 2021, 4(1): 54. DOI: 10.1038/s42004-021-00489-z .
18
CHEN G X, XU C F, HUANG X Q, et al. Interfacial Electronic Effects Control the Reaction Selectivity of Platinum Catalysts[J]. Nat Mater, 2016, 15(5): 564-569. DOI: 10.1038/nmat4555 .
19
HAN Z Y, LIU G, YANG X L, et al. Enantiodivergent Synthesis of Chiral Tetrahydroquinoline Derivatives via Ir-catalyzed Asymmetric Hydrogenation: Solvent-dependent Enantioselective Control and Mechanistic Investigations[J]. ACS Catal, 2021, 11(12): 7281-7291. DOI: 10.1021/acscatal.1c01353 .
20
DING X L, CHEN Y, NAN J P, et al. Ultrasmall Palladium Nanoparticles Anchored on N-doped Nestlike Carbon Nanosheets for Selective Hydrogenation of Quinolines[J]. ACS Sustainable Chem Eng, 2022, 10(42): 14011-14023. DOI: 10.1021/acssuschemeng.2c04585 .
21
WANG M D, GUO M, REN X M, et al. The Influence of Surface Structure of RhPt Bimetallic Nanoparticles on the Hydrogenation of Aromatic Compounds[J]. J Phys Chem C, 2021, 125(28): 15275-15282. DOI: 10.1021/acs.jpcc.1c03624 .
22
SHI S, YANG P P, DUN C C, et al. Selective Hydrogenation via Precise Hydrogen Bond Interactions on Catalytic Scaffolds[J]. Nat Commun, 2023, 14(1): 429. DOI: 10.1038/s41467-023-36015-z .
23
REN X M, GUO M, LI H, et al. Microenvironment Engineering of Ruthenium Nanoparticles Incorporated into Silica Nanoreactors for Enhanced Hydrogenations[J]. Angew Chem Int Ed, 2019, 58(41): 14483-14488. DOI: 10.1002/anie.201908602 .
24
SANTAROSSA G, IANNUZZI M, VARGAS A, et al. Adsorption of Naphthalene and Quinoline on Pt, Pd and Rh: A DFT Study[J]. ChemPhysChem, 2008, 9(3): 401-413. DOI: 10.1002/cphc.200700534 .

基金

国家自然科学基金(22202200)
兴辽英才计划(XLYC2008022)

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