Amine-functionalized metal-organic frameworks loaded with Ag nanoparticles for cycloaddition of CO<sub>2</sub> to epoxides

doi:10.1007/s11705-024-2477-2

Front. Chem. Sci. Eng.

2024, Vol. 18

Issue (11) : 126 https://doi.org/10.1007/s11705-024-2477-2

Amine-functionalized metal-organic frameworks loaded with Ag nanoparticles for cycloaddition of CO₂ to epoxides

Huiyu Fu, Jiewen Wu, Changhai Liang(

), Xiao Chen(

)

State Key Laboratory of Fine Chemicals & Laboratory of Advanced Materials and Catalytic Engineering, School of Chemical Engineering, Dalian University of Technology, Dalian 116024, China

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Abstract

With the advantages of low raw material cost and 100% atom utilization, the synthesis of high value-added chemical product cyclic carbonates by the cycloaddition of CO₂ to epoxides has become one of the most prospective approaches to achieve the industrial utilization of CO₂. In the reported catalytic systems, the complexity of the catalyst synthesis process, high cost, separation difficulties, and low CO₂ capture limit the catalytic efficiency and its large-scale application. In this paper, Ag nanoparticles loaded on polyethyleneimine (PEI)-modified UiO-66-NH₂ (Ag/PEI@UiO-66-NH₂) are successfully synthesized by in situ immersion reduction. The Ag nanoparticles and the amino groups on the surfaces of PEI@UiO-66-NH₂ contribute to the adsorption of CO₂ and polarization of C–O bonds in epoxides, thereby boosting the conversion capability for the CO₂ cycloaddition reaction. At the amount of propylene oxide of 0.25 mol and the catalyst dosage of 1% of the substrate, the yield and selectivity of propylene carbonate are up to 99%. In addition, the stability and recyclability of Ag/PEI@UiO-66-NH₂ catalyst are attained. The Ag/PEI@UiO-66-NH₂ catalyst also demonstrates a wide range of activity and distinctive selectivity toward cyclo-carbonates in the cycloaddition of CO₂ to epoxides. This work provides a guide to designing a highly efficient catalyst for in situ capture and high-value utilization of CO₂ in industrial applications.

Keywords cycloaddition CO₂ capture cyclic carbonates amine-functionalized UiO-66-NH₂ Ag NPs

Corresponding Author(s): Changhai Liang,Xiao Chen

Just Accepted Date: 21 May 2024 Issue Date: 19 July 2024

Cite this article:

Huiyu Fu,Jiewen Wu,Changhai Liang, et al. Amine-functionalized metal-organic frameworks loaded with Ag nanoparticles for cycloaddition of CO₂ to epoxides[J]. Front. Chem. Sci. Eng., 2024, 18(11): 126.

URL:

https://academic.hep.com.cn/fcse/EN/10.1007/s11705-024-2477-2
https://academic.hep.com.cn/fcse/EN/Y2024/V18/I11/126

Scheme1 Synthesis scheme of Ag/PEI@UiO-66-NH₂.

Fig.1 (a) XRD patterns and (b) FTIR spectra of UiO-66-NH₂, UiO-66-GD, and PEI@UiO-66-NH₂ samples.

Fig.2 SEM images of (a) UiO-66-NH₂, (b) UiO-66-GD, and (c) PEI@UiO-66-NH₂ samples.

Fig.3 (a) FTIR spectra of xPEI@UiO-66-NH₂ (x = 30%, 40%, 50%, 60%, and 70%) and (b) XRD patterns of Ag/xPEI@UiO-66-NH₂ (x = 30%, 40%, 50%, 60%, and 70%).

Fig.4 (a) SEM image, (b) TEM image with the particle size statistics of Ag NPs (c), (d) HRTEM image, (e) STEM image, and (f) element mappings of Ag/50% PEI@UiO-66-NH₂.

Tab.1 Pore structure of PEI@UiO-66-NH₂ and Ag/PEI@UiO-66-NH₂

Fig.5 Nitrogen adsorption and desorption isotherms and pore size distributions of (a) PEI@UiO-66-NH₂ and (b) Ag/PEI@UiO-66-NH₂ at 77 K.

Fig.6 CO₂ adsorption and desorption isotherms of (a) PEI@UiO-66-NH₂ and (b) Ag/PEI@UiO-66-NH₂ at 273 and 298 K.

Fig.7 XPS spectra of Ag/50% PEI@UiO-66-NH₂ with (a) full spectrum, (b) Ag 3d.

Tab.2 Catalysts screening for the cycloaddition of CO₂ with propylene oxide^{a, b)}

Fig.8 Effect of (a) reaction pressure, (b) reaction temperature, (c) reaction time, and (d) amount of PEI introduced on the cycloaddition of CO₂ and propylene oxide.

Tab.3 Comparison of catalytic conditions and performances of different catalysts

Fig.9 The cycling stability test of Ag/PEI@UiO-66-NH₂ catalyst.

Tab.4 Substrate scope of the cycloaddition of CO₂ catalyzed by Ag/PEI@UiO-66-NH₂^{a, b)}

Fig.10 Possible mechanism for the cycloaddition of CO₂ with PO over Ag/PEI@UiO-66-NH₂ catalyst.

1	M He , Y Sun , B Han . Green carbon science: efficient carbon resource processing, utilization, and recycling towards carbon neutrality. Angewandte Chemie International Edition, 2022, 61(15): e202112835 https://doi.org/10.1002/anie.202112835
2	M D Burkart , N Hazari , C L Tway , E L Zeitler . Opportunities and challenges for catalysis in carbon dioxide utilization. ACS Catalysis, 2019, 9(9): 7937–7956 https://doi.org/10.1021/acscatal.9b02113
3	Q Chen , M Lv , Z Tang , H Wang , W Wei , Y Sun . Opportunities of integrated systems with CO2 utilization technologies for green fuel & chemicals production in a carbon-constrained society. Journal of CO2 Utilization, 2016, 14: 1–9
4	Z Chen , Y Zhi , W Li , S Li , Y Liu , X Tang , T Hu , L Shi , S Shan . One-step synthesis of nitrogen-rich organic polymers for efficient catalysis of CO2 cycloaddition. Environmental Science and Pollution Research International, 2023, 30(25): 67290–67302 https://doi.org/10.1007/s11356-023-26728-5
5	P P Pescarmona . Cyclic carbonates synthesised from CO2: applications, challenges and recent research trends. Current Opinion in Green and Sustainable Chemistry, 2021, 29: 100457 https://doi.org/10.1016/j.cogsc.2021.100457
6	J Zhang , L Wang , S Liu , Z Li . Synthesis of diverse polycarbonates by organocatalytic copolymerization of CO2 and epoxides: from high pressure and temperature to ambient conditions. Angewandte Chemie International Edition, 2022, 61(4): e202111197 https://doi.org/10.1002/anie.202111197
7	F Zhang , Y Wang , X Zhang , X Zhang , H Liu , B Han . Recent advances in the coupling of CO2 and epoxides into cyclic carbonates under halogen-free condition. Green Chemical Engineering, 2020, 1(2): 82–93 https://doi.org/10.1016/j.gce.2020.09.008
8	Y Ecochard , J Leroux , B Boutevin , R Auvergne , S Caillol . From multi-functional siloxane-based cyclic carbonates to hybrid polyhydroxyurethane thermosets. European Polymer Journal, 2019, 120: 109280 https://doi.org/10.1016/j.eurpolymj.2019.109280
9	C Martín , G Fiorani , A W Kleij . Recent advances in the catalytic preparation of cyclic organic carbonates. ACS Catalysis, 2015, 5(2): 1353–1370 https://doi.org/10.1021/cs5018997
10	F Della Monica , B Maity , T Pehl , A Buonerba , A De Nisi , M Monari , A Grassi , B Rieger , L Cavallo , C Capacchione . [OSSO]-type iron(III) complexes for the low-pressure reaction of carbon dioxide with epoxides: catalytic activity, reaction kinetics, and computational study. ACS Catalysis, 2018, 8(8): 6882–6893 https://doi.org/10.1021/acscatal.8b01695
11	J W Comerford , I D V Ingram , M North , X Wu . Sustainable metal-based catalysts for the synthesis of cyclic carbonates containing five-membered rings. Green Chemistry, 2015, 17(4): 1966–1987 https://doi.org/10.1039/C4GC01719F
12	S Zhong , L Liang , B Liu , J Sun . ZnBr2/DMF as simple and highly active Lewis acid-base catalysts for the cycloaddition of CO2 to propylene oxide. Journal of CO2 Utilization, 2014, 6: 75–79
13	A Belinchón , R Santiago , E Hernández , C Moya , P Navarro , J Palomar . Reaction-extraction platforms towards CO2-derived cyclic carbonates catalyzed by ionic liquids. Journal of Cleaner Production, 2022, 368: 133189 https://doi.org/10.1016/j.jclepro.2022.133189
14	J Q Wang , W G Cheng , J Sun , T Y Shi , X P Zhang , S J Zhang . Efficient fixation of CO2 into organic carbonates catalyzed by 2-hydroxymethyl-functionalized ionic liquids. RSC Advances, 2013, 4(5): 2360–2367 https://doi.org/10.1039/C3RA45918G
15	Y A Alassmy , P P Pescarmona . The role of water revisited and enhanced: a sustainable catalytic system for the conversion of CO2 into cyclic carbonates under mild conditions. ChemSusChem, 2019, 12(16): 3856–3863 https://doi.org/10.1002/cssc.201901124
16	J Noh , Y Kim , H Park , J Lee , M Yoon , M H Park , Y Kim , M Kim . Functional group effects on a metal-organic framework catalyst for CO2 cycloaddition. Journal of Industrial and Engineering Chemistry, 2018, 64: 478–483 https://doi.org/10.1016/j.jiec.2018.04.010
17	K Yamaguchi , K Ebitani , T Yoshida , H Yoshida , K Kaneda . Mg-Al mixed oxides as highly active acid-base catalysts for cycloaddition of carbon dioxide to epoxides. Journal of the American Chemical Society, 1999, 121(18): 4526–4527 https://doi.org/10.1021/ja9902165
18	S M Masoom Nataj , S Kaliaguine , F G Fontaine . Highly efficient catalysts for CO2 fixation using guanidinium-functionalized Zr-MOFs. ChemCatChem, 2023, 15(10): e202300079 https://doi.org/10.1002/cctc.202300079
19	S Liu , M L Gao , C N Li , L Liu , Z B Han . Superhydrophobic MOFs with enhanced catalytic activity for chemical fixation of CO2. Dalton Transactions, 2023, 52(40): 14319–14323 https://doi.org/10.1039/D3DT02188B
20	A Xu , Z Chen , L Jin , B Chu , J Lu , X He , Y Yao , B Li , L Dong , M Fan . Quaternary ammonium salt functionalized MIL-101-NH2(Cr) as a bifunctional catalyst for the cycloaddition of CO2 with epoxides to produce cyclic carbonates. Applied Catalysis A, General, 2021, 624: 118307 https://doi.org/10.1016/j.apcata.2021.118307
21	Y Jiang , P Tan , S C Qi , X Q Liu , J H Yan , F Fan , L B Sun . Metal-organic frameworks with target-specific active sites switched by photoresponsive motifs: efficient adsorbents for tailorable CO2 capture. Angewandte Chemie International Edition, 2019, 58(20): 6600–6604 https://doi.org/10.1002/anie.201900141
22	D Bahamon , W Anlu , S Builes , M Khaleel , L F Vega . Effect of amine functionalization of MOF adsorbents for enhanced CO2 capture and separation: a molecular simulation study. Frontiers in Chemistry, 2021, 8: 574622 https://doi.org/10.3389/fchem.2020.574622
23	S Yan , W Li , D He , G He , H Chen . Recent research progress of metal-organic frameworks (MOFs) based catalysts for CO2 cycloaddition reaction. Molecular Catalysis, 2023, 550: 113608 https://doi.org/10.1016/j.mcat.2023.113608
24	Z Taşcı , A Kunduracıoğlu , İ Kani , B Çetinkaya . A new application area for Ag-NHCs: CO2 fixation catalyst. ChemCatChem, 2012, 4(6): 831–835 https://doi.org/10.1002/cctc.201100430
25	C Y Gao , C Mao , Y Yang , N Xu , J Liu , X Chen , J Liu , L Duan . Epoxide activation by a silver phosphonate for heterogeneous catalysis of CO2 cycloaddition. CrystEngComm, 2022, 25(1): 108–113 https://doi.org/10.1039/D2CE01240E
26	D Wu , X Lu , Y Tang , F Gao , G Yang , Y Y Wang . Light-assisted CO2 cycloaddition over a nanochannel cadmium-organic framework loaded with silver nanoparticles. ACS Applied Nano Materials, 2023, 6(7): 6197–6207 https://doi.org/10.1021/acsanm.3c00499
27	X Liu , C Hu , J Wu , H Zhu , Y Li , P Cui , F Wei . The assembly of novel Ag-based NP@MOFs mesoporous spherical composites and their enhanced catalytic performance in photodegradation and chemical conversion of CO2 with epoxide. Journal of Solid State Chemistry, 2021, 296: 121889 https://doi.org/10.1016/j.jssc.2020.121889
28	G Li , X Sui , X Cai , W Hu , X Liu , M Chen , Y Zhu . Precisely constructed silver active sites in gold nanoclusters for chemical fixation of CO2. Angewandte Chemie International Edition, 2021, 60(19): 10573–10576 https://doi.org/10.1002/anie.202100071
29	S Li , F Feng , S Chen , X Zhang , Y Liang , S Shan . Preparation of UiO-66-NH2 and UiO-66-NH2/sponge for adsorption of 2,4-dichlorophenoxyacetic acid in water. Ecotoxicology and Environmental Safety, 2020, 194: 110440 https://doi.org/10.1016/j.ecoenv.2020.110440
30	S Z Hu , T Huang , N Zhang , Y Z Lei , Y Wang . Enhanced removal of lead ions and methyl orange from wastewater using polyethyleneimine grafted UiO-66-NH2 nanoparticles. Separation and Purification Technology, 2022, 297: 121470 https://doi.org/10.1016/j.seppur.2022.121470
31	K Li , J Jiang , F Yan , S Tian , X Chen . The influence of polyethyleneimine type and molecular weight on the CO2 capture performance of PEI-nano silica adsorbents. Applied Energy, 2014, 136: 750–755 https://doi.org/10.1016/j.apenergy.2014.09.057
32	P C Lemaire , D T Lee , J Zhao , G N Parsons . Reversible low-temperature metal node distortion during atomic layer deposition of Al2O3 and TiO2 on UiO-66-NH2 metal-organic framework crystal surfaces. ACS Applied Materials & Interfaces, 2017, 9(26): 22042–22054 https://doi.org/10.1021/acsami.7b05214
33	H Zeng , Z Yu , L Shao , X Li , M Zhu , Y Liu , X Feng , X Zhu . A novel strategy for enhancing the performance of membranes for dyes separation: embedding PAA@UiO-66-NH2 between graphene oxide sheets. Chemical Engineering Journal, 2021, 403: 126281 https://doi.org/10.1016/j.cej.2020.126281
34	A Pankajakshan , M Sinha , A A Ojha , S Mandal . Water-stable nanoscale zirconium-based metal-organic frameworks for the effective removal of glyphosate from aqueous media. ACS Omega, 2018, 3(7): 7832–7839 https://doi.org/10.1021/acsomega.8b00921
35	Z Ji , H Sun , Y Zhu , D Zhang , L Wang , F Dai , Y Zhao , L Chen . Enhanced selective removal of lead ions using a functionalized PAMAM@UiO-66-NH2 nanocomposite: experiment and mechanism. Microporous and Mesoporous Materials, 2021, 328: 111433 https://doi.org/10.1016/j.micromeso.2021.111433
36	W Z Xiao , L P Xiao , Y Q Yang , S R Zhai , R C Sun . Catalytic degradation of organic pollutants for water remediation over Ag nanoparticles immobilized on amine-functionalized metal-organic frameworks. Nano Research, 2022, 15(9): 7887–7895 https://doi.org/10.1007/s12274-022-4436-x
37	J Jin , J Xue , D Wu , G Yang , Y Wang . Improved performance of the pyrimidine-modified porous In-MOF and an in situ prepared composite Ag@In-MOF material. Chemical Communications, 2022, 58(56): 7749–7752 https://doi.org/10.1039/D2CC02639B
38	X Zhang , H Liu , Y Shi , J Han , Z Yang , Y Zhang , C Long , J Guo , Y Zhu , X Qiu . et al.. Boosting CO2 conversion with terminal alkynes by molecular architecture of graphene oxide-supported Ag nanoparticles. Matter, 2020, 3(2): 558–570 https://doi.org/10.1016/j.matt.2020.07.022
39	Z Wu , Q Liu , X Yang , X Ye , H Duan , J Zhang , B Zhao , Y Huang . Knitting aryl network polymers-incorporated Ag nanoparticles: a mild and efficient catalyst for the fixation of CO2 as carboxylic acid. ACS Sustainable Chemistry & Engineering, 2017, 5(11): 9634–9639 https://doi.org/10.1021/acssuschemeng.7b02678
40	X Lan , Q Li , L Cao , C Du , L Ricardez Sandoval , G Bai . Rebuilding supramolecular aggregates to porous hollow N-doped carbon tube inlaid with ultrasmall Ag nanoparticles: a highly efficient catalyst for CO2 conversion. Applied Surface Science, 2020, 508: 145220 https://doi.org/10.1016/j.apsusc.2019.145220
41	V I Isaeva , M N Timofeeva , I A Lukoyanov , E Y Gerasimov , V N Panchenko , V V Chernyshev , L M Glukhov , L M Kustov . Novel MOF catalysts based on calix[4]arene for the synthesis of propylene carbonate from propylene oxide and CO2. Journal of CO2 Utilization, 2022, 66: 102262
42	Aouni N El , Redondo C López , M B Yeamin , A Aghmiz , M Reguero , A M Masdeu-Bultó . Influence of structural properties of zinc complexes with N-donor ligands on the catalyzed cycloaddition of CO2 to epoxides into cyclic carbonates. Molecular Catalysis, 2023, 538: 112992 https://doi.org/10.1016/j.mcat.2023.112992
43	D H Lan , F M Yang , S L Luo , C T Au , S F Yin . Water-tolerant graphene oxide as a high-efficiency catalyst for the synthesis of propylene carbonate from propylene oxide and carbon dioxide. Carbon, 2014, 73: 351–360 https://doi.org/10.1016/j.carbon.2014.02.075
44	R Patra , D Sarma . A thiol-containing zirconium MOF functionalized with silver nanoparticles for synergistic CO2 cycloaddition reactions. Dalton Transactions, 2023, 52(31): 10795–10804 https://doi.org/10.1039/D3DT01583A

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