HCO₃^- modified N-heterocyclic carbene silver organic porous polymer catalyzes the conversion of low concentration CO₂ into oxazolidinone compounds

Abstract

Silver metalized organic porous polymer (Ag@POP-HCO₃) was prepared by copolymerizing the HCO₃^- modified N-heterocyclic carbene monomer loading silver with divinylbenzene. The in-situ conversion of low concentration CO₂ from coal-fired flue gas or air into oxazolidinone compounds was achieved through carboxylation cyclization reaction catalyzed by Ag@POP-HCO₃ under ambient conditions, without the addition of any cocatalyst. Additionally, both SO₂ and NO₂ did not interfere with the reaction at normal concentration presented in flue gas. The Ag@POP-HCO₃ can effectively catalyze the gram reaction, and its catalytic activity is not significantly reduced after being recycled. The introduction of HCO₃^- increased the specific surface area and microporous volumes of the catalyst, enhancing its ability to adsorb CO₂. Furthermore, N-heterocyclic carbene and HCO₃^- collaborated to expedite the activation of CO₂, while the coordination of silver serves to activate the substrate. The proposed approach avoids cost issues of traditional carbon capture, utilization and storage technology and promotes green chemical process development.

Keywords

HCO₃^- modified N-heterocyclic carbene silver organic porous polymer / carboxylation cyclization reaction / low concentration CO₂ / coal-fired flue gas / air

References

[1] Shakoor A,Shakoor S,Rehman A.Biogeochemical transformation of greenhouse gas emissions from terrestrial to atmospheric environment and potential feedback to climate forcing.Environ Sci Pollut Res2020;27:38513-36

[2] Nocito F.Atmospheric CO2 mitigation technologies: carbon capture utilization and storage.Curr Opin Green Sustain Chem2020;21:34-43

[3] Gadikota G,Santos RM.Editorial: emerging technologies and associated scientific advancements for CCUS deployment.Front Energy Res2021;9:649126

[4] Chatterjee S,Huang K.Limitations of ammonia as a hydrogen energy carrier for the transportation sector.ACS Energy Lett2021;6:4390-4

[5] Xiong T,Zhang M,Pan Y.Electrochemical-mediated fixation of CO ₂ : three-component synthesis of carbamate compounds from CO ₂ , amines and N -alkenylsulfonamides.Green Chem2021;23:4328-32

[6] Zhou X,Cui F,Li S.Electrocatalytic three-component reactions: synthesis of tellurium-containing oxazolidinone for anticancer agents.Green Chem2023;25:5024-9

[7] Wang P,Li N.CCUS development in China and forecast its contribution to emission reduction.Sci Rep2023;13:17811 PMCID:PMC10587302

[8] Rao ZX,Xu J.Direct conversion of CO₂ in lime kiln waste gas catalyzed by a copper-based N-heterocyclic carbene porous polymer.ChemSusChem2023;16:e202300170

[9] Liang Y,Shen XX.A six-membered N-heterocyclic polyionic liquids with palladium nanoparticles as a heterogeneous catalyst for the multicomponent one-pot reaction of carbon dioxide.J Colloid Interface Sci2025;678:754-65

[10] Chen PB,Rao ZX.Efficient in-situ conversion of low-concentration carbon dioxide in exhaust gas using silver nanoparticles in N-heterocyclic carbene polymer.J Colloid Interface Sci2023;652:866-77

[11] Wen J,Liu Y.Triphenylimidazolium-incorporated, benzbisimidazole-linked porous organic polymers as efficient catalyst for CO₂ conversion.Micropor Mesopor Mater2022;339:111999

[12] Du C,An G,Bai G.Direct surface modification of graphitic C₃N ₄ with porous organic polymer and silver nanoparticles for promoting CO₂ conversion.ACS Sustainable Chem Eng2020;8:7051-8

[13] Zhang X,Zhou Z.Reduced graphene oxide supported ag nanoparticles: an efficient catalyst for CO₂ conversion at ambient conditions.ChemCatChem2020;12:4825-30

[14] Hong J,Zhang J,Mo F.C-H bond carboxylation with carbon dioxide.ChemSusChem2019;12:6-39

[15] Chen XC,Zhao KC,Lu Y.Cooperative catalysis of Ru(III)-porphyrin in CO₂ -involved synthesis of oxazolidinones.Chem Asian J2021;16:2504-10

[16] Mei C,Chen Q,Pang G.Synthesis of oxazolidinones and derivatives through three-component fixation of carbon dioxide.ChemCatChem2018;10:3057-68

[17] Wu J,Cui J,Zhang J.Nitrogen-rich porous organic polymers with supported ag nanoparticles for efficient CO₂ conversion.Nanomaterials2022;12:3088 PMCID:PMC9501012

[18] Kumar A,Sharma N,Mahajan D.Catalyst free N-formylation of aromatic and aliphatic amines exploiting reductive formylation of CO₂ using NaBH₄.RSC Adv2021;11:25777-87 PMCID:PMC9037105

[19] Zhang Q,Zeng A.Carboxylate-assisted carboxylation of thiophene with CO₂ in the solvent-free carbonate medium.Catalysts2022;12:369

[20] Tang X,Chen P.Effective N-formylation of amines with CO₂ in anaerobic fermentation gas catalyzed by triply synergistic effect of ionic porous organic polymer.ChemCatChem2023;15:e202201351

[21] Liang Y,Yang J,Hu X.Efficient in-situ conversion of low-concentration carbon dioxide in coal-fired flue gas using silver nanoparticles in amino-functionalism poly-ionic liquids.Chem Eng J2024;498:155305

[22] Lux S,Siebenhofer M.Hydrogenation of inorganic metal carbonates: a review on its potential for carbon dioxide utilization and emission reduction.ChemSusChem2018;11:3357-75 PMCID:PMC6221144

[23] Chen P,Meng X,Pan Y.Transition metal-free catalytic formylation of carbon dioxide and amide with novel poly(ionic liquid)s.Green Synth Catal2022;3:162-7

[24] Li WH,Xiong HY.Constructing mononuclear palladium catalysts by precoordination/solvothermal polymerization: recyclable catalyst for regioselective oxidative heck reactions.Angew Chem Int Ed2019;58:2448-53

[25] Chen P,Pan Y.Recent progress on N-heterocyclic Carbene catalysts in chemical fixation of CO₂.Asian J Org Chem2022;11:e202100738

[26] Yoshida S,Kikuchi S.Silver-catalyzed preparation of oxazolidinones from carbon dioxide and propargylic amines.Chemistry Letters2009;38:786-7

[27] Ishida T,Yamada T.Novel method of tetramic acid synthesis: silver-catalyzed carbon dioxide incorporation into propargylic amine and intramolecular rearrangement.Org Lett2014;16:2430-3

[28] Ghosh S,Kayal U,Islam SM.Ag NPs decorated on a COF in the presence of DBU as an efficient catalytic system for the synthesis of tetramic acids via CO₂ fixation into propargylic amines at atmospheric pressure.Dalton Trans2019;48:4657-66

[29] Yang H,Zhang G.An alkaline-resistant Ag(I)-anchored pyrazolate-based metal-organic framework for chemical fixation of CO₂. .Chem Commun2018;54:4469-72

[30] Wei ZQ,Hong RY.Monodisperse plum-like sulfonated PGMA-DVB microspheres as a new ion exchange resin.J of Applied Polymer Sci2017;134:app.44994

[31] Cong H,Ding X,Shen Y.Preparation of porous sulfonated poly(styrene-divinylbenzene) microspheres and its application in hydrophilic and chiral separation.Talanta2020;210:120586

[32] Zhao T,Liang H,Hu X.One-pot synthesis of cyclic carbonates from olefins and CO₂ catalyzed by silica-supported imidazolium hydrogen carbonate ionic liquids.Microporous Mesoporous Mater2023;356:112576

[33] Yang W,Wu Q.Functionalized core–shell polystyrene sphere-supported alkaline imidazolium ionic liquid: an efficient and recyclable catalyst for knoevenagel condensation.ACS Sustainable Chem Eng2020;8:18126-37

[34] Fu J,Hu X.Synthesis of amphiphilic AIE fluorescent nanoparticles via CO₂ involved multicomponent reaction and its biological imaging potential.Dyes and Pigments2023;210:110990

[35] Li D,Mao D,Zhou Y.Direct synthesis of sulfonic group tethered mesoporous poly(ionic liquid) for catalyzing deoximation reactions.Mater Chem Phys2017;189:118-26

[36] An R,Zhang R.Synthesis of propylene glycol methyl ether catalyzed by imidazole polymer catalyst: performance evaluation, kinetics study, and process simulation. Chem Eng J2021;405:126636

[37] Zhang W,Ma L,Wang J.Imidazolium-functionalized ionic hypercrosslinked porous polymers for efficient synthesis of cyclic carbonates from simulated flue gas.ChemSusChem2020;13:341-50

[38] Wang X,Guo Z,Zhou Y.Synergistic catalysis of one-pot cascade reactions by acidic and basic binary porous polymers.Appl Surf Sci2019;478:221-9

[39] Ramos Guivar JA,Bruns F.Vacancy ordered γ-Fe₂O₃ nanoparticles functionalized with nanohydroxyapatite: XRD, FTIR, TEM, XPS and mössbauer studies.Appl Surf Sci2016;389:721-34

[40] Bai X,Yan F.Thiadiazol-based conjugated organic polymer anchoring ag nanoparticles for efficient conversion of CO₂ into oxazolidinones from propargylic amines.Appl Surf Sci2022;604:154566

[41] Wang X,Wang J.A dual-functional urea-linked conjugated porous polymer anchoring silver nanoparticles for highly efficient CO₂ conversion under mild conditions.Dalton Trans2020;49:13052-9

[42] Li Z,Yin Z.Interface-enhanced catalytic selectivity on the C₂ Products of CO₂ electroreduction.ACS Catal2021;11:2473-82

[43] Guđmundsson A,Mai BK,Himo F.Diastereoselective synthesis of N -protected 2,3-dihydropyrroles via iron-catalyzed cycloisomerization of α-allenic sulfonamides.ACS Catal2019;9:1733-7