Abstract
Efficient and sustainable chemical fixation of CO2 into value-added chemicals is one of the most promising objectives in environmental chemistry. In this work, transition metal acetylacetonate immobilized onto triazolium ionic liquid-modified periodic mesoporous organosilica PMO-IL-M(x) was successfully prepared and investigated as an effective and heterogeneous catalyst in the direct carboxylation of terminal alkynes and CO2 to the desired alkynyl carboxylic acids. It was found that the catalyst PMO-IL-Sn(0.3) exhibited extraordinary catalytic performance in terms of excellent activity, stability, productivity, and excellent yields under mild reaction conditions. Moreover, the catalyst PMO-IL-Sn(0.3) could be easily recovered and reused at least six times without considerable loss in catalytic activity. This work provides a sustainable and efficient synergistic strategy for the chemical fixation of carbon dioxide into valuable alkynyl carboxylic acids.
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References
Abd AA, Othman MR, Kim J (2021) A review on application of activated carbons for carbon dioxide capture: present performance, preparation, and surface modification for further improvement. Environ Sci Pollut Res 28:43329–43364. https://doi.org/10.1007/s11356-021-15121-9
Adamcsik B, Nagy E, Urbán B, Szabó P, Pekker P, Skoda-Földes R (2020) Palladium nanoparticles on a pyridinium supported ionic liquid phase: a recyclable and low-leaching palladium catalyst for aminocarbonylation reactions. RSC Adv 10:23988–23998. https://doi.org/10.1039/D0RA03406A
Aresta M, Dibenedetto A, Angelini A (2014) Catalysis for the valorization of exhaust carbon: from CO2 to chemicals, materials, and fuels. Technological use of CO2. Chem Rev 114:1709–1742. https://doi.org/10.1021/cr4002758
Arndt M, Risto E, Krause T, Gooßen LJ (2012) C-H carboxylation of terminal alkynes catalyzed by low loadings of silver(I)/DMSO at ambient CO2 pressure. ChemCatChem 4:484–487. https://doi.org/10.1002/cctc.201200047
Bavoh CB, Nashed O, Rehman AN, Othaman NAAB, Lal B, Sabil KM (2021) Ionic liquids as gas hydrate thermodynamic inhibitors. Ind Eng Chem Res 60:15835–15873. https://doi.org/10.1021/acs.iecr.1c01401
Beil S, Markiewicz M, Pereira CS, Stepnowski P, Thöming J, Stolte S (2021) Toward the proactive design of sustainable chemicals: ionic liquids as a prime example. Chem Rev 121:13132–13173. https://doi.org/10.1021/acs.chemrev.0c01265
Bian C, Wu Q, Zhang J, Pan S, Wang L, Meng X, Xiao FS (2015) Interlayer expansion of the layered zeolite precursor COK-5 with Sn(acac)2Cl2. J Energy Chem 24:642–645. https://doi.org/10.1016/j.jechem.2015.09.002
Bordet A, Moos G, Welsh C, Licence P, Luska KL, Leitner W (2020) Molecular control of the catalytic properties of rhodium nanoparticles in supported ionic liquid phase (SILP) systems. ACS Catal 10:13904–13912. https://doi.org/10.1021/acscatal.0c03559
Bresciani G, Marchetti F, Pampaloni G (2019) Carboxylation of terminal alkynes promoted by silver carbamate at ambient pressure. New J Chem 43:10821–10825. https://doi.org/10.1039/C9NJ02203A
Bu R, Zhang L, Gao LL, Sun WJ, Yang SL, Gao EQ (2021) Copper(I)-modified covalent organic framework for CO2 insertion to terminal alkynes. Mol Catal 499:111319. https://doi.org/10.1016/j.mcat.2020.111319
Chand D, Wilk-Kozubek M, Smetana V, Mudring AV (2019) Alternative to the popular imidazolium ionic liquids: 1,2,4-triazolium ionic liquids with enhanced thermal and chemical stability. ACS Sustainable Chem Eng 7:15995–16006. https://doi.org/10.1021/acssuschemeng.9b02437
Chaugule AA, Tamboli AH (2017) Kim H (2017) CuCl2@Poly-IL catalyzed carboxylation of terminal alkynes through CO2 utilization. Chem Eng J 326:1009–1019. https://doi.org/10.1016/j.cej.2017.06.011
Chen M, Wu Q, Lin C, Zhang J, Zhao J, Chen J, Xu Y (2020) Chemical fixation of CO2 using highly dispersed Cu on hierarchically porous N-doped carbon. ACS Appl Mater Interf 12:40236–40247. https://doi.org/10.1021/acsami.0c08001
Chen T, Yang X, Wang S, Song G, Zhou H, Shen W, Gao L (2021) A new ionic liquid bridged periodic mesoporous organosilicas stationary phase for per aqueous liquid chromatography and its application in the detection of biogenic amines. Talanta 235:122795. https://doi.org/10.1016/j.talanta.2021.122795
Cui G, Wang J, Zhang S (2016) Active chemisorption sites in functionalized ionic liquids for carbon capture. Chem Soc Rev 45:4307–4339. https://doi.org/10.1039/C5CS00462D
Cui Y, Xu Z, Li HY, Young DJ, Ren ZG, Li HX (2020) Synthesis of a pyrazole-based microporous organic polymer for high-performance CO2 capture and alkyne carboxylation. ACS Appl Polym Mater 2:4512–4520. https://doi.org/10.1021/acsapm.0c00592
Das S, Mondal P, Ghosh S, Satpati B, Deka S, Islam SM, Bala T (2018) A facile synthesis strategy to couple porous nanocubes of CeO2 with Ag nanoparticles: an excellent catalyst with enhanced reactivity for the ‘click reaction’ and carboxylation of terminal alkynes. New J Chem 42:7314–7325. https://doi.org/10.1039/C8NJ00665B
Elhamifar D, Khanmohammadi H, Elhamifar D (2017) Nickel containing ionic liquid based ordered nanoporous organosilica: a powerful and recoverable catalyst for synthesis of polyhydroquinolines. RSC Adv 7:54789–54796. https://doi.org/10.1039/c7ra10758g
Esquivel D, Amaro-Gahete J, Caballero-Casero N, Jiménez-Sanchidrián C, Ruiz JR, Rubio S, Voort PVD, Romero-Salguero FJ (2020) Tailoring bifunctional periodic mesoporous organosilicas for cooperative catalysis. ACS Appl Nano Mater 3:2373–2382. https://doi.org/10.1021/acsanm.9b02493
Feng L, Li X, Liu B, Vessally E (2020) Hydrocarboxylation of alkynes utilizing CO2 as C1 synthon: A facile and environmentally benign access to α, β-unsaturated carboxylic acids. J CO2 Util 40:101220. https://doi.org/10.1016/j.jcou.2020.101220
Guo L, Lamb KJ, North M (2021) Recent developments in organocatalysed transformations of epoxides and carbon dioxide into cyclic carbonates. Green Chem 23:77–118. https://doi.org/10.1039/D0GC03465G
Guo S, Asset T, Atanassov P (2021) Catalytic hybrid electrocatalytic/biocatalytic cascades for carbon dioxide reduction and valorization. ACS Catal 11:5172–5188. https://doi.org/10.1021/acscatal.0c04862
Ho HJ, Iizuka A, Shibata E (2019) Carbon capture and utilization technology without carbon dioxide purification and pressurization: a review on its necessity and available technologies. Ind Eng Chem Res 58:8941–8954. https://doi.org/10.1021/acs.iecr.9b01213
Jiang Y, Li B, Qu X, Cheng Y (2016) A green vendor-managed inventory analysis in supply chains under carbon emissions trading mechanism. Clean Techn Environ Policy 18:1369–1380. https://doi.org/10.1007/s10098-015-1048-0
Jiang X, Nie X, Guo X, Song C, Chen JG (2020) Recent advances in carbon dioxide hydrogenation to methanol via heterogeneous catalysis. Chem Rev 120:7984–8034. https://doi.org/10.1021/acs.chemrev.9b00723
Karimi B, Mirzaei HM, Mobaraki A (2012) Periodic mesoporous organosilica functionalized sulfonic acids as highly efficient and recyclable catalysts in biodiesel production. Catal Sci Technol 2:828–834. https://doi.org/10.1039/C2CY00444E
Karimi B, Bigdeli A, Safari AA, Khorasani M, Vali H, Karimvand SK (2020) Aerobic oxidation of alcohols catalyzed by in situ generated gold nanoparticles inside the channels of periodic mesoporous organosilica with ionic liquid framework. ACS Comb Sci 22:70–79. https://doi.org/10.1021/acscombsci.9b00160
Kukawka R, Pawlowska-Zygarowicz A, Dzialkowska J, Pietrowski M, Maciejewski H, Bica K, Smiglak M (2019) Highly effective supported ionic liquid-phase (SILP) catalysts: characterization and application to the hydrosilylation reaction. ACS Sustain Chem Eng 7:4699–4706. https://doi.org/10.1021/acssuschemeng.8b04357
Lanaridi O, Sahoo AR, Limbeck A, Naghdi S, Eder D, Eitenberger E, Csendes Z, Schnürch M, Bica-Schröder K (2021) Toward the recovery of platinum group metals from a spent automotive catalyst with supported ionic liquid phases. ACS Sustain Chem Eng 9:375–386. https://doi.org/10.1021/acssuschemeng.0c07384
Li HR, He LN (2020) Construction of C-Cu bond: A useful strategy in CO2 conversion. Organometallics 39:1461–1475. https://doi.org/10.1021/acs.organomet.9b00642
Li S, Sun J, Zhang Z, Xie R, Fang X, Zhou M (2016) Carboxylation of terminal alkynes with CO2 using novel silver N-heterocyclic carbene complexes. Dalton Trans 45:10577–10584. https://doi.org/10.1039/C6DT01746K
Li H, Shen D, Lu H, Wu F, Chen X, Pleixats R, Pan J (2021) The synthetic approaches, properties, classification and heavy metal adsorption applications of periodic mesoporous organosilicas. Sep Purif Technol 277:119453. https://doi.org/10.1016/j.seppur.2021.119453
Liu J, Zhang X, Wen B, Li Y, Wu J, Wang Z, Wu T, Zhao R, Yang S (2021) Pre-carbonized nitrogen-rich polytriazines for the controlled growth of silver nanoparticles: catalysts for enhanced CO2 chemical conversion at atmospheric pressure. Catal Sci Technol 11:3119–3127. https://doi.org/10.1039/D0CY02473B
McNeice P, Marr PC, Marr AC (2021) Basic ionic liquids for catalysis: the road to greater stability. Catal Sci Technol 11:726–741. https://doi.org/10.1039/D0CY02274H
Modak A, Bhanja P, Bhaumik A (2018) Microporous nanotubes and nanospheres with iron-catechol sites: efficient lewis acid catalystand support for Ag nanoparticles in CO2 fixation reaction. Chem Eur J24:14189–14197. https://doi.org/10.1002/chem.201802319
Mota-Martinez MT, Brandl P, Hallett JP, Dowell NM (2018) Challenges and opportunities for the utilisation of ionic liquids as solvents for CO2 capture. Mol Syst Des Eng 3:560–571. https://doi.org/10.1039/C8ME00009C
Osman AI, Hefny M, Maksoud MIAA, Elgarahy AM, Rooney DW (2021) Recent advances in carbon capture storage and utilisation technologies: a review. Environ Chem Lett 19:797–849. https://doi.org/10.1007/s10311-020-01133-3
Otero M, Coimbra RN (2021) Current trends and perspectives in the application of polymeric materials for wastewater treatment. MDPI, St. Alban-Anlage 66, 4052 Basel, Switzerland. https://www.mdpi.com/journal/polymers/specialissues/currtrenpersapplpolymatewastrtreat
Owgi AHK, Jalil AA, Hussain I, Hassan NS, Hambali HU, Siang TJ, Vo4 DVN (2021) Catalytic systems for enhanced carbon dioxide reforming of methane: a review. Environ Chem Lett 19:2157–2183. https://doi.org/10.1007/s10311-020-01164-w
Pal N, Bhaumik A (2015) Mesoporous materials: versatile supports in heterogeneous catalysis for liquid phase catalytic transformations. RSC Adv 5:24363–24391. https://doi.org/10.1039/C4RA13077D
Quan Y, Yu R, Zhu J, Guan A, Lv X, Yang C, Li S, Wu J, Zheng G (2021) Efficient carboxylation of styrene and carbon dioxide by single-atomic copper electrocatalyst. J Colloid Interf Sci 601:378–384. https://doi.org/10.1016/j.jcis.2021.05.105
Rajabi F, Karimi N, Luque R, Voskressensky L (2021) Highly ordered mesoporous functionalized pyridinium protic ionic liquid framework as a highly efficient catalytic system in chemoselective thioacetalization of carbonyl compounds under solvent-free conditions. Mol Catal 515:111919. https://doi.org/10.1016/j.mcat.2021.111919
Ran CK, Liao LL, Gao TY, Gui YY, Yu DG (2021) Recent progress and challenges in carboxylation with CO2. Curr Opin Green Sustain Chem 32:100525. https://doi.org/10.1016/j.cogsc.2021.100525
Rebenstorf B, Andersson SLT (1990) Modified chromium/silica gel catalysts: impregnation of the silica gel with aluminium acetylacetonate and comparison with chromium on alumina (Alon-C) and SiO2. J Chem Soc Faraday Trans 86:3153–3158. https://doi.org/10.1039/FT9908603153
Ribeiro SO, Almeida PL, Pires J, Castro B, Balula SS (2020) Polyoxometalate@Periodic mesoporous organosilicas as active materials for oxidative desulfurization of diesels. Micropor Mesopor Mater 302:110193. https://doi.org/10.1016/j.micromeso.2020.110193
Riccobono A, Lazzara G, Rogers SE, Pibiri I, Pace A, Slattery JM, Bruce DW (2021) Synthesis and mesomorphism of related series of triphilic ionic liquid crystals based on 1,2,4-triazolium cations. J Mol Liq 321:114758. https://doi.org/10.1016/j.molliq.2020.114758
Sable DA, Vadagaonkar KS, Kapdi AR, Bhanage BM (2021) Carbon dioxide based methodologies for the synthesis of fine chemicals. Org Biomol Chem 19:5725–5757. https://doi.org/10.1039/D1OB00755F
Sharma H, Dhir A (2021) Capture of carbon dioxide using solid carbonaceous and non-carbonaceous adsorbents: a review. Environ Chem Lett 19:851–873. https://doi.org/10.1007/s10311-020-01118-2
Singh D, Gardas RL (2018) Influence of N-1 alkyl substituent on apparent molar properties of 1,2,4-triazolium based ionic liquids in aqueous solutions. J Mol Liq 250:477–484. https://doi.org/10.1016/j.molliq.2017.12.024
Sun L, Wang M, Li W, Luo S, Wu Y, Ma C, Liu S (2020) Carbon material–immobilized ionic liquids were applied on absorption of Hg2+ from water phase. Environ Sci Pollut Res 27:26882–26904. https://doi.org/10.1007/s11356-020-09054-y
Tomé LC, Marrucho IM (2016) Ionic liquid-based materials: a platform to design engineered CO2 separation membranes. Chem Soc Rev 45:2785–2824. https://doi.org/10.1039/C5CS00510H
Voort PVD, Esquivel D, Canck ED, Goethals F, Driessche IV, Romero-Salguero FJ (2013) Periodic Mesoporous Organosilicas: from simple to complex bridges; a comprehensive overview of functions, morphologies and applications. Chem Soc Rev 42:3913–3955. https://doi.org/10.1039/C2CS35222B
Wang F, Xu Q, Tan Z, Qian D, Ding Y, Li L, Li S, Li Y (2012) Alcohol soluble titanium(IV) oxide bis(2,4-pentanedionate) as electron collection layer for efficient inverted polymer solar cells. Org Electron 13:2429–2435. https://doi.org/10.1016/j.orgel.2012.07.005
Wang S, Yang X, Bai Q, Li T (2013) Ferric acetylacetonate catalyst on the urethane reaction of phenyl isocyanate and 1,2-propyleneglycol: a study of kinetics, thermodynamics, and mechanism with in situ FT-IR spectroscopy. Int J Polym Anal Charact 18:163–171. https://doi.org/10.1080/1023666X.2013.748146
Wang WH, Feng X, Sui K, Fang D, Bao M (2019) Transition metal-free carboxylation of terminal alkynes with carbon dioxide through dual activation: synthesis of propiolic acids. J CO2 Util 32:140–145. https://doi.org/10.1016/j.jcou.2019.04.011
Wolf P, Aubermann M, Wolf M, Bauer T, Blaumeiser D, Stepic R, Wick CR, Smith DM, Smith AS, Wasserscheid P, Libuda J, Haumann M (2019) Improving the performance of supported ionic liquid phase (SILP) catalysts for the ultra-low-temperature water-gas shift reaction using metal salt additives. Green Chem 21:5008–5018. https://doi.org/10.1039/C9GC02153A
Wu Z, Sun L, Liu Q, Yang X, Ye X, Hu Y, Huang Y (2017) A Schiff base-modified silver catalyst for efficient fixation of CO2 as carboxylic acid at ambient pressure. Green Chem 19:2080–2085. https://doi.org/10.1039/C7GC00923B
Xie JN, Yu B, Zhou ZH, Fu HC, Wang N, He LN (2015) Copper(I)-based ionic liquid-catalyzed carboxylation of terminal alkynes with CO2 at atmospheric pressure. Tetrahedron Lett 56:7059–7062. https://doi.org/10.1016/j.tetlet.2015.11.028
Yu B, Yang P, Gao X, Yang ZZ, Zhao YF, Zhang HY, Liu ZM (2017) CsF-promoted carboxylation of aryl(hetaryl) terminal alkynes with atmospheric CO2 at room temperature. New J Chem 41:9250–9255. https://doi.org/10.1039/C7NJ01779K
Zhang L, Bu R, Liu XY, Mu PF, Gao EQ (2021) Schiff-base molecules and COFs as metal-free catalysts or silver supports for carboxylation of alkynes with CO2. Green Chem 23:7620–7629. https://doi.org/10.1039/D1GC02118D
Zhang Y, Yang DH, Qiao S, Han BH (2021) Synergistic catalysis of ionic liquid-decorated covalent organic frameworks with polyoxometalates for CO2 cycloaddition reaction under mild conditions. Langmuir 37:10330–10339. https://doi.org/10.1021/acs.langmuir.1c01426
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This work was financially supported by the Research Foundation of Yichang Science and Technology Bureau (A21-3–009), 111 Project (D20015), the Research Fund for Excellent Dissertation of China Three Gorges University (2021SSPY049), and the Natural Science Foundation of Jiangxi Province of China (No. 20202BABL203023).
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Jing Rui Li: Investigation, data curation, formal analysis, and writing-original draft; Chen Chen: formal analysis and investigation; Xiao Bing Liu: funding acquisition, resources, and editing; Yu-Lin Hu: conceptualization, methodology, resources, supervision, writing-review and editing, and funding acquisition.
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Li, JR., Chen, C., Liu, XB. et al. Novel and sustainable carboxylation of terminal alkynes and CO2 to alkynyl carboxylic acids using triazolium ionic liquid-modified PMO-supported transition metal acetylacetonate as effective cooperative catalysts. Environ Sci Pollut Res 29, 83247–83261 (2022). https://doi.org/10.1007/s11356-022-21630-y
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DOI: https://doi.org/10.1007/s11356-022-21630-y