Abstract
Global warming and climate change concerns are triggering worldwide interest for sustainable transformation of CO2 into useful chemicals. Here, a new and efficient multifunctional catalytic system for the cycloaddition of carbon dioxide with epoxides to synthesize cyclic carbonates under mild and solvent-free reaction conditions has been developed. The catalytic tests revealed that [P12,4,4,4]Br/MIL-53(Cr) (MIL: Materials of Institut Lavoisier) was the best and powerful catalytic system in the cycloaddition with excellent yields (96–99%) under solvent-free condition and 100 °C, 1.0 MPa for 2–3 h. The synergistic effect of anion and cation of ionic liquid [P12,4,4,4]Br as well as the chromium site of cocatalyst MIL-53(Cr) contributed to the excellent catalytic activity. The present catalytic system has several unique features such as simple operation, good to excellent yields, high catalytic activity, environmentally benign and safe. This study provides a sustainable and efficient synergistic strategy for chemical carbon dioxide fixation via the combination of ionic liquids and metal–organic frameworks.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Alves M, Grignard B, Gennen S, Detrembleur C, Jerome C, Tassaing T (2015) Organocatalytic synthesis of bio-based cyclic carbonates from CO2 and vegetable oils. RSC Adv 5:53629–53636. https://doi.org/10.1039/c5ra10190e
Alves M, Grignard B, Mereau R, Jerome C, Tassaing T, Detrembleur C (2017) Organocatalyzed coupling of carbon dioxide with epoxides for the synthesis of cyclic carbonates: catalyst design and mechanistic studies. Catal Sci Technol 7:2651–2684. https://doi.org/10.1039/c7cy00438a
Arayachukiat S, Kongtes C, Barthel A, Vummaleti SVC, Poater A, Wannakao S, Cavallo L, D’Elia V (2017) Ascorbic acid as a bifunctional hydrogen bond donor for the synthesis of cyclic carbonates from CO2 under ambient conditions. ACS Sustain Chem Eng 5:6392–6397. https://doi.org/10.1021/acssuschemeng.7b01650
Arshadi S, Vessally E, Hosseinian A, Soleimani-amiri S, Edjlali L (2017) Three-component coupling of CO2, propargyl alcohols, and amines: an environmentally benign access to cyclic and acyclic carbamates (a review). J CO2 Util 21:108–118. https://doi.org/10.1016/j.jcou.2017.07.008
Bellina F, Chiappe C, Lessi M (2012) Synthesis and properties of trialkyl(2,3-dihydroxypropyl) phosphonium salts, a new class of hydrophilic and hydrophobic glyceryl-functionalized ILs. Green Chem 14:148–155. https://doi.org/10.1039/c1gc16035d
Carena L, Vione D (2016) Photochemical reaction of peroxynitrite and carbon dioxide could account for up to 15% of carbonate radicals generation in surface waters. Environ Chem Lett 14:183–187. https://doi.org/10.1007/s10311-016-0549-3
Chaterjee S, Krupadam RJ (2018) Amino acid-imprinted polymers as highly selective CO2 capture materials. Environ Chem Lett. https://doi.org/10.1007/s10311-018-0774-z
Chen Y, Luo R, Xu Q, Zhang W, Zhou X, Ji H (2017) State of the art aluminum porphyrin-based heterogeneous catalysts for the chemical fixation of CO2 into cyclic carbonates at ambient conditions. Chem Cat Chem 9:767–773. https://doi.org/10.1002/cctc.201601578
Costa SPF, Azevedo AMO, Pinto PCAG, Saraiva MLMFS (2017) Environmental impact of ionic liquids: recent advances in (eco)toxicology and (bio)degradability. ChemSusChem 10:2321–2347. https://doi.org/10.1002/cssc.201700261
Dai W, Zhang Y, Tan Y, Luo X, Tu X (2016) Reusable and efficient polymer nanoparticles grafted with hydroxyl-functionalized phosphonium-based ionic liquid catalyst for cycloaddition of CO2 with epoxides. Appl Catal A Gen 514:43–50. https://doi.org/10.1016/j.apcata.2016.01.004
Ding LG, Yao B, Jiang WL, Li JT, Fu QJ, Li YA, Liu ZH, Ma JP, Dong YB (2017) Bifunctional imidazolium-based ionic liquid decorated UiO-67 type MOF for selective CO2 adsorption and catalytic property for CO2 cycloaddition with epoxides. Inorg Chem 56:2337–2344. https://doi.org/10.1021/acs.inorgchem.6b03169
Fiorani G, Guo W, Kleij AW (2015) Sustainable conversion of carbon dioxide: the advent of organocatalysis. Green Chem 17:1375–1389. https://doi.org/10.1039/c4gc01959h
Gennen S, Alves M, Méreau R, Tassaing T, Gilbert B, Detrembleur C, Jerome C, Grignard B (2015) Fluorinated alcohols as activators for the solvent-free chemical fixation of carbon dioxide into epoxides. Chemsuschem 8:1845–1849. https://doi.org/10.1002/cssc.201500103
He H, Perman JA, Zhu G, Ma S (2016) Metal-organic frameworks for CO2 chemical transformations. Small 12:6309–6324. https://doi.org/10.1002/smll.201602711
Ju HY, Manju MD, Kim KH, Park SW, Park DW (2008) Catalytic performance of quaternary ammonium salts in the reaction of butyl glycidyl ether and carbon dioxide. J Ind Eng Chem 14:157–160. https://doi.org/10.1016/j.jiec.2007.12.001
Kaneko S, Shirakawa S (2017) Potassium iodide–tetraethylene glycol complex as a practical catalyst for CO2 fixation reactions with epoxides under mild conditions. ACS Sustain Chem Eng 5:2836–2840. https://doi.org/10.1021/acssuschemeng.7b00324
Kaneti YV, Tang J, Salunkhe RR, Jiang X, Yu A, Wu KCW, Yamauchi Y (2017) Nanoarchitectured design of porous materials and nanocomposites from metal–organic frameworks. Adv Mater 29:1604898. https://doi.org/10.1002/adma.201604898
Kelly MJ, Barthel A, Maheu C, Sodpiban O, Dega FB, Vummaleti SVC, Abou-Hamad E, Pelletier JDA, Cavallo L, D’Elia V, Basset JM (2017) Conversion of actual flue gas CO2 via cycloaddition to propylene oxide catalyzed by a single-site, recyclable zirconium catalyst. J CO2 Util 20:243–252. https://doi.org/10.1016/j.jcou.2017.05.020
Khatun R, Bhanja P, Mondal P, Bhaumik A, Das D, Islam SM (2017) Palladium nanoparticles embedded over mesoporous TiO2 for chemical fixation of CO2 under atmospheric pressure and solvent-free conditions. New J Chem 41:12937–12946. https://doi.org/10.1039/c7nj02459b
Kumar P, Faujdar E, Singh RK, Paul S, Kukrety A, Chhibber VK, Ray SS (2018) High CO2 absorption of O-carboxymethylchitosan synthesised from chitosan. Environ Chem Lett. https://doi.org/10.1007/s10311-018-0713-z
Lais A, Gondal MA, Dastageer MA (2018) Semiconducting oxide photocatalysts for reduction of CO2 to methanol. Environ Chem Lett 16:183–210. https://doi.org/10.1007/s10311-017-0673-8
Lan DH, Yang FM, Luo SL, Au CT, Yin SF (2014) Water-tolerant graphene oxide as a high-efficiency catalyst for the synthesis of propylene carbonate from propylene oxide and carbon dioxide. Carbon 73:351–360. https://doi.org/10.1016/j.carbon.2014.02.075
Lan DH, Chen L, Au CT, Yin SF (2015) One-pot synthesized multi-functional grapheme oxide as a water-tolerant and efficient metal-free heterogeneous catalyst for cycloaddition reaction. Carbon 93:22–31. https://doi.org/10.1016/j.carbon.2015.05.023
Lan DH, Fan N, Wang Y, Gao X, Zhang P, Chen L, Au CT, Yin SF (2016a) Recent advances in metal-free catalysts for the synthesis of cyclic carbonates from CO2 and epoxides. Chin J Catal 37:826–845. https://doi.org/10.1016/s1872-2067(15)61085-3
Lan DH, Wang HT, Chen L, Au CT, Yin SF (2016b) Phosphorous-modified bulk graphitic carbon nitride: facile preparation and application as an acid-base bifunctional and efficient catalyst for CO2 cycloaddition with epoxides. Carbon 100:81–89. https://doi.org/10.1016/j.carbon.2015.12.098
Lan DH, Gong YX, Tan NY, Wu SS, Shen J, Yao KC, Yi B, Au CT, Yin SF (2018) Multi-functionalization of GO with multi-cationic ILs as high efficient metal-free catalyst for CO2 cycloaddition under mild conditions. Carbon 127:245–254. https://doi.org/10.1016/j.carbon.2017.11.007
Liu S, Zhang Y, Jiang H, Wang X, Zhang T, Yao Y (2018) High CO2 adsorption by amino-modified bio-spherical cellulose nanofibres aerogels. Environ Chem Lett 16:605–614. https://doi.org/10.1007/s10311-017-0701-8
Martín C, Fiorani G, Kleij AW (2015) Recent advances in the catalytic preparation of cyclic organic carbonates. ACS Catal 5:1353–1370. https://doi.org/10.1021/cs5018997
Montoya CA, Gómez CF, Paninho AB, Nunes AVM, Mahmudov KT, Najdanovic-Visak V, Martins LMDRS, da Silva MFCG, Pombeiro AJL, da Ponte MN (2016) Cyclic carbonate synthesis from CO2 and epoxides using zinc(II) complexes of arylhydrazones of β-diketones. J Catal 335:135–140. https://doi.org/10.1016/j.jcat.2015.12.027
Nandigama SK, Bheeram VR, Mukkamala SB (2018) Rapid synthesis of mono/bimetallic (Zn/Co/Zn–Co) zeolitic imidazolate frameworks at room temperature and evolution of their CO2 uptake capacity. Environ Chem Lett. https://doi.org/10.1007/s10311-018-0775-y
Qiu J, Zhao Y, Li Z, Wang H, Fan M, Wang J (2017) Efficient ionic liquid promoted chemical fixation of CO2 into α-alkylidene cyclic carbonates. Chemsuschem 10:1120–1127. https://doi.org/10.1002/cssc.201601129
Rojas MF, Bernard FL, Aquino A, Borges J, Vecchia FD, Menezes S, Ligabue R, Einloft S (2014) Poly(ionic liquid)s as efficient catalyst in transformation of CO2 to cyclic carbonate. J Mol Catal A Chem 392:83–88. https://doi.org/10.1016/j.molcata.2014.05.007
Rubio-Martinez M, Avci-Camur C, Thornton AW, Imaz I, Maspoch D, Hill MR (2017) New synthetic routes towards MOF production at scale. Chem Soc Rev 46:3453–3480. https://doi.org/10.1039/c7cs00109f
Seo UR, Chung YK (2014) Poly(4-vinylimidazolium)s/diazabicyclo[5.4.0]undec-7-ene/Zinc(II) bromide catalyzed cycloaddition of carbon dioxide to epoxides. Adv Synth Catal 356:1955–1961. https://doi.org/10.1002/adsc.201400047
Sharifi A, Abaee MS, Mokhtare Z, Mirzaei M (2014) Room temperature synthesis of 2H-1,4-benzoxazine derivatives using a recoverable ionic liquid medium. Environ Chem Lett 12:365–370. https://doi.org/10.1007/s10311-014-0456-4
Sołtys-Brzostek K, Terlecki M, Sokołowski K, Lewiński J (2017) Chemical fixation and conversion of CO2 into cyclic and cage-type metal carbonates. Coord Chem Rev 334:199–231. https://doi.org/10.1016/j.ccr.2016.10.008
Sopeña S, Martin E, Escudero-Adán EC, Kleij AW (2017) Pushing the limits with squaramide-based organocatalysts in cyclic carbonate synthesis. ACS Catal 7:3532–3539. https://doi.org/10.1021/acscatal.7b00475
Tian D, Liu B, Gan Q, Li H, Darensbourg DJ (2012) Formation of cyclic carbonates from carbon dioxide and epoxides coupling reactions efficiently catalyzed by robust, recyclable one-component aluminum-salen complexes. ACS Catal 2:2029–2035. https://doi.org/10.1021/cs300462r
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
Wang J, Zhang Y (2016) Boronic acids as hydrogen bond donor catalysts for efficient conversion of CO2 into organic carbonate in water. ACS Catal 6:4871–4876. https://doi.org/10.1021/acscatal.6b01422
Whiteoak CJ, Nova A, Maseras F, Kleij AW (2012) Merging sustainability with organocatalysis in the formation of organic carbonates by using CO2 as a feedstock. Chemsuschem 5:2032–2038. https://doi.org/10.1002/cssc.201200255
Zhang H, Liu R, Lal R (2016) Optimal sequestration of carbon dioxide and phosphorus in soils by gypsum amendment. Environ Chem Lett 14:443–448. https://doi.org/10.1007/s10311-016-0564-4
Zhou X, Zhang Y, Yang X, Yao J, Wang G (2010) Hydrated alkali metal halides as efficient catalysts for the synthesis of cyclic carbonates from CO2 and epoxides. Chin J Catal 31:765–768. https://doi.org/10.1016/s1872-2067(09)60086-3
Zhu J, Usov PM, Xu W, Celis-Salazar PJ, Lin S, Kessinger MC, Landaverde-Alvarado C, Cai M, May AM, Slebodnick C, Zhu D, Senanayake SD, Morris AJ (2018) A new class of metal-cyclam-based zirconium metal–organic frameworks for CO2 adsorption and chemical fixation. J Am Chem Soc 140:993–1003. https://doi.org/10.1021/jacs.7b10643
Acknowledgements
The authors are grateful to the National Natural Science Foundation of China (No. 21506115) for financial support of this research.
Author information
Authors and Affiliations
Corresponding author
Electronic supplementary material
Below is the link to the electronic supplementary material.
Rights and permissions
About this article
Cite this article
Hu, Y.L., Zhang, R.L. & Fang, D. Quaternary phosphonium cationic ionic liquid/porous metal–organic framework as an efficient catalytic system for cycloaddition of carbon dioxide into cyclic carbonates. Environ Chem Lett 17, 501–508 (2019). https://doi.org/10.1007/s10311-018-0793-9
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10311-018-0793-9