Atmosferik basınçta imidazolyum tuzları ile CO2’nin halkalı karbonatlara dönüşümü

Emine Aytar

doi:10.17714/gumusfenbil.1108451

TR EN

Atmosferik basınçta imidazolyum tuzları ile CO2’nin halkalı karbonatlara dönüşümü

Öz

Küresel ısınmaya neden olan CO2 doğal olarak bol bulunan, ucuz, genellikle sentez reaksiyonları için yapı taşı olarak kullanılabilen, toksik olmayan karbon (C1) kaynağı ve katma değerli kimyasal olarak bilinen inert bir maddedir. Kinetik eylemsizliği ve termodinamik kararlılığı nedeniyle verimli kullanımı zor olan CO2'nin bir katalizör yardımı ile halkalı karbonatlara dönüşümü en umut verici olan çalışmalardır. Bu nedenle bu çalışmada, 1-bütil-3-metilimidazolyum iyodür ([Bmim]I) ve 1-bütil-3-metilimidazolyum hekzaflorofosfat ([Bmim]PF6) imidazolyum tuzları CO2'nin epoksitler ile halkalı karbonatlara dönüşümünde katalizör olarak kullanılmıştır. Hem yüksek basınç ve yüksek sıcaklık altında hem de atmosferik basınç altında halkalı karbonatlara dönüşüm çalışmaları gerçekleştirilmiştir. Otoklavda yüksek verim sağlayan iyonik sıvılar atmosferik ortamda da oldukça iyi sonuçlar vermiştir. Atmosferik ortamda sürenin (2 saat ve 24 saat) ve sıcaklığın (60 °C ve 100 °C) etkisi ile optimizasyon çalışmaları gerçekleştirilmiştir. İyonik sıvılar ile katalize edilen bu sürecin, CO2'nin atmosferik ortamda kimyasal dönüşümü için de umut verici olduğu belirlenmiştir.

Anahtar Kelimeler

Epoksit , Halkalı karbonat , Ilımlı koşullar , İyonik sıvılar , Karbon dioksit

Conversion of CO2 to cyclic carbonates by imidazolium salts at atmospheric pressure

Abstract

CO2, which causes global warming, is a naturally abundant, inexpensive, inert substance known as a non-toxic carbon (C1) source and value-added chemical, which can often be used as a building block for synthesis reactions. The conversion of CO2, which is difficult to use efficiently due to its kinetic inertia and thermodynamic stability, to cyclic carbonates with the help of a catalyst are the most promising studies. Therefore, in this study, 1-bütyl-3-methylimidazolium iodide ([Bmim]I) and 1-bütyl-3-methylimidazolium hexafluorophosphate ([Bmim]PF6) imidazolium salts were used as catalysts in the conversion of CO2 into cyclic carbonates with epoxides. Conversion studies to cyclic carbonates were carried out under both high pressure and high temperature and atmospheric pressure. Ionic liquids, which provide high efficiency in the autoclave, also gave very good results in the atmospheric ambient. Optimization studies were carried out with the effect of time (2 hours and 24 hours) and temperature (60 °C and 100 °C) in the atmospheric ambient. It has been determined that this process, catalyzed by ionic liquids, is also promising for the chemical conversion of CO2 in the atmospheric ambient.

Keywords

Epoxide , Cyclic carbonate , Mild conditions , Ionic liquids , Carbon dioxide

Kaynakça

Andrea, K. A., & Kerton, F. M. (2019). Triarylborane-catalyzed formation of cyclic organic carbonates and polycarbonates. Acs Catalysis, 9(3), 1799-1809. https://doi.org/10.1021/acscatal.8b04282.
Annual CO2 Data. (2021). https://www.co2.earth/annual-co2
Arakawa, H., Aresta, M., Armor, J. N., Barteau, M. A., Beckman, E. J., Bell, A.T., Bercaw, J. E., Creutz, C., Dinjus, E., Dixon, D. A., Domen, K., Dubois, D. L., Eckert, J., Fujita, E., Gibson, D. H., Goddard, W. A., Goodman, D. W., Keller, J., Kubas, G. J., Kung, H. H., Lyons, J. E., Manzer, L. E., Marks, T. J., Morokuma, K., Nicholas, K. N., Stults, B. R., & Tumas, W. (2001). Catalysis research of relevance to carbon management: progress, challenges, and opportunities. Chemical Reviews, 101(4), 953-996. https://doi.org/10.1021/cr000018s
Arayachukiat, S., Kongtes, C., Barthel, A., Vummaleti, S. V., Poater, A., Wannakao, S., & D’Elia, V. (2017). Ascorbic acid as a bifunctional hydrogen bond donor for the synthesis of cyclic carbonates from CO2 under ambient conditions. ACS Sustainable Chemistry & Engineering, 5(8), 6392-6397. https://doi.org/10.1021/acssuschemeng.7b01650
Aytar, E. (2013). İyonik sıvılar ve NN tipi Zn-katalizörleri varliğinda CO2’in organik ürünlere dönüşümü [Yüksek Lisans Tezi, Harran Üniversitesi Fen Bilimleri Enstitüsü].
Aytar, E. (2019). Konjuge NN kompleks bileşikleri ve katalitik uygulamaları [Doktora Tezi, Harran Üniversitesi Fen Bilimleri Enstitüsü].
Barthel, A., Saih, Y., Gimenez, M., Pelletier, J. D., Kühn, F. E., D'elia, V., & Basset, J. M. (2016). Highly integrated CO2 capture and conversion: direct synthesis of cyclic carbonates from industrial flue gas. Green Chemistry, 18(10), 3116-3123. https://doi.org/10.1039/C5GC03007B
Cokoja, M., Wilhelm, M. E., Anthofer, M. H., Herrmann, W. A., & Kühn, F. E. (2015). Synthesis of cyclic carbonates from epoxides and carbon dioxide by using organocatalysts. Chemistry Sustainability Energy Materials, 8(15), 2436-2454. https://doi.org/10.1002/cssc.201500161
Comerford, J. W., Ingram, I. D. V., North, M., & Wu, X. (2015). Sustainable metal-based catalysts for the synthesis of cyclic carbonates containing five-membered rings. Green Chemistry, 17, 1966–1987. https://doi.org/10.1039/C4GC01719F
Darensbourg, D. J., Bottarelli, P., & Andreatta, J. R. (2007). Further studies related to the copolymerization of cyclohexene oxide and carbon dioxide catalyzed by chromium schiff base complexes. crystal structures of two l-hydroxo-bridged schiff base dimers of chromium(III). Macromolecules, 40, 7727-7729. https://doi.org/10.1021/ic049182e

Darensbourg, D. J., Mackiewicz, R. M., Phelps, A. L., & Billodeaux, D. R. (2004). Copolymerization of CO2 and epoxides catalyzed by metal salen complexes. Accounts of Chemical Research, 37(11), 836-844. https://doi.org/10.1021/ar030240u
Fiorani, G., Guo, W., & Kleij, A. W. (2015). Sustainable conversion of carbon dioxide: the advent of organocatalysis. Green Chemistry, 17(3), 1375-1389. https://doi.org/10.1039/C4GC01959H
Kilic, A., Aytar, E., & Beyazsakal, L. (2021). A novel dopamine‐based boronate esters with the organic base as highly efficient, stable, and green catalysts for the conversion of CO2 with epoxides to cyclic carbonates. Energy Technology, 9(9), 2100478. https://dx.doi.org/10.1002/ente.202100478
Kılıç, A., Durgun, M., Aytar, E., & Yavuz R. (2018). The synthesis and investigation of different cobaloximines by spectroscopic methods. Journal of Organometallic Chemistry, 858, 78–88. https://dx.doi.org/10.1016/j.jorganchem.2018.01.029
Kılıc, A., Ulusoy, M., Aytar, E., & Durgun, M. (2015). Mono multinuclear cobaloxime and organocobaloxime catalyzed conversion of CO2 and epoxides to cyclic organic carbonates synthesis and characterization. Journal of Industrial and Engineering Chemistry, 24, 98-106. https://dx.doi.org/10.1016/j.jiec.2014.09.015
Kilic, A., Sobay, B., Aytar, E., & Söylemez, R. (2020). Synthesis and effective catalytic performance in cycloaddition reactions with CO2 of boronate esters versus N-heterocyclic carbene (NHC)-stabilized boronate esters. Sustainable Energy & Fuels, 4(11), 5682-5696. https://dx.doi.org/10.1039/d0se01189d
Li, C., Liu, F., Zhao, T., Gu, J., Chen, P., & Chen, T. (2021). Highly efficient CO2 fixation into cyclic carbonate by hydroxyl-functionalized protic ionic liquids at atmospheric pressure. Molecular Catalysis, 511, 111756. https://doi.org/10.1021/acsomega.1c05416
Li, B., Zhang, R., & Lu, X. B. (2007). Stereochemistry control of the alternating copolymerization of CO2 and propylene oxide catalyzed by SalenCrX complexes. Macromolecules, 40, 2303-2307. https://doi.org/10.1021/ma062735f
Lu, X. B., & Darensbourg, D. J. (2012). Cobalt catalysts for the coupling of CO2 and epoxides to provide polycarbonates and cyclic carbonates. Chemical Sociecty Reviews, 41, 1462–1484. https://doi.org/10.1039/C1CS15142H
Lu, X. B., Zhang, Y. J., Liang, B., X. Wang, & Li, H. (2004). Chemical fixation of carbon dioxide to cyclic carbonates under extremely mild conditions with highly active bifunctional catalysts. Journal of Molecular Catalysis A: Chemical, 210, 31-34. https://doi.org/10.1016/j.molcata.2003.09.010
Martin, C., Fiorani, G., & Kleij, A. W. (2015). Recent advances in the catalytic preparation of cyclic organic carbonates. ACS Catalysis, 5, 1353–1370. https://doi.org/10.1021/cs5018997
Mirabaud, A., Martinez, A., Bayard, F., Dutasta, J. P., & Dufaud, V. (2018). A new heterogeneous host–guest catalytic system as an eco-friendly approach for the synthesis of cyclic carbonates from CO2 and epoxides. New Journal of Chemistry, 42, 16863–16874. https://doi.org/10.1039/C8NJ03065K
Mujmule, R. B., & Kim, H. (2022). Efficient imidazolium ionic liquid as a tri-functional robust catalyst for chemical fixation of CO2 into cyclic carbonates. Journal of Environmental Management, 314, 115045. https://doi.org/10.1016/j.jenvman.2022.115045
Noyori, R., Jessop, P. G., & Ikariya, T. (1995). Homogeneous hydrogenation of carbon dioxide. Chemical Reviews, 95, 259-272. https://doi.org/10.1021/cr00034a001
Omae, I. (2006). Aspects of carbon dioxide utilization. Catalysis Today, 115, 33-52. https://doi.org/10.1016/j.cattod.2006.02.024
Paddock, R. L., & Nguyen, S. T. (2001). Chemical CO2 fixation: Cr(III) salen complexes as highly efficient catalysts for the coupling of CO2 and epoxide. Journal of the American Chemical Society, 123, 11498-11499. https://doi.org/10.1021/ja0164677
Peng, J., Yang, H. J., Wang, S., Ban, B., Wei, Z., Lei, B., & Guo, C. Y. (2018). Efficient solvent-free fixation of CO2 catalyzed by new recyclable bifunctional metal complexes. Journal of CO2 Utilization, 24, 1-9. https://doi.org/10.1016/j.jcou.2017.12.003
Sakakura, T., & Kohno, K. (2009). The synthesis of organic carbonates from carbon dioxide. Chemical Communications, (11), 1312-1330. https://doi.org/10.1039/B819997C
Stamp, L. M., Mang, S. A., Holmes, A. B., Knights, K. A., de Miguel, Y. R., & McConvey, I. F. (2001). Polymer supported chromium porphyrin as catalyst for polycarbonate formation in supercritical carbon dioxide. Chemical Communications, (23), 2502-2503. https://doi.org/10.1039/B107400H
Shaikh, A. A. G., & Sivaram, S. (1996). Organic carbonates. Chemical Reviews, 96, 951-976. https://doi.org/10.1021/cr950067i
Sogukomerogulları, H. G., Aytar, E., Ulusoy, M., Demir, S., Dege, N., Richeson, D. S., & Sönmez, M. (2018). Synthesis of complexes Fe, Co and Cu supported by “SNS” pincer ligands and their ability to catalytically form cyclic carbonates. Inorganica Chimica Acta, 471, 290-296. https://dx.doi.org/10.1016/j.ica.2017.11.007
Ulusoy, M., Çetinkaya, E., & Çetinkaya, B. (2009). Conversion of carbon dioxide to cyclic carbonates using diimine Ru(II) complexes as catalysts. Applied Organometallic Chemistry, 23, 68-74. https://doi.org/10.1002/aoc.1473
Yamaguchi, K., Ebitani, K., Yoshida, T., Yoshida, H., & Kaneda, K. (1999). Mg− Al mixed oxides as highly active acid− base catalysts for cycloaddition of carbon dioxide to epoxides. Journal of the American Chemical Society, 121(18), 4526-4527. https://doi.org/10.1021/ja9902165
Yang, Z. Z., Zhao, Y. N., & He, L. N. (2011). CO2 chemistry: task-specific ionic liquids for CO2 capture/activation and subsequent conversion. Rsc Advances, 1(4), 545-567. https://doi.org/10.1039/C1RA00307K
Zhang, Z., Gao, H., Wu, H., Qian, Y., Chen, L., & Chen, J. (2018). Chemical fixation of CO2 by using carbon material-grafted N-heterocyclic carbene silver and copper complexes. ACS Applied Nano Materials, 1, 6463–6476. https://doi.org/10.1021/acsanm.8b01679
Zhang, H., Kong, X., Cao, C., Pang, G., & Shi, Y. (2016). An efficient ternary catalyst ZnBr2/K2CO3/[Bmim] Br for chemical fixation of CO2 into cyclic carbonates at ambient conditions. Journal of CO2 Utilization, 14, 76-82. https://doi.org/10.1016/j.jcou.2016.03.001
Zhao H. (2006). Innovatıve applıcatıons of ıonıc lıquıds as “green” engıneerıng lıquıds. Chemical Engineering Communications. 193, 1660–1677. https://doi.org/10.1080/00986440600586537
Wang, J., & Zhang, Y. (2016). Boronic acids as hydrogen bond donor catalysts for efficient conversion of CO2 into organic carbonate in water. ACS Catalysis, 6(8), 4871-4876. https://doi.org/10.1021/acscatal.6b01422
Xu, B. H., Wang, J. Q., Sun, J., Huang, Y., Zhang, J. P., Zhang, X. P., & Zhang, S. J. (2015). Fixation of CO2 into cyclic carbonates catalyzed by ionic liquids: a multi-scale approach. Green Chemistry, 17(1), 108-122. https://doi.org/10.1039/C4GC01754D

Ayrıntılar

Birincil Dil

Türkçe

Konular

-

Bölüm

Araştırma Makalesi

Yazarlar

Emine Aytar ^*
0000-0001-7572-8088
Türkiye

Yayımlanma Tarihi

15 Temmuz 2022

Gönderilme Tarihi

25 Nisan 2022

Kabul Tarihi

1 Temmuz 2022

Yayımlandığı Sayı

Yıl 2022 Cilt: 12 Sayı: 3

DOI

https://doi.org/10.17714/gumusfenbil.1108451

IZ

https://izlik.org/JA68RW65NM

APA

Aytar, E. (2022). Atmosferik basınçta imidazolyum tuzları ile CO2’nin halkalı karbonatlara dönüşümü. Gümüşhane Üniversitesi Fen Bilimleri Dergisi, 12(3), 923-935. https://doi.org/10.17714/gumusfenbil.1108451

Cited By

An assessment of boron-doped nanotube TiO2 as effective catalysts for CO2 fixation with epoxide to form cyclic carbonates

Inorganic Chemistry Communications

https://doi.org/10.1016/j.inoche.2025.113909

e-ISSN: 2146-538X Yayın Modeli: Sürekli Yayın Atıf Dizinleri: TR Dizin , SCOPUS

Atmosferik basınçta imidazolyum tuzları ile CO2’nin halkalı karbonatlara dönüşümü

Öz

Anahtar Kelimeler

Conversion of CO2 to cyclic carbonates by imidazolium salts at atmospheric pressure

Abstract

Keywords

Kaynakça

Ayrıntılar

Birincil Dil

Konular

Bölüm

Yazarlar

Yayımlanma Tarihi

Gönderilme Tarihi

Kabul Tarihi

Yayımlandığı Sayı

DOI

IZ

Kaynak Göster

Cited By

An assessment of boron-doped nanotube TiO2 as effective catalysts for CO2 fixation with epoxide to form cyclic carbonates