Advertisement

Harnessing CO2 into Carbonates Using Heterogeneous Waste Derivative Cellulose-Based Poly(ionic liquids) as Catalysts

  • Daniela M. Rodrigues
  • Luiza G. Hunter
  • Franciele L. Bernard
  • Marisol F. Rojas
  • Felipe Dalla Vecchia
  • Sandra EinloftEmail author
Article
  • 116 Downloads

Abstract

CO2 chemical transformation into chemicals is an interesting option to mitigate CO2 concentration in the atmosphere. CO2 is an important carbon source, non-toxic, non-flammable, abundant and renewable, making it an interesting raw material. In this work, cellulose-based poly(ionic liquids) (CPILs) was synthesized from cellulose extracted from rice husk, modified with citric acid and functionalized with different cations. CPILs were used as heterogeneous catalysts for CO2 chemical transformation into cyclic carbonates by cycloaddition of CO2 with epoxides [propylene (PO) and styrene oxides (SO)]. The effect of the cation present in CPILs in catalytic performance, use of ZnBr2 as a co-catalyst and catalytic reaction parameters (temperature, pressure and time) were investigated just as well. Results demonstrate that CPILs cation variation influence their catalytic activity. A higher CO2 yield and selectivity of 81.9%/95.3% for propylene carbonate (PC) and 78.7%/100% for styrene carbonate (SC) was obtained by CPIL-TBP/ZnBr2 at conditions of 40 bar, 110 °C and 6 h, being easily separated and recycled without significant loss of catalytic activity until the fourth cycle.

Graphical Abstract

Notes

Acknowledgements

This study was financed in part by the Coordenação de Aperfeiçoamento de Pessoal de Nivel Superior – Brasil (CAPES) – Finance Code 001. Sandra Einloft thanks CNPq for research scholarship.

References

  1. 1.
    Shukla JB, Verma M, Misra AK (2017) Effect of global warming on sea level rise: a modeling study. Ecol Complex 32:99–110.  https://doi.org/10.1016/j.ecocom.2017.10.007 CrossRefGoogle Scholar
  2. 2.
    Hussain A, Arif SM, Aslam M (2017) Emerging renewable and sustainable energy technologies: state of the art. Renew Sustain Energy Rev 71:12–28.  https://doi.org/10.1016/j.rser.2016.12.033 CrossRefGoogle Scholar
  3. 3.
    Styring P, Jansen D, de Coninck H et al (2011) Carbon capture and utilisation in the green economyGoogle Scholar
  4. 4.
    Saptal VB, Bhanage BM (2017) Current advances in heterogeneous catalysts for the synthesis of cyclic carbonates from carbon dioxide. Curr Opin Green Sustain Chem 3:1–10.  https://doi.org/10.1016/j.cogsc.2016.10.006 CrossRefGoogle Scholar
  5. 5.
    Dai WL, Luo SL, Yin SF, Au CT (2009) The direct transformation of carbon dioxide to organic carbonates over heterogeneous catalysts. Appl Catal A 366:2–12.  https://doi.org/10.1016/j.apcata.2009.06.045 CrossRefGoogle Scholar
  6. 6.
    Liu Q, Wu L, Jackstell R, Beller M (2015) Using carbon dioxide as a building block in organic synthesis. Nat Commun 6:1–15.  https://doi.org/10.1038/ncomms6933 CrossRefGoogle Scholar
  7. 7.
    Vessally E, Babazadeh M, Hosseinian A et al (2017) Nanocatalysts for chemical transformation of carbon dioxide. J CO2 Util 21:491–502.  https://doi.org/10.1016/j.jcou.2017.08.014 CrossRefGoogle Scholar
  8. 8.
    Chen F, Dong T, Chi Y et al (2010) Transition-metal-substituted keggin-type germanotungstates for catalytic conversion of carbon dioxide to cyclic carbonate. Catal Lett 139:38–41.  https://doi.org/10.1007/s10562-010-0394-0 CrossRefGoogle Scholar
  9. 9.
    Liu L, Wang SM, Han ZB et al (2016) Exceptionally robust in-based metal-organic framework for highly efficient carbon dioxide capture and conversion. Inorg Chem 55:3558–3565.  https://doi.org/10.1021/acs.inorgchem.6b00050 CrossRefPubMedGoogle Scholar
  10. 10.
    Sun J, Wang L, Zhang S et al (2006) ZnCl2/phosphonium halide: an efficient Lewis acid/base catalyst for the synthesis of cyclic carbonate. J Mol Catal A 256:295–300.  https://doi.org/10.1016/j.molcata.2006.05.004 CrossRefGoogle Scholar
  11. 11.
    Xiao L, Lv D, Wu W (2011) Brønsted acidic ionic liquids mediated metallic salts catalytic system for the chemical fixation of carbon dioxide to form cyclic carbonates. Catal Lett 141:1838–1844.  https://doi.org/10.1007/s10562-011-0682-3 CrossRefGoogle Scholar
  12. 12.
    Liang J, Chen RP, Wang XY et al (2017) Postsynthetic ionization of an imidazole-containing metal-organic framework for the cycloaddition of carbon dioxide and epoxides. Chem Sci 8:1570–1575.  https://doi.org/10.1039/c6sc04357g CrossRefPubMedGoogle Scholar
  13. 13.
    Kumar S, Jain SL, Sain B (2012) Metal acetylacetonates as highly efficient and cost effective catalysts for the synthesis of cyclic carbonates from CO2 and epoxides. Catal Lett 142:615–618.  https://doi.org/10.1007/s10562-012-0803-7 CrossRefGoogle Scholar
  14. 14.
    Aquino AS, Bernard FL, Vieira MO et al (2014) A new approach to CO2 capture and conversion using imidazolium based-ionic liquids as sorbent and catalyst. J Braz Chem Soc 25:2251–2257.  https://doi.org/10.5935/0103-5053.20140176 CrossRefGoogle Scholar
  15. 15.
    He Q, O’Brien JW, Kitselman KA et al (2014) Synthesis of cyclic carbonates from CO2 and epoxides using ionic liquids and related catalysts including choline chloride–metal halide mixtures. Catal Sci Technol 4:1513–1528.  https://doi.org/10.1039/C3CY00998J CrossRefGoogle Scholar
  16. 16.
    Kawanami H, Sasaki A, Matsui K, Ikushima Y (2003) A rapid and effective synthesis of propylene carbonate using a supercritical CO2–ionic liquid system. Chem Commun.  https://doi.org/10.1039/b212823c
  17. 17.
    Xu B-H, Wang J-Q, Sun J et al (2015) Fixation of CO2 into cyclic carbonates catalyzed by ionic liquids: a multi-scale approach. Green Chem 17:108–122.  https://doi.org/10.1039/C4GC01754D CrossRefGoogle Scholar
  18. 18.
    Bobbink FD, Dyson PJ (2016) Synthesis of carbonates and related compounds incorporating CO2 using ionic liquid-type catalysts: state-of-the-art and beyond. J Catal 343:52–61.  https://doi.org/10.1016/j.jcat.2016.02.033 CrossRefGoogle Scholar
  19. 19.
    Neto D, Brenno A, Spencer J (2012) The impressive chemistry, applications and features of ionic liquids: properties, catalysis & catalysts and trends. J Braz Chem Soc 23:987–1007.  https://doi.org/10.1590/S0103-50532012000600002 CrossRefGoogle Scholar
  20. 20.
    Hwang GY, Roshan R, Ryu HS et al (2016) A highly efficient zeolitic imidazolate framework catalyst for the co-catalyst and solvent free synthesis of cyclic carbonates from CO2. J CO2 Util 15:123–130.  https://doi.org/10.1016/j.jcou.2016.02.005 CrossRefGoogle Scholar
  21. 21.
    Yasuda H, He LN, Sakakura T (2002) Cyclic carbonate synthesis from supercritical carbon dioxide and epoxide over lanthanide oxychloride. J Catal 209:547–550.  https://doi.org/10.1006/jcat.2002.3662 CrossRefGoogle Scholar
  22. 22.
    Sun J, Cheng W, Fan W et al (2009) Reusable and efficient polymer-supported task-specific ionic liquid catalyst for cycloaddition of epoxide with CO2. Catal Today 148:361–367.  https://doi.org/10.1016/j.cattod.2009.07.070 CrossRefGoogle Scholar
  23. 23.
    Jagtap SR, Bhanushali MJ, Panda AG, Bhanage BM (2006) Synthesis of cyclic carbonates from carbon dioxide and epoxides using alkali metal halide supported liquid phase catalyst. Catal Lett 112:51–55.  https://doi.org/10.1007/s10562-006-0163-2 CrossRefGoogle Scholar
  24. 24.
    Zhang W, Wang Q, Wu H et al (2014) A highly ordered mesoporous polymer supported imidazolium-based ionic liquid: an efficient catalyst for cycloaddition of CO2 with epoxides to produce cyclic carbonates. Green Chem 16:4767–4774.  https://doi.org/10.1039/C4GC01245C CrossRefGoogle Scholar
  25. 25.
    Wang JQ, Yue XD, Cai F, He LN (2007) Solventless synthesis of cyclic carbonates from carbon dioxide and epoxides catalyzed by silica-supported ionic liquids under supercritical conditions. Catal Commun 8:167–172.  https://doi.org/10.1016/j.catcom.2006.05.049 CrossRefGoogle Scholar
  26. 26.
    Roshan KR, Mathai G, Kim J et al (2012) A biopolymer mediated efficient synthesis of cyclic carbonates from epoxides and carbon dioxide. Green Chem 14:2933–2940.  https://doi.org/10.1039/c2gc35942a CrossRefGoogle Scholar
  27. 27.
    Xiong Y, Bai F, Cui Z et al (2013) Cycloaddition reaction of carbon dioxide to epoxides catalyzed by polymer-supported quaternary phosphonium salts. J Chem 2013:1–9.  https://doi.org/10.1155/2013/261378 CrossRefGoogle Scholar
  28. 28.
    Meng X-L, Nie Y, Sun J et al (2014) Functionalized dicyandiamide–formaldehyde polymers as efficient heterogeneous catalysts for conversion of CO2 into organic carbonates. Green Chem 16:2771–2778.  https://doi.org/10.1039/C3GC42331J CrossRefGoogle Scholar
  29. 29.
    Xie Y, Zhang Z, Jiang T et al (2007) CO2 cycloaddition reactions catalyzed by an ionic liquid grafted onto a highly cross-linked polymer matrix. Angew Chem Int Ed 46:7255–7258.  https://doi.org/10.1002/anie.200701467 CrossRefGoogle Scholar
  30. 30.
    Wang J-Q, Sun J, Cheng W-G et al (2012) Experimental and theoretical studies on hydrogen bond-promoted fixation of carbon dioxide and epoxides in cyclic carbonates. Phys Chem Chem Phys 14:11021.  https://doi.org/10.1039/c2cp41698k CrossRefPubMedGoogle Scholar
  31. 31.
    Rojas MF, Bernard FL, Aquino A et al (2014) Poly(ionic liquid)s as efficient catalyst in transformation of CO2 to cyclic carbonate. J Mol Catal A 392:83–88.  https://doi.org/10.1016/j.molcata.2014.05.007 CrossRefGoogle Scholar
  32. 32.
    Yu B, Xie J-N, Zhong C-L et al (2015) Copper(I)@carbon-catalyzed carboxylation of terminal alkynes with CO2 at atmospheric pressure. ACS Catal 5:3940–3944.  https://doi.org/10.1021/acscatal.5b00764 CrossRefGoogle Scholar
  33. 33.
    Roshan KR, Jose T, Kathalikkattil AC et al (2013) Microwave synthesized quaternized celluloses for cyclic carbonate synthesis from carbon dioxide and epoxides. Appl Catal A 467:17–25.  https://doi.org/10.1016/j.apcata.2013.07.007 CrossRefGoogle Scholar
  34. 34.
    Linares N, Silvestre-Albero AM, Serrano E et al (2014) Mesoporous materials for clean energy technologies. Chem Soc Rev 43:7681–7717.  https://doi.org/10.1039/c3cs60435g CrossRefPubMedGoogle Scholar
  35. 35.
    Yuan J, Mecerreyes D, Antonietti M (2013) Poly(ionic liquid)s: an update. Prog Polym Sci 38:1009–1036.  https://doi.org/10.1016/j.progpolymsci.2013.04.002 CrossRefGoogle Scholar
  36. 36.
    Yuan J, Antonietti M (2011) Poly(ionic liquid)s: polymers expanding classical property profiles. Polymer 52:1469–1482.  https://doi.org/10.1016/j.polymer.2011.01.043 CrossRefGoogle Scholar
  37. 37.
    Lang X, He L (2016) Green catalytic process for cyclic carbonate synthesis from carbon dioxide under mild conditions. Chem Rec.  https://doi.org/10.1002/tcr.201500293
  38. 38.
    Bernard FL, Rodrigues DM, Polesso BB et al (2016) New cellulose based ionic compounds as low-cost sorbents for CO2 capture. Fuel Process Technol 149:131–138.  https://doi.org/10.1016/j.fuproc.2016.04.014 CrossRefGoogle Scholar
  39. 39.
    Shim JJ, Kim D, Choon SR (2006) Carboxylation of styrene oxide catalyzed by quaternary onium salts under solvent-free conditions. Bull Korean Chem Soc 27:744–746.  https://doi.org/10.5012/bkcs.2006.27.5.744 CrossRefGoogle Scholar
  40. 40.
    Wang JQ, Dong K, Cheng WG et al (2012) Insights into quaternary ammonium salts-catalyzed fixation carbon dioxide with epoxides. Catal Sci Technol 2:1480–1484.  https://doi.org/10.1039/c2cy20103h CrossRefGoogle Scholar
  41. 41.
    Chen Q, Peng C, Xie H et al (2015) Cellulosic poly(ionic liquid)s: synthesis, characterization and application in the cycloaddition of CO2 to epoxides. RSC Adv 5:44598–44603.  https://doi.org/10.1039/C5RA05667E CrossRefGoogle Scholar
  42. 42.
    Bernard FL, Polesso BB, Cobalchini FW et al (2017) Hybrid alkoxysilane-functionalized urethane-imide-based poly(ionic liquids) as a new platform for carbon dioxide capture. Energy Fuels 31:9840–9849.  https://doi.org/10.1021/acs.energyfuels.7b02027 CrossRefGoogle Scholar
  43. 43.
    Sun J, Fujita SI, Zhao F, Arai M (2004) Synthesis of styrene carbonate from styrene oxide and carbon dioxide in the presence of zinc bromide and ionic liquid under mild conditions. Green Chem 6:613–616.  https://doi.org/10.1039/b413229g CrossRefGoogle Scholar
  44. 44.
    Wu SS, Zhang XW, Dai WL et al (2008) ZnBr2-Ph4PI as highly efficient catalyst for cyclic carbonates synthesis from terminal epoxides and carbon dioxide. Appl Catal A 341:106–111.  https://doi.org/10.1016/j.apcata.2008.02.021 CrossRefGoogle Scholar
  45. 45.
    Shi TY, Wang JQ, Sun J, et al (2013) Efficient fixation of CO2 into cyclic carbonates catalyzed by hydroxyl-functionalized poly(ionic liquids). RSC Adv 3:3726–3732.  https://doi.org/10.1039/c3ra21872d CrossRefGoogle Scholar
  46. 46.
    Peng J, Deng Y (2001) Cycloaddition of carbon dioxide to propylene oxide catalyzed by ionic liquids. New J Chem 25:639–641.  https://doi.org/10.1039/b008923k CrossRefGoogle Scholar
  47. 47.
    Yang ZZ, He LN, Miao CX, Chanfreau S (2010) Lewis basic ionic liquids-catalyzed conversion of carbon dioxide to cyclic carbonates. Adv Synth Catal 352:2233–2240.  https://doi.org/10.1002/adsc.201000239 CrossRefGoogle Scholar
  48. 48.
    Girard AL, Simon N, Zanatta M et al (2014) Insights on recyclable catalytic system composed of task-specific ionic liquids for the chemical fixation of carbon dioxide. Green Chem 16:2815–2825.  https://doi.org/10.1039/c4gc00127c CrossRefGoogle Scholar
  49. 49.
    Song QW, Zhou ZH, He LN (2017) Efficient, selective and sustainable catalysis of carbon dioxide. Green Chem 19:3707.  https://doi.org/10.1039/c7gc00199a CrossRefGoogle Scholar
  50. 50.
    Li F, Xiao L, Xia C, Hu B (2004) Chemical fixation of CO2 with highly efficient ZnCl2/[BMIm]Br catalyst system. Tetrahedron Lett 45:8307–8310.  https://doi.org/10.1016/j.tetlet.2004.09.074 CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media, LLC, part of Springer Nature 2018

Authors and Affiliations

  1. 1.Post-Graduation Program in Materials Engineering and TechnologyPontifical Catholic University of Rio Grande do Sul – PUCRSPorto AlegreBrazil
  2. 2.School of SciencePontifical Catholic University of Rio Grande do Sul – PUCRSPorto AlegreBrazil
  3. 3.School of TechnologyPontifical Catholic University of Rio Grande do Sul – PUCRSPorto AlegreBrazil
  4. 4.Institute of Petroleum and Natural Resources -Pontifical Catholic University of Rio Grande do Sul – PUCRSPorto AlegreBrazil
  5. 5.School of Chemistry, Faculty of ScienceUniversidad Industrial de SantanderBucaramangaColombia
  6. 6.School of Science and EngineeringUniversidad de los LlanosVillavicencioColombia

Personalised recommendations