A Novel and Green In Situ Strategy for the Synthesis of Metallophthalocyanines on Chitosan and Investigation Their Catalytic Activity in the CO2 Fixation

  • Mahmoud Borjian Boroujeni
  • Mohammad Sadegh Laeini
  • Mohammad Taghi Nazeri
  • Ahmad ShaabaniEmail author


In this work, a novel and green strategy for the in situ synthesis of metallophthalocyanines on chitosan (MPcs@CS; M=Cu, Ni, Co) in deep eutectic solvents (DESs) at 120 °C has been reported. The chemical and structural properties of the MPcs@CS were determined by scanning electron microscopy (SEM), energy-dispersive X-ray(EDS), X-ray powder diffraction (XRD), Fourier transformation infrared spectroscopy(FT-IR), thermogravimetric analysis(TGA) and flame atomic absorption spectroscopies(FAAS). This new MPcs@CS is a highly efficient, active and reusable catalyst for the synthesis of cyclic carbonates from promoting the reaction of CO2 with epoxides under mild reaction conditions (at 80 °C and 1 atm CO2 pressure) with good to excellent yield of products. The order of catalytic activity is CuPc@CS, CoPc@CS and NiPc@CS from the conversion, temperature and time point of view, respectively.

Graphical Abstract


Chitosan Metallophthalocyanine CO2 fixation Heterogeneous catalyst Deep eutectic solvent Cyclic carbonate 



We gratefully acknowledge financial support from the Catalyst Center of Excellence (CCE) of Shahid Beheshti University and from the Iran National Science Foundation (INSF).

Compliance with Ethical Standards

Conflict of interest

The authors declare no conflict of interest.

Supplementary material

10562_2019_2740_MOESM1_ESM.docx (3.8 mb)
Supplementary material 1 (DOCX 3912 KB)


  1. 1.
    Guibal E (2005) Prog Polym Sci 30(1):71CrossRefGoogle Scholar
  2. 2.
    Macquarrie DJ, Hardy JJE (2005) Ind Eng Chem Res 44(23):8499CrossRefGoogle Scholar
  3. 3.
    Calò V, Angelo N, Antonio M et al (2004) Organometallics 23(22):5154–5158CrossRefGoogle Scholar
  4. 4.
    Chtchigrovsky M, Primo A, Gonzalez P et al (2009) Angew Chem Int Ed 121(32):6030CrossRefGoogle Scholar
  5. 5.
    Baig RN, Varma RS (2013) Green Chem 15(7):1839CrossRefGoogle Scholar
  6. 6.
    Yang B, Mao Z, Zhu X, Wan Y et al (2015) Catal Commun 60:92CrossRefGoogle Scholar
  7. 7.
    Guo CC, Huang G, Zhang XB et al (2003) Appl Catal A 247(2):261–267CrossRefGoogle Scholar
  8. 8.
    Sorokin AB (2013) Chem Rev 113(10):8152CrossRefGoogle Scholar
  9. 9.
    Levitsky IA, Euler WB, Tokranova N et al (2004) Appl Phys Lett 85(25):6245CrossRefGoogle Scholar
  10. 10.
    Bonnett R (1995) Chem Soc Rev 24(1):19CrossRefGoogle Scholar
  11. 11.
    Gregory P (2000) J Porphyrins Phthalocyanines 4(4):432CrossRefGoogle Scholar
  12. 12.
    Torre G, Claessens CG, Torres T (2007) Chem Commun 20:2000CrossRefGoogle Scholar
  13. 13.
    Sharma VB, Jain SL, Sain B (2004) Catal Lett. 94:57CrossRefGoogle Scholar
  14. 14.
    Dumoulin F, Durmus M, Ahsen V et al (2010) Coordin Chem Rev 254(23):2792CrossRefGoogle Scholar
  15. 15.
    Ghani F, Kristen J, Riegler H (2012) J Chem Eng Data 57(2):39CrossRefGoogle Scholar
  16. 16.
    Ragoussi ME, Torres T (2014) Chem Asian J 9:2676CrossRefGoogle Scholar
  17. 17.
    Sorokin AB, Quignard F, Valentin R et al (2006) Appl Catal A 309(2):162CrossRefGoogle Scholar
  18. 18.
    Li B, Zhang Y, Dingxuan M et al (2014) J Am Chem Soc 136(4):1202CrossRefGoogle Scholar
  19. 19.
    Zalomaeva OV, Kovalenko KA, Chesalov YA et al (2011) Dalton Trans 40(7):1441CrossRefGoogle Scholar
  20. 20.
    Joseph JK, Jain SL, Sain B (2010) Ind Eng Chem Res 49(14):6674CrossRefGoogle Scholar
  21. 21.
    Chauhan P, Yan N (2015) RSC Adv 5(47):37517CrossRefGoogle Scholar
  22. 22.
    Sakakura T, Choi JC, Yasuda H (2007) Chem Rev 107(6):2365CrossRefGoogle Scholar
  23. 23.
    Tomishige K, Yasuda H, Yoshida Y et al (2004) Green Chem 6(4):206CrossRefGoogle Scholar
  24. 24.
    Lu XB, Darensbourg DJ (2012) Chem Soc Rev 41(4):1462CrossRefGoogle Scholar
  25. 25.
    Suriano F, Pratt R, Tan JP et al (2010) Biomaterials 31(9):2637CrossRefGoogle Scholar
  26. 26.
    Petrowsky M, Ismail M, Glatzhofer DT, Frech R (2013) J Phys Chem B 117(19):5963CrossRefGoogle Scholar
  27. 27.
    Zhang H, Grinstaff MW (2013) J Am Chem Soc 135(18):6806CrossRefGoogle Scholar
  28. 28.
    Takahashi T, Watahiki T, Kitazume S et al (2006) Chem Commun 0(15):1664CrossRefGoogle Scholar
  29. 29.
    Srivastava R, Srinivas D, Ratnasamy P (2003) Catal Lett 89(1–2):81CrossRefGoogle Scholar
  30. 30.
    Ren Y, Chen J, Qi C, Jiang H (2015) ChemCatChem 7(10):1535CrossRefGoogle Scholar
  31. 31.
    Lu XB, Wang H, He R (2002) J Mol Catal A Chem 186(1–2):33CrossRefGoogle Scholar
  32. 32.
    Shaabani A, Keshipour S, Hamidzad M, Shaabani S (2014) J Mol Catal A Chem 395:494CrossRefGoogle Scholar
  33. 33.
    Mahyari M, Laeini MS, Shaabani A (2014) Chem Commun 50(58):7855CrossRefGoogle Scholar
  34. 34.
    Boroujeni MB, Hashemzadeh A, Shaabani A et al (2017) Appl Organomet Chem 31(10):3715CrossRefGoogle Scholar
  35. 35.
    Shaabani A, Boroujeni MB, Laeini MS (2016) RSC Adv 6(33):27706CrossRefGoogle Scholar
  36. 36.
    Shaabani A, Hooshmand SE, Afshari R et al (2018) J Solid State Chem 258:536CrossRefGoogle Scholar
  37. 37.
    Yang Y, Cui J, Zheng M et al (2012) Chem Commun 48(3):380CrossRefGoogle Scholar
  38. 38.
    Hassan AK, Gould RD (1992) Phys status solidi A 132(1):91CrossRefGoogle Scholar
  39. 39.
    Kyzas GZ, Bikiaris DN (2015) Mar Drugs 13(1):312CrossRefGoogle Scholar
  40. 40.
    Vieira RS, Guibal E, Silva EA, Beppu MM (2007) Adsorption 13(5–6):603CrossRefGoogle Scholar
  41. 41.
    Gordan OD, Friedrich M, Zahn DRT (2004) Org Electron 5(6):291CrossRefGoogle Scholar
  42. 42.
    Seelan S, Sinha AK, Srinivas et al (2000) J Mol Catal A Chem 157(1–2):163CrossRefGoogle Scholar
  43. 43.
    Zhao Y, Tian JS, Qi XH et al (2007) J Mol Catal A Chem 271(1–2):284CrossRefGoogle Scholar
  44. 44.
    Sun J, Wang J, Cheng W et al (2012) Green Chem 14(3):654CrossRefGoogle Scholar
  45. 45.
    Zhang T, Wang X, Huang X et al (2016) RSC Adv 6(4):2810CrossRefGoogle Scholar

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© Springer Science+Business Media, LLC, part of Springer Nature 2019

Authors and Affiliations

  1. 1.Faculty of ChemistryShahid Beheshti University, G. CTehranIran

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