Skip to main content
Log in

Homogenous Dual-Ligand Zinc Complex Catalysts for Chemical Fixation of CO2 to Propylene Carbonate

  • Published:
Catalysis Letters Aims and scope Submit manuscript

Abstract

Homogeneous dual-ligand zinc complex catalysts was developed for the synthesis of propylene carbonate (PC) through chemical fixation of CO2. It was found that among a number of various pK a N-donor ligands, the catalytic performance was enhanced dramatically and the corrosion of the reaction system was effectively inhibited when 1-methylimidazol (1MI) was used as the N-donor ligand, in which >90 % PC yield could be obtained under mild reaction conditions. The dual-ligand zinc complex catalysts were characterized by various spectroscopic techniques such as FT-IR and 1HNMR. X-ray crystallography showed that the Zn(II) atom was coordinated in tetrahedron geometry by three bromine atom, one 1MI nitrogen atom, and one crystallographically independent cation to give a 3D tetrahedron structure, which forms tetracoordinated complexes. The structure of the complex gives the reasons for the enhancement of the catalytic activity from the microscopic molecular structure point of an extremely long and therefore labile Zn–Br bond, the diversification of the bond angles, and the interplay between the steric hindrance, which have great influence on the interaction forces of Zn–Br.

Graphical Abstract

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Scheme 1
Scheme 2
Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7
Scheme 3

Similar content being viewed by others

References

  1. Sakakura T, Choi JC, Yasuda H (2007) Chem Rev 107:2365

    Article  CAS  Google Scholar 

  2. North M, Pasquale R, Young C (2010) Green Chem 12:1514

    Article  CAS  Google Scholar 

  3. Omae I (2012) Coord Chem Rev 256:1384

    Article  CAS  Google Scholar 

  4. Dai WL, Luo SL, Yin SF, Au CT (2009) Appl Catal A Gen 366:2

    Article  CAS  Google Scholar 

  5. Sakakura T, Kohno K (2009) Chem Commun 11:1312

    Article  Google Scholar 

  6. Clements JH (2003) Ind Eng Chem Res 42:663

    Article  CAS  Google Scholar 

  7. Darensbourg DJ, Holtcamp MW (1996) Coord Chem Rev 153:155

    Article  CAS  Google Scholar 

  8. Ratzenhofer M, Kisch H (1980) Angew Chem Int Ed 19:317

    Article  Google Scholar 

  9. Ratzenhofer M, Kisch H (1980) Angew Chem 92:303

    Article  CAS  Google Scholar 

  10. Gibson DH (1996) Chem Rev 96:2063

    Article  CAS  Google Scholar 

  11. Ulusoy M, Sahin O, Kilic A, Buyukgungor O (2011) Catal Lett 141:717

    Article  CAS  Google Scholar 

  12. Ema T, Miyazaki Y, Taniguchi T, Takada J (2013) Green Chem 15:2485

    Article  CAS  Google Scholar 

  13. Decortes A, Castilla AM, Kleij AW (2010) Angew Chem Int Ed 49:9822

    Article  CAS  Google Scholar 

  14. Ghosh A, Ramidi P, Pulla S, Sullivan S, Collom S, Gartia Y, Munshi P, Biris A, Noll B, Berry B (2010) Catal Lett 137:1

    Article  CAS  Google Scholar 

  15. Sun J, Han L, Cheng W, Wang J, Zhang X, Zhang S (2011) ChemSusChem 4:502

    Article  CAS  Google Scholar 

  16. He LN, Yasuda H, Sakakura T (2003) Green Chem 5:92

    Article  CAS  Google Scholar 

  17. Paddock RL, Nguyen ST (2001) J Am Chem Soc 123:11498

    Article  CAS  Google Scholar 

  18. Lu XB, Liang B, Zhang YJ, Tian YZ, Wang YM, Bai CX, Wang H, Zhang R (2004) J Am Chem Soc 126:3732

    Article  CAS  Google Scholar 

  19. Aida T, Inoue S (1983) J Am Chem Soc 105:1304

    Article  CAS  Google Scholar 

  20. Kim HS, Kim JJ, Lee BG, Jung OS, Jang HG, Kang SO (2000) Angew Chem 39:4096

    Article  CAS  Google Scholar 

  21. Zhang YY, Chen L, Yin SF, Luo SL, Au CT (2012) Catal Lett 142:1376

    Article  CAS  Google Scholar 

  22. Paddock RL, Nguyen ST (2004) Chem Commun 14:1622

    Article  Google Scholar 

  23. Calo V, Nacci A, Monopoli A, Fanizzi A (2002) Org Lett 4:2561

    Article  CAS  Google Scholar 

  24. Kawanami H, Sasaki A, Matsui K, Ikushima Y (2003) Chem Commun 7:896

    Article  Google Scholar 

  25. Decortes A, Martinez Belmonte M, Benet-Buchholz J, Kleij AW (2010) Chem Commun 46:4580

    Article  CAS  Google Scholar 

  26. Barkakaty B, Morino K, Sudo A, Endo T (2010) Green Chem 12:42

    Article  CAS  Google Scholar 

  27. Dharman MM, Yu JI, Ahn JY, Park DW (2009) Green Chem 11:1754

    Article  CAS  Google Scholar 

  28. Sun J, Fujita SI, Zhao F, Arai M (2005) Appl Catal A Gen 287:221

    Article  CAS  Google Scholar 

  29. Li F, Xia C, Xu L, Sun W, Chen G (2003) Chem Commun 16:2042

    Article  Google Scholar 

  30. Kim HS, Kim JJ, Kim H, Jang HG (2003) J Catal 220:44

    Article  CAS  Google Scholar 

  31. Li F, Xiao L, Xia C, Hu B (2004) Tetrahedron Lett 45:8307

    Article  CAS  Google Scholar 

  32. Darensbourg DJ, Yarbrough JC (2002) J Am Chem Soc 124:6335

    Article  CAS  Google Scholar 

  33. Allen SD, Moore DR, Lobkovsky EB, Coates GW (2002) J Am Chem Soc 124:14284

    Article  CAS  Google Scholar 

  34. Mo WL, Xiong H, Li T, Guo XC, Li GX (2006) J Mol Catal A Chem 247:227

    Article  CAS  Google Scholar 

  35. Kim HS, Bae JY, Lee JS, Kwon OS, Jelliarko P, Lee SD, Lee SH (2005) J Catal 232:80

    Article  CAS  Google Scholar 

  36. Sun J, Wang L, Zhang S, Li Z, Zhang X, Dai W, Mori R (2006) J Mol Catal A Chem 256:295

    Article  CAS  Google Scholar 

  37. Katritzky AR (1963) Physical methods in heterocyclic chemistry. Academic Press, NY

    Google Scholar 

  38. Linstrom PJ, Mallard WG (2001) J Chem Eng Data 46:1059

    Article  CAS  Google Scholar 

  39. Wang RM, Li SB, Wang YP, Chang Y, He YF, Lei ZQ, Feng HX (1999) React Funct Polym 42:87

    Article  CAS  Google Scholar 

  40. Mostafa MF, Youssef AA, El-Dean TS, Mostafa AM, Farag IS (2007) Z Naturfors Sect A J Phys Sci 62:549

    CAS  Google Scholar 

  41. Sun J, Han L, Cheng W, Wang J, Zhang X, Zhang S (2011) ChemSusChem 4:502

    Article  CAS  Google Scholar 

  42. Tsang CW, Baharloo B, Riendl D, Yam M, Gates DP (2004) Angew Chem Int Ed 43:5682

    Article  CAS  Google Scholar 

  43. Kim HS, Kim JJ, Kwon HN, Chung MJ, Lee BG, Jang HG (2002) J Catal 205:226

    Article  CAS  Google Scholar 

  44. Kim HS, Kim JJ, Lee SD, Lah MS, Moon D, Jang HG (2003) Chem A Eur J 9:678

    Article  CAS  Google Scholar 

  45. Hansen KB, Leighton JL, Jacobsen EN (1996) J Am Chem Soc 118:10924

    Article  CAS  Google Scholar 

  46. Jacobsen EN (2000) Acc Chem Res 33:421

    Article  CAS  Google Scholar 

  47. Martinez LE, Leighton JL, Carsten DH, Jacobsen EN (1995) J Am Chem Soc 117:5897

    Article  CAS  Google Scholar 

  48. Schmid GM, Huang HJ (1980) Corros Sci 20:1041

    Article  CAS  Google Scholar 

  49. Wei ZQ, Duby P, Somasundaran P (2003) J Colloid Interf Sci 259:97

    Article  CAS  Google Scholar 

  50. Zhu H, Chen LB, Jiang YY (1996) Polym Adv Technol 7:701

    Article  CAS  Google Scholar 

  51. Shi J, Song J, Ma J, Zhang Z, Fan H, Han B (2013) Pure Appl Chem 85:1633

    Article  CAS  Google Scholar 

  52. Rokicki G, Kuran W, Pogorzelska-Marciniak B (1984) Monatsh Chem 115:205

    Article  CAS  Google Scholar 

  53. Ma J, Song JL, Liu HZ, Liu JL, Zhang ZF, Jiang T, Fan HL, Han BX (2012) Green Chem 14:1743

    Article  CAS  Google Scholar 

Download references

Acknowledgments

We acknowledge financial support of this work by the Distinguished Youth Foundation of Jiangsu Province (BK20130045), the Fok Ying-Tong Education Foundation (141069), the National High Technology Research and Development Program of China (863 Program, 2013AA032003), the National Basic Research Program of China (973 Program, 2013CB733504), the Project of Priority Academic Program Development of Jiangsu Higher Education Institutions(PAPD) and Six talent peaks project in Jiangsu Province (No. 2014-XCL-016).

Author information

Authors and Affiliations

Authors

Corresponding authors

Correspondence to Ding-Hua Liu or Lin-Bing Sun.

Electronic Supplementary Material

Below is the link to the electronic supplementary material.

Supplementary material 1 (DOCX 146 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Shi, YL., Zhang, P., Liu, DH. et al. Homogenous Dual-Ligand Zinc Complex Catalysts for Chemical Fixation of CO2 to Propylene Carbonate. Catal Lett 145, 1673–1682 (2015). https://doi.org/10.1007/s10562-015-1565-9

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10562-015-1565-9

Keywords

Navigation