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Modification of porous lignin with metalloporphyrin as an efficient catalyst for the synthesis of cyclic carbonates

  • Kunpeng SongEmail author
  • Cheng Tang
  • Zhijuan Zou
  • Yundang WuEmail author
Article
  • 39 Downloads

Abstract

The conversion of carbon dioxide into useful chemical raw materials is a necessary development for advancing carbon dioxide capture and storage technology. In this work, a Friedel–Crafts reaction of lignin and metalloporphyrin was used to produce a lignin-based porous organic polymer (P-(L-FeTPP)) with a surface area of up to 1153 m2 g−1. P-(L-FeTPP)) efficiently catalyzed the cycloaddition reactions of epoxides and CO2 under solvent-free conditions, with porphyrin iron acting as an active center. The product yield reached up to 99.6% after 12 h under 1 MPa CO2 and 70 °C. A turnover number of 1481 was achieved, indicating that this catalyst is much more active than its homogeneous counterpart and is one of the most efficient lignin-supported heterogeneous catalysts ever reported. This method for the in situ incorporation of a metalloporphyrin into a lignin skeleton greatly improved the stability of the metal catalyst, and P-(L-FeTPP) was readily recycled and reused more than six times without any significant loss of catalytic activity. Thus, this catalyst design is promising for practical applications, including the industrial production of cyclic carbonates.

Notes

Acknowledgements

This work was financially supported by the National Natural Science Foundations of China (41701305), the Science and Technology Planning Project of Guangdong Province (2017B030314092), Science and Technology Foundation of Sichuan Province (2017JY0015), the Fundamental Research Funds of CWNU (17C038) and the Meritocracy Research Funds of CWNU (17Y031).

Supplementary material

11243_2019_363_MOESM1_ESM.docx (567 kb)
Supplementary material 1 (DOCX 567 kb)

References

  1. 1.
    Supanchaiyamat N, Jetsrisuparb K, Knijnenburg JTN, Tsang DCW, Hunt AJ (2019) Lignin materials for adsorption: current trend, perspectives and opportunities. Bioresour Technol 272:570CrossRefGoogle Scholar
  2. 2.
    Sun Z, Fridrich B, De Santi A, Elangovan S, Barta K (2018) Bright side of lignin depolymerization: toward new platform chemicals. Chem Rev 118:614CrossRefGoogle Scholar
  3. 3.
    Riaz A, Verma D, Zeb H, Lee JH, Kim JC, Kwak SK, Kim J (2018) Solvothermal liquefaction of alkali lignin to obtain a high yield of aromatic monomers while suppressing solvent consumption. Green Chem 20:4957CrossRefGoogle Scholar
  4. 4.
    Ojha DK, Viju D, Vinu R (2017) Fast pyrolysis kinetics of alkali lignin: evaluation of apparent rate parameters and product time evolution. Bioresour Technol 241:142CrossRefGoogle Scholar
  5. 5.
    Mohanty Amar K, Vivekanandhan Singaravelu, Pin Jean-Mathieu, Misra M (2018) Composites from renewable and sustainable resources: challenges and innovations. Science 362:536CrossRefGoogle Scholar
  6. 6.
    Ma Y, Dai J, Wu L, Fang G, Guo Z (2017) Enhanced anti-ultraviolet, anti-fouling and anti-bacterial polyelectrolyte membrane of polystyrene grafted with trimethyl quaternary ammonium salt modified lignin. Polymer 114:113CrossRefGoogle Scholar
  7. 7.
    Ji T, Chen L, Schmitz M, Bao FS, Zhu J (2015) Hierarchical macrotube/mesopore carbon decorated with mono-dispersed Ag nanoparticles as a highly active catalyst. Green Chem 17:2515CrossRefGoogle Scholar
  8. 8.
    Li Z, Chen J, Ge Y (2017) Removal of lead ion and oil droplet from aqueous solution by lignin-grafted carbon nanotubes. Chem Eng J 308:809CrossRefGoogle Scholar
  9. 9.
    Yang D, Huang W, Qiu X, Lou H, Qian Y (2017) Modifying sulfomethylated alkali lignin by horseradish peroxidase to improve the dispersibility and conductivity of polyaniline. Appl Surf Sci 426:287CrossRefGoogle Scholar
  10. 10.
    Wang H, Qiu X, Liu W, Yang D (2017) Facile preparation of well-combined lignin-based carbon/ZnO hybrid composite with excellent photocatalytic activity. Appl Surf Sci 426:206CrossRefGoogle Scholar
  11. 11.
    Meng QB, Weber J (2014) Lignin-based microporous materials as selective adsorbents for carbon dioxide separation. Chemsuschem 7:3312CrossRefGoogle Scholar
  12. 12.
    Xu S, He J, Jin S, Tan B (2018) Heteroatom-rich porous organic polymers constructed by benzoxazine linkage with high carbon dioxide adsorption affinity. J Colloid Interface Sci 509:457CrossRefGoogle Scholar
  13. 13.
    Martín C, Fiorani G, Kleij AW (2015) Recent advances in the catalytic preparation of cyclic organic carbonates. ACS Catal 5:1353CrossRefGoogle Scholar
  14. 14.
    Saptal Vitthal, Shinde Digambar Balaji, Banerjee R, Bhanage BM (2016) State-of-the-Art catechol porphyrin COF catalyst for chemical fixation of carbon dioxide via cyclic carbonates and oxazolidinones. Catal Sci Technol 6:6152CrossRefGoogle Scholar
  15. 15.
    Romelt C, Song J, Tarrago M, Rees JA, Van Gastel M, Weyhermuller T, Debeer S, Bill E, Neese F, Ye S (2017) Electronic structure of a formal iron(0) porphyrin complex relevant to CO2 reduction. Inorg Chem 56:4746CrossRefGoogle Scholar
  16. 16.
    Wang S, Song K, Zhang C, Shu Y, Li T, Tan B (2017) A novel metalporphyrin-based microporous organic polymer with high CO2 uptake and efficient chemical conversion of CO2 under ambient conditions. J Mater Chem A 5:1509CrossRefGoogle Scholar
  17. 17.
    Bai D, Duan S, Hai L, Jing H (2012) Carbon dioxide fixation by cycloaddition with epoxides, catalyzed by biomimetic metalloporphyrins. ChemCatChem 4:1752CrossRefGoogle Scholar
  18. 18.
    Kim MH, Song T, Seo UR, Park JE, Cho K, Lee SM, Kim HJ, Ko Y-J, Chung YK, Son SU (2017) Hollow and microporous catalysts bearing Cr(iii)–F porphyrins for room temperature CO2 fixation to cyclic carbonates. J Mater Chem A 5:23612CrossRefGoogle Scholar
  19. 19.
    Sigen A, Zhang Y, Li Z, Xia H, Xue M, Liu X, Mu Y (2014) Highly efficient and reversible iodine capture using a metalloporphyrin-based conjugated microporous polymer. Chem Commun 50:8495CrossRefGoogle Scholar
  20. 20.
    Dai Z, Sun Q, Liu X, Bian C, Wu Q, Pan S, Wang L, Meng X, Deng F, Xiao F-S (2016) Metalated porous porphyrin polymers as efficient heterogeneous catalysts for cycloaddition of epoxides with CO2 under ambient conditions. J Catal 338:202CrossRefGoogle Scholar
  21. 21.
    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. ChemCatChem 9:767CrossRefGoogle Scholar
  22. 22.
    Yuan K, Song T, Wang D, Zhang X, Gao X, Zou Y, Dong H, Tang Z, Hu W (2018) Effective and selective catalysts for cinnamaldehyde hydrogenation: hydrophobic hybrids of metal-organic frameworks, metal nanoparticles, and micro- and mesoporous polymers. Angew Chem Int Ed 57:5708CrossRefGoogle Scholar
  23. 23.
    Smith PT, Benke BP, Cao Z, Kim Y, Nichols EM, Kim K, Chang CJ (2018) Iron porphyrins embedded into a supramolecular porous organic cage for electrochemical CO2 reduction in water. Angew Chem Int Ed 57:9684CrossRefGoogle Scholar
  24. 24.
    Liu X, Tang B, Long J, Zhang W, Liu X, Mirza Z (2018) The development of MOFs-based nanomaterials in heterogeneous organocatalysis. Sci Bull 63:502CrossRefGoogle Scholar
  25. 25.
    Tang C, Zou Z, Fu Y, Song K (2018) Highly dispersed DPPF locked in knitting hyper-crosslinked polymers as efficient and recyclable catalyst. ChemistrySelect 3:5987CrossRefGoogle Scholar
  26. 26.
    Fu Y-F, Song K-P, Zou Z-J, Li M-Q (2018) External cross-linked sulfonate-functionalized N-heterocyclic carbenes: an efficient and recyclable catalyst for Suzuki–Miyaura reactions in water. Transition Met Chem 43:665CrossRefGoogle Scholar
  27. 27.
    Hou S, Razzaque S, Tan B (2019) Effects of synthesis methodology on microporous organic hyper-cross-linked polymers with respect to structural porosity, gas uptake performance and fluorescence properties. Polym Chem 10:1299CrossRefGoogle Scholar
  28. 28.
    Ema T, Miyazaki Y, Shimonishi J, Maeda C, Hasegawa J-Y (2014) Bifunctional porphyrin catalysts for the synthesis of cyclic carbonates from epoxides and CO2: structural optimization and mechanistic study. J Am Chem Soc 136:15270CrossRefGoogle Scholar
  29. 29.
    Gottfried JM, Flechtner K, Kretschmann A, Lukasczyk T, Steinrück H-P (2006) Direct synthesis of a metalloporphyrin complex on a surface. J Am Chem Soc 128:5644CrossRefGoogle Scholar
  30. 30.
    Song K, Zou Z, Wang D, Tan B, Wang J, Chen J, Li T (2016) Microporous organic polymers derived microporous carbon supported Pd catalysts for oxygen reduction reaction: impact of framework and heteroatom. J Phys Chem C 120:2187CrossRefGoogle Scholar
  31. 31.
    Li S, Wu D, Cheng C, Wang J, Zhang F, Su Y, Feng X (2013) Polyaniline-coupled multifunctional 2D metal oxide/hydroxide graphene nanohybrids. Angew Chem Int Ed 52:12105CrossRefGoogle Scholar
  32. 32.
    Deng F, Garcia-Rodriguez O, Olvera-Vargas H, Qiu S, Lefebvre O, Yang J (2018) Iron-foam as a heterogeneous catalyst in the presence of tripolyphosphate electrolyte for improving electro-Fenton oxidation capability. Electrochim Acta 272:176CrossRefGoogle Scholar
  33. 33.
    Jiménez-Gómez CP, Cecilia JA, García-Sancho C, Moreno-Tost R, Maireles-Torres P (2019) Selective production of furan from gas-phase furfural decarbonylation on Ni-MgO catalysts. ACS Sustain Chem Eng 7:7676CrossRefGoogle Scholar
  34. 34.
    Adler AD, Longo FR, Finarelli JD, Goldmacher J (1967) A simplified synthesis for meso-tetraphenylporphin. J Org Chem 32:476CrossRefGoogle Scholar

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© Springer Nature Switzerland AG 2019

Authors and Affiliations

  1. 1.Chemical Synthesis and Pollution Control Key Laboratory of Sichuan Province, College of Chemistry and Chemical EngineeringChina West Normal UniversityNanchongChina
  2. 2.Guangdong Key Laboratory of Integrated Agro-environmental Pollution Control and ManagementGuangdong Institute of Eco-environmental Science and TechnologyGuangzhouChina
  3. 3.Institute of Synthesis and Application of Functional MaterialsChina West Normal UniversityNanchongChina

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