Nano Research

, Volume 9, Issue 10, pp 3129–3140 | Cite as

Nitrogen-doped flower-like porous carbon materials directed by in situ hydrolysed MgO: Promising support for Ru nanoparticles in catalytic hydrogenations

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Abstract

The development of novel, simple, and convenient techniques for the fabrication of porous carbon materials with desirable properties, such as tunable pore structures and the presence of nitrogen functionalities, from renewable and abundant biomasses is required. We herein describe an in situ directing method for the preparation of a nitrogen-doped flower-like porous carbon (NFPC) employing arbitrarily shaped MgO from bio-derived glucosamine chloride (GAH). Experimental evidence demonstrated that the structure directing effect of the Mg(OH)2 nanosheets formed in situ from MgO hydrolysis was key to this process, with the original MgO morphology being irrelevant. Furthermore, this method was applicable for a wide variety of biomass-derived carbon precursors. The resulting NFPC exhibited a high nitrogen content of ≤9 wt.%, and was employed as a support to anchor small Ru nanoparticles (average size = 2.7 nm). The resulting Ru/NFPC was highly active in heterogeneous hydrogenations of toluene and benzoic acid, which demonstrated the advantages of nitrogen doping in terms of boosting catalytic performance.

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Keywords

nitrogen-doped porous carbon MgO in situ hydrolysis ruthenium aromatic hydrogenation 
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Nitrogen-doped flower-like porous carbon materials directed by in situ hydrolysed MgO: Promising support for Ru nanoparticles in catalytic hydrogenations

References

  1. [1]
    Yao, K. X.; Liu, X.; Li, Z.; Li, C. C.; Zeng, H. C.; Han, Y. Preparation of a Ru-nanoparticles/defective-graphene composite as a highly efficient arene-hydrogenation catalyst. ChemCatChem 2012, 4, 1938–1942.CrossRefGoogle Scholar
  2. [2]
    Chuenchom, L.; Kraehnert, R.; Smarsly, B. M. Recent progress in soft-templating of porous carbon materials. Soft Matter. 2012, 8, 10801–10812.CrossRefGoogle Scholar
  3. [3]
    Fang, B. Z.; Kim, J. H.; Kim, M.-S.; Yu, J.-S. Hierarchical nanostructured carbons with meso–macroporosity: Design, characterization, and applications. Acc. Chem. Res. 2013, 46, 1397–1406.CrossRefGoogle Scholar
  4. [4]
    Liang, C. D.; Li, Z. J.; Dai, S. Mesoporous carbon materials: Synthesis and modification. Angew. Chem., Int. Ed. 2008, 47, 3696–3717.CrossRefGoogle Scholar
  5. [5]
    White, R. J.; Budarin, V.; Luque, R.; Clark, J. H.; Macquarrie, D. J. Tuneable porous carbonaceous materials from renewable resources. Chem. Soc. Rev. 2009, 38, 3401–3418.CrossRefGoogle Scholar
  6. [6]
    Sun, Z. Z.; Yan, Z.; Yao, J.; Beitler, E.; Zhu, Y.; Tour, J. M. Growth of graphene from solid carbon sources. Nature 2010, 468, 549–552.CrossRefGoogle Scholar
  7. [7]
    Zhu, Q.-L.; Tsumori, N.; Xu, Q. Immobilizing extremely catalytically active palladium nanoparticles to carbon nanospheres: A weakly-capping growth approach. J. Am. Chem. Soc. 2015, 137, 11743–11748.CrossRefGoogle Scholar
  8. [8]
    Zhang, F. Q.; Meng, Y.; Gu, D.; Yan, Y.; Yu, C. Z.; Tu, B.; Zhao, D. Y. A facile aqueous route to synthesize highly ordered mesoporous polymers and carbon frameworks with Ia3d bicontinuous cubic structure. J. Am. Chem. Soc. 2005, 127, 13508–13509.CrossRefGoogle Scholar
  9. [9]
    Liang, C. D.; Dai, S. Synthesis of mesoporous carbon materials via enhanced hydrogen-bonding interaction. J. Am. Chem. Soc. 2006, 128, 5316–5317.CrossRefGoogle Scholar
  10. [10]
    Xu, X.; Li, Y.; Gong, Y. T.; Zhang, P. F.; Li, H. R.; Wang, Y. Synthesis of palladium nanoparticles supported on mesoporous N-doped carbon and their catalytic ability for biofuel upgrade. J. Am. Chem. Soc. 2012, 134, 16987–16990.CrossRefGoogle Scholar
  11. [11]
    Han, C. L.; Wang, S. P.; Wang, J.; Li, M. M.; Deng, J.; Li, H. R.; Wang, Y. Controlled synthesis of sustainable N-doped hollow core–mesoporous shell carbonaceous nanospheres from biomass. Nano Res. 2014, 7, 1809–1819.CrossRefGoogle Scholar
  12. [12]
    Gong, Y. T.; Zhang, P. F.; Xu, X.; Li, Y.; Li, H. R.; Wang, Y. A novel catalyst Pd@ompg-C3N4 for highly chemoselective hydrogenation of quinoline under mild conditions. J. Catal. 2013, 297, 272–280.CrossRefGoogle Scholar
  13. [13]
    Meng, Y.; Gu, D.; Zhang, F. Q.; Shi, Y. F.; Cheng, L.; Feng, D.; Wu, Z. X.; Chen, Z. X.; Wan, Y.; Stein, A. et al. A family of highly ordered mesoporous polymer resin and carbon structures from organic−organic self-assembly. Chem. Mater. 2006, 18, 4447–4464.CrossRefGoogle Scholar
  14. [14]
    Li, X. H.; Kurasch, S.; Kaiser, U.; Antonietti, M. Synthesis of monolayer-patched graphene from glucose. Angew. Chem., Int. Ed. 2012, 51, 9689–9692.CrossRefGoogle Scholar
  15. [15]
    Wang, S. P.; Han, C. L.; Wang, J.; Deng, J.; Zhu, M. L.; Yao, J.; Li, H. R.; Wang, Y. Controlled synthesis of ordered mesoporous carbohydrate-derived carbons with flower-like structure and N-doping by self-transformation. Chem. Mater. 2014, 26, 6872–6877.CrossRefGoogle Scholar
  16. [16]
    Guo, B. K.; Wang, X. Q.; Fulvio, P. F.; Chi, M. F.; Mahurin, S. M.; Sun, X.-G.; Dai, S. Soft-templated mesoporous carbon-carbon nanotube composites for high performance lithium-ion batteries. Adv. Mater. 2011, 23, 4661–4666.CrossRefGoogle Scholar
  17. [17]
    Han, S. J.; Sohn, K.; Hyeon, T. Fabrication of new nanoporous carbons through silica templates and their application to the adsorption of bulky dyes. Chem. Mater. 2000, 12, 3337–3341.CrossRefGoogle Scholar
  18. [18]
    Wang, Y.; Yao, J.; Li, H. R.; Su, D. S.; Antonietti, M. Highly selective hydrogenation of phenol and derivatives over a Pd@carbon nitride catalyst in aqueous media. J. Am. Chem. Soc. 2011, 133, 2362–2365.CrossRefGoogle Scholar
  19. [19]
    Ryoo, R.; Joo, S. H.; Jun, S. Synthesis of highly ordered carbon molecular sieves via template-mediated structural transformation. J. Phys. Chem. B 1999, 103, 7743–7746.CrossRefGoogle Scholar
  20. [20]
    Li, Z. J.; Dai, S. Surface functionalization and pore size manipulation for carbons of ordered structure. Chem. Mater. 2005, 17, 1717–1721.CrossRefGoogle Scholar
  21. [21]
    Joo, S. H.; Choi, S. J.; Oh, I.; Kwak, J.; Liu, Z.; Terasaki, O.; Ryoo, R. Ordered nanoporous arrays of carbon supporting high dispersions of platinum nanoparticles. Nature 2001, 412, 169–172.CrossRefGoogle Scholar
  22. [22]
    Kim, T.-W.; Kleitz, F.; Paul, B.; Ryoo, R. MCM-48-like large mesoporous silicas with tailored pore structure: Facile synthesis domain in a ternary triblock copolymer−butanol− water system. J. Am. Chem. Soc. 2005, 127, 7601–7610.CrossRefGoogle Scholar
  23. [23]
    Liu, J.; Yang, T. Y.; Wang, D.-W.; Lu, G. Q.; Zhao, D. Y.; Qiao, S. Z. A facile soft-template synthesis of mesoporous polymeric and carbonaceous nanospheres. Nat. Commun. 2013, 4, 2798.Google Scholar
  24. [24]
    Zhao, L.; Fan, L.-Z.; Zhou, M.-Q.; Guan, H.; Qiao, S. Y.; Antonietti, M.; Titirici, M.-M. Nitrogen-containing hydrothermal carbons with superior performance in supercapacitors. Adv. Mater. 2010, 22, 5202–5206.CrossRefGoogle Scholar
  25. [25]
    Tang, M. H.; Mao, S. J.; Li, M. M.; Wei, Z. Z.; Xu, F.; Li, H. R.; Wang, Y. RuPd alloy nanoparticles supported on N-doped carbon as an efficient and stable catalyst for benzoic acid hydrogenation. ACS Catal. 2015, 5, 3100–3107.CrossRefGoogle Scholar
  26. [26]
    Li, M. M.; Xu, F.; Li, H. R.; Wang, Y. Nitrogen-doped porous carbon materials: Promising catalysts or catalyst supports for heterogeneous hydrogenation and oxidation. Catal. Sci. Technol. 2016, 6, 3670–3693.CrossRefGoogle Scholar
  27. [27]
    Barrett, C. J.; Chheda, J. N.; Huber, G. W.; Dumesic, J. A. Single-reactor process for sequential aldol-condensation and hydrogenation of biomass-derived compounds in water. Appl. Catal. B 2006, 66, 111–118.CrossRefGoogle Scholar
  28. [28]
    Corma, A.; Ródenas, T.; Sabater, M. J. A bifunctional Pd/ MgO solid catalyst for the one-pot selective N-monoalkylation of amines with alcohols. Chem.—Eur. J. 2010, 16, 254–260.CrossRefGoogle Scholar
  29. [29]
    Fang, M. F.; Sánchez-Delgado, R. A. Ruthenium nanoparticles supported on magnesium oxide: A versatile and recyclable dual-site catalyst for hydrogenation of mono- and polycyclic arenes, N-heteroaromatics, and S-heteroaromatics. J. Catal. 2014, 311, 357–368.CrossRefGoogle Scholar
  30. [30]
    Xie, K.; Qin, X. T.; Wang, X. Z.; Wang, Y. N.; Tao, H. S.; Wu, Q.; Yang, L. J.; Hu, Z. Carbon nanocages as supercapacitor electrode materials. Adv. Mater. 2012, 24, 347–352.CrossRefGoogle Scholar
  31. [31]
    Cui, C. J.; Qian, W. Z.; Yu, Y. T.; Kong, C. Y.; Yu, B.; Xiang, L.; Wei, F. Highly electroconductive mesoporous graphene nanofibers and their capacitance performance at 4 V. J. Am. Chem. Soc. 2014, 136, 2256–2259.CrossRefGoogle Scholar
  32. [32]
    Ning, G. Q.; Liu, Y.; Wei, F.; Wen, Q.; Luo, G. H. Porous and lamella-like Fe/MgO catalysts prepared under hydrothermal conditions for high-yield synthesis of double-walled carbon nanotubes. J. Phys. Chem. C 2007, 111, 1969–1975.CrossRefGoogle Scholar
  33. [33]
    Fan, Z. J.; Liu, Y.; Yan, J.; Ning, G. Q.; Wang, Q.; Wei, T.; Zhi, L. J.; Wei, F. Template-directed synthesis of pillaredporous carbon nanosheet architectures: High-performance electrode materials for supercapacitors. Adv. Energy Mater. 2012, 2, 419–424.CrossRefGoogle Scholar
  34. [34]
    Ning, G. Q.; Fan, Z. J.; Wang, G.; Gao, J. S.; Qian, W. Z.; Wei, F. Gram-scale synthesis of nanomesh graphene with high surface area and its application in supercapacitor electrodes. Chem. Commun. 2011, 47, 5976–5978.CrossRefGoogle Scholar
  35. [35]
    Ning, G. Q.; Xu, C. G.; Zhu, X.; Zhang, R. F.; Qian, W. Z.; Wei, F.; Fan, Z. J.; Gao, J. S. MgO-catalyzed growth of N-doped wrinkled carbon nanotubes. Carbon 2013, 56, 38–44.CrossRefGoogle Scholar
  36. [36]
    Zhu, X.; Ning, G. Q.; Fan, Z. J.; Gao, J. S.; Xu, C. M.; Qian, W. Z.; Wei, F. One-step synthesis of a graphene-carbon nanotube hybrid decorated by magnetic nanoparticles. Carbon 2012, 50, 2764–2771.CrossRefGoogle Scholar
  37. [37]
    Lepró, X.; Terrés, E.; Vega-Cantú, Y.; Rodríguez-Macías, F. J.; Muramatsu, H.; Kim, Y. A.; Hayahsi, T.; Endo, M.; Torres R, M.; Terrones, M. Efficient anchorage of Pt clusters on N-doped carbon nanotubes and their catalytic activity. Chem. Phys. Lett. 2008, 463, 124–129.CrossRefGoogle Scholar
  38. [38]
    Amadou, J.; Chizari, K.; Houllé, M.; Janowska, I.; Ersen, O.; Bégin, D.; Pham-Huu, C. N-doped carbon nanotubes for liquid-phase C=C bond hydrogenation. Catal. Today 2008, 138, 62–68.CrossRefGoogle Scholar
  39. [39]
    Villa, A.; Wang, D.; Spontoni, P.; Arrigo, R.; Su, D. S.; Prati, L. Nitrogen functionalized carbon nanostructures supported Pd and Au–Pd NPs as catalyst for alcohols oxidation. Catal. Today 2010, 157, 89–93.CrossRefGoogle Scholar
  40. [40]
    Ning, X. M.; Yu, H.; Peng, F.; Wang, H. J. Pt nanoparticles interacting with graphitic nitrogen of N-doped carbon nanotubes: Effect of electronic properties on activity for aerobic oxidation of glycerol and electro-oxidation of CO. J. Catal. 2015, 325, 136–144.CrossRefGoogle Scholar
  41. [41]
    Li, Z. L.; Liu, J. H.; Xia, C. G.; Li, F. W. Nitrogenfunctionalized ordered mesoporous carbons as multifunctional supports of ultrasmall Pd nanoparticles for hydrogenation of phenol. ACS Catal. 2013, 3, 2440–2448.CrossRefGoogle Scholar
  42. [42]
    Zhang, P. F.; Gong, Y. T.; Li, H. R.; Chen, Z. R.; Wang, Y. Solvent-free aerobic oxidation of hydrocarbons and alcohols with Pd@N-doped carbon from glucose. Nat. Commun. 2013, 4, 1593.CrossRefGoogle Scholar
  43. [43]
    Kim, M. G.; Dahmen, U.; Searcy, A. W. Structural transformations in the decomposition of Mg(OH)2 and MgCO3. J. Am. Ceram. Soc. 1987, 70, 146–154.CrossRefGoogle Scholar
  44. [44]
    Chen, X. Y.; He, Y. Y.; Xia, Y. K.; Zhang, Z. J. Nitrogencontaining nanoporous carbons with high pore volumes from 4-(4-nitrophenylazo)resorcinol by a Mg(OH)2-assisted template carbonization method. J. Mater. Chem. A 2014, 2, 17586–17594.CrossRefGoogle Scholar
  45. [45]
    Zhang, W. F.; Huang, Z.-H.; Zhou, C. J.; Cao, G. P.; Kang, F. Y.; Yang, Y. S. Porous carbon for electrochemical capacitors prepared from a resorcinol/formaldehyde-based organic aquagel with nano-sized particles. J. Mater. Chem. 2012, 22, 7158–7163.CrossRefGoogle Scholar
  46. [46]
    Yi, H. T.; Zhu, Y. Q.; Chen, X. Y.; Zhang, Z. J. A simple Mg(OH)2-assisted template carbonization method to N-doped nanoporous carbon material from phenidone and the capacitive improvement with the addition of azobisformamide. Electrochim. Acta 2015, 174, 111–119.CrossRefGoogle Scholar
  47. [47]
    Su, F. B.; Lv, L.; Lee, F. Y.; Liu, T.; Cooper, A. I.; Zhao, X. S. Thermally reduced ruthenium nanoparticles as a highly active heterogeneous catalyst for hydrogenation of monoaromatics. J. Am. Chem. Soc. 2007, 129, 14213–14223.CrossRefGoogle Scholar
  48. [48]
    Zahmakıran, M.; Tonbul, Y.; Özkar, S. Ruthenium(0) nanoclusters stabilized by a nanozeolite framework: Isolable, reusable, and green catalyst for the hydrogenation of neat aromatics under mild conditions with the unprecedented catalytic activity and lifetime. J. Am. Chem. Soc. 2010, 132, 6541–6549.CrossRefGoogle Scholar
  49. [49]
    Roucoux, A.; Schulz, J.; Patin, H. Reduced transition metal colloids: A novel family of reusable catalysts? Chem. Rev. 2002, 102, 3757–3778.CrossRefGoogle Scholar
  50. [50]
    Antonetti, C.; Oubenali, M.; Raspolli Galletti, A. M.; Serp, P.; Vannucci, G. Novel microwave synthesis of ruthenium nanoparticles supported on carbon nanotubes active in the selective hydrogenation of p-chloronitrobenzene to p-chloroaniline. Appl. Catal. A 2012, 421–422, 99–107.CrossRefGoogle Scholar
  51. [51]
    Morgan, D. J. Resolving ruthenium: XPS studies of common ruthenium materials. Surf. Interface Anal. 2015, 47, 1072–1079.CrossRefGoogle Scholar
  52. [52]
    Nie, R. F.; Miao, M.; Du, W. C.; Shi, J. J.; Liu, Y. C.; Hou, Z. Y. Selective hydrogenation of C=C bond over N-doped reduced graphene oxides supported Pd catalyst. Appl. Catal. B 2016, 180, 607–613.CrossRefGoogle Scholar
  53. [53]
    Xu, X.; Li, H. R.; Wang, Y. Selective hydrogenation of phenol to cyclohexanone in water over Pd@N-doped carbon derived from ionic-liquid precursors. ChemCatChem 2014, 6, 3328–3332.CrossRefGoogle Scholar
  54. [54]
    Mondal, J.; Kundu, S. K.; Hung Ng, W. K.; Singuru, R.; Borah, P.; Hirao, H.; Zhao, Y. L.; Bhaumik, A. Fabrication of ruthenium nanoparticles in porous organic polymers: Towards advanced heterogeneous catalytic nanoreactors. Chem.—Eur. J. 2015, 21, 19016–19027.CrossRefGoogle Scholar
  55. [55]
    Xu, X.; Tang, M. H.; Li, M. M.; Li, H. R.; Wang, Y. Hydrogenation of benzoic acid and derivatives over Pd nanoparticles supported on N-doped carbon derived from glucosamine hydrochloride. ACS Catal. 2014, 4, 3132–3135.CrossRefGoogle Scholar

Copyright information

© Tsinghua University Press and Springer-Verlag Berlin Heidelberg 2016

Authors and Affiliations

  • Mingming Li
    • 1
  • Minghui Tang
    • 1
  • Jiang Deng
    • 1
  • Yong Wang
    • 1
  1. 1.Advanced Materials and Catalysis Group, ZJU-NHU United R&D Center, Department of ChemistryZhejiang UniversityHangzhouChina

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