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Nitrogen-doped reduced graphene oxide-supported Mn3O4: An efficient heterogeneous catalyst for the oxidation of vanillyl alcohol to vanillin

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Abstract

Nitrogen-doped reduced graphene oxide-supported Mn3O4 nanoparticles (N-RGO/Mn3O4) were prepared by solvothermal method and characterized by several physical techniques such as TEM images, XRD, XPS, and N2 adsorption–desorption techniques. The as-made N-RGO/Mn3O4 catalyst was used for the oxidation of vanillyl alcohol to vanillin. Several important reaction parameters were investigated such as reaction solvent, oxygen concentration, reaction temperature, and catalyst loading. N,N-Dimethylformamide was found to be the best solvent, affording both high conversion and vanillin selectivity. 92.5 % conversion of vanillyl alcohol and 91.4 % selectivity of vanillin were achieved after 12 h at 120 °C under oxygen balloon by the use of 40 mg of the N-GO/Mn3O4 catalyst. Kinetic studies revealed that the active energy for the oxidation of vanillyl alcohol to vanillin over N-GO/Mn3O4 catalyst was 39.67 kJ.mol−1. More importantly, the catalyst was stable and could be reused for 6 times without the significant loss of its catalytic activity.

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References

  1. Sun M, Zhang JZ, Putaj P, Caps V, Lefebvre F, Pelletier J, Basset JM (2014) Catalytic oxidation of light alkanes (C1–C4) by heteropoly compounds. Chem Rev 114:981–1019

    Article  Google Scholar 

  2. Kouotou PM, Pan GF, Weng JJ, Fan SB, Tian ZY (2016) Stainless steel grid mesh-supported CVD made Co3O4 thin films for catalytic oxidation of VOCs of olefins type at low temperature. J Ind Eng Chem 35:253–261

    Article  Google Scholar 

  3. Ravat V, Nongwe I, Coville NJ (2016) N-doped ordered mesoporous carbon supported PdCo nanoparticles for the catalytic oxidation of benzyl alcohol. Micropor Mesopor Mat 225:224–231

    Article  Google Scholar 

  4. Karimi B, Rafiee M, Alizadeh S, Vali H (2015) Eco-friendly electrocatalytic oxidation of alcohols on a novel electro generated TEMPO-functionalized MCM-41 modified electrode. Green Chem 17:991–1000

    Article  Google Scholar 

  5. Rao SR, Ravishankar GA (2000) Vanilla flavour: production by conventional and biotechnological routes. J Sci Food Agric 80:289–304

    Article  Google Scholar 

  6. Priefert H, Rabenborst J, Steinb_chel A (2001) Biotechnological production of vanillin. Appl Microbiol Biotechnol 56:296–314

    Article  Google Scholar 

  7. Sheldrak AR (1972) Polar auxin transport in leaves of monocotyledons. Nature 238:352–353

    Article  Google Scholar 

  8. Bulam AD, Nekrasov SV, Passet BV, Foshkin VG (1988) The problem of synthesis of vanillin by the nitrose method. J Appl Chem Ussr 61:859–860

    Google Scholar 

  9. Zhang ZH, Deng KJ (2015) Recent advances in the catalytic synthesis of 2,5-furandicarboxylic acid and its derivatives. ACS Catal 5:6529–6544

    Article  Google Scholar 

  10. Hu J, Hu Y, Mao J, Yao J, Chena Z, Li H (2012) A cobalt schiff base with ionic substituents on the ligand as an efficient catalyst for the oxidation of 4-methyl guaiacol to vanillin. Green Chem 14:2894–2898

    Article  Google Scholar 

  11. Zhang Y, Li X, Cao X, Zhao J (2014) Liquid-phase oxidation of 2-methoxy-p-cresol to vanillin with oxygen catalyzed by a combination of CoCl2 and N-hydroxyphthalimide. Res Chem Intermed 40:1303–1311

    Article  Google Scholar 

  12. Jha A, Rode CV (2013) Highly selective liquid-phase aerobic oxidation of vanillyl alcohol to vanillin on cobalt oxide (Co3O4) nanoparticles. New J Chem 37:2669–2674

    Article  Google Scholar 

  13. Sun KY, Schulz TC, Thompson ST, Lamb HH (2016) Catalytic deoxygenation of octanoic acid over silica- and carbon-supported palladium: support effects and reaction pathways. Catal Today 269:93–102

    Article  Google Scholar 

  14. Perez-Mayoral E, Calvino-Casilda V, Soriano E (2016) Metal-supported carbon-based materials: opportunities and challenges in the synthesis of valuable products. Catal Sci Technol 6:1265–1291

    Article  Google Scholar 

  15. Ren HB, Shi XP, Zhu JY, Zhang Y, Bi YT, Zhang L (2016) Facile synthesis of N-doped graphene aerogel and its application for organic solvent adsorption. J Mater Sci 51:6419–6427. doi:10.1007/s10853-016-9939-y

    Article  Google Scholar 

  16. Zhou M, Wang HL, Guo SJ (2016) Towards high-efficiency nanoelectrocatalysts for oxygen reduction through engineering advanced carbon nanomaterials. Chem Soc Rev 45:1273–1307

    Article  Google Scholar 

  17. Daems N, Sheng X, Vankelecom IFJ, Pescarmona PP (2014) Metal-free doped carbon materials as electrocatalysts for the oxygen reduction reaction. J Mater Chem A 2:4085–4110

    Article  Google Scholar 

  18. Du XQ, Du C, Cai P, Luo W, Cheng GZ (2016) NiPt nanocatalysts supported on boron and nitrogen Co-doped graphene for superior hydrazine dehydrogenation and methanol oxidation. ChemCatChem 8:1410–1416

    Article  Google Scholar 

  19. Lv GQ, Wang HL, Yang YX, Li X, Deng TS, Chen CM, Zhu YL, Hou XL (2016) Aerobic selective oxidation of 5-hydroxymethyl-furfural over nitrogen-doped graphene materials with 2,2,6,6-tetramethylpiperidin-oxyl as co-catalyst. Catal Sci Technol 6:2377–2386

    Article  Google Scholar 

  20. Titova YA, Fedorova V, Rusinov GL, Charushin VN (2015) Metal and silicon oxides as efficient catalysts for the preparative organic chemistry. Russ Chem Rev 84:1294–1315

    Article  Google Scholar 

  21. Mondal J, Borah P, Sreejith S, Nguyen KT, Han XG, Ma X, Zhao YL (2014) Morphology-tuned exceptional catalytic activity of porous-polymer-supported Mn3O4 in aerobic sp3 C–H bond oxidation of aromatic hydrocarbons and alcohols. ChemCatChem 6:3518–3529

    Article  Google Scholar 

  22. Jha A, Chandole T, Pandya R, Roh HS, Rode CV (2014) Solvothermal synthesis of mesoporous manganese oxide with enhanced catalytic activity for veratryl alcohol oxidation. RSC Adv 4:19450–19455

    Article  Google Scholar 

  23. Mei N, Liu B, Zheng JD, Lv KL, Tang DG, Zhang ZH (2015) A novel magnetic palladium catalyst for the mild aerobic oxidation of 5-hydroxymethylfurfural into 2,5-furandicarboxylic acid in water. Catal Sci Technol 5:3194–3202

    Article  Google Scholar 

  24. Li Y, Qu J, Gao F, Lv S, Shi L, He C, Sun J (2015) Appl Catal B 162:268–274

    Article  Google Scholar 

  25. Jasuja K, Berry V (2009) Implantation and growth of dendritic gold nanostructures on graphene derivatives: electrical property tailoring and Raman enhancement. ACS Nano 3:2358–2366

    Article  Google Scholar 

  26. Raj AME, Victoria SG, Jothy VB, Ravidhas C, Wollschlager J, Suendorf M, Neumann M, Jayachandran M, Sanjeeviraja C (2010) XRD and XPS characterization of mixed valence Mn3O4 hausmannite thin films prepared by chemical spray pyrolysis technique. Appl Surf Sci 256:2920–2926

    Article  Google Scholar 

  27. Jeong HK, Lee YP, Lahaye RJ, Park MH, An KH, Kim IJ, Yang CW, Park CY, Ruo RS, Lee YH (2008) Evidence of graphitic AB stacking order of graphite oxides. J Am Chem Soc 130:1362–1366

    Article  Google Scholar 

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Acknowledgement

The project was supported by Special Fund for Basic Scientific Research of Central Colleges, South-Central University for Nationalities (YCZW15100).

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Authors and Affiliations

  1. Key Laboratory of Catalysis and Material Sciences of the State Ethnic Affairs Commission & Ministry of Education, Department of Chemistry, South-Central University for Nationalities, Wuhan, 430074, China

    Ziliang Yuan, Shaohua Chen & Bing Liu

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  1. Ziliang Yuan
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  2. Shaohua Chen
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  3. Bing Liu
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Correspondence to Bing Liu.

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Yuan, Z., Chen, S. & Liu, B. Nitrogen-doped reduced graphene oxide-supported Mn3O4: An efficient heterogeneous catalyst for the oxidation of vanillyl alcohol to vanillin. J Mater Sci 52, 164–172 (2017). https://doi.org/10.1007/s10853-016-0318-5

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