Aerobic oxidation of biomass-derived 5-(hydroxymethyl)furfural into 2,5-diformylfuran catalyzed by the trimetallic mixed oxide (Co-Ce-Ru)

Industrial and Engineering Chemistry Research

Volumn 53, Issue 4, 2014, Pages 1313-1319

  Wang, Yimei ^a   Liu, Bing ^a   Huang, Kecheng ^a   Zhang, Zehui ^a  

^a SOUTH CENTRAL UNIVERSITY FOR NATIONALITIES   (China)

Author keywords

[No Author keywords available]

Indexed keywords

AEROBIC OXIDATIONS; ALKALI HYDROLYSIS; ATMOSPHERIC OXYGEN PRESSURE; MIXED OXIDE; OPTIMAL CONDITIONS; REACTION PARAMETERS; REACTION TEMPERATURE; TRIMETALLIC;

ALDEHYDES; CATALYSIS; CATALYST ACTIVITY; FURFURAL; METHANOL; OXIDANTS; TRANSMISSION ELECTRON MICROSCOPY; X RAY DIFFRACTION;

OXIDATION;

EID: 84893285682     PISSN: 08885885     EISSN: 15205045     Source Type: Journal    
DOI: 10.1021/ie4034363     Document Type: Article

References (41)

1. Ragauskas, A. J.; Williams, C. K.; Davison, B. H.; Britovsek, G.; Cairney, J.; Eckert, C. A.; Frederick, W. J.; Pallett, J. P., Jr.; Leak, D. J.; Liotta, C. L.; Mielenz, J. R.; Murphy, R.; Templer, R.; Tschaplinski, T. The path forward for biofuels and biomaterials Science 2006, 311, 484
2. Modenbach, A. A.; Nokes, S. E. Enzymatic hydrolysis of biomass at high-solids loadings-A review Biomass Bioenergy 2013, 56, 526
3. 3 Fuel 2013, 113, 625
4. Agirrezabal-Telleria, I.; Gandarias, I.; Arias, P. L. Production of furfural from pentosan-rich biomass: Analysis of process parameters during simultaneous furfural stripping Bioresour. Technol. 2013, 143, 258
5. Kantarelis, E.; Yang, W.; Blasiak, W. Production of liquid feedstock from biomass via steam pyrolysis in a fluidized bed reactor Energy Fuels 2013, 8, 4748
6. Dutta, S.; De, S.; Saha, B. A brief summary of the synthesis of polyester building-block chemicals and biofuels from 5-hydroxymethylfurfural ChemPlusChem 2012, 77, 259
7. Zhang, Z. H.; Wang, Q.; Xie, H. B.; Liu, W. J.; Zhao, Z. K. Catalytic conversion of carbohydrates into 5-hydroxymethylfurfural by germanium(IV) chloride in ionic liquids ChemSusChem 2011, 4, 131
8. Binder, J. B.; Raines, R. T. Simple chemical transformation of lignocellulosic biomass into furans for fuels and chemicals J. Am. Chem. Soc. 2009, 131, 1979
9. Qu, Y. S.; Song, Y. L.; Huang, C. P.; Zhang, J.; Chen, B. H. Alkaline ionic liquids as catalysts: A novel and green process for the dehydration of carbohydrates to give 5-hydroxymethylfurfural Ind. Eng. Chem. Res. 2012, 51, 13008
10. Liu, B.; Zhang, Z. H.; Zhao, Z. K. Microwave-assisted catalytic conversion of cellulose into 5-hydroxymethylfurfural in ionic liquids Chem. Eng. J. 2013, 215-216, 517
11. Rosatella, A. A.; Simeonov, S. P.; Frade, R. F. M.; Afonso, C. A. M. 5-Hydroxymethylfurfural (HMF) as a building block platform: biological properties, synthesis and synthetic applications Green Chem. 2011, 13, 754
12. Buntara, T.; Noel, S.; Phua, P. H.; Melian-Cabrera, I.; De Vries, J. G.; Heeres, H. J. Caprolactam from renewable Resources: catalytic conversion of 5-hydroxymethylfurfural into caprolactone Angew. Chem., Int. Ed. 2011, 50, 7083
13. Subbiah, S.; Simeonov, S. P.; Esperanca, J. M. S. S.; Rebelo, L. P. N.; Afonso, C. A. M. Direct transformation of 5-hydroxymethylfurfural to the building blocks 2,5-dihydroxymethylfurfural (DHMF) and 5-hydroxymethyl furanoic acid (HMFA) via Cannizzaro reaction Green Chem. 2013, 15, 2849
14. Moreau, C.; Belgacem, M. N.; Gandini, A. Recent catalytic advances in the chemistry of substituted furans from carbohydrates and in the ensuing polymers Top. Catal. 2004, 27, 11
15. Gandini, A. The irruption of polymers from renewable resources on the scene of macromolecular science and technology Green Chem. 2011, 13, 1061
16. Pasini, T.; Piccinini, M.; Blosi, M.; Bonelli, R.; Albonetti, S.; Dimitratos, N.; Lopez- Sanchez, J. A.; Sankar, M.; He, Q.; Kiely, C. J.; Hutchings, G. J.; Cavani, F. Selective oxidation of 5-hydroxymethyl-2-furfural using supported gold-copper nanoparticles Green Chem. 2011, 13, 2091
17. Davis, S. E.; Houk, L. R.; Tamargo, E. C.; Datye, A. K.; Davis, R. J. Oxidation of 5-hydroxymethylfurfural over supported Pt, Pd and Au catalysts Catal. Today 2011, 160, 55
18. Carlini, C.; Patrono, P.; Galletti, A. M. R.; Sbrana, G.; Zima, V. Selective oxidation of 5-hydroxymethyl-2-furaldehyde to furan-2,5- dicarboxaldehyde by catalytic systems based on vanadyl phosphate Appl. Catal., A 2005, 289, 197
19. Casanova, O.; Iborra, S.; Corma, A. Biomass into chemicals: aerobic oxidation of 5-hydroxymethyl-2-furfural into 2,5-furandicarboxylic acid with gold nanoparticle catalysts ChemSusChem 2009, 2, 1138
20. Saha, B.; Dutta, S.; Abu-Omar, M. M. Aerobic oxidation of 5-hydroxylmethylfurfural with homogeneous and nanoparticulate catalysts Catal. Sci. Technol. 2012, 2, 79
21. Saha, B.; Gupta, D.; Abu-Omar, M. M.; Modak, A.; Bhaumik, A. Porphyrin-based porous organic polymer-supported iron(III) catalyst for efficient aerobic oxidation of 5-hydroxymethylfurfural into 2,5- furandicarboxylic acid J. Catal. 2013, 299, 316
22. Ma, J. P.; Du, Z. T.; Xu, J.; Chu, Q.; Pang, Y. Efficient aerobic oxidation of 5-hydroxymethylfurfural to 2,5-diformylfuran, and synthesis of a fluorescent material ChemSusChem 2011, 4, 51
23. Adams, H.; Bastida, R.; deBlas, A.; Carnota, M.; Fenton, D. E.; Macias, A.; Rodriguez, A.; Rodriguez Blas, T. Complexes of lead(II) and lanthanide(III) ions with a macrocyclic ligand containing a furan head unit. Crystal structure of a methanol inclusion compound of a novel macrocycle Polyhedron 2007, 16, 567
24. Amarasekara, A. S.; Green, D.; Williams, L. D. Renewable resources based polymers: Synthesis and characterization of 2,5-diformylfuran-urea resin Eur. Polym. J. 2009, 45, 595
25. Ma, J. P.; Wang, M.; Du, Z. T.; Chen, C.; Gao, J.; Xu, J. Synthesis and properties of furan-based imine-linked porous organic frameworks Polym. Chem. 2009, 3, 2346
26. Amarasekara, A. S.; Green, D.; McMillan, E. Efficient oxidation of 5-hydroxymethylfurfural to 2,5-diformylfuran using Mn(III)-salen catalysts Catal. Commun. 2008, 9, 286
27. Lichtenthaler, F. W. Unsaturated O- and N-heterocycles from carbohydrate feedstocks Acc. Chem. Res. 2002, 35, 728
28. Cottier, L.; Descotes, G.; Viollet, E.; Lewkowski, J.; Skowroński, R. Oxidation of 5-hydroxymethylfurfural and derivatives to furanaldehydes with 2,2,6,6-tetramethylpiperidine oxide radical-co-oxidant pairs J. Heterocycl. Chem. 1995, 32, 927
29. Krystof, M.; Perez-Sanchez, M.; de Maria, P. D. Lipase-Mediated Selective Oxidation of Furfural and 5-Hydroxymethylfurfural ChemSusChem 2013, 6, 826
30. Nie, J. F.; Xie, J. H.; Liu, H. C. Activated carbon-supported ruthenium as an efficient catalyst for selective aerobic oxidation of 5- hydroxymethylfurfural to 2,5-diformylfuran Chinese J. Catal. 2013, 34, 871
31. Nie, J. F.; Xie, J. H.; Liu, H. C. Efficient aerobic oxidation of 5-hydroxymethylfurfural to 2,5-diformylfuran on supported Ru catalysts J. Catal. 2013, 301, 83
32. Takagaki, A.; Takahashi, M.; Nishimura, S.; Ebitani, K. One-pot synthesis of 2,5-diformylfuran from carbohydrate derivatives by sulfonated resin and hydrotalcite-supported ruthenium catalysts ACS Catal. 2011, 1, 1562
33. Grasset, F. L.; Katryniok, B.; Paul, S.; Nardello-Rataj, V.; Pera-Titus, M.; Clacens, J. M.; De Campo, F.; Dumeignil, F. Selective oxidation of 5-hydroxymethylfurfural to 2,5-diformylfuran over intercalated vanadium phosphate oxides RSC Adv. 2013, 3, 9942
34. Sádaba, I.; Gorbanev, Y. Y.; Kegnæs, S.; Putluru, S. S. R.; Berg, R. W.; Riisager, A. Catalytic performance of zeolite-supported vanadia in the aerobic oxidation of 5-hydroxymethylfurfural to 2,5-diformylfuran ChemCatChem 2013, 5, 284
35. 2/CoO(OH) catalyst for oxidation of alcohols in the presence of molecular oxygen J. Mol. Catal. A: Chem. 2004, 212, 161
36. 3- xAl hydrotalcites Fuel 2012, 96, 257
37. Ghiacia, M.; Aghabararia, B.; do Rego, A. M. B.; Ferraria, A. M.; Habibollahi, S. Efficient allylic oxidation of cyclohexene catalyzed by trimetallic hybrid nano-mixed oxide (Ru/Co/Ce) Appl. Catal., A 2011, 393, 225
38. Stuchinskaya, T. L.; Musawir, M.; Kozhevnikova, E. F.; Kozhevnikov, I. V. Liquid-phase oxidation of alcohols by oxygen and nitrous oxide catalysed by Ru-Co oxide J. Catal. 2005, 231, 41
39. 2 catalyzed by polymer supported transition metal complexes J. Mol. Catal. A: Chem. 1997, 120, 47
40. Namboodiri, V. V.; Polshettiwar, V.; Varma, R. S. Expeditious oxidation of alcohols to carbonyl compounds using iron(III) nitrate Tetrahedron Lett. 2007, 48, 8839
41. Patil, S. K. R.; Lund, C. R. F. Formation and growth of humins via aldol addition and condensation during acid-catalyzed conversion of 5-hydroxymethylfurfural Energy Fuels 2011, 25, 4745