A Low-Cost and Easily Prepared Manganese Carbonate as an Efficient Catalyst for Aerobic Oxidation of 5-Hydroxymethylfurfural to 2,5-Diformylfuran

Abstract

A low-cost and easily prepared manganese carbonate (MnCO₃) has been synthesized for catalytic conversion of 5-hydroxymethylfurfural (5-HMF) to 2,5-diformylfuran (DFF). The properties and morphology of the manganese carbonate were measured by SEM, XRD, TGA, BET and XPS. In this method, no harsh reaction conditions were required, and it was a simple and green process for the oxidation of 5-HMF into DFF. To achieve an optimum DFF yield, different reaction conditions, including reaction temperature, reaction time, catalyst amount, and solvents were investigated. Results from the experiments indicated that the highest DFF yield of 86.9% was obtained at 120 °C under atmospheric oxygen pressure after 6 h. Finally, MnCO₃ could be used at least five times with considerable stability.

Keywords

5-Hydroxymethylfurfural / 2,5-Diformylfuran / Manganese carbonate / Non-noble metal catalyst

References

[1] Gallezot P. Conversion of biomass to selected chemical products. Chem Soc Rev, 2012, 41(4): 1538-1558.

[2] Corma AIS, Velty A. Chemical routes for the transformation of biomass into chemicals. Chem Rev, 2007, 107(6): 2411-2502.

[3] Binder JB, Raines RT. Simple chemical transformation of lignocellulosic biomass into furans for fuels and chemicals. J Am Chem Soc, 2009, 131(5): 1979-1985.

[4] Tong X, Ma Y, Li Y. Biomass into chemicals: conversion of sugars to furan derivatives by catalytic processes. Appl Catal A, 2009, 385(1–2): 1-13.

[5] Besson M, Gallezot P, Pinel C. Conversion of biomass into chemicals over metal catalysts. Chem Rev, 2009, 114(3): 1827-1870.

[6] Zhang X, Wu D. Ceramic monolith supported Mn–Ce–M ternary mixed-oxide (M = Cu, Ni or Co) catalyst for VOCs catalytic oxidation. Ceram Int, 2016, 42(15): 16563-16570.

[7] Zou S, Wu Y, Mingde Yang, et al. Production and characterization of bio-oil from hydrothermal liquefaction of microalgae Dunaliella tertiolecta cake. Energy, 2010, 35(12): 5406-5411.

[8] Yurdakal S, Tek BS, Alagöz O, et al. Photocatalytic selective oxidation of 5-(hydroxymethyl)-2-furaldehyde to 2,5-furandicarbaldehyde in water by using anatase, rutile, and brookite TiO₂ nanoparticles. ACS Sustain Chem Eng, 2013, 1(5): 456-461.

[9] Yang Z-Z, Deng J, Pan T, et al. A one-pot approach for conversion of fructose to 2,5-diformylfuran by combination of Fe₃O₄-SBA-SO₃H and K-OMS-2. Green Chem, 2012, 14(11): 2986-2989.

[10] Liu X, Xiao J, Ding H, et al. Catalytic aerobic oxidation of 5-hydroxymethylfurfural over VO²⁺ and Cu²⁺ immobilized on amino functionalized SBA-15. Chem Eng, 2016, 283: 1315-1321.

[11] Wang S, Zhang Z, Liu B. Catalytic conversion of fructose and 5-hydroxymethylfurfural into 2,5-furandicarboxylic acid over a recyclable Fe₃O₄-CoO _x magnetite nanocatalyst. ACS Sustain Chem Eng, 2015, 3(3): 406-412.

[12] Wan X, Zhou C, Chen J, et al. Base-free aerobic oxidation of 5-hydroxymethyl-furfural to 2,5-furandicarboxylic acid in water catalyzed by functionalized carbon nanotube-supported Au–Pd alloy nanoparticles. ACS Catal, 2014, 4(7): 2175-2185.

[13] Ma J, Du Z, Xu J, et al. Efficient aerobic oxidation of 5-hydroxymethylfurfural to 2,5-diformylfuran, and synthesis of a fluorescent material. Chemsuschem, 2011, 4(1): 51-54.

[14] Hopkins KT, Wilson WD, Bender BC, et al. Extended aromatic furan amidino derivatives as anti-Pneumocystis carinii agents. J Med Chem, 1998, 41(20): 3872-3878.

[15] Gandini A. The irruption of polymers from renewable resources on the scene of macromolecular science and technology. Green Chem, 2011, 13(5): 1061-1083.

[16] Zhu Y, Shen M, Xia Y, et al. Au/MnO₂ nanostructured catalysts and their catalytic performance for the oxidation of 5-(hydroxymethyl)furfural. Catal Commun, 2015, 64: 37-43.

[17] Nie J, Xie J, Liu H. Efficient aerobic oxidation of 5-hydroxymethylfurfural to 2,5-diformylfuran on supported Ru catalysts. J Catal, 2013, 301: 83-91.

[18] Moreau C, Durand R, Pourcheron C, et al. Selective oxidation of 5-hydroxymethylfurfural to 2,5-furan-dicarboxaldehyde in the presence of titania supported vanadia catalysts. Stud Surf Sci Catal, 1997, 108: 399-406.

[19] Nie J, Liu H. Efficient aerobic oxidation of 5-hydroxymethylfurfural to 2,5-diformylfuran on manganese oxide catalysts. J Catal, 2014, 316: 57-66.

[20] Liu B, Zhang Z, Lv K, et al. Efficient aerobic oxidation of biomass-derived 5-hydroxymethylfurfural to 2,5-diformylfuran catalyzed by magnetic nanoparticle supported manganese oxide. Appl Catal A General, 2014, 472: 64-71.