Abstract
Fructose is not only an important food and beverage ingredient, but also a renewable resource for production of bio-chemicals. In this paper, a series of N doped mesoporous carbon materials (MCNs) were prepared and evaluated as heterogeneous catalysts for catalytic isomerization of glucose to fructose. The MCNs were prepared through carbonization of p-phenylenediamine disulfate and the effects of desulfonation with NaOH and hydrogenation treatments were examined. It is found that the molar ratio of H2SO4/pPDA crucially affects the porous structure and the nitrogen content. Desulfonation with NaOH treatment could largely eliminate the sulfonic groups on the carbon edges and thus enhance the basicity of the MCN materials, whereas hydrogenation reduction could modify the N atom species and reinforce the strength of the basic sites, as a result enhancing the catalytic activities in glucose isomerization to fructose. Among all of the prepared MCN samples, MCN-2-DH showed an excellent activity in aqueous solution, which afforded a fructose yield of 31.6% with 84.6% selectivity.
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Heck V, Gerten D, Lucht W et al (2018) Biomass-based negative emissions difficult to reconcile with planetary boundaries. Nat Clim Chang 8:660–670
Al-Hamamre Z, Saidan M, Hararah M et al (2017) Wastes and biomass materials as sustainable-renewable energy resources for Jordan. Renew Sustain Energy Rev 67:295–314
Mika LT, Csefalvay E, Nemeth A (2017) Catalytic conversion of carbohydrates to initial platform chemicals: chemistry and sustainability. Chem Rev 118(2):505–613
Elliott DC, Hart TR (2017) Catalytic hydroprocessing of chemical models for bio-oil. Energy Fuels 23(2):631–637
Cai H, Li C, Wang A et al (2014) Biomass into chemicals: one-pot production of furan-based diols from carbohydrates via tandem reactions. Catal Today 234(1):59–65
Robert-Jan VP, Waal JC, Van D et al (2013) Hydroxymethylfurfural, a versatile platform chemical made from renewable resources. Chem Rev 113(3):1499–1597
Wang Y, Zhu L, Zhang Y et al (2018) AlNb/SBA-15 catalysts with tunable Lewis and Bronsted acidic sites for glucose conversion to HMF. ChemistrySelect 3(12):3555–3560
Manuel M, Yuriy RL, Davis ME (2010) Tin-containing zeolites are highly active catalysts for the isomerization of glucose in water. Proc Natl Acad Sci USA 107(14):6164–6168
Lei H, Geng Z, Hao W et al (2012) ChemInform abstract: catalytic conversion of biomass-derived carbohydrates into fuels and chemicals via furanic aldehydes. RSC Adv 2(30):11184–11206
Robert DC, Joseph MA, Poulose AJ et al (2013) Industrial use of immobilized enzymes. Chem Soc Rev 42(15):6437–6474
Vinit C, Mushrif SH, Christopher H et al (2013) Insights into the interplay of Lewis and Bronsted acid catalysts in glucose and fructose conversion to 5-(hydroxymethyl)furfural and levulinic acid in aqueous media. J Am Chem Soc 135(10):3997–4006
Tang J, Guo X, Zhu L et al (2015) A mechanistic study of glucose-to-fructose isomerization in water catalyzed by [Al(OH)2(aq)]+. ACS Catal 5(9):5097–5103
Choudhary V, Pinar AB, Lobo RF et al (2013) Comparison of homogeneous and heterogeneous catalysts for glucose-to-fructose isomerization in aqueous media. ChemSusChem 6(12):2369–2376
Yang Q, Runge T (2016) Polyethylenimines as homogeneous and heterogeneous catalysts for glucose isomerization. ACS Sustain Chem Eng 4(12):6951–6961
Liu C, Carraher JM, Swedberg JL et al (2014) Selective base-catalyzed isomerization of glucose to fructose. ACS Catal 4(12):4295–4298
Bermejo DR, Assary RS, Nikolla E et al (2012) Metalloenzyme-like catalyzed isomerizations of sugars by Lewis acid zeolites. Proc Natl Acad Sci USA 109(25):9727–9732
Qiang Y, Zhou S, Runge T (2015) Magnetically separable base catalysts for isomerization of glucose to fructose. J Catal 330:474–484
Akiyama G, Matsuda R, Sato H et al (2015) Catalytic glucose isomerization by porous coordination polymers with open metal sites. Chem Asian J 9(10):2772–2777
Guo Q, Ren L, Kumar P et al (2018) A chromium hydroxide/MIL-101(Cr) MOF composite catalyst and its use for the selective isomerization of glucose to fructose. Angew Chem 57(18):4926–4930
Cristina M, Tomislav FI (2014) Carbon dioxide sensitivity of zeolitic imidazolate frameworks. Angew Chem 126(29):7601–7604
Shen W, Fan W (2012) Nitrogen-containing porous carbons: synthesis and application. J Mater Chem A 1(4):999–1013
Su Y, Jiang H, Zhu Y et al (2014) Enriched graphitic N-doped carbon-supported Fe3O4 nanoparticles as efficient electrocatalysts for oxygen reduction reaction. J Mater Chem A 2(20):7281–7287
Chandra V, Yu SU, Kim SH et al (2012) Highly selective CO2 capture on N-doped carbon produced by chemical activation of polypyrrole functionalized graphene sheets. Chem Commun 48(5):735–747
Chen SS, Yu IKM, Cho DW et al (2018) Selective glucose isomerization to fructose via a nitrogen-doped solid base catalyst derived from spent coffee grounds. ACS Sustain Chem Eng 6(12):16113–16120
Zhang S, Mandai T, Ueno K et al (2015) Hydrogen-bonding supramolecular protic salt as an “all-in-one” precursor for nitrogen-doped mesoporous carbons for CO2 adsorption. Nano Energy 13:376–386
Han S, Hou W, Xu J et al (2004) Synthesis of hollow spherical silica with MCM-41 mesoporous structure. Colloid Polym Sci 282(11):1286–1291
Shiguo Z, Muhammed SM, Ai I et al (2014) Protic ionic liquids and salts as versatile carbon precursors. J Am Chem Soc 136(5):1690–1703
Hai LJ, Bo L, Ya QL, Kentaro K et al (2011) From metal-organic framework to nanoporous carbon: toward a very high surface area and hydrogen uptake. J Am Chem Soc 133(31):11854–11857
Tao J, Huo P, Fu Z et al (2017) Characterization and phenol adsorption performance of activated carbon prepared from tea residue by NaOH activation. Environ Technol 1:1–41
Wu MB, Li RC, He XJ et al (2015) Microwave-assisted preparation of peanut shell-based activated carbons and their use in electrochemical capacitors. New Carbon Mater 30(1):86–91
Su Y, Jiang H, Zhu Y et al (2014) Enriched graphitic N-doped carbon-supported Fe3O4 nanoparticles as efficient electrocatalysts for oxygen reduction reaction. J Chem A 2(20):7281–7287
Zhang X, Yan F, Zhang S et al (2018) Hollow N-doped carbon polyhedron containing CoNi alloy nanoparticles embedded within few-layer N-doped graphene as high-performance electromagnetic wave absorbing material. ACS Appl Mater Interfaces 10(29):24920–24929
Igalavithana AD, Mandal S, Tsang DCW et al (2017) Advances and future directions of biochar characterization methods and applications. Crit Rev Environ Sci Technol 47(23):2273–2330
Souzanchi S, Nazari L, Yuan Z et al (2018) Catalytic isomerization of glucose to fructose using heterogeneous solid base catalysts in a continuous-flow tubular reactor: catalyst screening study. Catal Today 319(1):76–83
Kicinski W, Szala M, Bystrzejewski M (2014) Sulfur-doped porous carbons: synthesis and applications. Carbon 68(68):1–32
Yuezeng SU, Zhang YI, Zhuang X et al (2013) Low-temperature synthesis of nitrogen/sulfur co-doped three-dimensional graphene frameworks as efficient metal-free electrocatalyst for oxygen reduction reaction. Carbon 62(5):296–301
Yu XR, Liu F, Wang ZY et al (1990) Auger parameters for sulfur-containing compounds using a mixed aluminum-silver excitation source. J Electron Spectrosc Relat Phenom 50(2):159–166
Panchakarla LS, Govindaraj A, Rao CNR (2007) Nitrogen-and boron-doped double-walled carbon nanotubes. ACS Nano 1(5):494–500
Kudin KN, Ozbas B, Schniepp HC et al (2008) Raman spectra of graphite oxide and functionalized graphene sheets. Nano Lett 8(1):36–41
Yu L, Gao B, Chen Z et al (2005) In situ FTIR investigation on phase transformations in BN nanoparticles. Chin Sci Bull 50(24):2827–2831
Lui CH, Liu L, Mak KF et al (2009) Ultraflat graphene. Nature 462(7271):339–341
Graça I, Bacariza MC, Fernandes A et al (2018) Desilicated NaY zeolites impregnated with magnesium as catalysts for glucose isomerisation into fructose. Appl Catal B 224:660–670
Mello MD, Tsapatsis M (2018) Selective glucose-to-fructose isomerization over modified zirconium UiO-66 in alcohol media. ChemCatChem 10(11):2417–2423
Shen F, Fu J, Zhang X et al (2019) Crab shell-derived lotus rootlike porous carbon for high efficiency isomerization of glucose to fructose under mild conditions. ACS Sustain Chem Eng 7(4):4466–4472
Bermejo DR, Orazov M, Gounder R et al (2014) Active sites in Sn-beta for glucose isomerization to fructose and epimerization to mannose. ACS Catal 4(7):2288–2297
Yu IKM, Xiong X, Tsang DCW et al (2019) Aluminium-biochar composites as sustainable heterogeneous catalysts for glucose isomerisation in a biorefinery. Green Chem 21(6):1267–1281
Qiang Y, Wu L, Runge T (2016) Salt-promoted glucose aqueous isomerization catalyzed by heterogeneous organic base. ACS Sustain Chem Eng 4(9):4850–4858
Acknowledgements
The project was supported by the National Natural Science Foundations of China (21978158 and 51536009), the Public Welfare Category of Key R&D Programs in Shandong Province (2018GGX107003) and the Natural Science Foundation of Shandong Province (ZR2018BB062).
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Wang, Y., Wang, J., Zhang, Y. et al. N-Doped Carbon Materials as Heterogeneous Catalysts for High Efficiency Isomerization Glucose to Fructose in Aqueous Media. Catal Lett 150, 493–504 (2020). https://doi.org/10.1007/s10562-019-03020-1
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DOI: https://doi.org/10.1007/s10562-019-03020-1