Abstract
Hydrogenation of biomass-derived furfuryl alcohol to widely used tetrahydrofurfuryl alcohol is an important industrial route, which however calls for a more efficient catalyst. In this work, a highly selective and stable Ni-C-Al2O3 catalyst for furfuryl alcohol hydrogenation to tetrahydrofurfuryl alcohol is reported. The catalyst precursor is prepared by in-situ growth of Ni-based metal organic frameworks (Ni-BTC) on Al2O3 and then the precursor undergoes thermal decomposition to obtain the catalyst directly. For comparison, Ni-C/Al2O3 acquired from pyrolysis of physically mixed Ni-MOFs with Al2O3 and Ni/Al2O3 prepared by impregnation method are also tested as the hydrogenation catalysts. The prepared catalysts are characterized by a series of techniques, including XRD, FT-IR, TG, TEM, SEM, XPS and BET to reveal the relationship between the catalysts structure and their performance. The results show that small metal Ni particle size and appropriate interaction between Ni and the support, which benefit from the in-situ preparation method are key factors that ensure the high furfuryl alcohol conversion (99.8%) and high selectivity to tetrahydrofurfuryl alcohol (98.2%) at moderate reaction conditions (120 °C, 30 min, 4 MPa H2).
Graphical Abstract
Similar content being viewed by others
Change history
09 December 2022
A Correction to this paper has been published: https://doi.org/10.1007/s10562-022-04230-w
References
Rosales-Calderon O, Arantes V (2019) A review on commercial-scale high-value products that can be produced alongside cellulosic ethanol. Biotechnol Biofuels 12:240–298
Xu C, Paone E, Rodríguez-Padrón D, Luque R, Mauriello F (2020) Recent catalytic routes for the preparation and the upgrading of biomass derived furfural and 5-hydroxymethylfurfural. Chem Soc Rev 49:4273–4306
Chen X, Sun W, Xiao N, Yan Y, Liu S (2007) Experimental study for liquid phase selective hydrogenation of furfuryl alcohol to tetrahydrofurfuryl alcohol on supported Ni catalysts. Chem Eng J 126:5–11
Zhu Y, Zhao W, Zhang J, An Z, Ma X, Zhang Z, Jiang Y, Zheng L, Shu X, Song H, Xiang X, He J (2020) Selective activation of C-OH, C-O-C, or C═C in furfuryl alcohol by engineered Pt sites supported on layered double oxides. ACS Catal 10:8032–8041
Mizugaki T, Kaneda K (2019) Development of high performance heterogeneous catalysts for selective cleavage of C-O and C-C bonds of biomass-derived oxygenates. Chem Rec 19:1179–1198
Lan J, Liu P, Fu P, Liu X, Xie M, Jiang S, Wen H, Zhou Y, Wang J (2021) Palladium confined in pure-silica TON zeolite for furfuryl alcohol hydrogenation into tetrahydrofurfuryl alcohol. Microporous Mesoporous Mater 322:111161
Yuan Q, Ye F, Xue T, Guan Y (2015) Room temperature hydrogenation of furfuryl alcohol by Pd/titanate nanotube. Appl Catal A 507:26–33
Sang S, Wang Y, Zhu W, Xiao G (2017) Selective hydrogenation of furfuryl alcohol to tetrahydrofurfuryl alcohol over Ni/γ-Al2O3 catalysts. Res Chem Intermed 43:1179–1195
Wang H, Li X, Lan X, Wang T (2018) Supported ultrafine NiCo bimetallic alloy nanoparticles derived from bimetal-organic frameworks: a highly active catalyst for furfuryl alcohol hydrogenation. ACS Catal 8:2121–2128
Liu X, Zhang L, Wang J (2021) Design strategies for MOF-derived porous functional materials: preserving surfaces and nurturing pores. J Materiomics 7:440–459
Mai HD, Rafiq K, Yoo H (2017) Nano metal-organic framework-derived inorganic hybrid nanomaterials: synthetic strategies and applications. Chem-Eur J 23:5631–5651
Zhou Q, Zhao Q, Xiong W, Li X, Li J, Zeng L (2018) Hollow porous Zinc cobaltate nanocubes photocatalyst derived from bimetallic zeolitic imidazolate frameworks towards enhanced gaseous toluene degradation. J Colloid Interface Sci 516:76–85
Jiang X, Li H, Li S, Huang S, Zhu C, Hou L (2018) Metal-organic framework-derived Ni-Co Alloy@Carbon microspheres as high-performance counter electrode catalysts for dye-sensitized solar cells. Chem Eng J 334:419–431
Zhang X, Chen A, Zhong M, Zhang Z, Zhang X, Zhou Z, Bu XH (2019) Metal-organic frameworks (MOFs) and MOF-derived materials for energy storage and conversion. Electrochem Energy Rev 2:29–104
Hoffer BW, Dick van Langeveld A, Janssens JP, Bonné RLC, Lok CM, Moulijn JA (2000) Stability of highly dispersed Ni/Al2O3 catalysts: effects of pretreatment. J Catal 192:432–440
Maniam P, Stock N (2011) Investigation of porous Ni-based metal-organic frameworks containing paddle-wheel type inorganic building units via high-throughput methods. Inorg Chem 50:5085–5097
Xu Z, Wang N, Chu W, Deng J, Luo S (2015) In situ controllable assembly of layered-double-hydroxide-based nickel nanocatalysts for carbon dioxide reforming of methane. Catal Sci Technol 5:1588–1597
Gedrich K, Senkovska I, Klein N, Stoeck U, Henschel A, Lohe MR, Baburin IA, Mueller U, Kaskel S (2010) A highly porous metal-organic framework with open nickel sites. Angew Chem Int Ed 49:8489–8492
Yang SJ, Nam S, Kim T, Im JH, Jung H, Kang JH, Wi S, Park B, Park CR (2013) Preparation and exceptional lithium anodic performance of porous carbon-coated ZnO quantum dots derived from a metal-organic framework. J Am Chem Soc 135:7394–7397
Wei J, Feng Y, Liu Y, Ding Y (2015) MxCo3-xO4 (M = Co, Mn, Fe) porous nanocages derived from metal-organic frameworks as efficient water oxidation catalysts. J Mater Chem A 3:22300–22310
Das R, Pachfule P, Banerjee R, Poddar P (2012) Metal and metal oxide nanoparticle synthesis from metal organic frameworks (MOFs): finding the border of metal and metal oxides. Nanoscale 4:591–599
Zhou M, Ye J, Liu P, Xu J, Jiang J (2017) Water-assisted selective hydrodeoxygenation of guaiacol to cyclohexanol over supported Ni and Co bimetallic catalysts. ACS Sustain Chem Eng 5:8824–8835
Liu L, Lou H, Chen M (2016) Selective hydrogenation of furfural to tetrahydrofurfuryl alcohol over Ni/CNTs and Bimetallic CuNi/CNTs Catalysts. Int J Hydrog Energy 41:14721–14731
Alberton AL, Souza MMVM, Schmal M (2007) Carbon formation and its influence on ethanol steam reforming over Ni/Al2O3 catalysts. Catal Today 123:257–264
Chen L, Ye J, Yang Y, Yin P, Feng H, Chen C, Zhang X, Wei M, Truhlar DG (2020) Catalytic conversion furfuryl alcohol to tetrahydrofurfuryl alcohol and 2-methylfuran at terrace, step, and corner sites on Ni. ACS Catal 10:7240–7249
Yu W, Xiong K, Ji N, Porosoff MD, Chen JG (2014) Theoretical and experimental studies of the adsorption geometry and reaction pathways of furfural over FeNi bimetallic model surfaces and supported catalysts. J Catal 317:253–262
Guerrero-Torres A, Jiménez-Gómez CP, Cecilia JA, García-Sancho C, Franco F, Quirante-Sánchez JJ, Maireles-Torres P (2019) Ni supported on sepiolite catalysts for the hydrogenation of furfural to value-added chemicals: influence of the synthesis method on the catalytic performance. Top Catal 62:535–550
Bell AT (2003) The impact of nanoscience on heterogeneous catalysis. Science 299:1688–1691
Zhang H, Liu G, Shi L, Ye J (2018) Single-atom catalysts: emerging multifunctional materials in heterogeneous catalysis. Adv Energy Mater 8:1701343
Nakagawa Y, Nakazawa H, Watanabe H, Tomishige K (2012) Total hydrogenation of furfural over a silica-supported nickel catalyst prepared by the reduction of a nickel nitrate precursor. ChemCatChem 4:1791–1797
Qiao C, Jia W, Zhong Q, Liu B, Zhang Y, Meng C, Tian F (2020) MOF-derived Cu-nanoparticle embedded in porous carbon for the efficient hydrogenation of nitroaromatic compounds. Catal Lett 150:3394–3401
Christensen DB, Mortensen RL, Kramer S, Kegnæs S (2020) Study of CoCu alloy nanoparticles supported on MOF-derived carbon for hydrosilylation of ketones. Catal Lett 150:1537–1545
Acknowledgements
This work was financially supported by the Natural Science Research of Jiangsu Higher Education Institutions of China (No. 20KJB530007 and No. 20KJB530012), and the start-up grant from Yancheng Teachers University (72062066001C).
Author information
Authors and Affiliations
Corresponding author
Ethics declarations
Conflict of interests
The authors declare that they have no conflict of interests.
Additional information
Publisher's Note
Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
Supplementary Information
Below is the link to the electronic supplementary material.
Rights and permissions
Springer Nature or its licensor (e.g. a society or other partner) holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law.
About this article
Cite this article
Wang, Y., Liu, S., Zhang, Y. et al. In-Situ Formation of Ni-C-Al2O3 Catalyst from MOFs@Al2O3 Composite for Furfuryl Alcohol Hydrogenation to Tetrahydrofurfuryl Alcohol. Catal Lett 153, 1666–1675 (2023). https://doi.org/10.1007/s10562-021-03851-x
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10562-021-03851-x