Abstract
Anisole (methoxybenzene) often serves as a potent biomass model compound in hydrodeoxygenation (HDO) reactions with the primary aim to underpin conditions and operations that facilitate conversion of bio-oil into non-oxygenated fuel. However, the majority of studies in literature has focused on its HDO in a solvent environment under excessive conditions of high hydrogen flow rate and elevated pressures. Herein, we investigate HDO of an evaporated stream anisole on a continues flow reactor over four combination of Ni/Co catalysts supported on Zeolite or Al2O3. Catalysts were characterized by various methods which span XRD, SEM-EDS and TPR. The reaction was carried out between 300–600 °C. The highest conversion at 87% was acquired using the Ni–Co/Zeolite catalyst (87%) while producing high yield of phenols and cresols. Synergistic effects brought by the incorporation of Co in the lattice of the catalyst has been discussed. Overall, we obtained a viable HDO path for this biomass model compound using combination of different supported catalysts at moderate operational conditions (relatively intermediate temperatures, ambient pressure, and low H2/Feed ratio).
Graphical Abstract
Similar content being viewed by others
Abbreviations
- HDO:
-
Hydrodeoxygenation
- XRD:
-
X-ray Diffraction
- TPR:
-
Temperature Programmed Reduction
- SEM:
-
Scanning Electron Microscope
- EDS:
-
Energy-Dispersive X-ray Spectroscopy
References
Kumar A, Kumar J, Bhaskar T (2020) High surface area biochar from Sargassum tenerrimum as potential catalyst support for selective phenol hydrogenation. Environ Res 186:0013–9351. https://doi.org/10.1016/j.envres.2020.109533
Gundekari S, Biswas B, Bhaskar T, Srinivasan K (2022) Preparation of cyclohexanol from lignin-based phenolic concoction using controlled hydrogen delivery tool over in-situ Ru catalyst. Biomass Bioenergy 161:0961–9534. https://doi.org/10.1016/j.biombioe.2022.106448
Zeng Y, Wang Z, Lin W, Song W, Christensen J, Jensen A (2016) Hydrodeoxygenation of phenol over Pd catalysts by in-situ generated hydrogen from aqueous reforming of formic acid. Catal Commun 82:1566–7367. https://doi.org/10.1016/j.catcom.2016.04.018
Zaiman Z, Hao L (2022) Water-mediated catalytic hydrodeoxygenation of biomass. Fuel. https://doi.org/10.1016/j.fuel.2021.122242
Liu X, Jia W, Xu G, Zhang Y, Fu Y (2017) Selective hydrodeoxygenation of lignin-derived phenols to cyclohexanols over Co-based catalysts. ACS Sustain Chem Eng 5:10:8594–8601. https://doi.org/10.1021/acssuschemeng.7b01047
Valentini F, Marrocchi A, Vaccaro L (2022) Liquid organic hydrogen carriers (LOHCs) as H-source for bio-derived fuels and additives production. Adv Energy Mater 12:13. https://doi.org/10.1002/aenm.202103362
Mengran L, Jingui Z, Lirong Z, Guoli F, Lan Y, Feng L (2020) Significant promotion of surface oxygen vacancies on bimetallic CoNi nanocatalysts for hydrodeoxygenation of biomass-derived vanillin to produce methylcyclohexanol. ACS Sustain Chem 8:6075–6089. https://doi.org/10.1021/acssuschemeng.0c01015
Mustapha Y, Gary L (2023) Anisole hydrodeoxygenation over nickel-based catalysts: influences of solvent and support properties. Energy Fuels 37:2:1225–1237. https://doi.org/10.1021/acs.energyfuels.2c03734
Wang D, Gu X, Shi H, Chen J (2022) Effect of Zn on performance of Ni/SiO2 for hydrodeoxygenation of anisole. J Fuel Chem Technol 50:1341–1349. https://doi.org/10.1016/S1872-5813(22)60029-X
Kumar A, Jindal M, Rawat S, Sahoo A, Verma R, Changdra D, Kumar S, Thallada B, Yang B (2022) Anisole hydrodeoxygenation over Ni–Co bimetallic catalyst: a combination of experimental, kinetic and DFT study. RSC Adv 12:30236–30247. https://doi.org/10.1039/D2RA05136B
Duong N, Aruho D, Wang B, Resasco D (2019) Hydrodeoxygenation of anisole over different Rh surfaces. Chin J Catal 40:11. https://doi.org/10.1016/S1872-2067(19)63345-0
Yan P, Kennedy E, Stockenhuber M (2021) Natural zeolite supported Ni catalysts for hydrodeoxygenation of anisole. Green Chem 23:4673–4684. https://doi.org/10.1039/D0GC04377J
Zanuttini MS, Lago CD, Gross MS, Peralta MA, Querini CA (2017) Hydrodeoxygenation of anisole with Pt catalysts. Ind Eng Chem Res 56:6419–6431. https://doi.org/10.1021/acs.iecr.7b00521
Taghvaei H, Rahimpour M, Bruggeman P (2017) Catalytic hydrodeoxygenation of anisole over nickel supported on plasma treated alumina–silica mixed oxides. RSC Adv 7:30990–30998. https://doi.org/10.1039/C7RA02594G
Sankaranarayanan T, Berenguer A, Hernandez C, Moreno I, Jana P, Coronado J, Serrano D, Pizarro P (2015) Hydrodeoxygenation of anisole as bio-oil model compound over supported Ni and Co catalysts: effect of metal and support properties. Catal Today 243:163–172. https://doi.org/10.1016/j.cattod.2014.09.004
Xu L, Liu X, Xu G, Jia W, Ma Y, Zhang Y (2016) Selective hydrodeoxygenation of lignin-derived phenols to cyclohexanols or cyclohexanes over magnetic CoNx@NC catalysts under mild conditions. ACS Catal 6:7611–7620. https://doi.org/10.1021/acscatal.6b01785
Yufeng L, Chuanmin D, Lichao M, Yanan X, Jing G, Shunqiang A, Yuanyuan M, Kan Z (2019) Effect of cobalt addition on the structure and properties of Ni–MCM-41 for the partial oxidation of methane to syngas. RSC Adv 9:508–517. https://doi.org/10.1039/C9RA03534F
Smirniotis PG, Ruckenstein E (1993) Comparison between zeolite β and γ-Al2O3 supported Pt for reforming reactions. J Catal 140(2):526–542. https://doi.org/10.1006/jcat.1993.1103
Sim C, Kui C, Han R (2012) Hydrogen as carbon gasifying agent during glycerol steam reforming over bimetallic Co-Ni catalyst. Adv Mater Phys Chem 2:165–168. https://doi.org/10.4236/ampc.2012.24B043
Yao D, Haiping Y, Chen H (2018) Investigation of nickel-impregnated zeolite catalysts for hydrogen/syngas production from the catalytic reforming of waste polyethylene. Appl Catal B 227(5):477–487. https://doi.org/10.1016/j.apcatb.2018.01.050
Buthainah A, Siti T, Payam A, Zahira Y, Nur Tantiyani A, Wadhah N (2018) Non-supported nickel-based coral sponge-like porous magnetic alloys for catalytic production of syngas and carbon bio-nanofilaments via a biogas decomposition approach. Nanomaterials 8:12. https://doi.org/10.3390/nano8121053
Mante O, Agblevor FA, McClung R (2013) A study on catalytic pyrolysis of biomass with Y-zeolite based FCC catalyst using response surface methodology. Fuel 108:451–464
Thring R, Katikanneni S, Bakhshi NN (2000) The production of gasoline range hydrocrabons from alcell lignin using HZSM-5 catalyst. Fuel Process Technol 62:17
Hajjar R, Millot Y, Man P, Che M, Dzwigaj S (2008) Two kinds of framework Al sites studied in BEA zeolite by X-ray diffraction, fourier transform infrared spectroscopy, NMR techniques, and V Probe. J Phys Chem 112(51):20167–20175. https://doi.org/10.1021/jp808356q
Costa JF, Chica A (2011) Bioethanol steam reforming on Co/ITQ-18 catalyst: effect of the crystalline structure of the delaminated zeolite ITQ-18. Int J Hydrog Energy 36(6):3862–3869
Chica A, Sayas S (2009) Effective and stable bioethanol steam reforming catalyst based on Ni and Co supported on all-silica delaminated ITQ-2 zeolite. Catal Today 146:1–2
Gac W, Greluk M, Slowik G, Millot Y, Valentin L, Dzwigaj S (2018) Effects of dealumination on the performance of Ni-containing BEA catalysts in bioethanol steam reforming. Appl Catal B Environ 237:94–109
Acknowledgements
This study has been supported by funds from the Water and Energy Centre at the United Arab Emirates University (UAEU), fund code: 12R124.
Author information
Ethics declarations
Conflict of Interest
Authors declare that they have no known conflict of interests to declare.
Research Involving Human Participants and/or Animals
Not applicable.
Informed Consent
All authors approve the final version of the manuscript and its submission.
Additional information
Publisher’s Note
Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
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
Yaghi, A., Ali, L., Shittu, T. et al. Hydrodeoxygenation of Vapor Anisole over Nickel/Cobalt and Alumina/Zeolite Supported Catalysts. Catal Surv Asia 28, 48–57 (2024). https://doi.org/10.1007/s10563-023-09409-8
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10563-023-09409-8