Abstract
A mixed metal-oxide (NiAlOx) obtained from the annealing of a synthetic takovite clay, [(Ni6Al2(OH)16]CO3·4H2O, was used as a catalyst in the hydrodeoxygenation reaction of vanillin, as a model molecule, to simulate deoxygenation of lignin's moieties. The catalysts were characterized by XRD, TPR, XPS and textural analyses and were tested at between 413 and 573 K and 1.2 MPa H2, using a 300 ml batch reactor. The reaction products were analyzed using a gas-chromatograph coupled to a mass detector (GC–MS). The active site is visualized as a Niδ+–O–Al3+ moieties able to dissociate molecular H2 into highly reactive species (H− and H+) for hydrogenation reactions. Depending on the reaction temperature, decarbonylation, hydrogenation, demethoxylation and dehydroxylation reactions occurred in three stages as clearly indicated by Van-Krevelen O/C* vs. H/C* plots. Our study points out that total deoxygenation can be attained at 553 K with a 100% selectivity to products like methyl-cyclohexane and cyclohexane.
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Bridgwater AC (2012) Review of fast pyrolysis of biomass and product upgrading. Biomass Bioenergy 38:68–94
Maggi R, Delmon B (1992). In: Bridgwater AV (ed) Advances in thermochemical biomass conversion. Blackie, London, p 1086
Furimsky E (2000) Catalytic hydrodeoxygenation . Appl Catal A 199:147–190
Wang H, Male J, Wang Y (2013) Recent advances in hydrotreating of pyrolysis bio-oil and its oxygen-containing model compounds. ACS Catal 3:1047–1070
González BMA, Resasco DE (2011) Anisole and guaiacol hydrodeoxygenation over monolithic Pt–Sn catalysts. Energy Fuels 25:4155–4162
Bykova MV, Bulavchenko OA, Ermakov DY, Lebedev MY, Yakovlev VA, Parmon VN (2011) Guaiacol hydrodeoxygenation in the presence of Ni-containing catalysts. Catal Ind 3:15–22
Olcese RN, Bettahar M, Petitjean D, Malaman B, Giovanella F, Dufour A (2012) Gas-phase hydrodeoxygenation of guaiacol over Fe/SiO2 catalyst. Appl Catal B 115:63–73
Nimmanwudipong T, Runnebaum T, Block DE, Gates BC (2011) Catalytic conversion of guaiacol catalyzed by platinum supported on alumina: reaction network including hydrodeoxygenation reactions. Energy Fuels 25:3417–3427
Sturgeon MR, O’Brien MH, Ciesielski PN, Katahira R, Kruger JS, Chmely SC, Hamlin J, Lawrence K, Hunsinger GB, Foust TD, Baldwin RM, Biddy MJ, Beckham GT (2014) Lignin depolymerisation by nickel supported layered-duoble hydroxide catalysts. Green Chem 16:824–835
Huang X, Atay C, Korányi TI, Boot MD, Hensen EJM (2015) Lignin depolymerisation by nickel supported layered-double hydroxide catalysts. ACS Catal 5:7359–7370
Lamonier C, Ponchel A, Huysser AD, Jalowiecki-Duhamel L (1999) Studies of the cerium-metal-oxygen-hydrogen system (metal = Cu, Ni). Catal Today 50:247–259
Sohier MP, Wrobel G, Bonnelle JP, Marcq JP (1992) Hydrogenation catalysts based on nickel and rare earths oxides: I. Relation between cations nature, preparation route, hydrogen content and catalytic activity. Appl Catal A 84:169–186
Wrobel G, Lamonier C, Bennani A, D’Huysser A, Aboukaïs A (1996) Effect of incorporation of copper or nickel on hydrogen storage in ceria. Mechanism of reduction. J Chem Soc Faraday Trans 92:2001–2009
He L, Qin Y, Lou H, Chen P (2015) Highly dispersed molybdenum carbide nanoparticles supported on activated carbon as an efficient catalyst for the hydrodeoxygenation of vanillin. RSC Adv 5:43141–43147
Yati I, Yoon AA, Choi JS, Suh JW, Jae DJ, Ha JM (2016) One-pot catalytic reaction to produce high-carbon-number dimeric deoxygenated hydrocarbons from lignin-derived monophenyl vanillin using Al2O3-cogelled Ru nanoparticles. Appl Catal A 524:243–250
Kayalvizhi J, Pandurangan A (2017) Hydrodeoxygenation of vanillin using palladium on mesoporous KIT-6 in vapour phase reactor. Mol Catal 436:67–77
Valente JS, Lopez SE, Sanchez CM (2010), US Patent 7,807,128B2 to Instituto Mexicano del Petróleo
Valente JS, Sanchez CM, Figueras F (2008) A simple environmentally friendly method to prepare versatile hydrotalcite-like compounds. Chem Mater 20:1230–1232
Valente JS, Sanchez CM, Lima E, Figueras F (2009) Method for large scale production of multimetallic layered double hydroxides: formation mechanism discernment. Chem Mater 21:5809–5818
Cavani F, Trifirò F, Vaccari A (1991) Hydrotalcite-type anionic clays: preparation, properties and applications. Catal Today 11:173–301
Clause O, Rebours B, Merlen E, Trifiró F, Vaccari A (1992) Preparation and characterization of nickel-aluminum mixed oxides obtained by thermal decomposition of hydrotalcite-type precursors. J Catal 133:231–246
Bellezza F, Cipiciani A, Costantino U, Nocchetti M, Posati T (2009) Hydrotalcite-like nanocrystals from water-in-oil microemulsions. Eur J Inorg Chem 2009:2603–2611
Benito P, Labajos FM, Rives V (2006) Microwave-treated layered double hydroxides containing Ni2+and Al3+: the effect of added Zn2+. J Solid State Chem 179:3784–3797
Aramendía MA, Borau V, Jiménez C, Marinas JM, Ruiz JR, Urbano FJ (2002) Comparative study of Mg/M(III) (M = Al, Ga, In) layered double hydroxides obtained by coprecipitation and the sol–gel method. J Solid State Chem 168:156–161
Bian L, Wang W, Xia R, Li Z (2016) Ni-based catalyst derived from Ni/Al hydrotalcitelike compounds by the urea hydrolysis method for CO methanation. RSC Adv 6:677–686
Alejandre A, Medina F, Rodriguez X, Salagre P, Cesteros Y, Sueiras J (2001) Cu/Ni/Al layered double hydroxides as precursors of catalysts for the wet air oxidation of phenol aqueous solutions. Appl Catal B 30:195–207
Magrini-Bair KA et al (2007) Fluidizable reforming catalyst development for conditioning biomass-derived syngas. Appl Catal A 318:199–206
Peck MA, Langell MA (2012) Comparison of nanoscaled and bulk NiO structural and environmental characteristics by XRD, XAFS, and XPS. Chem Mater 24:4483–4490
Measurement Services Division of the National Institute of Standards and Technology (NIST) (2012) Identify Unknown Spectral Lines. Julio, 2019, de U.S. Department of Commerce. https://srdata.nist.gov/xps/EnergyTypeValSrch.aspx
Gao D, Xiao Y, Varma A (2015) Guaiacol hydrodeoxygenation over platinum catalyst: reaction pathways and kinetics. Ind Eng Chem Res 54:10638–10644
Zhu Z, Tan H, Wang J, Yu S, Zhou K (2014) Hydrodeoxygenation of vanillin as a bio-oil model over carbonaceous microspheres-supported Pd catalysts in the aqueous phase and Pickering emulsions. Green Chem 16:2636–2643
Bindwal AB, Vaidya PD (2014) Reaction kinetics of vanillin hydrogenation in aqueous solutions using a Ru/C catalyst. Energy Fuels 28:3357–3362
Singh AK et al (2015) One-pot defunctionalization of lignin-derived compounds by dual-functional Pd50Ag50/Fe3O4/N-rGO catalyst. ACS Catal 5:6964–6972
Jimaré MT et al (2013) Modelling of experimental vanillin hydrodeoxygenation reactions in water/oil emulsions. Effects of mass transport. Catal Today 210:89–97
Yang X, Liang Y, Cheng Y, Song W, Wang X, Wang Z, Qiu J (2014) Hydrodeoxygenation of vanillin over carbon nanotube-supported Ru catalysts assembled at the interfaces of emulsion droplets. Catal Commun 47:28–31
Mortensen PM, Grunwaldt J-D, Jensen PA, Jensen AD (2013) Screening of catalysts for hydrodeoxygenation of phenol as a model compound for bio-oil. ACS Catal 3:1774–1785
Huynh MT, Armbruster U, Nguyen LH, Nguyen DA, Martin A (2015) Hydrodeoxygenation of bio-oil on bimetallic catalysts: from model compound to real feed. J Sustain Bioenergy Syst 5:151–160
Foster AJ, Do PT, Lobo RF (2012) The synergy of the support acid function and the metal function in the catalytic hydrodeoxygenation of m-cresol. Top Catal 55:118–128
Benito P, Guinea I, Labajos FM, Rives V (2008) Microwave-assisted reconstruction of Ni,Al hydrotalcite-like compounds. J Solid State Chem 181:987–996
Clause O, Goncalves Coelho M, Gazzano M, Matteuzzi D, Trifiró F, Vaccari A (1993) Synthesis and thermal reactivity of nickel containing anionic clays. Appl Clay Sci 8:169–186
Jalowiecki-Duhamel L (2006) Hydrogen storage and induced properties in non-metallic catalytic materials. Int J Hydrogen Energy 31:191–195
Jalowiecki-Duhamel L, Carpentier J, Ponchel A (2007) Catalytic hydrogen storage in cerium nickel and zirconium (or aluminium) mixed oxides. Int J Hydrogen Energy 32:2439–2444
Rudolf C, Dragoi B, Ungureanu A, Chirieac A, Royer S, Nastro A, Dumitriu E (2014) NiAl and CoAl materials derived from takovite-like LDHs and related structures as efficient chemoselective hydrogenation catalysts. Catal Sci Technol 4:179–189
Bykova MV, Zavarukhin SG, Trusov LI, Yakovlev VA (2013) Guaiacol hydrodeoxygenation kinetics with catalyst deactivation taken into consideration. Kinet Catal 54:40–48
Su-Ping Z (2003) Study of hydrodeoxygenation of bio-oil from the fast pyrolysis of biomass. Energy Sources 25:57–65
Funding
This research is a product of Project D.60048 “Desarrollo de un proceso catalítico para la obtención de compuestos aromáticos a partir de lignina” funded by Mexican Institute of Petroleum.
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Vázquez-Fuentes, L.F., Cortés-Jacome, M.A., López-Salinas, E. et al. Selective Vanillin Hydrodeoxygenation on Synthetic Takovite Derived NiAlOx Mixed Oxide. Top Catal 63, 428–436 (2020). https://doi.org/10.1007/s11244-020-01261-8
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DOI: https://doi.org/10.1007/s11244-020-01261-8