Sequential Condensation and Hydrodeoxygenation Reaction of Furfural-Acetone Adduct over Mix Catalysts Ni/SiO2 and Cu/SiO2 in Water

https://doi.org/10.22146/ijc.26736

Siti Mariyah Ulfa(1*), Rizka Fauzia Ohorella(2), Caterina Widya Astutik(3)

(1) Department of Chemistry, Faculty of Mathematics and Natural Sciences, Brawijaya University, Jl. Veteran, Malang 65145, Indonesia
(2) Department of Chemistry, Faculty of Mathematics and Natural Sciences, Brawijaya University, Jl. Veteran, Malang 65145, Indonesia
(3) Department of Chemistry, Faculty of Mathematics and Natural Sciences, Brawijaya University, Jl. Veteran, Malang 65145, Indonesia
(*) Corresponding Author

Abstract


Sequential condensation and hydrodeoxygenation reaction were perform using autoclave batch reactor in the presence of water as a solvent. The condensation of furfural and acetone was performed using MgO catalyst followed by hydrodeoxygenation using mix catalyst Ni/SiO2 and Cu/SiO2. The catalyst was prepared by wet-impregnation method and analyzed by XRD, SEM-EDX as well as BET surface. Condensation of furfural and acetone in 1:2 mol ratio was carried out by reflux gave 4-(2-furyl)-3-buten-2-one and 1,5-bis-(2-furanyl)-1,4-pentadien-3-one. The condensation product was then subjected for hydrodeoxygenation using batch reactor, catalyzed by mixed Ni/SiO2 and Cu/SiO2 at 150 and 180 °C for 2 h. The product identified as alkane derivatives with the conversion at 38.83 and 50.35%, respectively. The selectivity of hydrocarbon is 61.39% at 150 °C and 16.55% at 180 °C. Increasing the reaction temperature to 200 °C did not give any products except the recovery of the precursor. It showed that higher temperature enhanced the catalyst activity but the selectivity is controlled by low reaction temperature.

Keywords


hydrodeoxygenation; furfural; condensation; catalyst; liquid phase

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References

[1] Chen, F., Li, N., Li, S., Yang, J., Liu, F., Wang, W., Wang, A., Cong, Y., Wang, X., and Zhang, T., 2014, Solvent-free synthesis of C9 and C10 branched alkanes with furfural and 3-pentanone from lignocellulose, Catal. Commun., 59, 229–232.

[2] Zhao, C., He, J., Lemonidou, A.A., Li, X., and Lercher, J.A., 2011, Aqueous-phase hydrodeoxygenation of bio-derived phenols to cycloalkanes, J. Catal., 280 (1), 8–16.

[3] Lee, E.H., Park, R.S., Kima, H., Park, S.H., Jung, S.C, Jeon, J.K., Kim, S.C., and Park, Y.K., 2016, Hydrodeoxygenation of guaiacol over Pt loaded zeolitic materials, J. Ind. Eng. Chem., 37, 18–21.

[4] Huang, Z., Cui, F., Xue, J., Zuo, J., Chen, J., and Xia, C., 2012, Cu/SiO2 catalysts prepared by hom- and heterogeneous deposition–precipitation methods: Texture, structure, and catalytic performance in the hydrogenolysis of glycerol to 1,2-propanediol, Catal. Today, 183 (1), 42–51.

[5] Huang, Z., Cui, F., Kang, H., Chen, J., Zhang, X., and Xia, C., 2008, Highly dispersed silica-supported copper nanoparticles prepared by precipitation-gel method: A simple but efficient and stable catalyst for glycerol hydrogenolysis, Chem. Mater., 20 (15), 5090–5099.

[6] Ardiyanti, A.R., Khromova, S.A., Venderbosch, R.H., Yakovlev, V.A., and Heeres, H.J., 2012, Catalytic hydrotreatment of fast-pyrolysis oil using non-sulfided bimetallic Ni-Cu catalysts on a δ-Al2O3 support, Appl. Catal., B, 117-118, 105–117.

[7] Ashok, J., Reddy, P.S., Raju, G., Subrahmanyam, M., and Venugopal, A., 2009, Catalytic decomposition of methane to hydrogen and carbon nanofibers over Ni−Cu−SiO2 catalysts, Energy Fuels, 23 (1), 5–13.

[8] Smirnov, A.A., Khromova, S.A., Bulavchenko, O.A., Kaichev, V.V., Saraev, A.A., Reshetnikov, S.I., Bykova, M.V., Trusov, L.I., and Yakovlev, V.A., 2014, Effect of the Ni/Cu ratio on the composition and catalytic properties of nickel-copper alloy in anisole hydrodeoxygenation, Kinet. Catal., 55 (1), 69–78.

[9] Ulfa, S.M., Mahfud, A., Nabilah, S., and Rahman, M.F., 2017, Influence of solvent on liquid phase hydrodeoxygenation of furfural-acetone condensation adduct using Ni/Al2O3-ZrO2 catalyts, IOP Conf. Ser. Mater. Sci. Eng., 172 (1), 012053.

[10] Zaccheria, F., Ravasio, N., Ercoli, M., and Allegrini, P., 2005, Heterogenous Cu-catalyst for the reductive deoxygenation of aromatic ketones without additives, Tetrahedron Lett., 46 (45), 7743–7745.

[11] Ulfa, S.M., Sari, I., Kusumaningsih, C.P., and Rahman, M.F., 2015, Structural properties of Ni/γ-Al2O3 and Cu/γ-Al2O3 catalyst and its application for hydrogenation of furfuylidene acetone, Procedia Chem., 16, 616–622.

[12] Blanco, P.H., Wu, C., and Williams, P.T., 2014, Influence of Ni/SiO2 catalyst preparation methods on hydrogen production from the pyrolysis/reforming of refuse derived fuel, Int. J. Hydrogen Energy, 39 (11), 5723–5732.

[13] Choi, S.G., Wang, S.J., Park, H.H., Jang, J.N., Hong, M.P., Kwon, K.H., and Park, H.H., 2010, Properties of amorphous silicon thin films synthesized by reactive particle beam assisted chemical vapor deposition, Thin Solid Films, 518 (24), 7372–7376.

[14] Hensen, E.J.M., Poduval, D.G., Degirmenci, V., Ligthart, D.A.J.M., Chen, W., Maugé, F., Rigutto, M.S., and van Veen, R.J.A., 2012, Acidity characterization of amorphous silica-alumina, J. Phys. Chem. C, 116 (40), 21416–21429.

[15] Jørgensen, J.E, and Smith R.I., 2006, On the comparison mechanism of FeF3, Acta Crystallogr., Sect. B: Struct. Sci., 62, 987–992.

[16] Lovell, E.C., Scott, J., and Amal, R., 2015, Ni-SiO2 catalysts for the carbon dioxide reforming of methane: Varying support properties by flame spray pyrolysis, Molecules, 20 (3), 4594–4609.

[17] Smith, M.L., Campos, A., and Spivey, J.J., 2012, Reduction processes in Cu/SiO2, Co/SiO2, and CuCo/SiO2 catalysts, Catal. Today, 182 (1), 60–66.

[18] Wu, H.C., Chen, T.C., Wu, J.H., Chen, C.H., Lee, J.F., and Chen, C.S., 2016, The effect of an Fe promoter on Cu/SiO2 catalysts for improving their catalytic activity and stability in the water-gas shift reaction, Catal. Sci. Technol., 6 (15), 6087–6069.

[19] Schmidt, A.A., Eggers, H., Herwig, K., and Anton, R., 1996, Comparative investigation of the nucleation and growth of fcc-metal particles (Rh, Ir, Ni, Pd, Pt, Cu, Ag, Au) on amorphous carbon and SiO2 substrates during vapor deposition at elevated temperatures, Surf. Sci., 349 (3), 301–316.

[20] Lowell, S., Shields, J.E., Thomas, M.A., and Thommes, M., 2004, Characterization of Porous Solids and Powders: Surface Area, Pore Size and Density, Kluwer Academic Publisher, Springer, Dordrecht, Netherlands.



DOI: https://doi.org/10.22146/ijc.26736

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