Selective Hydrogenation of Dodecanoic Acid to Dodecane-1-ol Catalyzed by Supported Bimetallic Ni-Sn Alloy
Copyright (c) 2018 Bulletin of Chemical Reaction Engineering & Catalysis
This work is licensed under a Creative Commons Attribution-ShareAlike 4.0 International License.
Article Metrics: (Click on the Metric tab below to see the detail)
Selective hydrogenation of dodecanoic acid over supported bimetallic Ni-Sn alloy catalysts into dodecane-1-ol is demonstrated. Bimetallic nickel-tin supported on titanium oxide (Ni-Sn(1.5)/TiO2) and gamma-alumina (Ni-Sn(1.5)/g-Al2O3); 1.5 = Ni/Sn molar ratio) were synthesized via hydrothermal method in a sealed-Teflon autoclave reactor at 150 oC for 24 h, then followed by reducing with hydrogen gas at 400 oC for 1.5 h. The synthesized catalysts were characterized by means of XRD, IC-AES, N2-adsorption (BET method), H2-chemisorption, and NH3-TPD. Bimetallic Ni-Sn(1.5)/TiO2 catalyst was found to be effective for hydrogenation of dodecanoic acid (>99 % conversion) to dodecane-1-ol (93% yield) at 160 oC, 30 bar H2, and 20 h and the highest dodecane-1-ol (97 % yield) was obtained at initial pressure of H2, 50 bar. An increase of reaction temperature slightly enhanced the degree of hydrodeoxygenation of dodecanoic acid to produce dodecane over both Ni-Sn(1.5)/TiO2 and Ni-Sn(1.5)/g-Al2O3 catalysts. Copyright © 2018 BCREC Group. All rights reserved
Received: 26th November 2017; Revised: 24nd December 2017; Accepted: 24th January 2018; Available online: 11st June 2018; Published regularly: 1st August 2018
How to Cite: Rodiansono, R. Pratama, M.I., Astuti, M.D., Abdullah, A., Nugroho, A., Susi, S. (2018). Selective Hydrogenation of Dodecanoic Acid to Dodecane-1-ol Catalyzed by Supported Bimetallic Ni-Sn Alloy. Bulletin of Chemical Reaction Engineering & Catalysis, 13 (2): 311-319 (doi:10.9767/bcrec.13.2.1790.311-319)
- Biermann, U., Bornscheuer, U., Meier, M.A.R., Metzger, J.O., Schafer, H.J. (2011). Oils and Fats as Renewable Raw Materials in Chemistry. Angew. Chem., Int. Ed. 50: 3854-3871.
- Turek, T., Trimm, D.L., Cant, N.W. (1994). The Catalytic Hydrogenolysis of Esters to Alcohols. Catal. Rev. Sci. Eng. 36: 645-683.
- Adkins, H., Connor, R. (1931). The Catalytic Hydrogenation of Organic Compounds over Copper Chromite. J. Am. Chem. Soc. 53: 1091-1095.
- Rozmysłowicz, B., Kirilin, A., Aho, A., Manyar, H.G., Hardacre, C., Warna, J., Salmi, T., Murzin, D.Y. (2015). Selective Hydrogenation of Fatty Acids to Alcohols over Highly Dispersed ReOx/TiO2 Catalyst. J. Catal. 328: 197-207.
- Manyar, H.G., Paun, C., Rilus, R., Rooney, D.W., Thompson, J.M., Hardacre, C. (2010). Highly Selective and Efficient Hydrogenation of Carboxylic Acids to Alcohols using Titania Supported Pt Catalysts. Chem. Commun. 46: 6279-6281.
- Gallezot, P., Cerino, P.J., Blanc, B., Flèche, G., Fuertes, P. (1994). Glucose Hydrogenation on Promoted Raney-nickel Catalysts. J. Catal. 46: 93-102.
- Alonso, D.M., Wettstein, S.G., Dumesic, J.A. (2012). Bimetallic Catalysts for Upgrading of Biomass to Fuels and Chemicals. Chem. Soc. Rev. 41: 8075-8098.
- Pritchard, J., Filonenko, G.A., van Putten, R., Hensen, E.J.M., Pidko, E.A. (2015). Heterogeneous and Homogeneous Catalysis for the Hydrogenation of Carboxylic Acid Derivatives: History, Advances and Future Directions, Chem. Soc. Rev. 44: 3808-3833.
- Besson, M., Gallezot, P., Pine, C. (2014). Conversion of Biomass into Chemicals over Metal Catalysts. Chem. Rev. 114: 1827-1870.
- Huang, C., Zhang, H., Zhao, Y., Chen, S., Liu, Z. (2012). Diatomite-supported Pd-M (M = Cu, Co, Ni) Bimetal Nanocatalysts for Selective Hydrogenation of Long-chain Aliphatic Esters. J. Coll. Interface Sci. 386: 60-65.
- Shao, Y., Xia, Q., Liu, X., Lu, G., Wang, Y. (2015). Pd/Nb2O5/SiO2 Catalyst for the Direct Hydrodeoxygenation of Biomass-related Compounds to Liquid Alkanes under Mild Conditions. ChemSusChem. 8: 1761-1767.
- Miyake, T., Makino, T., Taniguchi, S. I., Watanuki, H., Niki, T., Shimizu, S., Kojima, Y., Sano, M. (2009). Alcohol Synthesis by Hydrogenation of Fatty Acid Methyl Esters on Supported Ru–Sn and Rh–Sn Catalysts. Appl. Catal. A. 364: 108-112.
- Deshpande, V. M., Patterson, W. R., Narasimhan, C. S. (1990). Studies on Ruthenium-tin Boride Catalysts I. Characterization. J. Catal. 121: 165-173.
- Deshpande, V.M., Ramnarayan, K., Narasimhan, C.S. (1990). Studies on Ruthenium-tin Boride Catalysts II. Hydrogenation of Fatty Acid Esters to Fatty Alcohols. J. Catal. 21: 174-182.
- Rodiansono, R., Hara, T., Ichikuni, N., Shimazu, S. (2012). Highly Eﬃcient and Selective Hydrogenation of Unsaturated Carbonyl Compounds using Ni–Sn Alloy Catalysts. Catal. Sci. Technol. 2: 2139-2145.
- Rodiansono, R., Hara, T., Ichikuni, N., Shimazu, S. (2012). A Novel Preparation Method of Ni-Sn Alloy Catalysts Supported on Aluminium Hydroxide: Application to Chemoselective Hydrogenation of Unsaturated Carbonyl Compounds. Catal. Lett. 41(8): 769-771.
- Rodiansono, R., Hara, T., Ichikuni, N., Shimazu, S. (2014). Development of Nanoporous Ni-Sn Alloy and Application for Chemoselective Hydrogenation of Furfural to Furfuryl Alcohol. Bull. Chem. React. Eng. Catal. 9(1): 53-59
- Rodiansono, R., Ghofur, A., Astuti, M.D., Sembiring, K.C. (2015). Catalytic Hydrogenation of Levulinic Acid in Water into g-Valerolactone over Bulk Structure of Inexpensive Intermetallic Ni-Sn Alloy Catalysts. Bull. Chem. React. Eng. Catal. 10(2): 192-200.
- Rodiansono, R., Astuti, M.D., Hara, T., Ichikuni, N., Shimazu, S. (2016). Efficient Hydrogenation of Levulinic Acid in Water using a Supported Ni-Sn Alloy on Aluminium Hydroxide Catalysts. Catal. Sci. Technol. 6: 2955-2961.
- Lowell, S., Shields, J. E., Thomas, M. A., Thommes, M. (2004). Characterization of Porous Solids and Powders: Surface Area, Pore Size and Density, Kluwer Academic Publishers, Netherlands, Chapter 8.
- Bartholomew, C.H., Pannel, R.B., Butler, J.L. (1980). Support and Crystallite Size Effects in CO Hydrogenation on Nickel. J. Catal. 65: 335-347.
- Bartholomew, C.H., Pannel, R.B. (1980). The Stoichiometry of Hydrogen and Carbon Monoxide Chemisorption on Alumina- and Silica-supported Nickel. J. Catal. 65: 390-401.
- Rodiansono, R., Astuti, M.D., Khairi, S., Shimazu, S. (2016). Selective Hydrogenation of Biomass-derived Furfural over Supported Ni3Sn2 Alloy: Role of Supports. Bull. Chem. React. Eng. Catal. 11(1): 1-9.
- Powder Diffraction File, JCPDS-International Center for Diffraction Data (ICDDS), 1991.
- Dumitriu, E., Hulea, V.J. (2003) Effects of Channel Structures and Acid Properties of Large Pore Zeolites in the Liquid Phase Tert-butylation of Phenol. J. Catal. 218: 249-257.
- Khandan, N., Kazemeini, M., Aghaziarati, M. (2008). Determining an Optimum Catalyst for Liquid Phase Dehydration of Methanol to Dimethyl Ether. J. Appl. Catal. A.349: 6-12.
- Dandekar, A., Vannice, M.A. (1999). Crotonaldehyde Hydrogenation on Pt/TiO2 and Ni/TiO2 SMSI Catalysts. J. Catal. 183: 344-354.
- Sordelli, L., Psaro, R., Vlaic, G., Cepparo, A., Recchia, S., Fusi, A., Zanoni, R. (1999). EXAFS Studies of Supported Rh–Sn Catalysts for Citral Hydrogenation. J. Catal. 182: 186-198.
- Margitfalvi, J. L., Tompos, A., Kolosova, I., Valyon, J. (1998). Reaction Induced Selectivity Improvement in the Hydrogenation of Crotonaldehyde over Sn-Pt/SiO2 Catalysts. J. Catal. 174: 246-249.
This work is licensed under a Creative Commons Attribution-ShareAlike 4.0 International License.
Authors and readers can copy and redistribute the material in any medium or format, as well as remix, transform, and build upon the material for any purpose, even commercially, but they must give appropriate credit (cite to the article or content), provide a link to the license, and indicate if changes were made. If you remix, transform, or build upon the material, you must distribute your contributions under the same license as the original.
Copyright Transfer Agreement
The Authors submitting a manuscript do so on the understanding that if accepted for publication, copyright of the article shall be assigned to Bulletin of Chemical Reaction Engineering & Catalysis journal and Department of Chemical Engineering Diponegoro University as publisher of the journal.
Copyright encompasses exclusive rights to reproduce and deliver the article in all form and media, including reprints, photographs, microfilms and any other similar reproductions, as well as translations. The reproduction of any part of this journal, its storage in databases and its transmission by any form or media, such as electronic, electrostatic and mechanical copies, photocopies, recordings, magnetic media, etc., will be allowed only with a written permission from Bulletin of Chemical Reaction Engineering & Catalysis journal and Department of Chemical Engineering Diponegoro University.
Bulletin of Chemical Reaction Engineering & Catalysis journal and Department of Chemical Engineering Diponegoro University, the Editors and the Advisory International Editorial Board make every effort to ensure that no wrong or misleading data, opinions or statements be published in the journal. In any way, the contents of the articles and advertisements published in the Bulletin of Chemical Reaction Engineering & Catalysis are sole and exclusive responsibility of their respective authors and advertisers.
The Copyright Transfer Form can be downloaded here: [Copyright Transfer Form BCREC 2016]
The copyright form should be signed originally and send to the Editorial Office in the form of original mail, scanned document or fax :
Prof. Dr. I. Istadi (Editor-in-Chief)
Editorial Office of Bulletin of Chemical Reaction Engineering and Catalysis
Department of Chemical Engineering, Diponegoro University
Jl. Prof. Soedarto, Kampus Undip Tembalang, Semarang, Central Java, Indonesia 50275
Telp.: +62-24-7460058, Fax.: +62-24-76480675