DOI: https://doi.org/10.9767/bcrec.13.2.1790.311-319

Selective Hydrogenation of Dodecanoic Acid to Dodecane-1-ol Catalyzed by Supported Bimetallic Ni-Sn Alloy

1Department of Chemistry, Faculty of Mathematics and Natural Sciences, Lambung Mangkurat University, Jl. A. Yani Km 36.0 Banjarbaru, South Kalimantan, Indonesia

2Department of Agro-industrial Engineering, Faculty of Agriculture, Lambung Mangkurat University, Jl. A. Yani Km 36.0 Banjarbaru, South Kalimantan, Indonesia

Received: 26 Nov 2017; Revised: 24 Dec 2017; Accepted: 24 Jan 2018; Available online: 11 Jun 2018; Published: 1 Aug 2018.
Editor(s): Istadi Istadi
Open Access Copyright (c) 2018 by Authors, Published by BCREC Group under http://creativecommons.org/licenses/by-sa/4.0.
Fulltext View|Download

Citation Format:
Cover Image
Abstract

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. 

Keywords: Bimetallic Nickel-Tin Alloy Catalyst; Dodecane; Dodecanoic Acid; Dodecane-1-ol; Hydrogenation
Funding: BPDP-Sawit, Ministry of Finances, Republik Indonesia under contract GRK-2016 under contract number PRJ-49/2016

Article Metrics:

Article Info
Section: Original Research Articles
Language : EN
Recent articles
Structural Investigation: Anionic Polymerization of Acrylamide under Microwave Irradiation using Maghnite-Na+ Clay (Algerien MMT) as Initiator Triglycerides Hydrocracking Reaction of Nyamplung Oil with Non-sulfided CoMo/γ-Al2O3 Catalysts Feasibility of Macroporous CeO2 Photocatalysts for Removal of Lead Ions from Water Author Guideline (2017) Frontmatter (Front Cover, Editorial Team, Indexing, and Table of Contents) Backmatter More recent articles
  1. 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
  2. Turek, T., Trimm, D.L., Cant, N.W. (1994). The Catalytic Hydrogenolysis of Esters to Alcohols. Catal. Rev. Sci. Eng. 36: 645-683
  3. Adkins, H., Connor, R. (1931). The Catalytic Hydrogenation of Organic Compounds over Copper Chromite. J. Am. Chem. Soc. 53: 1091-1095
  4. 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
  5. 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
  6. Gallezot, P., Cerino, P.J., Blanc, B., Flèche, G., Fuertes, P. (1994). Glucose Hydrogenation on Promoted Raney-nickel Catalysts. J. Catal. 46: 93-102
  7. 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
  8. 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
  9. Besson, M., Gallezot, P., Pine, C. (2014). Conversion of Biomass into Chemicals over Metal Catalysts. Chem. Rev. 114: 1827-1870
  11. 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
  12. 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
  13. 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
  14. Deshpande, V. M., Patterson, W. R., Narasimhan, C. S. (1990). Studies on Ruthenium-tin Boride Catalysts I. Characterization. J. Catal. 121: 165-173
  15. 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
  16. 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
  17. 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
  18. 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
  19. 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
  20. 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
  21. 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
  22. 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
  23. 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
  24. 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
  25. Powder Diffraction File, JCPDS-International Center for Diffraction Data (ICDDS), 1991
  26. 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
  27. 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
  28. Dandekar, A., Vannice, M.A. (1999). Crotonaldehyde Hydrogenation on Pt/TiO2 and Ni/TiO2 SMSI Catalysts. J. Catal. 183: 344-354
  29. 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
  30. 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

Last update:

No citation recorded.

Last update:

No citation recorded.