DOI: https://doi.org/10.9767/bcrec.9.2.5936.128-135

Catalytic Activities of Fe3+- and Zn2+-Natural Zeolite on the Direct Cyclisation-Acetylation of (R)-(+)-Citronellal

*Edy Cahyono  -  Department of Chemistry, Universitas Negeri Semarang, Sekaran, Gunungpati, Semarang 50229,, Indonesia
Muchalal Muchalal  -  Department of Chemistry, Gadjah Mada University, Sekip Utara, Yogyakarta 55281,, Indonesia
Triyono Triyono  -  Department of Chemistry, Gadjah Mada University, Sekip Utara, Yogyakarta 55281,, Indonesia
Harno Dwi Pranowo  -  Department of Chemistry, Gadjah Mada University, Sekip Utara, Yogyakarta 55281,, Indonesia

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Abstract

Characterisation and catalytic ativities investigation of modified natural zeolite on cyclisation acetylation reaction of (R)-(+)-citronellal was performed. The experimental work involved isolation of (R)-(+)-citronellal from Java Citronella oil (Cymbopogon winterianus) by vacuum fractional distillation, determination of its enantiomer, preparation and characterisation of different catalysts i.e. H-natural zeolite (H-Za), Fe3+-natural zeolite (Fe3+-Za), and Zn2+-natural zeolite (Zn2+-Za), followed by examination of catalytic activity and selectivity. Isolated citronellal contained 88.21% ee of (R)-(+)-citronellal. The main products of cyclisation-acetylation of (R)-(+)-citronellal was IPA (isopulegyl acetate) and NIPA (neo-isopulegyl acetate). Although the highest yield of IPA and NIPA was obtained by Fe3+-Za catalyst (78.69%) at 80oC and 120 min, the stereoselectivity of Fe3+-Za slightly lower than that of Zn2+-Za. Structure elucidation of citronellal and products was carried out by means of GC and GC-MS. Lewis acidity plays the role of acetyl ionic formation from acetic anhydride. The Activity and stereoselectivity of catalysts depended on Lewis acidity and cation distribution on the catalyst surface. © 2014 BCREC UNDIP. All rights reserved

Received: 18th December 2013; Revised: 9th April 2014; Accepted: 17th April 2014

[ How to Cite: Cahyono, E., Muchalal, M., Triyono, T., Pranowo, H.D. (2014). Catalytic Activities of Fe3+- and Zn2+-Natural Zeolite on the Direct Cyclisation-Acetylation of (R)-(+)-Citronellal. Bulletin of Chemical Reaction Engineering & Catalysis, 9 (2): 128-135. (doi:10.9767/bcrec.9.2.5936.128-135) ]

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Keywords: (R)-(+)-citronellal; isopulegyl acetate; Fe3+ and Zn2+-natural zeolite

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Language : EN
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  8. Chuah, G.K., Liu, S.H., Jaenicke, S., Harrison, L.J. (2001). Cyclization Citronellal to Isopulegol Catalyzed by Hydrous Zirconia and Other Solid Acids. J. Catal. 200: 352-359
  9. Yongshong, Z., Yuntong, N., Jaenicke, S., Chuah, G.K. (2004). Cyclisation of Citronellal over Zirconium Zeolite beta - a Highly Diastereoselective Catalyst to (±)-Isopulegol. J. Catal. 229: 404-413
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  11. Delannay, F. (1984). Characterization of heterogeneous catalysis; Marcel Dekker: New York
  12. Maria, C., Abello, M.C., Velasco, V.P., Go-mez, M.F., Rivarola, J.B. (1997). Temperature-Programmed Desorption of NH3 on Na-Y Zeolite. Langmuir. 13: 2596-2599
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  16. Hernáandez, M.A., Corona, L., Rojas, F. (2000). Adsorption Characteristics of Natural Erionite, Clinoptilolite and Mordenite Zeolites from Mexico. Adsorption. 6(1): 33-45
  17. Xi, H., Li, Z., Zhang, H. Li, X., Hu, X. (2003). Estimation of Activation Energy For Desorption of Low-Volatility Dioxins on Zeolites By TPD Technique. Sep. Purif. Technol. 31: 41-45
  18. Mockovciakova, A., Matik, M., Zuzana Orolınova, Z, Hudec, P., Kmecova, E. (2008). Structural characteristics of modified natural zeolite. J. Porous Mater. 15: 559-564
  19. Guisnet, M., Ayrault, P., Coutanceau, C., Alvarez, M.F., Datka, J. (1997). Acid Properties of Dealuminated Beta Zeolites Studied by Irspectroscopy. J. Chem. Soc. Faraday Trans. 93: 1661-1665
  20. Sharma, P., Rajaram, P., Thomar, R. (2008). Synthesis And Morphological Studies of Nanocrystalline MOR Type Zeolite Material. J. Colloid Interf. Sci. 325: 547-557
  21. Freese, U., Heinrich F., Roessner, F. (1999). Acylation of Aromatic Compounds on H-Beta zeolites, Catal. Today. 49(1-3): 237-244
  22. Smith, K., Zenhua, Z., Hodgson, P.K.G. (1998). Synthesis of Aromatic Ketones by Acylation of Aryl Ethers with Carboxylic Anhy-drides in the Presence of Zeolite H-Β (H-BEA) in the Absence of Solvent. J. Mol. Cat. A-Chem. 134: 121-128
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  24. Liu, Y., Lotero, E., Goodwin Jr., J.G. (2006). Effect of Carbon Chain Length on Esterification of Carboxylic Acids with Methanol Using Acid Catalysis. J. Catal. 243: 221-228

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