Highly Active Aluminosilicates with a Hierarchical Porous Structure for Acetalization of 3,4-dimethoxybenzaldehyde

Authors

  • Hartati Hartati Department of Chemistry, Faculty of Science and Technology, Universitas Airlangga, Surabaya, 60115, Indonesia
  • Didik Prasetyoko Laboratory of Material Chemistry and Energy, Department of Chemistry, Faculty of Mathematics and Natural Sciences, Institut Teknologi Sepuluh Nopember, Surabaya, 60111, Indonesia
  • Mardi Santoso Laboratory of Natural Products and Chemical Synthesis, Department of Chemistry, Faculty of Mathematics and Natural Sciences, Institut Teknologi Sepuluh Nopember, Surabaya, 60111, Indonesia
  • Hasliza Bahruji Cardiff Catalysis Institute, School of Chemistry, Cardiff University, Cf10 3AT, United Kingdom
  • Sugeng Triwahyono Ibnu Sina Institute for Fundamental Science Studies, Universiti Teknologi Malaysia, Johor Bahru, Malaysia

DOI:

https://doi.org/10.11113/jt.v69.3198

Keywords:

Hierarchical porous aluminosilicate, acetalization, 3, 4-dimethoxybenzaldehyde

Abstract

We report the synthesis of highly active mesoporous aluminosilicate for the acetalization of 3,4-dimethoxybenzaldehyde with propylene glycol. The existing synthesis methods for aluminosilicate and ZSM-5 were modified to produce aluminosilicate material with hierarchical porous structure. A combination of two structure directing agents, tetrapropylammonium hydroxide (TPAOH) and cetyltrimethylammonium bromide (CTAB), produced a highly active aluminosilicate framework that provides a wide access for bulky reactants and strong acid sites to catalyse the reaction. The pore structure and the strength of the acid sites were crucial for high conversion of 3,4-dimethoxybenzaldehyde.

References

M. J. Climent, A. Corma, A. Velty. 2004. Synthesis of Hyacinth, Vanilla, and Blossom Orange Fragrances: The Benefit of Using Zeolites and Delaminated Zeolites As Catalysts. Appl. Catal. A. 263: 155–161.

J. Justus, A. Vinu, B.M. Devassy, V.V. Balasubramanian, W. Bohringer, J. Fletcher, S.B. Halligudi. 2008. Highly Efficient and Chemo Selective Catalyst System for the Synthesis of Blossom Orange Fragrance and Flavouring. Catal. Commun. 9: 1671–1675.

S. B. Umbarkar, T. V. Kotbagi, A. V. Biradar, R. Pasrich, J. Chanale, M. K. Dongare, A.S. Mamede, C. Lancelot, E. Payen. 2009. Acetalization of Glycerol Using Mesoporous MoO3/SiO2 Solid Acid Catalyst. J. Mol. Catal. A: Chem. 310: 150–158.

K. Venkatachalam, M. Palanichamy, V. Murugesan. 2010. Acetalization of Heptanal over Al-SBA-1 Molecular Sieve. Catal. Commun. 12: 299–303.

M.J. Climent, A. Corma, A. Velty, M. Susarte. 2000. Zeolites for the Production of Fine Chemicals: Synthesis of the Fructone Fragrancy. J. Catal. 196: 345–351.

L. XueZheng, G. Shan, W. WenJuan, C. WenPing, Y. Jian Guo. 2007. Comparative Research on the Catalytic Activities of Different Molecular sieves for Acetalization and Ketalization, Chin. Sci. Bull. 52(13): 1780–1784.

S. Ajaikumar, A. Pandurangan. 2008, Reaction of Benzaldehyde with Various Aliphatic Glycols in the Presence of Hydrophobic Al-AAM-T-41: A Convenient Synthesis of Cyclic Acetals, J. Mol. Catal. A: Chem. 290: 35–43.

L. L Santos, V.R. Ruiz, M. J. Sabater, A. Corma. 2008. Regioselective Transformation of Alkynes Into Cyclic Acetals and Thioacetals with a Gold(I) Catalyst: Comparison with Brønsted Acid Catalysts. Tetrahedron. 64: 7902–7909.

I. Karame´, M. Alame´, A. Kanj, G.N. Baydoun, H. Hazimeh, M. el Masri, L. Christ. 2011. Mild and Efficient Protection of Diol and Carbonyls as Cyclic Acetals Catalysed by Iron (III) Chloride. C. R. Chimie. 14: 525–529.

M. S. Khayoon, A. Abbas, B. H. Hameed, S. Triwahyono, A. A. Jalil, A.T. Haris, A.I. Minett. 2014. Selective Acetalization of Glycerol with Acetone Over Nickel Nanoparticles Supported on Multi-Walled Carbon Nanotubes. Catal. Lett. 144: 1009–1015.

R.R. Pawar, S.V. Jadhav, C.H. Bajaj. 2013. Microwave-assisted Rapid Valorization of Glycerol Towards Acetals and Ketals. Chem. Eng. J. 235: 61–66.

B. Thomas, F.G. Ramu, S. Gopinath, J. George, M. Kurian, G. Laurent, G.L. Drisko, S. Sugunan. 2011. Catalytic Acetalization of Carbonyl Compounds Over Cation (Ce3+, Fe3+ and Al3+) Exchanged Mont-morillonites and Ce3+-exchanged Y Zeolites. Appl. Clay Sci. 53: 227–235.

A.O. Barros, A.T. Faísca, E.R.. Lachter, R.S.V. Nascimento, R.A.S SanGil, J. Braz. 2011. Acetalization of Hexanal with 2-Ethyl Hexanol Catalyzed by Solid Acids. Chem. Soc. 22(2): 359–363.

V.N. Shetti, J. Kim, R. Srivastava, M. Choi, R. Ryoo. 2008. Assesment of the Mesopore Wall Catalytic Activities of MFI Zeolite with Mesoporous/Microporous Hierarchical Structures. J. Catal. 254: 296–303.

R. Bruckner. 2010. Organic Mechanisms Reactions, Stereochemistry and Synthesis. Springer-Verlag, Berlin Heidelberg.

I. Rodriguez, M.J. Climent, S. Iborra, V. Fornds, A. Corma, A. 2000. Use of Delaminated Zeolites (ITQ-2) and Mesoporous Molecular Sieves in the Production of Fine Chemicals: Preparation of Dimethylacetals and Tetrahydropyranylation of Alcohols and Phenols. J. Catal. 192: 441–447.

M.L. Goncalves, L.D. Dimitrov, M.H. Jorda, M. Wallau, A. Ernesto, U. Gonzalez. 2008. Synthesis of Mesoporous ZSM-5 by Crystallisation of Aged Gels in the Presence of Cetyltrimethylammonium Cations. Catal. Today. 133–135: 69–79.

G. A. Eimer, I. Diaz, E. Sastre, G. S. Casuscelli, M. E. Crivello, E. R. Herrero, J. Periente,J. 2008. Mesoporous Titanosilicates Synthesized from TS-1 Precursors with Enhanced Catalytic Activity in the ï¡-pinene Selective Oxidation. Appl. Catal. A. 343: 77–86.

Y. Cheng, L. J. Wang, J.S. Li, Y.C. Yang, X.Y. Sun. 2005. Preparation and Characterization of Nanosized ZSM-5 Zeolites in the Absence of Organic Template. Mater. Lett. 59: 3427–3430.

C. A. Emeis. 1993. Determination of Integrated Molar Extinction Coefficients for Infrared Absorption Bands of Pyridine Adsorbed on Solid Acid Catalysts. J. Catal. 141(2): 347–354.

K. N. Tayade, M. M. K. Munusamy, R.S. Somani. 2014. Solvent Free Acid Catalyzed Direct N-Alkylation of Amines with Alcohols using Al Grafted AAM-T-41. J. Mol. Catal. A: Chem. In Press.

S. Meenakshi, A.K. Sahu, S.D. Bhat, P. Sridhar, S. Pitchumani, A.K. Shukla. 2013. Mesostructured-aluminosilicate-Nafion Hybrid Membranes for Direct Methanol Fuel Cells. Electrochim. Acta. 89: 35–44.

J. Yang, S. Yu, H. Hu, Y. Zhang, J. Lu, J. Wang, D. Yin. 2011. Synthesis of ZSM-5 Hierarchical Microsphere-like Particle by Two Stage Varying Temperature Crystallization without Secondary Template. Chem. Eng. J. 166: 1083–1089.

M. Thommes. 2010. Physical Adsorption Charac-terization of Nanoporous Materials. Chemie Ingenieur Technik. 82(7) 1059–1073.

F. Jin and Y. Li. 2009. A FTIR and TPD examination of the distributive properties of acid sites on ZSM-5 zeolite with pyridine as a probe molecule. Catal. Today. 145: 101–107.

E. J. M. Hense, D. G. Poduval, V. Degirmenci, D. A. J. M. Ligthart, W. Chen, F. MaugeÌ, M. S. Rigutto, J. A. R. van Veen. 2012. Acidity Characterization of Amorphous Silica−Alumina. J. Phy. Chem. C. 116: 21416−21429.

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Published

2014-07-02

How to Cite

Highly Active Aluminosilicates with a Hierarchical Porous Structure for Acetalization of 3,4-dimethoxybenzaldehyde. (2014). Jurnal Teknologi, 69(5). https://doi.org/10.11113/jt.v69.3198