Cesium Tungstophosphoric Acid Supported on Fly Ash: The Solid Catalyst for Esterification of Eugenol with Acetic Acid

Abstract:

Eugenyl acetate is used in various industries including the pharmaceutical industry, the food and beverage industry, the vegetable pesticide industry, as well as a bio-additive fuel. Eugenyl acetate can be obtained synthetically by esterification of eugenol and acetic acid using an acid catalyst. The purpose of this study was to examine the heterogeneous catalyst CsTPA supported by fly ash for the esterification reaction of eugenol to eugenyl acetate. CsTPA was prepared at the impregnation time (4,8, and 12 hours) and the calcination temperature (300, 400 and 500°C). Calcination temperature and impregnation time have little effect on the catalytic structure, except on the porosity of the solid catalyst. The catalytic activity was conducted by synthesizing eugenyl acetate. The conversion results for eugenyl acetate were not substantially different at about 75-80 per cent. CSTPA/fly ash tends to be an alternate solid catalyst for eugenyl acetate production.

• Periodical: Materials Science Forum (Volume 1029)
• Pages: 197-204
• DOI: https://doi.org/10.4028/www.scientific.net/MSF.1029.197
• Online since: May 2021
• Authors: Nur Hidayati*, Fertaria Utama Agus, Diana Safitri
• Keywords: Esterification, Eugenyl Acetate, Fly Ash, Solid Catalyst

References

[1] P. dos Santos, G. L. Zabot, M. A. A. Meireles, M. A. Mazutti, and J. Martínez, Synthesis of eugenyl acetate by enzymatic reactions in supercritical carbon dioxide,, Biochem. Eng. J., vol. 114, p.1–9, (2016).

DOI: 10.1016/j.bej.2016.06.018

[2] B. Tepe, E. Donmez, M. Unlu, F. Candan, and D. Daferera, Antimicrobial and antioxidative activities of the essential oils and methanol extracts of Salvia cryptantha ( Montbret et Aucher ex Benth .) and Salvia multicaulis ( Vahl ),, Food Chem., vol. 84, p.519–525, (2004).

DOI: 10.1016/s0308-8146(03)00267-x

[3] L. A. Lerin et al., Continuous ion-exchange resin catalysed esterification of eugenol for the optimized production of eugenyl acetate using a packed bed microreactor,, RSC Adv., vol. 5, no. 94, p.76898–76903, (2015).

DOI: 10.1039/c5ra08457a

[4] A. Kadarohman, Hernani, F. Khoerunisa, and R. M. Astuti, A Potential Study on Clove Oil , Eugenol and Eugenyl Acetate As Diesel Fuel Bio-Additives and Their Performance on One Cylinder Engine,, J. Transp., vol. 25, no. 1, p.66–76, (2010).

DOI: 10.3846/transport.2010.09

[5] A. Valério et al., Synthesis of eugenyl acetate through heterogeneous catalysis,, J. Essent. Oil Res., vol. 31, no. 4, p.312–318, (2019).

[6] D. A. Laroque et al., Synthesis of Eugenyl Acetate in Solvent-Free Acetylation : Process Optimization and Kinetic Evaluation Chemical Engineering & Process Technology Synthesis of Eugenyl Acetate in Solvent-Free Acetylation : Process Optimization and Kinetic Evaluation,, J. Chem. Eng. Process Technol., no. October, (2019).

DOI: 10.4172/2157-7048.1000247

[7] S. Mat Radzi, M. Z. R. Hanif, and K. M. W. Syamsul, Optimization of Eugenol Ester Using Statistical Approach of Response Surface Methodology,, Mater. Sci. Forum, vol. 857, p.469–474, (2016).

DOI: 10.4028/www.scientific.net/msf.857.469

[8] P. Gupta and S. Paul, Solid acids: Green alternatives for acid catalysis,, Catal. Today, vol. 236, no. PART B, p.153–170, (2014).

DOI: 10.1016/j.cattod.2014.04.010

[9] M. Pillinger, A. A. Valente, and A. S. Dias, Acidic cesium salts of 12-tungstophosphoric acid as catalysts for the dehydration of xylose into furfural,, vol. 341, p.2946–2953, (2006).

DOI: 10.1016/j.carres.2006.10.013

[10] C. R. Ward, D. French, J. Jankowski, M. Dubikova, Z. Li, and K. W. Riley, Element mobility from fresh and long-stored acidic fly ashes associated with an Australian power station,, Int. J. Coal Geol., vol. 80, no. 3–4, p.224–236, (2009).

DOI: 10.1016/j.coal.2009.09.001

[11] C. Ferreira et al., Y zeolite-supported niobium pentoxide catalysts for the glycerol acetylation reaction,, Microporous Mesoporous Mater., vol. 271, p.243–251, (2018).

DOI: 10.1016/j.micromeso.2018.06.010

[12] R. Purova et al., Journal of Molecular Catalysis A : Chemical Pillared HMCM-36 zeolite catalyst for biodiesel production by esterification of palmitic acid," ,Journal Mol. Catal. A, Chem., vol. 406, p.159–167, (2015).

DOI: 10.1016/j.molcata.2015.06.006

[13] E. Indarti, Hydrated calcined Cyrtopleura costata seashells as an effective solid catalyst for microwave-assisted preparation of palm oil biodiesel,, ENERGY Convers. Manag., vol. 117, p.319–325, (2016).

DOI: 10.1016/j.enconman.2016.03.030

[14] I. Korkut and M. Bayramoglu, Ultrasound assisted biodiesel production in presence of dolomite catalyst,, Fuel, vol. 180, p.624–629, (2016).

DOI: 10.1016/j.fuel.2016.04.101

[15] S. Zhao et al., Experimental investigation on biodiesel production through transesterification promoted by the La-dolomite catalyst,, Fuel, vol. 257, p.116092, (2019).

DOI: 10.1016/j.fuel.2019.116092

[16] M.S. Kotwal, P.S. Niphadkar, S.S. Deshpande, V.V. Bokade, and P.N. Joshi, Transesterification of sunflower oil catalyzed by flyash-based solid catalysts,, Fuel, vol. 88, no. 9, p.1773–1778, (2009).

DOI: 10.1016/j.fuel.2009.04.004

[17] M. C. Manique, L. V. Lacerda, A. K. Alves, and C. P. Bergmann, Biodiesel production using coal fly ash-derived sodalite as a heterogeneous catalyst,, Fuel, vol. 190, p.268–273, (2017).

DOI: 10.1016/j.fuel.2016.11.016

[18] N. A. Mazumder, R. Rano, and G. Sarmah, A green and efficient solid acid catalyst from coal fly ash for Fischer esterification reaction,, J. Ind. Eng. Chem., vol. 32, p.211–217, (2015).

DOI: 10.1016/j.jiec.2015.08.020

[19] A. Sharma, S. Kabra, S. Katara, and A. Rani, Acid activated fly ash , as a novel solid acid catalyst for esterification of aetic acid,, Indian J. Appl. Res., vol. 3, no. 4, p.37–39, (2013).

DOI: 10.15373/2249555x/apr2013/12

[20] R. D. Rieke, D. S. Thakur, B. D. Roberts, and G. T. White, to Fatty Alcohol Part I : Correlation Between Catalyst Properties and Activity / Selectivity,, vol. 74, no. 4, p.333–339, (1997).

DOI: 10.1007/s11746-997-0088-y

[21] A. Altomare, N. Corriero, C. Cuocci, A. Falcicchio, and R. Rizzi, QUALX2 . 0 : A qualitative phase analysis software using the freely available database POW-COD QUALX2 . 0 : a qualitative phase analysis software using the freely available database POW _ COD,, J. Appl. Crystallogr., vol. 48, no. April, p.598–603, (2015).

DOI: 10.1107/s1600576715002319

[22] O. Babajide, L. Petrik, N. Musyoka, B. Amigun, and F. Ameer, Use of Coal Fly Ash As a Catalyst in the Production of Biodiesel,, Pet. Coal, vol. 52, no. 4, p.261–272, (2010).

DOI: 10.1016/j.cattod.2012.04.044

[23] D. A. Laroque, R. A. L. Maria JA Silva, and G. N. Pereira, Synthesis of Eugenyl Acetate in Solvent-Free Acetylation: Process Optimization and Kinetic Evaluation,, J. Chem. Eng. Process Technol., vol. 06, no. 04, p.4–11, (2015).

DOI: 10.4172/2157-7048.1000247

[24] M. J. A. Silva et al., Lipozyme TL IM as Catalyst for the Synthesis of Eugenyl Acetate in Solvent-Free Acetylation,, Appl. Biochem. Biotechnol., vol. 176, no. 3, p.782–795, (2015).

DOI: 10.1007/s12010-015-1611-5