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The Use of Silica Extracted from Kaolin as Catalyst Support for Esterification of 4-Hydroxybenzoic Acid with Sucrose

Department of Chemistry, Faculty of Mathematic and Natural Sciences, Universitas Indonesia, Indonesia

Received: 13 Jan 2020; Revised: 14 May 2020; Accepted: 21 May 2020; Available online: 24 Jun 2020; Published: 30 Jun 2020.
Open Access Copyright 2020 Jurnal Kimia Sains dan Aplikasi under http://creativecommons.org/licenses/by-sa/4.0.

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Abstract
SiO2 was extracted from kaolin using concentrated HCl and HNO3 mixture and used as solid support for both Bronsted (HClO4 and H2SO4) and Lewis Acid (AlCl3 and ZnCl2). Before extraction, kaolin was calcined at 800°C for eight hours to form metastable kaolin. After the extraction procedure, silica was recovered in 51.6% yield. Silica and the resulting solid acids were then characterized using XRD, XRF, and FTIR. XRD pattern shows that silica synthesized from kaolin is in the mixture of amorphous and α-quartz silica. Immobilization of acids alters its structure becomes more crystalline. XRF analysis shows that the loading of AlCl3 and ZnCl2 was 9.5 and 24.8%, respectively. The acid catalysts were then used in the esterification reaction of 4-hydroxybenzoic acid with sucrose. The reactions were conducted in dimethyl sulfoxide (DMSO) solvent by varying reaction time and reaction temperature. The highest conversion of starting materials and selectivity towards ester was obtained over the AlCl3/SiO2 catalyst. DPPH radical scavenging test shows that the ester exhibits good antioxidant activity.
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Keywords: silica; kaolin; solid support; acid catalyst; esterification
Funding: Universitas Indonesia

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  1. Fuangfa Unob, Benjawan Wongsiri, Nuchnicha Phaeon, Mahitti Puanngam and Juwadee Shiowatana, Reuse of waste silica as adsorbent for metal removal by iron oxide modification, Journal of Hazardous Materials, 142, 1, (2007), 455-462 https://doi.org/10.1016/j.jhazmat.2006.08.049
  2. Benjamin Curdts, Christian Pflitsch, Christoph Pasel, Martin Helmich, Dieter Bathen and Burak Atakan, Novel silica-based adsorbents with activated carbon structure, Microporous and Mesoporous Materials, 210, (2015), 202-205 https://doi.org/10.1016/j.micromeso.2015.02.007
  3. Choiril Azmiyawati, Kajian Kinetika Adsorpsi Mg(II) pada Silika Gel Termodifikasi Gugus Sulfonat, Jurnal Kimia Sains dan Aplikasi, 9, 2, (2006), 35-39 https://doi.org/10.14710/jksa.9.2.35-39
  4. Yasuhiro Kamitori, Masaru Hojo, Ryoichi Masuda, Tatsuo Izumi and Shuichi Tsukamoto, Silica gel as an effective catalyst for the alkylation of phenols and some heterocyclic aromatic compounds, The Journal of Organic Chemistry, 49, 22, (1984), 4161-4165 https://doi.org/10.1021/jo00196a012
  5. Kidon Nam, Seongyop Lim, Sang-Kyung Kim, Seong-Ho Yoon and Doo-Hwan Jung, Application of silica as a catalyst support at high concentrations of methanol for direct methanol fuel cells, International Journal of Hydrogen Energy, 37, 5, (2012), 4619-4626 https://doi.org/10.1016/j.ijhydene.2011.05.068
  6. Rafael Huirache-Acuña, Rufino Nava, Carmen L. Peza-Ledesma, Javier Lara-Romero, Gabriel Alonso-Núez, Barbara Pawelec and Eric M. Rivera-Muñoz, SBA-15 Mesoporous Silica as Catalytic Support for Hydrodesulfurization Catalysts—Review, Materials, 6, 9, (2013), 4139-4167 https://doi.org/10.3390/ma6094139
  7. Arne Thomas, Frederic Goettmann and Markus Antonietti, Hard Templates for Soft Materials: Creating Nanostructured Organic Materials, Chemistry of Materials, 20, 3, (2008), 738-755 https://doi.org/10.1021/cm702126j
  8. HaYeon Lee and Cafer T. Yavuz, Increasing mesoporosity by a silica hard template in a covalent organic polymer for enhanced amine loading and CO2 capture capacity, Microporous and Mesoporous Materials, 229, (2016), 44-50 https://doi.org/10.1016/j.micromeso.2016.04.019
  9. Ahmad Bitar, Nasir M. Ahmad, Hatem Fessi and Abdelhamid Elaissari, Silica-based nanoparticles for biomedical applications, Drug Discovery Today, 17, 19, (2012), 1147-1154 https://doi.org/10.1016/j.drudis.2012.06.014
  10. Naiara I. Vazquez, Zoilo Gonzalez, Begoña Ferrari and Yolanda Castro, Synthesis of mesoporous silica nanoparticles by sol–gel as nanocontainer for future drug delivery applications, Boletín de la Sociedad Española de Cerámica y Vidrio, 56, 3, (2017), 139-145 https://doi.org/10.1016/j.bsecv.2017.03.002
  11. Ridla Bakri, Tresye Utari and Indra Puspita Sari, Kaolin sebagai sumber SiO2 untuk pembuatan katalis Ni/SiO2: karakterisasi dan uji katalis pada hidrogenasi benzena menjadi sikloheksana, Makara Journal of Science, 12, 1, (2010), 37-43 https://doi.org/10.7454/mss.v12i1.304
  12. Usama Zulfiqar, Tayyab Subhani and S. Wilayat Husain, Synthesis and characterization of silica nanoparticles from clay, Journal of Asian Ceramic Societies, 4, 1, (2016), 91-96 https://doi.org/10.1016/j.jascer.2015.12.001
  13. Franz X. Gingele, Patrick De Deckker and Claus-Dieter Hillenbrand, Clay mineral distribution in surface sediments between Indonesia and NW Australia — source and transport by ocean currents, Marine Geology, 179, 3, (2001), 135-146 https://doi.org/10.1016/S0025-3227(01)00194-3
  14. Asit K. Chakraborti, Bavneet Singh, Sunay V. Chankeshwara and Alpesh R. Patel, Protic Acid Immobilized on Solid Support as an Extremely Efficient Recyclable Catalyst System for a Direct and Atom Economical Esterification of Carboxylic Acids with Alcohols, The Journal of Organic Chemistry, 74, 16, (2009), 5967-5974 https://doi.org/10.1021/jo900614s
  15. Wilmar Osorio-Viana, Miguel Duque-Bernal, Javier Fontalvo, Izabela Dobrosz-Gómez and Miguel Ángel Gómez-García, Kinetic study on the catalytic esterification of acetic acid with isoamyl alcohol over Amberlite IR-120, Chemical Engineering Science, 101, (2013), 755-763 https://doi.org/10.1016/j.ces.2013.07.009
  16. Pepijn Prinsen, Rafael Luque and Camino González-Arellano, Zeolite catalyzed palmitic acid esterification, Microporous and Mesoporous Materials, 262, (2018), 133-139 https://doi.org/10.1016/j.micromeso.2017.11.029
  17. Leandro Zatta, Luiz Pereira Ramos and Fernando Wypych, Acid-activated montmorillonites as heterogeneous catalysts for the esterification of lauric acid acid with methanol, Applied Clay Science, 80-81, (2013), 236-244 https://doi.org/10.1016/j.clay.2013.04.009
  18. Enas A. Almadani, Farah W. Harun, Salina M. Radzi and Syamsul K. Muhamad, Cu2+ Montmorillonite K10 Clay Catalyst as a Green Catalyst for Production of Stearic Acid Methyl Ester: Optimization Using Response Surface Methodology (RSM), Bulletin of Chemical Reaction Engineering, 13, 1, (2018), 187-195 https://doi.org/10.9767/bcrec.13.1.1397.187-195
  19. Mehejabeen Kotwal, Anuj Kumar and Srinivas Darbha, Three-dimensional, mesoporous titanosilicates as catalysts for producing biodiesel and biolubricants, Journal of Molecular Catalysis A: Chemical, 377, (2013), 65-73 https://doi.org/10.1016/j.molcata.2013.04.029
  20. Roberta Gomes Prado, Maria Lucia Bianchi, Estella Gaspar da Mota, Sarah Silva Brum, João Henrique Lopes and Márcio José da Silva, H3PMo12O40/Agroindustry Waste Activated Carbon-Catalyzed Esterification of Lauric Acid with Methanol: A Renewable Catalytic Support, Waste and Biomass Valorization, 9, 4, (2018), 669-679 https://doi.org/10.1007/s12649-017-0012-0
  21. Emma M. Björk, María P. Militello, Luciano H. Tamborini, Rusbel Coneo Rodriguez, Gabriel A. Planes, Diego F. Acevedo, M. Sergio Moreno, Magnus Odén and Cesar A. Barbero, Mesoporous silica and carbon based catalysts for esterification and biodiesel fabrication—The effect of matrix surface composition and porosity, Applied Catalysis A: General, 533, (2017), 49-58 https://doi.org/10.1016/j.apcata.2017.01.007
  22. Reza Farhoosh, Saeed Johnny, Maryam Asnaashari, Najme Molaahmadibahraseman and Ali Sharif, Structure–antioxidant activity relationships of o-hydroxyl, o-methoxy, and alkyl ester derivatives of p-hydroxybenzoic acid, Food Chemistry, 194, (2016), 128-134 https://doi.org/10.1016/j.foodchem.2015.08.003
  23. Sun-Yup Shim, Ye E. Lee, Hwa Y. Song and Mina Lee, p-Hydroxybenzoic Acid β-d-Glucosyl Ester and Cimidahurinine with Antimelanogenesis and Antioxidant Effects from Pyracantha angustifolia via Bioactivity-Guided Fractionation, Antioxidants, 9, 3, (2020), https://doi.org/10.3390/antiox9030258
  24. Coral Barbas, Javier Rupérez, Andre Dams and Ronald E. Majors, Separation of paraben preservatives by reversed-phase HPLC application in foods, beverages, cosmetics, in, Agilent Technologies, Amstelveen, The Netherlands, 2005, pp. 1-4
  25. Philip Molyneux, The use of the stable free radical diphenylpicrylhydrazyl (DPPH) for estimating antioxidant activity, Songklanakarin Journal of Science and Technology (SJST), 26, 2, (2004), 211-219
  26. Pratiwi, Dewi Puspa and Mindarti Harapini, Peroxide value and DPPH (diphenyl picril hydrazil hydrate) free radical scavenger activity of Knema laurina methanol extract, Indonesian Journal of Pharmacy, 17, 1, (2006), 32-36 http://dx.doi.org/10.14499/indonesianjpharm0iss0pp32-36
  27. M. H. Gaber, N. A. Abd el Halim and W. A. Khalil, Antioxidant activity of ascorbic acid against peroxidation of phosphatidylcholine liposomes exposed to gamma radiation: a synergistic interaction?, Romanian Journal of Biophysics, 12, 3-4, (2002), 103-115
  28. Horacio E. Bergna, Colloid Chemistry of Silica, in: The Colloid Chemistry of Silica, American Chemical Society, 1994, pp. 1-47 https://doi.org/10.1021/ba-1994-0234.ch001
  29. Helmut Günzler, Hans Ulrich Gremlich and Herbert Heise, IR Spectroscopy: An Introduction, John Wiley & Sons, Limited, 2002
  30. Fu Yang and Jingjing Tang, Catalytic Upgrading of Renewable Levulinic Acid to Levulinate Esters Using Perchloric Acid Decorated Nanoporous Silica Gels, ChemistrySelect, 4, 4, (2019), 1403-1409 https://doi.org/10.1002/slct.201803608

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