Catalytic performance of cerium-modified ZSM-5 zeolite as a catalyst for the esterification of glycerol with acetic acid
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Priyanka Gautam
and
Amjad Ali
Abstract
Esterification of glycerol with acetic acid was carried out over cerium-modified ZSM-5 zeolites to synthesize monoacetin (MA) and diacetin (DA). The modified zeolite catalyst was characterized. The effect of reaction process parameters such as acetic acid to glycerol mole ratio (1–11), reaction temperature (30–120 °C), and catalyst weight (2–8 wt %) on the selectivity of the product was investigated. At 120 °C reaction temperature, 8 wt % catalyst, and 9:1 acetic acid to glycerol mole ratio, about 98.32% conversion of glycerol were obtained. This reaction follows pseudo-first-order reaction kinetics and the activation energy was found to be 63.72 kJ mol−1.
Funding source: Thapar Institute of Engineering and Technology, Patiala, India
Acknowledgment
The author would like to thank the Thapar Institute of Engineering and Technology, Patiala, India for financial support.
Author contribution: All the authors have accepted responsibility for the entire content of this submitted manuscript and approved submission.
Research funding: None declared.
Conflict of interest statement: The authors declare no conflicts of interest regarding this article.
References
Barman, B., N. C. Pradhan, and J. K. Basu. 2005. “Kinetics of Alkylation of Benzene with Isopropyl Alcohol over Ce-Exchanged NaX Zeolite.” Industrial & Engineering Chemistry Research 44: 7313–9, https://doi.org/10.1021/ie050366q.Search in Google Scholar
Cheng, Y., J. S. Li, L. J. Wang, X. Y. Sun, and X. D. Liu. 2006. “Synthesis and Characterization of Ce-ZSM-5 Zeolite Membranes.” Separation and Purification Technology 51: 210–8, https://doi.org/10.1016/j.seppur.2006.02.002.Search in Google Scholar
Cahyono, R. B., Z. Mufrodi, A. Hidayat, and A. Budiman. 2016. “Acetylation of Glycerol for Triacetin Production Using Zr-Natural Zeolite Catalyst.” ARPN Journal of Engineering and Applied Sciences 11 (8): 5194–7. ISSN 1819-6608.Search in Google Scholar
Costa, B. O. D., H. P. Decolatti, M. S. Legnoverde, and C. A. Querini. 2017. “Influence of Acidic Properties of Different Solid Acid Catalysts for Glycerol Acetylation.” Catalysis Today 289: 222–30, https://doi.org/10.1016/j.cattod.2016.09.015.Search in Google Scholar
Fattahi, N., K. Triantafyllidis, R. Luque, and A. Ramazani. 2019. “Zeolite-based Catalysts: A Valuable Approach toward Ester Bond Formation.” Catalysts 9 (9): 758, https://doi.org/10.3390/catal9090758.Search in Google Scholar
Gonçalves, V. L. C., B. P. Pinto, J. C. Silva, and C. J. A. Mota. 2008. “Acetylation of Glycerol Catalyzed by Different Solid Acids.” Catalysis Today 133–135: 673–7, https://doi.org/10.1016/j.cattod.2007.12.037.Search in Google Scholar
Hu, W., Y. Zhang, Y. Huang, J. Wang, J. Gao, and J. Xu. 2015. “Selective Esterification of Glycerol with Acetic Acid to Diacetin Using Antimony Peroxide as a Reusable Catalyst.” Journal of Energy Chemistry 24 (5): 632–6, https://doi.org/10.1016/j.jechem.2015.08.001.Search in Google Scholar
Huang, M. Y., X. X. Han, C. Te Hung, J. C. Lin, P. H. Wu, J. C. Wu, and S. Bin Liu. 2014. “Heteropolyacid-based Ionic Liquids as Efficient Homogeneous Catalysts for Acetylation of Glycerol.” Journal of Catalysis 320: 42–51, https://doi.org/10.1016/j.jcat.2014.09.022.Search in Google Scholar
Jagadeeswaraiah, K., M. Balaraju, P. S. S. Prasad, and N. Lingaiah. 2010. “Selective Esterification of Glycerol to Bioadditives over Heteropoly Tungstate Supported on Cs-Containing Zirconia Catalysts.” Applied Catalysis A: General 386: 166–70, https://doi.org/10.1016/j.apcata.2010.07.046.Search in Google Scholar
Kale, S., U. Armbruster, S. Umbarkar, M. Dongare, and A. Martin. 2013. “Esterification of Glycerol with Acetic Acid for Improved Production of Triacetin Using Toluene as an Entrainer.” In 10th Green Chemistry Conference, 70–1.Search in Google Scholar
Kale, S., S. B. Umbarkar, M. K. Dongare, R. Eckelt, U. Armbruster, and A. Martin. 2015. “Selective Formation of Triacetin by Glycerol Acetylation Using Acidic Ion-Exchange Resins as Catalyst and Toluene as an Entrainer.” Applied Catalysis A: General 490: 10–6, https://doi.org/10.1016/j.apcata.2014.10.059.Search in Google Scholar
Karnjanakom, S., P. Maneechakr, C. Samart, and G. Guan. 2018. “Ultrasound-assisted Acetylation of Glycerol for Triacetin Production over Green Catalyst: A Liquid Biofuel Candidate.” Energy Conversion and Management 173: 262–70, https://doi.org/10.1016/j.enconman.2018.07.086.Search in Google Scholar
Liu, J., Z. Wang, Y. Sun, R. Jian, P. Jian, and D. Wang. 2019. “Selective Synthesis of Triacetin from Glycerol Catalyzed by HZSM-5/MCM-41 Micro/mesoporous Molecular Sieve.” Chinese Journal of Chemical Engineering 27: 1073–8, https://doi.org/10.1016/j.cjche.2018.09.013.Search in Google Scholar
Mallesham, B., P. Sudarsanam, and B. M. Reddy. 2014. “Production of Biofuel Additives from Esterification and Acetalization of Bioglycerol over SnO2-Based Solid Acids.” Industrial & Engineering Chemistry Research 53: 18775–85, https://doi.org/10.1021/ie501133c.Search in Google Scholar
Momayez, F., J. T. Darian, and S. M. T. Sendesi. 2015. “Synthesis of Zirconium and Cerium over HZSM-5 Catalysts for Light Olefins Production from Naphtha.” Journal of Analytical and Applied Pyrolysis 112: 135–40, https://doi.org/10.1016/j.jaap.2015.02.006.Search in Google Scholar
Neto, A. B. S., A. C. Oliveira, E. Rodriguez-Castellon, A. F. Campos, P. T. C. Freire, F. F. F. Sousa, J. M. Filho, J. C. S. Araujo, and R. Lang. 2018. “A Comparative Study on Porous Solid Acid Oxides as Catalysts in the Esterification of Glycerol with Acetic Acid.” Catalysis Today 349: 57–67https://doi.org/10.1016/j.cattod.2018.05.057.Search in Google Scholar
Pagliaro, M., R. Ciriminna, H. Kimura, M. Rossi, and C. D. Pina. 2007. “From Glycerol to Value-Added Products.” Angewandte Chemie International Edition 46 (24): 4434–40, https://doi.org/10.1002/anie.200604694.Search in Google Scholar PubMed
Popova, M., A. Szegedi, A. Ristic, and N. N. Tusar. 2014. “Glycerol Acetylation on Mesoporous KIL-2 Supported Sulphated Zirconia Catalysts.” Catalysis Science & Technology 4: 3993–4000, https://doi.org/10.1039/c4cy00548a.Search in Google Scholar
Pradhan, N. C., S Barman, and S. K. Maity. 2005. “Alkylation of Toluene with Isopropyl Alcohol Catalyzed by Ce Exchanged 13X Zeolite Catalyst.” Chemical Engineering Journal 114: 39–45, https://doi.org/10.1016/j.cej.2005.08.014.Search in Google Scholar
Rane, S. A., S. M. Pudi, and P. Biswas. 2016. “Esterification of Glycerol with Acetic Acid over Highly Active and Stable Alumina-Based Catalysts: A Reaction Kinetics Study.” Chemical and Biochemical Engineering Quarterly 30 (1): 33–45, https://doi.org/10.15255/CABEQ.2014.2093.Search in Google Scholar
Rastegari, H., H. S. Ghaziaskar, and M. Yalpani. 2015. “Valorization of Biodiesel Derived Glycerol to Acetins by Continuous Esterification in Acetic Acid: Focusing on High Selectivity to Diacetin and Triacetin with No Byproducts.” Industrial & Engineering Chemistry Research 54: 3279–84, https://doi.org/10.1021/acs.iecr.5b00234.Search in Google Scholar
Rathi, A., S. Basu, and S. Barman. 2019. “Adsorptive Removal of Fipronil from its Aqueous Solution by Modified Zeolite HZSM-5: Equilibrium, Kinetic and Thermodynamic Study.” Journal of Molecular Liquids 283: 867–78, https://doi.org/10.1016/j.molliq.2019.02.140.Search in Google Scholar
Reddy, P. S., P. Sudarsanam, G. Raju, and B. M. Reddy. 2010. “Synthesis of Bio-Additives: Acetylation of Glycerol over Zirconia-Based Solid Acid Catalysts.” Catalysis Communication 11: 1224–8, https://doi.org/10.1016/j.catcom.2010.07.006.Search in Google Scholar
Saharan, R., G. Halder, and S. Barman. 2019. “Synthesis of Ethyl Phenol over Modified HZSM-5 Catalyst in a Fixed Bed Reactor.” International Journal of Chemical Reactor Engineering 17: 1–12, https://doi.org/10.1515/ijcre-2018-0224.Search in Google Scholar
Sandesh, S., P. Manjunathan, A. B. Halgeri, and G. V. Shanbhag. 2015. “Glycerol Acetins: Fuel Additive Synthesis by Acetylation and Esterification of Glycerol Using Cesium Phosphotungstate Catalyst.” RSC Advances 5: 104354–62, https://doi.org/10.1039/c5ra17623a.Search in Google Scholar
Setyaningsih, L., F. Siddiq, and A. Pramezy. 2018. “Esterification of Glycerol with Acetic Acid over Lewatit Catalyst.” MATEC Web of Conferences 154: 2–5, https://doi.org/10.1051/matecconf/201815401028.Search in Google Scholar
Wepoh, H. 2015. “Synthesis of Triacetin from Glycerol.” 3–10.Search in Google Scholar
Yilmaz, B., and U. Muller. 2009. “Catalytic Applications of Zeolites in Chemical Industry.” Topics in Catalysis 52: 888–95, https://doi.org/10.1007/s11244-009-9226-0.Search in Google Scholar
Zhang, M., J. Shi, Y. Sun, W. Ning, and Z. Hou. 2015. “Selective Oxidation of Glycerol over Nitrogen-Doped Carbon Nanotubes Supported Platinum Catalysts in Base-free Solution.” Catalysis Communication 70: 72–6, https://doi.org/10.1016/j.catcom.2015.08.002.Search in Google Scholar
Zhou, L., E. Al-Zaini, and A. A. Adesina. 2013. “Catalytic Characteristics and Parameters Optimization of the Glycerol Acetylation over Solid Acid Catalysts.” Fuel 103: 617–25, https://doi.org/10.1016/j.fuel.2012.05.042.Search in Google Scholar
Zhou, L., T. H. Nguyen, and A. A. Adesina. 2012. “The Acetylation of Glycerol Over Amberlyst-15: Kinetic and Product Distribution.” Fuel Processing Technology 104: 310–8, https://doi.org/10.1016/j.fuproc.2012.06.001.Search in Google Scholar
Supplementary Material
The online version of this article offers supplementary material (https://doi.org/10.1515/ijcre-2020-0081).
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Articles in the same Issue
- Review
- Separation and purification of fatty acids by membrane technology: a critical review
- Articles
- Investigation of the flow patterns and power requirements in agitated systems: effects of the design of baffles and vessel base
- Computational fluid dynamics simulation of solid-liquid suspension characteristics in a stirred tank with punched circle package impellers
- Fischer-Tropsch reaction mixture permeation through a silicalite-1 membrane reactor and its effect on the produced hydrocarbons distribution
- Influence of the amine alkyl-chain upon carbon dioxide absorption in G-L-L reactor
- Catalytic performance of cerium-modified ZSM-5 zeolite as a catalyst for the esterification of glycerol with acetic acid
- Numerical study on the effect of planar normal and Halbach magnet arrays on micromixing
- The optimization and statistical analysis of fermentative hydrogen production using Taguchi method
- Mechanism of recovery processes for rare earth and iron from Bayan Obo tailings
- Short Communication
- Design optimization of micromixer with circular mixing chambers (M-CMC) using Taguchi-based grey relational analysis
