Abstract
Metal–organic framework MOF-5 was used for the first time as a heterogeneous acid catalyst for the simultaneous esterification/transesterification of two nonedible oils, waste cooking oil and Jatropha curcas oil. Fatty acid methyl ester (biodiesel) production was evaluated using an experimental central composite design. A surface response methodology allowed the determination of optimal reaction conditions in terms of methanol/oil molar ratio (3:1–45:1), reaction time (1–15 h), temperature (118–152 °C) and catalyst amount (0.1–0.9 wt%) with a variation lower than 10% with respect to the experimental yield value. The best oil to biodiesel yield conversions were 90.8% (36:1 M/O molar ratio, 12 h, 145 °C, and 0.75 wt% catalyst amount) for waste cooking oil and 88.3% (36:1 M/O molar ratio, 9.59 h, 145 °C, and 0.75 wt% catalyst amount) for Jatropha curcas oil together with respective 93.3% and 94.8% decreases in the free fatty acid content, respectively. It was also verified that the produced biodiesel meets the ASTM D6751 quality standard for some properties of the biofuel and the cost analysis of biodiesel production has also been provided.
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References
Aboubakar X, Goudoum A, Bébé Y, Mbofung CMF (2017) Optimization of Jatropha curcas pure vegetable oil production parameters for cooking energy. S Afr J ChemEng 24:196–212. https://doi.org/10.1016/j.sajce.2017.09.002
Adnan M, Li K, Wang J et al (2018) Hierarchical ZIF-8 toward immobilizing Burkholderia cepacia lipase for application in biodiesel preparation. Int J MolSci. https://doi.org/10.3390/ijms19051424
Al Hatrooshi AS, Eze VC, Harvey AP (2020) Production of biodiesel from waste shark liver oil for biofuel applications. Renew Energy 145:99–105. https://doi.org/10.1016/j.renene.2019.06.002
Biodiesel (2020) [Online]. Available at: https://www.alibaba.com/product-detail/Wholesale-price-UCO-used-cooking-oil_62547384275.html
Badday AS, Abdullah AZ, Lee KT (2013) Optimization of biodiesel production process from Jatropha oil using supported heteropolyacid catalyst and assisted by ultrasonic energy. Renew Energy 50:427–432. https://doi.org/10.1016/j.renene.2012.07.013
Brereton RG (2003) Chemometrics: data analysis for the laboratory and chemical plant. Wiley, Hoboken. https://doi.org/10.1002/0470863242
Canivet J, Fateeva A, Guo Y et al (2014) Water adsorption in MOFs: fundamentals and applications. ChemSoc Rev 43:5594–5617
Chen J, Liu R, Gao H et al (2014) Amine-functionalized metal–organic frameworks for the transesterification of triglycerides. J Mater Chem A 2:7205–7213. https://doi.org/10.1039/C4TA00253A
Chen X, Peng Y, Han X et al (2017) Sixteen isostructuralphosphonate metal-organic frameworks with controlled Lewis acidity and chemical stability for asymmetric catalysis. Nat Commun. https://doi.org/10.1038/s41467-017-02335-0
Chizallet C, Lazare S, Bazer-Bachi D et al (2010) Catalysis of transesterification by a nonfunctionalized metal–organic framework: acido-basicity at the external surface of ZIF-8 probed by FTIR and ab initio calculations. J Am ChemSoc 132:12365–12377. https://doi.org/10.1021/ja103365s
Cirujano FG, Corma A, Llabrés I Xamena FX (2015) Zirconium-containing metal organic frameworks as solid acid catalysts for the esterification of free fatty acids: synthesis of biodiesel and other compounds of interest. Catal Today 257:213–220. https://doi.org/10.1016/j.cattod.2014.08.015
Cordero-Ravelo V, Schallenberg-Rodriguez J (2018) Biodiesel production as a solution to waste cooking oil (WCO) disposal. Will any type of WCO do for a transesterification process? A quality assessment. J Environ Manag 228:117–129. https://doi.org/10.1016/j.jenvman.2018.08.106
Diesel prices (2020) [Online]. Available at: https://www.globalpetrolprices.com/diesel_prices/
DMF (2020) [Online]. Available at: https://spanish.alibaba.com/trade/search
Du DY, Qin JS, Sun Z et al (2013) An unprecedented (3,4,24)-connected heteropolyoxozincate organic framework as heterogeneous crystalline Lewis acid catalyst for biodiesel production. Sci Rep. https://doi.org/10.1038/srep02616
Endalew AK, Kiros Y, Zanzi R (2011) Heterogeneous catalysis for biodiesel production from Jatropha curcas oil (JCO). Energy 36:2693–2700. https://doi.org/10.1016/j.energy.2011.02.010
Gebremariam SN, Marchetti JM (2018) Economics of biodiesel production: review. Energy Convers Manag 168:74–84
Gelbard G, Brès O, Vargas RM et al (1995) 1H nuclear magnetic resonance determination of the yield of the transesterification of rapeseed oil with methanol. J Am Oil ChemSoc 72:1239–1241. https://doi.org/10.1007/BF02540998
Gohain M, Devi A, Deka D (2017) Musa balbisianaColla peel as highly effective renewable heterogeneous base catalyst for biodiesel production. Ind Crops Prod 109:8–18. https://doi.org/10.1016/j.indcrop.2017.08.006
Gui MM, Lee KT, Bhatia S (2008) Feasibility of edible oil vs. non-edible oil vs. waste edible oil as biodiesel feedstock. Energy 33:1646–1653
Hafizovic J, Bjørgen M, Olsbye U et al (2007) The inconsistency in adsorption properties and powder XRD data of MOF-5 is rationalized by framework interpenetration and the presence of organic and inorganic species in the nanocavities. J Am ChemSoc 129:3612–3620. https://doi.org/10.1021/ja0675447
Karmakar B, Halder G (2019) Progress and future of biodiesel synthesis: advancements in oil extraction and conversion technologies. Energy Convers Manag 182:307–339
Liu Y, Liu S, He D et al (2015) Crystal facets make a profound difference in polyoxometalate-containing metal–organic frameworks as catalysts for biodiesel production. J Am ChemSoc 137:12697–12703. https://doi.org/10.1021/jacs.5b08273
Lu L, Li XY, Liu XQ et al (2015) Enhancing the hydrostability and catalytic performance of metal–organic frameworks by hybridizing with attapulgite, a natural clay. J Mater Chem A 3:6998–7005. https://doi.org/10.1039/c5ta00959f
Ma Y, Gao Z, Wang Q, Liu Y (2018) Biodiesels from microbial oils: opportunity and challenges. BioresourTechnol 263:631–641
Methanol prices for North America (2020) [Online]. Available at: https://www.methanex.com/our-business/pricing
Mohammadshirazi A, Akram A, Rafiee S, BagheriKalhor E (2014) Energy and cost analyses of biodiesel production from waste cooking oil. Renew Sustain Energy Rev 33:44–49
Montgomery DC (2001) Design and analysis of experiments, 5th edn. Wiley, New York
Remya VR, Kurian M (2019) Synthesis and catalytic applications of metal–organic frameworks: a review on recent literature. IntNanoLett 9:17–29. https://doi.org/10.1007/s40089-018-0255-1
Nitrate (2020, November) [Online] Available at: https://spanish.alibaba.com/product-detail/98-zinc-nitrate-zinc-nitrate-hexahydrate-high-purity-cas-7779-88-6-62143063263.html
Organic acid (2020) [Online]. Available at: https://www.alibaba.com/product-detail/Terephthalic-acid-cas-100-21-0_1600133927336.html
Rincón LE, Jaramillo JJ, Cardona CA (2014) Comparison of feedstocks and technologies for biodiesel production: an environmental and techno-economic evaluation. Renew Energy 69:479–487. https://doi.org/10.1016/j.renene.2014.03.058
Rivera JM, Rincón S, Ben Youssef C, Zepeda A (2016) Highly efficient adsorption of aqueous Pb(II) with mesoporous metal-organic framework-5: an equilibrium and kinetic study. J Nanomater 2016:1–9. https://doi.org/10.1155/2016/8095737
Rodríguez NA, Parra R, Grela MA (2015) Structural characterization, optical properties and photocatalytic activity of MOF-5 and its hydrolysis products: implications on their excitation mechanism. RSC Adv 5:73112–73118. https://doi.org/10.1039/c5ra11182j
Salimi Z, Hosseini SA (2019) Study and optimization of conditions of biodiesel production from edible oils using ZnO/BiFeO3 nano magnetic catalyst. Fuel 239:1204–1212. https://doi.org/10.1016/j.fuel.2018.11.125
Sánchez-Vázquez R, Pirez C, Iglesias J et al (2013) Zr-containing hybrid organic-inorganic mesoporous materials: hydrophobic acid catalysts for biodiesel production. ChemCatChem 5:994–1001. https://doi.org/10.1002/cctc.201200527
Shah KA, Parikh JK, Maheria KC (2014) Optimization studies and chemical kinetics of silica sulfuric acid-catalyzed biodiesel synthesis from waste cooking oil. Bioenergy Res 7:206–216. https://doi.org/10.1007/s12155-013-9363-y
Sharma YC, Singh B (2009) Development of biodiesel: current scenario. Renew Sustain Energy Rev 13:1646–1651
Tan K, Nijem N, Canepa P et al (2012) Stability and hydrolyzation of metal organic frameworks with paddle-wheel SBUs upon hydration. Chem Mater 24:3153–3167. https://doi.org/10.1021/cm301427w
Thitsartarn W, Maneerung T, Kawi S (2015) Highly active and durable Ca-doped Ce-SBA-15 catalyst for biodiesel production. Energy 89:946–956. https://doi.org/10.1016/j.energy.2015.06.039
Tiwari A, Rajesh VM, Yadav S (2018) Biodiesel production in micro-reactors: a review. Energy Sustain Dev 43:143–161
Torres-Rodríguez DA, Romero-Ibarra IC, Ibarra IA, Pfeiffer H (2016) Biodiesel production from soybean and Jatropha oils using cesium impregnated sodium zirconate as a heterogeneous base catalyst. Renew Energy 93:323–331. https://doi.org/10.1016/j.renene.2016.02.061
U.S. Energy Information Administration (2020) Gasoline and diesel fuel update. Washington D.C. September [Online]. Available at: https://www.eia.gov/petroleum/gasdiesel/
Volkringer C, Cohen SM (2010) Generating reactive MILs: Isocyanate-and isothiocyanate-bearing MILs through postsynthetic modification. AngewChemInt Ed 49:4644–4648. https://doi.org/10.1002/anie.201001527
Vyas AP, Verma JL, Subrahmanyam N (2010) A review on FAME production processes. Fuel 89:1–9
Wan H, Chen C, Wu Z et al (2015) Encapsulation of heteropolyanion-based ionic liquid within the metal–organic framework MIL-100(Fe) for biodiesel production. ChemCatChem 7:441–449. https://doi.org/10.1002/cctc.201402800
Wang LP, Xiao B, Wang GY, Wu J (2011a) Synthesis of polycarbonate diolcatalyzed by metal-organic framework Zn4O[CO2–C6H4–CO2]3. Sci China Chem 54:1468–1473. https://doi.org/10.1007/s11426-011-4284-0
Wang R, Hanna MA, Zhou WW et al (2011b) Production and selected fuel properties of biodiesel from promising non-edible oils: Euphorbia lathyris L., Sapium sebiferum L. and Jatropha curcas L. BioresourTechnol 102:1194–1199. https://doi.org/10.1016/j.biortech.2010.09.066
Wang W, Lu P, Tang H, Ma Y, Yang X (2017) A Zanthoxylum bungeanum seed oil-based carbon solid acid catalyst for the production of biodiesel. New J Chem 41:9256–9261. https://doi.org/10.1039/C7NJ01271C
Xie W, Wan F (2019a) Biodiesel production from acidic oils using polyoxometalate-based sulfonated ionic liquids functionalized metal-organic frameworks. CatalLett 149:2916–2929. https://doi.org/10.1007/s10562-019-02800-z
Xie W, Wan F (2019b) Immobilization of polyoxometalate-based sulfonated ionic liquids on UiO-66-2COOH metal-organic frameworks for biodiesel production via one-pot transesterification-esterification of acidic vegetable oils. ChemEng J 365:40–50. https://doi.org/10.1016/j.cej.2019.02.016
Ye C, Qi Z, Cai D, Qiu T (2019) Design and synthesis of ionic liquid supported hierarchically porous Zr metal-organic framework as a novel Brønsted–Lewis acidic catalyst in biodiesel synthesis. IndEngChem Res 58:1123–1132. https://doi.org/10.1021/acs.iecr.8b04107
Zhang Q, Liu X, Yang T et al (2019) Facile synthesis of polyoxometalates tethered to post Fe-BTC frameworks for esterification of free fatty acids to biodiesel. RSC Adv 9:8113–8120. https://doi.org/10.1039/c8ra10574j
Zhou F, Lu N, Fan B et al (2016) Zirconium-containing UiO-66 as an efficient and reusable catalyst for transesterification of triglyceride with methanol. J Energy Chem 25:874–879. https://doi.org/10.1016/j.jechem.2016.06.003
Zhou Y, Song J, Liang S et al (2009) Metal-organic frameworks as an acid catalyst for the synthesis of ethyl methyl carbonate via transesterification. J MolCatal A Chem 308:68–72. https://doi.org/10.1016/j.molcata.2009.03.027
Živković SB, Veljković MV, Banković-Ilić IB et al (2017) Technological, technical, economic, environmental, social, human health risk, toxicological and policy considerations of biodiesel production and use. Renew Sustain Energy Rev 79:222–247
Acknowledgments
This work was supported by CONACYT (215242 and INFR-2016-01-270022). The authors wish to thank the National Laboratory of Nano and Biomaterials (CONACYT) of the CINVESTAV-Mérida for conducting the RMN, FTIR and XRD analysis, in particular Ph.D. degree holder Patricia Quintana, M.S. degree holder Dora Huerta Quintanilla, M.S. degree holder Daniel Aguilar Treviño and Biologist Ana Cristóbal Ramos.
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Ben-Youssef, C., Chávez-Yam, A., Zepeda, A. et al. Simultaneous esterification/transesterification of waste cooking oil and Jatropha curcas oil with MOF-5 as a heterogeneous acid catalyst. Int. J. Environ. Sci. Technol. 18, 3313–3326 (2021). https://doi.org/10.1007/s13762-020-03088-y
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DOI: https://doi.org/10.1007/s13762-020-03088-y