Abstract
High biodiesel yield was obtained by using poly (acidic ionic liquid)s. The ionic liquid monomer was synthesized through quaternary ammonization on the N,N-Dimethyl-3-aminophenol with 1,3-propanesultone and p-Hydroxybenzenesulfonic acid. The IL monomer and formaldehyde was used to synthesize the poly(acidic ionic liquid)s. Several physicochemical techniques were used in the characterization of this poly(acidic ionic liquid)s. The esterification of oleic acid and methanol was used to investigate the catalytic activity of the synthesized catalyst. In order to obtain the maximum yield, four parameters (reaction time, amount of methanol, temperature and catalyst amount) were considered. In the optimum condition (5 wt% catalyst amount, 9:1 methanol/oleic acid ratio at 80 °C for 1.5 h), the ester yield was up to 93.3%. After four cycles of use, the catalytic activity of FCPIL did not exhibit significant decline.
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Wang F, Jiang J, Wang K, Zhai Q, Long F, Liu P, Feng J, Xia H, Ye J, Li J, Xu J (2019) Hydrotreatment of lipid model for diesel-like alkane using nitrogen-doped mesoporous carbon-supported molybdenum carbide. Appl Catal B Environ 242:150–160
Coumans AE, Hensen EJM (2017) A model compound (methyl oleate, oleic acid, triolein) study of triglycerides hydrodeoxygenation over alumina-supported NiMo sulfide. Appl Catal B Environ 201:290–301
Wang Y, Zhao D, Chen G, Liu S, Ji N, Ding H, Fu J (2019) Preparation of phosphotungstic acid based poly(ionic liquid) and its application to esterification of palmitic acid. Renew Energ 133:317–324
Fangrui MA, Hanna AHB (1999) Biodiesel production: a review. Bioresour Technol 70:1–15
Silva Â, Wilson K, Lee AF, Santos VCD, Bacilla ACC, Mantovani KM, Nakagaki S (2017) Nb2O5/SBA-15 catalyzed propanoic acid esterification. Appl Catal B Environ 205:498–504
Hoydonckx HE, De Vos DE, Chavan SA, Jacobs PA (2004) Esterification and transesterification of renewable chemical. Top Catal 27:83–96
Helwani Z, Othman MR, Aziz N, Fernando WJN, Kim J (2009) Technologies for production of biodiesel focusing on green catalytic techniques: a review. Fuel Process Technol 90:1502–1514
Zhao D, Liu M, Zhang J, Li J, Ren P (2013) Synthesis, characterization, and properties of imidazole dicationic ionic liquids and their application in esterification. Chem Eng J 221:99–104
Niu S, Ning Y, Lu C, Han K, Yu H, Zhou Y (2018) Esterification of oleic acid to produce biodiesel catalyzed by sulfonated activated carbon from bamboo. Energ Convers Manage 163:59–65
Chen S (2014) Production of Jatropha biodiesel fuel over sulfonic acid-based solid acids. Bioresource Technol 157:346–350
Liu H, Chen J, Chen L, Xu Y, Guo X, Fang D (2016) Carbon Nanotube-Based Solid Sulfonic Acids as Catalysts for Production of Fatty Acid Methyl Ester via Transesterification and Esterification ACS Sustain. Chem Eng 4:3140–3150
Sun K, Lu J, Ma L, Han Y, Fu Z, Ding J (2015) A comparative study on the catalytic performance of different types of zeolites for biodiesel production. Fuel 158:848–854
Tropecêlo AI, Casimiro MH, Fonseca IM, Ramos AM, Vital J, Castanheiro JE (2010) Esterification of free fatty acids to biodiesel over heteropolyacids immobilized on mesoporous silica. Appl Catal A Gen 390:183–189
Zhang Z, Fan F, Xing H, Yang Q, Bao Z, Ren Q (2017) Efficient Synthesis of Cyclic Carbonates from Atmospheric CO2 Using a Positive Charge Delocalized Ionic Liquid Catalyst. ACS Sustain Chem Eng 5:2841–2846
Bielas R, Mielańczyk A, Siewniak A, Neugebauer D (2016) Trimethylammonium-Based Polymethacrylate Ionic Liquids with Tunable Hydrophilicity and Charge Distribution as Carriers of Salicylate Anions. ACS Sustain Chem Eng 4:4181–4191
Livi S, Chardin C, Lins LC, Halawani N, Pruvost S, Duchet-Rumeau J, Gérard J, Baudoux J (2019) From Ionic Liquid Epoxy Monomer to Tunable Epoxy-Amine Network: Reaction Mechanism and Final Properties. ACS Sustain Chem Eng 7:3602–3613
Wang X, Li J, Chen G, Guo Z, Zhou Y, Wang J (2015) Hydrophobic Mesoporous Poly(ionic liquid)s towards Highly Efficient and Contamination-Resistant Solid-Base Catalysts. ChemCatChem 7:993–1003
Feng Y, Li L, Wang X, Yang J, Qiu T (2017) Stable poly (ionic liquid) with unique crosslinked microsphere structure as efficient catalyst for transesterification of soapberry oil to biodiesel. Energ Convers Manage 153:649–658
Chen S, Chang A, Lin X, Zhai Z, Lu F, Zhou S, Guo H, Wu W (2018) Synthesis and characterization of ureidoderivatized UCST-type poly(ionic liquid) microgels†. Polym Chem-UK 9:1439–1447
Khiratkar AG, Balinge KR, Krishnamurthy M, Cheralathan KK, Patle DS, Singh V, Arora S, Bhagat PR (2018) Sulphonic Acid-Functionalized Benzimidazolium Based Poly Ionic Liquid Catalyzed Esterification of Levulinic Acid. Catal Lett 148:680–690
Zhang J, Zhang S, Han J, Hu Y, Yan R (2015) Uniform acid poly ionic liquid-based large particle and its catalytic application in esterification reaction. Chem Eng J 271:269–275
Lin X, Ling X, Chen J, Li M, Xu T, Qiu T (2019) Self-solidification ionic liquids as heterogeneous catalysts for biodiesel production. Green Chem 21:3182–3189
Vieira Grossi C, de Oliveira JE, de Araújo MH, Lago RM, da Silva MJ (2010) Sulfonated polystyrene: a catalyst with acid and superabsorbent properties for the esterification of fatty acids. Fuel 89:257–259
Holopainen T, Alvila L, Rainio J, Pakkanen TT (1998) IR spectroscopy as a quantitative and predictive analysis method of phenol–formaldehyde resol resins. J Appl Polym Sci 69:2175–2185
Qiao W, Li S, Guo G, Han S, Ren S, Ma Y (2015) Synthesis and characterization of phenolformaldehyde resin using enzymatic hydrolysis lignin. J Ind Eng Chem 21:1417–1422
Konwar LJ, Samikannu A, Mäki-Arvela P, Boström D, Mikkola JP (2018) Lignosulfonate-based macro/mesoporous solid protonic acids for acetalization of glycerol to bio-additives. Appl Catal B Environ 220:314–323
Pan H, Li H, Zhang H, Wang A, Yang S (2019) Acidic ionic liquid-functionalized mesoporous melamine-formaldehyde polymer as heterogeneous catalyst for biodiesel production. Fuel 239:886–895
Liu H, Chen J, Chen L, Xu Y, Guo X, Fang D (2016) Carbon Nanotube-Based Solid Sulfonic Acids as Catalysts for Production of Fatty Acid Methyl Ester via Transesterification and Esterification. ACS Sustain Chem Eng 4:3140–3150
Zeng D, Zhang Q, Chen S, Liu S, Wang G (2016) Synthesis porous carbon-based solid acid from rice husk for esterification of fatty acids. Micropor Mesopor Mat 219:54–58
Gao Z, Tan S, Cui X, Tian S, Zhang M (2015) Efficient mesoporous carbon-based solid catalyst for the esterification of oleic acid. Fuel 140:669–676
Liu Y, Lotero E, Goodwin JG (2006) Effect of water on sulfuric acid catalyzed esterification. J Mol Catal A Chem 245:132–140
Acknowledgement
This research was supported by the national natural science foundation of China (NO. 21106032) and the education department of Hebei province (NO. ZD2016064).
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Bian, Y., Shan, Q., Guo, C. et al. Biodiesel Production Over Esterification Catalyzed by a Novel Poly(Acidic Ionic Liquid)s. Catal Lett 151, 3523–3531 (2021). https://doi.org/10.1007/s10562-021-03592-x
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DOI: https://doi.org/10.1007/s10562-021-03592-x