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Biodiesel Production Over Esterification Catalyzed by a Novel Poly(Acidic Ionic Liquid)s

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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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References

  1. 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

    Article  CAS  Google Scholar 

  2. 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

    Article  CAS  Google Scholar 

  3. 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

    Article  CAS  Google Scholar 

  4. Fangrui MA, Hanna AHB (1999) Biodiesel production: a review. Bioresour Technol 70:1–15

    Article  Google Scholar 

  5. 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

    Article  CAS  Google Scholar 

  6. Hoydonckx HE, De Vos DE, Chavan SA, Jacobs PA (2004) Esterification and transesterification of renewable chemical. Top Catal 27:83–96

    Article  CAS  Google Scholar 

  7. 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

    Article  CAS  Google Scholar 

  8. 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

    Article  CAS  Google Scholar 

  9. 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

    Article  CAS  Google Scholar 

  10. Chen S (2014) Production of Jatropha biodiesel fuel over sulfonic acid-based solid acids. Bioresource Technol 157:346–350

    Article  CAS  Google Scholar 

  11. 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

    CAS  Google Scholar 

  12. 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

    Article  CAS  Google Scholar 

  13. 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

    Article  Google Scholar 

  14. 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

    Article  CAS  Google Scholar 

  15. 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

    Article  CAS  Google Scholar 

  16. 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

    Article  CAS  Google Scholar 

  17. 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

    Article  CAS  Google Scholar 

  18. 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

    Article  CAS  Google Scholar 

  19. 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

    Article  CAS  Google Scholar 

  20. 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

    Article  CAS  Google Scholar 

  21. 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

    Article  CAS  Google Scholar 

  22. 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

    Article  CAS  Google Scholar 

  23. 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

    Article  CAS  Google Scholar 

  24. 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

    Article  CAS  Google Scholar 

  25. 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

    Article  CAS  Google Scholar 

  26. 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

    Article  CAS  Google Scholar 

  27. 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

    Article  CAS  Google Scholar 

  28. 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

    Article  CAS  Google Scholar 

  29. 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

    Article  CAS  Google Scholar 

  30. 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

    Article  CAS  Google Scholar 

  31. Liu Y, Lotero E, Goodwin JG (2006) Effect of water on sulfuric acid catalyzed esterification. J Mol Catal A Chem 245:132–140

    Article  CAS  Google Scholar 

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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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Correspondence to Juan Zhang.

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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

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