Skip to main content
Log in

The Synthesis of Ionic Liquid Functionalized Polymer and its Application in the Esterification Between Methacrylic Acid and Methanol

  • Published:
Catalysis Letters Aims and scope Submit manuscript

Abstract

High yield of methyl methacrylate was gained by using ionic liquid functionalized copolymer of ethylene dimethacrylate and 4-vinylbenzyl. The solid acid catalyst (VEM-ILs) was obtained through quaternary ammonization on the tetraethylenepentamine-functionalized copolymer with 1,3-propanesultone and HSO3CF3. The acid amount of VEM-ILs was 1.46 mmol/g. The surface area and pore volume of VEM-ILs were 11.1 m2/g and 0.04 cm3/g. To appraise the catalytic activity of the catalyst, the esterification between methacrylic acid and methanol was implemented. The optimized condition was as follows: 21.15 wt% catalyst dosage based on the weight of methacrylic acid, 90 °C, MAA to MeOH ratio of 1:1.5 and 3 h reaction time. Under the optimal condition, the yield of ester reached 76.5%. After four times use, the catalyst still exhibited a good catalytic effect.

Graphical Abstract

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7
Fig. 8
Fig. 9
Fig. 10

Similar content being viewed by others

References

  1. Li M, Chen J, Li L, Ye C, Lin X, Qiu T (2021) Novel multi -SO3H functionalized ionic liquids as highly efficient catalyst for synthesis of biodiesel. Green Energy Environ 2:271–282

    Article  Google Scholar 

  2. Song J, Peng Z, Zhang Y (2020) Enhancement of thermal conductivity and mechanical properties of silicone rubber composites by using acrylate grafted siloxane copolymers. Chem Eng J 391:123476

    Article  CAS  Google Scholar 

  3. Wang R, Zhu Z, Qiu X, Bai L, Guo W, Zuo L, Zhao T, Shan G (2019) Determination of epoxide impurity in sarpogrelate hydrochloride intermediate by UHPLC and column-switching liquid chromatography. J Pharmceut Biomed 174:57–62

    Article  CAS  Google Scholar 

  4. Herbers S, Wachsmuth D, Obenchain D, Grabow J (2018) Rotational characterization of methyl methacrylate: internal dynamic sand structure determination. J Mol Spectrosc 343:96–101

    Article  CAS  Google Scholar 

  5. Li Z, Wang Z, Wang C, Ding S, Li F, Lin H (2019) Preparation of magnetic resin microspheres M-P(MMA-DVB-GMA) and the adsorption property to heavy metal ions. Appl Surf Sci 496:143708

    Article  CAS  Google Scholar 

  6. Bhanvase B, Pinjari D, Gogate P, Sonawane S, Pandit A (2012) Synthesis of exfoliated poly(styrene-co-methyl methacrylate)/montmorillonite nanocomposite using ultrasound assisted in situ emulsion copolymerization. Chem Eng J 2012:770–778

    Article  Google Scholar 

  7. Al-Muhtaseb A, Ibrahim K, Albadarin A, Ali-khashman O, Walker G, Ahmad M (2011) Remediation of phenol-contaminated water by adsorption using poly(methyl methacrylate) (PMMA). Chem Eng J 168:691–699

    Article  CAS  Google Scholar 

  8. Konwar L, Mäki-Arvela P, Salminen E, Kumar N, Thakur A, Mikkola J, Deka D (2015) Towards carbon efficient biorefining: multifunctional mesoporous solid acids obtained from biodiesel production wastes for biomass conversion. Appl Catal B 176–177:20–35

    Article  Google Scholar 

  9. Zhou S, Liu X, Lai J, Zheng M, Liu W, Xu Q, Yin D (2019) Covalently linked organo-sulfonic acid modified titanate nanotube hybrid nanostructures for the catalytic esterification of levulinic acid with n-butyl alcohol. Chem Eng J 361:571–577

    Article  CAS  Google Scholar 

  10. Bian Y, Zhang J, Zhang S, Liu C, Zhao D (2019) Synthesis of polyionic liquid by phenolic condensation and its application in esterification. ACS Sustainable Chem Eng 20:17220–17226

    Article  Google Scholar 

  11. Sangar S, Lan C, Razali S, Farabi M, Taufiq-Yap Y (2019) Methyl ester production from palm fatty acid distillate (PFAD) using sulfonated cow dung-derived carbon-based solid acid catalyst. Energ Convers Manage 2019:1306–1315

    Article  Google Scholar 

  12. Fan M, Si Z, Sun W, Zhang P (2019) Sulfonated ZrO2-TiO2 nanorods as efficient solid acid catalysts for heterogeneous esterification of palmitic acid. Fuel 252:254–261

    Article  CAS  Google Scholar 

  13. Zhang H, Tian F, Xu L, Peng R, Deng J (2020) Batch and continuous esterification for the direct synthesis of high qualified biodiesel from waste cooking oils (WCO) with Amberlyst-15/Poly (vinyl alcohol) membrane as a bifunctional catalyst. Chem Eng J 388:124214

    Article  CAS  Google Scholar 

  14. Rattanaphra D, Harvey A, Srinophakun P (2010) Simultaneous conversion of triglyceride/free fatty acid mixtures into biodiesel using sulfated zirconia. Top Catal 53:773–781

    Article  CAS  Google Scholar 

  15. 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 

  16. Lokman I, Rashid U, Taufiq-Yap Y, Yunus R (2015) Methyl ester production from palm fatty acid distillate using sulfonated glucose-derived acid catalyst. Renew Energ 81:347–354

    Article  CAS  Google Scholar 

  17. Wang RZ, Chen GZ, Qin H, Chen HY, Chen LF, Qi ZW (2021) Systematic screening of bifunctional ionic liquid for intensifying esterification of methyl heptanoate in the reactive extraction process. Chem Eng Sci 246:116888

    Article  CAS  Google Scholar 

  18. Wang RZ, Qin H, Wang JW, Cheng HY, Chen LF, Qi ZW (2021) Reactive extraction for intensifying 2-ethylhexyl acrylate synthesis using deep eutectic solvent [Im:2PTSA]. Green Energy Environ 6:405–412

    Article  CAS  Google Scholar 

  19. Sahoo S, Kumar P, Lefebvre F, Halligudi S (2009) Oxidative kinetic resolution of alcohols using chiral Mn–salen complex immobilized onto ionic liquid modified silica. Appl Catal A Gen 354:17–25

    Article  CAS  Google Scholar 

  20. Khiratkar A, Balinge K, Krishnamurthy M, Cheralathan K, Patle D, Singh V, Arora S, Bhagat P (2018) Sulphonic acid-functionalized benzimidazolium based poly ionic liquid catalyzed esterification of levulinic acid. Catal Lett 148:680–690

    Article  CAS  Google Scholar 

  21. Huang TC, Qin H, Wang RZ, Cheng HY, Chen LF, Qi ZW (2021) Liquid−liquid equilibrium for the esterification system of acrylic acid with n-Butanol Catalyzed by ionic liquid [BMIm][HSO4] at atmospheric pressure. J Chem Eng Data 66:2764–2772

    Article  CAS  Google Scholar 

  22. Domańska U, Królikowska M, Pobudkowska A, Królikowski M, Więckowski M (2019) Physico-chemical properties of ionic liquids: density, viscosity, density at high pressure, surface tension, octan-1-ol/water partition coefficients and thermodynamic models. Fluid Phase Equilibr 502:112304

    Article  Google Scholar 

  23. Boldrini D, Angeletti S, Cervellini P, Reinoso D (2019) Highly ordered mesoporous Al-MCM-41 synthesis through valorization of natural sediment. ACS Sustainable Chem Eng 7:4684–4691

    Article  CAS  Google Scholar 

  24. Pan H, Li H, Zhang H, Wang AP, 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 

  25. Peng WL, Mi JX, Liu FJ, Xiao Y, Chen W, Liu ZQ, Yi XF, Liu WT, Zheng AM (2020) Accelerating biodiesel catalytic production by confined activation of methanol over high-concentration ionic liquid-grafted UiO-66 solid superacids. ACS Catal 10:11848–11856

    Article  CAS  Google Scholar 

  26. 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 

  27. Coleman D, Gathergood N (2010) Biodegradation studies of ionic liquids. Chem Soc Rev 39:600–637

    Article  CAS  PubMed  Google Scholar 

  28. Leng P, Jiang P, Wang J (2012) A novel Brønsted acidic heteropolyanion-based polymeric hybridcatalyst for esterification. Catal Commun 25:41–44

    Article  CAS  Google Scholar 

  29. Wang Y, Xu B, Du Y, Zhang S (2018) Heterogeneous cyclization of sorbitol to isosorbide catalyzed by a novel basic porous polymer-supported ionic liquid. Mol Catal 457:59–66

    Article  CAS  Google Scholar 

  30. Bian Y, Shan Q, Guo C, Liu C, Zhang J (2021) Biodiesel production over esterifcation catalyzed by a novel poly acidic ionic liquids. Catal Lett 151:3523–3531

    Article  CAS  Google Scholar 

  31. Yao C, Hou Y, Ren S, Wu W, Ji Y, Liu H (2018) Sulfonate based zwitterions: A new class of extractants for separating phenols from oils with high efficiency via forming deep eutectic solvents. Fuel Process Technol 178:206–212

    Article  CAS  Google Scholar 

  32. Gao HY, Zhou YM, Sheng XL, Zhao S, Zhang C, Fang JS (2018) Wang BB Alkylation of O-xylene and styrene catalyzed by cross-linked poly acidic ionic liquids catalyst with novel mesoporous-macroporous structure. Appl Catal A 552:138–146

    Article  CAS  Google Scholar 

  33. Wu FK, Li G, Tong HJ, Wu S (2011) Synthesis of Brønsted acidic ionic liquid [HMIPS]OTs and its application for esterifications. Speciality Petrochem 28:6–10

    Google Scholar 

  34. Ran R, Li J, Wang G, Li ZX (2019) Li CS Esterification of methacrylic acid with methanol: process optimization, kinetic modeling, and reactive distillation. Ind Eng Chem Res 58:2135–2145

    Article  CAS  Google Scholar 

  35. Wang G, Cai GM (2021) Cooperative catalytic effects between Brønsted and Lewis acid sites and kinetics for production of methyl methacrylate on SO42−/TiO2-SiO2. Chem Eng Sci 229:116165

    Article  CAS  Google Scholar 

  36. Chang BB, Fu J, Tian YL (2013) Dong XP Multifunctionalized ordered mesoporous carbon as an efficient and stable solid acid catalyst for biodiesel preparation. J Phys Chem C 117:6252–6258

    Article  CAS  Google Scholar 

  37. Guo F, Xiu ZL (2012) Liang ZX Synthesis of biodiesel from acidified soybean soapstock using a lignin-derived carbonaceous catalyst. Appl Energy 98:47–52

    Article  CAS  Google Scholar 

Download references

Acknowledgements

the National Natural Science Fund for Distinguished Young Scholars (22025803), Supported by Hebei Natural Science Foundation (B2021103012) supported by the Innovation Academy for Green Manufacture, Chinese Academy of Sciences (IAGM-2019-A14). Supported by the Joint Fund of the Yulin University and the Dalian National Laboratory for Clean Energy(Grant. YLU-DNL Fund 2021018)

Author information

Authors and Affiliations

Authors

Corresponding authors

Correspondence to Zhijian Peng or Chunshan Li.

Ethics declarations

Conflict of interest

The authors declare that they have no conflict of interest.

Additional information

Publisher's Note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Supplementary Information

Below is the link to the electronic supplementary material.

Supplementary file1 (TIF 3368 KB)

Rights and permissions

Springer Nature or its licensor holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law.

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Bian, Y., Liu, J., Zhang, G. et al. The Synthesis of Ionic Liquid Functionalized Polymer and its Application in the Esterification Between Methacrylic Acid and Methanol. Catal Lett 153, 1657–1665 (2023). https://doi.org/10.1007/s10562-022-04099-9

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10562-022-04099-9

Keywords

Navigation