SpringerLink
Log in

Kinetic modeling of glycerol acetylation catalyzed by styrene–divinylbenzene and styrene-trimethylolpropane triacrylate sulfonated resins

  • Published:
Reaction Kinetics, Mechanisms and Catalysis Aims and scope Submit manuscript

Abstract

The present work reports a kinetic comparison between two resins made with different cross-linkers, Amberlyst 36 and PS-TMPTA. The latter was synthesized in this study. Both resins were used as catalysts in glycerol acetylation in a batch reactor at 80 and 90 °C, with 5 and 10 g L−1 of catalyst concentration under a molar ratio 4:1 of acetic acid/glycerol. The synthesized resin (PS-TMPTA) presented low ion exchange capacity (1.5 mmol g−1) compared to the commercial resin (Amberlyst 36, 5.45 mmol g−1), but both presented similar efficiency in catalysis, probably due to the difference in cross-linking densities. The experimental results explain the resins’ behavior and properties in detail (ion exchange capacities, swelling index and catalytic efficiency) and the kinetic models were compared utilizing the difference between the corrected Akaike Information Criterion (ΔAICc), Standard Deviation (s) and P-value (student t distribution). According to the results, the irreversible first order model had the best fit of the two models for the experimental conditions studied for this work.

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

Access this article

Log in via an institution

Subscribe and save

Springer+ Basic
EUR 32.99 /Month
  • Get 10 units per month
  • Download Article/Chapter or Ebook
  • 1 Unit = 1 Article or 1 Chapter
  • Cancel anytime
Subscribe now

Buy Now

Price includes VAT (Canada)

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2
Fig. 3
Fig. 4

Similar content being viewed by others

References

  1. Galan MI, Bonet J, Sire R et al (2009) (2009) From residual to useful oil: revalorization of glycerine from the biodiesel synthesis. Bioresour Technol 100(15):3775–3778. https://doi.org/10.1016/j.biortech.2009.01.066

    Article  CAS  PubMed  Google Scholar 

  2. Simasatitkula L, Arpornwichanop A (2019) Feasibility study of using waste cooking oil and byproduct from palm oil refinery for green diesel production. Chem Eng Trans. https://doi.org/10.3303/CET1974001

    Article  Google Scholar 

  3. Okoye PU, Abdullah AZ, Hameed BH (2017) Synthesis of oxygenated fuel additives via glycerol esterification with acetic acid over bio-derived carbon catalyst. Fuel 209:538–544. https://doi.org/10.1016/j.fuel.2017.08.024

    Article  CAS  Google Scholar 

  4. Tran TTV, Obpirompoo M, Kongparakul S et al (2020) Glycerol valorization through production of di-glyceryl butyl ether with sulfonic acid functionalized KIT-6 catalyst. Carbon Resour Convers 3:182–189. https://doi.org/10.1016/j.crcon.2020.12.003

    Article  CAS  Google Scholar 

  5. Liao X, Zhu Y, Wang SG et al (2009) Producing triacetylglycerol with glycerol by two steps: esterification and acetylation. Fuel Process Technol 90(7–8):988–993. https://doi.org/10.1016/j.fuproc.2009.03.015

    Article  CAS  Google Scholar 

  6. Setyaningsih L, Siddiq F, Pramezy A (2018) Esterification of glycerol with acetic acid over Lewatit catalyst. MATEC Web Conf 154:01028. https://doi.org/10.1051/matecconf/201815401028

    Article  CAS  Google Scholar 

  7. Zhou L, Nguyen TH (2012) Adesina AA (2012) The acetylation of glycerol over amberlyst-15: kinetic and product distribution. Fuel Process Technol 104:310–318. https://doi.org/10.1016/j.fuproc.2012.06.001

    Article  CAS  Google Scholar 

  8. Banu I, Bumbac G, Bombos D et al (2020) Glycerol acetylation with acetic acid over Purolite CT-275. Product yields and process kinetics. Renew Energy 148:548–557. https://doi.org/10.1016/j.renene.2019.10.060

    Article  CAS  Google Scholar 

  9. Carpegiani JA, Godoy WM, Guimarães DHP, Aguiar LG (2020) Glycerol acetylation catalyzed by an acidic styrene-co-dimethacrylate resin: experiments and kinetic modeling. React Kinet Mech Cat 130:447–461. https://doi.org/10.1007/s11144-020-01788-7

    Article  CAS  Google Scholar 

  10. Mekala M, Thamida SK (2013) Goli VL (2013) Pore diffusion model to predict the kinetics of heterogeneous catalytic esterification of acetic acid and methanol. Chem Eng Sci 104:565–573. https://doi.org/10.1016/j.ces.2013.09.039

    Article  CAS  Google Scholar 

  11. Godoy WM, Castro G, Nápolis L, Carpegiani JA et al (2020) Synthesis of sulfonated Poly[Styrene-co-(Trimethylolpropane Triacrylate)] and application in the catalysis of glycerol acetylation. Macromol Symp 394(1):1900169. https://doi.org/10.1002/masy.201900169

    Article  CAS  Google Scholar 

  12. Penariol JL, Theodoro TR, Dias JR et al (2019) application of a sulfonated styrene–(Ethylene Glycol Dimethacrylate) resin as catalyst. Kinet Catal 60(5):650–653. https://doi.org/10.1134/S0023158419050057

    Article  CAS  Google Scholar 

  13. Silva VFL, Penariol JL, Dias JR et al (2019) Sulfonated Styrene-Dimethacrylate resins with improved catalytic activity. Kinet Catal 60(5):654–660. https://doi.org/10.1134/S0023158419050112

    Article  CAS  Google Scholar 

  14. Gomes FM, Pereira FM, Silva A (2019) Multiple response optimization: analysis of genetic programming for symbolic regression and assessment of desirability functions. Knowl-Based Syst 179:21–33. https://doi.org/10.1016/j.knosys.2019.05.002

    Article  Google Scholar 

  15. Mufrodi Z, Rochmadi S, Budiman A (2012) Chemical kinetics for synthesis of triacetin from biodiesel byproduct. Int J Chem 4(2):101–107. https://doi.org/10.5539/ijc.v4n2p101

    Article  CAS  Google Scholar 

  16. Aguiar L, Moura JOV, Theodoro TR (2017) Prediction of resin textural properties by vinyl/divinyl copolymerization modeling. Polymer 129:21–31. https://doi.org/10.1016/j.polymer.2017.09.042

    Article  CAS  Google Scholar 

  17. Coutinho FMB, Rezende SM (2006) Soares BG (2006) Characterization of sulfonated poly (styrene-divinylbenzene) and poly(divinylbenzene) and its application as catalysts in esterification reaction. J Appl Polym Sci 102(4):3616–3627. https://doi.org/10.1002/app.24046

    Article  CAS  Google Scholar 

  18. Kunin R (1972) Ion Exchange Resins. Robert E Krieger Publ Co, New York

    Google Scholar 

  19. Theodoro TR, Moura JOV, Dias JR et al (2021) Mathematical modeling of Poly[styrene-co-(ethylene glycol dimethacrylate)] sulfonation. Kinet Catal 62(1):188–195. https://doi.org/10.1134/S0023158421010092

    Article  CAS  Google Scholar 

  20. Ferreira P, Fonseca IM, Ramos AM (2009) Esterification of glycerol with acetic acid over dodecamolybdophosphoric acid encaged in USY zeolite. Catal Commun 10(5):481–484. https://doi.org/10.1016/j.catcom.2008.10.015

    Article  CAS  Google Scholar 

  21. Fogler HS (2006) Elements of chemical reaction engineering, 4th edn. Prentice Hall PTR, Upper Saddle River

    Google Scholar 

  22. Luenberger DG, Ye Y (2016) Linear and nonlinear programming, 4th edn. Springer International Publishing, New Jersey

    Book  Google Scholar 

  23. Montgomery D, Runger GC (2018) Applied statistics and probability for engineers, 7th edn. Wiley, Hoboken

    Google Scholar 

  24. Aguiar LG, Godoy WM, Nápolis L et al (2021) Modeling the effect of cross-link density on resins catalytic activities. Ind Eng Chem Res 60(17):6101–6110. https://doi.org/10.1021/acs.iecr.1c0095

    Article  CAS  Google Scholar 

  25. Moreira MN, Corrêa I, Ribeiro AM et al (2020) Solketal production in a fixed bed adsorptive reactor through the ketalization of glycerol. Ind Eng Chem Res 59(7):2805–2816. https://doi.org/10.1021/acs.iecr.9b06547

    Article  CAS  Google Scholar 

Download references

Acknowledgements

The authors would like to thank FAPESP (Grant No 2017/26985-4) for the financial support.

Author information

Authors and Affiliations

  1. Department of Chemical Engineering, Engineering School of Lorena, University of São Paulo, Lorena, SP, 12602-810, Brazil

    William M. Godoy, Juliana A. Carpegiani, Félix M. Pereira, Daniela H. P. Guimarães & Leandro G. Aguiar

Authors
  1. William M. Godoy
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Juliana A. Carpegiani
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Félix M. Pereira
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Daniela H. P. Guimarães
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Leandro G. Aguiar
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Leandro G. Aguiar.

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 (DOCX 33 KB)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Godoy, W.M., Carpegiani, J.A., Pereira, F.M. et al. Kinetic modeling of glycerol acetylation catalyzed by styrene–divinylbenzene and styrene-trimethylolpropane triacrylate sulfonated resins. Reac Kinet Mech Cat 135, 233–245 (2022). https://doi.org/10.1007/s11144-021-02141-2

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11144-021-02141-2

Keywords

Search

Navigation