Skip to main content
SpringerLink
Log in

Transesterification of Bis 2-Hydroxyethyl Terephthalate for Production of Bis 4-Hydroxybutyl Terephthalate over Homogenous Catalysts

  • Original Article
  • Published:
Korean Journal of Chemical Engineering Aims and scope Submit manuscript

Abstract

The vast amount of PET waste has made an enormous concern owing to its environmental pollution and human health effects. As an eco-friendly alternative option to treat plastic waste, this study investigated the transesterification of bis 2-hydroxyethyl terephthalate (BHET) into bis 4-hydroxybutyl terephthalate (BHBT) using 1, 4-butanediol (BDO) as a solvent in a typical batch reactor at various temperatures. Zinc acetate (Zn-A), antimony (III) oxide, tin (II) chloride, and titanium isopropoxide (Ti-IP) were utilized as catalysts. The effects of the experimental parameters, including the catalyst type, temperature, and catalyst loading, on the transesterification of BHET into BHBT were evaluated. Ti-IP and Zn-A showed higher catalytic activities than the other catalysts. Furthermore, Zn-A demonstrated to be a promising catalyst at lower temperatures, whereas Ti-IP exhibited higher activity at higher temperatures. An increase in temperature improved the yield of BHBT up to (0.99 mol/L) and showed the highest BHET conversion (98.93%) when Ti-IP was used as a catalyst at 210 °C. BHET conversion and the yield of BHBT were raised greatly when the catalyst amount was increased from 0.1 to 0.3 wt%. This study presents the transesterification of BHET using a Ti-IP catalyst as a novel technology for producing valuable BHBT for industrial applications.

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

Access this article

Log in via an institution

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

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5

Similar content being viewed by others

Abbreviations

BHET:

Bis 2-hydroxyethyl terephthalate

BHBT:

Bis 4-hydroxybutyl terephthalate BDO

Zn-A:

Zinc acetate

An-O:

Antimony (III) oxide

Tn-Cl:

Tin (II) chloride

Ti-IP:

Titanium isopropoxide

PET:

Polyethylene terephthalate

r-PET:

Recycled PET

MHET:

Mono-2-hydroxyethyl terephthalate

EG:

Ethylene glycol

PBT:

Polybutylene terephthalate

DMF:

Dimethylformamide

GC/MS:

Gas chromatography–mass spectrometry

THF:

Tetrahydrofuran

HPLC:

High-performance liquid chromatography

HHT:

4-Hydroxybuthyl 2-hydroxyethyl terephthalate

References

  1. C. Schmidt, T. Krauth, S. Wagner, Environ. Sci. Technol. 51, 12246–12253 (2017)

    Article  ADS  CAS  PubMed  Google Scholar 

  2. S. Ion, S. Voicea, C. Sora, G. Gheorghita, M. Tudorache, V.I. Parvulescu, Catal. Today 366, 177–184 (2021)

    Article  CAS  Google Scholar 

  3. G. Phae Chae, C. Won taik, Y. Sunh mo, J. KSWM 29, 583–594 (2012)

    Google Scholar 

  4. K. Kuroda, T. Narihiro, Y. Nakaya, T.Q. Noguchi, R. Maeda, M.K. Nobu, Y. Ohnishi, Y. Kumaki, T. Aizawa, H. Satoh, Chem. Eng. J. 450, 137916 (2022)

    Article  CAS  Google Scholar 

  5. I. Bang hyun, C. Joon hyuk, S. Jae jin, Clean Technol. 13, 244–250 (2007)

    Google Scholar 

  6. N.A. Samak, Y. Jia, M.M. Sharshar, T. Mu, M. Yang, S. Peh, J. Xing, Environ. Int. 145, 106144 (2020)

    Article  CAS  PubMed  Google Scholar 

  7. H. Oh tae, K. Seong cheol, Clean Technol. 15, 245–252 (2009)

    Google Scholar 

  8. Y.-W. Chiao, W. Liao, P.A. Krisbiantoro, B.-Y. Yu, K.C.-W. Wu, Appl. Catal. B 325, 122302 (2023)

    Article  CAS  Google Scholar 

  9. C. Han sang, M. Hee sun, M. Seheum, K. Jae young, J. KSWM 27, 189–195 (2010)

    Google Scholar 

  10. Y.-J. Lee, D.-K. Kim, J.-S. Lee, S.-C. Park, J.-W. Lee, Clean Technol. 19, 313–319 (2013)

    Article  Google Scholar 

  11. X. Cheng, S. Dong, D. Chen, Q. Rui, J. Guo, D. Wang, J. Jiang, Ecotoxicol. Environ. Saf. 187, 109848 (2020)

    Article  CAS  PubMed  Google Scholar 

  12. S. Joo, I.J. Cho, H. Seo, H.F. Son, H.-Y. Sagong, T.J. Shin, S.Y. Choi, S.Y. Lee, K.-J. Kim, Nat. Commun. 9, 382 (2018)

    Article  ADS  PubMed  PubMed Central  Google Scholar 

  13. S. Yoshida, K. Hiraga, T. Takehana, I. Taniguchi, H. Yamaji, Y. Maeda, K. Toyohara, K. Miyamoto, Y. Kimura, K. Oda, Science 351, 1196–1199 (2016)

    Article  ADS  CAS  PubMed  Google Scholar 

  14. J. Huang, D. Yan, H. Dong, F. Li, X. Lu, J. Xin, J. Environ. Chem. Eng. 9, 106277 (2021)

    Article  CAS  Google Scholar 

  15. F. Kawai, T. Kawabata, M. Oda, Appl. Microbiol. Biotechnol. 103, 4253–4268 (2019)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  16. L. Kárpáti, F. Fogarassy, D. Kovácsik, V. Vargha, J. Polym. Environ. 27, 2167–2181 (2019)

    Article  Google Scholar 

  17. M. Dimarogona, E. Nikolaivits, M. Kanelli, P. Christakopoulos, M. Sandgren, E. Topakas, BBA-Gen. Subj. 1850, 2308–2317 (2015)

    Article  CAS  Google Scholar 

  18. X. Li, L. Chen, Y. Ji, M. Li, B. Dong, G. Qian, J. Zhou, X. Dai, Water Res. 171, 115379 (2020)

    Article  CAS  PubMed  Google Scholar 

  19. L. Bai, Z. Liu, C. Yu, M. Ma, S. Chen, Y. Shi, H. He, X. Wang, Polymer 261, 125403 (2022)

    Article  CAS  Google Scholar 

  20. W.S. Lyoo, S.G. Lee, W.S. Ha, J. Lee, J.H. Kim, Polym. Test. 19, 299–309 (2000)

    Article  CAS  Google Scholar 

  21. J. Che, B. Luan, X. Yang, L. Lu, X. Wang, Mater. Lett. 59, 1603–1609 (2005)

    Article  CAS  Google Scholar 

  22. K. Troev, G. Grancharov, R. Tsevi, I. Gitsov, J. Appl. Polym. Sci. 90, 1148–1152 (2003)

    Article  CAS  Google Scholar 

  23. L. Fereidooni, M. Enayati, A. Abbaspourrad, Green Chem. Lett. Rev. 14, 2–14 (2021)

    Article  CAS  Google Scholar 

  24. I. Rizwanul Fattah, H. Ong, T. Mahlia, M. Mofijur, A. Silitonga, S. Rahman, A. Ahmad, Front. Energy Res. 8, 1–17 (2020)

    Article  Google Scholar 

  25. P.E. Young, J. Seung-Mi, K. Yong-Jin, H. Lee Dong, J. KSWM 30, 181–188 (2013)

    Article  Google Scholar 

  26. M. Ghaemy, K. Mossaddegh, Polym. Degrad. Stab. 90, 570–576 (2005)

    Article  CAS  Google Scholar 

  27. H. Wang, Z. Li, Y. Liu, X. Zhang, S. Zhang, Green Chem. 11, 1568–1575 (2009)

    Article  CAS  Google Scholar 

  28. H. Yao, L. Liu, D. Yan, Q. Zhou, J. Xin, X. Lu, S. Zhang, Chem. Eng. Sci. 248, 117109 (2022)

    Article  CAS  Google Scholar 

  29. A. Casas, M.J. Ramos, J.F. Rodríguez, Á. Pérez, Fuel Process. Technol. 106, 321–325 (2013)

    Article  CAS  Google Scholar 

  30. M. North, D.L. Usanov, C. Young, Chem. Rev. 108, 5146–5226 (2008)

    Article  CAS  PubMed  Google Scholar 

  31. E. Lotero, J.G. Goodwin Jr., D.A. Bruce, K. Suwannakarn, Y. Liu, D.E. Lopez, Catalysis 19, 41–83 (2006)

    CAS  Google Scholar 

  32. G. Xi, M. Lu, C. Sun, Polym. Degrad. Stab. 87, 117–120 (2005)

    Article  CAS  Google Scholar 

  33. S. Enthaler, ACS Catal. 3, 150–158 (2013)

    Article  CAS  Google Scholar 

  34. J. Shen, X. Gao, Z. Liu, L. Zhao, Z. Xi, W. Yuan, Chem. Eng. J. 446, 136848 (2022)

    Article  CAS  Google Scholar 

  35. T. Debuissy, E. Pollet, L. Avérous, Eur. Polym. J. 90, 92–104 (2017)

    Article  CAS  Google Scholar 

  36. Y. Wang, D. Wang, M. Tan, B. Jiang, J. Zheng, N. Tsubaki, M. Wu, A.C.S. Appl, Mater. Interfaces 7, 26767–26775 (2015)

    Article  CAS  Google Scholar 

  37. J.M. Encinar, S. Nogales-Delgado, N. Sánchez, J.F. González, Catalysts 10, 366 (2020)

    Article  CAS  Google Scholar 

  38. A.C. Espinosa-López, C.A. Ávila-Orta, F.J. Medellín-Rodríguez, P. González-Morones, C.A. Gallardo-Vega, P.A. De León-Martínez, M. Navarro-Rosales, J.A. Valdez-Garza, Polym. Bull. 76, 2931–2944 (2019)

    Article  Google Scholar 

  39. K. Yang, K. An, C. Choi, S. Jin, C. Kim, J. Appl. Polym. Sci. 60, 1033–1039 (1996)

    Article  CAS  Google Scholar 

  40. L.W. Chen, J.W. Chen, J. Appl. Polym. Sci. 75, 1229–1234 (2000)

    Article  CAS  Google Scholar 

  41. K. Pang, R. Kotek, A. Tonelli, Prog. Polym. Sci. 31, 1009–1037 (2006)

    Article  CAS  Google Scholar 

  42. S. Mohammadi, M. Enayati, Polym. Degrad. Stab. 206, 110180 (2022)

    Article  CAS  Google Scholar 

  43. C.A. Mullen, G.D. Strahan, Y. Elkasabi, J. Anal. Appl. Pyrolysis 164, 105522 (2022)

    Article  CAS  Google Scholar 

  44. J. Yadagiri, V.S. Puppala, H.P.R. Kannapu, V. Vakati, K.S. Koppadi, D.R. Burri, S.R.R. Kamaraju, Catal. Commun. 101, 66–70 (2017)

    Article  CAS  Google Scholar 

  45. D.G. Prakash, K.P. Gopinath, V. Vinatha, S. Shreya, R. Sivaramakrishnan, N.T.L. Chi, Chemosphere 285, 131491 (2021)

    Article  CAS  PubMed  Google Scholar 

  46. J.-Y. Kim, P. Hafezi-Sefat, S. Cady, R.G. Smith, R.C. Brown, Energy Fuels 33, 1248–1255 (2019)

    Article  CAS  Google Scholar 

  47. H. Paysepar, S. Ren, S. Kang, H. Shui, C.C. Xu, J. Anal. Appl. Pyrolysis 134, 301–308 (2018)

    Article  CAS  Google Scholar 

  48. S. Pétursson, Carbohydr. Res. 331, 239–245 (2001)

    Article  PubMed  Google Scholar 

  49. L. Deng, R. Li, Y. Chen, J. Wang, H. Song, J. Mol. Liq. 334, 116419 (2021)

    Article  CAS  Google Scholar 

  50. P. Yuan, B. Liu, Q. Li, H. Sun, J. Chem. Eng. Data 67, 2693–2705 (2022)

    Article  CAS  Google Scholar 

  51. S.R. Tavares, F. Wypych, A.A. Leitao, Mol. Catal. 440, 43–49 (2017)

    Article  CAS  Google Scholar 

  52. G. Impallomeni, G.M. Carnemolla, G. Puzzo, A. Ballistreri, L. Martino, M. Scandola, Polymer 54, 65–74 (2013)

    Article  CAS  Google Scholar 

  53. H. Jeon, M. Han, Korean Chem. Eng. Res. 56, 103–111 (2018)

    CAS  Google Scholar 

  54. Y. Kim, J.G. Verkade. Living polymerization of lactide using titanium alkoxide catalysts, in Macromolecular Symposia (Wiley Online Library, 2005), pp. 105–118

    Google Scholar 

  55. S. Wang, C. Wang, H. Wang, X. Chen, S. Wang, Polym. Degrad. Stab. 114, 105–114 (2015)

    Article  CAS  Google Scholar 

Download references

Acknowledgements

This research is funded by LG Chem. K.R. acknowledges the research fund of Chungnam National University.

Author information

Author notes

  1. Behzad Valizadeh, Suhyeong Chai and Dong Won Chang are co-first authors.

Authors and Affiliations

  1. School of Environmental Engineering, University of Seoul, Seoul, 02504, South Korea

    Behzad Valizadeh, Suhyeong Chai, Dong Won Chang, Sehee Bae, Youngkwon Park & Myung Won Seo

  2. LG Chemical Research Park, TPEE Development Project, Daejeon, 34122, South Korea

    Dae-Chul Kim

  3. Department of Chemical Engineering and Applied Chemistry, Chungnam National University, Daejeon, 34134, South Korea

    Kosan Roh

Authors
  1. Behzad Valizadeh
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Suhyeong Chai
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Dong Won Chang
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Sehee Bae
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Dae-Chul Kim
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Kosan Roh
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Youngkwon Park
    View author publications

    You can also search for this author in PubMed Google Scholar

  8. Myung Won Seo
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding authors

Correspondence to Kosan Roh, Youngkwon Park or Myung Won Seo.

Additional information

Publisher's Note

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

Rights and permissions

Springer Nature or its licensor (e.g. a society or other partner) 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

Valizadeh, B., Chai, S., Chang, D.W. et al. Transesterification of Bis 2-Hydroxyethyl Terephthalate for Production of Bis 4-Hydroxybutyl Terephthalate over Homogenous Catalysts. Korean J. Chem. Eng. 41, 425–433 (2024). https://doi.org/10.1007/s11814-024-00056-x

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11814-024-00056-x

Keywords

Search

Navigation