Skip to main content
SpringerLink
Log in

Chemical conversion of PET waste using ethanolamine to bis(2-hydroxyethyl) terephthalamide (BHETA) through aminolysis and a novel plasticizer for PVC

  • Original Paper
  • Published:
Iranian Polymer Journal Aims and scope Submit manuscript

Abstract

Poly(ethylene terephthalate) (PET) recycling has been carried out by various methods, e.g., mechanical recycling, chemical recycling and energy recovery method. In this study, chemical recycling of PET was carried out by aminolysis using ethanolamine and converted into bis(2-hydroxyethyl) terephthalamide (BHETA). The reaction was performed by varying the PET:ethanolamine ratio, reaction time and catalyst used for waste medical grade bottles of PET. Yield of about 81 % was obtained for PET:ethanolamine ratio of 1:4 (w/w), with 3 h reaction time, at 160 °C with zinc acetate as a catalyst. BHETA was characterized with FTIR, 1H NMR, and DSC analysis. BHETA was further reacted with heptanoic acid at a molar ratio of 1:2.5. The product obtained was used as a plasticizer for PVC at 5, 10, 15 and 20 parts per hundred (phr) concentration. Thermal and mechanical tests were carried out and the result obtained was compared with the virgin PVC without plasticizer and with conventional plasticizer of PVC, i.e., dioctyl phthalate at 15 phr concentration since new plasticizer showed excellent properties at 15 phr concentration. This newly synthesized plasticizer was completely fused with PVC and in tensile testing helped in increasing the elongation, which was an indication of the plasticization effect shown by this developed material. Glass transition temperature also decreased with an incorporation of the new plasticizer as compared to virgin PVC.

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

Scheme 1
Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7
Fig. 8

Similar content being viewed by others

References

  1. Tawfik ME, Ahmed NM, Eskander SB (2011) Aminolysis of poly(ethylene terephthalate) wastes based on sunlight and utilization of the end product [bis(2-hydroxyethylene) terephthalamide] as an ingredient in the anticorrosive paints for the protection of steel structures. J Appl Polym Sci 120:2842–2855

    Article  CAS  Google Scholar 

  2. Karayannidis GP, Nikolaidis AK, Sideridou ID, Bikiaris DN, Achilias DS (2006) Chemical recycling of PET by glycolysis: polymerization and characterization of the dimethacrylated glycolysate. Macromol Mater Eng 291:1338–1347

    Article  CAS  Google Scholar 

  3. Guclu G (2010) Alkyd resins based on waste PET for water-reducible coating applications. Polym Bull 64:739–748

    Article  CAS  Google Scholar 

  4. Zhou X, Lu X, Wang Q, Zhu M, Li Z (2012) Effective catalysis of poly(ethylene terephthalate) (PET) degradation by metallic acetate ionic liquids. Pure Appl Chem 84:789–801

    Article  CAS  Google Scholar 

  5. Sarker M, Kabir A, Rashid MM, Molla M, Din Mohammad ASM (2011) Waste polyethylene terephthalate (PETE-1) conversion into liquid fuel. J Fundam Renew Energy Appl 1:1–5

    Google Scholar 

  6. Sinha V, Patel MR, Patel JV (2008) PET waste management by chemical recycling: a review. J Polym Environ 18:8–25

    Article  Google Scholar 

  7. Joseph S, Bambola VA, Shertukde VV, Mahanwar PA (2011) Effect of flyash content, particle size of flyash, and type of silane coupling agents on the properties of recycled poly(ethylene terephthalate)/flyash composites. J Appl Polym Sci 119:201–208

    Article  CAS  Google Scholar 

  8. Jain A, Soni RK (2000) Spectroscopic investigation of end products obtained by ammonolysis of poly(ethylene terephthalate) waste in the presence of zinc acetate as a catalyst. J Polym Res 14:475–481

    Article  Google Scholar 

  9. López-Fonseca R, Duque-Ingunza I, De Rivas B, Arnaiz S, Gutiérrez-Ortiz JI (2010) Chemical recycling of post-consumer PET wastes by glycolysis in the presence of metal salts. Polym Degrad Stab 95:1022–1028

    Article  Google Scholar 

  10. Yang Y, Lu Y, Xiang H, Xu Y, Li Y (2002) Study on methanolytic depolymerization of PET with supercritical methanol for chemical recycling. Polym Degrad Stab 75:185–191

    Article  CAS  Google Scholar 

  11. Tawfik ME, Eskander SB (2010) Chemical recycling of poly(ethylene terephthalate) waste using ethanolamine. Sorting of the end products. Polym Degrad Stab 95:187–194

    Article  CAS  Google Scholar 

  12. Parab YS, Pingale ND, Shukla SR (2012) Aminolytic depolymerization of poly(ethylene terephthalate) bottle waste by conventional and microwave irradiation heating. J Appl Polym Sci 125:1103–1107

    Article  CAS  Google Scholar 

  13. Soni RK, Singh S (2005) Synthesis and characterization of terephthalamides from poly(ethylene terephthalate) waste. J Appl Polym Sci 96:1515–1528

    Article  CAS  Google Scholar 

  14. Shukla SR, Harad AM (2006) Aminolysis of polyethylene terephthalate waste. Polym Degrad Stab 91:1850–1854

    Article  CAS  Google Scholar 

  15. Elsaeed SM, Farag RK (2009) Synthesis and characterization of unsaturated polyesters based on the aminolysis of poly(ethylene terephthalate). J Appl Polym Sci 112:3327–3336

    Article  CAS  Google Scholar 

  16. Brydson JA (1999) Plastic materials, 7th edn. Butterworth-Heinemann, Oxford, 7, 12, p 131–132, 331 (Chap.)

  17. Kossarneshan M-T (1993) Analysis of PVC and separation of plasticizer with mixed solvents. Iran Polym J 2:103–105

    Google Scholar 

  18. Shokri AA, Bakhshandeh G, Farahani TD (2006) An investigation of mechanical and rheological properties of NBR/PVC blends: influence of anhydride additives, mixing procedure and NBR form. Iran Polym J 15:227–237

    CAS  Google Scholar 

  19. Shamsi R, Abdouss M, Sadeghi GMM, Taromi FA (2008) Synthesis and characterization of novel polyurethanes based on aminolysis of poly(ethylene terephthalate) wastes, and evaluation of their thermal and mechanical properties. Polym Int 58:22–30

    Article  Google Scholar 

  20. Sadeghi GMM, Shasmi R, Sayaf M (2011) From aminolysis product of PET waste to novel biodegradable polyurethanes. J Polym Environ 19:522–534

    Article  CAS  Google Scholar 

  21. Xi G, Lu M, Sun C (2005) Study on depolymerization of waste polyethylene terephthalate into monomer of bis(2-hydroxyethyl terephthalate). Polym Degrad Stab 87:117–120

    Article  CAS  Google Scholar 

  22. Shukla SR, Pingale ND (2009) Microwave-assisted aminolytic depolymerization of PET waste. Eur Polym J 45:2695–2700

    Article  Google Scholar 

  23. Parab YS, Shah RV, Shukla SR (2012) Microwave irradiated synthesis and characterization of 1,4-phenylene bis-oxazoline form bis-(2-hydroxyethyl) terephthalamide obtained by depolymerization of poly(ethylene terephthalate) (PET) bottle wastes. Curr Chem Lett 1:81–90

    Article  CAS  Google Scholar 

  24. Trivedi NR (2008) In situ forming oral controlled release drug delivery formulations. University of Tennessee, p 1, 15 (Chap.)

Download references

Author information

Authors and Affiliations

  1. Department of Polymer and Surface Engineering, Institute of Chemical Technology, Mumbai, Maharashtra, India

    Aarti P. More, Ravindra A. Kute & Shashank T. Mhaske

Authors
  1. Aarti P. More
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Ravindra A. Kute
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Shashank T. Mhaske
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Shashank T. Mhaske.

Rights and permissions

Reprints and permissions

About this article

Cite this article

More, A.P., Kute, R.A. & Mhaske, S.T. Chemical conversion of PET waste using ethanolamine to bis(2-hydroxyethyl) terephthalamide (BHETA) through aminolysis and a novel plasticizer for PVC. Iran Polym J 23, 59–67 (2014). https://doi.org/10.1007/s13726-013-0200-0

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s13726-013-0200-0

Keywords

Search

Navigation