Abstract
There is a growing interest in the depolymerization of polyethylene terephthalate (PET) waste for both environmental and economic reasons by chemical methods. In this work, PET waste was depolymerized through aminolysis using excess amount of monoethanolamine. Bis (2-hydroxy ethylene) terephthalamide (BHETA) was obtained as the main product. For the first time, the reaction conversion was calculated, by FTIR, DSC, TGA, and CHN methods, and compared with that of measured by conventional gravimetric method. As a result, TGA and DSC are the suitable methods for calculating the reaction conversion. The gravimetric method does not measure reaction conversion, but correctly measure the yield of reaction.
Similar content being viewed by others
References
El Mejjatti A, Harit T, Riahi A, Khiari R, Bouabdallah I, Malek F (2014) Chemical recycling of poly(ethylene terephthalate). Application to the synthesis of multiblock copolyesters. Express Polym Lett 8:544–553
Atta AM, Abdel-Rauf ME, Maysour NE, Abdul-Rahiem AM, Abdel-Azim AAA (2006) Surfactants from recycled poly (ethylene terephthalate) waste as water based oil spill dispersants. J Polym Res 13:39–52
Dutt K, Soni RK (2013) Synthesis and characterization of polymeric plasticizer from PET waste and its applications in nitrile rubber and nitrile-PVC blend. Iran Polym J 22:481–491
Tawfik ME, Tawfic ML (2015) Synthesis and characterization of polysulfone based on poly(ethylene terephthalate) waste. Polym Eng Sci 55:1671–1678
Shukla SR, Harad AM (2006) Aminolysis of polyethylene terephthalate waste. Polym Degrad Stab 91:1850–1854
Geyer B, Lorenz G, Kandelbauer A (2016) Recycling of poly(ethylene terephthalate) – A review focusing on chemical methods. Express Polym Lett 10:559
Kapadi PU, Shukla SR, Mhaske ST, More A (2015) Development of corrosion resistant polyurethane coating from aminolytic depolymerization of pet bottle waste. J Mater Environ Sci 6:119–128
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
El-hameed RSA (2011) Aminolysis of polyethylene terephthalate waste as corrosion inhibitor for carbon steel in HCl corrosive medium. Adv Appl Sci Res 2:483–499
Acar I, Bal A, Güçlü G (2013) The effect of xylene as aromatic solvent to aminoglycolysis of post-consumer PET bottles. Polym Eng Sci 53:2429–2438
Ellison MS, Fisher LD, Alger KW, Zeronian SH (1982) Physical properties of polyester fibers degraded by aminolysis and by alkalin hydrolysis. J Appl Polym Sci 27:247
Collins MJ, Zeronian SH, Marshall ML (1991) Analysis of the molecular weight distributions of aminolyzed poly(ethylene terephthalate) by using gel permeation chromatography. J Macromol Sci A28:775
Overton JR, Haynes SK (1973) Determination of the crystalline fold period in poly(ethylene terephthalate). J Polym Sci Polym Symp 43:9
Awodi YW, Johnson A, Peters RH, Popoola VA (1987) The aminolysis of poly(ethylene terephthalate). J Appl Polym Sci 33:2503
Holmes SA (1996) Aminolysis of poly(ethylene terephthalate) in aqueous amine and amine vapor. J Appl Polym Sci 61:255
Mangovska B, Bogoeva-Gaceva G, Pohlers A (1996) Structure and basic properties of aminated PET. J Appl Polym Sci 62:605
Popoola VA (1988) Polyester formation: Aminolytic degradation and proposed mechanisms of the reaction. J Appl Polym Sci 36:1677
Shukla SR, Kapadi PU, Shashank T (2017) Synthesis of a secondary plasticizer for poly(vinyl chloride) by recycling of poly(ethylene terephthalate) bottle waste through aminolytic depolymerization. J Vinyl Add Technol. https://doi.org/10.1002/vnl.21494
Zahn H, Feifer HP (1963) Aminolysis of polyethylene terephthalate. Polymer 4:429
Magda E, Ahmed TNM, 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
Spychaj T, Fabrycy E, Spychaj S, Kacperski M (2001) Aminolysis and aminoglycolysis of waste poly(ethylene terephthalate). J Mater Cycles Waste Manag 3:24
Zhou J, Li M, Zhang F, Zhang G (2017) Aminolysis of polyethylene terephthalate fabric by a method involving the gradual concentration of dilute ethylenediamine. Coll Surf A Phys Eng Asp 513:146
Acar I, Orbay M (2011) Aminoglycolysis of waste Poly(ethylene terephthalate) (PET) with diethanolamine (DEA) and evaluation of the products as polyurethane surface coating materials. Polym Eng Sci 51:746–754
Acar I, Bal A, Güçl G (2013) The use of intermediates obtained from aminoglycolysis of waste poly(ethylene terephthalate) (PET) for the synthesis of water-reducible alkyd resin. Can J Chem 91:357–363
Bulak E, Acar I (2014) The use of aminolysis, aminoglycolysis and simultaneous aminolysis-hydrolysis products of waste PET for production of paint binder. Polym Eng Sci 54:2273–2281
Shamsi R, Abdouss M, Sadeghi GMM, Taromi FA (2009) 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
Kacperski M, Spychaj T (1999) Rigid polyurethane foams with poly (ethylene terephthalate)/triethanolamine recycling products. Polym Adv Tech 10:620
Cuong HN, Yen DH (2017) Aminolysis of poly(ethylene terephthalate) waste bottle with tetra/hexamethylene diamine and characterization of alpha, ohmega-diamine products. Sci Technol Develop 20:T101
More AP, Kokate SR, Rane PC, Mhaske ST (2017) Studies of different techniques of aminolysis of poly(ethylene terephthalate) with ethylenediamine. Polym Bull 74:3269–3282
Sarkar K, Krishna Meka SR, Bagchi A, Krishna NS, Ramachandra SG, Madras G, Chatterjee K (2014) Polyester derived from recycled poly(ethylene terephthalate) waste for regenerative medicine. RSC Adv 4:58805–58815
More AP, Kute RA, Mhaske ST (2014) 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
Chen F, Zhou Q, Bu R, Yang F, Li W (2015) Kinetics of poly(ethylene terephthalate) fiber glycolysis in ethylene glycol. Fibers Polym 16:1213–1219
Al-Mulla A, Shaban HI (2007) Degradation kinetics of poly(ethylene terephthalate) and poly (methyl methacrylate) blends. Polym Bull 58:893–902
Tawfik ME, Eskander SB (2010) Chemical recycling of poly(ethylene terephthalate) waste using ethanolamine Sorting of the end products. Polym Degrad Stab 95:187–194s
Author information
Authors and Affiliations
Corresponding author
Additional information
Publisher's Note
Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
Rights and permissions
About this article
Cite this article
Ghorbantabar, S., Ghiass, M., Yaghobi, N. et al. Investigation of conventional analytical methods for determining conversion of polyethylene terephthalate waste degradation via aminolysis process. J Mater Cycles Waste Manag 23, 526–536 (2021). https://doi.org/10.1007/s10163-020-01149-5
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10163-020-01149-5