Towards recycling purpose: Converting PET plastic waste back to terephthalic acid using pH-responsive phase transfer catalyst

doi:10.1016/j.cjche.2021.10.028

Chinese Journal of Chemical Engineering ›› 2022, Vol. 51 ›› Issue (11): 53-60.DOI: 10.1016/j.cjche.2021.10.028

Previous Articles Next Articles

Towards recycling purpose: Converting PET plastic waste back to terephthalic acid using pH-responsive phase transfer catalyst

Yueqing Wang¹, Hongxing Wang², Hongmei Chen³, Hantao Liu¹

1. School of Energy and Power Engineering, North University of China, Taiyuan 030051, China;
2. State Key Laboratory of Coal Conversion, Institute of Coal Chemistry, Chinese Academy of Sciences, Taiyuan 030001, China;
3. School of Instrument and Electronics, North University of China, Taiyuan 030051, China

Received:2021-07-13 Revised:2021-10-14 Online:2023-01-18 Published:2022-11-18
Contact: Yueqing Wang,E-mail:yueqingwang@nuc.edu.cn;Hantao Liu,E-mail:rcspseet@126.com
Supported by:
This work thanks to the support of the National Natural Science Foundation of China (22005276).

Towards recycling purpose: Converting PET plastic waste back to terephthalic acid using pH-responsive phase transfer catalyst

Yueqing Wang¹, Hongxing Wang², Hongmei Chen³, Hantao Liu¹

1. School of Energy and Power Engineering, North University of China, Taiyuan 030051, China;
2. State Key Laboratory of Coal Conversion, Institute of Coal Chemistry, Chinese Academy of Sciences, Taiyuan 030001, China;
3. School of Instrument and Electronics, North University of China, Taiyuan 030051, China

通讯作者: Yueqing Wang,E-mail:yueqingwang@nuc.edu.cn;Hantao Liu,E-mail:rcspseet@126.com
基金资助:
This work thanks to the support of the National Natural Science Foundation of China (22005276).

Abstract

Abstract: Converting polyethylene terephthalate (PET) wastes to its monomer and valuable chemicals via eco-friendly chemical method is still a challenge task. Previously, phase transfer catalysts used for alkaline hydrolysis were soluble in reaction media and hardly separated after reaction. Here, we reported several pH-responsive catalysts combined alkyl quaternary ammonium units with heteropolyacid anion for achieving stepwise product/catalyst separation and catalyst recycling. The properties of homogeneous/heterogeneous transfer behavior allow catalyst to be easily separated from reaction media by adjusting of pH value. Among them, [C₁₆H₃₃N(CH₃)₃]₃PW₁₂O₄₀ (abbreviated as [CTA]₃PW) exhibits the highest activity and the most suitable pH responsive values. Such a pH triggered switchable catalytic system not only shows good performance for depolymerization of pure PET, but also some real PET wastes such as coloured trays and PE/PET complex films could be completely degraded into terephthalic acid. Additionally, the reaction kinetics and activation energy of PET alkaline hydrolysis also studied with and without pH-responsive [CTA]₃PW.

Key words: Polyethylene terephthalate, Alkaline hydrolysis, pH-responsive catalyst, Terephthalic acid

摘要： Converting polyethylene terephthalate (PET) wastes to its monomer and valuable chemicals via eco-friendly chemical method is still a challenge task. Previously, phase transfer catalysts used for alkaline hydrolysis were soluble in reaction media and hardly separated after reaction. Here, we reported several pH-responsive catalysts combined alkyl quaternary ammonium units with heteropolyacid anion for achieving stepwise product/catalyst separation and catalyst recycling. The properties of homogeneous/heterogeneous transfer behavior allow catalyst to be easily separated from reaction media by adjusting of pH value. Among them, [C₁₆H₃₃N(CH₃)₃]₃PW₁₂O₄₀ (abbreviated as [CTA]₃PW) exhibits the highest activity and the most suitable pH responsive values. Such a pH triggered switchable catalytic system not only shows good performance for depolymerization of pure PET, but also some real PET wastes such as coloured trays and PE/PET complex films could be completely degraded into terephthalic acid. Additionally, the reaction kinetics and activation energy of PET alkaline hydrolysis also studied with and without pH-responsive [CTA]₃PW.

关键词: Polyethylene terephthalate, Alkaline hydrolysis, pH-responsive catalyst, Terephthalic acid

Yueqing Wang, Hongxing Wang, Hongmei Chen, Hantao Liu. Towards recycling purpose: Converting PET plastic waste back to terephthalic acid using pH-responsive phase transfer catalyst[J]. Chinese Journal of Chemical Engineering, 2022, 51(11): 53-60.

References

[1] A.J. Martín, C. Mondelli, S.D. Jaydev, J. Pérez-Ramírez, Catalytic processing of plastic waste on the rise, Chem 7 (6) (2021) 1487-1533
[2] D. Danso, J. Chow, W.R. Streit, Plastics:Environmental and biotechnological perspectives on microbial degradation, Appl. Environ. Microbiol. 85 (19) (2019) aem.01095-19
[3] V. Tournier, C.M. Topham, A. Gilles, B. David, C. Folgoas, E. Moya-Leclair, E. Kamionka, M.L. Desrousseaux, H. Texier, S. Gavalda, M. Cot, E. Guémard, M. Dalibey, J. Nomme, G. Cioci, S. Barbe, M. Chateau, I. André, S. Duquesne, A. Marty, An engineered PET depolymerase to break down and recycle plastic bottles, Nature 580 (7802) (2020) 216-219
[4] Y.C. Liu, X.Q. Yao, H.Y. Yao, Q. Zhou, J.Y. Xin, X.M. Lu, S.J. Zhang, Degradation of poly(ethylene terephthalate) catalyzed by metal-free choline-based ionic liquids, Green Chem. 22 (10) (2020) 3122-3131
[5] C. Pudack, M. Stepanski, P. Fässler, PET recycling-contributions of crystallization to sustainability, Chemie Ingenieur Tech. 92 (4) (2020) 452-458
[6] S.C. Kosloski-Oh, Z.A. Wood, Y. Manjarrez, J.P. de los Rios, M.E. Fieser, Catalytic methods for chemical recycling or upcycling of commercial polymers, Mater. Horiz. 8 (4) (2021) 1084-1129
[7] A.B. Raheem, Z.Z. Noor, A. Hassan, M.K. Abd Hamid, S.A. Samsudin, A.H. Sabeen, Current developments in chemical recycling of post-consumer polyethylene terephthalate wastes for new materials production:A review, J. Clean. Prod. 225 (2019) 1052-1064
[8] Y.X. Jing, Y.Q. Wang, S. Furukawa, J. Xia, C.Y. Sun, M.J. Hülsey, H.F. Wang, Y. Guo, X.H. Liu, N. Yan, Towards the circular economy:Converting aromatic plastic waste back to arenes over a Ru/Nb₂ O₅ catalyst, Angew Chem Int Ed Engl 60 (10) (2021) 5527-5535
[9] S.L. Lu, Y.X. Jing, B. Feng, Y. Guo, X.H. Liu, Y.Q. Wang, H 2 -free plastic conversion:Converting PET back to BTX by unlocking hidden hydrogen, ChemSusChem 14 (19) (2021) 4242-4250
[10] Y. Kratish, J.Q. Li, S.F. Liu, Y.S. Gao, T.J. Marks, Polyethylene terephthalate deconstruction catalyzed by a carbon-supported single-site molybdenum-dioxo complex, Angew. Chem. 132 (45) (2020) 20029-20033
[11] F. Kawai, T. Kawabata, M. Oda, Current state and perspectives related to the polyethylene terephthalate hydrolases available for biorecycling, ACS Sustainable Chem. Eng. 8 (24) (2020) 8894-8908
[12] M. O'Reilly, J. Stubbe, PET polymer recycling, Biochemistry 59 (25) (2020) 2316-2318
[13] S.A. Kulyukhin, A.V. Gordeev, A.F. Seliverstov, Gas-phase treatment of polyethylene terephthalate waste in nitrating atmosphere for recycling purposes, J. Hazard. Mater. 400 (2020) 123268
[14] B. Geyer, G. Lorenz, A. Kandelbauer, Recycling of poly(ethylene terephthalate)-A review focusing on chemical methods, Express Polym. Lett. 10 (7) (2016) 559-586
[15] X.C. Jiao, K. Zheng, Z.X. Hu, S. Zhu, Y.F. Sun, Y. Xie, Conversion of waste plastics into value-added carbonaceous fuels under mild conditions, Adv. Mater. 33(50) (2021) e2005192
[16] B. Shojaei, M. Abtahi, M. Najafi, Chemical recycling of PET:A stepping-stone toward sustainability, Polym. Adv. Technol. 31 (12) (2020) 2912-2938
[17] T. Yoshioka, T. Sato, A. Okuwaki, Hydrolysis of waste PET by sulfuric acid at 150℃ for a chemical recycling, J. Appl. Polym. Sci. 52 (9) (1994) 1353-1355
[18] T. Yoshioka, N. Okayama, A. Okuwaki, Kinetics of hydrolysis of PET powder in nitric acid by a modified shrinking-core model, Ind. Eng. Chem. Res. 37 (2) (1998) 336-340
[19] M.J. Kang, H.J. Yu, J. Jegal, H.S. Kim, H.G. Cha, Depolymerization of PET into terephthalic acid in neutral media catalyzed by the ZSM-5 acidic catalyst, Chem. Eng. J. 398 (2020) 125655
[20] S. Ügdüler, K.M. van Geem, R. Denolf, M. Roosen, N. Mys, K. Ragaert, S. de Meester, Towards closed-loop recycling of multilayer and coloured PET plastic waste by alkaline hydrolysis, Green Chem. 22 (16) (2020) 5376-5394
[21] G.P. Karayannidis, D.S. Achilias, Chemical Recycling of Poly(ethylene terephthalate), Macromol. Mater. Eng. 292 (2) (2007) 128-146
[22] S. Mishra, A.S. Goje, Chemical recycling, kinetics, and thermodynamics of alkaline depolymerization of waste poly (ethylene terephthalate) (PET), Polym. React. Eng. 11 (4) (2003) 963-987
[23] G.P. Karayannidis, A.P. Chatziavgoustis, D.S. Achilias, Poly(ethylene terephthalate) recycling and recovery of pure terephthalic acid by alkaline hydrolysis, Adv. Polym. Technol. 21 (4) (2002) 250-259
[24] H.I. Khalaf, O.A. Hasan, Effect of quaternary ammonium salt as a phase transfer catalyst for the microwave depolymerization of polyethylene terephthalate waste bottles, Chem. Eng. J. 192 (2012) 45-48
[25] N.R. Paliwal, A.K. Mungray, Ultrasound assisted alkaline hydrolysis of poly(ethylene terephthalate) in presence of phase transfer catalyst, Polym. Degrad. Stab. 98 (10) (2013) 2094-2101
[26] X.M. Yan, P. Mei, J.H. Lei, Y.Z. Mi, L. Xiong, L.P. Guo, Synthesis and characterization of mesoporous phosphotungstic acid/TiO₂ nanocomposite as a novel oxidative desulfurization catalyst, J. Mol. Catal. A:Chem. 304 (1-2) (2009) 52-57
[27] D. Huang, Y.J. Wang, L.M. Yang, G.S. Luo, Direct synthesis of mesoporous TiO₂ modified with phosphotungstic acid under template-free condition, Microporous Mesoporous Mater. 96 (1-3) (2006) 301-306
[28] N.R. Shiju, H.M. Williams, D.R. Brown, Cs exchanged phosphotungstic acid as an efficient catalyst for liquid-phase Beckmann rearrangement of oximes, Appl. Catal. B:Environ. 90 (3-4) (2009) 451-457
[29] R.A. Campbell, S.R.W. Parker, J.P.R. Day, C.D. Bain, External reflection FTIR spectroscopy of the cationic surfactant hexadecyltrimethylammonium bromide (CTAB) on an overflowing cylinder, Langmuir 20 (20) (2004) 8740-8753
[30] X.Y. Zhang, D. Zhang, Z. Sun, L.F. Xue, X.H. Wang, Z.J. Jiang, Highly efficient preparation of HMF from cellulose using temperature-responsive heteropolyacid catalysts in cascade reaction, Appl. Catal. B:Environ. 196 (2016) 50-56
[31] T. Sang, C.J. Wallis, G. Hill, G.J.P. Britovsek, Polyethylene terephthalate degradation under natural and accelerated weathering conditions, Eur. Polym. J. 136 (2020) 109873

Towards recycling purpose: Converting PET plastic waste back to terephthalic acid using pH-responsive phase transfer catalyst

Towards recycling purpose: Converting PET plastic waste back to terephthalic acid using pH-responsive phase transfer catalyst

PDF (PC)

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 6

Recommended Articles

Metrics

Comments

[1]	Yanlin He, Yuan Xu, Zhiqiang Geng, Qunxiong Zhu . Soft sensor of chemical processes with large numbers of input parameters using auto-associative hierarchical neural network [J]. Chin.J.Chem.Eng., 2015, 23(1): 138-145.
[2]	LI Chengfei. Dynamic Simulation and Analysis of Industrial Purified Terephthalic Acid Solvent Dehydration Process [J]. , 2011, 19(1): 89-96.
[3]	TIAN Wenyu, ZENG Zuoxiang, XUE Weilan, LI Yingbin, ZHANG Tianyu. Kinetics of the Mono-esterification Between Terephthalic Acid and 1,4-Butanediol [J]. , 2010, 18(3): 391-396.
[4]	XU Yuan, ZHU Qunxiong. Research and Implementation of Decreasing the Acetic Acid Consumption in Purified Terephthalic Acid Solvent System [J]. , 2008, 16(4): 650-655.
[5]	MU Shengjing, SU Hongye, GU yong, CHU Jian. Multi-objective Optimization of Industrial Purified Terephthalic Acid Oxidation Process [J]. , 2003, 11(5): 536-541.
[6]	MA Peisheng, CHEN Mingming. Solid-Liquid Equilibrium of Terephthalic Acid in Several Solvents [J]. , 2003, 11(3): 334-337.