Catalytic Degradation of Polyethylene Terephthalate Using a Phase‐Transitional Zirconium‐Based Metal–Organic Framework

Wu, Yufang; Wang, Xingjie; Kirlikovali, Kent O.; Gong, Xinyi; Atilgan, Ahmet; Ma, Kaikai; Schweitzer, Neil M.; Gianneschi, Nathan C.; Li, Zhong; Zhang, Xuan; Farha, Omar K.

doi:10.1002/ange.202117528

Title: Catalytic Degradation of Polyethylene Terephthalate Using a Phase‐Transitional Zirconium‐Based Metal–Organic Framework

Journal Article · 19 April 2022 · Angewandte Chemie

DOI: https://doi.org/10.1002/ange.202117528 · OSTI ID:1864097

Wu, Yufang ^[1]; Wang, Xingjie ^[2]; Kirlikovali, Kent O. ^[2]; Gong, Xinyi ^[2]; Atilgan, Ahmet ^[2]; Ma, Kaikai ^[2]; Schweitzer, Neil M. ^[3]; Gianneschi, Nathan C. ^[4]; Li, Zhong ^[5]; Zhang, Xuan ^[2];

^[6]

School of Chemistry and Chemical Engineering South China University of Technology Guangzhou Guangdong 510640 P. R. China, Department of Chemistry and International Institute for Nanotechnology Northwestern University 2145 Sheridan Road Evanston IL 60208 USA
Department of Chemistry and International Institute for Nanotechnology Northwestern University 2145 Sheridan Road Evanston IL 60208 USA
Department of Chemical and Biological Engineering Northwestern University 2145 Sheridan Road Evanston IL 60208 USA
Department of Chemistry and International Institute for Nanotechnology Northwestern University 2145 Sheridan Road Evanston IL 60208 USA, Department of Biomedical Engineering, Materials Science &, Engineering, Pharmacology Simpson-Querrey Institute Chemistry of Life Processes Institute Lurie Cancer Center Northwestern University 2145 Sheridan Road Evanston IL 60208 USA
School of Chemistry and Chemical Engineering South China University of Technology Guangzhou Guangdong 510640 P. R. China
Department of Chemistry and International Institute for Nanotechnology Northwestern University 2145 Sheridan Road Evanston IL 60208 USA, Department of Chemical and Biological Engineering Northwestern University 2145 Sheridan Road Evanston IL 60208 USA

Abstract Polyethylene terephthalate (PET) is utilized as one of the most popular consumer plastics worldwide, but difficulties associated with recycling PET have generated a severe environmental crisis with most PET ending its lifecycle in landfills. We report that zirconium‐based metal–organic framework (Zr‐MOF) UiO‐66 deconstructs waste PET into the building blocks terephthalic acid (TA) and mono‐methyl terephthalate (MMT) within 24 hours at 260 °C (total yield of 98 % under 1 atm H ₂ and 81 % under 1 atm Ar). Extensive structural characterization studies reveal that during the degradation process, UiO‐66 undergoes an intriguing transformation into MIL‐140A, which is another Zr‐MOF that shows good catalytic activity toward PET degradation under similar reaction conditions. These results illustrate the diversity of applications for Zr‐MOFs and establish MOFs as a new class of polymer degradation catalysts with the potential to address long‐standing challenges associated with plastic waste.

View Accepted Manuscript (Publisher)

Cite

Export

Save

Sponsoring Organization:: USDOE

Grant/Contract Number:: SC0001329; SC0012702

OSTI ID:: 1864097

Journal Information:: Angewandte Chemie, Journal Name: Angewandte Chemie Journal Issue: 24 Vol. 134; ISSN 0044-8249

Publisher:: Wiley Blackwell (John Wiley & Sons)Copyright Statement

Country of Publication:: Germany

Language:: English

References (60)

Metal-Organic Frameworks as Platforms for Catalytic Applications Jiao, Long; Wang, Yang; Jiang, Hai-Long Advanced Materials, Vol. 30, Issue 37 https://doi.org/10.1002/adma.201703663	journal	November 2017
A Series of Isoreticular, Highly Stable, Porous Zirconium Oxide Based Metal-Organic Frameworks Guillerm, V.; Ragon, F.; Dan-Hardi, M. Angewandte Chemie, Vol. 124, Issue 37 https://doi.org/10.1002/ange.201204806	journal	August 2012
Die nächste Generation des Recyclings – neues Leben für Kunststoffmüll Vollmer, Ina; Jenks, Michael J. F.; Roelands, Mark C. P. Angewandte Chemie, Vol. 132, Issue 36 https://doi.org/10.1002/ange.201915651	journal	June 2020
Polyethylene Terephthalate Deconstruction Catalyzed by a Carbon‐Supported Single‐Site Molybdenum‐Dioxo Complex Kratish, Yosi; Li, Jiaqi; Liu, Shanfu Angewandte Chemie, Vol. 132, Issue 45 https://doi.org/10.1002/ange.202007423	journal	September 2020
Selective Chemical Upcycling of Mixed Plastics Guided by a Thermally Stable Organocatalyst Jehanno, Coralie; Demarteau, Jeremy; Mantione, Daniele Angewandte Chemie, Vol. 133, Issue 12 https://doi.org/10.1002/ange.202014860	journal	February 2021
A Series of Isoreticular, Highly Stable, Porous Zirconium Oxide Based Metal-Organic Frameworks Guillerm, V.; Ragon, F.; Dan-Hardi, M. Angewandte Chemie International Edition, Vol. 51, Issue 37 https://doi.org/10.1002/anie.201204806	journal	August 2012
Beyond Mechanical Recycling: Giving New Life to Plastic Waste Vollmer, Ina; Jenks, Michael J. F.; Roelands, Mark C. P. Angewandte Chemie International Edition, Vol. 59, Issue 36 https://doi.org/10.1002/anie.201915651	journal	June 2020
Polyethylene Terephthalate Deconstruction Catalyzed by a Carbon‐Supported Single‐Site Molybdenum‐Dioxo Complex Kratish, Yosi; Li, Jiaqi; Liu, Shanfu Angewandte Chemie International Edition, Vol. 59, Issue 45 https://doi.org/10.1002/anie.202007423	journal	September 2020
Selective Chemical Upcycling of Mixed Plastics Guided by a Thermally Stable Organocatalyst Jehanno, Coralie; Demarteau, Jeremy; Mantione, Daniele Angewandte Chemie International Edition, Vol. 60, Issue 12 https://doi.org/10.1002/anie.202014860	journal	February 2021
A Low‐Temperature Approach for the Phase‐Pure Synthesis of MIL‐140 Structured Metal–Organic Frameworks Schulz, Marcel; Marquardt, Nele; Schäfer, Malte Chemistry – A European Journal, Vol. 25, Issue 59 https://doi.org/10.1002/chem.201902981	journal	September 2019
A review on thermal decomposition and combustion of thermoplastic polyesters Levchik, Sergei V.; Weil, Edward D. Polymers for Advanced Technologies, Vol. 15, Issue 12 https://doi.org/10.1002/pat.526	journal	December 2004
Advances and approaches for chemical recycling of plastic waste Thiounn, Timmy; Smith, Rhett C. Journal of Polymer Science, Vol. 58, Issue 10 https://doi.org/10.1002/pol.20190261	journal	April 2020
Primary thermal degradation mechanisms of PET and PBT Montaudo, Giorgio; Puglisi, Concetto; Samperi, Filippo Polymer Degradation and Stability, Vol. 42, Issue 1 https://doi.org/10.1016/0141-3910(93)90021-A	journal	January 1993
Variations in capping the Zr6O4(OH)4 cluster core: X-ray structure analyses of [Zr6(OH)4O4(OOC–CHCH2)10]2(μ-OOC–CHCH2)4 and Zr6(OH)4O4(OOCR)12(PrOH) (R=Ph, CMe=CH2) Kickelbick, Guido; Wiede, Petra; Schubert, Ulrich Inorganica Chimica Acta, Vol. 284, Issue 1 https://doi.org/10.1016/S0020-1693(98)00251-5	journal	January 1999
Thermal degradation of poly(ethylene terephthalate) at the processing temperature Samperi, Filippo; Puglisi, Concetto; Alicata, Rossana Polymer Degradation and Stability, Vol. 83, Issue 1 https://doi.org/10.1016/S0141-3910(03)00166-6	journal	January 2004
Highly efficient catalytic transfer hydrogenation of biomass-derived furfural to furfuryl alcohol using UiO-66 without metal catalysts Qiu, Mo; Guo, Tianmeng; Xi, Ran Applied Catalysis A: General, Vol. 602 https://doi.org/10.1016/j.apcata.2020.117719	journal	July 2020
Exchange reactions in metal-organic frameworks: New advances Xu, Ming-Ming; Chen, Qiang; Xie, Lin-Hua Coordination Chemistry Reviews, Vol. 421 https://doi.org/10.1016/j.ccr.2020.213421	journal	October 2020
Thermal degradation kinetics and decomposition mechanism of polyesters based on 2,5-furandicarboxylic acid and low molecular weight aliphatic diols Tsanaktsis, Vasilios; Vouvoudi, Evangelia; Papageorgiou, George Z. Journal of Analytical and Applied Pyrolysis, Vol. 112 https://doi.org/10.1016/j.jaap.2014.12.016	journal	March 2015
Nature of active sites on UiO-66 and beneficial influence of water in the catalysis of Fischer esterification Caratelli, Chiara; Hajek, Julianna; Cirujano, Francisco G. Journal of Catalysis, Vol. 352 https://doi.org/10.1016/j.jcat.2017.06.014	journal	August 2017
Pyrolysis of poly(ethylene terephthalate) in a fluidised bed plant Yoshioka, Toshiaki; Grause, Guido; Eger, Christian Polymer Degradation and Stability, Vol. 86, Issue 3 https://doi.org/10.1016/j.polymdegradstab.2004.06.001	journal	December 2004
Thermal stability and flame-retardancy mechanism of poly(ethylene terephthalate)/boehmite nanocomposites Zhang, Jianjun; Ji, Quan; Zhang, Ping Polymer Degradation and Stability, Vol. 95, Issue 7 https://doi.org/10.1016/j.polymdegradstab.2010.04.001	journal	July 2010
Py-GC/MS analyses of poly(ethylene terephthalate) film without and with the presence of tetramethylammonium acetate reagent. Comparative study Dziwiński, Euzebiusz Jan; Iłowska, Jolanta; Gniady, Jan Polymer Testing, Vol. 65 https://doi.org/10.1016/j.polymertesting.2017.11.009	journal	February 2018
Enzyme discovery and engineering for sustainable plastic recycling Zhu, Baotong; Wang, Dong; Wei, Na Trends in Biotechnology, Vol. 40, Issue 1 https://doi.org/10.1016/j.tibtech.2021.02.008	journal	January 2022
Upcycling and catalytic degradation of plastic wastes Hou, Qidong; Zhen, Meinan; Qian, Hengli Cell Reports Physical Science, Vol. 2, Issue 8 https://doi.org/10.1016/j.xcrp.2021.100514	journal	August 2021
Brønsted Acidity in Metal–Organic Frameworks Jiang, Juncong; Yaghi, Omar M. Chemical Reviews, Vol. 115, Issue 14 https://doi.org/10.1021/acs.chemrev.5b00221	journal	June 2015
Role of Modulators in Controlling the Colloidal Stability and Polydispersity of the UiO-66 Metal–Organic Framework Morris, William; Wang, Shunzhi; Cho, David ACS Applied Materials & Interfaces, Vol. 9, Issue 39 https://doi.org/10.1021/acsami.7b01040	journal	April 2017
p K _a -Directed Incorporation of Phosphonates into MOF-808 via Ligand Exchange: Stability and Adsorption Properties for Uranium Zhang, Wen; Bu, An; Ji, Qingyuan ACS Applied Materials & Interfaces, Vol. 11, Issue 37 https://doi.org/10.1021/acsami.9b10920	journal	August 2019
Zirconium-Based Metal–Organic Frameworks for the Catalytic Hydrolysis of Organophosphorus Nerve Agents Kirlikovali, Kent O.; Chen, Zhijie; Islamoglu, Timur ACS Applied Materials & Interfaces, Vol. 12, Issue 13 https://doi.org/10.1021/acsami.9b20154	journal	January 2020
Zr ₆ O ₈ Node-Catalyzed Butene Hydrogenation and Isomerization in the Metal–Organic Framework NU-1000 Hicks, Kenton E.; Rosen, Andrew S.; Syed, Zoha H. ACS Catalysis, Vol. 10, Issue 24 https://doi.org/10.1021/acscatal.0c03579	journal	December 2020
One-Pot Chemo-bioprocess of PET Depolymerization and Recycling Enabled by a Biocompatible Catalyst, Betaine Kim, Dong Hyun; Han, Dong Oh; In Shim, Kyu ACS Catalysis, Vol. 11, Issue 7 https://doi.org/10.1021/acscatal.0c04014	journal	March 2021
Catalysis by Metal Organic Frameworks: Perspective and Suggestions for Future Research Yang, Dong; Gates, Bruce C. ACS Catalysis, Vol. 9, Issue 3 https://doi.org/10.1021/acscatal.8b04515	journal	January 2019
Biodegradation of PET: Current Status and Application Aspects Taniguchi, Ikuo; Yoshida, Shosuke; Hiraga, Kazumi ACS Catalysis, Vol. 9, Issue 5 https://doi.org/10.1021/acscatal.8b05171	journal	April 2019
Rational Protein Engineering of Thermo-Stable PETase from Ideonella sakaiensis for Highly Efficient PET Degradation Son, Hyeoncheol Francis; Cho, In Jin; Joo, Seongjoon ACS Catalysis, Vol. 9, Issue 4 https://doi.org/10.1021/acscatal.9b00568	journal	March 2019
Decomposition of the PET Film by MHETase Using Exo-PETase Function Sagong, Hye-Young; Seo, Hogyun; Kim, Taeho ACS Catalysis, Vol. 10, Issue 8 https://doi.org/10.1021/acscatal.9b05604	journal	February 2020
Benign by Design: Green and Scalable Synthesis of Zirconium UiO-Metal–Organic Frameworks by Water-Assisted Mechanochemistry Karadeniz, Bahar; Howarth, Ashlee J.; Stolar, Tomislav ACS Sustainable Chemistry & Engineering, Vol. 6, Issue 11 https://doi.org/10.1021/acssuschemeng.8b04458	journal	October 2018
Introduction to Metal–Organic Frameworks Zhou, Hong-Cai; Long, Jeffrey R.; Yaghi, Omar M. Chemical Reviews, Vol. 112, Issue 2, p. 673-674 https://doi.org/10.1021/cr300014x	journal	September 2011
A New Zirconium Inorganic Building Brick Forming Metal Organic Frameworks with Exceptional Stability Cavka, Jasmina Hafizovic; Jakobsen, Søren; Olsbye, Unni Journal of the American Chemical Society, Vol. 130, Issue 42, p. 13850-13851 https://doi.org/10.1021/ja8057953	journal	October 2008
Insights into the Structure and Dynamics of Metal–Organic Frameworks via Transmission Electron Microscopy Gong, Xinyi; Gnanasekaran, Karthikeyan; Chen, Zhijie Journal of the American Chemical Society, Vol. 142, Issue 41 https://doi.org/10.1021/jacs.0c08773	journal	September 2020
Chemical, thermal and mechanical stabilities of metal–organic frameworks Howarth, Ashlee J.; Liu, Yangyang; Li, Peng Nature Reviews Materials, Vol. 1, Issue 3 https://doi.org/10.1038/natrevmats.2015.18	journal	February 2016
Identification of the strong Brønsted acid site in a metal–organic framework solid acid catalyst Trickett, Christopher A.; Osborn Popp, Thomas M.; Su, Ji Nature Chemistry, Vol. 11, Issue 2 https://doi.org/10.1038/s41557-018-0171-z	journal	November 2018
Chemical recycling of waste plastics for new materials production Rahimi, AliReza; García, Jeannette M. Nature Reviews Chemistry, Vol. 1, Issue 6 https://doi.org/10.1038/s41570-017-0046	journal	June 2017
An engineered PET depolymerase to break down and recycle plastic bottles Tournier, V.; Topham, C. M.; Gilles, A. Nature, Vol. 580, Issue 7802 https://doi.org/10.1038/s41586-020-2149-4	journal	April 2020
Possibilities and limitations of biotechnological plastic degradation and recycling Wei, Ren; Tiso, Till; Bertling, Jürgen Nature Catalysis, Vol. 3, Issue 11 https://doi.org/10.1038/s41929-020-00521-w	journal	October 2020
Chemical and biological catalysis for plastics recycling and upcycling Ellis, Lucas D.; Rorrer, Nicholas A.; Sullivan, Kevin P. Nature Catalysis, Vol. 4, Issue 7 https://doi.org/10.1038/s41929-021-00648-4	journal	July 2021
Metal–Organic Frameworks (MOFs) Zhou, Hong-Cai “Joe”; Kitagawa, Susumu Chem. Soc. Rev., Vol. 43, Issue 16 https://doi.org/10.1039/C4CS90059F	journal	January 2014
Zr-based metal–organic frameworks: design, synthesis, structure, and applications Bai, Yan; Dou, Yibo; Xie, Lin-Hua Chemical Society Reviews, Vol. 45, Issue 8 https://doi.org/10.1039/C5CS00837A	journal	January 2016
Improving MOF stability: approaches and applications Ding, Meili; Cai, Xuechao; Jiang, Hai-Long Chemical Science, Vol. 10, Issue 44 https://doi.org/10.1039/C9SC03916C	journal	January 2019
Engineering zirconium-based UiO-66 for effective chemical conversion of d -xylose to lactic acid in aqueous condition Ponchai, Panyapat; Adpakpang, Kanyaporn; Thongratkaew, Sutarat Chemical Communications, Vol. 56, Issue 58 https://doi.org/10.1039/D0CC03424J	journal	January 2020
Towards closed-loop recycling of multilayer and coloured PET plastic waste by alkaline hydrolysis Ügdüler, Sibel; Van Geem, Kevin M.; Denolf, Ruben Green Chemistry, Vol. 22, Issue 16 https://doi.org/10.1039/D0GC00894J	journal	January 2020
Low-energy catalytic methanolysis of poly(ethyleneterephthalate) Pham, Duong Dinh; Cho, Joungmo Green Chemistry, Vol. 23, Issue 1 https://doi.org/10.1039/D0GC03536J	journal	January 2021
Chemolytic depolymerisation of PET: a review Barnard, Elaine; Rubio Arias, Jose Jonathan; Thielemans, Wim Green Chemistry, Vol. 23, Issue 11 https://doi.org/10.1039/D1GC00887K	journal	January 2021
Instantaneous hydrolysis of PET bottles: an efficient pathway for the chemical recycling of condensation polymers Rubio Arias, Jose Jonathan; Thielemans, Wim Green Chemistry, Vol. 23, Issue 24 https://doi.org/10.1039/D1GC02896K	journal	January 2021
Cobalt–molybdenum synergistic catalysis for the hydrogenolysis of terephthalate-based polyesters Wu, Pengyu; Lu, Guoping; Cai, Chun Green Chemistry, Vol. 23, Issue 21 https://doi.org/10.1039/D1GC02929K	journal	January 2021
Controlled hydrogenative depolymerization of polyesters and polycarbonates catalyzed by ruthenium(ii) PNN pincer complexes Krall, Eric M.; Klein, Tyler W.; Andersen, Ryan J. Chemical Communications, Vol. 50, Issue 38 https://doi.org/10.1039/c4cc00541d	journal	January 2014
Enzymatic depolymerization of highly crystalline polyethylene terephthalate enabled in moist-solid reaction mixtures Kaabel, Sandra; Therien, J. P. Daniel; Deschênes, Catherine E. Proceedings of the National Academy of Sciences, Vol. 118, Issue 29 https://doi.org/10.1073/pnas.2026452118	journal	July 2021
Production, use, and fate of all plastics ever made Geyer, Roland; Jambeck, Jenna R.; Law, Kara Lavender Science Advances, Vol. 3, Issue 7 https://doi.org/10.1126/sciadv.1700782	journal	July 2017
Molecular catalyst systems as key enablers for tailored polyesters and polycarbonate recycling concepts Westhues, Stefan; Idel, Jasmine; Klankermayer, Jürgen Science Advances, Vol. 4, Issue 8 https://doi.org/10.1126/sciadv.aat9669	journal	August 2018
The Chemistry and Applications of Metal-Organic Frameworks Furukawa, H.; Cordova, K. E.; O'Keeffe, M. Science, Vol. 341, Issue 6149, p. 1230444-1230444 https://doi.org/10.1126/science.1230444	journal	August 2013
A bacterium that degrades and assimilates poly(ethylene terephthalate) Yoshida, Shosuke; Hiraga, Kazumi; Takehana, Toshihiko Science, Vol. 351, Issue 6278 https://doi.org/10.1126/science.aad6359	journal	March 2016
Balancing volumetric and gravimetric uptake in highly porous materials for clean energy Chen, Zhijie; Li, Penghao; Anderson, Ryther Science, Vol. 368, Issue 6488 https://doi.org/10.1126/science.aaz8881	journal	April 2020

Similar Records

Catalytic Degradation of Polyethylene Terephthalate Using a Phase-Transitional Zirconium-Based Metal–Organic Framework

Journal Article · 2022 · Angewandte Chemie (International Edition) · OSTI ID:1976279

Wu, Yufang; Wang, Xingjie; Kirlikovali, Kent O.; +8 more

Polyethylene Terephthalate Deconstruction Catalyzed by a Carbon‐Supported Single‐Site Molybdenum‐Dioxo Complex

Journal Article · 2020 · Angewandte Chemie · OSTI ID:1668096

Kratish, Yosi; Li, Jiaqi; Liu, Shanfu; +2 more

Polyethylene Terephthalate Deconstruction Catalyzed by a Carbon–Supported Single–Site Molybdenum–Dioxo Complex

Journal Article · 2020 · Angewandte Chemie (International Edition) · OSTI ID:2480919

Kratish, Yosi; Li, Jiaqi; Liu, Shanfu; +2 more

Title: Catalytic Degradation of Polyethylene Terephthalate Using a Phase‐Transitional Zirconium‐Based Metal–Organic Framework

Citation Formats

References (60)

Similar Records

Related Subjects