DOE PAGES title logo U.S. Department of Energy
Office of Scientific and Technical Information

Title: Biobased chemical recycling: aminolysis of PET using renewable reagents and monomers to synthesize new semi-aromatic polyamides

Journal Article · · RSC Sustainability
DOI: https://doi.org/10.1039/D5SU00547G · OSTI ID:3023650

Chemical recycling of PET is a method of depolymerizing polymer chains to monomeric components enabling the synthesis of second-generation materials with virgin-like quality. Commercial chemical recycling techniques rely upon high pressure methanolysis to create precursors capable of synthesizing a second-generation PET resin. However, despite the circular approach of methanolysis, a product with a very short lifespan and similar value is created. The approach of the current study is to utilize aminolysis as an ambient pressure technique to create precursors for higher value materials with longer lifespans to address the current crisis in plastic waste. Semi-aromatic polyamides (SAP) are desired in this circumstance because of their high melting point and heat resistance combined with good melt-processability similar to aliphatic polyamides. In this study SAPs were synthesized using precursors recovered from the aminolysis of PET employing biobased diamines and dicarboxylic acids. While aminolysis has been explored in previous studies, this work investigated the use of biobased components from castor oil: decamethylene diamine during recycling and sebacic acid during polymerization. Polymer synthesis resulted in the formation of SAPs similar to polyphthalamides (PPA) with novel structures given the aromatic portion from terephthalic acid (TPA) and aliphatic portion from the diamines and diacids. The synthesized materials exhibited excellent thermal stability with high glass transition temperatures. Novel polymers were created with varying aliphatic chain length to understand fundamental parameters needed to produce a valuable polymer from post-consumer waste.

Research Organization:
Pacific Northwest National Laboratory (PNNL), Richland, WA (United States)
Sponsoring Organization:
USDOE Office of Science (SC), Basic Energy Sciences (BES)
Grant/Contract Number:
AC05-76RL01830; SC0023389
OSTI ID:
3023650
Report Number(s):
PNNL-SA--218230
Journal Information:
RSC Sustainability, Journal Name: RSC Sustainability Journal Issue: 11 Vol. 3; ISSN 2753-8125
Publisher:
Royal Society of ChemistryCopyright Statement
Country of Publication:
United States
Language:
English

References (34)

Beyond Mechanical Recycling: Giving New Life to Plastic Waste journal June 2020
Synthesis of novel methacrylate‐based nanocomposites containing ZnO via the hydrothermal method and determination of thermal, optical, and biocidal properties journal August 2022
Advances and approaches for chemical recycling of plastic waste journal April 2020
Control of Spinning Sidebands in High Resolution NMR Spectroscopy journal April 1998
Synthesis of semiaromatic polyamides based on decanediamine journal April 2010
From Aminolysis Product of PET Waste to Novel Biodegradable Polyurethanes journal February 2011
Synthesis and Characterization of Bio-Based Amorphous Polyamide From Dimethyl furan-2,5-dicarboxylate journal August 2021
Aminolytic Depolymerization of Polyethylene Terephthalate Wastes Using Sn-Doped ZnO Nanoparticles journal April 2022
Synthesis of Biobased Furan Polyamides with Excellent Mechanical Properties: Effect of Diamine Chain Length journal January 2024
Synthesis of 2,5-furandicarboxylic acid-based heat-resistant polyamides under existing industrialization process journal May 2017
Structure-property insights of semi-aromatic polyamides based on renewable furanic monomer and aliphatic diamines journal September 2022
Mechanical properties of amorphous and semi-crystalline semi-aromatic polyamides journal April 2020
Manufacturing energy and greenhouse gas emissions associated with plastics consumption journal January 2021
Aminolysis of polyethylene terephthalate waste journal August 2006
Chemical recycling of poly(ethylene terephthalate) waste using ethanolamine. Sorting of the end products journal February 2010
Synthesis and thermal degradation mechanism of a semi-aromatic copolyamide from renewable sources journal September 2022
Polyurethane elastomers with amide chain extenders of uniform length journal February 2006
Insights and comparison of structure–bulk property relationships in low generation hydroxylated polyester dendrimer and hyperbranched polymer prepared from bis-MPA monomer journal September 2021
Priamine 1075 and catechol carbonate, a perfect match for ecofriendly production of a new renewable polyurea for sustainable flexible food packaging journal February 2023
Circular fashion: Properties of fabrics made from mechanically recycled poly-ethylene terephthalate (PET) bottles journal October 2020
Open-loop recycling of post-consumer PET to closed-loop chemically recyclable high-performance polyimines journal June 2023
Prospective life cycle assessment of poly (ethylene terephthalate) upcycling via chemoselective depolymerization journal November 2023
Current advancements in the bio-based production of polyamides journal December 2023
Poly(ester amide)s from Soybean Oil for Modulated Release and Bone Regeneration journal September 2016
Direct Synthesis of Thermally Stable Semiaromatic Polyamides by Bulk Polymerization Using Aromatic Diamines and Aliphatic Dicarboxylic Acids journal March 2022
Synthesis of High-Molecular-Weight All-Biobased Semiaromatic Furan Polyamide and Study on Its Polymerization Process journal October 2024
Recent Developments in the Chemical Recycling of Postconsumer Poly(ethylene terephthalate) Waste journal September 2014
Advanced chemical recycling of poly(ethylene terephthalate) through organocatalytic aminolysis journal January 2013
Synthesis and characterization of semiaromatic polyamides with dicyclohexane units journal January 2016
Enzymatic synthesis of 2,5-furandicarboxylic acid-based semi-aromatic polyamides: enzymatic polymerization kinetics, effect of diamine chain length and thermal properties journal January 2016
A roadmap towards green packaging: the current status and future outlook for polyesters in the packaging industry journal January 2017
The quest for high glass transition temperature bioplastics journal January 2018
Preparation and Properties of PA10T/PPO Blends Compatibilized with SEBS-g-MAH journal June 2024
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 journal April 2012