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Title: Solubilization and Upgrading of High Polyethylene Terephthalate Loadings in a Low-Costing Bifunctional Ionic Liquid

Journal Article · · ChemSusChem
ORCiD logo [1];  [1];  [2];  [3];  [2];  [4]; ORCiD logo [5];  [4];  [1]
  1. Deconstruction Division, Joint BioEnergy Institute, 5885 Hollis Street Emeryville 94608 CA USA; Biological and Engineering Sciences Center, Sandia National Laboratories, 7011 East Avenue, Livermore 94551 CA USA
  2. Environmental Molecular Sciences Laboratory, Pacific Northwest National Laboratory, 902 Battelle Boulevard Richland 99352 WA USA
  3. Advanced Light Source Scientific Support Group, Lawrence Berkeley National Laboratory, 1 Cyclotron Road Berkeley 94720 CA USA
  4. Deconstruction Division, Joint BioEnergy Institute, 5885 Hollis Street Emeryville 94608 CA USA; Biological Systems and Engineering Division, Lawrence Berkeley National Laboratory, 1 Cyclotron Road Berkeley 94720 CA USA
  5. Environmental Molecular Sciences Laboratory, Pacific Northwest National Laboratory, 902 Battelle Boulevard Richland 99352 WA USA; Biological Sciences Division, Pacific Northwest National Laboratory, 902 Battelle Boulevard Richland 99352 WA USA

Polyethylene terephthalate (PET) is of significant commercial importance, but is difficult to recycle. Chemical inertness and resistance to biodegradation make the recycling of PET challenging and most solvents for PET are highly toxic. In this work, we demonstrate for the first time that a low cost (~$1.2/kg) and biocompatible ionic liquid (IL), cholinium phosphate ([Ch]3[PO4]) can play bifunctional roles in PET solubilization and glycolytic degradation. High loading of PET (10 wt%) is readily dissolved in [Ch]3[PO4] at relatively low temperatures (120 °C, 1h) and even in water-rich conditions. Tandem in situ confocal microscopy and Fourier Transform Infrared (FTIR) spectroscopy studies give detailed information on the solubilization mechanism in terms of morphological and chemical changes that occur. In depth analysis of PET-IL solution reveals that the high PET solubilization in [Ch]3[PO4] can be ascribed to significant PET depolymerization. Acid precipitation yields terephthalic acid as the dominant depolymerized monomer with a theoretical yield of ~95%. Further exploration shows that in the presence of ethylene glycol, [Ch]3[PO4] catalyzed glycolysis of PET can efficiently occur with ~100% PET conversion and ~60.6% bis(2-hydroxyethyl)terephthalate (BHET) yield under metal free conditions. The IL can be reused at least three times without an apparent decrease in activity. NMR analysis reveals that strong hydrogen bond interactions between EG and the IL play an important role for EG activation and promotion of the glycolysis reaction. This study opens up avenues for exploring environmentally benign and efficient technology of ILs for solubilizing and recycling postconsumer polyester plastics.

Research Organization:
Pacific Northwest National Lab. (PNNL), Richland, WA (United States). Environmental Molecular Sciences Lab. (EMSL)
Sponsoring Organization:
USDOE
DOE Contract Number:
AC05-76RL01830
OSTI ID:
1439020
Report Number(s):
PNNL-SA-128561; 48827; KP1704020
Journal Information:
ChemSusChem, Vol. 11, Issue 4; ISSN 1864-5631
Publisher:
ChemPubSoc Europe
Country of Publication:
United States
Language:
English

References (44)

Production, use, and fate of all plastics ever made journal July 2017
Effect of the Addition of Modified Nanoclays on the Surface Properties of the Resultant Polyethylene Terephthalate/Clay Nanocomposites journal June 2010
Deep eutectic solvents: Synthesis, application, and focus on lipase-catalyzed reactions journal March 2013
Ionic-liquid materials for the electrochemical challenges of the future journal July 2009
Poly(ionic liquid)/Ionic Liquid Ion-Gels with High “Free” Ionic Liquid Content: Platform Membrane Materials for CO 2 /Light Gas Separations journal April 2016
Glycolysis of poly(ethylene terephthalate) catalyzed by ionic liquids journal May 2009
Deep Eutectic Solvents (DESs) and Their Applications journal October 2014
Fe-containing magnetic ionic liquid as an effective catalyst for the glycolysis of poly(ethylene terephthalate) journal March 2010
Inexpensive ionic liquids: [HSO 4 ] -based solvent production at bulk scale journal January 2014
The use of an n-type macromolecular additive as a simple yet effective tool for improving and stabilizing the performance of organic solar cells journal January 2016
Glycolysis of poly(ethylene terephthalate) (PET) using basic ionic liquids as catalysts journal April 2011
Understanding the hydrogen bonds in ionic liquids and their roles in properties and reactions journal January 2016
Ionic liquid-based green processes for energy production journal January 2014
Poisoning Effects of Water and Dyes on the [Bmim][BF4] Catalysis of Poly(Ethylene Terephthalate) (PET) Depolymerization under Supercritical Ethanol journal January 2017
Surface structure and properties of poly-(ethylene terephthalate) hydrolyzed by alkali and cutinase journal September 2010
Pet Waste Management by Chemical Recycling: A Review journal September 2008
Understanding the role of water during ionic liquid pretreatment of lignocellulose: co-solvent or anti-solvent? journal January 2014
Physical ageing of polyethylene terephthalate under natural sunlight: correlation study between crystallinity and mechanical properties journal December 2015
Deep eutectic solvents as highly active catalysts for the fast and mild glycolysis of poly(ethylene terephthalate)(PET) journal January 2015
Advances and challenges for flexible energy storage and conversion devices and systems journal January 2014
Reactive Compatibilization of Poly(ethylene terephthalate) and High-Density Polyethylene Using Amino-Telechelic Polyethylene journal November 2016
Nanostructured positive electrode materials for post-lithium ion batteries journal January 2016
Effective catalysis of poly(ethylene terephthalate) (PET) degradation by metallic acetate ionic liquids journal February 2012
CO 2 enabled process integration for the production of cellulosic ethanol using bionic liquids journal January 2016
Biological Activity of Ionic Liquids and Their Application in Pharmaceutics and Medicine journal January 2017
One-Step Ionic-Liquid-Assisted Electrochemical Synthesis of Ionic-Liquid-Functionalized Graphene Sheets Directly from Graphite: Ionic-Liquid-Assisted Electrochemical Synthesis of Graphene journal May 2008
Influence of cholinium-based ionic liquids on the structural stability and activity of α-chymotrypsin journal January 2017
Surface charge self-recovering electret film for wearable energy conversion in a harsh environment journal January 2016
One-pot integrated biofuel production using low-cost biocompatible protic ionic liquids journal January 2017
Degradation of poly(ethylene terephthalate) using ionic liquids journal January 2009
Theoretical and experimental studies of water interaction in acetate based ionic liquids journal January 2012
Urea as an efficient and reusable catalyst for the glycolysis of poly(ethylene terephthalate) wastes and the role of hydrogen bond in this process journal January 2012
Greener routes for recycling of polyethylene terephthalate journal March 2016
Application of Ionic Liquids to Energy Storage and Conversion Materials and Devices journal January 2017
Kinetics of catalytic glycolysis of PET wastes with sodium carbonate journal March 2011
Biodegradation of polyesters containing aromatic constituents journal March 2001
Synthesis of three advanced biofuels from ionic liquid-pretreated switchgrass using engineered Escherichia coli journal November 2011
Lithium-ion battery structure that self-heats at low temperatures journal January 2016
A bacterium that degrades and assimilates poly(ethylene terephthalate) journal March 2016
Recycling of poly(ethylene terephthalate) – A review focusing on chemical methods journal January 2016
Synthesis and hydrophobic properties of F & Si containing poly(ethylene terephthalate) journal January 2016
Fe 3 O 4 -boosted MWCNT as an efficient sustainable catalyst for PET glycolysis journal January 2016
Effect of anion structures on cholinium ionic liquids pretreatment of rice straw and the subsequent enzymatic hydrolysis: Anion Effect of Cholinium IL Pretreatment journal September 2014
Electron beam induced modifications in flexible biaxially oriented polyethylene terephthalate sheets: Improved mechanical and electrical properties journal March 2017