Chemical recycling of polymer contaminated poly(ethylene terephthalate) by neutral hydrolysis

Abstract

Plastic recycling is gaining traction to reduce the demand for fossil resources for plastic production. Poly(ethylene terephthalate) (PET), mainly used in the packaging and textile sectors, is often isolated in the sinking fraction during the density-based separation of mixed plastic waste streams. The heterogeneity of the sinking fraction makes direct mechanical recycling of PET impossible. Therefore, neutral hydrolysis of PET was investigated in the presence of other polymer contaminants to study their impact on the neutral hydrolysis of PET. PA6, PC, POM, and PVC were found to decompose during hydrolysis, whereas ABS, PMMA and a mixture of PE, PP and PS was chemically inert during the hydrolysis treatment. The subsequent BHET synthesis with excess ethylene glycol was performed directly on a mix of the polymer contaminated hydrolysis products or a hydrolyzed post-consumer plastic waste fraction. BHET was successfully formed in the plethora of decomposition products in the synthesis, and a subsequent recrystallization recovered the BHET in high purity with only water being used as solvent. This demonstrated a robust method to handle PET fractions in mixed plastic waste that can be applied without purification prior to BHET synthesis – enabling chemical recycling of PET.Abbreviations: ABS, Poly(acetonitrile-butadiene-styrene); ATR-FTIR, Attenuated Total Reflectance Fourier Transformed Infrared Spectroscopy; BC, Bis(2-Hydroxyethyl) terephthalate crystals; BHET, Bis(2-Hydroxyethyl) terephthalate; DMSO, Deuterated dimethyl sulfoxide; DSC, Differential Scanning Calorimetry; EG, Ethylene glycol; 1H NMR, Proton Nuclear Magnetic Resonance; Hm, Melting enthalpy; Oligo, Oligomers; PA6, Polyamide 6; PC, Polycarbonate; PE, Polyethylene; PET, Poly(ethylene terephthalate); PMMA, Poly(methyl methacrylate); POM, Polyoxymethylene; PP, Polypropylene; PS, Polystyrene; P, Purity; PVC, Poly(vinyl chloride); rpm, Revolutions per minute; SPHP, Solid Phase Hydrolysis Product; Ti(IV)OBu, Titanium(IV) butoxide; Tm, Melting temperature; TPA, Terephthalic acid; Wt, Weight; Y, Solid Phase Hydrolysis Product yield; Yt, Bis(2-Hydroxyethyl) terephthalate yield; ν, IR stretching mode; δ, IR bending mode; ω, IR wagging mode.