Isolation, Characterization and Structural Elucidation of Polybutylene Terephthalate Cyclic Oligomers and Purity Assessment using a 1H qNMR Method

Abstract

The use of polybutylene terephthalate (PBT) as a food contact material is increasing over the last years. Typical contaminations in the final PBT product include its cyclic oligomers, which are allowed as additives in food contact plastics according to Regulation (EU) No. 10/2011.Their investigation is currently limited by the lack of analytical standards and physical-chemical information. Therefore, four PBT cyclic oligomers have been isolated and purified from a PBT raw material with an automated preparative HPLC-DAD system. Comprehensive characterization of the compounds was performed using Ultra-High Performance Liquid Chromatography (UHPLC) with high resolution time-of-flight mass spectrometry, Fourier-Transform Infrared spectroscopy (FTIR), Differential Scanning Calorimetry (DSC) and Nuclear Magnetic Resonance (NMR) spectroscopy. The purity of each oligomer was assessed using a 1H qNMR method and ranged from 96.1% to 97.0% for PBT tetramer and trimer respectively. The availability of pure and well characterized PBT cyclic oligomer standards will facilitate future studies of release from plastic food packaging materials.

Keywords

• cyclic oligomers of polybutylene terephthalate (PBT)
• preparative HPLC (p-HPLC)
• High Resolution Mass Spectrometry (HR-MS)
• Nuclear Magnetic Resonance (NMR)
• qNMR purity assessment