Identification and Separation of Transformed Products of tert-Butylhydroquinone Added in Different Oils and Fats during Storage

Abstract

The transformation of tert-butylhydroquinone (TBHQ) added in lard, soybean and palm oil was investigated during storage. The results showed that when the storage time was extended, the sum of the remaining amount of TBHQ and the production of 2-tert-butyl-1,4-benzoquinone (TBBQ) in oil samples was less than the initial amount of TBHQ added. The same chromatographic peaks except for TBHQ and TBBQ were found in the gas chromatograms of the methanol extracts from different oil samples. The unknown chromatographic peaks were isolated and purified by preparative liquid chromatography (Prep-LC), and their structures were identified and characterized by ultra-high performance liquid chromatography-quadrupole-time of flight-mass spectrometry (UPLC-Q-TOF-MS), nuclear magnetic resonance (NMR), ultraviolet (UV) spectroscopy, and Fourier transform infrared (FTIR) spectroscopy. These results showed that the conversion products of added TBHQ were the same in different oils and fats, including TBBQ and 2-methylallyl-hydroquinone (MAHQ).

Keywords

• tert-butylhydroquinone; tert-butylquinone; 2-methylallyl-hydroquinone; separation and purification; structural identification