Differentiation of bisphenol F diglycidyl ether isomers and their derivatives by HPLC-MS and GC-MS—comment on the published data

Abstract

Positional isomers of bisphenol F diglycidyl ether (BFDGE) have been analyzed by high-pressure liquid chromatography-mass spectrometry and by gas chromatography-mass spectrometry (HPLC-MS, GC-MS). Positional isomers of BFDGE derivatives (BFDGEx2H2O, BFDGExH2OxHCl) have been analyzed by HPLC-MS. On the basis of the obtained fragmentation patterns, the elution order of the isomers has been unequivocally determined, in standard solutions and in the sample of liquid obtained after rinsing an empty mackerel fish can with acetonitrile. Under HPLC condition, para,para isomers are eluted first, then ortho,para isomers’ elution follows, and ortho,ortho isomers are eluted last. Under GC condition, the reverse elution order has been obtained. For the first time, two ortho,para isomers of BFDGExH2OxHCl have been detected and their elution order has been determined. The obtained results are of key importance for determination of the isomer distribution of BFDGE and its derivatives in food samples.

Ethoxylated Butoxyethanol-BADGE Adducts—New Potential Migrants from Epoxy Resin Can Coating Material

“…During an HPLC/ESI-MS analysis, BADGE and similar compounds are usually detected as [M + NH 4 ] + ions, even when no ammonium salt is added to the mobile phase [15,16,22]. In our experiment, the ethoxylated butoxyethanol-BADGE adducts were also detected as [M + NH 4 ] + .…”

Gas Phase Reactivity of Isomeric Hydroxylated Polychlorinated Biphenyls

“…For instance, Zhang et al 6 observed that the fragmentation spectra of positional isomers of epoxides produced from cis-and trans-hexenol show high overlap. Kasperkowiak et al 7 observed a high overlap of the fragmentation spectra of positional isomers of bisphenol F diglycidyl ethers, and Casas-Ferreira et al 8 have observed the same for positional isomers of amino acids. This arises as MS 2 spectra do not reveal the 3D-structural information on such isomeric compounds.…”

A guide towards safe, functional and renewable BPA alternatives by rational molecular design: structure–property and structure–toxicity relationships

“…3 This BFDGE often exists as a mixture of regioisomers, mix′-BPF•DGE, with o,p′-BPF•DGE as the dominant isomer. 92 Hence, the lower viscosity of a commercial BFDGE resin is conveyed by (i) the methylene bridge and/or (ii) the presence of ortho-regioisomers. 42 In this regard, Hernandez et al (2016) 58 synthesized the epoxy resin (ER), or diglycidyl ether (DGE), of mix′-BGF (2-21-22), abbreviated as mix′-BGF•DGE.…”