Analysis of sulfophthalimide and some of its derivatives by liquid chromatography–electrospray ionization tandem mass spectrometry

Abstract

A system was developed for the separation of sulfophthalimide (SPI), sulfophthalamide (SPAM), sulfophthalamic acid (SPAA) and sulfophthalic acid (SPA) by ion-pair liquid chromatography and their detection by electrospray ionization tandem mass spectrometry (ESI-MS–MS). Except for SPAM, the 3- and 4-sulfo-isomers of the analytes were separated by HPLC using volatile tributylamine as ion-pairing agent. Initial fragmentations of the analytes in the negative mode involve losses of CO 2 or HNCO or condensation via H 2O or NH 3 elimination. ortho-Effects of the sulfonate group were recognized in the fragmentation of the respective 3-sulfo-isomers and allowed us to assign the order of elution of the SPAA isomers. Quantitative analysis of these sulfonated aromatic compounds with MRM detection was elaborated and resulted in detection limits ranging from 1 pg for SPA to 13 pg for SPAA isomers and in limits of quantification of 2–10 μg/L for 5 μL volumes of injected tap water, municipal wastewater or industrial effluents up to salt contents of 0.5–1 g/L. The method was applied to study the isomer-specific chemical and microbial transformations of SPI, which was previously shown to be formed by white-rot fungi from sulfophthalocyanine textile dyes.