Analysis of chlorinated, sulfochlorinated and sulfonamide derivatives of n-tetradecane by gas chromatography/mass spectrometry

Abstract

The photosulfochlorination of n-tetradecane by sulfuryl chloride leads to a reaction mixture containing unreacted n-tetradecane, chloro n-tetradecanes and n-tetradecanesulfonyl chlorides. Direct and simultaneous GC analysis of the mixture of the sulfochlorinated and chlorinated isomers is followed by mass spectrometry identification of all the components either by electron impact (EI-MS) and by negative and positive chemical ionisation (NCI-MS and PCI-MS). With the goal of performing an accurate quantitative GC analysis, and as n-tetradecanesulfonyl chlorides prone to degrade partially into the corresponding chlorides, the former are converted to N,N-diethylsufonamides, more stable thermally, and then analysed by GC/EI-MS and GC/PCI-MS. The chloro n-tetradecanes, sulfonylchlorides and sulfonamides spectra present strong similarities. However, some differences between terminal and internal isomers are noticed and the peculiar behaviour of sulfonamides is emphasized.