Contribution to the structural elucidation of 10 isomers of technical p-nonylphenol.

Gas chromatography-mass spectrometry (GC-MS) with a 100 m capillary column at different oven temperatures is employed to separate isothermally p-nonylphenol into 21 isomers. Analysis of the resulting mass spectra of these isomers indicates that they could be classified into six groups with respect to different configurations of the alpha- and beta-C-atoms on the alkyl chains. Based on these basic structures nonylphenol isomers are synthesized and also characterized by GC-MS. The obtained data elucidate the complete structures of 10 nonylphenol isomers of the technical mixture. The most important features of the mass spectra and the 1H and 13C nuclear magnetic resonance (NMR) spectra of these isomers are presented.