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 H-1 and C-13 nuclear magnetic resonance (NMR) spectra of these isomers are presented.