Abstract
The preparation of fatty acid methyl esters by transesterification of acyl lipids using trimethylsulfonium hydroxide (TMSH) as a base catalyst is a convenient GC derivatization procedure of growing interest. It has now been found that lipids containing amido groups, e.g. fatty acid amides and fatty acid ethanolamides, are partially N- and/or O-methylated by the pyrolytic reaction with TMSH occurring in the injector of the gas chromatograph. The various reaction products, i.e. N-methyl and N,N-dimethyl fatty acid amides as well as N-methyl, O-methyl and N,O-dimethyl fatty acid ethanolamides, were analyzed by GC and GC–MS. Our results show that derivatization with TMSH is not generally recommended for the derivatization of lipid mixtures containing fatty acid amides or ethanolamides. However, some of the methylation products as well as the sequence of reactions which finally lead to N,N-dimethyl fatty acid amides and N,O-dimethyl fatty acid ethanolamides, respectively, can be of diagnostic value for the structural analysis of the various fatty acid amides by GC–MS.
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