Journal of the Serbian Chemical Society 2012 Volume 77, Issue 2, Pages: 147-157
https://doi.org/10.2298/JSC110616195G
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Fractionation of complex mixtures of naphthenic acids, their characterization and biological activity
Grbović Ljubica (Department of Chemistry, Biochemistry and Environmental Protection, Faculty of Sciences, Novi Sad)
Pavlović Ksenija 
(Department of Chemistry, Biochemistry and Environmental Protection, Faculty of Sciences, Novi Sad)
Prekodravac Bojana (Department of Chemistry, Biochemistry and Environmental Protection, Faculty of Sciences, Novi Sad)
Kuhajda Ksenija (Department of Chemistry, Biochemistry and Environmental Protection, Faculty of Sciences, Novi Sad)
Kevrešan Slavko (Faculty of Agriculture, Novi Sad)
Popsavin Mirjana (Department of Chemistry, Biochemistry and Environmental Protection, Faculty of Sciences, Novi Sad)
Milić Jelena (Department of Chemistry, Biochemistry and Environmental Protection, Faculty of Sciences, Novi Sad)
Ćirin-Novta Vera (Department of Chemistry, Biochemistry and Environmental Protection, Faculty of Sciences, Novi Sad)
Naphthenic acids (NAs) are complex mixtures of cycloaliphatic and
alkyl-substituted acyclic carboxylic acids whose overall characteristics are
determined by the composition of the mixture. A complex mixture of NAs from a
commercial fraction of atmospheric oil of the Vojvodina naphthenic crude
"Velebit" (Serbia) was separated into narrower fractions on the basis of
their acidity. Electrospray ionization mass spectrometry analysis of the
fractions showed the occurrence of structural differentiation of acids. By
extraction at pH 3-5, about 50% of the total mass of acids was separated,
consisting predominantly of tricyclic and bicyclic structures. Acids of lower
acidity, (about 22%), separated at pH 9 and 10, and their dominant
constituents were acids with three, four and five rings. A correlation was
found between the dominant structure and the biological activity of NAs of
the fractions. The fraction extracted at pH 8, also with dominant bicyclic
and tricyclic structures, showed the highest auxin and gibberellin
activities.
Keywords: naphthenic acids, fractionation, structural analysis, biological activity