Oxidation and oligomerization of ethyl linoleate under the influence of the combination of ascorbic acid 6-palmitate/iron-2-ethylhexanoate

F. Micciche, J. van Haveren, E.A. Oostveen, W. Ming, R. van der Linde

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    Abstract

    In this paper we report the oxidation and oligomerization of ethyl linoleate (EL), a model compound for alkyd resins, under the influence of iron-2-ethylhexanoate (Fe-eh) in combination with ascorbic acid 6-palmitate (AsA6p) at different AsA6p/Fe-eh molar ratios (0/1¿4/1). Reactions were studied in time by FT-IR, NMR, size exclusion chromatography (SEC) and peroxide amount determination. The oxidation and oligomerization of EL were accelerated by the combination of AsA6p and Fe-eh, and the catalytic properties of the catalysts were strongly dependent on the molar ratio AsA6p/Fe-eh. The molar ratio of 2/1 appeared to be optimal, at which both the oxidation and oligomerization of EL were the fastest. At molar ratio smaller than 2/1, or only in the presence of Fe-eh, the EL oxidation showed a time lag of up to 100 h; above the ratio 2/1 the rates of both EL oxidation and oligomerization decreased. Results are explained in terms of the multi-facet role played by AsA6p: its pro-oxidant or anti-oxidant properties, depending on the ratio of AsA6p/Fe-eh, and its effect on the Fe-eh complex.
    Original languageEnglish
    Pages (from-to)174-181
    JournalApplied Catalysis A-General
    Volume297
    Issue number2
    DOIs
    Publication statusPublished - 2006

    Keywords

    • unsaturated fatty-acids
    • metal-catalyzed autoxidation
    • lipid-peroxidation
    • mass-spectrometry
    • alkyd resins
    • linseed oil
    • cross-linking
    • paints
    • drier
    • iron(iii)

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