Silylation of Non-Terminal Double Bonds of Natural Oils

Chetan Tambe, Sudhanwa Dewasthale, Xiangke Shi, Daniel Graiver, Ramani Narayan

    Research output: Contribution to journalArticle

    • 1 Citations

    Abstract

    Silylation of non-terminal double bonds of unsaturated fatty acids with reactive organosilicons was successfully accomplished using the ‘Ene’ reaction route. The ‘Ene’ reaction, which is a subset of the famous Diels Alder reaction, enables grafting of vinyl silanes onto unsaturated organic molecules irrespective of the position of the double bond. This procedure was used to graft vinyltrialkoxysilanes onto unsaturated fatty acids of various triglyceride oils. Methyl oleate and methyl stearate were used as model compounds to investigate this reaction. 1H NMR and TGA were used to characterize the structure of the silylation products and to determine the extent of grafting as a function of reaction conditions. It was found that this grafting reaction follows a second order kinetics. Under extreme conditions a silyl-ester redistribution reaction can also occur where an alkoxy group attached to the silicon atom is exchanged with an alkoxy group of the organic ester. Grafting vinyltrimethoxysilane onto natural oils such as soybean, canola and Abyssinian oils leads to a convenient one-component, moisture activated cure system of these natural oils.

    Original languageEnglish (US)
    JournalSilicon
    DOIs
    StateAccepted/In press - Jun 12 2015

    Profile

    Unsaturated fatty acids
    Esters
    Silanes
    Grafts
    Moisture
    Nuclear magnetic resonance
    Silicon
    Atoms
    Molecules
    Kinetics
    Anthralin
    Dapsone
    Competitive Binding

    Keywords

    • Silylation
    • Soybean oil
    • Triglyceride
    • Vinyltrimethoxysilane
    • ‘Ene’ reaction

    ASJC Scopus subject areas

    • Electronic, Optical and Magnetic Materials

    Cite this

    Silylation of Non-Terminal Double Bonds of Natural Oils. / Tambe, Chetan; Dewasthale, Sudhanwa; Shi, Xiangke; Graiver, Daniel; Narayan, Ramani.

    In: Silicon, 12.06.2015.

    Research output: Contribution to journalArticle

    Tambe C, Dewasthale S, Shi X, Graiver D, Narayan R. Silylation of Non-Terminal Double Bonds of Natural Oils. Silicon. 2015 Jun 12. Available from, DOI: 10.1007/s12633-015-9299-2

    Tambe, Chetan; Dewasthale, Sudhanwa; Shi, Xiangke; Graiver, Daniel; Narayan, Ramani / Silylation of Non-Terminal Double Bonds of Natural Oils.

    In: Silicon, 12.06.2015.

    Research output: Contribution to journalArticle

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