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Optimized reaction conditions for the cross-metathesis of methyl oleate and oleylamine with ethyl acrylate

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Abstract

The cross-metathesis of methyl oleate and oleylamine with ethyl acrylate has been studied using three different ruthenium-based second-generation catalysts. Emphasis was on determining the smallest amount of catalyst necessary for full conversion of technical grade educts. Conversion of methyl oleate is best performed in the presence of 10 equiv. ethyl acrylate without use of additional solvent whereas oleylamine cannot be used directly and protection of the amino group is necessary. An easy protection procedure for oleylamine with acetic anhydride was developed and the best results for cross-metathesis of N-acetyloleylamine were obtained in toluene solution.

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Acknowledgments

We are grateful to HEC for financial support of M.A. and Umicore for the generous gift of materials. Financial support by the European Community (CP-FP 211468-2 EUMET) is acknowledged.

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Authors and Affiliations

  1. Institute for Chemistry and Technology of Materials, Graz University of Technology, Stremayrgasse 9, 8010, Graz, Austria

    Mudassar Abbas & Christian Slugovc

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  1. Mudassar Abbas
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  2. Christian Slugovc
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Correspondence to Christian Slugovc.

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Abbas, M., Slugovc, C. Optimized reaction conditions for the cross-metathesis of methyl oleate and oleylamine with ethyl acrylate. Monatsh Chem 143, 669–673 (2012). https://doi.org/10.1007/s00706-011-0717-x

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  • DOI: https://doi.org/10.1007/s00706-011-0717-x

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