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The Hydroamination of methyl acrylates with amines over zeolites

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Abstract

H-form zeolites, H-FAU and H-BEA have been studied as heterogeneous catalysts for the hydroamination. They catalyzed the reaction of methyl acrylate with aniline to give N-[2-(methoxycarbonyl)ethyl]aniline (1) as a main product. H-BEA and H-FAU zeolites efficiently catalyzed the hydroamination to afford anti-Markovnikov adduct as a main product. The conversion of aniline around 55–85% was achieved within 18 h over H-BEA and H-FAU zeolites with SiO2/Al2O3 molar ratio of 25–30; however, the formation of N,N-bis[2-(methoxycarbonyl)ethyl]aniline (2) as a product of double addition of methyl acrylate to aniline has also been observed as a by-product over H-BEA and H-FAU catalysts. The influences of the reaction parameters such as temperature and catalyst amount, and type of α,β-unsaturated esters and amines have been also investigated.

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Authors and Affiliations

  1. Department of Materials Science and Technology, Faculty of Engineering, Gifu University, Gifu, 501-1193, Japan

    Jana Horniakova, Kenichi Komura, Hisashi Osaki, Yoshihiro Kubota & Yoshihiro Sugi

  2. Department of Materials Science and Engineering, Graduate School of Engineering, Yokohama National University, Yokohama, 240-8501, Japan

    Yoshihiro Kubota

Authors
  1. Jana Horniakova
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  2. Kenichi Komura
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  3. Hisashi Osaki
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  4. Yoshihiro Kubota
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  5. Yoshihiro Sugi
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Correspondence to Yoshihiro Sugi.

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Horniakova, J., Komura, K., Osaki, H. et al. The Hydroamination of methyl acrylates with amines over zeolites. Catal Lett 102, 191–196 (2005). https://doi.org/10.1007/s10562-005-5854-6

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  • DOI: https://doi.org/10.1007/s10562-005-5854-6

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