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Thermal and Catalytic Amidation of Stearic Acid with Ethanolamine for Production of Pharmaceuticals and Surfactants

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Abstract

Thermal and catalytic amidation of stearic acid with ethanolamine in hexane was investigated using both microporous H-Beta and ZSM-5 zeolites, and mesoporous materials, H-MCM-36 and H-MCM-41, as catalysts in hexane. The main studied parameters were the catalyst structure and acidity, temperature and molar ratio of reactants. The results showed that thermal amidation of stearic acid with an equimolar ratio of ethanolamine was substantial giving 61 % conversion in 3 h. The highest conversion and selectivity to stearoylethanolamide, being 79 and 83 %, respectively, were achieved with microporous, relatively strongly acidic H-Beta-150 catalyst. Stearoylethanolamide and the corresponding esteramide were the main products. An optimum amount of Brønsted acid sites in the catalyst was required to achieve high yield and selectivity towards stearoylethanolamide. With increasing amount of Brønsted acid sites more esteramide was formed. Typically esteramide selectivity increased in the catalytic amidation of stearic acid with increasing conversion due to consecutive reactions. Low conversions were obtained, when increasing the molar ratio of stearic acid to ethanolamine. In addition, an excess of ethanolamine suppressed the reaction due to its strong adsorption on zeolite surface. An optimum reaction temperature was 180 °C. The mass transfer limitations were not fully absent in the reaction. A reaction mechanism, including both parallel and consecutive pathways was proposed.

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Acknowledgments

Prof. R. Leino and Dr. R. Savela from Johan Gadolin Process Chemistry Centre at Åbo Akademi University are acknowledged from their contribution to this work.

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Authors and Affiliations

  1. Johan Gadolin Process Chemistry Centre, Åbo Akademi University, 20500, Turku, Finland

    Päivi Mäki-Arvela, Anastasia Tkacheva, Inkar Dosmagambetova, Yann Chapelliere, Imane Hachemi, Narendra Kumar, Atte Aho & Dmitry Yu Murzin

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  1. Päivi Mäki-Arvela
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  2. Anastasia Tkacheva
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  7. Atte Aho
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  8. Dmitry Yu Murzin
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Correspondence to Dmitry Yu Murzin.

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Mäki-Arvela, P., Tkacheva, A., Dosmagambetova, I. et al. Thermal and Catalytic Amidation of Stearic Acid with Ethanolamine for Production of Pharmaceuticals and Surfactants. Top Catal 59, 1151–1164 (2016). https://doi.org/10.1007/s11244-016-0636-5

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  • DOI: https://doi.org/10.1007/s11244-016-0636-5

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