Pharmaceuticals and surfactants from alga-derived feedstock: amidation of fatty acids and their derivatives with amino alcohols

A1 Journal article (refereed)


Internal Authors/Editors


Publication Details

List of Authors: Anastasia Tkacheva, Inkar Dosmagambetova, Yann Chapellier, Päivi Mäki-Arvela, Imane Hachemi, Risto Savela, Reko Leino, Carolina Viegas, Narendra Kumar, Kari Eränen, Jarl Hemming, Annika Smeds, Dmitry Yu. Murzin
Publisher: Wiley-VCH
Publication year: 2015
Journal: ChemSusChem
Volume number: 8
Issue number: 16
Start page: 2670
End page: 2680
eISSN: 1864-564X


Abstract

Amidation of renewable feedstocks, such as fatty acids, esters, and Chlorella alga based biodiesel, was demonstrated with zeolites and mesoporous materials as catalysts and ethanolamine, alaninol, and leucinol. The last two can be derived from amino acids present in alga. The main products were fatty alkanol amides and the corresponding ester amines, as confirmed by NMR and IR spectroscopy. Thermal amidation of technical-grade oleic acid and stearic acid at 180 °C with ethanolamine were non-negligible; both gave 61 % conversion. In the amidation of stearic acid with ethanolamine, the conversion over H-Beta-150 was 80 % after 3 h, whereas only 63 % conversion was achieved for oleic acid; this shows that a microporous catalyst is not suitable for this acid and exhibits a wrinkled conformation. The highest selectivity to stearoyl ethanolamide of 92 % was achieved with mildly acidic H-MCM-41 at 70 % conversion in 3 h at 180 °C. Highly acidic catalysts favored the formation of the ester amine, whereas the amide was obtained with a catalyst that exhibited an optimum acidity. The conversion levels achieved with different fatty acids in the range C12–C18 were similar; this shows that the fatty acid length does not affect the amidation rate. The amidation of methyl palmitate and biodiesel gave low conversions over an acidic catalyst, which suggested that the reaction mechanism in the amidation of esters was different.


Keywords

amination, fatty acids, heterogeneous catalysis, mesoporous materials, zeolites

Last updated on 2019-20-07 at 06:40