title: Pharmaceuticals and Surfactants from Alga-Derived Feedstock: Amidation of Fatty Acids and Their Derivatives with Amino Alcohols.
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.
authors.affiliation: Johan Gadolin Process Chemistry Centre, Åbo Akademi University, 20500 Turku (Finland).
authors.forename: Anastasia
authors.initials: A
authors.lastname: Tkacheva
authors.affiliation: Johan Gadolin Process Chemistry Centre, Åbo Akademi University, 20500 Turku (Finland).
authors.forename: Inkar
authors.initials: I
authors.lastname: Dosmagambetova
authors.affiliation: Johan Gadolin Process Chemistry Centre, Åbo Akademi University, 20500 Turku (Finland).
authors.forename: Yann
authors.initials: Y
authors.lastname: Chapellier
authors.affiliation: Johan Gadolin Process Chemistry Centre, Åbo Akademi University, 20500 Turku (Finland).
authors.forename: Päivi
authors.initials: P
authors.lastname: Mäki-Arvela
authors.affiliation: Johan Gadolin Process Chemistry Centre, Åbo Akademi University, 20500 Turku (Finland).
authors.forename: Imane
authors.initials: I
authors.lastname: Hachemi
authors.affiliation: Johan Gadolin Process Chemistry Centre, Åbo Akademi University, 20500 Turku (Finland).
authors.forename: Risto
authors.initials: R
authors.lastname: Savela
authors.affiliation: Johan Gadolin Process Chemistry Centre, Åbo Akademi University, 20500 Turku (Finland).
authors.forename: Reko
authors.initials: R
authors.lastname: Leino
authors.affiliation: Federal University of Rio de Janeiro, Department of Chemical Engineering, School of Chemistry, Rio de Janeiro (Brazil).
authors.forename: Carolina
authors.initials: C
authors.lastname: Viegas
authors.affiliation: Johan Gadolin Process Chemistry Centre, Åbo Akademi University, 20500 Turku (Finland).
authors.forename: Narendra
authors.initials: N
authors.lastname: Kumar
authors.affiliation: Johan Gadolin Process Chemistry Centre, Åbo Akademi University, 20500 Turku (Finland).
authors.forename: Kari
authors.initials: K
authors.lastname: Eränen
authors.affiliation: Johan Gadolin Process Chemistry Centre, Åbo Akademi University, 20500 Turku (Finland).
authors.forename: Jarl
authors.initials: J
authors.lastname: Hemming
authors.affiliation: Johan Gadolin Process Chemistry Centre, Åbo Akademi University, 20500 Turku (Finland).
authors.forename: Annika
authors.initials: A
authors.lastname: Smeds
authors.affiliation: Johan Gadolin Process Chemistry Centre, Åbo Akademi University, 20500 Turku (Finland). dmurzin@abo.fi.
authors.forename: Dmitry Yu
authors.initials: DY
authors.lastname: Murzin
mesh_terms: D000577:Amides / Q000737:chemistry; D000460:Chlorophyta / Q000737:chemistry*; D019856:Ethanolamine / Q000737:chemistry*; D005227:Fatty Acids / Q000737:chemistry*; D007930:Leucine / Q000031:analogs & derivatives* / Q000737:chemistry; D004364:Pharmaceutical Preparations / Q000737:chemistry; D011412:Propanolamines / Q000737:chemistry*; D012822:Silicon Dioxide / Q000737:chemistry; D013464:Sulfuric Acids / Q000737:chemistry; D013501:Surface-Active Agents / Q000737:chemistry; D017641:Zeolites / Q000737:chemistry
chemical_list: D000577:Amides; D005227:Fatty Acids; C509968:MCM-41; D004364:Pharmaceutical Preparations; D011412:Propanolamines; D013464:Sulfuric Acids; D013501:Surface-Active Agents; D017641:Zeolites; D019856:Ethanolamine; C417575:leucinol; D012822:Silicon Dioxide; C034448:2-aminopropanol; D007930:Leucine; C033158:sulfuric acid
keywords: amination; fatty acids; heterogeneous catalysis; mesoporous materials; zeolites