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Specific Organocatalysis in Amidation Reaction of Fatty Acid Methyl Esters with 3‐(Dimethylamino)‐1‐propylamine
Author(s) -
Shirshin Konstantin K.,
Esipovich Anton L.,
Kazantsev Oleg A.,
Rumyantsev Misha,
Korotaev Mikhail S.,
Rogozhin Anton E.
Publication year - 2021
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.202003197
Subject(s) - diethanolamine , propylamine , catalysis , chemistry , diethylene glycol , organic chemistry , organocatalysis , michael reaction , reaction conditions , mannich reaction , reaction rate , amine gas treating , enantioselective synthesis , ethylene glycol
Comparison of various organic compounds such as glycols, amines and alkanolamines as organocatalysts in amidation of fatty acid methyl esters with 3‐(dimethylamino)‐1‐propylamine was made for the first time. It was experimentally detected that catalysts containing OH‐groups (alcohols, glycols, glycerol and aminoalcohols) influence the reaction rate. Moreover, catalytic effect is depending on the catalysts geometry significantly. 1,5‐diols (e. g. diethylene glycol and diethanolamine) were found to accelerate the reaction more than other OH‐groups containing additives. It was supposed, that this catalytic effect is caused by specific associative interactions between reactants and 1,5‐diols, what was confirmed by quantum mechanics calculations. Catalysts concentration effects on the reaction rate were also investigated.