Kinetics in the thermal and catalytic amidation of C18 fatty acids with ethanolamine for the production of pharmaceuticals

Mäki‐Arvela, Päivi; Kumar, Narendra; Chapelliere, Y.; Simakova, Irina L.; Murzin, Dmitry Yu.

doi:10.1007/s11144-016-1086-6

Cited by 7 publications

(2 citation statements)

References 30 publications

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“…26,27 Though, the use of the heterogeneous catalyst for the direct amidation of fatty acids using alkanol amines have been investigated scarcely. [28][29][30][31] Most of the time, the heterogeneous catalyst-based reactions were carried out in the presence of solvents viz, an excess of acetic acid was used with supported iron catalyst (yield = 96%, time 1-5 hours) and Fe-beta zeolites (yield = 52%, time 15 minutes). 32,33 For solvent-free conditions, Sn IV complexes, 34 the Deoxo-Fluor reagent, 35 Sm III complexes, 36 and dithiocarbamates 37 have been employed to obtain the desired amide derivates.…”

Section: Introductionmentioning

confidence: 99%

“…To make the process more industrial benign and cheaper, and to avoid the tedious catalyst separation, the use of heterogeneous catalysts could be an attractive option that can provide easy separation, reusability, and high FFA and moisture content resistance . Though, the use of the heterogeneous catalyst for the direct amidation of fatty acids using alkanol amines have been investigated scarcely . Most of the time, the heterogeneous catalyst‐based reactions were carried out in the presence of solvents viz, an excess of acetic acid was used with supported iron catalyst (yield = 96%, time 1‐5 hours) and Fe‐beta zeolites (yield = 52%, time 15 minutes) .…”

Section: Introductionmentioning

confidence: 99%

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One‐pot solvent‐free transformation of natural triglycerides to ester and amide derivatives over CaO@KC nanostructured catalysts

2020

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Summary In the present report, the fatty acid alkyl esters and fatty acid amides were synthesized from natural triglycerides by highly selective solvent‐free one‐step methods using 3.5‐CaO@KC‐400 nanocrystals as a heterogeneous catalyst. A modified wetness chemical impregnation method was used to prepared potassium carbonate‐doped CaO, ZnO, and MgO nanocrystals. The prepared 3.5‐CaO@KC‐400 nanocrystals were found as the most efficient heterogeneous catalyst (5%, w/w) for amidation (6:1 M ratio of diethanolamine/oil, 110°C) and transesterification (12:1 M ratio of methanol/oil, 65°C) of waste cooking oil and took 30 minutes for the completion of both the reactions. The 3.5‐CaO@KC‐400 nanocrystals were found to be efficient at room temperature also and reused for 10 reaction cycles for both reactions. The pseudo‐first‐order kinetic model was applied and the first‐order rate constant was calculated as 0.15 minute−1 and 0.103 minute−1 for the amidation and transesterification reactions of waste cooking oil, respectively.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

One‐pot solvent‐free transformation of natural triglycerides to ester and amide derivatives over CaO@KC nanostructured catalysts

2020

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Facile amidation of esters with aromatic amines promoted by lanthanide tris (amide) complexes

Zhao

Guo

Chen

et al. 2020

Applied Organom Chemis

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The development of catalysts capable of catalyzing amidation of esters with amines to construct amides under mild conditions is of great importance. Compared to aliphatic amines, the direct catalytic amidation of esters with less nucleophilic aromatic amines is rather difficult. Employing simple lanthanide tris (amide) complexes Ln[N (SiMe3)2]3(μ‐Cl)Li (THF)3 as the catalysts, it was found a broad range of aromatic amines and esters were efficiently converted into various amides in good yields under mild conditions. A plausible mechanism for this transformation was experimentally supported as starting from an amide exchange reaction between the lanthanide tris (amide) complex and the substrate amine.

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Effect of the acyl-group length on the chemoselectivity of the lipase-catalyzed acylation of propranolol—a computational study

2021

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Kinetics in the thermal and catalytic amidation of C18 fatty acids with ethanolamine for the production of pharmaceuticals

Cited by 7 publications

References 30 publications

One‐pot solvent‐free transformation of natural triglycerides to ester and amide derivatives over CaO@KC nanostructured catalysts

One‐pot solvent‐free transformation of natural triglycerides to ester and amide derivatives over CaO@KC nanostructured catalysts

Facile amidation of esters with aromatic amines promoted by lanthanide tris (amide) complexes

Effect of the acyl-group length on the chemoselectivity of the lipase-catalyzed acylation of propranolol—a computational study

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