Issue 5, 2025

The sustainable and catalytic synthesis of N,N-alkylated fatty amines from fatty acids and esters

Abstract

The reductive amination of fatty acids (FAs) and fatty acid methyl esters (FAMEs) has been identified as a green and effective method to produce N,N-dimethylalkylamines (ADMAs). With current technology, this reaction requires at least two reaction steps. Here, we report a heterogeneous catalytic system for the one-pot synthesis of ADMAs from FA(ME)s, utilizing solely H2 and methylamines (i.e. di- and trimethylamine). The reaction requires two recyclable catalysts: ortho-Nb2O5 for the amidation of FA(ME)s and PtVOx/SiO2 for the hydrogenation of the in situ generated fatty amide to ADMAs. The developed system has a wide range of applicability: it is able to convert all natural FAs to ADMAs (yields up to 90%) and also other tertiary amines were synthesized. Aside from the development of a sustainable and industrially applicable process (e.g. utilizing benign solvents or performing solventless reactions), a kinetic model was developed that describes the reaction rate's relationship with key process parameters such as the H2 pressure and water content. By tuning the reaction conditions, different ratios of primary, secondary and tertiary fatty amines can be obtained.

Graphical abstract: The sustainable and catalytic synthesis of N,N-alkylated fatty amines from fatty acids and esters

Supplementary files

Article information

Article type
Paper
Submitted
10 Nov 2024
Accepted
30 Dec 2024
First published
03 Jan 2025

Green Chem., 2025,27, 1410-1422

The sustainable and catalytic synthesis of N,N-alkylated fatty amines from fatty acids and esters

R. Coeck, N. Claes, T. Cuypers, S. Bals and D. E. De Vos, Green Chem., 2025, 27, 1410 DOI: 10.1039/D4GC05740F

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