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Issue 8, 2017
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A hydroaminomethylation/hydrohydroxymethylation sequence for the one pot synthesis of aminohydroxytriglycerides

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Abstract

In this paper we report the one pot functionalization of the carbon–carbon double bonds of triglycerides via a cascade hydroaminomethylation (HAM)/hydrohydroxymethylation (HHM) reaction. The carbon–carbon double bonds are first hydroformylated using a Rh-catalyst. The produced aldehydes react with secondary amines to yield enamines which are then reduced to tertiary amines. Interestingly, the latter act as ligands of Rh-species capable of hydrogenating the remaining formyl groups into alcohols. As a result, the final triglycerides are substituted by both aminomethyl and hydroxymethyl groups. Of interest, no phosphane ligand is used to stabilize the Rh-species. Moreover, the proportion of aminomethyl and hydroxymethyl groups grafted onto the triglyceride fatty chains can be finely adjusted by a careful choice of the experimental conditions, especially the nature and the amount of the amine, the reaction temperature, and the CO/H2 pressure. The resulting amino-hydroxylated triglycerides are unprecedented biosourced building blocks whose applications could be of major interest, especially in the field of polymer chemistry.

Graphical abstract: A hydroaminomethylation/hydrohydroxymethylation sequence for the one pot synthesis of aminohydroxytriglycerides

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Publication details

The article was received on 06 Jan 2017, accepted on 24 Mar 2017 and first published on 28 Mar 2017


Article type: Paper
DOI: 10.1039/C7GC00061H
Citation: Green Chem., 2017,19, 1940-1948
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    A hydroaminomethylation/hydrohydroxymethylation sequence for the one pot synthesis of aminohydroxytriglycerides

    T. Vanbésien, E. Monflier and F. Hapiot, Green Chem., 2017, 19, 1940
    DOI: 10.1039/C7GC00061H

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