Mechanochemical synthesis of (4S)-N-alkyl-4,5-bis-sulfooxypentanamide via a one-pot sequential aminolysis-sulfation reaction of (S)-γhydroxymethyl-γ-butyrolactone (2H-HBO) - AgroParisTech Access content directly
Journal Articles Green Chemistry Year : 2022

Mechanochemical synthesis of (4S)-N-alkyl-4,5-bis-sulfooxypentanamide via a one-pot sequential aminolysis-sulfation reaction of (S)-γhydroxymethyl-γ-butyrolactone (2H-HBO)

Abstract

To valorize further the highly valuable bio-based platform (S)-γ-hydroxymethyl-γ-butyrolactone (2H-HBO), whose sustainable kiloscale-synthesis from cellulose-derived levoglucosenone (LGO) has been validated, a mechanochemical strategy was developped to produce new potential bio-based surfactants in solventless conditions. First, the reaction of 2H-HBO with primary or secondary amines was investigated followed by a sulfation reaction on the isolated N-alkyl-amide derivatives to obtain the corresponding N-alkyl sulfated compounds. These latter were then obtained by an optimized one-pot sequential aminolysis-sulfation in a planetary ball mill with excellent efficiency. For the first time, sulfated compounds arising from biobased/renewable ressources were obtained exclusively via a mechanochemical process. As a result, these sulfated derivatives of 2H-HBO were formed quantitatively and isolated in 69-79% overall yields. Critical micellar concentration (CMC) was evaluated for some of them and revealed an interesting anionic surfactant properties.
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hal-04153779 , version 1 (06-07-2023)

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Chloé Herrlé, Sylvestre Toumieux, Maryne Araujo, Aurelien Peru, Florent Allais, et al.. Mechanochemical synthesis of (4S)-N-alkyl-4,5-bis-sulfooxypentanamide via a one-pot sequential aminolysis-sulfation reaction of (S)-γhydroxymethyl-γ-butyrolactone (2H-HBO). Green Chemistry, 2022, 24 (15), pp.5856-5861. ⟨10.1039/D2GC01345B⟩. ⟨hal-04153779⟩
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