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

Chloé Herrlé (1) , Sylvestre Toumieux (1) , Maryne Araujo (1) , Aurélien a M Peru (2) , Florent Allais (2) , Anne Wadouachi (1)

1 LG2A - Laboratoire de Glycochimie, des Antimicrobiens et des Agro-ressources - UMR CNRS 7378
2 ABI - Agro-Biotechnologies Industrielles

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 developed to produce new potential bio-based surfactants under solventless conditions. First, the reaction of 2H-HBO with primary or secondary amines was investigated followed by a sulfation reaction with the isolated N-alkyl-amide derivatives to obtain the corresponding N-alkyl sulfated compounds. The latter was 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 bio-based/renewable resources were obtained exclusively via a mechanochemical process. As a result, the sulfated derivatives of 2H-HBO were formed quantitatively and isolated in 69–79% overall yields. The critical micelle concentration (CMC) was determined for some of them which exhibited interesting anionic surfactant properties.

Domains: Chemical Sciences

Chloé Herrlé, Sylvestre Toumieux, Maryne Araujo, Aurélien a M Peru, Florent Allais, et al.. Mechanochemical synthesis of (4 S )- N -alkyl-4,5-bis-sulfooxypentanamide via a one-pot sequential aminolysis-sulfation reaction of ( S )-γ-hydroxymethyl-γ-butyrolactone (2H-HBO). Green Chemistry, 2022, ⟨10.1039/D2GC01345B⟩. ⟨hal-03722687⟩