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)

• Published in: Green chemistry : an international journal and green chemistry resource : GC 2022-08, Vol.24 (15), p.5856-5861
• Main Authors: Herrlé, Chloé, Toumieux, Sylvestre, Araujo, Maryne, Peru, Aurélien, Allais, Florent, Wadouachi, Anne
• Format: Article
• Language: English
• Subjects: Amines; Ball milling; Butyrolactone; Cellulose; Chemical Sciences; Green chemistry; Micelles; Organic chemistry; Renewable resources; Sulfation; Surfactants; Sustainable yield
• ISSN: 1463-9262; 1463-9270
• DOI: 10.1039/D2GC01345B

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.