Cellulose esterification with fatty acids and acetic anhydride in lithium chloride/N,N -dimethylacetamide medium

Carlos Vaca-Garcia (1) , Sophie Thiebaud-Roux (1) , Marie-Elisabeth Borredon (1) , Giuseppe Gozzelino (2)

1 CAI - Chimie Agro-Industrielle
2 Polito - Politecnico di Torino = Polytechnic of Turin

Homogeneous esterification of cellulose with saturated fatty acids (n‐octanoic to n‐octadecanoic) was accomplished with acetic anhydride co‐reactant in lithium chloride/N,N‐dimethylacetamide (LiCl/DMAc) medium. Cellulose mixed triesters (CMT) were obtained after 5 h at 130°C with an average of 2.2 acetyl groups and 0.8 fatty substituents per anhydroglucose unit. A mixed acetic‐fatty anhydride, formed in situ, accounts for the grafting of the fatty moiety. The purified products were characterized and compared to the analogous cellulose simple fatty triesters (CST) that were synthesized from fatty acid chlorides in pyridine medium. Dynamic contact angle with water, glass transition, and storage moduli were correlated with the length of the fatty substituents. The CMT proved to be highly hydrophobic and more mechanically resistant than the CST.

Mots clés: Mixed anhydrides; Hydrophobicity; Glass transition; Fatty acids; Fatty acid chlorides; Dynamic mechanical‐properties; Contact angle; Cellulose esters

Domaines: Polymères

Carlos Vaca-Garcia, Sophie Thiebaud-Roux, Marie-Elisabeth Borredon, Giuseppe Gozzelino. Cellulose esterification with fatty acids and acetic anhydride in lithium chloride/N,N -dimethylacetamide medium. Journal of the American Oil Chemists' Society, 1998, 75 (2), pp.315-319. ⟨10.1007/s11746-998-0047-2⟩. ⟨hal-02073810⟩