Synthesis, physico-chemical properties and complexing abilities of new amphiphilic ligands from D-galacturonic acid.
This paper describes a convenient and efficient synthesis of new complexing surfactants from d-galacturonic acid and n-octanol as renewable raw materials in a two-step sequence. In the first step, simultaneous O-glycosidation-esterification under Fischer conditions was achieved. The anomeric ratio of the products was studied based on the main experimental parameters and the activation mode (thermal or microwave). In the second step, aminolysis of the n-octyl ester was achieved with various functionalized primary amines under standard thermal or microwave activation. The physico-chemical properties of these new amphiphilic ligands were measured and these compounds were found to exhibit interesting surface properties. Complexing abilities of one uronamide ligand functionalized with a pyridine moiety toward Cu(II) ions was investigated in solution by EPR titrations. A solid compound was also synthesized and characterized, its relative structure was deduced from spectroscopic data.
Allam
Anas
A
Université de Reims Champagne-Ardenne, Institut de Chimie Moléculaire de Reims, CNRS UMR 6229, UFR des Sciences Exactes et Naturelles, Bâtiment 18 Europol'Agro, Reims Cedex 2, France.
Behr
Jean-Bernard
JB
Dupont
Laurent
L
Nardello-Rataj
Véronique
V
Plantier-Royon
Richard
R
D004578:Electron Spin Resonance Spectroscopy; D006603:Hexuronic Acids / Q000737:chemistry*; D008024:Ligands; D008872:Microwaves; D008956:Models, Chemical; D015394:Molecular Structure
D006603:Hexuronic Acids; D008024:Ligands; C007819:galacturonic acid