Photochemical key steps in the synthesis of surfactants from furfural-derived intermediates.
Furfural is oxidized to 2[5H]-furanone by using hydrogen peroxide or to 5-hydroxy-2[5H]-furanone by using photo-oxygenation. An amine function is introduced by photochemically induced radical addition of tertiairy amines, some of which carry an n-alkyl side chain as hydrophobic moiety. These amines are produced from fatty aldehydes and cyclic secondary amines. The resulting adducts are transformed into amphoteric surfactants possessing an ammonium and a carboxylate function. Amphoteric (pK(N) and isoelectric point) and surfactant properties such as the critical micelle concentration and the adsorption efficiency are determined.
Gassama
Abdoulaye
A
Institut de Chimie Moléculaire de Reims, UMR 6229 CNRS et Université de Reims Champagne-Ardenne, Equipe de Photochimie, UFR Sciences, B.P. 1039, 51687 Reims, Cedex 02, France.
Ernenwein
Cédric
C
Hoffmann
Norbert
N
D000588:Amines; D002264:Carboxylic Acids; D005662:Furaldehyde / Q000737:chemistry*; D008823:Micelles; D055668:Photochemical Processes; D000644:Quaternary Ammonium Compounds; D013501:Surface-Active Agents / Q000138:chemical synthesis*
D000588:Amines; D002264:Carboxylic Acids; D008823:Micelles; D000644:Quaternary Ammonium Compounds; D013501:Surface-Active Agents; D005662:Furaldehyde