Photochemical key steps in the synthesis of surfactants from furfural-derived intermediates.

ChemSusChem

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.

Published: April 2010

AI Article Synopsis

  • Furfural can be oxidized to different compounds using hydrogen peroxide or photo-oxygenation, leading to 2[5H]-furanone or 5-hydroxy-2[5H]-furanone, respectively.
  • The introduction of an amine function involves a photochemical process using tertiary amines derived from fatty aldehydes and cyclic secondary amines, some of which have hydrophobic n-alkyl side chains.
  • The resulting compounds are amphoteric surfactants that feature both ammonium and carboxylate functions, with properties such as pK(N), isoelectric point, critical micelle concentration, and adsorption efficiency being evaluated.

Article Abstract

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.

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Source
http://dx.doi.org/10.1002/cssc.200900150DOI Listing

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