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

ChemSusChem. 2009;2(12):1130-7. doi: 10.1002/cssc.200900150.

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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amines
  • Carboxylic Acids
  • Furaldehyde / chemistry*
  • Micelles
  • Photochemical Processes*
  • Quaternary Ammonium Compounds
  • Surface-Active Agents / chemical synthesis*

Substances

  • Amines
  • Carboxylic Acids
  • Micelles
  • Quaternary Ammonium Compounds
  • Surface-Active Agents
  • Furaldehyde