Syntheses of surfactants from oleochemical epoxides

Siegfried Warwel,Herbert Schier,Berthold Wiege,Mark Rusch Gen Klaas,Falk Bruse

doi:10.1051/ocl.2001.0057

Abstract

Sugar-based surfactants were obtained in good yields (up to 100%) under mild conditions (70°C, methanol or mixtures of methanol and water) by ring-opening of terminal epoxides with aminopolyols, derived from glucose. Reaction of N-methyl glucamine with epoxides from even-numbered C4-C18 alpha-olefins or from terminal unsaturated fatty acid methyl esters leads to linear products, while corresponding reactions with N-dodecyl glucamine or glucamine yield surfactants with different Y-structures. Products obtained by conversion of omega-epoxy fatty acid methyl esters were saponificated with NaOH or hydrolyzed enzymatically to sodium salts or free acids respectively, which are amphoteric surfactants. Studies of the surfactants at different pH-values demonstrate different surface active properties in aqueous solutions. Critical micelle concentrations (c.m.c.) in a range between 2 and 500mg/l and surface tensions of 25-40mN/m were measured for several of the synthesized sugar-based surfactants. The ring-opening products are rather poor foamers, whereas some of the corresponding hydrobromides show good foaming properties.

Highlights

Syntheses of surfactants from oleochemical epoxidesDes réactions de N-méthylglucamine avec des oxydes d'alcoylènes supérieurs terminaux (C4-C18) ou des oxydes d'esters méthyliques d'acides gras à terminaisons insaturées amènent aux produits linéaires, tandis que des réactions avec de la N-dodécylglucamine ou de la glucamine amènent aux surfactants avec des structures en Y différentes
We have developed a new mild method [7, 8] and applied special terminal epoxides for this purpose
As starting polyolamines for syntheses of surfactants different glucamines were used, which are industrially available from glucose by reductive amination using NH3, methyl amine or dodecyl amine, respectively (Figure 1)

Summary

Syntheses of surfactants from oleochemical epoxides

Des réactions de N-méthylglucamine avec des oxydes d'alcoylènes supérieurs terminaux (C4-C18) ou des oxydes d'esters méthyliques d'acides gras à terminaisons insaturées amènent aux produits linéaires, tandis que des réactions avec de la N-dodécylglucamine ou de la glucamine amènent aux surfactants avec des structures en Y différentes. Summary : Sugar-based surfactants were obtained in good yields (up to 100%) under mild conditions (70°C, methanol or mixtures of methanol and water) by ring-opening of terminal epoxides with aminopolyols, derived from glucose. Reaction of N-methyl glucamine with epoxides from evennumbered C4-C18 alpha-olefins or from terminal unsaturated fatty acid methyl esters leads to linear products, while corresponding reactions with N-dodecyl glucamine or glucamine yield surfactants with different Y-structures. Sugar based surfactants, such as alkyl polyglucosides, fatty acid N-methyl glucamides, sorbitan esters and sucrose esters gained importance in the last decade [1]. We have developed a new mild method [7, 8] and applied special terminal epoxides for this purpose

Starting materials

Findings

Surface active properties