Journal of Surfactants and Detergents

, Volume 14, Issue 1, pp 51–63

Synthesis and Surface-Active Properties of Uronic Amide Derivatives, Surfactants from Renewable Organic Raw Materials

  • Pascal Laurent
  • Hary Razafindralambo
  • Bernard Wathelet
  • Christophe Blecker
  • Jean-Paul Wathelet
  • Michel Paquot
Original Article

DOI: 10.1007/s11743-010-1205-8

Cite this article as:
Laurent, P., Razafindralambo, H., Wathelet, B. et al. J Surfact Deterg (2011) 14: 51. doi:10.1007/s11743-010-1205-8

Abstract

Short chemical syntheses were developed to produce a new set of surfactants from uronic acids derived from widely available raw materials. Three different strategies were used to synthesize uronic amide derivatives, the structures of which were totally characterized by spectrometric methods (IR, MS, 1H-RMN and 13C-RMN). The best one, using an acid chloride as the synthetic intermediate, furnished the expected amides as a mixture of anomers in 46–58% global yield. Surface-active properties (CMC, γcmc, Γmax, Amin) of homologous series of uronic acid N-alkylamides from C8 to C18 were also assessed. In general, these sugar-based surfactants exhibited good surface-activities, and appeared as valuable nonionic surfactants compared to octylphenol 9–10 ethylene oxide condensate, the most well-known nonionic surfactant. Increasing the alkyl chain length influenced the CMC values for both glucuronic and galacturonic N-alkylamide derivatives. The galacturonic N-alkylamides decreased γcmc at slower values than their counterpart’s glucuronic N-alkylamides.

Keywords

Uronic acidAmide formationCarbohydratesCritical micellar concentrationSurface tension

Abbreviations

COSY

Correlation spectroscopy

DCC

Dicyclohexyl carbodiimide

DMF

Dimethyl formamide

DMSO

Dimethyl sulfoxide

ESIMS

Electrospray ionisation mass spectrometry

HMBC

Heteronuclear multiple bond correlation

HSQC

Heteronuclear single quantum correlation

NOESY

Nuclear Overhauser effect spectroscopy

TLC

Thin layer chromatography

TMS

Tetramethylsilane

Copyright information

© AOCS 2010

Authors and Affiliations

  • Pascal Laurent
    • 1
    • 2
  • Hary Razafindralambo
    • 3
  • Bernard Wathelet
    • 1
  • Christophe Blecker
    • 3
  • Jean-Paul Wathelet
    • 2
  • Michel Paquot
    • 1
  1. 1.Unit of Biological and Industrial Chemistry, Gembloux Ago-Bio TechUniversity of LiegeGemblouxBelgium
  2. 2.Unit of General and Organic Chemistry, Gembloux Ago-Bio TechUniversity of LiegeGemblouxBelgium
  3. 3.Unit of Food Technology, Gembloux Agro-Bio TechUniversity of LiegeGemblouxBelgium