Efficient method of starch functionalization to bis-quaternary structure unit

Int J Biol Macromol. 2015 Sep:80:498-505. doi: 10.1016/j.ijbiomac.2015.07.011. Epub 2015 Jul 15.

Abstract

This paper presents the synthesis of bis-quaternary starch by innocuous reagents. For this, starch was functionalized to di-aldehyde structure by periodate oxidation. Aldehyde is reactive and amenable to further derivatization to amine structure. It was functionalized to amine via the modified Leuckart-Wallach reaction. Then, the aminated starch was modified to the quaternary form by the exhaustive methylation. The structural characterization of synthesized compounds was performed using titrimetric analytical estimation, FTIR, (1)H NMR, (13)C NMR, and SEM-EDX. Analytical results showed 58.8% aldehyde content in di-aldehyde starch. The synthesized quaternary derivatives with gemini like structure showed high degree of quaternization 62%. In conclusion, the applied protocol is efficient and revealed high extent of modification with almost good uniformity from the characterization studies.

Keywords: Di-aldehyde starch; Gemini like structure; Quaternary starch.

MeSH terms

  • Aldehydes / chemical synthesis
  • Carbohydrate Conformation
  • Green Chemistry Technology
  • Oxidation-Reduction
  • Quaternary Ammonium Compounds / chemical synthesis*
  • Starch / analogs & derivatives*
  • Starch / chemical synthesis*
  • Starch / ultrastructure
  • X-Ray Diffraction

Substances

  • Aldehydes
  • Quaternary Ammonium Compounds
  • Starch