Synthesis and characterization of quaternized beta-chitin

Carbohydr Res. 2010 Jul 19;345(11):1609-12. doi: 10.1016/j.carres.2010.05.014. Epub 2010 May 24.

Abstract

Water-soluble 2'-O-hydroxypropyltrimethylammoniumchitin chloride (2'-O-HTACCt) was prepared directly from beta-chitin and 3-chloro-2-hydroxypropyltrimethylammonium chloride (CTA) in basic medium. The effect of alkali concentration, reaction temperature, reaction time, and dosage of CTA on yield and degree of substitution (DS) of 2'-O-HTACCt were studied. These quaternized chitin derivatives were characterized by FTIR and (1)H NMR spectroscopy, conductometric titration, and elemental analysis methods. Research results indicate that beta-chitin can react directly with CTA to produce a water-soluble 2'-O-HTACCt derivative with a high DS. The optimal preparation conditions were determined to be 35-40 wt% (aq NaOH), 40 degrees C (reaction temperature), 6h (reaction time), and 4 (molar ratio of CTA to beta-chitin unit).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-Infective Agents / chemical synthesis*
  • Anti-Infective Agents / chemistry*
  • Chitin / chemical synthesis*
  • Chitin / chemistry*
  • Magnetic Resonance Spectroscopy
  • Molecular Weight
  • Propanols / chemistry
  • Quaternary Ammonium Compounds / chemistry
  • Solubility
  • Spectroscopy, Fourier Transform Infrared
  • Water / chemistry

Substances

  • Anti-Infective Agents
  • Propanols
  • Quaternary Ammonium Compounds
  • Water
  • Chitin
  • (3-chloro-2-hydroxypropyl)trimethylammonium chloride