Bioglycerol-based sulphonic acid functionalized carbon: an efficient and recyclable, solid acid catalyst for the regioselective azidolysis of epoxides in aqueous acetonitrile

J Oleo Sci. 2013;62(10):849-55. doi: 10.5650/jos.62.849.

Abstract

A convinent and efficient method was developed for the synthesis of 1,2-azidoalcohols by ring opening of terminal epoxides with sodium azide employing glycerol-based sulphonic acid functionalized carbon as heterogeneous catalyst in aqueous acetonitrile. The reaction is highly regioselective and affords the corresponding products in excellent yields (78-100%) under mild reaction conditions. The catalyst exhibited efficient reusability without loosing its activity even after 5 cycles of azidolysis of methyl 10,11-epoxy undecanoate under optimized conditions within 2 h.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetonitriles / chemistry*
  • Alcohols / chemical synthesis*
  • Azides / chemical synthesis*
  • Carbon / chemistry*
  • Catalysis
  • Chemistry, Organic / methods*
  • Epoxy Compounds / chemistry*
  • Glycerol / chemistry*
  • Sodium Azide / chemistry*
  • Sulfonic Acids / chemistry*
  • Time Factors
  • Water / chemistry

Substances

  • Acetonitriles
  • Alcohols
  • Azides
  • Epoxy Compounds
  • Sulfonic Acids
  • Water
  • Carbon
  • Sodium Azide
  • Glycerol
  • acetonitrile