Catalytic synthesis of hydroxymethyl-2-oxazolidinones from glycerol or glycerol carbonate and urea

Angela Dibenedetto, Francesco Nocito, Antonella Angelini, Imre Papai, Michele Aresta, Raffaella Mancuso

Research output: Contribution to journalArticle

18 Citations (Scopus)

Abstract

Oxazolidinones have been synthesized by reacting glycerol carbonate or glycerol with urea in the presence of γ-Zr phosphate as a catalyst. The conversion yield of the polyol or its carbonate depends on the temperature. Below 408 K the selectivity is 100 % with a conversion of up to 25 %, whereas increasing the temperature means that conversion yield grows, but the selectivity decreases, which makes the separation process more difficult. Starting from glycerol carbonate, two isomers, 6 and 6′, are formed with a quasi 1:1 molar ratio because urea can attack the carbonate moiety on both sides of the carboxylic CO moiety. From glycerol the formation of the 6′ isomer is preferred: the ratio of 6′/6 is close to 7. The oxazolidinones formed act as templates because they interact through hydrogen bonding with glycerol. The intensity of the interaction depends on the 6 or 6′ isomer: DFT calculations showed that the energy was 22.6 kcal mol-1 for 6-oxazolidinone and 25.7 kcal mol-1 for 6′-oxazolidinone.

Original languageEnglish
Pages (from-to)345-352
Number of pages8
JournalChemSusChem
Volume6
Issue number2
DOIs
Publication statusPublished - Feb 1 2013

Keywords

  • glycerol
  • homogeneous catalysis
  • hydrogen bonds
  • oxazolidinones
  • zirconium

ASJC Scopus subject areas

  • Environmental Chemistry
  • Chemical Engineering(all)
  • Materials Science(all)
  • Energy(all)

Fingerprint Dive into the research topics of 'Catalytic synthesis of hydroxymethyl-2-oxazolidinones from glycerol or glycerol carbonate and urea'. Together they form a unique fingerprint.

  • Cite this