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Oxazolidinones have been synthesized by reacting glycerol carbonate or glycerol with urea in the presence of gamma-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. Copyright
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Reference：
Oxazolidine – Wikipedia,
Oxazolidine | C3H1305NO – PubChem