Urea as an efficient reagent for the synthesis of 3-ethyl-3-(hydroxymethyl)oxetane: A novel component in cationic ring-opening polymerisation
Urea is a very attractive chemical raw material for large-scale production as it combines low cost with virtually unlimited supply and essentially no toxic effects. Here, we present a study on its use in the dehydration of trimethylolpropane with formation of 3-ethyl-3-(hydroxymethyl)oxetane. The reaction consists of carbonylation of trimethylolpropane and subsequent extrusion of carbon dioxide. The first step was run at a temperature of 120-160 °C at a pressure of approximately 300 mmHg for 1-5 h. Most likely, carbamates of TMP constitute the major product. In the latter step, the temperature was increased to 195-215 °C, the pressure was reduced to 10-50 mmHg, and the final product was isolated by distillation. A spiroorthocarbonate of TMP was formed as an unexpected by-product. The process has been demonstrated on a multikilogram scale. Toxicological screening revealed 3-ethyl-3-(hydroxymethyl)oxetane to be irritating to eye but not to skin.
Annby, Ulf,Rehnberg, Nicola,Samuelsson, Jesper,Teichert, Oliver
p. 568 - 571
(2013/09/07)
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