Synthesis, characterization and reactivity of a six-membered cyclic glycerol carbonate bearing a free hydroxyl group

Abstract

For the first time, synthesis of the simplest derivative of glycerol, a six-membered cyclic glycerol carbonate (5-hydroxy-1,3-dioxan-2-one), from glycerol is presented.

Benefit of the Reactive Extrusion in the Course of Polyhydroxyurethanes Synthesis by Aminolysis of Cyclic Carbonates

“…[10][11][12][13] Most of the cyclic carbonates developed to form PHUs are 5membered cyclic carbonates, 5-CCs. [13][14][15][16][17][18] In a lesser extent, some PHUs can be also prepared from 6-to 8-membered cyclic carbonates [19][20][21][22][23][24][25][26] . These larger carbonate rings exhibit a higher reactivity in comparison to the 5-CCs, due to their higher ring strain, but suffer from a lower stability at storage.…”

Activated Glycerol Carbonates, Versatile Reagents with Aliphatic Amines: Formation and Reactivity of Glycidyl Carbamates and Trialkylamines

“…Glycosylation has also been performed on glycerol carbonate by applying Ferrier conditions on glucal . 1,3‐GC also proved to be a useful synthon for fine chemistry but, while 1,2‐GC is easily prepared, its 1,3‐isomer needs a sequential approach . Activation with sulfonylated groups leads to two main derivatives, tosylated glycerol carbonate 1 (TGC) and mesylated glycerol carbonate 2 (MGC) .…”

A Robust and Scalable Continuous Flow Process for Glycerol Carbonate

“…It should be noted that, potentially, glycerol can be derivatized to form different isomers involving either a five‐ or a six‐membered cyclic carbonate. The five‐membered derivative is the kinetic product while under alternative reaction conditions the six‐membered cyclic glycerol carbonate (3‐GLC, 5‐hydroxy‐1,3‐dioxan‐2‐one, glycerol 1,3‐carbonate) can be prepared as the thermodynamic product . Intrigued by the initial results generated by the ammonium catalyst, a selection of related catalysts was also examined for the transformation (Tab.…”