Glycerol functionalized imidazolium tri-cationic room temperature ionic liquids: Synthesis, properties and catalytic performance for 2-azidoalcohol synthesis from epoxide

Imidazolium based tri-cationic room temperature ionic liquid (RTILs) were synthesized and characterized, and their physicochemical properties such as thermal stability, viscosities and solubility were investigated. These ionic liquids exhibited excellent catalytic activity for 2-azidoalcohol synthesis from epoxide and sodium azide. The present tri-cationic RTILs/water catalytic systems showed better catalytic performance than their mono-cationic counterparts. Among all prepared ionic liquids, [GLY(mim)(3)][OMs] gave best results with up to 96% yield of 2-azidoalcohol. The reusability test of glycerol-tri (3-methylimidazolium) trimesylate [GLY(mim)(3)][OMs](3) were studied for five consecutive cycles presenting the highest yield without loss in their catalytic activity. Hence, the experimental results demonstrated that structural variation of synthesized tri-cationic RTILs can dictate their physicochemical and catalytic activities. (C) 2015 Elsevier B.V. All rights reserved.