Glycerol esters from the reaction of glycerol with dicarboxylic acid esters

Mono- and di-esterified glycerols were synthesized by the base catalyzed reaction of glycerol with aliphatic dicarboxylic acid esters (C-2-C-9): 2,3-dihydroxy-propyl oxalate (2), 1,3 dioxalyloxy propan-2-ol (3), 1,3-dimethoxyoxalyloxy propan-2-ol (5), 2,3-dihydroxy-propyl malonate (6), 2,3-dihydroxy-propyl methyl malonate (7), 2,3-dihydroxy-propyl methyl succinate (8), 1,3-dimethoxysuccinyloxy propan-2-ol (9), 2,3-dihydroxy-propyl methyl glutarate (10), 1,3-dimethoxyglutaryloxy propan-2-ol (11), 2,3-dihydroxy-propyl methyl azelate (14), and 1,3-dimethoxyazelyloxy propan-2-ol (15). Their structures were elucidated by spectrometric methods. Compounds 8, 10, 2,3-dihydroxy-propl methyl adipate (12) and 14 were found to possess surface active properties and the ability to reduce the interfacial tension between paraffin and water.