The polycondensation of glycerol and aliphatic dicarboxylic
acids
catalyzed by Candida antarctica lipase
B absorbed on a macroporous acrylic resin (CALB) results in polyesters
composed of repetitive units structurally similar to mono-, di-, and
triglycerides. Adipic, suberic, sebacic, and dodecanedioic acids were
investigated for the CALB-catalyzed polycondensation with glycerol
in solution and bulk. In both conditions, the CALB-catalyzed esterification
of primary hydroxyl of glycerol and acyl migration occurs in parallel
and results in branched polyesters. Higher molar mass polyesters were
obtained in reactions performed in bulk and using longer diacids than
in solution and using shorter diacids. These glyceride-like polyesters
have different amphiphilicity and physical properties that change
from more hydrophilic and amorphous for poly(glycerol adipate) to
more hydrophobic and semicrystalline for poly(glycerol dodecanedioate).
The amphiphilicity of these polyesters allowed the production of nanoparticles
with a hydrodynamic radius in the range of 35–270 nm and a
negative zeta potential.