Direct polycondensation of L-lactic acid in hydrophobic bis (trifluoromethanesulfonyl)imide-anionic ionic liquids: A kinetic study

Ionic liquids (ILs), instead of the classical organic solvents, have shown great improvements in chemical processes. Herein, Water-insoluble alkyl- and benzyl-substituted imidazolium bis(trifluoromethanesulfonyl)imides as non-volatile and thermostable solvents were employed in the direct polycondensation of L-lactic acid (LLA). The effects of monomer concentration, reaction temperature and miscibility between the ILs and poly(L-lactic acid) (PLLA) were comprehensively investigated. Biodegradable PLLA with weight-average molecular weight as high as 132 kDa was synthesized. Compared to melt-polycondensation of LLA, far higher molecular weight could be achieved via the solution polycondensation of LLA in ILs since the viscosity of the polymer melt could be significantly reduced based on the dilution effect of ILs. Polycondensation kinetics of LLA in bulk and in an IL demonstrated that the IL could accelerate the polycondensation of LLA. Influence of lactide, the main by-product, on the polycondensations of LLA was also studied kinetically.

Automated summary

This study demonstrates the use of ionic liquids as solvents for the synthesis of biodegradable poly(lactic acid) with high molecular weight, and investigates the factors and kinetics involved in the preparation process. The results show that ionic liquids can effectively improve the polycondensation of lactic acid and enhance the performance of the final product.