Journal of Polymer Science Part A: Polymer Chemistry, Vol.44, No.18, 5247-5253, 2006
Direct dehydration polycondensation of lactic acid catalyzed by water-stable Lewis acids
Poly(L-lactic acid) (PLLA) is generally produced by ring-opening polymerization of (S,S)-lactide, which is prepared from dehydration polycondensation of lactic acid and successive depolymerization. Results of this study show that scandium trifluoromethanesulfonate [Sc(OTf)(3)] and scandium trifluoromethanesulfonimide [Sc(NTf2)(3)] are effective for one-step dehydration polycondensation of L-lactic acid. Bulk polycondensation of L-lactic acid was carried out at 130-170 degrees C to give PLLA with M-n of 5.1 X 10(4) to 7.3 x 10(4) (yield 32-60%). The solution polycondensation was performed at 135 degrees C for 48 h to afford PLLA with M-n of 1.1 X 10(4) with good yield (90%). In no case did H-1 NMR, specific optical rotation, or DSC measurement confirm racemizations. The catalyst was recovered easily by extraction with water and reused for polycondensation. (c) 2006 Wiley Periodicals, Inc.
Keywords:dehydration polycondensation;lactic acid;one-step synthesis;recycled catalyst;scandium trifluoromethanesulfonate [Sc(OTf)(3)];scandium trifluoromethanesulfonimide [Sc(NTf2)(3)]