Preparation of aliphatic poly(thioester) by the lipase-catalyzed direct polycondensation of 11-mercaptoundecanoic acid.
An aliphatic polythioester was enzymatically prepared by the direct polycondensation of mercaptoalkanoic acid using immobilized lipase of Candida antarctica (lipase CA) in bulk. The commercially available 11-mercaptoundecanoic acid was polymerized by lipase CA in bulk in the presence of molecular sieves 4A as a water absorbent at 110 degrees C for 48 h to produce poly(11-mercaptoundecanoate) with an M(w) of 34 000 in high yield. The 104.5 degrees C melting temperature (T(m)) of poly(11-mercaptoundecanoate) was about 20 degrees C higher than that of the corresponding polyoxyester, poly(11-hydroxyundecanoate). The polythioester was readily transformed by lipase into the corresponding cyclic oligomers mainly consisting of the dimer, which were readily repolymerized by the ring-opening polymerization using lipase as a sustainable chemical recycling.
Kato
Makoto
M
Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi, Kohoku-ku, Yokohama 223-8522, Japan.
Toshima
Kazunobu
K
Matsumura
Shuichi
S
D002175:Candida / Q000201:enzymology; D002384:Catalysis; D005227:Fatty Acids / Q000737:chemistry*; D008049:Lipase / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D011091:Polyesters / Q000737:chemistry; D019032:Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization; D013438:Sulfhydryl Compounds / Q000737:chemistry*
C505222:11-mercaptoundecanoic acid; D005227:Fatty Acids; D011091:Polyesters; D013438:Sulfhydryl Compounds; D008049:Lipase