Open Access Peer-reviewed

Separation of the Enantiomers of Lactide, Lactic Acid Dimer, for a Sustainable Bioplastic Management

Nathalie Berezina1,, Nicolas Landercy1, Pierre-Antoine Mariage2, 3, Benoit Morea2

1Green Chemistry Department, Materia Nova R&D Center, Ghislenghien, Belgium

2R&D Department, Galactic SA, Escanaffles, Belgium

3R&D Department, Green2Chem, Leuze, Belgium

World Journal of Organic Chemistry. 2013, 1(2), 20-23. DOI: 10.12691/wjoc-1-2-3
Published online: August 25, 2017

Abstract

Despite the small difference in the steric hindrance of the substitutes of the asymmetric carbon of the lactic acid, a way for the desymmetrization of the racemic mixture was discovered. Two possibilities have arisen: the synthesis and further separation of diastereoisomers with the (S)-2-methyl-1-butanol as chiral auxiliary and the kinetic discrimination during the esterification with the (R)-(-)-Myrtenol.

Keywords:

lactide, enantiomeric separation, diastereoisomers, PLA, bioplastics
[1]  Wee, Y. J., Kim, J. N. and Ryu, H. W., “Biotechnological production of lactic acid and its recent applications”, Food Technol. Biotechnol., 44, 163-172, 2006.
 
[2]  Sauer, M., Porro, D., Mattanovich, D., Branduardi, P., “Microbial production of organic acids: expanding the markets”, Trends Biotechnol., 26, 100-108, 2008.View Article  PubMed
 
[3]  Lunt, J., “Large-scale production, properties and commercial applications of polylactic acid polymers”, Polym. Degrad. Stab., 59, 145-152, 1998.View Article
 
[4]  Dorgan, J. R., Lehermeier, H., Mang, M., “Thermal and rheological properties of commercial-grade poly(lactic acid)s”, J. Polym. Eviron., 8, 1-9, 2000.View Article
 
[5]  Nagasawa, N., Ayako, A., Kanazawa, S., Yagi, T., Mitomo, H., Yoshii, F., Tamada, M., “Application of poly(lactic acid) modified by radiation crosslinking”, Nucl. Instr. Meth. Phys. Res. B, 236, 611-616, 2005.View Article
 
[6]  Yang, F., Murugan, R., Wang, S., Ramakrishna, S., “Electrospinning of nano/micro scale poly(L-lactic acid) aligned fibers and their potential in neural tissue engineering”, Biomaterials, 26, 2603-2610, 2005.View Article  PubMed
 
[7]  Okamoto, K., Toshima K., Matsumura, S., “Degradation of poly(lactic acid) into polymerizable oligomer using montmorillonite K10 for chemical recycling”, Macromol. Biosci., 5, 813-820, 2005.View Article  PubMed
 
[8]  Tsukegi, T., Motoyama, T., Shirai, Y., Nishida, H., Endo, T., “Racemization behaviour of L,L-lactide during heating”, Polym. Degrad. Stab., 92, 552-559, 2007.View Article
 
[9]  Motoyama, T., Tsukegi, T., Shitai, Y., Nishida, H., Endo, T., “Effects of MgO catalyst on depolymerization of poly-L-lactic acid to L,L-lactide”, Polym. Degrad. Stab., 92, 1350-1358, 2007.View Article
 
[10]  Tsuji, H., Ikada, Y., “Stereocomplex formation between enantiomeric poly (lactic acid)s. XI. Mechanical properties and morphology of solution-cast films”, Polymer, 40, 6699-6708, 1999.View Article
 
[11]  Gao, C., Qiu, J., Li, J., Ma, C., Tang, H., Xu, P., “Enantioselective oxidation of racemic lactic acid to D-lactic acid and pyruvic acid by Pseudomonas stutzeri SDM”, Bioresour. Technol., 100, 1878-1880, 2009.View Article  PubMed
 
[12]  Ma, C. Gao, J. Qiu, J. Hao, W. Liu, A. Wang, Y. Zhang, M. Wang and P. Xu, Appl. Microbiol. Biotechnol., 2007, 77, 91.View Article  PubMed
 
[13]  Martin-Matute, B., Backvall, J. E., Organic Synthesis with Enzymes in Non-Aqeous Media, Wiley-VCH, Weinheim, 2008, 113-144.View Article
 
[14]  Inaba, C., Maekawa, K., Morisaka, H., Kuroda K., Ueda, M., “Efficient synthesis of enantiomeric ethyl lactate by Candida antarctica lipase B (CALB)-displaying yeasts”, Appl Microbiol Biotechnol., 83, 859-864, 2009.View Article  PubMed