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Macromolecular Research

, Volume 14, Issue 5, pp 510–516 | Cite as

Synthesis of lactide from oligomeric PLA: Effects of temperature, pressure, and catalyst

  • Dong Keun Yoo
  • Dukjoon Kim
  • Doo Sung Lee
Article

Abstract

Lactide was produced from oligomeric PLA by back-biting reaction of the OH end groups. For optimization of the reaction conditions, the effects of temperature, pressure, PLA molecular weight, and catalyst type on the lactide synthesis were examined. The fraction of D,L-lactide decreased with increasing temperature. Among the various Sn-based catalysts, the D,L-lactide fraction was maximized when SnO was used. A higher yield with lower racemization was observed at lower pressure. The conversion of PLA was maximized at an oligomeric PLA molecular weight of ca. 1380. The yield of lactide increased but the fraction of D,L-lactide decreased with increasing molecular weight. The highest conversion with the lowest racemization degree was obtained at a catalyst concentration of 0.1 wt%. The lactide was more sensitive to racemization because of the entropic effect.

Keywords

poly(lactic acid) D,L-lactide meso-lactide catalysts depolymerization racemization deprotonation 

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References

  1. (1).
    P. Mainilvarlet, R. Rahm, and S. Gogolewski,Biomaterials,18, 257 (1997).CrossRefGoogle Scholar
  2. (2).
    W. Hoogsteen, A. R. Postema, A. J. Pennings, and G. T. Brinke,Macromolecules,23, 634 (1990).CrossRefGoogle Scholar
  3. (3).
    C. Bastioli,Macromol. Symp.,135, 193 (1998).CrossRefGoogle Scholar
  4. (4).
    K.W. Kim and S. I. Woo,Macromol. Chem. Phys.,203, 2245 (2002).CrossRefGoogle Scholar
  5. (5).
    S. I. Moon, C. H. Lee, M. Miyamoto, and Y. Kimura,J. Polym. Sci.: Part A; Polym. Chem.,38, 1673 (2000).CrossRefGoogle Scholar
  6. (6).
    K. Yamane,et al., USP 6916939 (2005).Google Scholar
  7. (7).
    F. E. Kohn, J. W. A. Van Den Berg, V. D. Ridder, and J. Feijen,J. Appl. Polym. Sci.,29, 4265 (1984).CrossRefGoogle Scholar
  8. (8).
    G.. I. Shim, J. H. Kim, S. H. Kim, and Y. H. Kim,Korea Polym. J.,5, 19 (1997).Google Scholar
  9. (9).
    A. J. Nijenhuis, D. W. Grijpma, and A. J. Pennings,Macromolecules,25, 6419 (1992).CrossRefGoogle Scholar
  10. (10).
    J. Zhang, Z. Gan, Z. Zhong, and X. Jing,Polym. Int.,45, 60 (1998).CrossRefGoogle Scholar
  11. (11).
    K. A. M. Thakur, R. T. Kean, E. S. Hall, J. J. Kolstad, T. A. Lidgren, M. A. Doscotch, J. I. Siepmann, and E. J. Munson,Macromolecules,30, 2422 (1997).CrossRefGoogle Scholar
  12. (12).
    K. A. M. Thakur, R. T. Kean, and E. S. Hall,Anal.Chem.,69, 4303 (1997).CrossRefGoogle Scholar
  13. (13).
    P. R. Gruber,et al., USP 2574073 (1993).Google Scholar
  14. (14).
    H. R. Kricheldorf and A. Serra,Polym. Bull.,14, 497 (1985).CrossRefGoogle Scholar
  15. (15).
    H. R. Kricheldorf and M. Sumbel,Eur. Polym. J.,25, 585 (1989).CrossRefGoogle Scholar
  16. (16).
    D. R. Witzke, R. Narayan, and J. J. Kolstad,Macromolecules,30, 7075 (1997).CrossRefGoogle Scholar
  17. (17).
    H. R. Kricheldorf and S. R. Lee,Polymer,36, 2995 (1995).CrossRefGoogle Scholar
  18. (18).
    D. K. Yoo, D. S. Lee, and D. Kim,Macromol. Res.,13, 68 (2005).CrossRefGoogle Scholar
  19. (19).
    H. P. Benecke,et al., USP5332839 (1994).Google Scholar
  20. (20).
    M. Muller,et al., USP 5214159 (1993).Google Scholar
  21. (21).
    H. R. Kricheldorf and I. Kreiser-Saunders,Macromol. Chem.,191, 1057 (1990).CrossRefGoogle Scholar
  22. (22).
    H. R. Kricheldorf, I. Kreiser-Saunders, and C. Boettcher,Polymer,36, 1253 (1995).CrossRefGoogle Scholar
  23. (23).
    H. R. Kricheldorf and D.-O. Damaru,Macromol. Chem.,198, 1753 (1997).CrossRefGoogle Scholar
  24. (24).
    H. Tsuji, I. Fukui, H. Daimon, and K. Fujie,Polym. Degrad. Stabil.,81, 501 (2003).CrossRefGoogle Scholar

Copyright information

© The Polymer Society of Korea and Springer 2006

Authors and Affiliations

  1. 1.Department of Chemical Engineering, Polymer Technology InstituteSungkyunkwan University SuwonGyeonggiKorea
  2. 2.Department of Polymer Engineering, Polymer Technology InstituteSungkyunkwan UniversitySuwon, GyeonggiKorea

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