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Polylactones 48. SnOct2-Initiated Polymerizations of Lactide: A Mechanistic Study

Kricheldorf, Hans R., Kreiser-Saunders, Ingrid, Stricker, Andrea·2000·Macromolecules
DOI 10.1021/ma991181w
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Abstract

Sn(II)2−ethylhexanoate (SnOct 2 ) was reacted with 2 equiv of benzyl alcohol at 20 °C, and a liberation of octanoic acid in a rapid equilibration was found. When the temperature was raised to 180 °C in steps of 40 °C, esterification of benzyl alcohol and octanoic acid was observed up to a conversion of 90%. This esterification was catalyzed by Sn(II) and not by the protons of the free octanoic acid. The esterification liberated Sn(OH) 2, which finally precipitated in the form of SnO. This precipitate proved to be a good initiator for the polymerization of lactide above 120 °C. Analogous results were obtained with 1-decanol, triethylene glycol monomethyl ether, and neopentane diol. When SnOct 2 was reacted with methyl lactate at 20 °C, a chelate complex of one Sn with two lactate ligands was formed, liberating almost all octanoic acid. At higher temperatures, esterification of octanoic acid with methyl lactate and transesterification of the methyl group (yielding methyl octoate) were observed. The latter esterification was predominant at higher temperatures, and a Sn lactate (1:1) complex precipitated under all circumstances. This complex proved to be an initiator for polymerizations of l -lactide. Polymerization of l -lactide initiated with neat SnOct 2 at 180 °C yielded polylactides having octanoate end groups, and the molecular weights paralleled the monomer/initiator ratio.

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Citations

Cites

Research works printed but not linked: 27

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Metadata

Authors
Kricheldorf, H. R., Kreiser-Saunders, I., & Stricker, A.
Affiliations
Institut für Technische Makromolekulare Chemie, Bundesstrasse 45, D-20146 Hamburg, Germany
Venue
Macromolecules
Publisher
American Chemical Society (ACS)
Published
2000-01-14
Volume
33
Issue
3
Pages
702-709
ISSN
  • 0024-9297
  • 1520-5835
DOI
10.1021/ma991181w
Cited by
467
References
1
Language
en

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