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Issue 31, 2013
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Single-site bismuth alkoxide catalysts for the ring-opening polymerization of lactide

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Abstract

Salen bismuth alkoxides, where the salen ligand contains 2,4-di-tert-butylphenoxy groups and one of ethylene, cyclohexane or ortho-phenyl as a backbone have been prepared from reactions involving Bi[N(SiMe3)2]3 and the free salen ligand followed by alcoholysis (ButOH, PriOH and 2,6-But2C6H3OH). The molecular structures of the salen ligand with the cyclohexyl back-bone have been determined for the complexes salenBiCl and salenBiOC6H3-2,6-But2. The chloro compound is a dimer with chloride bridges while the phenoxide is monomeric with an unusually distorted five-coordinate geometry. The phenoxide and tert-butoxide complexes have been employed in the ring-opening polymerization of lactides (L- and rac-) to give polylactides, PLAs. With rac-LA heterotactic PLA is formed preferentially, Pr = ∼0.9, in dichloromethane or toluene at room temperature. The reaction is first order in [Bi] and is notably faster than most aluminum and zinc initiators as well as tin(II) octanoate. These results are discussed in terms of a recent report on the polymerization of LA by Peptobismol® and bismuth subsalicylate.

Graphical abstract: Single-site bismuth alkoxide catalysts for the ring-opening polymerization of lactide

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Publication details

The article was received on 06 Mar 2013, accepted on 15 Jun 2013 and first published on 17 Jun 2013


Article type: Paper
DOI: 10.1039/C3DT50629K
Citation: Dalton Trans., 2013,42, 11234-11241
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    Single-site bismuth alkoxide catalysts for the ring-opening polymerization of lactide

    V. Balasanthiran, M. H. Chisholm, C. B. Durr and J. C. Gallucci, Dalton Trans., 2013, 42, 11234
    DOI: 10.1039/C3DT50629K

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