Cyclic Polyester Formation with an [OSSO]‐Type Iron(III) Catalyst

The efficient formation of cyclic polyesters from the ring‐opening polymerization of lactide, ϵ‐caprolactone, and β‐butyrolactone catalyzed by a 1,4‐dithiabutanedyl‐2,2′‐bis(4,6‐dicumylphenol) [OSSO]‐FeCl complex activated with cyclohexene oxide was achieved. The catalyst was very active (initial tu...

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Bibliographic Details
Published in:ChemSusChem 2020-01, Vol.13 (1), p.141-145
Main Authors: Impemba, Salvatore, Della Monica, Francesco, Grassi, Alfonso, Capacchione, Carmine, Milione, Stefano
Format: Article
Language:English
Subjects:
Butyrolactone
Catalysts
cyclization
Cyclohexene
homogeneous catalysis
Iron
Polyester resins
Polymerization
polymers
Ring opening polymerization
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Summary:The efficient formation of cyclic polyesters from the ring‐opening polymerization of lactide, ϵ‐caprolactone, and β‐butyrolactone catalyzed by a 1,4‐dithiabutanedyl‐2,2′‐bis(4,6‐dicumylphenol) [OSSO]‐FeCl complex activated with cyclohexene oxide was achieved. The catalyst was very active (initial turnover frequency up to 2718 h−1), robust, and worked with a monomer/Fe ratio up to 10 000. The formation of cyclic polymers was supported by using high‐resolution matrix‐assisted laser desorption ionization (MALDI) MS, and the average ring size (≈5 kDa for cyclic polylactide) independent of the reaction conditions. A monometallic ring‐opening polymerization/cyclization mechanism was proposed from the results of a kinetic investigation. Squaring the cycle: Cyclic polyesters are prepared selectively from cyclic esters by a ring‐opening polymerization/cyclization reaction catalyzed by a highly active (initial turnover frequency=2700 h−1) and robust (turnover number=10 000) [OSSO]‐type FeIII complex.
ISSN:1864-5631
1864-564X
DOI:10.1002/cssc.201902163