Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 16, Issue 46, Pages 13805-13813Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201001111
Keywords
carbonates; organocatalysis; polycarbonates; ring-opening polymerization; trimethylene carbonate
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Funding
- Total Petrochemicals Co.
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Six-membered cyclic carbonates, namely trimethylene carbonate (TMC), 3,3-dimethoxytrimethylene carbonate (DMTMC) and 3-benzyloxytrimethylene carbonate (BTMC), undergo controlled immortal ring-opening polymerization (iROP) under mild conditions (bulk, 60-150 degrees C), by using organocatalysts, including an amine [4-N, N-dimethylaminopyridine (DMAP)], a guanidine [1,5,7-triazabicyclo-[4.4.0]dec-5-ene (TBD)], or a phosphazene [2-tert-butylimino-2-diethylamino-1,3-dimethylperhydro-1,3,2-diazaphosphorine (BEMP)], in the presence of an alcohol [benzyl alcohol (BnOH), 1,3-propanediol (PPD), glycerol (GLY)] that acts as both a co-initiator and a chain-transfer agent. Remarkably, such organocatalysts remain highly active in the iROP of technical-grade, unpurified TMC. Under optimized conditions, as much as 100 000 equivalents of TMC were fully converted by as little as 10 ppm of BEMP with the simultaneous growth of as many as 200 polymer chains, allowing the preparation of high molar mass poly(trimethylene carbonate)s (up to 45800 gmol(-1)). These catalyst systems enable among the highest activities (TOF=55800 h(-1)) and productivities (TON=95000) ever reported for the ROP of TMC.
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