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Sustainable Synthesis and Polycondensation of Levoglucosenone‐Cyrene‐Based Bicyclic Diol Monomer: Access to Renewable Polyesters
Author(s) -
DiotNéant Florian,
Mouterde Louis,
Fadlallah Sami,
Miller Stephen A.,
Allais Florent
Publication year - 2020
Publication title -
chemsuschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 2.412
H-Index - 157
eISSN - 1864-564X
pISSN - 1864-5631
DOI - 10.1002/cssc.202000680
Subject(s) - diol , chemistry , polyester , condensation polymer , monomer , thermostability , organic chemistry , bicyclic molecule , catalysis , green chemistry , solvent , polymer chemistry , reaction mechanism , polymer , enzyme
The already‐reported, low‐yielding, and non‐sustainable Et 3 N‐mediated homocoupling of levoglucosenone (LGO) into the corresponding LGO‐Cyrene TM diketone has been revisited and greened‐up. The use of methanol as both a renewable solvent and catalyst and K 2 CO 3 as a safe inorganic base improved the reaction significantly with regards to yield, purification, and green aspects. LGO‐Cyrene TM was then subjected to a one‐pot, H 2 O 2 ‐mediated Baeyer–Villiger oxidation/rearrangement followed by an acidic hydrolysis to produce a new sterically hindered bicyclic monomer, 2H‐HBO‐HBO. This diol was further polymerized in bulk with diacyl chlorides to access new promising renewable polyesters that exhibit glass transition temperatures ( T g ) from −1 to 81 °C and a good thermostability with a temperature at which 50 % of the mass is lost ( T d50 % ) of 349–406 °C.