We
present (R)-1,3-butylene carbonate (
R-BC) as a biorenewable monomer for the preparation
of semicrystalline aliphatic polycarbonates. This conversion is achieved
by using enantiomerically pure, biobased (R)-(−)-1,3-butanediol
(bio-BG) as a renewable feedstock. Ring-opening polymerization from
select catalysts at low temperatures can yield regioregular poly((R)-1,3-butylene carbonate) (
R-PBC) with semicrystalline properties (X
reg = > 0.99; T
m = 72 °C). Along
with
the R-enantiomeric polymer, the alternate stereochemical
polymers (using S- and racemic BC) were investigated.
Our analysis shows that the highest level of crystallinity is achieved
with regioregular, biobased
R
-PBC compared to the petrol-based S- and racemic
congeners. This work shows the potential of stereochemically pure
bio-BG as a starting material for semicrystalline, aliphatic carbonates
when high regioregularity is achieved in the polymer microstructure.
The synthesis and thermal characterization of regioregular butylene
carbonate polymers are described in detail.
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