Abstract
Enzymatic synthesis of aromatic biobased polyesters is a recent and rapidly expanding research field. However, the direct lipase-catalyzed synthesis of polyesters from ferulic acid has not yet been reported. In this work, various ferulic-based monomers were considered for their capability to undergo CALB-catalyzed polymerization. After conversion into diesters of different lengths, the CALB-catalyzed polymerization of these monomers with 1,4-butanediol resulted in short oligomers with a DPn up to 5. Hydrogenation of the double bond resulted in monomers allowing obtaining polyesters of higher molar masses with DPn up to 58 and Mw up to 33,100 g·mol−1. These polyesters presented good thermal resistance up to 350 °C and Tg up to 7 °C. Reduction of the ferulic-based diesters into diols allowed preserving the double bond and synthesizing polyesters with a DPn up to 19 and Mw up to 15,500 g·mol−1 and higher Tg (up to 21 °C). Thus, this study has shown that the monomer hydrogenation strategy proved to be the most promising route to achieve ferulic-based polyester chains of high DPn. This study also demonstrates for the first time that ferulic-based diols allow the synthesis of high Tg polyesters. Therefore, this is an important first step toward the synthesis of competitive biobased aromatic polyesters by enzymatic catalysis.
Highlights
The current environmental issues are directing research toward the production of greener materials through a more environmentally friendly processes
This study demonstrates for the first time that ferulic-based diols allow the synthesis of high Tg polyesters
Lipase B from Candida antarctica immobilized on acrylic resin (activity measured to 11,000 PLU/g) (CALB), deuterated chloroform (CDCl3), dibutyl aluminum hydride (DIBAL-H) solution in toluene (25 wt %), and palladium on activated charcoal (Pd/C) were supplied by Sigma-Aldrich (Saint-Louis, MO, USA)
Summary
The current environmental issues are directing research toward the production of greener materials through a more environmentally friendly processes. This trend is important in the field of polyesters. The vast majority of polyesters are fossil-based, often show poor biodegradability, and are synthesized through harsh reaction conditions [1]. For this reason, biobased polymers are gaining much attention. Such polymers are produced from a renewable feedstock [2,3] and can sometimes present good biodegradability [4]. To their oil-based counterparts, these biobased polymers are generally synthesized at high temperatures by employing potentially hazardous organometallic catalysts [5]
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