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Polycarbonates from the polyhydroxy natural product quinic acid.

Céline J Besset1, Alexander T Lonnecker, Jennifer M Streff

  • 1Department of Chemistry, Texas A&M University , P.O. Box 30012, College Station, Texas 77842-3012, USA.

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|June 8, 2011
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Summary

Biosourced polycarbonates from quinic acid were synthesized with high glass-transition temperatures. Deprotection strategies were explored, but complete removal of protecting groups led to polymer degradation and reduced thermal stability.

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Area of Science:

  • Polymer Chemistry
  • Materials Science
  • Organic Synthesis

Background:

  • Development of sustainable, bio-based polymers is crucial for reducing reliance on fossil fuels.
  • Quinic acid, a naturally abundant polyhydroxy compound, offers a promising renewable platform for polymer synthesis.
  • Challenges exist in controlling regioselectivity and achieving efficient polymerization and deprotection of quinic acid derivatives.

Purpose of the Study:

  • To develop strategies for synthesizing biosourced polycarbonates from quinic acid.
  • To investigate the copolymerization of protected quinic acid diol monomers with phosgene.
  • To evaluate the thermal properties and deprotection behavior of the resulting polycarbonates.

Main Methods:

  • Regioselective protection of quinic acid diols using tert-butyldimethylsilyl (TBS) groups.
  • Copolymerization of protected quinic acid diols with phosgene (generated in situ).
  • Size exclusion chromatography (SEC) for molecular weight determination and differential scanning calorimetry (DSC) for thermal analysis.

Main Results:

  • Protected poly(1,4-quinic acid carbonate) and poly(1,5-quinic acid carbonate) were synthesized with molecular weights up to 7.6 kDa.
  • High glass-transition temperatures (Tg) were observed: 209 °C for the 1,4-isomer and 229 °C for the 1,5-isomer.
  • Deprotection under mild conditions resulted in increased Tg upon partial removal of TBS groups, but full deprotection led to polymer degradation.

Conclusions:

  • Biosourced polycarbonates from quinic acid exhibit promising high thermal stability due to their bicyclic structure.
  • Regiochemistry significantly influences polymer properties, with the 1,5-isomer showing higher Tg and lower deprotection reactivity.
  • Achieving complete deprotection without compromising polymer integrity remains a challenge for these materials.