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Designed for Molecular Recycling: A Lignin-Derived Semi-aromatic Biobased Polymer

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Polyalkylenehydroxybenzoates (PAHBs): biorenewable aromatic/aliphatic polyesters from lignin.

Laurent Mialon¹, Rob Vanderhenst, Alexander G Pemba

¹The George and Josephine Butler Polymer Research Laboratory, Department of Chemistry, University of Florida, Gainesville, Florida 32611-7200, USA.

Macromolecular Rapid Communications

|July 30, 2011

Summary

New biorenewable polyesters, polyalkylenehydroxybenzoates (PAHBs), were synthesized from lignin derivatives. These novel aromatic/aliphatic polyesters offer tunable thermal properties for potential material applications.

Keywords:

degradable polymers lignin polyesters sustainable polymers vanillin

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Area of Science:

Polymer Chemistry
Materials Science
Biorenewable Resources

Background:

Polyalkylenehydroxybenzoates (PAHBs) represent a novel class of thermoplastic, biorenewable aromatic/aliphatic polyesters.
PAHBs are synthesized from readily available lignin-derived aromatic acids, including 4-hydroxybenzoic acid, vanillic acid, and syringic acid.

Purpose of the Study:

To synthesize and characterize a new family of biorenewable polyesters, PAHBs.
To investigate the synthesis of PAHBs from various lignin-derived aromatic precursors.
To evaluate the thermal properties of the synthesized PAHBs.

Main Methods:

Synthesis of hydroxy-acid monomers via alkylation of lignin-derived acids with chloroalkanols.
Polyesterification of monomers under dynamic vacuum at elevated temperatures (150–250°C) using antimony trioxide (Sb2O3) catalyst.
Characterization of synthesized polyesters using differential scanning calorimetry (DSC) and thermogravimetric analysis (TGA).

Main Results:

Successful synthesis of polyalkylene 4-hydroxybenzoates, polyalkylene vanillates, and polyalkylene syringates.
Demonstration of polyesterification under dynamic vacuum conditions with a 1 mol% Sb2O3 catalyst.
Comparative analysis of the thermal properties of the synthesized PAHBs using DSC and TGA.

Conclusions:

PAHBs can be effectively synthesized from biorenewable aromatic precursors.
The developed synthetic route allows for the preparation of a range of PAHBs with tunable properties.
The thermal properties of these novel biorenewable polyesters warrant further investigation for material applications.