Green chemistry aims to mitigate the environmental, health, and economic concerns associated with traditional chemical processes by increasing reaction efficiencies, reducing waste, using innocuous materials, and developing biodegradable products. Poly(anhydride-esters) (PAEs) are biodegradable surface-eroding polymers that represent such products, exhibiting a controlled, near zero-order release of naturally occurring bioactives, including salicylic acid (SA) and ferulic acid (FA), which are used in biomedical and personal care applications. Currently, the synthesis of bioactive-based PAEs uses excessive solvents, hazardous purification chemicals, and multistep reactions, all of which can be improved upon using green chemistry principles. To improve upon this, SA- and FA-based PAE monomers were synthesized via a one-pot methodology that requires minimal purification and drastically reduces reaction time. For instance, SA-based PAEs were synthesized via solvent free methods by linking two SA moieties with an acyl chloride to form an SA diacid within minutes, which can be activated and subsequently polymerized under high vacuum and heat to form product. Products were then purified using nontoxic and environmentally safe solvents.  Polymers and their precursors were then characterized to ensure the greener methodology did not have a detrimental influence on physiochemical and thermal properties. Similar methodologies were explored to synthesize and characterize FA-based PAEs.  Through our green synthetic methods we hope to reduce PAEs' environmental impact and move towards a more economical and sustainable future.

Exploring green methods through a one-pot salicylic acid-based poly(anhydride-ester) synthesis

248th National Meeting (2014)

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