Development of a Solution Synthesis of Poly(Sebacic Anhydride) With the Activating Agent 4-toluenesulfonyl Chloride: Understanding the Effect of Different Bases on the Reaction Products

Author

Patricia PoleyFollow

Date of Thesis

Spring 2023

Description

The overall goal of this honors thesis was to develop a solution synthesis of Poly(Sebacic Anhydride) with the activating agent 4-toluenesulfonyl chloride and understand the effects of varying temperature, bases, and the addition order of reagents on the reaction.

Polyanhydrides are a class of hydrophobic, degradable polymers used in controlled drug delivery for 30 years. They are synthesized through three general methods: melt polycondensation, solution polycondensation, and ring-opening polymerization. Of these three methods, solution polycondensation typically results in products with lower molecular weight. Previous work in the Vogel lab identified two new ways to synthesize anhydrides using solution polycondensation reactions that produced polymers with high molecular weights. During this work, they discovered that when n-methyl imidazole was used as a base, the resulting reaction did not form a polymer but an insoluble salt. We hypothesize that sebacic acid was not a strong enough nucleophile capable of attacking the tosylate/imidazolium acyl salt to drive the reaction.

Although no reaction conditions resulted in the polymerization of sebacic acid into Poly(Sebacic Anhydride), two conditions showed promise for future research by producing anhydride rings: reactions with CaCO₃ and K₂CO₃ or reactions completed at 60 ℃. We also found that adding the sulfonyl chloride before adding the solvent positively affects making anhydride bonds.

Keywords

Polymer Synthesis, Poly(Sebacic Anhydride), Bases, Drug Delivery

Access Type

Honors Thesis

Degree Type

Bachelor of Science in Biomedical Engineering

Major

Biomedical Engineering

Minor, Emphasis, or Concentration

Anthropology

First Advisor

Brandon Vogel

Recommended Citation

Poley, Patricia, "Development of a Solution Synthesis of Poly(Sebacic Anhydride) With the Activating Agent 4-toluenesulfonyl Chloride: Understanding the Effect of Different Bases on the Reaction Products" (2023). Honors Theses. 660.
https://digitalcommons.bucknell.edu/honors_theses/660