Abstract

Phosphorus extrusion is the process of removing the phosphorus ion from a molecule specifically a phosphonium salt. Currently many phosphorus extrusion methods are harsh for the environment because they require the addition of strong acids, strong bases, oxidation reagents, or heating the reaction to extremely high temperatures. In this thesis, mild phosphorus extrusion conditions were used to synthesize 2,2’-bipyridine from diphenyldi(2-pyridyl)phosphonium bromide ([Dipyphos]Br). The main goal is to increase bipy yield while decreasing waste which will in turn be better for the environment. These conditions can be manipulated to increase bipy yield: Lewis acid, nucleophile, temperature, reaction time, reaction solvent, and phosphonium salt to Lewis acid and nucleophile ratio. This thesis specifically focused on the Lewis acid and comparing the bipy concentrations produced by different cobalt (II) salts. Cobalt (II) chloride had the highest average concentration of bipy with 920 µM. Cobalt (II) sulfate was 789 µM, cobalt (II) acetate 769 µM, cobalt (II) carbonate 487 µM, and cobalt (II) tetrafluoroborate was 477 µM. There was also found to be a correlation between anion basicity of the Lewis acid and the concentration of bipy produced with counter ions that do not fully dissociate giving higher bipy yields.

Semester/Year of Award

Fall 2025

Mentor

Benjamin F. Wicker

Mentor Department Affiliation

Chemistry

Access Options

Open Access Thesis

Degree Name

Honors Scholars

Degree Level

Bachelors

Department

Chemistry

Download

Share

COinS