Eastern Kentucky University

Phosphorus Extrusion and 2,2'-Bipyridine Synthesis

Grade Level at Time of Presentation

Junior

Major

Forensic Science

Minor

Chemistry

Institution 24-25

Eastern Kentucky University

KY House District #

50

KY Senate District #

14

Department

Chemistry and Forensic Science

Abstract

In this project, we investigated the extrusion of a 2,2'-bipyridine (bipy) from diphenyldi(2-pyridyl) phosphonium bromide ([Dipyphos]Br). Our goal was to determine the optimal conditions to synthesize bipy from [Dipyphos]Br, using CoCl2 as a Lewis acid and piperidine as a nucleophile. Our baseline reaction was reacted the phosphonium salt, Lewis acid, and nucleophile for 24 hours before quenching with Na2EDTA. A standardization curve of known concentrations of bipy, along with the reaction products were analyzed via High Pressure Liquid Chromatographer (HPLC). This would allow for the determination of the concentration of bipy in the unknown solutions. A linear fit of the curve yielded and R2 value of 0.9594 and widely varied yields for multiple samples run under the same conditions. Three new samples of the cobalt(II) chloride and piperidine were run again and this time the concentration curve was fitted with a logarithmic line of fit which produced a high R2 value of 0.9951, which allowed more accurate concentration and percent yield calculations to be done. Using this method, the average yield of bipy was established to be 56.38% with a standard deviation of 6.16. We are currently exploring other methods for quickly determining bipy yield. Once a reliable method is identified, we will continue with the methodology project by exploring different Lewis acids, nucleophiles, solvents, reaction timed, and temperatures to see which variables together produce the highest percent yield.

This document is currently not available here.

Share

COinS
 

Phosphorus Extrusion and 2,2'-Bipyridine Synthesis

In this project, we investigated the extrusion of a 2,2'-bipyridine (bipy) from diphenyldi(2-pyridyl) phosphonium bromide ([Dipyphos]Br). Our goal was to determine the optimal conditions to synthesize bipy from [Dipyphos]Br, using CoCl2 as a Lewis acid and piperidine as a nucleophile. Our baseline reaction was reacted the phosphonium salt, Lewis acid, and nucleophile for 24 hours before quenching with Na2EDTA. A standardization curve of known concentrations of bipy, along with the reaction products were analyzed via High Pressure Liquid Chromatographer (HPLC). This would allow for the determination of the concentration of bipy in the unknown solutions. A linear fit of the curve yielded and R2 value of 0.9594 and widely varied yields for multiple samples run under the same conditions. Three new samples of the cobalt(II) chloride and piperidine were run again and this time the concentration curve was fitted with a logarithmic line of fit which produced a high R2 value of 0.9951, which allowed more accurate concentration and percent yield calculations to be done. Using this method, the average yield of bipy was established to be 56.38% with a standard deviation of 6.16. We are currently exploring other methods for quickly determining bipy yield. Once a reliable method is identified, we will continue with the methodology project by exploring different Lewis acids, nucleophiles, solvents, reaction timed, and temperatures to see which variables together produce the highest percent yield.