Document Type

Thesis

Date of Award

6-30-1960

Degree Name

Master of Science in Chemical Engineering - (M.S.)

Department

Chemical Engineering

First Advisor

Saul I. Kreps

Second Advisor

James A. Bradley

Third Advisor

Michael Frederick

Abstract

The acetylation of 5-chloropyridine-2,3-diamino with chloroacetyl-chloride to yield 5-chloropyridine-2,3-dichlo-roacetamide and the subsequent ring closure form 6-chloro-2-chloromethyl-3H-imidazo-(b)pyridine has been studied in detail. The method of experimentation utilized statistically designed mathematical experiments.

The yield of 5-chloropyridine-2,3-dichloroacetamido is dependent upon the excess of the reactants and temperature, while time is not a significant factor. An important contribution to the study was obtained by extracting the product with solvents and discovering that the ring closed material 6-chloro-2-chloromethyl-3H-imidazo-(b)pyridine yields in quantity during the diacetylation reaction.

The ring closure of 5-chloro-2,3-dichloroacetamidopyridine is markedly temperature dependent. Time has little effect on the reaction yield. The analysis of regression of the statistically designed experiment resulted in an equation for yield in terms of the reaction time and temperature. It was determined experimentally that reaction temperature of 100°C. resulted in a tar-like polymer instead of the cyclized product, 6-chloro-2-chloromethyl-3H-imidazo-(b)pyridine.

The surface response contour curves were plotted and the optimum conditions for the cyclization reaction determined. The recommended optimum reaction conditions are:

a. Temperature - 75°C

b. Time - 2 hours

c. Yield - 68 theoretical

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