Date of Award

7-1936

Document Type

Thesis

Degree Name

Master of Science (MS)

First Advisor

O.W. Chapman

Second Advisor

L. C. Heckert

Keywords

Pyrroles, Synthesis

Abstract

There is at present no method by which pyrrole, a compound found in both plants and animals, may be satisfactorily synthesised in quantities at low cost. Believing that such a synthesis is desirable, the research here reported was undertaken to investigate the possibility of producing pyrrole from inexpensive materials. This paper has included a study of the chemisty of pyrrole and the closely related compunds, thiophene and furance. The first step in the synthesis was an attempt to produce ethylene cyanide by the substitution of ethylene chloride for the bromide. The yield thus obtained was not great enough to justify the use of material as expensive as potassium cyanide. It is possible that the low yield was due in part to the fact that sufficiently low preassures for the distillation were not reached. Sodium cyanide in reaction with ethylene chloride failed to produce ethylene cyanide and ethylene chloride, compared with the activitiy of potassium cyanide and ethylene chloride. The failure may have been due to the decomposition upon heating of any ethylene cyanide which might have been formed. Substitution of cuprous cyanide and of potassium ferrocyanide for potassium cyanide also failed to produce the desired product, probably because these compounds were insoluble in all of the solvents employed. Satisfactory methods for the reduction of ethylene cyanide were not obtained.

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