Chemistry ETDs

Publication Date



In 1953 Cook, Hewett, and Rieger found a highly carcinogenic hydrocarbon in coal tar. By a variety of solvent extraction methods, fractional distillation, and crystallization several pure hydrocarbons were isolated from the crude pitch. Two new pentacyclic aromatic hydrocarbons were isolated and since only small quantities of them were available it was decided to ascertain their structures by synthesis instead of degradetive experiments. The hydrocarbon samples were obtained with great difficulty from two tons of crude pitch. The problem was simplified since ten of the possible fifteen pentacyclic hydrocarbons were known. From certain similarities of these hydrocarbons to perylene its isomerides, namely the 1,2- and 3,4-benzpyrenes, were prepared and proved to be identical with the hydrocarbons isolated. Carcinogenic testing revealed that only the 3,4-benzpyrene was active.

Project Sponsors

National Cancer Institute of the United States Public Health Service



Document Type


Degree Name

Chemistry and Chemical Biology

Level of Degree


Department Name

Department of Chemistry and Chemical Biology

First Committee Member (Chair)

Guido Herman Daub

Second Committee Member

Milton Kahn

Third Committee Member

Raymond Castle

Fourth Committee Member

Paul William Healy