Document Type
Thesis
Date of Award
6-30-1957
Degree Name
Master of Science in Chemical Engineering - (M.S.)
Department
Chemical Engineering
First Advisor
James A. Bradley
Second Advisor
Saul I. Kreps
Third Advisor
C. L. Mantell
Abstract
The object of this work was to determine the relative activity of the halogens, chlorine, bromine and iodine toward hydrolysis in a water-soluble aryl halide in which the halogen is activated by a nitrogroup in the orthoposition.
The order of activity was found to be C1) POI. In the case of the chlorine compound a run was also made on sodium 2-chloro-5-nitrobenzenesulfonate in which the nitro group is in a pare position with respect to the halogen.
The preparations of sodium or potassium 4-chloro-3-nitrobenzene sulfonate (I), sodium or potassium 4-bromo-3-nitrobenzene sulfonate (II), sodium or potassium 4-iodo-3-nitrobenzene sulfonate (III), and sodium 2-chloro-5-nitrobenzene sulfonate (Iv) are discussed. The results of some experiments that were attempted to minimize the amount of a by product, a sulfone, that is formed during the preparations of (I) and (II) are given. The minimum concentration of sulfuric acid necessary for the sulfonation of (I) and (ii) was determined.
The purification and method of analysis of (I), (II), (III) and (IV) are given.
The rates of hydrolysis of (I), (II). (III) and (IV) were determined by measuring the rate constant at three temperatures. An Arrhenius plot was made for each compound and the activation energy was determined. For sodium 4-chloro-3-nitrobenzene sulfonate, the activation energy was 20,800 calories; for the potassium salt of this compound, 19,400 calories; for potassium 4-bromo-3-nitrobenzene sulfonate, 22,400 calories; for potassium 4-iodo-3-nitrobenzene sulfonate; 24.000 calories; and for sodium 2-chloro-5-nitrobenzene sulfonate, 27,200 calories.
Recommended Citation
Roeder, Jack Robert, "The rates of hydrolysis of aryl halides" (1957). Theses. 2595.
https://digitalcommons.njit.edu/theses/2595
