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
Michael Frederick
Third Advisor
Joseph Joffe
Abstract
A determination of equilibrium constants and reaction kinetics for the esterification of ortho, meta, and para-nitrobenzoic acids with methanol and ethanol was performed. A search of past literature showed that the equilibrium constants for the above acids and alcohols had not been measured previously.
The equilibrium constants (Ke) obtained for ortho, meta, and para-nitrobenzoic acids using p-toluene sulfonic acid as catalyst and ethanol as the alcohol were 3.59, 4.56, and 2.91: respectively. Using methanol as the alcohol, the corresponding constants were 2.61: 2.65, and 1.92.
Hydrochloric acid was also studied as a reaction catalyst, but, a side reaction between catalyst and alcohol invalidated the results.
The largest influence on the rate of reaction was found to be the position of the substituted nitro group (ortho, meta or para) in the nitrobenzoic acids. As an example, the ortho nitrobenzoic acid yielded lowest reaction rate constants with ethanol.
All values are given in the foam of the second order reaction rate constant, K1 in minutes-1 (millimolesigram)-1 and are summarized in the following table: Nitrobenzoic AcidAlcoholCatalystRateMean Reaction Temperature °Cparaethanolp-toluene sulfonic acid6.55 x 10-481.5paraethanolHCl5.98 x 10-465.8metaethanolp-toluene sulfonic acid7.84 x 10-481.6metaethanolnone1.05 x 10-681.4orthoethanolp-toluene sulfonic acid7.23 x 10-581.8orthoethanolHCl7.07 x 10-565.9metamethanolHCl10.2 x 10-465.7
The rates reported are based on single experiments.
The rate studies were made with concentrations of the nitro-benzoic acid much greater than that reported by previous investigators in order to approach more closely conditions which might be found in industrial esterifications.
Recommended Citation
Korzun, John Nicholas, "Equilibrium and reaction rate constants of esterification of nitrobenzoic acids" (1960). Theses. 2975.
https://digitalcommons.njit.edu/theses/2975
