Degree Name
MS (Master of Science)
Program
Chemistry
Date of Award
8-2015
Committee Chair or Co-Chairs
Hua Mei
Committee Members
Peter Zhao, Abbas G. Shilabin
Abstract
In order to improve the synthetic route for diazonium perfluoroalkyl benzenesulfonylimide (PFSI) zwitterionic monomers, N-deacetylation of the coupling product was proposed to replace the reduction of aromatic amine intermediates. A series of hydrolysis methods, such as acid and base catalyzed refluxing, were explored for the N-deacetylation to obtain the PFSI aromatic amine. Factors such as temperature, concentration of acid/base and the time needed for the reaction to take place were investigated in an attempt to optimize the reaction condition. The basic hydrolysis was preferred since it was expected to carry out the N-deacetylation and debromination in one batch reaction. N-deacetylation in base at high concentrations was successful, however, side reaction of the perfluorovinyl ether occurred. It was discovered that the best N-deacetylation method is to reflux/sonicate the coupling product with acid in methanol for six hours. The intermediates and purified products were characterized with 1HNMR, 19FNMR, GC-MS and IR.
Document Type
Thesis - unrestricted
Recommended Citation
Abban, Grace, "Methodology Study of N-deacetylation of 4-acetamido-perfluoroalkylbenzenesulfonimide" (2015). Electronic Theses and Dissertations. Paper 2553. https://dc.etsu.edu/etd/2553
Copyright
Copyright by the authors.