Synthesis of Diazonium Perfluoroalkyl(Aryl) Sufonimide (PFSI) Zwitterions for Solid Acid Alkylation Catalysts

• Main Author: Ahmad, Husan
• Format: Others
• Published: Digital Commons @ East Tennessee State University 2015
• Subjects: Alkylation; Catalyst; Petroleum; Organic Chemistry
• Online Access: https://dc.etsu.edu/honors/314; https://dc.etsu.edu/cgi/viewcontent.cgi?article=1323&context=honors

The final objective of this project is to create an environmentally friendly solid alkylation catalyst to replace the commercially available liquid acid catalysts, such as hydrofluoric acid and sulfuric acid, which are used in the petroleum industry. My research target is to synthesize the diazonium PFSI zwitterions, which can be chemically grafted on the silica as the solid alkylation catalyst. A 4-steps synthesis is designed to prepare the diazonium PFSI zwitterions. The first two steps were successfully completed in the lab. The first one is to prepare the starting material of 4-nitrobenzenesulfonamide from an ammonolysis reaction between 4-nitrobenzene sulfonyl chloride and ammonium hydroxide. And next, a base catalyzed coupling reaction was carried out with 4-nitrobenzenesulfonamide and commercially available perfluorobutane sulfonyl fluoride with nitrogen gas (N2) protection. The coupling product (I in Figure 1) was then purified by extraction and recrystallization. All chemicals in the synthesis procedure were characterized with proton NMR, fluorine NMR, Infrared (IR) spectroscopy and melting points.