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Kinetics of sulfonation of amines of the benzene series with sulfur trioxide

Journal Article · · J. Org. Chem. USSR (Engl. Transl.); (United States)
OSTI ID:6008422

The sulfonation of amines of the benzene series with sulfur trioxide in dichloroethane is described by a third-order kinetic equation for an irreversible process, and first order is observed with respect to the compound being sulfonated and second with respect to the sulfur trioxide. The unprotonated molecules of the amines undergo sulfonation, and this leads to the production of the para-aminosulfonic acids with small amounts of the ortho isomers. The reaction mechanism involves electrophilic reaction of the unprotonated amine molecule with the sulfur trioxide dimer S/sub 2/O/sub 6/ and subsequent dissociation of the obtained pyrosulfonate with the production of the amino sulfonic acid and sulfur trioxide. Sulfonation with sulfur trioxide is of interest in connection with the high rate and degree of completion of the reaction and the absence of energy expenditures.

Research Organization:
Ivanovo Scientific-Research Institute of Film Materials and Synthetic Leather for Technical Purposes (USSR)
OSTI ID:
6008422
Journal Information:
J. Org. Chem. USSR (Engl. Transl.); (United States), Journal Name: J. Org. Chem. USSR (Engl. Transl.); (United States) Vol. 24:3; ISSN JOCYA
Country of Publication:
United States
Language:
English