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Title: Chemistry of electrophilic intermediates in the sulfonation process
Author: Thomas, G. L.
Awarding Body: University of Wales Swansea
Current Institution: Swansea University
Date of Award: 2003
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The study is more specifically concerned with the reactions of aromatic sulfonic anhydrides. The study was carried out in order to gain more knowledge on the reactions and behaviour of aromatic sulfonic anhydrides, and the role they play in the formation of sulfones in the industrial sulfonation process. An introduction to industrial sulfonation as used in the detergent industry is included. It has been proposed that sulfones are formed in the sulfonation process, by reaction of sulfonic anhydrides with alkylbenzene (starting material). An initial study of the reactions of p-toluenesulfonic anhydride with toluene using different catalysts was carried out, providing background knowledge for the more detailed studies that followed. A number of competition reactions were completed, investigating the influence of substituents in a series of arenes on the relative rates of reaction of p-toluenesulfonic anhydride. Studies were carried out using nitromethane as solvent and AlCl3 as catalyst. Included in the study is a review of the synthesis of diaryl sulfones, and the synthesis of a number of unsymmetrical sulfones. A new route to di-tolyl sulfone was identified from intramolecular reaction of p-toluenesulfonic anhydride catalysed by AlCl3. The relative rate of formation of sulfones via this route compared to Friedel-Crafts type sulfonylation reactions and was studied. The relative rates were found to be very low. The synthesis of a series of aromatic sulfonic anhydrides was carried out using direct sulfonation with SO3. The sulfonic anhydrides were then used to investigate the effect of substituents on the rates of reaction of substituted benzenesulfonic anhydrides reacting with toluene. The reactions were carried out in nitromethane using AlCl3 as the catalyst.
Supervisor: Not available Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available