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Original Articles

PRIMARY AND SECONDARY PRODUCTS IN THE LIQUID PHASE SO3-SULFONATION OF 1-ALKENES

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Pages 259-271 | Received 02 Feb 1984, Accepted 25 Apr 1984, Published online: 19 Dec 2006
 

Abstract

A number of linear (C5-C14) and branched (C5-C8) 1-alkenes were sulfonated by SO3 free or as its dioxane adduct in liquid phase. The composition of the mixtures just after SO3-consumption and several days later was investigated. In addition a thermochemical approach, by means of contributed bond energies, and a kinetic study of the evolution of the sulfonation mixtures show, at least with linear substrates, that a β-sultone is the product under kinetic control and slowly isomerizes into more stable alkenesulfonic acids, then γ- and δ-sultones. However alkenesulfonic acids, originating from the same zwitterionic intermediate as β-sultone, are already present in small amount at the very beginning of the sulfonation.

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