Abstract
Desulfonations of sodium pentane-1-sulfonate and sodium pentane-2-sulfonate with alkalis, such as KOH, NaOH and LiOH, was studied.
The degrees of initial desulfonation temperatures of sodium pentane sulfonates with alkalis were higher in order of NaOH, KOH, LiOH, and the desulfonation temperature of pentane-l-sulfonate with each alkali was higher than that of pentane-2-sulfonate.
In the reaction of pentane-1-sulfonate with each alkali, the product was 1-pentene accompanying a mixture of trans-2- and cis-2-pentene which seemed to be produced by isomerization of 1-pentene by the contact with alkali.
The Composition of produced olefins was affected by basicity and quantity of alkali, namely, weaker the basicity, the proportion of 1-pentene increased, and smaller the quantity, except for KOH, the proportion of 1-pentene increased.
Moreover the degree of isomerization of produced pentene was decreased under constant reduced pressure.
On the other hand, in the reaction of pentane-2-sulfonate with KOH, the composition of produced olefins was similar to those from pentane-1-sulfonate, independent of the quantity of KOH. However, with small quantity of NaOH or LiOH, 1-pentene was produced predominantly, and 2-pentene seemed principally to be the product by desulfonation.
From these results, the alkali-fusion reaction of sulfonate was inferred to be E2 reaction regulated by Hofmann rule.
