Sulfonation Mechanism of Fatty Acid Methyl Ester with Sulfur Trioxide

概要

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Methyl laurate used in this study as an original fatty ester) was easily converted to a 1 molar SO3 adduct (first intermediate) by adding SO3 at-20°C. This intermediate was found to be in equilibrium with the original ester. The energy of addition of SO3 to form the intermediate was about 14 kcal/mol based on exchange rates of the equilibrium. Sulfonation of the α-position of an ester occurred not on the original ester but on the first intermediate to give a 2-molar SO3 adduct (second intermediate). The α-sulfonation followed kinetically the second order for the first intermediate and had an activation energy of about 25 kcal/mol. The rate of the final reaction to the α-sulfofatty acid methyl ester (α SFM) from the second intermediate depended on the amount of co-existing ester. According to the experimental results, the sulfonation mechanism for α SFM is proposed.
Japan Oil Chemists' Societyの論文