Abstract
This study investigated the selective alcoholysis of lactide catalyzed by Lewis pairs, B(C6F5)3-phosphines. Among the phosphines examined in this study, tricyclohexylphosphine (Cy3P) exhibited both high activity and high selectivity in this system. The alcoholysis of l-lactide (L-LA) with benzyl alcohol by the B(C6F5)3-Cy3P system produced benzyl lactyllactate in high conversion (âź96%) with high selectivity (>91%) under the wide range of feed [L-LA]0:[alcohol]0 molar ratio in toluene at 100 °C. In this catalyst system, the reactions of L-LA with isopropyl alcohol or tertâbutyl alcohol were much slower than those with primary alcohols such as benzyl alcohol, 1-butanol, and ethanol. Thus, the high chemo-selectivity of the B(C6F5)3-phosphine systems should come from their steric hindrance which differentiates the reactivity to the primary hydroxy group and that to the secondary one.
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