Reaction Mechanisms of Synthesis of 3,4-Epoxybutyric Acid from 3-Hydroxy-γ-Butyrolactone by Density Functional Theory

Abstract: In this paper, carried out were the investigations on the synthetic reaction mechanisms of 3,4-epoxybutyric acid (EBA) from 3-hydroxy-{\gamma}-butyrolactone (HBL) with two different activating agents, methanesulfonyl chloride (MC) or acetic acid (AA), respectively, and on the convertion of EBA to L-carnitine by density functional theory (DFT/B3LYP). The theoretical calculations showed that the two reaction mechanisms of EBA synthesis with MC or AA as an activating agent were nearly the same. If activated HBL is hydrolysed, not only ring cleavage reaction, but also reverse reaction to HBL can take place. In the case of AA as the activating agent, the activation energy ( energy barrier ) for EBA synthesis is 1.8 times larger than that with MC. It means that the synthesis of EBA with AA may make more by-products with less yield of EBA than that with MC, that can be one reason why AA gave the less yield than MC in EBA synthesis, as reported in the previous experimental study.