Computational study of Simultaneous synthesis of optically active (RS)-1,2,4-butanetriol trinitrate (BTTN)

Abstract

In respective water or ethanol polarizable continuum cavity environments, simultaneous aldol condensation was performed using density functional theory (DFT) computational method to model the synthesis of optically active (RS)-1,2,4-butanetriol trinitrate (BTTN). The results of reaction energy barrier analysis suggested feasible routes with lower activation energies to obtain either the (R)- or (S)-configuration product in ethanolic solution. In addition, local analysis of average inter-particulate distances of reaction species revealed that a stronger inter-particulate interaction accompanied a shorter average distance in the ethanol system. The stabilization effect also indicated that related syntheses would be able to proceed in ethanol. Furthermore, relative to the production of (R)-BTTN, a lower overall energy of 425.3 kJ/mol was required for the synthesis of (S)-BTTN. Through analysis of the effects of temperature on the reaction rates of individual parallel stages of (R)- and (S)-species synthesis, it was simple to adjust the reaction temperature accordingly to differentiate between relative rates in order to obtain a product of a specific configuration. Graphical abstract ᅟ.

Optimization of 1,2,4‐butanetriol production from xylose in Saccharomyces cerevisiae by metabolic engineering of NADH/NADPH balance

“…BT can be converted into 1,2,4‐butanetriol trinitrate (BTTN), a nitrate ester explosive (Gouranlou & Kohsary, 2010). BTTN and nitroglycerin mixture, the so‐called double‐base propellants, allow for low‐temperature explosion, shock stability, and safety for use (Liu, Tsai, & Liu, 2017; Pei et al, 2018). BTTN can be a replacement for nitroglycerin (Gouranlou & Kohsary, 2010).…”