Comparative simulation study of chemical synthesis of energetic (R)‐1,2,4‐butanetriol trinitrate plasticizer

Liu, Min-Hsien; Liu, Chuan-Wen

doi:10.1002/qua.25402

Cited by 4 publications

(2 citation statements)

References 22 publications

(19 reference statements)

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“…Prior to the preliminary preparation stage, simulation details can provide reliable information for feasibility evaluation, which will avoid nonessential resource waste and enable successful experimental research. In this work, according to the literature combined with our experience of reaction modeling, reasonable AP decomposition mechanisms were proposed. All created reaction systems were simulated and analyzed, and the achievements of this study are summarized as follows: In contrast to gaseous unimolecular reaction modeling, MS can be employed to construct a similar real gas environmental system for related analysis, which deserves attention and promotion. Reaction kinetics‐related parameters including the activation energy, rate constant, and pre‐exponential factor, and thermodynamics‐related values of thermal enthalpy, Gibbs energy, and entropy were obtained from theoretical calculation and used for comparative analysis. In addition to energy‐barrier comparison, local analysis of interparticulate interactions in the decomposition reaction system was employed to identify the positive catalytic effects of ammonium chlorate and the negative catalytic effects of ammonium phosphates and ammonium halides.…”

Section: Discussionmentioning

confidence: 99%

Theoretical investigation of the catalytic effect of microingredients on ammonium perchlorate (AP) thermal decomposition

Liu

Tsai

2018

J Chinese Chemical Soc

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This study employed quantum chemical modeling to explore the low‐temperature (i.e., below 300 °C) decomposition of ammonium perchlorate (AP) in terms of the reaction mechanisms, analyzing the kinetics of decomposition in gaseous noncatalyzed and catalyzed systems. Based upon transition‐state theory, the calculated rate constant together with the initial partial pressure of the reaction species were included in the integrated form into the rate law of the elementary reaction to compute the half‐life of AP decomposition and further evaluate the corresponding lifetime of the stored material. The results of this study revealed that upon increasing the reaction temperature, the stepwise decrease in the activation barrier and the stepwise increase in the rate constant of AP decomposition exhibited expected trends. In addition, via proton transfer and bond‐cleavage mechanisms, ammonium chlorate exerted a positive catalytic effect that showed decomposition is unfavorable. However, ammonium dihydrogen phosphate and ammonium halide exhibited negative catalytic effects that slowed decomposition, and both of them may be incorporated into AP composite propellants to prolong their shelf life. The use of these stabilizing catalysts is estimated to increase the relative lifetime of materials under storage by two orders of magnitude, potentially benefiting ammunition storage.

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Section: Discussionmentioning

confidence: 99%

Theoretical investigation of the catalytic effect of microingredients on ammonium perchlorate (AP) thermal decomposition

Liu

Tsai

2018

J Chinese Chemical Soc

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“…BTTN has the advantages of low impact sensitivity, high energy level, high thermal stability, no brittleness at low temperature and high reaction safety, and thus is an excellent substitute for nitroglycerin [ 10 ]. In addition, 1,2,4-BT can also be used as the precursor for production of plastic monomers or medicines [ 11 , 12 ]. Currently, 1,2,4-BT is commercially produced through malate reduction with NaBH 4 under high temperature and high pressure [ 13 ].…”

Section: Introductionmentioning

confidence: 99%

Efficient production of 1,2,4-butanetriol from corn cob hydrolysate by metabolically engineered Escherichia coli

Li,

Wang,

et al. 2024

Microb Cell Fact

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Corn cob is a major waste mass-produced in corn agriculture. Corn cob hydrolysate containing xylose, arabinose, and glucose is the hydrolysis product of corn cob. Herein, a recombinant Escherichia coli strain BT-10 was constructed to transform corn cob hydrolysate into 1,2,4-butanetriol, a platform substance with diversified applications. To eliminate catabolite repression and enhance NADPH supply for alcohol dehydrogenase YqhD catalyzed 1,2,4-butanetriol generation, ptsG encoding glucose transporter EIICBGlc and pgi encoding phosphoglucose isomerase were deleted. With four heterologous enzymes including xylose dehydrogenase, xylonolactonase, xylonate dehydratase, α-ketoacid decarboxylase and endogenous YqhD, E. coli BT-10 can produce 36.63 g/L 1,2,4-butanetriol with a productivity of 1.14 g/[L·h] using xylose as substrate. When corn cob hydrolysate was used as the substrate, 43.4 g/L 1,2,4-butanetriol was generated with a productivity of 1.09 g/[L·h] and a yield of 0.9 mol/mol. With its desirable characteristics, E. coli BT-10 is a promising strain for commercial 1,2,4-butanetriol production.

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

Liu¹,

Tsai²,

Liu³

2017

J Mol Model

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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.

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Comparative simulation study of chemical synthesis of energetic (R)‐1,2,4‐butanetriol trinitrate plasticizer

Cited by 4 publications

References 22 publications

Theoretical investigation of the catalytic effect of microingredients on ammonium perchlorate (AP) thermal decomposition

Theoretical investigation of the catalytic effect of microingredients on ammonium perchlorate (AP) thermal decomposition

Efficient production of 1,2,4-butanetriol from corn cob hydrolysate by metabolically engineered Escherichia coli

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

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