Nitration kinetics of 6-hydroxy-2-methylpyrimidin-4(3H)-one and 2-methoxy-2-methylimidazolidine-4,5-dione

Kushtaev, A. A.; D’yakonov, A. V.; Yudin, N. V.; Zbarskii, V. L.

doi:10.1134/s1070427209100073

Cited by 4 publications

(9 citation statements)

References 4 publications

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“…Figure indicates that FOX-7 synthesis is achievable only after formation of 5 . Nitration of 2-methyl-4,6-dihydroxypyrimidine is believed to be a sequential attack of nitronium ions at an active methylene site and the methyl side chain. , The expected reaction scheme is shown in Figure .…”

Section: Process Chemistry Of 2-methyl-pyrimidine-46-dione Nitrationmentioning

confidence: 99%

Process Optimization, Product Profile Mapping, and Intensification of 1,1-Diamino-2,2-dinitroethylene

Jadhav

Radhakrishnan

Patil

et al. 2019

Org. Process Res. Dev.

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Industrialization of a chemical process needs an understanding of process chemistry, optimal process envelope, and the best choice of operation. 1,1-Diamino-2,2-dinitroethylene (FOX-7) is a new generation, and the highly insensitive compound finds application in high-energy formulations as well as preparation of novel high-energy compounds. The present study highlights efforts made for establishing a continuous process for FOX-7. The intermediates of nitration of 2-methylpyrimidine-4, 6-dione were isolated and characterized by spectroscopic tools. Reaction kinetics was also derived for the formation of intermediates. Product profiles of the reaction were evaluated on deriving expressions for various reactors. The simultaneous effect of heat and reaction was evaluated in a tubular reactor to obtain the runaway reaction condition. The effective reactor scheme was evaluated, designed, and experimented. Process intensification was carried out in a continuous set up comprising various contact patterns. The present study delivered a safe and productive method for FOX-7 processing

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Section: Process Chemistry Of 2-methyl-pyrimidine-46-dione Nitrationmentioning

confidence: 99%

Process Optimization, Product Profile Mapping, and Intensification of 1,1-Diamino-2,2-dinitroethylene

Jadhav

Radhakrishnan

Patil

et al. 2019

Org. Process Res. Dev.

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“…Figure 1. Scheme for the synthesis of FOX-7 [4,5] The kinetics of the nitration of MPD has been considered in a few studies [4][5][6][7][8]. The kinetic parameters of this reaction were obtained in [4] on a small scale (500 mL capacity reactor).…”

Section: Introductionmentioning

confidence: 99%

“…In Ref. [7], the kinetics of the reactions allowing FOX-7 to be obtained as the product were analyzed. In one of them, MPD was a starting reactant.…”

Section: Introductionmentioning

confidence: 99%

“…The nitration kinetics were studied using HPLC and UV spectrophotometry. According to a scheme of the reaction proposed in [7], the product of nitration of MPD is 2-methyl-5-nitropyrimidine-4,6-dione (MNMPD) and compound TNMPD is a product of its nitration. This latter product is capable of relatively rapid change giving a mixture of further nitration products.…”

Section: Introductionmentioning

confidence: 99%

“…A model was proposed in [8] for the synthesis of FOX-7 in the manner described in [7]. The assumption of three consecutive reactions was taken into account.…”

Section: Introductionmentioning

confidence: 99%

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Modeling of the Nitration of 2-Methylpyrimidine-4,6-dione (MPD)

Belaada

Trzciński

Chyłek

2018

Cent. Eur. J. Energ. Mater.

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The conditions and kinetics of nitration of 2-methylpyrimidine-4,6dione (MPD), which leads to the formation of 1,1-diamino-2,2-dinitroethene (DADNE, FOX 7) via 5,5-dinitro-2-(dinitromethylene)pyrimidine-4,6-dione, are presented. An analysis of literature data enabled us to propose a simple model of the nitration of MPD. The model was verified on the basis of literature data and our own experimental data. The influence of the rate of addition of nitric acid, into a model reactor, on temperature and composition of the reaction mixture was investigated numerically. The proposed nitration model could be useful in a study of the MPD nitration process on a large scale.

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Comparative simulation study of chemical synthesis of functional DADNE material

Liu¹,

Liu²

2016

J Mol Model

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Amorphous molecular simulation to model the reaction species in the synthesis of chemically inert and energetic 1,1-diamino-2,2-dinitroethene (DADNE) explosive material was performed in this work. Nitromethane was selected as the starting reactant to undergo halogenation, nitration, deprotonation, intermolecular condensation, and dehydration to produce the target DADNE product. The Materials Studio (MS) forcite program allowed fast energy calculations and reliable geometric optimization of all aqueous molecular reaction systems (0.1-0.5 M) at 283 K and 298 K. The MS forcite-computed and Gaussian polarizable continuum model (PCM)-computed results were analyzed and compared in order to explore feasible reaction pathways under suitable conditions for the synthesis of DADNE. Through theoretical simulation, the findings revealed that synthesis was possible, and a total energy barrier of 449.6 kJ mol needed to be overcome in order to carry out the reaction according to MS calculation of the energy barriers at each stage at 283 K, as shown by the reaction profiles. Local analysis of intermolecular interaction, together with calculation of the stabilization energy of each reaction system, provided information that can be used as a reference regarding molecular integrated stability. Graphical Abstract Materials Studio software has been suggested for the computation and simulation of DADNE synthesis.

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Nitration kinetics of 6-hydroxy-2-methylpyrimidin-4(3H)-one and 2-methoxy-2-methylimidazolidine-4,5-dione

Cited by 4 publications

References 4 publications

Process Optimization, Product Profile Mapping, and Intensification of 1,1-Diamino-2,2-dinitroethylene

Process Optimization, Product Profile Mapping, and Intensification of 1,1-Diamino-2,2-dinitroethylene

Modeling of the Nitration of 2-Methylpyrimidine-4,6-dione (MPD)

Comparative simulation study of chemical synthesis of functional DADNE material

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