Browse
Submit Data
Databases
API
Help

Dataset Information

0 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Effects of Cocrystallization on the Structure and Properties of Melt-Cast Explosive 2,4-Dinitroanisole: A Computational Study.

ABSTRACT: Melt-cast explosive 2,4-dinitroanisole (DNAN) crystal and its cocrystals DNAN/1,3-dinitrobenzene (DNB) and DNAN/2-nitroaniline (NA) were used to identify the effects of cocrystallization on the crystal structure, non-covalent interactions, and melting points of the DNAN crystal through density functional theory and molecular dynamics. The components DNB and NA with subtle structure variations between the nitro group and amino group can significantly affect the non-covalent interactions, especially the π-π stacking and H-bonds, which can lead to different crystal stacking styles. The melting points of the DNAN crystal are decreased through the cocrystallization, which expands the utilization of the DNAN-based melt cast explosives. Our study deciphers the effects caused by the cocrystallization on the structure and properties of melt cast explosives and may help to design and optimize novel melt-cast explosives.

SUBMITTER: Wang D

PROVIDER: S-EPMC9783160 | biostudies-literature | 2022 Dec

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

Effects of Cocrystallization on the Structure and Properties of Melt-Cast Explosive 2,4-Dinitroanisole: A Computational Study.

Wang Defu D Yang Lei L Zhu Weihua W

Molecules (Basel, Switzerland) 20221217 24

Melt-cast explosive 2,4-dinitroanisole (DNAN) crystal and its cocrystals DNAN/1,3-dinitrobenzene (DNB) and DNAN/2-nitroaniline (NA) were used to identify the effects of cocrystallization on the crystal structure, non-covalent interactions, and melting points of the DNAN crystal through density functional theory and molecular dynamics. The components DNB and NA with subtle structure variations between the nitro group and amino group can significantly affect the non-covalent interactions, especial ...[more]

PMID: 36558147

Similar Datasets

Research on TNTON/DNTF eutectic characteristics: an exploration of low eutectic mixture based melt-cast explosive carriers.

Project description:To modify the sensitivity and melting point of the casting of DNTF, a eutectic system of insensitive explosive 3,5,5-trinitro-1,3-oxazinane (TNTON) and DNTF was prepared through a new method. The melting and liquefaction processes of TNTON/DNTF at different ratios were investigated, and a T-x phase diagram was established. The melting and decomposition processes of TNTON, DNTF, and TNTON/DNTF eutectic at different heating rates were compared, while the sensitivity tests were conducted to study the desensitizing effect of TNTON on DNTF. Using EXPLO-5 software, the detonation performance of the TNTON/DNTF eutectic was calculated. The experimental results show that the stoichiometric composition of the TNTON/DNTF eutectic is 58.26 : 41.74, with an average melting point of 69 °C. With the increase of heating rate, both the melting and decomposition reactions are delayed. According to the activation energy (E a) curve, the thermal decomposition is through an autocatalytic process. The impact and friction sensitivity of the TNTON/DNTF eutectic are 38 J and 252 N, respectively. Theoretical density of the TNTON/DNTF eutectic is 1.906 g cm-3, and the calculated detonation velocity is 8921 m s-1. The TNTON/DNTF eutectic exhibits good thermal stability and can significantly reduce the sensitivity of DNTF while maintaining its high energy level. The detonation performance of TNTON/DNTF low eutectic cast explosive is better than that of TNT based cast explosive.

| S-EPMC11578041 | biostudies-literature

Metabolism and Photolysis of 2,4-Dinitroanisole in Arabidopsis.

Project description:New insensitive munitions explosives, including 2,4-dinitroanisole (DNAN), are replacing traditional explosive compounds to protect soldiers and simplify transport logistics. Despite the occupational safety benefits of these new explosives, feasible strategies for cleaning up DNAN from soil and water have not been developed. Here, we evaluate the metabolism of DNAN by the model plant Arabidopsis to determine whether phytoremediation can be used to clean up contaminated sites. Furthermore, we evaluate the role of photodegradation of DNAN and its plant metabolites within Arabidopsis leaves to determine the potential impact of photolysis on the phytoremediation of contaminants. When exposed to DNAN for three days, Arabidopsis took up and metabolized 67% of the DNAN in hydroponic solution. We used high resolution and tandem mass spectrometry in combination with stable-isotope labeled DNAN to confirm ten phase II DNAN metabolites in Arabidopsis. The plants separately reduced both the para- and ortho-nitro groups and produced glycosylated products that accumulated within plant tissues. Both DNAN and a glycosylated metabolite were subsequently photolyzed within leaf tissue under simulated sunlight, and [15N2]DNAN yielded 15NO2- in leaves. Therefore, photolysis inside leaves may be an important, yet under-explored, phytoremediation mechanism.

| S-EPMC5839145 | biostudies-literature

(Bio)transformation of 2,4-dinitroanisole (DNAN) in soils.

Project description:Recent studies have begun to assess the environmental fate and toxicity of 2,4-dinitroanisole (DNAN), an insensitive munition compound of interest to defense agencies. Aerobic and anaerobic DNAN biotransformation in soils was evaluated in this study. Under aerobic conditions, there was little evidence of transformation; most observed removal was attributed to adsorption and subsequent slow chemical reactions. Under anaerobic conditions, DNAN was reductively (bio)transformed and the rate of the transformation was positively correlated with soil organic carbon (OC) up to a threshold of 2.07% OC. H2 addition enhanced the nitroreduction rate compared to endogenous treatments lacking H2. Heat-killed treatments provided rates similar to the endogenous treatment, suggesting that abiotic factors play a role in DNAN reduction. Ten (bio)transformation products were detected by high-resolution mass spectrometry. The proposed transformation pathway involves reduction of DNAN to aromatic amines, with putative reactive nitroso-intermediates coupling with the amines to form azo dimers. Secondary reactions include N-alkyl substitution, O-demethylation (sometimes followed by dehydroxylation), and removal of an N-containing group. Globally, our results suggest that the main reaction DNAN undergoes in anaerobic soils is nitroreduction to 2-methoxy-5-nitroaniline (MENA) and 2,4-diaminoanisole (DAAN), followed by anaerobic coupling reactions yielding azo-dimers. The dimers were subsequently subject to further (bio)transformations.

| S-EPMC4695256 | biostudies-literature

Biotransformation of 2,4-dinitroanisole by a fungal Penicillium sp.

Project description:Insensitive munitions explosives are new formulations that are less prone to unintended detonation compared to traditional explosives. While these formulations have safety benefits, the individual constituents, such as 2,4-dinitroanisole (DNAN), have an unknown ecosystem fate with potentially toxic impacts to flora and fauna exposed to DNAN and/or its metabolites. Fungi may be useful in remediation and have been shown to degrade traditional nitroaromatic explosives, such as 2,4,6-trinitrotoluene and 2,4-dinitrotoluene, that are structurally similar to DNAN. In this study, a fungal Penicillium sp., isolated from willow trees and designated strain KH1, was shown to degrade DNAN in solution within 14 days. Stable-isotope labeled DNAN and an untargeted metabolomics approach were used to discover 13 novel transformation products. Penicillium sp. KH1 produced DNAN metabolites resulting from ortho- and para-nitroreduction, demethylation, acetylation, hydroxylation, malonylation, and sulfation. Incubations with intermediate metabolites such as 2-amino-4-nitroanisole and 4-amino-2-nitroanisole as the primary substrates confirmed putative metabolite isomerism and pathways. No ring-cleavage products were observed, consistent with other reports that mineralization of DNAN is an uncommon metabolic outcome. The production of metabolites with unknown persistence and toxicity suggests further study will be needed to implement remediation with Penicillium sp. KH1. To our knowledge, this is the first report on the biotransformation of DNAN by a fungus.

| S-EPMC5772970 | biostudies-literature

Aerobic biodegradation of 2,4-Dinitroanisole by Nocardioides sp. strain JS1661.

Project description:2,4-Dinitroanisole (DNAN) is an insensitive munition ingredient used in explosive formulations as a replacement for 2,4,6-trinitrotoluene (TNT). Little is known about the environmental behavior of DNAN. There are reports of microbial transformation to dead-end products, but no bacteria with complete biodegradation capability have been reported. Nocardioides sp. strain JS1661 was isolated from activated sludge based on its ability to grow on DNAN as the sole source of carbon and energy. Enzyme assays indicated that the first reaction involves hydrolytic release of methanol to form 2,4-dinitrophenol (2,4-DNP). Growth yield and enzyme assays indicated that 2,4-DNP underwent subsequent degradation by a previously established pathway involving formation of a hydride-Meisenheimer complex and release of nitrite. Identification of the genes encoding the key enzymes suggested recent evolution of the pathway by recruitment of a novel hydrolase to extend the well-characterized 2,4-DNP pathway.

| S-EPMC4249229 | biostudies-literature

Environmental Fate of <sup>14</sup>C Radiolabeled 2,4-Dinitroanisole in Soil Microcosms.

Project description:2,4-Dinitrosanisole (DNAN) is an insensitive munitions component replacing conventional explosives. While DNAN is known to biotransform in soils to aromatic amines and azo-dimers, it is seldom mineralized by indigenous soil bacteria. Incorporation of DNAN biotransformation products into soil as humus-bound material could serve as a plausible remediation strategy. The present work studied biotransformation of DNAN in soil and sludge microcosms supplemented with uniformly ring-labeled 14C-DNAN to quantify the distribution of label in soil, aqueous, and gaseous phases. Electron donor amendments, different redox conditions (anaerobic, aerobic, sequential anaerobic-aerobic), and the extracellular oxidoreductase enzyme horseradish peroxidase (HRP) were evaluated to maximize incorporation of DNAN biotransformation products into the nonextractable soil humus fraction, humin. Irreversible humin incorporation of 14C-DNAN occurred at higher rates in anaerobic conditions, with a moderate increase when pyruvate was added. Additionally, a single dose of HRP resulted in an instantaneous increased incorporation of 14C-DNAN into the humin fraction. 14C-DNAN incorporation to the humin fraction was strongly correlated (R2 = 0.93) by the soil organic carbon (OC) amount present (either intrinsic or amended). Globally, our results suggest that DNAN biotransformation products can be irreversibly bound to humin in soils as a remediation strategy, which can be enhanced by adding soil OC.

| S-EPMC5772931 | biostudies-literature

Zebrafish embryo toxicity of anaerobic biotransformation products from the insensitive munitions compound 2,4-dinitroanisole.

Project description:2,4-Dinitroanisole (DNAN) is an emerging insensitive munitions compound that readily undergoes anaerobic nitro-group reduction to 2-methoxy-5-nitroaniline (MENA) and 2,4-diaminoanisole (DAAN), followed by formation of unique azo dimers. Currently there is little knowledge on the ecotoxicity of DNAN (bio)transformation products. In the present study, mortality, development, and behavioral effects of DNAN (bio)transformation products were assessed using zebrafish (Danio rerio) embryos. The authors tested individual products, MENA and DAAN, as well as dimer and trimer surrogates. As pure compounds, 3-nitro-4-methoxyaniline and 2,2'-dimethoxy-4,4'-azodianiline caused statistically significant effects, with lowest-observable-adverse effect levels (LOAEL) at 6.4 μM on 1 or 2 developmental endpoints, respectively. The latter had 6 additional statistically significant developmental endpoints with LOAELs of 64 μM. Based on light-to-dark swimming behavioral tests, DAAN (640 μM) caused reduction in swimming, suggestive of neurotoxicity. No statistically significant mortality occurred (≤64 μM) for any of the individual compounds. However, metabolite mixtures formed during different stages of MENA (bio)transformation in soil were characterized using high-resolution mass spectrometry in parallel with zebrafish embryo toxicity assays, which demonstrated statistically significant mortality during the onset of azo-dimer formation. Overall the results indicate that several DNAN (bio)transformation products cause different types of toxicity to zebrafish embryos. Environ Toxicol Chem 2016;35:2774-2781. © 2016 SETAC.

| S-EPMC5052101 | biostudies-literature

Microgravity effects on nonequilibrium melt processing of neodymium titanate: thermophysical properties, atomic structure, glass formation and crystallization.

Project description:The relationships between materials processing and structure can vary between terrestrial and reduced gravity environments. As one case study, we compare the nonequilibrium melt processing of a rare-earth titanate, nominally 83TiO2-17Nd2O3, and the structure of its glassy and crystalline products. Density and thermal expansion for the liquid, supercooled liquid, and glass are measured over 300-1850 °C using the Electrostatic Levitation Furnace (ELF) in microgravity, and two replicate density measurements were reproducible to within 0.4%. Cooling rates in ELF are 40-110 °C s-1 lower than those in a terrestrial aerodynamic levitator due to the absence of forced convection. X-ray/neutron total scattering and Raman spectroscopy indicate that glasses processed on Earth and in microgravity exhibit similar atomic structures, with only subtle differences that are consistent with compositional variations of ~2 mol. % Nd2O3. The glass atomic network contains a mixture of corner- and edge-sharing Ti-O polyhedra, and the fraction of edge-sharing arrangements decreases with increasing Nd2O3 content. X-ray tomography and electron microscopy of crystalline products reveal substantial differences in microstructure, grain size, and crystalline phases, which arise from differences in the melt processes.

| S-EPMC10918169 | biostudies-literature

Use of qPCR to monitor 2,4-dinitroanisole degrading bacteria in water and soil slurry cultures.

Project description:Prediction and process monitoring during natural attenuation, bioremediation, and biotreatment require effective strategies for detection and enumeration of the responsible bacteria. The use of 2,4-dinitroanisole (DNAN) as a component of insensitive munitions leads to environmental contamination of firing ranges and manufacturing waste streams. Nocardioides sp. strain JS1661 degrades DNAN under aerobic conditions via a pathway involving an unusual DNAN demethylase. We used the deeply branched sequences of DNAN degradation functional genes as a target for development of a molecular method for detection of the bacteria. A qPCR assay was designed for the junction between dnhA and dnhB, the adjacent genes encoding DNAN demethylase. The assay allowed reproducible enumeration of JS1661 during growth in liquid media and soil slurries. Results were consistent with biodegradation of DNAN, accumulation of products, and classical biomass estimates, including most probable number and OD600. The results provide a sensitive and specific molecular method for prediction of degradation potential and process evaluation during degradation of DNAN.One-sentence summaryA unique target sequence in functional genes enables the design of a simple and specific qPCR assay for enumeration of aerobic 2,4-dinitroanisole-degrading bacteria in soil and water.

| S-EPMC11631463 | biostudies-literature

Synthesis and Characterization of Azido- and Nitratoalkyl Nitropyrazoles as Potential Melt-Cast Explosives.

Project description:Desirable advancements in the field of explosive materials include the development of novel melt-castable compounds with melting points ranging from 80 to 110 °C. This is particularly important due to the limited performance and high toxicity associated with TNT (trinitrotoluene). In this study, a series of innovative melt-castable explosives featuring nitratoalkyl and azidoalkyl functionalities attached to the 3-nitro-, 4-nitro-, 3,4-dinitropyrazole, or 3-azido-4-nitropyrazole scaffold are introduced. These compounds were synthesized using straightforward methods and thoroughly characterized using various analytical techniques, including single-crystal X-ray diffraction, IR spectroscopy, multinuclear nuclear magnetic resonance (NMR) spectroscopy, mass spectrometry, elemental analysis, and DTA. Furthermore, the energetic properties such as (theoretical) performance data, sensitivities, and compatibilities of the compounds were evaluated and compared among the different structures.

| S-EPMC10535347 | biostudies-literature

OmicsDI is part of the ELIXIR infrastructure

OmicsDI is an Elixir interoperability service. Learn more ›

Tweets

OmicsDI Databases

PRIDE
PeptideAtlas
MassIVE
JPOST Repository
Physiome Model Repository

EGA
EVA
ENA
LINCS
PAXDB
Cell Collective

MetaboLights
Metabolomics Workbench
MetabolomeExpress
GNPS
BioModels
FAIRDOMHub

ArrayExpress
dbGaP
ExpressionAtlas
GEO
NODE

Information

Databases
Help
API
Contact us
Code on GitHub
Terms of use
Submit Data