Application of photo degradation for remediation of cyclic nitramine and nitroaromatic explosives

Mahbub, Parvez; Nesterenko, Pavel N.

doi:10.1039/c6ra12565d

Cited by 26 publications

(9 citation statements)

References 107 publications

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“…Detailed studies on environmental fate, transport, and effects data of these molecules are ongoing. Several methods, such as solar-induced phototransformation, alkaline hydrolysis, and metal-catalyzed reduction, − have been investigated with regard to the degradation of these compounds in the environment. It is well-known that ground state of oxygen molecule is triplet.…”

Section: Introductionmentioning

confidence: 99%

Role of Singlet Oxygen in the Degradation of Selected Insensitive Munitions Compounds: A Comprehensive, Quantum Chemical Investigation

et al. 2019

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DNAN (2,, NTO (3-nitro-1,2,4triazol-5-one), and NQ (nitroguanidine) are important energetic materials used in military applications. They may find their way to the environment during manufacturing, transportation, storage, training, and disposal. A detailed investigation of possible mechanisms for reactions of the nitrocompounds with singlet oxygen, one of the potential methods for their degradation, was performed by computational study using the PCM(Pauling)/M06-2X/6-311++G(d,p) approach. Obtained results suggest that reactivity of the investigated munitions compounds toward singlet oxygen follows the order: DNAN > NTO(anion) > NQ ≫ NTO. DNAN is involved in [4 + 2]-addition with oxygen, and further formation of diepoxide or epoxyketone through diradical intermediates have been predicted. The NTO may undergo intramolecular rearrangement with formation of peroxide compound or nitrite radical elimination, and NQ may be transformed into urea.

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Section: Introductionmentioning

confidence: 99%

Role of Singlet Oxygen in the Degradation of Selected Insensitive Munitions Compounds: A Comprehensive, Quantum Chemical Investigation

et al. 2019

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“… Mahbub and Nesterenko (2016) reported that the intramolecular hydrogen bonding within the molecule that controlled the photo adsorption of the molecule. Nitro groups that are common in energetic materials have a high adsorption of photon energy from visible and ultraviolet wavelengths.…”

Section: Ihe Wastewater Treatment Methodsmentioning

confidence: 99%

“…Nitro groups that are common in energetic materials have a high adsorption of photon energy from visible and ultraviolet wavelengths. The decomposition of nitroaromatic compounds was reported as occurring via ring cleavage as a result of the loss of a nitro group followed by subsequent decomposition into HCHO, HCOOH, NH 2 CHO, N 2 O, NO 2 - and NO 3 + ( Mahbub and Nesterenko, 2016 ).…”

Section: Ihe Wastewater Treatment Methodsmentioning

confidence: 99%

“…Photolysis has been shown to be effective in speeding the breakdown of RDX (Bordeleau et al, 2013) and therefore should also be effective at speeding the degradation of other nitroamines. Mahbub and Nesterenko (2016) reported that the intramolecular hydrogen bonding within the molecule that controlled the photo adsorption of the molecule. Nitro groups that are common in energetic materials have a high adsorption of photon energy from visible and ultraviolet wavelengths.…”

Section: Photolysismentioning

confidence: 99%

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A review of treatment methods for insensitive high explosive contaminated wastewater

Fawcett-Hirst

Temple

Ladyman

et al. 2021

Heliyon

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Insensitive high explosive materials (IHE) such as 3-nitro-1,2,4-triazol-5-one (NTO) and 2,4-dinitroanisole (DNAN) are increasingly being used in formulations of insensitive munitions alongside 1,3,5-trinitroperhydro-1,3,5-triazine (RDX). Load, assembly and packing (LAP) facilities that process munitions produce wastewater contaminated with IHE which must be treated before discharge. Some facilities can produce as much as 90,000 L of contaminated wastewater per day. In this review, methods of wastewater treatment are assessed in terms of their strengths, weaknesses, opportunities and threats for their use in production of IHE munitions including their limitations and how they could be applied to industrial scale LAP facilities. Adsorption is identified as a suitable treatment method, however the high solubility of NTO, up to 16.6 g.L À1 which is 180 times higher that of TNT, has the potential to exceed the adsorptive capacity of carbon adsorption systems. The key properties of the adsorptive materials along the selection of adsorption models are highlighted and recommendations on how the limitations of carbon adsorption systems for IHE wastewater can be overcome are offered, including the modification of carbons to increase adsorptive capacity or reduce costs.

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“…This is mainly because of usage а nitro-compounds as energetics materials Let us give just one example. In 2010, more than 12 million pounds of energetic materials were released into waterways by the US Army's Radford Ammunition Plant (Mahbub and Nesterenko 2016). Investigations of decomposition products of toxic species (including nitro-compounds) require the application of reliable techniques, In addition to different experimental methods also computational modelling has been applied to study transformations of energetic materials.…”

Section: Introductionmentioning

confidence: 99%

Decomposition of 2,4,6-Trinitrotoluene (TNT) and 5-nitro-2,4-dihydro-3H-1,2,4-triazol-3-one (NTO) by Fe13O13 Nano-particle: Density Functional Theory Study

Gorb

Ilchenko

Leszczyński

2022

Preprint

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To obtain more insight into the mechanisms of the decomposition of energetic compounds, we performed a computational study of the interaction of Fe13O13 nano-particle with two energetic molecules (2,4,6-Trinitrotoluene - TNT and 5-nitro-2,4-dihydro-3H-1,2,4-triazol-3-one - NTO). The density functional theory using M06-2X, B3LYP and BLYP density functionals has been applied. It has been found that the reactivity of these molecules strongly depends on the place of adsorption (so-called top and bottom planes of Fe13O13). Namely, only the interaction with the bottom plane results in the thermodynamic characteristics of the decomposition which provide a medium reaction rate of the studied processes. Several pathways for such a decomposition have been found. One of them is the inter-complex oxygen transfer of nitro-group oxygen to Fe13O13. This pathway results in the formation of adsorbed nitroso compounds. Second pathway describes more complex decomposition which includes the transfer of nitro-group oxygen accompanied by hydrogen transfer. In all cases, the interaction of energetic molecules with Fe13O13 nano-particle takes place along with barrier-less electron transfer from Fe13O13 to TNT or NTO species.

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Application of photo degradation for remediation of cyclic nitramine and nitroaromatic explosives

Abstract: Photo degradation is a rapid and safe remediation process and advances in continuous-flow photochemistry can scale-up yields of photo degradation.

Cited by 26 publications

References 107 publications

Role of Singlet Oxygen in the Degradation of Selected Insensitive Munitions Compounds: A Comprehensive, Quantum Chemical Investigation

Role of Singlet Oxygen in the Degradation of Selected Insensitive Munitions Compounds: A Comprehensive, Quantum Chemical Investigation

A review of treatment methods for insensitive high explosive contaminated wastewater

Decomposition of 2,4,6-Trinitrotoluene (TNT) and 5-nitro-2,4-dihydro-3H-1,2,4-triazol-3-one (NTO) by Fe13O13 Nano-particle: Density Functional Theory Study

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