Alkaline hydrolysis pathway of 2,4-dinitroanisole verified by 18O tracer experiment

Chun-lei, Wang; Wallace, Adam F.; Heraty, Linnea J.; Qi, Haiping; Sturchio, Neil C.

doi:10.1016/j.jhazmat.2020.122627

Cited by 12 publications

(15 citation statements)

References 35 publications

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“…In the current study, control experiments (i.e., carried out in the absence of UV light and/or peroxide at near neutral pH) confirmed that DNAN hydrolysis did not occur (Figure A3). However, previous studies carried out under alkaline conditions showed that the pseudo first‐order rate constants for DNAN hydrolysis were comparable to those reported in the current study (Wang et al, 2020). Wang et al (2020) observed DNAN hydrolysis, 2,4 DNP production, and a pseudo first‐order rate constant of 0.345 h −1 at a pH of 12.…”

Section: Resultssupporting

confidence: 91%

“…However, previous studies carried out under alkaline conditions showed that the pseudo first‐order rate constants for DNAN hydrolysis were comparable to those reported in the current study (Wang et al, 2020). Wang et al (2020) observed DNAN hydrolysis, 2,4 DNP production, and a pseudo first‐order rate constant of 0.345 h −1 at a pH of 12. Production of 2,4 DNP is faster under alkaline conditions.…”

Section: Resultssupporting

confidence: 91%

“…In principle, 2,4 DNP can be produced via DNAN hydrolysis (Wang et al, 2020). In the current study, control experiments (i.e., carried out in the absence of UV light and/or peroxide at near neutral pH) confirmed that DNAN hydrolysis did not occur (Figure A3).…”

Section: Resultsmentioning

confidence: 99%

See 2 more Smart Citations

2,4‐dinitroanisole transformation during advanced oxidation with ultraviolet light emitting diodes and hydrogen peroxide

Burdsall

Schober

Stubbs

et al. 2022

Water & Environment J

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This study investigated the kinetics and reaction mechanisms associated with advanced oxidation of 2,4-dinitroanisole (DNAN) with light emitting diodes (LEDs) in the UV/H 2 O 2 process. The pseudo first-order reaction rate constants for DNAN oxidation depended on the H 2 O 2 /DNAN molar ratio and were between 0.017 and 0.026 min À1 .Hydroxyl radical scavenging was strongly implicated by the experimental results. High mass spectrophotometric chromatograms showed the presence of several by-products, including three with ecotoxicity that is greater than that of DNAN. Transformation pathways were analysed using Density Functional Theory (DFT), which helped to predict the presence of experimentally detected DNAN by-products by considering Mulliken charges. This study is the first to elucidate DNAN transformation mechanisms using both experimental studies and computational chemistry.

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Section: Resultssupporting

confidence: 91%

Section: Resultssupporting

confidence: 91%

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2,4‐dinitroanisole transformation during advanced oxidation with ultraviolet light emitting diodes and hydrogen peroxide

Burdsall

Schober

Stubbs

et al. 2022

Water & Environment J

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“…Hydrolysis and Proposed Nitro-Reduction Pathways of DNAN a a Enzymatic and alkaline hydrolysis mechanisms were resolved in previous studies. 42,43…”

Section: Environmental Implicationsmentioning

confidence: 99%

Carbon and Nitrogen Isotope Fractionations During Biotic and Abiotic Transformations of 2,4-Dinitroanisole (DNAN)

Wang,

Fuller,

Murillo-Gelvez

et al. 2024

Environ. Sci. Technol.

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2,4-Dinitroanisole (DNAN) is a main constituent in various new insensitive munition formulations. Although DNAN is susceptible to biotic and abiotic transformations, in many environmental instances, transformation mechanisms are difficult to resolve, distinguish, or apportion on the basis solely of analysis of concentrations. We used compound-specific isotope analysis (CSIA) to investigate the characteristic isotope fractionations of the biotic (by three microbial consortia and three pure cultures) and abiotic (by 9,10-anthrahydroquinone-2-sulfonic acid [AHQS]) transformations of DNAN. The correlations of isotope enrichment factors (Λ N/C ) for biotic transformations had a range of values from 4.93 ± 0.53 to 12.19 ± 1.23, which is entirely distinct from Λ N/C values reported previously for alkaline hydrolysis, enzymatic hydrolysis, reduction by Fe 2+ -bearing minerals and iron-oxide-bound Fe 2+ , and UV-driven phototransformations. The Λ N/C value associated with the abiotic reduction by AHQS was 38.76 ± 2.23, within the range of previously reported values for DNAN reduction by Fe 2+ -bearing minerals and iron-oxide-bound Fe 2+ , albeit the mean Λ N/C was lower. These results enhance the database of isotope effects accompanying DNAN transformations under environmentally relevant conditions, allowing better evaluation of the extents of biotic and abiotic transformations of DNAN that occur in soils, groundwaters, surface waters, and the marine environment.

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“…Various emerging treatment strategies have been investigated for IHEs. For example, electrochemical reduction, chemical reduction using bimetallic and zerovalent iron particles, − biological degradation, − photochemical degradation, , alkaline hydrolysis, and advanced oxidation processes (AOPs) , have been applied to treat aqueous DNAN solutions. While these studies demonstrated DNAN destruction to varying extents, several of the treatment strategies have serious drawbacks.…”

Section: Introductionmentioning

confidence: 99%

Electrochemical Destruction of Insensitive High Explosives Using Magnéli Phase Titanium Oxide Reactive Electrochemical Membranes

Islam,

Chaplin

2024

ACS EST Eng.

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Magnéli phase Ti4O7 reactive electrochemical membranes (REMs) were studied for the oxidation of insensitive high explosives, specifically 2,4-dinitroanisole (DNAN) and nitroguanidine (NQ). At a potential of 3.2 V/SHE for DNAN and 3.8 V/SHE for NQ, >99.7% removal of both compounds was achieved with a hydraulic residence time of ∼11 s. The pseudo-first-order rate constants were 38 min–1 for DNAN and 8.5 min–1 for NQ. Using 20 mM NQ and 0.62 mM DNAN as synthetic munitions wastewater, a three-stage reactor achieved 99.995% NQ removal, and ∼100% of DNAN was mineralized in a single stage. However, electrochemical oxidation of NQ caused electrode blocking and inhibition of NQ removal over time. Testing different background electrolytes revealed that in situ generated reactive chlorine species reacted with NQ and prevented electrode blocking, resulting in 97.2% removal during 3.5 h of continuous treatment. Based on experimental results and density functional theory simulations, it was concluded that the initial oxidation step for NQ was direct electron transfer (DET) and for DNAN was a combination of DET and reaction with OH•. Furthermore, cyanamide was likely the key intermediate during NQ oxidation that led to electrochemical polymerization reactions that blocked the electrode surface.

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Alkaline hydrolysis pathway of 2,4-dinitroanisole verified by 18O tracer experiment

Cited by 12 publications

References 35 publications

2,4‐dinitroanisole transformation during advanced oxidation with ultraviolet light emitting diodes and hydrogen peroxide

2,4‐dinitroanisole transformation during advanced oxidation with ultraviolet light emitting diodes and hydrogen peroxide

Carbon and Nitrogen Isotope Fractionations During Biotic and Abiotic Transformations of 2,4-Dinitroanisole (DNAN)

Electrochemical Destruction of Insensitive High Explosives Using Magnéli Phase Titanium Oxide Reactive Electrochemical Membranes

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