Nitrolysis of Hexamethylenetetramine: Iii. Preparation of Pure Cyclonite

Brockman, Fred J.; Wright, George F; Downing, D. C.

doi:10.1139/cjr49b-049

Cited by 37 publications

(15 citation statements)

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“…Synthesis of TNX. Hexahydro-1,3,5-trinitroso-1,3,5-triazine (TNX) was prepared by the method of Brockman et al (3). The crude product was recrystallized twice from 95% ethanol and then from benzene to give 4.8 g of yellow needles (mp 105 to 107°C; literature 105 to 107°C).…”

Section: Methodsmentioning

confidence: 99%

Biodegradation of Hexahydro-1,3,5-Trinitro-1,3,5-Triazine

McCormick

Cornell

Kaplan

1981

Appl Environ Microbiol

278

143

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Biodegradation of the explosive hexahydro-1,3,5-trinitro-1,3,5-triazine (RDX) occurs under anaerobic conditions, yielding a number of products, including: hexahydro-1-nitroso-3,5-dinitro-1,3,5-triazine, hexahydro-1,3-dinitroso-5-nitro-1,3,5-triazine, hexahydro-1,3,5-trinitroso-1,3,5-triazine, hydrazine, 1,1-dimethyl-hydrazine, 1,2-dimethylhydrazine, formaldehyde, and methanol. A scheme for the biodegradation of RDX is proposed which proceeds via successive reduction of the nitro groups to a point where destabilization and fragmentation of the ring occurs. The noncyclic degradation products arise via subsequent reduction and rearrangement reactions of the fragments. The scheme suggests the presence of several additional compounds, not yet identified. Several of the products are mutagenic or carcinogenic or both. Anaerobic treatment of RDX wastewaters, which also contain high nitrate levels, would permit the denitrification to occur, with concurrent degradation of RDX ultimately to a mixture of hydrazines and methanol. The feasibility of using an aerobic mode in the further degradation of these products is discussed.

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Section: Methodsmentioning

confidence: 99%

Biodegradation of Hexahydro-1,3,5-Trinitro-1,3,5-Triazine

McCormick

Cornell

Kaplan

1981

Appl Environ Microbiol

278

143

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“…Mono-and trinitroso-RDX derivatives were synthesized according to the methods described by Brockman et al (1949). Stock solutions of RDX and HMX, labeled and unlabeled, were prepared in acetone.…”

Section: Chemicalsmentioning

confidence: 99%

Enhanced Biodegradation and Fate of Hexahydro-1,3,5-Trinitro-1,3,5-Triazine (RDX) and Octahydro-1,3,5,7-Tetranitro-1,3,5,7-Tetrazocine (HMX) in Anaerobic Soil Slurry Bioprocess

Shen

Hawari

Ampleman

et al. 2000

Bioremediation Journal

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Enhanced Biodegradation and Fate of Hexahydro-1,3,5-Trinitro-1 ,3,5-Triazine (RDX) and Octahydro-1,3,5,7-Tetranitro-1 ,3,5,7-Tetrazocine (HMX) in Abstract: Native soil microbial populations and unadapted municipal anaerobic sludges were compared for nitramine explosive degradation in microcosm assays under various conditions. Microbial populations from an explosive-contaminated soil were only able to mineralize 12% hexahydro-l,3,5-trinitro-l,3,5-triazine (RDX) (at a concentration of 800 mg/kg slurry) or 4% octahydro-l,3,5,7-tetranitro-l,3,5,7-tetrazocine (HMX) (at a concentration of 267 mg/kg slurry). In contrast, municipal anaerobic sludges were able to mineralize them to carbon dioxide, with efficiencies of up to 65%. Reduction of RDX and HMX into their corresponding nitroso-derivatives was notably faster than their mineralization. The biodegradation of HMX was typically delayed by the presence of RDX in the microcosm, confirming RDX is used as an electron acceptor preferentially to HMX. The laboratoryscale bioslurry reactor reproduced the results of the microcosm assays, yet with much higher RDX and HMX degradation rates. A radiolabel-based mass balance in the soil slurry indicated that, besides a significant mineralization to carbon dioxide, 25% and 31% of RDX and HMX, respectively, appeared as acetonitrile-extractable metabolites, while the remaining part was incorporated into biomass and irreversibly bound to the soil matrix. About 10% of the HMX derivatives were estimated to be chemically bound to the soil matrix, while for RDX the estimation was nil.

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“…After the second treatment under these conditions, the desired tri-Nnitroamine (cyclonite) was formed from the di-N-nitroamine in 75% yield. 69 Interestingly, the authors reported the failure of peroxymonosulfuric acid (Caro's acid), potassium chlorate, or hypochlorite to promote the desired oxidation.…”

Section: ■ Reductive Nitrosamine Chemistrymentioning

confidence: 82%

Nitrosamine Reactivity: A Survey of Reactions and Purge Processes

Borths

Burns

Curran

et al. 2021

Org. Process Res. Dev.

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Drug recalls have led to increased regulatory scrutiny into the formation and presence of nitrosamine (Nnitrosoamine) impurities in medicines. This review aims to assist the development of risk mitigation strategies by summarizing known reactions of nitrosamines, with a focus on reactions useful within the context of complex molecule synthesis. This review should serve as a useful reference and help lead to the development of chemical processes which effectively control nitrosamines.

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Nitrolysis of Hexamethylenetetramine: Iii. Preparation of Pure Cyclonite

Cited by 37 publications

References 0 publications

Biodegradation of Hexahydro-1,3,5-Trinitro-1,3,5-Triazine

Biodegradation of Hexahydro-1,3,5-Trinitro-1,3,5-Triazine

Enhanced Biodegradation and Fate of Hexahydro-1,3,5-Trinitro-1,3,5-Triazine (RDX) and Octahydro-1,3,5,7-Tetranitro-1,3,5,7-Tetrazocine (HMX) in Anaerobic Soil Slurry Bioprocess

Nitrosamine Reactivity: A Survey of Reactions and Purge Processes

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