Catalyzed Nitration of Amines: I. Dinitroxydiethylnitramine

Herring, K. G.; Toombs, L. E.; Wright, George F; Chute, W. J.

doi:10.1139/cjr48b-011

Cited by 20 publications

(4 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Nitration of cellulose in liquid CO 2 .Adapted from Ref. [176] Environmentally benign green processes for the manufacturing of these energetic ingredients and materials are highly desirable to reduce the huge amount of toxic wastes which are treated, disposedo f, or otherwise released into the environment in existing HEM production processes. [172] HMX (VOD % 9110 ms À1 , d = 1.90 gcm À3 )i samore powerful explosive than RDX because of its higher density.H owever,i ti sc haracterized by ah igherp roduction cost than RDX and is currently appliedinunique propellants and explosive formulations.…”

Section: N-nitrationreactionsmentioning

confidence: 99%

“…= 51 8C) powerful explosive (VOD % 7580 ms À1 ), can be melt-cast readily into charges. [176] Environmentally benign green processes for the manufacturing of these energetic ingredients and materials are highly desirable to reduce the huge amount of toxic wastes which are treated, disposedo f, or otherwise released into the environment in existing HEM production processes.…”

Section: N-nitrationreactionsmentioning

confidence: 99%

See 1 more Smart Citation

Prospective Symbiosis of Green Chemistry and Energetic Materials

et al. 2017

View full text Add to dashboard Cite

A global increase in environmental pollution demands the development of new "cleaner" chemical processes. Among urgent improvements, the replacement of traditional hydrocarbon-derived toxic organic solvents with neoteric solvents less harmful for the environment is one of the most vital issues. As a result of the favorable combination of their unique properties, ionic liquids (ILs), dense gases, and supercritical fluids (SCFs) have gained considerable attention as suitable green chemistry media for the preparation and modification of important chemical compounds and materials. In particular, they have a significant potential in a specific and very important area of research associated with the manufacture and processing of high-energy materials (HEMs). These large-scale manufacturing processes, in which hazardous chemicals and extreme conditions are used, produce a huge amount of hard-to-dispose-of waste. Furthermore, they are risky to staff, and any improvements that would reduce the fire and explosion risks of the corresponding processes are highly desirable. In this Review, useful applications of almost nonflammable ILs, dense gases, and SCFs (first of all, CO ) for nitration and other reactions used for manufacturing HEMs are considered. Recent advances in the field of energetic (oxygen-balanced and hypergolic) ILs are summarized. Significant attention is paid to the SCF-based micronization techniques, which improve the energetic performance of HEMs through an efficient control of the morphology and particle size distribution of the HEM fine particles, and to useful applications of SCFs in HEM processing that makes them less hazardous.

show abstract

Section: N-nitrationreactionsmentioning

confidence: 99%

Section: N-nitrationreactionsmentioning

confidence: 99%

Prospective Symbiosis of Green Chemistry and Energetic Materials

et al. 2017

View full text Add to dashboard Cite

show abstract

“…Another important azetidine structure is 1 H -3,3-dinitroazetidine (DNAZ), 8,9 which is also a precursor for TNAZ preparation. 10,11 Compared with TNAZ because the nitrogen atom in azetidine is easily protonated, DNAZ tends to exist in the cationic form, making it easy to form ionic salts with other anions. 12,13 In addition, DNAZ is prone to nucleophilic addition reaction with electron deficient reagents, 14 N -nitrosation, 15 and even the Mannich condensation reaction under some conditions.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and characterization of potential polycyclic energetic materials using bicyclic triazole and azetidine structures as building blocks

Yang

Jia²,

Miao

et al. 2023

RSC Adv.

View full text Add to dashboard Cite

show abstract

“…The disadvantage of the synthesis route in Scheme is the separation of the O-nitration and N-nitration processes, which results in the formation of large amounts of the dangerous intermediate DIA . It has been experimentally determined by Zhou that the thermal stability of DIA is lower than that of DINA .…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Optimization, and Thermal Risk Analysis of One-Pot N-Nitrodiethanolamine Dinitrate Synthesis

Feng²,

Hao³

et al. 2019

Org. Process Res. Dev.

View full text Add to dashboard Cite

N-Nitrodiethanolamine dinitrate (DINA) is a nitramine explosive containing both O-nitro and N-nitro groups. In this work, the synthesis of DINA by nitration of diethanolamine hydrochloride (DEAHC) with the fuming nitric acid/acetic anhydride (HNO3/Ac2O) system was developed and optimized. It was found that large amounts of acetic anhydride and low reaction temperature are favorable to the yield of DINA. When the DEAHC:HNO3:Ac2O molar ratio was 1:4.5:6 and the initial reaction temperature was decreased to 5 °C, the yield of DINA reached ∼92%. The thermal risk of this synthesis route was also analyzed. The value of T D24 for the final reaction mixture was calculated to be 61.9 °C, which is significantly higher than the MTSR for the synthesis process. This indicates that as long as the addition immediately stops in case of the cooling failure scenario, decomposition of the formed DINA will not occur. The above analysis shows that the DINA synthesis approach reported here is favorable in terms of both productivity and safety.

show abstract

Catalyzed Nitration of Amines: I. Dinitroxydiethylnitramine

Cited by 20 publications

References 0 publications

Prospective Symbiosis of Green Chemistry and Energetic Materials

Prospective Symbiosis of Green Chemistry and Energetic Materials

Synthesis and characterization of potential polycyclic energetic materials using bicyclic triazole and azetidine structures as building blocks

Synthesis, Optimization, and Thermal Risk Analysis of One-Pot N-Nitrodiethanolamine Dinitrate Synthesis

Contact Info

Product

Resources

About