ChemInform Abstract: Chemistry of Urea Nitro Derivatives. Part 1. Synthesis of N,N′‐Dinitrourea.

Lobanova, A. A.; Sataev, R. R.; Popov, N. I.; Il’yasov, S. G.

doi:10.1002/chin.200049091

Cited by 6 publications

(25 citation statements)

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“…We have previously reported 7, 8 the synthesis of N , N ′‐dinitrourea by nitrating urea with an anhydrous nitric‐sulfuric acid mixture (50/50) made by mixing calculated quantities of 97–98 % nitric acid and oleum (20 % SO 3 ). The monitoring of the urea nitration reaction by UV spectroscopy shows that dinitrourea is formed quantitatively.…”

Section: Resultsmentioning

confidence: 99%

“…In the first case, bis(hydroxymethyl)nitramine was derived by the technique reported in the literature 6: a reaction mixture prepared by nitration of urea 7, 8 was directly diluted with water followed by hydrolysis of N , N ′‐dinitrourea in the presence of excess formaldehyde (over 4 M ) at 0–60 °C, with the water layer being extracted with ethyl acetate. The oily product yield constituted 56–60 % calculated as 2 M 1,3‐dihydroxy‐2‐nitrazapropane from 1 M dinitrourea.…”

Section: Resultsmentioning

confidence: 99%

“…Urea (10 g, 0.167 M ) was added in portions upon stirring at a temperature between −5 and 0 °C to 40 mL of a mixed acid (50 wt‐% nitric acid and 50 wt‐% sulfuric acid, d =1.756 g cm −3 ) prepared from oleum (20 % SO 3 ) and 97 % nitric acid. After holding for 40 min at 0–5 °C, the reaction mixture was cooled to −5 °C 7, 8, trifluoroacetic acid (40 mL) was poured, and the mixture was cooled to −15 °C and held for 15 min. The resultant precipitate was collected on a Schott funnel, washed with trifluoroacetic acid (40 mL), and dried in vacuo for 30 min.…”

Section: Methodsmentioning

confidence: 99%

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Preparation of 1,3‐Diazido‐2‐Nitro‐2‐Azapropane from Urea

Il’yasov¹,

Danilova²

2012

Propellants Explo Pyrotec

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An alternative method to prepare 1,3‐diazido‐2‐nitro‐2‐azapropane (DANP), a promising liquid component for high‐energy condensed systems, is suggested and involves the following stages: (i) nitration of urea, (ii) condensation of the nitration product with formaldehyde, (iii) acylation (chlorination) of 1,3‐dihydroxy‐2‐nitro‐2‐azapropane, (iv) chlorination of 1,3‐diacetoxy‐2‐nitro‐2‐azapropane, and (v) azidation of the dichloro derivative to DANP. This synthesis method is selective and enables isolation of 1,3‐diazido‐2‐nitrazapropane devoid of impurities.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

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Preparation of 1,3‐Diazido‐2‐Nitro‐2‐Azapropane from Urea

Il’yasov¹,

Danilova²

2012

Propellants Explo Pyrotec

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“…18.8.22 Acyclic and Cyclic Ureas 18.8.22.13.1 Synthesis of N-Nitroso-and N-Nitroureas Nitration of urea is achieved by using a mixture of nitric and sulfuric acid. Under appropriate conditions, this procedure can also be used to prepare N,N¢-dinitrourea [325] or dinitro derivatives of N-alkylureas. [326] The chemistry of these mostly unstable compounds has been investigated.…”

Section: Synthesis Of N-carbamimidoylureasmentioning

confidence: 99%

Acyclic and Cyclic Ureas (Update 2013)

Banert¹,

Dobbs²,

Hall³

et al. 2013

Knowledge Updates 2013/3

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“…Spectral characteristics of the obtained compound correspond to those described in literature. 2 4,5 Dihydroxy 1,3 dinitroimidazolidin 2 one (2). An aque ous solution of glyoxal (40%, 6 mL, 41 mmol) was added to a suspension of DNU (5.2 g, 35 mmol) in trifluoroacetic acid (20 mL) with intensive stirring and ice cooling.…”

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confidence: 99%

Synthesis of 4,5-dihydroxy-1,3-dinitroimidazolidin-2-one

2009

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A convenient method for the synthesis of 4,5 dihydroxy 1,3 dinitroimidazolidin 2 one from N,N´ dinitrourea is developed.Key words: 4,5 dihydroxy 1,3 dinitroimidazolidin 2 one, N,N´ dinitrourea, synthesis. N,N´ Dinitrourea (1, DNU) is a high energy com pound with high density (1.98 g cm -3 ) and low thermal stability. It can be used as a precursor of other high energy compounds with the DNU fragment, for example, di and tetranitroglycolurils. The following information for DNU has been reported: flash point 147-149 °С, decomposi tion temperature 138-148 °С, spontaneous ignition in air is possible at room temperature; 1 m.p. 107-110 °С (ethyl acetate); 2 fast decomposition at 120 °С (DSC), greater impact and friction sensitivity in comparison with hexo gen, 3 temperature of the onset of decomposition is 90 °С, and X ray data. 4 The use of the method 2 for the DNU synthesis (nitra tion of urea with a mixture of nitric and sulfuric acids followed by filtration and washing with dichloromethane), does not allow one to obtain pure DNU (the DNU sample contains up to 20% of sulfuric acid). The attempt to re produce the other method for the DNU synthesis (nitra tion of urea with a mixture of nitric and sulfuric acids followed by washing with trifluoroacetic acid) 3 resulted in a yield that was approximately 2.5 times lower (27%) than the yield reported 3 (67%) (a method for DNU synthesis analogous to the method mentioned 3 was also used in the other investigation, 4 the yield was 40%). All the described methods 2-4 are similar to each other in nitration time (1-3 h) and temperature (0-5 °С), but differ in the ureanitric-sulfuric acid mixture ratio, and also in relative amounts of nitric acid (relative to urea).We developed a method for the synthesis of DNU that allows one to obtain the product with properties that are well reproducible (some of them are described 5 ), and in relatively high yield (64%). Oleum (20%) was used instead of sulfuric acid in the proposed method. 4,5 Dihydroxy 1,3 dinitroimidazolidin 2 one (2) is the condensation product of dinitrourea with glyoxal, it has good oxygen balance and lower impact and friction sensitivity in comparison with DNU. This compound has two free positions (hydroxy groups) for further functional ization, therefore, it can be used as a building block for the introduction of 1,3 dinitroimidazolidin 2 one fragment into molecules of organic compounds. The method for its synthesis from DNU and glyoxal described in the litera ture 6 leads to low yields of the target compound (41.7%). Nitration of 4,5 dihydroxy 2 nitroiminoimidazoline gives compound 2 in 30% yield. 7The use of crude DNU (as obtained using the method described earlier 6 and containing up to 20% of sulfuric acid) might be one of the reasons of the low yield of 2 from DNU. We assumed that the use of pure DNU would posi tively affect the yield of the target product. Initial efforts of the synthesis of compound 2 from pure DNU and aque ous glyoxal were unsuccessful -the hydrolytic decompo sition of DNU has occurred (appare...

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ChemInform Abstract: Chemistry of Urea Nitro Derivatives. Part 1. Synthesis of N,N′‐Dinitrourea.

Cited by 6 publications

References 0 publications

Preparation of 1,3‐Diazido‐2‐Nitro‐2‐Azapropane from Urea

Preparation of 1,3‐Diazido‐2‐Nitro‐2‐Azapropane from Urea

Acyclic and Cyclic Ureas (Update 2013)

Synthesis of 4,5-dihydroxy-1,3-dinitroimidazolidin-2-one

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