Synthesis and thermal behavior of 4,5-dihydroxyl-2-(dinitromethylene)-imidazolidine (DDNI)

Xu, Kangzhen; Chen, Yong-Shun; Wang, Min; Luo, Jinan; Song, Jirong; Zhao, Fengqi; Hu, Rong‐Zu

doi:10.1007/s10973-010-1244-4

Cited by 26 publications

(12 citation statements)

References 39 publications

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“…reported that although using hafnium triflate as a Lewis acid catalyst, the acylation of FOX‐7 with acetyl chloride only yields 23 % of a monoacylated product (Scheme b), and FOX‐7 can react with N ‐chlorosuccinimide to yield a chlorinated product (Scheme c); Xu et al. reported that FOX‐7 can react with glyoxal to undergo nucleophilic addition reactions resulting in the formation of a five‐number ring (Scheme d); and Axthammer et al. reported that FOX‐7 can undergo a nucleophilic addition reaction with an extremely activated isocyanate, chlorosulfonyl isocyanate, to form a urea derivative (Scheme e) …”

Section: Introductionmentioning

confidence: 99%

“…[3][4][5][6][7][8][9][10][11][12][13] A lot of new energetic derivatives of FOX-7 have been reported continually in the past 20 years. [14][15][16][17][18][19][20][21][22][23][24][25][26][27][28] Molecular structure of FOX-7 is very simple, only containing two amino groups and two nitro groups connected with an ethylene group, but its reactivity is abundant, which have been systematically summarized in a review by our group. [29] FOX-7 is a good example of a 'push-pull' alkene of the nitroenamine type, possessing a highly polarized C=C double bond whose positive and negative charges are stabilized by two amino groups and two nitro groups respectively, [30] so it presents both electrophilicity and nucleophilicity.…”

Section: Introductionmentioning

confidence: 99%

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Aromatic Nucleophilic Substitution of FOX‐7: Synthesis and Properties of 1‐Amino‐1‐Picrylamino‐2,2‐Dinitroethylene (APDE) and Its Potassium Salt [K(APDE)]

Feng

Wang

et al. 2019

ChemPlusChem

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Two energetic compounds, 1‐amino‐1‐picrylamino‐2,2‐dinitroethylene (APDE) and its potassium salt [K(APDE)] were synthesized through an aromatic nucleophilic substitution reaction between FOX‐7 and picryl chloride. APDE and K(APDE) were characterized by elemental analysis, IR, NMR spectroscopy, and X‐ray diffraction. APDE has a 3D wavy layered stacking structure similar to FOX‐7. K(APDE) (peak temperature (Tip)=185.6 °C and impact sensitivity (IS)=19.6 J) presents better stability than APDE (tap=133.3 °C and IS=15.7 J). The reasons why the stability of APDE is lower than that of FOX‐7 and picryl chloride are analyzed. The detonation velocity (D) and detonation pressure (P) of APDE (8.36 km s−1 and 31.3 Gpa) are close to those of FOX‐7 and RDX. The thermal decomposition of K(APDE) is very violent, and its detonation performance (D=9.14 km s−1 and P=38.6 Gpa) is comparable to that of HMX, indicating that K(APDE) has good potential to be a high explosive.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Aromatic Nucleophilic Substitution of FOX‐7: Synthesis and Properties of 1‐Amino‐1‐Picrylamino‐2,2‐Dinitroethylene (APDE) and Its Potassium Salt [K(APDE)]

Feng

Wang

et al. 2019

ChemPlusChem

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“…[1][2][3][4][5] Many researches have been carried out on the synthesis, mechanism, molecule structure, theoretical calculation, derivative, thermal behavior, explosive performance and application of FOX-7, 1-25 which has been an active field all along. In our studies, [26][27][28][29][30][31] a new eletrophilic derivative of FOX-7, 4,5-dihydroxyl-2-(dinitromethylene)-imidazolidine (DDNI) was synthesized, which was found to be a good intermediate to synthesize other new valuable energetic compounds due to its two ortho-hydroxyl groups. 31 So, we synthesized a new energetic compound, 4,5-diacetoxyl-2-(dinitromethylene)imidazolidine (DADNI), by the reaction of DDNI with acetic anhydride.…”

Section: Introductionmentioning

confidence: 99%

“…In our studies, [26][27][28][29][30][31] a new eletrophilic derivative of FOX-7, 4,5-dihydroxyl-2-(dinitromethylene)-imidazolidine (DDNI) was synthesized, which was found to be a good intermediate to synthesize other new valuable energetic compounds due to its two ortho-hydroxyl groups. 31 So, we synthesized a new energetic compound, 4,5-diacetoxyl-2-(dinitromethylene)imidazolidine (DADNI), by the reaction of DDNI with acetic anhydride. In the paper, the synthesis, crystal structure and thermal behavior of DADNI were reported.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Crystal Structure and Thermal Behavior of 4,5‐Diacetoxyl‐2‐(dinitromethylene)‐imidazolidine

Wang

Zhang

et al. 2011

Chin. J. Chem.

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A new energetic material, 4,5-diacetoxyl-2-(dinitromethylene)-imidazolidine (DADNI), was synthesized by the reaction of 4,5-dihydroxyl-2-(dinitromethylene)-imidazolidine (DDNI) and acetic anhydride, and characterized by single crystal X-ray diffraction. Crystal data for DADNI are monoclinic, space group C2/c, a＝15.9167R 1 ＝0.0565 and wR 2 ＝0.1649. Thermal decomposition behavior of DADNI was studied and an intensely exothermic process was observed. The kinetic equation of the decomposition reaction is: 16.64 3/ 4 d 10 4 d α α T β ＝ . exp(-1.582×10 5 /RT). The critical temperature of thermal explosion is 163.76 ℃. The specific heat capacity of DADNI was studied with micro-DSC method and theoretical calculation method. The molar heat capacity is 343.30 J•mol -1 •K -1 at 298.15 K. The adiabatic time-to-explosion of DADNI was calculated to be 87.7 s.

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“…(6)-(7). 18,26,[29][30][31][32][33] Table 3. The values of T0, Te, Tp, ΔHd, T00, Te0 and Tp0 of G(AHDNE) at various heating rates Table 4.…”

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confidence: 99%

Structural and Thermal Characteristics of a High-Nitrogen Energetic Material: G(AHDNE)

Lu¹,

Xu²,

Zhang³

et al. 2012

Bulletin of the Korean Chemical Society

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A high-nitrogen energetic salt, 1-amino-1-hydrazino-2,2-dinitroethylene guanidine salt [G(AHDNE)], was synthesized by reacting of 1-amino-1-hydrazino-2,2-dinitroethylene (AHDNE) and guanidine hydrochloride in sodium hydroxide aqueous solution. The theoretical investigation on G(AHDNE) was carried out by B3LYP/ 6-311+G* method. The thermal behaviors of G(AHDNE) were studied with DSC and TG-DTG methods, and the result presents an intense exothermic decomposition process. The enthalpy, apparent activation energy and pre-exponential constant of the process are −1060 J g , respectively. The critical temperature of thermal explosion of G(AHDNE) is 152.63 °C. The specific heat capacity of G(AHDNE) was studied with micro-DSC method and theoretical calculation method, and the molar heat capacity is 314.69 J mol −1 K −1 at 298.15 K. Adiabatic time-to-explosion of G(AHDNE) was calculated to be a certain value between 60-72 s. The detonation velocity and detonation pressure were also estimated. G(AHDNE) presents good performances.

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Synthesis and thermal behavior of 4,5-dihydroxyl-2-(dinitromethylene)-imidazolidine (DDNI)

Cited by 26 publications

References 39 publications

Aromatic Nucleophilic Substitution of FOX‐7: Synthesis and Properties of 1‐Amino‐1‐Picrylamino‐2,2‐Dinitroethylene (APDE) and Its Potassium Salt [K(APDE)]

Aromatic Nucleophilic Substitution of FOX‐7: Synthesis and Properties of 1‐Amino‐1‐Picrylamino‐2,2‐Dinitroethylene (APDE) and Its Potassium Salt [K(APDE)]

Synthesis, Crystal Structure and Thermal Behavior of 4,5‐Diacetoxyl‐2‐(dinitromethylene)‐imidazolidine

Structural and Thermal Characteristics of a High-Nitrogen Energetic Material: G(AHDNE)

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