CN103121977A - Diazo(N-dinitryl ethyl) furazan energy-containing ionic salts and preparation method thereof - Google Patents
Diazo(N-dinitryl ethyl) furazan energy-containing ionic salts and preparation method thereof Download PDFInfo
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Abstract
The invention relates to diazo(N-dinitryl ethyl) furazan energy-containing ionic salts and a preparation method thereof, and belongs to the technical field of energy-containing materials. The synthetic method comprises the following steps of: performing acid-base neutralization reaction of diazo(N-dinitryl ethyl) furazan and 2 times of organic base in mole to obtain corresponding energy-containing ionic salts or performing reaction of diazo(N-dinitryl ethyl) furazan sylvite with 2 times of hydrochloride in mole of corresponding cations; and filtering the precipitate to obtain the target product. The synthetic method provided by the invention is simple and easy to industrialize. 6 energy-containing ionic salts are better in thermal stability, the calculated detonation performance of the energy-containing ionic salts is far superior to that of TNT (Trinitrotoluene), and the detonation performance of part of compounds is approximate to that of RDX (Cyclotrimethylene Trinitramine). The diazo(N-dinitryl ethyl) furazan energy-containing ionic salts can be used as substituents of a nitroform explosive and a furazan explosive for improving oxygen balance in a mixed explosive and used as an oxygen supply component in a propellant.
Description
Technical field
The present invention relates to weight (N-dinitrobenzene ethyl) furazan class and contain energy ion salt and preparation method thereof, belong to the energetic material technical field.
Background technology
Must satisfy requirement (fiery explosive journal, 2005,28 (4): 9-13) of high-energy-density, low vulnerability and environmental compatibility as the energetic material of weapon energy carrier.Yet these performances are always conflicting to a certain extent: good stability, and the common energy of the material that sensitivity is low is lower, and when energy was higher, chemical physical stability again can variation.At present, the development of energetic material is from hanging down to seeking novel high-energy the new stage of feeling explosive take pure pursuit high-energy as main material, in the urgent need to having the energetic material (energetic material of the high comprehensive performances such as high energy, insensitiveness, stable, toxicological harmless, 2010,18 (4): 467-475).
High nitrogen contains in recent years can ion salt become one of focus of high Energy Density Materials research field, compare them has steam and forces down (the toxicity steam that produces in the course of processing is little) with its molecule analogue, density is high, the advantages such as Heat stability is good (chemical progress, 2009,21 (1): 152-163), using the high negatively charged ion of nitrogen content and positively charged ion can obtain having containing of higher Enthalpies of Formation and density can ion salt, this be because they contain contain in a large number can N-N and C-N key.In addition, high nitrogen compound decomposition mainly generates nitrogen, and this makes them become the material standed for that environmentally friendly high energy material is used.The preliminary study of the developed countries such as the U.S. shows, high nitrogen energy-containing compound is one of most promising high Energy Density Materials, and in synthetic high nitrogen compound, the correlative study of the high nitrogen compound of non-ionic type has accounted for the overwhelming majority.In fact, the high nitrogen of ionic contains and can salt more has superiority than the neutral high nitrogen compound of non-ionic type, because they are tending towards presenting lower vapour pressure and the density of Geng Gao, and stable aspect and Heat of Formation aspect are than higher (the Shaanxi Normal University's journal of neutral congener, 2010,38 (3): 43-49).
Furazan occupies critical role in biological chemistry, as: the NO donor under physiological conditions, antitumor and anticancer agent, they also play an important role in energetic material equally.Furazan class explosive has higher density and good detonation property usually, as Isosorbide-5-Nitrae, and 5,8-tetranitro-Isosorbide-5-Nitrae, 5,8-four azepine hydrogenated naphthalene-2,3-and furazan (density 1.89gcm
-3, explosion velocity 7582ms
-1), Isosorbide-5-Nitrae, 6-trinitro--Isosorbide-5-Nitrae, 6-three azepans-2,3-and furazan (density 1.86gcm
-3, explosion velocity 8697ms
-1Although) etc. energy very high, its higher sensitivity has become one of major reason that limits its practical application.Nitroform series explosive has very high energy equally, and wherein the weight of representative aliphatics chain structure (2,2,2-Trinitroethyl-N nitro) quadrol, be commonly called as 2
#Explosive (density 1.87gcm
-3, explosion velocity is 8970ms
-1) and heavy (2,2,2-Trinitroethyl) nitramine, be commonly called as 6
#Number explosive, (density 1.97gcm
-3, explosion velocity is 8657ms
-1) advantage of such explosive is that synthetic method is simple, energy and explosion velocity are higher, but owing to containing nitramine and nitroform group in such molecular structure of compounds, make its sensitivity higher, and thermostability is undesirable.Because susceptibility and the thermolability of this compounds are stopped using now.It is the undesirable property of explosive for nitroform, we change the nitroform group into geminal dinitro at design, form like this two C-H that are connected with geminal dinitro, the strong electron attraction of nitro makes C-H have certain acidity, contains the energy ion salt thereby can generate with multiple alkali reaction.Add the high Enthalpies of Formation of furazan ring, introduce the furazan ring and can improve detonation property.Contain the energy ion salt non-volatile under field conditions (factors), the processing problem when having avoided coexisting with solid material.In addition, due to the coulomb electrostatic interaction, ionic compound has the density higher than molecule compound, and this makes them all have more orderly structure in solid phase or liquid phase (ion pair), can improve the mechanical property of material.Introduce the nitrogen content that the high positively charged ion of nitrogen content has not only improved salt, make its one-tenths large-minded, the few cigarette of products of combustion, and can improve the Enthalpies of Formation of salt, the detonation propertys such as the while can corresponding raising explosion velocity, detonation pressure.
The invention relates to weight (N-dinitrobenzene ethyl) furazan class and contain energy ion salt and preparation method thereof, can be used as nitroform series explosive as 2
#, 6
#The surrogate of explosive and furazan class explosive is used for pyrotechnic composition and improves oxygen balance, and as oxygen-supplying component in propelling agent.
Summary of the invention
The purpose of this invention is to provide weight (N-dinitrobenzene ethyl) furazan class and contain energy ion salt properity and preparation method thereof, obtained the rich nitrogen energetic material that a class has better thermostability.
The objective of the invention is to be achieved through the following technical solutions:
Heavy (N-dinitrobenzene ethyl) of the present invention furazan class contains the energy ion salt, and its general formula is as follows:
Heavy (N-dinitrobenzene ethyl) of the present invention furazan class contains and can ion salt realize by following route:
The preparation of heavy (N-dinitrobenzene ethyl) furazan sylvite
Ion salt synthetic route one:
Its concrete preparation process is as follows:
To weigh (N-dinitrobenzene ethyl) furazan sylvite adds and is dissolved as the light yellow clarifying liquid body in pure water, then under stirring at room, add wherein respectively two times of a small amount of water-soluble guanidinesalt hydrochlorates of molar equivalent, one aminoguanidine monohydrochloride, triaminoguanidine hydrochloride, N-guanylurea hydrochloride, separate out the light yellow solid precipitation, reaction mixture continues stirring at room 1h, filters light-yellow precipitate and uses frozen water and each washed twice of methyl alcohol, and solid is dry 2h in the drying at room temperature device.
Ion salt synthetic route two:
Its concrete preparation process is as follows:
To weigh (N-dinitrobenzene ethyl) furazan sylvite and add and be dissolved as the light yellow clarifying liquid body in pure water, add a certain amount of CH
2Cl
2Solvent transfers to acidity with dilute hydrochloric acid with mixing solutions, makes heavily (N-dinitrobenzene ethyl) furazan sylvite neutral molecule that dissociates, the mixing solutions separatory, and organic phase washes with water 2 times.Then under stirring at room, add respectively 3 of the hydrazine hydrate of two times of molar equivalents and a small amount of dissolve with methanol in the organic phase, 4,5-triamino-1,2, the 4-triazole, separate out the light yellow solid precipitation, reaction mixture continues stirring at room 1h, filters light-yellow precipitate and uses frozen water and each washed twice of methyl alcohol, and solid is dry 2h in the drying at room temperature device.
Advantage of the present invention is:
1) synthesized in the present invention six kinds contain can ion salt density higher, between 1.71-1.94gcm
3Between.
2) its explosion velocity is between 7720-9131ms as calculated for the energy ion salt that contains in the present invention, and detonation pressure is between 25.5-38.7GPa, and the part detonation property of part salt is better than RDX, and is suitable with HMX, may as the surrogate of HMX, be the high-energy-density explosive.
3) such salt synthetic method is simple, mild condition, and productive rate is high, and product need not just can obtain sterling through the purge process of complexity, is easy to industrialization.
Embodiment
The preparation (1) of embodiment 1 weight (N-dinitrobenzene ethyl) furazan sylvite
Take dinitrobenzene potassium ethylate 1.74g (10mmol), stir about 5min under room temperature, still have major part not molten, take diamino furazan 510mg (5.1mmol) and join in reaction solution, be warming up to 40 ℃ of reactions, almost all dissolvings of solid after about half an hour, solution becomes yellow settled solution, continue reaction 24h, filter the solid product methanol wash.Get solid 1.96g, productive rate 95%.
Its structural formula is as follows:
Decomposition temperature: 166 ℃ (DSC).
1H?NMR(400MHz，d
6-DMSO)：δ＝4.577(d，2H)，δ＝6.191(t，1H)ppm；
13C?NMR(100MHz，d
6-DMSO)：δ＝152.13，134.94，45.14ppm；IR(KBr?pellet)：3324，3189，1591，1458，1338，1289，1191，1113，751，666cm
-1；elemental?analysis(％)calcd?for?C
6H
6K
2N
8O
9(411.95)：C?17.48，H?1.47，N?27.17；found：C?17.35，H?1.46，N?27.23。
The preparation (2) of embodiment 2 weights (N-dinitrobenzene ethyl) furazan guanidinesalt
Add heavy (N-dinitrobenzene ethyl) furazan sylvite and the 5mL H of 412mg (1.0mmol) in 25mL single port flask
2O is dissolved as the light yellow clarifying liquid body, then under stirring at room, adds wherein to be dissolved in 2mL H
2Guanidinesalt hydrochlorate 190mg (2.0mmol) in O, the light yellow solid precipitation is separated out in the stirring at room reaction, reaction mixture continues stirring at room 1h, filters light-yellow precipitate and uses frozen water and each washed twice of methyl alcohol, and solid is dry 2h in the drying at room temperature device, get the 438mg product, productive rate is 96%.
In following embodiment, NM reaction conditions is identical with embodiment 2.
Its structural formula is as follows:
Decomposition temperature: 172 ℃ (DSC).Density is 1.719g cm
-3 1H?NMR(400MHz，d
6-DMSO)：δ＝7.171(s，12H，NH
2)，δ＝6.220(t，2H，NH)，δ＝4.601(d，4H，CH
2)ppm；
13C?NMR(100MHz，d
6-DMSO)：δ＝158.368，149.567，132.261，42.701ppm；IR(KBr?pellet)：3387，3181，3101，1699，1661，1600，1471，1339，1320，1289，1205，1115，961，937，750，668cm
-1；elemental?analysis(％)calcd?for?C
8H
18N
14O
9(454.14)：C?21.15，H?3.99，N?43.16；found：C?20.97，H?3.86，N?42.89。
Embodiment 3 weights (N-dinitrobenzene ethyl) furazan 3,4,5-triamino-1,2, the preparation of 4-triazolium salt (3)
Add heavy (N-dinitrobenzene ethyl) furazan sylvite and the 5mL H of 412mg (1.0mmol) in 25mL single port flask
2O is dissolved as the light yellow clarifying liquid body, adds approximately 10ml CH
2Cl
2Solvent transfers to acidity with dilute hydrochloric acid with mixing solutions, makes heavily (N-dinitrobenzene ethyl) furazan sylvite neutral molecule that dissociates, the mixing solutions separatory, and organic phase washes with water 2 times.Take 3,4,5-triamino-1,2,4-triazole 228mg (2.0mmol) is dissolved in methyl alcohol, and this methanol solution is added drop-wise to above-mentioned isolated CH
2Cl
2Mutually, after stir about 5min, have immediately light yellow solid to separate out under room temperature, continue to stir 1h, filter light-yellow precipitate and use frozen water and each washed twice of methyl alcohol, solid is dry 2h in the drying at room temperature device, gets the 500mg product, and productive rate is 88%.
Its structural formula is as follows:
Decomposition temperature: 143 ℃ (DSC).Density is 1.885g cm
-3 1H?NMR(400MHz，d
6-DMSO)：δ＝6.994(s，8H，NH
2)，δ＝6.184(t，2H，NH)，δ＝5.554(s，4H，NH2)，δ＝4.548(d，4H，CH
2)ppm；
13C?NMR(100MHz，d
6-DMSO)：δ＝150.035，149.570，132.174，42.747ppm；IR(KBr?pellet)：3387，3179，3114，1702，1662，1599，1468，1338，1321，1290，1206，1117，750，668cm
-1；elemental?analysis(％)calcd?for?C
10H
20N
20O
9(564.17)：N?49.63，H?3.57，C?21.28；found：C?21.20，H?3.52，N?49.56。
The preparation (4) of embodiment 4 weights (N-dinitrobenzene ethyl) furazan one aminoguanidine salt
Condition only changes guanidinesalt into one aminoguanidine salt with embodiment 2, and output is 450mg, and productive rate is 93%.
Its structural formula is as follows:
Decomposition temperature: 152 ℃ (DSC).Density is 1.720g cm
-3 1HNMR(400MHz，d
6-DMSO)：δ＝8.567(s，1H，NH)，δ＝7.232(s，2H，NH
2)，δ＝6.740(s，2H，NH
2)，δ＝6.192(t，?1H，NH)，δ＝4.664(d，2H，NH
2)，δ＝4.556(d，4H，CH
2)ppm；
13C?NMR(100MHz，d
6-DMSO)：δ＝158.795，149.589，132.242，42.736ppm；IR(KBr?pellet)：3386，3321，3188，1661，1617，1592，1464，1338，1292，1188，1115，751，666cm
-1；elemental?analysis(％)calcd?for?C
8H
20N
16O
9(484.16)：C?19.84，H?4.16，N?46.27；found：C?19.52，H?3.99，N?45.95。
The preparation (5) of embodiment 5 weights (N-dinitrobenzene ethyl) furazan triamino guanidinesalt
Condition only changes guanidinesalt into the triaminoguanidine hydrochloride with embodiment 2, and output is 530mg, and productive rate is 97%.
Its structural formula is as follows:
Decomposition temperature: 154 ℃ (DSC).Density is 1.728g cm
-3 1H?NMR(400MHz，d
6-DMSO)：δ＝8.568(s，6H，NH)，δ＝6.189(t，2H，NH)，δ＝4.555(d，4H，CH
2)，δ＝4.471(d，12H，NH
2)ppm；
13C?NMR(100MHz，d
6-DMSO)：δ＝159.046，149.578，132.223，42.740ppm；IR(KBr?pellet)：3322，3195，1588，1462，1353，1289，1239，1185，1116，850，751cm
-1；elemental?analysis(％)calcd?for?C
8H
24N
20O
9(544.20)：C?17.65，H?4.44，N?51.46；found：C?17.58，H?4.25，N?50.99。
The preparation (6) of embodiment 6 weights (N-dinitrobenzene ethyl) furazan N-guanylurea salt
Condition only changes the guanidinesalt hydrochlorate into N-guanylurea hydrochloride with embodiment 2, and output is 530mg, and productive rate is 98%.
Its structural formula is as follows:
Decomposition temperature: 153 ℃ (DSC).Density is 1.784g cm
-3 1H?NMR(400MHz，d
6-DMSO)：?δ＝9.671(s，2H，NH)，δ＝8.017(s，8H，NH
2)，δ＝7.114(s，4H，NH
2)，δ＝6.171(t，2H，NH)，δ＝4.549(d，4H，CH
2)ppm；
13C?NMR(100MHz，d
6-DMSO)：δ＝155.583，154.680，149.570，132.174，42.736ppm；IR(KBr?pellet)：3422，3135，1716，1692，1603，1471，1339，1320，1289，1205，1115，961，937，750，668cm
-1；elemental?analysis(％)calcd?for?C
10H
20N
16O
11(540.15)：C?22.23，H?3.73，N?41.47；found：C?21.65，H?3.90，N40.42。
The preparation (7) of embodiment 7 weights (N-dinitrobenzene ethyl) furazan hydrazonium salt
Condition is with embodiment 3, and only with 3,4,5-triamino-1,2, the 4-triazole changes hydrazine hydrate into, and output is 393mg, and productive rate is 98%.
Its structural formula is as follows:
Decomposition temperature: 128 ℃ (DSC).Density is 1.944g cm
-3 1H?NMR(400MHz，d
6-DMSO)：δ＝6.217(t，2H，NH)，δ＝5.897(6H，NH)，δ＝4.742(s，4H，NH)，δ＝4.557(d，4H，CH
2)ppm；
13C?NMR(100MHz，d
6-DMSO)：δ＝149.590，132，233，42.738ppm；IR(KBr?pellet)：3322，3197，1669，1589，1458，1339，1289，1186，1114，957，933，848，751cm
-1；elemental?analysis(％)calcd?for?C
6H
16N
12O
9(400.12)：C?18.00，H?4.03，N41.99；found：C?17.56，H?3.98，N?41.03。
Table 1 adopts document J.Phys.Chem.C. for the prediction detonation property that contains the energy ion salt involved in the present invention, and the method in 2010,114,13142-13152 is calculated, and wherein density is actual density.
Table 1 contains the prediction detonation property of energy ion salt
Claims (5)
1. weight (the N-dinitrobenzene ethyl) furazan that can be used for the energetic material field contains the energy ion salt, and it has following structure:
2. the synthetic method of heavy (N-dinitrobenzene ethyl) according to claim 1 furazan sylvite, it is characterized in that: the dinitrobenzene potassium ethylate is dissolved in pure water, then add the diamino furazan, be warming up to 40-60 ℃, reacting by heating 12-24 hour, in above-mentioned reaction, the mol ratio of dinitrobenzene potassium ethylate and diamino furazan was 2: 1.1-2: 1.5; Temperature of reaction is 40-60 ℃.
3. the synthetic method of heavy (N-dinitrobenzene ethyl) according to claim 2 furazan sylvite, it is characterized in that: reaction solvent is H
2O； Reaction times is 12-24 hour; The mol ratio of dinitrobenzene potassium ethylate and diamino furazan is 2: 1.1-2: 1.5; Temperature of reaction is 40-60 ℃.
4. heavy (N-dinitrobenzene ethyl) according to claim 1 furazan contains the synthetic method of energy ion salt, it is characterized in that: (1) heavy (N-dinitrobenzene ethyl) furazan and corresponding alkali are at methyl alcohol or ethanol or CH
2Cl
2After middle reaction 1-2h, remove by filter solvent and namely get the corresponding energy ion salt that contains; Or (2) heavy (N-dinitrobenzene ethyl) furazan sylvite react 1-2h with corresponding hydrochloride in water after, filter out precipitated product and namely get the corresponding energy ion salt that contains.
5. heavy (N-dinitrobenzene ethyl) according to claim 4 furazan contains the synthetic method of energy ion salt, it is characterized in that: reaction solvent can be CH when heavy (N-dinitrobenzene ethyl) furazan and alkali direct reaction
2Cl
2, methyl alcohol or ethanol; Metal-salt used (N-dinitrobenzene ethyl) furazan sylvite of attaching most importance to when preparing ion salt by replacement(metathesis)reaction; Reaction times is 1-2h.
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| CN104447762A (en) * | 2014-12-08 | 2015-03-25 | 北京理工大学 | Energetic ionic salts of 7-nitryl-4-ketone-4,8-dihydro-[1,2,4] triazole [5,1-d] [1,2,3,5] tetrazine-2-oxide and preparation method of energetic ionic salt |
| CN108440563A (en) * | 2018-03-22 | 2018-08-24 | 中国工程物理研究院化工材料研究所 | Two furazano piperazine bistetrazoles ion salt containing energy and its synthetic method |
| CN109970676A (en) * | 2017-12-28 | 2019-07-05 | 南京理工大学 | Three nitre ethylaminos join furazan and its synthetic method |
| CN110790719A (en) * | 2018-08-03 | 2020-02-14 | 南京理工大学 | Fluorine dinitro ethylamino bifurazan compound and synthetic method thereof |
| CN115260177A (en) * | 2022-07-29 | 2022-11-01 | 北京理工大学 | 4, 5-diamino-2- ((4-amino-1, 2, 5-oxadiazole-3-yl) methyl) -2, 4-dihydro-3H-1, 2, 4-triazole-3-imine nitrate and synthesis method and application thereof |
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| CN108440563A (en) * | 2018-03-22 | 2018-08-24 | 中国工程物理研究院化工材料研究所 | Two furazano piperazine bistetrazoles ion salt containing energy and its synthetic method |
| CN110790719A (en) * | 2018-08-03 | 2020-02-14 | 南京理工大学 | Fluorine dinitro ethylamino bifurazan compound and synthetic method thereof |
| CN115260177A (en) * | 2022-07-29 | 2022-11-01 | 北京理工大学 | 4, 5-diamino-2- ((4-amino-1, 2, 5-oxadiazole-3-yl) methyl) -2, 4-dihydro-3H-1, 2, 4-triazole-3-imine nitrate and synthesis method and application thereof |
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