Method for preparing 4,4'-bis-[4-aminofurazan-3-yl-n(o)n-azoxy]-3,3'-azofurazane and its applying as thermostable explosive substance

FIELD: organic chemistry, chemical technology, explosive substances.

SUBSTANCE: invention relates to a method for preparing 4,4'-bis-[4-aminofurazan-3-yl-N(O)N-azoxy]-3,3'-azofurazane of the general formula (1):

that is a new thermostable explosive substance with improved exploitation indices. Method for preparing compound of the formula (1) involves treatment of 4,4'-diaminoazoxyfurazane with potassium bromate solution (KBrO3) in hydrochloric acid medium or its mixture with organic acid. Proposed compound can be used as a component of explosive compositions, solid rocket fuels and power-consuming compositions of different designations exploited at elevated temperatures (for example, in blast-hole drilling in depth mines).

EFFECT: improved preparing method, valuable properties of substance.

1 tbl, 2 ex

 

The present invention relates to a method for producing 4,4’-bis-[4-aminopyrazine-3-yl-N(O)N-azoxy]-3,3’-athurasya General formula (1):

and its use as a heat resistant explosives.

The proposed connection can be used as a component of the explosive compositions of solid rocket fuels and energy-intensive compositions for various purposes, operated at elevated temperatures (for example, when blasting in deep mines). The connection 1 is an intermediate for the synthesis of macromolecules and may find application in organic synthesis.

The proposed connection is a linear diamine containing four purasinovic cycle, two ethoxylate and one isogroup. The method of obtaining the compounds (1) and its properties are not described in literature. However, it is mentioned in one article as an intermediate for the synthesis of macrocycles [V.A.Eman et al., Mendeleev Commun., 1997, (1), 5-7].

A method of obtaining linear dinitrosobenzene 2, containing four purasinovic cycle, two ethoxylate and one isogroup, consisting in the oxidation of amine 3 with an aqueous solution of potassium permanganate (KMPO4in the environment of hydrochloric acid.

This oxidizing agent widely used for the synthesis of isopure the ANOVA [..Sheremetev, N.N.Makhova, W.Friedrichsen, Adv. Heterocycl. Chem., Academic Press, 2001, 78, 65-188]. However N04used only for oxidation aminopyrazine, including one amino group.

Another oxidant - dibromodecane (DBI), under the action of various diaminofurazan oxidizes both amino groups, which not only leads to intermolecular, but also intramolecular condensation. The result is the formation of macrocycles [..Sheremetev, N.N.Makhova, W.Friedrichsen, Adv. Heterocycl. Chem., Academic Press, 2001, 78, 65-188]. In particular, the processing of 4,4’-diaminoazobenzene (4) in acetonitrile DBI at room temperature leads to the formation of a mixture of macrocycle 5, characterized by the mutual location of apoximately [V.A.Eman et al., Mendeleev Commun., 1997, (1), 5-7].

To obtain the specified connection 1, since the reaction does not occur preservation of amino groups.

It is also known that the oxidation of 3,4-diaminofurazan (6) mixtures of 96% H2SO4and 30% H2O2leads to the formation of 4,4’-diaminoazobenzene (7) and amine 4. Under the action of a diamine 6 an aqueous solution of persulfate ammonium mostly obtained azo-compound 7 [Gdialog, Medborgare, Bvideos, VDDCORE, Ukr. org. chemistry, 1981, 17 (4), 861-865].

However, a mixture of 96% H2SO4and 30% H2About2may not be used for the floor is placed the target compounds 1, since the original connection 4 does not react with them.

Azo-compound 7 has also recently been obtained by the oxidation of 3,3-diaminopyrimidine (8) in a methanol solution of oxygen [D.Chavez, L.Hill, M.Hiskey, S.Kinkead.J. Energetic Mater., 2000, 18, 219-236].

However, this method cannot be used for the synthesis of the desired amine 1 due to the lack of appropriate source material.

Note also that the above methods allow only connections, including two purasinovic cycle, and ensure the formation of azo-, or azoxy-links.

The present invention is the development of ways to produce compounds, which are linear diamine containing four purasinovic cycle, which is the new heat-resistant explosive substance with improved performance characteristics.

This object is achieved by a method of obtaining 4,4’-bis-[4-aminopyrazine-3-yl-N(O)N-azoxy]-3,3’-athurasya (1), namely, that 4,4-diaminoazobenzene (4) is treated with a solution Bromeliaceae potassium (Kugo3in the environment of hydrochloric acid or its mixture with an organic acid. As organic acids can be used, for example, acetic or triperoxonane acid.

The yield of the target compounds SOS is to place 44-62%. The structure proved by data of elemental analysis, mass, IR-, NMR-spectra.

The proposed method is based on intermolecular oxidative condensation of compounds, including aminopyrazoles fragment, under the action of the one-electron oxidant, such as Kugo3in the environment of hydrochloric acid or its mixture with an organic acid, such as acetic or triperoxonane, with the formation of intermolecular azo-bond. It should be noted that the proposed conditions of oxidation lead to selective oxidation of only one amino group present in the original diamine 4.

None of the previously known methods of forming double N=N bond in the synthesis asaforesaid, including aminopropanoic fragment that has not been used for a combination of Kugo3and hydrochloric acid or its mixture with an organic acid.

It should be noted that the use as a medium for the reaction of organic acids in the absence of hydrochloric acid leads to the production of a complex mixture of substances; to allocate from this mixture the target diamine 1 is not possible.

Only a collection taken for the synthesis of compounds of formula (1) conditions and the selected source connection given the opportunity to achieve one of these goals is to obtain a linear diamine containing four purasinovic cycle, two azoxy-related and and one isogroup.

The proposed connection can be used as a component of the explosive compositions of solid rocket fuels and energy-intensive compositions for various purposes, operated at elevated temperatures (for example, when blasting in deep mines).

As the basic components of standard heat resistant explosives currently used 1,3,5-triamino-2,4,6-trinitrobenzene (TATB) and 2,2’,4,4’,6,6’-hexanitrostilbene (STS) [Energetic condensed systems. Brief encyclopedic dictionary. Edited by Bpeuropa, Ed. 2nd M: Yanus-K, 2000; J.Kohler, R.Meyer, Explosives. 4 ed., Weinheim: VCH, 1993].

As can be seen from the table, these compounds have high thermal resistance, but have average energy and explosive characteristics (heat of formation ΔH

0
f
speed of detonation D; detonation pressure PCJ). Both substances are nitro-derivatives of benzene and does not comprise fragments of heterocycles.

Known heat-resistant explosives, in which two aminopyrazole fragment linked azo - or ethoxypropane, such as 4,4-diaminofurazan (7) and 4,4-diaminoazobenzene (4) [M.A.Hiskey et al., Pat. US 6358339, Pat. US 2002/0134476]. N is though that compound 7 has an oxygen balance worse than the connection 4, the explosive characteristics of these compounds are close. This effect is due to a greater contribution of athropy in the heat of formation of compounds in comparison with ethoxypropan. Vanim property TATB, STS, and substances 4 and 7 is the low sensitivity to mechanical impact (impact and friction).

Despite the fact that compounds 4 and 7 are superior in energy performance of TATB and STS, their overall performance is lower than such a standard high explosive, as HMX [Energetic condensed systems. Brief encyclopedic dictionary. Edited by Bpeuropa, Ed. 2nd M: Yanus-K, 2000; J.Kohler, R.Meyer, Explosives. 4 ed., Weinheim: VCH, 1993]. Note, however, the high sensitivity of HMX to mechanical stress.

Table

Comparative physical and thermochemical characteristics of the claimed substances 1 analogs
TATBDPSA-5A-1HMXConnection 1
Empirical formulaC6H6N6O6C14H6N6O6C 4H4N8O2C4H4N8O3C4H8N8O8C8H4N16O6
Mol. weight258.15354.24196.13212.13296.16420.22
The nitrogen content, %32.55At 23.7257.1352.8237.8453.33
Oxygen coefficient, kO0.400.190.200.30.670.33
The density, d, g/cm31.931.741.7281.7471.91.76
So pl., °330318315248280267
Heat of formation, ΔHf0kcal/mol-36.85+12.2+128+106+17.9+237
Speed of detonation, D, km/sec780070007990802091608090
The pressure of detonation, RGJ, kbar284212274277382 298

As can be seen from the table, the characteristics of the connection 1 occupy an intermediate position between TATB and HMX and surpass the closest analogue is a substance 4.

Thus, the inventive compound is a linear diamine containing four purasinovic cycle, two ethoxylate and one isogroup, and is heat-resistant explosive (table). The presence in the structure of the claimed compounds of azo - and atxigru provides increased heat of formation compared to the reference compound 4. Connection 1 is different from the connection 4 improved oxygen balance. The sensitivity of the compounds 1 to mechanical impact (impact and friction) is similar to that of TATB, which distinguishes it from such a sensitive matter as HMX. As you can see from the table, a number of indicators connection 1 outperforms other sensitive heat-resistant substance. It should be noted that derivatives of furazan widely used in the construction of explosives, however, has not been previously used combinations of the four purasinovic cycles, two apoximately and amino groups, and one athropy.

The present invention is illustrated by the following examples.

Example 1. At room temperature to a suspension 2,12 g (10 mmol) of 4,4’-diaminophenoxy razana (4) in a mixture of salt (~50 ml) and acetic acid (~10-20 ml) with vigorous stirring was added in small portions 0,83-1,67 g (5-10 mmol) Kugo 3. After stirring the reaction mixture for 2-4 hours, it is diluted with water and the precipitate is filtered off, washed with water and recrystallized from dioxane. Obtain 1.22 g (58%) of compound 1 as a yellow-orange powder.

Mass spectrum, m/z: 420 [M+], 404 [M+-Oh], 390 [M+-NO], 374 [M+-NO-A], 337, 308, 280, 224.

IR spectrum (in KBr, νcm-1): 3440, 3335, 1650, 1510, 1490, 1440, 1380, 1270, 1190, 1050, 950, 800.

An NMR spectrum1H (DMSO-d6that δ, ppm): 6.98 (NH2).

An NMR spectrum13(DMSO-d6that δ, ppm): 144.7 (C-NNO), 148.9 (C-NH2), 149.4 (C-C-NH2), 158.7 (C-NN).

Found, %:With 22.90N 53.28N 1.00
C8H4N16O6(420.22)
Calculated, %:With 22.87N 53.33N 0.96

Example 2. To a suspension 2,12 g (10 mmol) of 4,4’-diaminoazobenzene (4) in hydrochloric acid (~450 ml) under vigorous stirring was added in small portions 0,83-1,67 g (5-10 mmol) Kugo3. After stirring the reaction mixture for 2-4 hours, it is cooled to 0-5°C, the precipitate is filtered off, washed with water and recrystallized from aqueous DMSO. Obtain 1.13 g (54%) of compound 1.

Thus, a method was developed to obtain the soedineniya, representing a linear diamine containing four purasinovic cycle, two ethoxylate and one isogroup, which is not sensitive heat-resistant explosive.

1. The way to obtain 4,4'-bis-[4-aminopyrazine-3-yl-N(0)N-azoxy]-3,3'-athurasya formula (1):

namely, that 4,4-diaminoazobenzene process solution bronovo acid potassium (Kugo3in the environment of hydrochloric acid or its mixture with an organic acid.

2. The use of 4,4'-bis-[4-aminopyrazine-3-yl-N(0)N-azoxy]-3,3'-athurasya formulas (1)

as the heat-resistant explosive.



 

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FIELD: organic chemistry, medicine.

SUBSTANCE: invention relates to new derivatives of phenylpiperazine of the formula (I): , wherein X represents 1) group of the formula (1): , wherein S1 means hydrogen, halogen atom; S2 and S3 mean independently of one another hydrogen atom, (C1-C6)-alkyl, phenyl or benzyl; S4 means two hydrogen atoms, oxo-group; S5 means hydrogen atom (H), (C1-C4)-alkyl; Y means CH2, oxygen atom (O), sulfur atom (S); or 2) group of the formula (2): , wherein S1 has above given values; R means hydrogen atom (H), (C1-C4)-alkyl, (C2-C6)-alkoxyalkyl, (C2-C4)-alkenyl or (C2-C4)-alkynyl; or 3) group of the formula (3): wherein S1 has above given values; Z means CH2, oxygen atom (O), nitrogen atom (N); or 4) group of the formula (4): , wherein S1 has above given values; or 5) group of the formula (5): , wherein S1 has above given values; A means oxygen atom (O), nitrogen atom (N) linked with piperazine ring at position 5 or 8; or 6) group of the formula (6): , wherein S1 has above given values; S6 and S7 mean hydrogen atom or oxo-group; or 7) group of the formula (7): , wherein one of dotted line can represent a double bond; S1 has above given values; P = T = Q mean nitrogen atom or P = T mean nitrogen atom; Q means CH or CH2; or P = Q mean nitrogen atom; T means CH, CH2, CH-CH3, C-CH3; or P means nitrogen atom; T means CH, CH2; Q represents sulfur atom; m = 2-6; n = 0-2; R5 and R6 mean independently of one another hydrogen atom (H), (C1-C3)-alkyl; or R5 + R6 represent group -(CH2)p- wherein p = 3-5; R7 means (C1-C3)-alkyl, (C1-C3)-alkoxy-, halogen atom, cyano-group; or R6 + R7 (R7 at position 7 of indole ring) mean group -(CH2)q wherein q = 2-4, and their salts. Compound of the formula (I) elicit high affinity both to dopamine D2-receptor and to serotonin reuptake site that allows their applying in treatment of the central nervous system diseases.

EFFECT: valuable medicinal properties of compounds.

5 cl, 3 tbl, 4 sch, 8 ex

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FIELD: organic chemistry, chemical technology, explosive substances.

SUBSTANCE: invention relates to a method for preparing 4,4'-bis-[4-aminofurazan-3-yl-N(O)N-azoxy]-3,3'-azofurazane of the general formula (1):

that is a new thermostable explosive substance with improved exploitation indices. Method for preparing compound of the formula (1) involves treatment of 4,4'-diaminoazoxyfurazane with potassium bromate solution (KBrO3) in hydrochloric acid medium or its mixture with organic acid. Proposed compound can be used as a component of explosive compositions, solid rocket fuels and power-consuming compositions of different designations exploited at elevated temperatures (for example, in blast-hole drilling in depth mines).

EFFECT: improved preparing method, valuable properties of substance.

1 tbl, 2 ex

FIELD: method of production of heat-resistant explosives used for initiation and transmission of detonation in oil-and-gas producing industry.

SUBSTANCE: proposed method includes forming the conditions for activation of interaction of 1,5-dihalide-2,4- dinitrobenzenes with 2, 4, 6-trinitrohalogenobenzenes in dichloethane medium by Ullman reaction due to introduction of equi-molecular amounts of activating additives of aprotic solvents selected from dimethyl formamide, dimethyl sulfoxide, dimethyl acetamide, N-methyl pyrrolidone, acetonitrile into reaction mass at ratio of 1-3 mole of activator to mole of 1,5-dihalide-2,4-dinitrobenzene and use of nitric acid for liberation of octanite from mixture of reaction products. Temperature for forming the target product is reduced to 83-85°C; proposed method may be used for production of chloropolynitrobenzenes at yield increased to 82% of theoretical level.

EFFECT: enhanced efficiency; increased yield of target product.

3 cl, 2 tbl, 1 ex

FIELD: chemistry.

SUBSTANCE: invention relates to organic chemistry and specifically to 3,3'-bis(fluorodinitromethyl-ONN-azoxy)-4,4'-difurazanyl ether of formula (I) . The invention also relates to a method of producing the compound of formula (I).

EFFECT: obtaining a novel compound which can be used as a fusible explosive or a fusible base for powerful explosive compounds.

3 cl, 2 tbl, 1 ex

FIELD: chemistry.

SUBSTANCE: present disclosure comprises exposing silver azide to dosed optical radiation through pretreatment of silver azide with optical radiation with wavelength of 380±10 nm and intensity in the range of 1*1014 quanta/cm2 to 2*1016 quanta/cm2 for 5-20 min. The detonator is then triggered with optical radiation energy higher than the pretreatment radiation energy.

EFFECT: invention provides more controllable use of detonators, improves stability of silver azide crystals with respect to thermal, radiation and photodecomposition and enables to maintain operational characteristics for storage periods of up to a year or longer without special measures.

1 tbl

FIELD: chemistry.

SUBSTANCE: octanite is obtained by interaction of 2,4,6-trinitrochlorobenzene with 1,5-dichloro-2,4-dinitrobenzene by Ullmann reaction in dichloroethane medium in presence of dimethylformamide. Mixture of initial 2,4,6-trinitrochlorobenzene and 1,5-dichloro-2,4-dinitrobenzene in dichloroethane solution is prepared by successive combined nitration of 2-2.2 mol of 2-nitrochlorobenzene at 140°C for 3 hours and further in the same reaction mass - 1 mol of 1,5-dichlorobenzene at 90°C for 1.5 hours with mixture, containing 98% nitric acid and 104% oleum. Dichloroethane solution is washed with water and dehydrated (dried) by distillation of azeotrope dichloroethane+water under atmospheric pressure to water content in solution not higher than 0.2% and solution density 1.32 g/cm3. To separate octanite from mixture of condensed products of Ullmann reaction sulphuric-nitric acid mixture from obtaining initial components is used.

EFFECT: invention makes it possible to create safe technological method of octanite obtaining, reduce staging, reduce amount of liquid acidic and organic wastes.

2 cl, 2 ex

FIELD: chemistry.

SUBSTANCE: present invention relates to organic chemistry, namely to poly nitro compounds derivatives chemistry, specifically to bis(fluorodinythromethyl-ONN-azoxy) azoxyfurazane of formula (I). Method of producing a compound of formula (I) consists in that bis(dinythromethyl-ONN-azoxy)azoxyfurazane of formula (II) is treated with KOH and formed corresponding dipotassium salt reacts with xenon difluoride (XeF2).

EFFECT: high-power compound, characterised by positive oxygen balance (OB) higher enthalpy of formation (ΔHfo) and higher density (d) for use as fusible explosive or fusible base for powerful explosive compounds.

2 cl, 1 tbl, 2 ex

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