CN103936593A - 2, 4, 6-trinitro-1, 3-bis (2', 4'-dinitrobenzene vinyl) benzene as well as preparation method and application thereof - Google Patents
2, 4, 6-trinitro-1, 3-bis (2', 4'-dinitrobenzene vinyl) benzene as well as preparation method and application thereof Download PDFInfo
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Abstract
The invention discloses an unknown compound 2, 4, 6-trinitro-1, 3-bis (2', 4'-dinitrobenzene vinyl) benzene as well as a preparation method and an application thereof. The chemical structure of the compound is characterized in that three nitryl groups exist on sites 2, 4, 6 of a middle benzene ring of 1, 3-distyryl benzene, and ortho-positions and para-positions of benzene rings at the two sides are respectively connected to the nitryl groups. The coupling constant of toluylene double bonds in a nuclear magnetic resonance spectrum is about 16.45Hz, and therefore, the compound is recognized as an anti-form structure. The compound is synthesized by three-step reaction. The preparation method is simple to operate, mild in reaction conditions and relatively high in yield. The compound has relatively good heat resistance and belongs to the field of energetic materials.
Description
Technical field
The present invention relates to a kind of unknown compound, be specifically related to a kind of compound 2,4,6-trinitro--1,3-bis-(2 ', 4 '-dinitrobenzene vinyl) benzene, preparation and application thereof.
Background technology
Many nitros stilbenes compound is the very important chemical intermediate of one, can be widely used in the field of nonlinear optics and the heat-resisting energetic material of high energy.For example it can be used for synthesizing new part for nonlinear optical material and as the high temperature powder of military and civilian.Wherein, the significant picryl sulfide base of performance ethene (HNS) belongs to the one in many nitros stilbenes compound, it is yellow crystals, and fusing point, up to 317 DEG C, is a kind of high temperature powder, there is good physics, chemical stability, mechanical sensitivity is low, insensitive to static sparking, and radiation resistance is strong, by first being made by the K.G.Shipp of Swede the sixties in last century, being widely used in the field such as oilfield exploitation and aerospace.
Document (G.X.Wang, C.H.Shi, X.D.Gong, H.M.Xiao, J.Phys.Chem.A2009,113,1318) by theoretical research the performances such as the structure of many nitro toluylenes derivative, density, detonation parameter, such material shows very strong applicability.Document (Z.G.FengandB.R.Chen, Prop., Explos., Pyrotech., 1991,16,12; Z.G.FengandB.R.Chen, Prop., Explos., Pyrotech.1992,17,237; L.Q.Wang, Y.H.Liu, J.G.Zhang, T.L.Zhang, L.Yang, X.J.Qiao, X.C.HuandJ.Y.Guo, Chin.J.
Chem.2007,25,1044,) also report the compound that has synthesized a series of many nitro toluylenes, such compounds property is superior, simultaneously owing to having two keys, whole molecular system has stronger conjugative effect, thereby can promote the fusing point of this compounds, i.e. resistance toheat.So there is extremely important status and meaning compound synthetic that builds many nitros diphenylethlene class novel under other conjugated system.And along with the introducing of more nitro functions, can significantly improve its density (energy) and corresponding heat resisting temperature.
Summary of the invention
The object of the present invention is to provide a kind of many nitros stilbenes compound 2,4,6-trinitro--1,3-bis-(2 ', 4 '-dinitrobenzene vinyl) benzene, preparation and application thereof.
Realizing the object of the invention technical scheme is:
A kind of new compound: 2,4,6-trinitro--1,3-bis-(2 ', 4 '-dinitrobenzene vinyl) benzene, its chemical structural formula of this compound is:
Above-claimed cpd 2,4,6-trinitro--1, the synthetic method of 3-bis-(2 ', 4 '-dinitrobenzene vinyl) benzene, comprises the following steps:
The first step: 2,4,6-trinitro--1,3-bis-(2 '-nitrostyrolene base) benzene synthetic
First prepare aceticanhydride-concentrated nitric acid mixed reaction solution, drip a small amount of vitriol oil as catalyzer to reaction solution, under room temperature, slowly add 2,4,6-trinitro--1,3-bis-(styryl) benzene, treat that solid all dissolves, be swift in response, reaction solution has been poured in frozen water mixed solution, had yellow-green colour solid to produce, filter, washing, dry, it is for subsequent use that recrystallization obtains product;
Second step: 2,4,6-trinitro--1,3-bis-(2 ', 4 '-dinitrobenzene vinyl) benzene synthetic
Second step is obtained 2,4,6-trinitro--1,3-bis-(2 '-nitrostyrolene base) benzene is dissolved in the vitriol oil, under low temperature, slowly drip nitrosonitric acid, stirring reaction under room temperature, pours reaction solution in frozen water mixed solution into after reaction finishes, separate out solid, dry, recrystallization obtains target product.
Wherein, in the first step, preparing concentrated nitric acid mass concentration in aceticanhydride-concentrated nitric acid mixed solution is 65～68%.
Concentrated nitric acid and 2,4,6-trinitro--1 in aceticanhydride-concentrated nitric acid mixed solution in the first step, the mol ratio of 3-bis-(styryl) benzene is 5:1, the reaction times is 5～10min, 10～45 DEG C of temperature.
In second step 2,4,6-trinitro--1, the mol ratio of 3-bis-(2 '-nitrostyrolene base) benzene and nitrosonitric acid is 1:4, the reaction times is 1～3h.
Above-claimed cpd 2,4,6-trinitro--1, the application of 3-bis-(2 ', 4 '-dinitrobenzene vinyl) benzene, described this compound is for the synthesis of heat-resisting energetic material.
Compared with prior art, its remarkable advantage is in the present invention: (1) synthesizes a kind of novel many nitros stilbenes compound 2,4,6-trinitro--1, and 3-bis-(2 ', 4 '-dinitrobenzene vinyl) benzene, this melting point compound is all higher than 226 DEG C.(2) this material also can further be introduced nitro, thereby synthesizes the heat resistant type energetic material that has more potentiality, and this material can be used for energetic material field; (3) in nitrifying process, the first step selects aceticanhydride/nitric acid system to carry out ortho position selective nitration, and second step selects nitric acid/sulfuric acid system to introduce the nitro of contraposition, and by the selection of nitrating agent, selectivity is introduced nitryl group.(4) provide the synthetic method of this material, described method is simple to operate simultaneously, reaction conditions gentleness, and productive rate is higher.
Brief description of the drawings
Fig. 1 is product 2,4 of the present invention, 6-trinitro--1, the hydrogen nuclear magnetic resonance of 3-bis-(2,4 '-dinitrobenzene vinyl) benzene
Collection of illustrative plates, X-coordinate is chemical shift.
Fig. 2 is product 2,4 of the present invention, 6-trinitro--1, the nuclear magnetic resonance of carbon of 3-bis-(2 ', 4 '-dinitrobenzene vinyl) benzene
Collection of illustrative plates, X-coordinate is chemical shift.
Fig. 3 is product 2,4 of the present invention, 6-trinitro--1, the mass-spectrogram of 3-bis-(2 ', 4 '-dinitrobenzene vinyl) benzene.
Fig. 4 is product 2,4 of the present invention, 6-trinitro--1, and the hydrogen nuclear magnetic resonance collection of illustrative plates of 3-bis-(2-nitrostyrolene base) benzene,
X-coordinate is chemical shift.
Embodiment
Below in conjunction with drawings and Examples, the present invention is described in further detail.
A kind of synthetic 2,4,6-trinitro--1, the method for 3-bis-(2 ', 4 '-dinitrobenzene vinyl) benzene, comprises the following steps:
(1) 2,4,6-trinitro--1,3-bis-(2 '-nitrostyrolene base) benzene synthetic
Reaction equation is:
Concrete steps are as follows:
First prepare aceticanhydride-salpeter solution, the nitric acid of 65-68% (8.0mL) is slowly added drop-wise in the aceticanhydride of 15mL, control temperature lower than 40 DEG C, and then 2 sulphuric acid catalysis of dropping, under room temperature, slowly add 2,4,6-trinitro--1,3-bis-(styryl) benzene (0.50g, 1.2mmol), treat that solid all dissolves, temperature rises on a small quantity, form uniform solution, stopped reaction after 5 minutes.Reaction solution is poured in 20mL frozen water mixed solution, had yellow-green colour solid to produce, filter, washing, dry, then obtain product 2,4 with acetone recrystallization, and 6-trinitro--1,3-bis-(2 '-nitrostyrolene base) benzene, for subsequent use.
(2) 2,4,6-trinitro--1,3-bis-(2 ', 4 '-dinitrobenzene vinyl) benzene synthetic
Reaction equation is:
Concrete steps are as follows:
Get previous step ortho position nitration product 2,4,6-trinitro--1,3-bis-(2 '-nitrostyrolene base) benzene (1.0g, 2.0mmol) is dissolved in the 15mL vitriol oil, form turbid solution, (0 DEG C) slowly drips nitrosonitric acid 5mL at low temperatures, and darkening of solution, stirs under room temperature 1 hour, then this mixed solution is poured in the trash ice of 150g, separated out faint yellow solid.By thick product ethanol-acetone recrystallization, obtain product 2,4,6-trinitro--1,3-bis-(2 ' 4 '-dinitrobenzene vinyl) benzene 0.59g, productive rate 50%.
Embodiment 1
First prepare aceticanhydride-salpeter solution, the nitric acid of 65-68% (8.0mL) is slowly added drop-wise in the aceticanhydride of 15mL, control temperature lower than 40 DEG C, and then 2 sulphuric acid catalysis of dropping, under room temperature, add 2,4,6-trinitro--1,3-bis-(styryl) benzene (0.50g, 1.2mmol), treat that solid all dissolves, temperature rises on a small quantity, but control temperature lower than 45 DEG C, stopped reaction after 5 minutes.Reaction solution is poured into during 20mL frozen water mixes, had solid to produce, filter, washing, dry, then obtain product 0.52g with acetone recrystallization, and productive rate 85%, for subsequent use.
1hNMR (500MHz, DMSO-d
6), δ 9.07(s, 1H), 8.09(d, J=8.15Hz, 2H), 7.86(d, J=3.95Hz, 2H) and, 7.69-7.66(m, 4H), 7.50(d, J=16.45Hz, 2H) and, 7.21(d, J=16.45Hz, 2H), 3.34(s, H
2o); (as shown in Figure 4)
Get previous step mono-nitration product 0.50g(1.0mmol) be dissolved in the 15mL vitriol oil, form turbid solution, then at low temperatures (0 DEG C) slowly drips nitrosonitric acid 5mL, the color of solution deepens gradually, continue at room temperature to stir 1 hour stopped reaction, then this mixed solution is poured in the trash ice of 150g, separated out faint yellow solid.By thick product ethanol-acetone recrystallization, obtain product 2,4,6-trinitro--1,3-bis-(2 ', 4 '-dinitrobenzene vinyl) benzene 0.32g, productive rate 55%.
Faint yellow solid, fusing point: 226-227 DEG C, IR (ν, cm
-1): 3098,1625,1608,1555,1530,1342,970;
1hNMR (500MHz, DMSO-d
6), δ 9.10(s, 1H), 8.79(d, J=2.30Hz, 2H), 8.66-8.64(dd, J
1=2.30Hz, J
2=8.65Hz, 2H), 8.11(d, J=8.65Hz, 2H), 7.73(d, J=16.45Hz, 2H) and, 7.26(d, J=16.45Hz, 2H), 3.35(s, H2O); (as shown in Figure 1)
13cNMR (126MHz, DMSO-d6), δ 149.57,147.00,146.82,146.71,135.27,129.95,129.58,129.38,127.63,125.33,122.61,119.80.(is as shown in Figure 2)
Mass spectrum molecular ion peak is: (M+Na) 620.0, (M+K) 636.0(is as shown in Figure 3)
The chemical structure characteristic of this compound is: 2,4,6 on the middle phenyl ring of 1,3-diphenylethyllene benzene have three nitros, and is respectively connected with a nitro in ortho position on the phenyl ring of both sides and contraposition.From nuclear magnetic spectrogram, the coupling constant of the two keys of toluylene is approximately 16.0Hz, confirms as transconfiguration.
Embodiment 2
First prepare aceticanhydride-salpeter solution, the nitric acid of 65-68% (12.0mL) is slowly added drop-wise in the aceticanhydride of 35mL, control temperature lower than 40 DEG C, and then 4 sulphuric acid catalysis of dropping, under room temperature, add 2,4,6-trinitro--1,3-bis-(styryl) benzene (1.50g, 3.6mmol), treat that solid all dissolves, temperature rises on a small quantity, but control temperature lower than 45 DEG C, stopped reaction after 5 minutes.Reaction solution is poured into during 40mL frozen water mixes, had solid to produce, filter, washing, dry, then obtain product 1.48g, productive rate 85% with acetone recrystallization
Embodiment 3
Equally, prepare 2,4,6-trinitro--1 according to the method for example 1,3-bis-(2 '-nitrostyrolene base) benzene is for subsequent use.
Get previous step mono-nitration product 2,4,6-trinitro--1,3-bis-(2 '-nitrostyrolene base) benzene 0.50g(1.0mmol) be dissolved in the 15mL vitriol oil, form turbid solution, then at room temperature slowly drip nitrosonitric acid 5mL, the color of solution deepens gradually, temperature rise, with water-bath control temperature be 25 DEG C, continue at room temperature to stir 1 hour stopped reaction, then this mixed solution is poured in the trash ice of 150g, separate out faint yellow solid.By thick product ethanol-acetone recrystallization, obtain product 2,4,6-trinitro--1,3-bis-(2 ', 4 '-dinitrobenzene vinyl) benzene 0.22g, productive rate 38%.
Embodiment 4
Equally, prepare 2,4,6-trinitro--1 according to the method for example 1 before, 3-bis-(2 '-nitrostyrolene base) benzene is for subsequent use.Get previous step mono-nitration product 2,4,6-trinitro--1,3-bis-(2 '-nitrostyrolene base) benzene 1.50g(3.0mmol) be dissolved in the 25mL vitriol oil, form turbid solution, then at low temperatures (0 DEG C) slowly drips nitrosonitric acid 10mL, and the color of solution deepens gradually, temperature rise, with water-bath control temperature be 25 DEG C, continue at room temperature to stir 1 hour stopped reaction, then this mixed solution is poured in the trash ice of 200g, separate out faint yellow solid.By thick product ethanol-acetone recrystallization, obtain product 2,4,6-trinitro--1,3-bis-(2 ', 4 '-dinitrobenzene vinyl) benzene 0.80g, productive rate 45%.Embodiment 5
Equally, prepare 2,4,6-trinitro--1 according to the method for example 1,3-bis-(2 '-nitrostyrolene base) benzene is for subsequent use.
First prepare nitric-sulfuric acid solution, nitrosonitric acid 5mL be slowly added drop-wise in the 15mL vitriol oil, with ice-water bath control temperature be 0 DEG C of left and right.Again by adjacent nitro product 2,4,6-trinitro--1,3-bis-(2 '-nitrostyrolene base) benzene 0.50g(1.0mmol) slowly join in nitric-sulfuric acid solution, solid adds and is completed into red turbid solution, then be placed in room temperature and stir 1h, then this mixed solution is poured in the trash ice of 150g, separate out faint yellow solid.By thick product ethanol-acetone recrystallization, obtain product 2,4,6-trinitro--1,3-bis-(2 ', 4 '-dinitrobenzene vinyl) benzene 0.70g, productive rate 38%.
Comparative example
This compounds adopts traditional Knoevenagel condensation reaction to synthesize conventionally, such as 2,4,6-trinitro--1,3-diphenylethyllene benzene derivative is with 2,4,6-trinitro-m-xylene and various substituted benzaldehyde are raw material, with benzene, as solvent, organic base catalytic reacts and prepares for 48 hours under reflux temperature.(being shown in Org.Prep.Proced.Int.1995,27,475) still adopts the method to pass through 2,4,6-trinitro-m-xylene and 2,4-dinitrobenzal-dehyde is that raw material carrys out directly synthetic this target product of a step, and experiment is found to react hardly.
Compound 2,4,6-trinitro--1,3-bis-(2 ', 4 '-dinitrobenzene vinyl) benzene structural formula is as follows:
Proposed by the invention 2,4,6-trinitro--1,3-bis-(2 ', 4 '-dinitrobenzene vinyl) benzene is the one in many nitros stilbenes compound, from structure, whole molecule has three phenyl ring, and two two keys, are intended to introduce multiple phenyl ring, expand the conjugated system of whole molecule, make it have very strong conjugative effect; There are seven nitros containing energy group simultaneously, measure gained melting point substance higher than 226 DEG C, so this material can be served as one heat-resisting energetic material effectively.
Claims (6)
1. a compound 2,4,6-trinitro--1,3-bis-(2 ', 4 '-dinitrobenzene vinyl) benzene, is characterized in that its chemical structural formula of this compound is:
2. a compound 2,4,6-trinitro--1, the preparation method of 3-bis-(2 ', 4 '-dinitrobenzene vinyl) benzene, is characterized in that comprising the following steps:
The first step: 2,4,6-trinitro--1,3-bis-(2 '-nitrostyrolene base) benzene synthetic
First prepare aceticanhydride-concentrated nitric acid mixed reaction solution, drip several vitriol oils as catalyzer to reaction solution, under room temperature, slowly add 2,4,6-trinitro--1,3-bis-(styryl) benzene, treat that solid all dissolves, be swift in response, reaction solution has been poured in frozen water mixed solution, had yellow-green colour solid to produce, filter, washing, dry, it is for subsequent use that recrystallization obtains product;
Second step: 2,4,6-trinitro--1,3-bis-(2 ', 4 '-dinitrobenzene vinyl) benzene synthetic
The first step is obtained 2,4,6-trinitro--1,3-bis-(2 '-nitrostyrolene base) benzene is dissolved in the vitriol oil, slowly drips nitrosonitric acid, stirring reaction under room temperature under low temperature, after reaction finishes, reaction solution is poured in frozen water mixed solution, separate out solid, dry, recrystallization obtains target product.
3. preparation method according to claim 2, is characterized in that: in the first step, preparing concentrated nitric acid mass concentration in aceticanhydride-concentrated nitric acid mixed solution is 65～68%.
4. preparation method according to claim 2, is characterized in that: concentrated nitric acid and 2,4 in aceticanhydride-concentrated nitric acid mixed solution in the first step, 6-trinitro--1, the mol ratio of 3-bis-(styryl) benzene is 5:1, and the reaction times is 5～10min, 10～45 DEG C of temperature.
5. preparation method according to claim 2, is characterized in that: in second step 2,4, and 6-trinitro--1, the mol ratio of 3-bis-(2 '-nitrostyrolene base) benzene and nitrosonitric acid is 1:4, the reaction times is 1～3h.
6. a compound 2,4,6-trinitro--1, the application of 3-bis-(2 ', 4 '-dinitrobenzene vinyl) benzene, is characterized in that this compound is for the synthesis of heat-resisting energetic material.
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| CN108191816A (en) * | 2018-02-08 | 2018-06-22 | 信阳师范学院 | Oxygen-containing heat-resisting energy-containing compound of bridging calixarene kind and preparation method thereof |
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| JPS5687046A (en) * | 1979-12-18 | 1981-07-15 | Asahi Glass Co Ltd | Sensitizer for organic photosensitive material |
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| JPS5687046A (en) * | 1979-12-18 | 1981-07-15 | Asahi Glass Co Ltd | Sensitizer for organic photosensitive material |
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| CN108191816A (en) * | 2018-02-08 | 2018-06-22 | 信阳师范学院 | Oxygen-containing heat-resisting energy-containing compound of bridging calixarene kind and preparation method thereof |
| CN108191816B (en) * | 2018-02-08 | 2021-04-20 | 信阳师范学院 | Heat-resistant energetic compound containing oxygen-bridged calixarene and preparation method thereof |
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