CN105439897A - Synthetic method of 2, 6-dinitro-p-diazido-methylbenzene - Google Patents
Synthetic method of 2, 6-dinitro-p-diazido-methylbenzene Download PDFInfo
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- CN105439897A CN105439897A CN201510795572.8A CN201510795572A CN105439897A CN 105439897 A CN105439897 A CN 105439897A CN 201510795572 A CN201510795572 A CN 201510795572A CN 105439897 A CN105439897 A CN 105439897A
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- dinitrobenzene
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C247/00—Compounds containing azido groups
- C07C247/16—Compounds containing azido groups with azido groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
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Abstract
The invention belongs to the field of the organic chemical synthesis, and relates to a synthetic method of dual-energetic-group energetic compound, in particular to a synthetic method of 2, 6-dinitro-p-diazido-methylbenzene. The synthetic method comprises the following steps: allowing 2, 6-dinitro-1, 4-diphenmethyol containing an energetic group aromatic alcohol used as a reaction raw material to react with phosphorus tribromide to obtain 2, 6-dinitro-p-dibromo methylbenzene; and facilitating the reaction between the 2, 6-dinitro-p-dibromo methylbenzene and sodium azide, and introducing the energetic group azido into a molecular structure to obtain the dual-energetic-group 2, 6-dinitro-p-diazido-methylbenzene containing azido and nitro. The synthetic method solves the problem that the existing plasticizer containing double energetic groups, namely, azido and nitro, are fewer in types; and meanwhile, and by virtue of the verification of an embodiment 1, the synthesized 2, 6-dinitro-p-diazido-methylbenzene has 1423 J/g of energy, the melting point is 71.2 DEG C, and the melting-point temperature falls within an ideal temperature range of melting and casting explosive liquid-phase carriers.
Description
Technical field
The invention belongs to organic chemical synthesis field, relate to a kind of two synthetic method containing energy base energy-containing compound, be specially the synthetic method of 2,6-dinitrobenzene to two azido-methyl benzene.
Background technology
Energetic material is general containing nitro (-NO in molecular structure
2), azido-(-N
3) or itrate group (-ONO
2) compound.The domestic and international study on the synthesis for energetic material is more at present, mainly concentrates on and introduces containing energy group in different molecular structures, as itrate group (-ONO
2), nitro (-NO
2), nitramino (-NNO
2) and azido-(-N
3) etc.
Nitro (-NO
2) be containing can group as the one of the molecule of explosive.Polynitroaramatics is widely used energetic material, as 2,4,6-trinitrotoluene (TNT).Nitrine organic compound is the novel energetic material of a class.Tamanori containing azido group, softening agent, oxygenant and other additive play a part uniqueness in the energetic materials such as propelling charge, propelling agent and high explosive.The energy level of energetic material can not only be improved, other excellent properties can also be given.Since azido-in 1864 is found, people have made large quantifier elimination to azido-in structure, synthesis and application etc.The impact sensitivity of quite a few saturated triazo-compound is very low, and thermostability meets the service requirements of explosive wastewater formula; Meanwhile, azido-energy is high, every mole of positive Heat of Formation that can provide about 356kJ, and does not affect oxygen balance, can not affect the carbon-to-oxygen ratio of compound; Azido-is again good source nitrogen, and hydrocarbon owing to not containing, products of combustion relative molecular mass is less, for propelling charge and propelling agent, not only can increase energy but also can reduce flame temperature, therefore, highly beneficial to the gunpowder development of the smokeless low ablation of high energy.In addition, azido-processing is simple, and raw material is easy to get.The impact sensitivity of especially saturated nitrine organic compound is lower, heat-resistant quality and chemical stability good, thus there is good practical value.
Present stage, two softening agent containing energy group containing azido-and nitro mainly contain trishydroxymethylnitromethane three nitrine acetic ester (TMNTA), 1,, there is the problem that kind is less in the ester compounds such as 3-diazido-2-propyl group-N-nitro-N-trinitro-propyl carbamate (DANTC).
In recent years, along with containing can nitrine softening agent, the developing on an unprecedented scale of cakingagent, to adapt with it and the novel nitrine softening agent that mates also grows up in succession, the extreme enrichment family of energetic plasticiser.2,6-dinitrobenzene is the organic compound simultaneously containing nitro and azido-to two azido-methyl benzene because its have to containing can the similar structure of nitrine cakingagent, energetic plasticiser, so there is good compatibleness when forming energetic material system.
Summary of the invention
Object of the present invention, overcome the existing two problems less containing the softening agent kind of energy group containing azido-and nitro, and provide a kind of containing azido-and nitro two containing can 2,6-dinitrobenzenes of group to the synthetic method of two azido-methyl benzene, concrete technical scheme is:
2,6-dinitrobenzene, to the synthetic method of two azido-methyl benzene, comprises the following steps:
(1) join in methylene chloride by 2,6-dinitrobenzene to two benzylalcohols, stir and form mixture, 0-30 DEG C of constant temperature, obtains A;
(2) be added drop-wise to by phosphorus tribromide in the A of step (1) gained, stir, 2,6-dinitrobenzene is 1:0.67 ~ 1:2.7 to two benzylalcohols and phosphorus tribromide mol ratio; Dropwise rear maintenance 10-40 DEG C of constant temperature and continue reaction 1 ~ 6h, obtain 2,6-dinitrobenzene to xylylene bromide mixed liquid B;
(3) by 2 of step (2) gained, 6-dinitrobenzene is transferred in beaker to xylylene bromide mixed liquid B, add isopyknic deionized water, mixed solution is transferred to separatory in separating funnel, discard upper water solution, methylene dichloride in lower floor's mixture carries out washing 3 times with the deionized water with methylene dichloride equal volume mutually again, all discards upper water solution;
(4) by the methylene dichloride phase underpressure distillation of step (3) gained, utilize Rotary Evaporators to reduce pressure and remove methylene dichloride, obtain 2,6-dinitrobenzene to xylylene bromide;
(5) join in solvent acetonitrile by 2,6-dinitrobenzenes of step (4) gained to xylylene bromide and sodiumazide, 2,6-dinitrobenzene is 1:2 ~ 1:3 to xylylene bromide and sodiumazide mol ratio; 50-90 DEG C of back flow reaction 4-24h, obtains 2,6-dinitrobenzene to two azido-methyl benzene mixed solutions;
(6) 2,6-dinitrobenzenes of step (5) gained are filtered through quantitative paper two azido-methyl benzene mixed solutions, collect filtrate, discard solid on filter paper;
(7) step (6) is collected contain 2,6-dinitrobenzene to the filtered liquid underpressure distillation of two azido-methyl benzene, utilize Rotary Evaporators to reduce pressure at 35-45 DEG C and remove acetonitrile, obtain 2,6-dinitrobenzene to two azido-methyl benzene.
Described reaction process provides temperature of reaction and stirring by heat-collecting magnetic stirring device, in glass three-necked bottle, complete reaction.
2, the 6-dinitrobenzenes provided by various embodiments of the present invention, to the synthetic method of two azido-methyl benzene, can bring following beneficial effect:
2,6-dinitrobenzenes provided by the invention to the synthetic method of two azido-methyl benzene, by with containing containing can 2,6-dinitrobenzenes of group aromatic alcohol be that reaction raw materials and phosphorus tribromide are obtained by reacting 2,6-dinitrobenzene to xylylene bromide to two benzylalcohols; 2,6-dinitrobenzene, to xylylene bromide and reaction of sodium azide, in the molecular structure by introducing containing can group azido-, to obtain containing azido-and nitro two containing energy group 2,6-dinitrobenzenes two azido-methyl benzene.
The invention solves the existing two problems less containing the softening agent kind of energy group containing azido-and nitro; , verify through the embodiment of the present invention 1,2, the 6-dinitrobenzenes synthesized by the present invention have the energy of 1423J/g to diazido toluene meanwhile.Fusing point is 71.2 DEG C, and melting temperature is in the desirable temperature range of castexplosive liquid phase carrier.
Accompanying drawing explanation
In order to be illustrated more clearly in the technical scheme of the embodiment of the present invention, below the accompanying drawing used required in describing embodiment is briefly described, apparently, accompanying drawing in below describing is only one embodiment of the present of invention, for those of ordinary skills, under the prerequisite not paying creative work, other embodiment and accompanying drawing thereof can also be obtained according to these accompanying drawing illustrated embodiments.
Fig. 1 is that obtained 2, the 6-dinitrobenzenes of the embodiment of the present invention 1 are to the infrared spectra spectrogram of two azido-methyl benzene.
Fig. 2 is that 2, the 6-dinitrobenzenes that the embodiment of the present invention 1 obtains compose spectrograms to two azido-methyl benzene nucleus magnetic resonance spectrum hydrogen.
Fig. 3 is that 2, the 6-dinitrobenzenes that the embodiment of the present invention 1 obtains compose spectrograms to two azido-methyl benzene nucleus magnetic resonance spectrum carbon.
Embodiment
Carry out clear, complete description below with reference to accompanying drawing to the technical scheme of various embodiments of the present invention, obviously, described embodiment is only a part of embodiment of the present invention, instead of whole embodiments.Based on the embodiment in the present invention, other embodiments all that those of ordinary skill in the art obtain under the prerequisite not making creative work, all belong to the scope that the present invention protects.
Embodiment 1
In 2,6-dinitrobenzenes of 20 DEG C of constant temperature are to two benzylalcohols and dichloromethane solution, drip phosphorus tribromide, wherein 2,6-dinitrobenzenes are to the mol ratio 1:0.67 of two benzylalcohols and phosphorus tribromide.Within 2 hours, drip the phosphorus tribromide of metering, react 6h under 10 DEG C of constant temperature stir, obtain 2,6-dinitrobenzene to xylylene bromide mixed solution.
By 2,6-dinitrobenzene is transferred in beaker to xylylene bromide mixed solution, add isopyknic deionized water, mixed solution is transferred to separatory in separating funnel, discards upper water solution, the methylene dichloride in lower floor's mixture carries out washing 3 times with the isopyknic deionized water of methylene dichloride mutually again, all discard upper water solution, lower floor's organism underpressure distillation, obtains 2,6-dinitrobenzene to xylylene bromide.
Join in solvent acetonitrile by 2,6-dinitrobenzene to xylylene bromide and sodiumazide, 2,6-dinitrobenzene is 1:2 to xylylene bromide and sodiumazide mol ratio; 50 DEG C of back flow reaction 24h, obtain 2,6-dinitrobenzene to two azido-methyl benzene mixed solutions.
2,6-dinitrobenzene is filtered through quantitative paper two azido-methyl benzene mixed solutions, collects filtrate, discard solid on filter paper; Containing the filtered liquid underpressure distillation of 2,6-dinitrobenzene to two azido-methyl benzene, Rotary Evaporators will be utilized to reduce pressure at 35 DEG C and to remove acetonitrile, obtain 2,6-dinitrobenzene to two azido-methyl benzene.
Fig. 1 be the present embodiment 2,6-dinitrobenzene to two azido-methyl benzene infrared spectra spectrograms, wherein 3080.95cm
-1for hydroxyl stretching vibration peak, 2881.21cm
-1for methylene radical stretching vibration peak, 2107.25cm
-1for azido-(-N
3) stretching vibration peak, 1544.29cm
-1for nitro antisymmetric stretching vibration peak, 1348.36cm
-1for nitro symmetrical stretching vibration peak.Characterized by product infrared spectrum, illustrate that synthesizing the product obtained is that 2,6-dinitrobenzene is to two azido-methyl benzene.
Fig. 2 is that 2,6-dinitrobenzenes prepared by the present embodiment compose spectrograms to two azido-methyl benzene nucleus magnetic resonance spectrum hydrogen.
1hNMR(600M, CD
3cOCD
3) ppm:5.91 (H-7,7 ', CH
2-N
3); 6.10 (H-8,8 ', CH
2-N
3); 8.57 (H-3, H-5, Ar-H), solvent acetone peak: 2.06.
Fig. 3 is that 2,6-dinitrobenzenes prepared by the present embodiment compose spectrograms to two azido-methyl benzene nucleus magnetic resonance spectrum carbon.
13cNMR(150M, CD
3cOCD
3) ppm:65.36 (C-7, CH
2-N
3), 71.61 (C-8, CH
2-N
3), 121.96 (C-1, Ar-CH), 128.97 (C-3, C-5, Ar-CH), 138.62 (C-4, Ar-CH), 151.12 (C-2, C-6, Ar-CH), solvent peak CD
3cOCD
3, 29.02 (CD
3), 205.83 (C=O).
Show that the material synthesized is that 2,6-dinitrobenzene is to two azido-methyl benzene by infrared spectrum and nmr analysis.Recording the fusing point of 2,6-dinitrobenzene to two azido-methyl benzene by melting point apparatus is 71.2 DEG C, utilize heat analysis method to record 2,6-dinitrobenzene has 1423J/g energy to diazido toluene.
Embodiment 2
In 2,6-dinitrobenzenes of 20 DEG C of constant temperature are to two benzylalcohols and dichloromethane solution, drip phosphorus tribromide, wherein 2,6-dinitrobenzenes are to the mol ratio 1:1 of two benzylalcohols and phosphorus tribromide.Within 2 hours, drip the phosphorus tribromide of metering, react 5h under 15 DEG C of constant temperature stir, obtain 2,6-dinitrobenzene to xylylene bromide mixed solution.
By 2,6-dinitrobenzene is transferred in beaker to xylylene bromide mixed solution, add isopyknic deionized water, mixed solution is transferred to separatory in separating funnel, discards upper water solution, the methylene dichloride in lower floor's mixture carries out washing 3 times with the isopyknic deionized water of methylene dichloride mutually again, all discard upper water solution, lower floor's organism underpressure distillation, obtains 2,6-dinitrobenzene to xylylene bromide.
Join in solvent acetonitrile by 2,6-dinitrobenzene to xylylene bromide and sodiumazide, 2,6-dinitrobenzene is 1:2.2 to xylylene bromide and sodiumazide mol ratio; 60 DEG C of back flow reaction 18h, obtain 2,6-dinitrobenzene to two azido-methyl benzene mixed solutions.
2,6-dinitrobenzene is filtered through quantitative paper two azido-methyl benzene mixed solutions, collects filtrate, discard solid on filter paper; Containing the filtered liquid underpressure distillation of 2,6-dinitrobenzene to two azido-methyl benzene, Rotary Evaporators will be utilized to reduce pressure at 35 DEG C and to remove acetonitrile, obtain 2,6-dinitrobenzene to two azido-methyl benzene.
Embodiment 3
In 2,6-dinitrobenzenes of 10 DEG C of constant temperature are to two benzylalcohols and dichloromethane solution, drip phosphorus tribromide, wherein 2,6-dinitrobenzenes are to the mol ratio 1:1.35 of two benzylalcohols and phosphorus tribromide.Within 2 hours, drip the phosphorus tribromide of metering, react 4h under 20 DEG C of constant temperature stir, obtain 2,6-dinitrobenzene to xylylene bromide mixed solution.
By 2,6-dinitrobenzene is transferred in beaker to xylylene bromide mixed solution, add isopyknic deionized water, mixed solution is transferred to separatory in separating funnel, discards upper water solution, the methylene dichloride in lower floor's mixture carries out washing 3 times with the isopyknic deionized water of methylene dichloride mutually again, discard upper water solution, lower floor's organism underpressure distillation, obtains 2,6-dinitrobenzene to xylylene bromide.
Join in solvent acetonitrile by 2,6-dinitrobenzene to xylylene bromide and sodiumazide, 2,6-dinitrobenzene is 1:2.4 to xylylene bromide and sodiumazide mol ratio; 70 DEG C of back flow reaction 12h, obtain 2,6-dinitrobenzene to two azido-methyl benzene mixed solutions.
2,6-dinitrobenzene is filtered through quantitative paper two azido-methyl benzene mixed solutions, collects filtrate, discard solid on filter paper; Containing the filtered liquid underpressure distillation of 2,6-dinitrobenzene to two azido-methyl benzene, Rotary Evaporators will be utilized to reduce pressure at 40 DEG C and to remove acetonitrile, obtain 2,6-dinitrobenzene to two azido-methyl benzene.
Embodiment 4
In 2,6-dinitrobenzenes of 10 DEG C of constant temperature are to two benzylalcohols and dichloromethane solution, drip phosphorus tribromide, wherein 2,6-dinitrobenzenes are to the mol ratio 1:1.7 of two benzylalcohols and phosphorus tribromide.Within 2 hours, drip the phosphorus tribromide of metering, react 3h under 25 DEG C of constant temperature stir, obtain 2,6-dinitrobenzene to xylylene bromide mixed solution.
By 2,6-dinitrobenzene is transferred in beaker to xylylene bromide mixed solution, add isopyknic deionized water, mixed solution is transferred to separatory in separating funnel, discards upper water solution, the methylene dichloride in lower floor's mixture carries out washing 3 times with the isopyknic deionized water of methylene dichloride mutually again, all discard upper water solution, lower floor's organism underpressure distillation, obtains 2,6-dinitrobenzene to xylylene bromide.
Join in solvent acetonitrile by 2,6-dinitrobenzene to xylylene bromide and sodiumazide, 2,6-dinitrobenzene is 1:2.6 to xylylene bromide and sodiumazide mol ratio; 80 DEG C of back flow reaction 8h, obtain 2,6-dinitrobenzene to two azido-methyl benzene mixed solutions.
2,6-dinitrobenzene is filtered through quantitative paper two azido-methyl benzene mixed solutions, collects filtrate, discard solid on filter paper; Containing the filtered liquid underpressure distillation of 2,6-dinitrobenzene to two azido-methyl benzene, Rotary Evaporators will be utilized to reduce pressure at 40 DEG C and to remove acetonitrile, obtain 2,6-dinitrobenzene to two azido-methyl benzene.
Embodiment 5
In 2,6-dinitrobenzenes of 0 DEG C of constant temperature are to two benzylalcohols and dichloromethane solution, drip phosphorus tribromide, wherein 2,6-dinitrobenzenes are to the mol ratio 1:2.0 of two benzylalcohols and phosphorus tribromide.Within 2 hours, drip the phosphorus tribromide of metering, react 2h under 30 DEG C of constant temperature stir, obtain 2,6-dinitrobenzene to xylylene bromide mixed solution.
By 2,6-dinitrobenzene is transferred in beaker to xylylene bromide mixed solution, add isopyknic deionized water, mixed solution is transferred to separatory in separating funnel, discards upper water solution, the methylene dichloride in lower floor's mixture carries out washing 3 times with the isopyknic deionized water of methylene dichloride mutually again, all discard upper water solution, lower floor's organism underpressure distillation, obtains 2,6-dinitrobenzene to xylylene bromide.
Join in solvent acetonitrile by 2,6-dinitrobenzene to xylylene bromide and sodiumazide, 2,6-dinitrobenzene is 1:2.8 to xylylene bromide and sodiumazide mol ratio; 90 DEG C of back flow reaction 8h, obtain 2,6-dinitrobenzene to two azido-methyl benzene mixed solutions.
2,6-dinitrobenzene is filtered through quantitative paper two azido-methyl benzene mixed solutions, collects filtrate, discard solid on filter paper; Containing the filtered liquid underpressure distillation of 2,6-dinitrobenzene to two azido-methyl benzene, Rotary Evaporators will be utilized to reduce pressure at 45 DEG C and to remove acetonitrile, obtain 2,6-dinitrobenzene to two azido-methyl benzene.
Embodiment 6
In 2,6-dinitrobenzenes of 30 DEG C of constant temperature are to two benzylalcohols and dichloromethane solution, drip phosphorus tribromide, wherein 2,6-dinitrobenzenes are to the mol ratio 1:2.7 of two benzylalcohols and phosphorus tribromide.Within 2 hours, drip the phosphorus tribromide of metering, react 1h under 30 DEG C of constant temperature stir, obtain 2,6-dinitrobenzene to xylylene bromide mixed solution.
By 2,6-dinitrobenzene is transferred in beaker to xylylene bromide mixed solution, add isopyknic deionized water, mixed solution is transferred to separatory in separating funnel, discards upper water solution, the methylene dichloride in lower floor's mixture carries out washing 3 times with the deionized water with methylene dichloride 3 times of volumes mutually again, all discard upper water solution, lower floor's organism underpressure distillation, obtains 2,6-dinitrobenzene to xylylene bromide.
Join in solvent acetonitrile by 2,6-dinitrobenzene to xylylene bromide and sodiumazide, 2,6-dinitrobenzene is 1:3 to xylylene bromide and sodiumazide mol ratio; 90 DEG C of back flow reaction 4h, obtain 2,6-dinitrobenzene to two azido-methyl benzene mixed solutions.
2,6-dinitrobenzene is filtered through quantitative paper two azido-methyl benzene mixed solutions, collects filtrate, discard solid on filter paper; Containing the filtered liquid underpressure distillation of 2,6-dinitrobenzene to two azido-methyl benzene, Rotary Evaporators will be utilized to reduce pressure at 45 DEG C and to remove acetonitrile, obtain 2,6-dinitrobenzene to two azido-methyl benzene.
Reaction process described in each embodiment provides temperature of reaction and stirring by heat-collecting magnetic stirring device, in glass three-necked bottle, complete reaction.
Various embodiment provided by the invention can combine as required in any way mutually, the technical scheme obtained by this combination, also within the scope of the invention.
Obviously, those skilled in the art can carry out various change and modification to the present invention and not depart from the spirit and scope of the present invention.Like this, if belong within the scope of the claims in the present invention and equivalent technologies thereof to these amendments of the present invention and modification, then the present invention also comprises these change and modification.
Claims (1)
1.2,6-dinitrobenzene, to the synthetic method of two azido-methyl benzene, comprises the following steps:
(1) join in methylene chloride by 2,6-dinitrobenzene to two benzylalcohols, stir and form mixture, 0-30 DEG C of constant temperature, obtains A;
(2) be added drop-wise to by phosphorus tribromide in the A of step (1) gained, stir, 2,6-dinitrobenzene is 1:0.67 ~ 1:2.7 to two benzylalcohols and phosphorus tribromide mol ratio; Dropwise rear maintenance 10-40 DEG C of constant temperature and continue reaction 1 ~ 6h, obtain 2,6-dinitrobenzene to xylylene bromide mixed liquid B;
(3) by 2 of step (2) gained, 6-dinitrobenzene is transferred in beaker to xylylene bromide mixed liquid B, add isopyknic deionized water, mixed solution is transferred to separatory in separating funnel, discard upper water solution, methylene dichloride in lower floor's mixture carries out washing 3 times with the deionized water with methylene dichloride equal volume mutually again, all discards upper water solution;
(4) by the methylene dichloride phase underpressure distillation of step (3) gained, utilize Rotary Evaporators to reduce pressure and remove methylene dichloride, obtain 2,6-dinitrobenzene to xylylene bromide;
(5) join in solvent acetonitrile by 2,6-dinitrobenzenes of step (4) gained to xylylene bromide and sodiumazide, 2,6-dinitrobenzene is 1:2 ~ 1:3 to xylylene bromide and sodiumazide mol ratio; 50-90 DEG C of back flow reaction 4-24h, obtains 2,6-dinitrobenzene to two azido-methyl benzene mixed solutions;
(6) 2,6-dinitrobenzenes of step (5) gained are filtered through quantitative paper two azido-methyl benzene mixed solutions, collect filtrate, discard solid on filter paper;
(7) step (6) is collected contain 2,6-dinitrobenzene to the filtered liquid underpressure distillation of two azido-methyl benzene, utilize Rotary Evaporators to reduce pressure at 35-45 DEG C and remove acetonitrile, obtain 2,6-dinitrobenzene to two azido-methyl benzene.
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