CN109438248A - A kind of preparation method of the fluoro- 1,5- dinitrobenzene of castexplosive 2,3,4- tri- - Google Patents
A kind of preparation method of the fluoro- 1,5- dinitrobenzene of castexplosive 2,3,4- tri- Download PDFInfo
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- CN109438248A CN109438248A CN201811216215.1A CN201811216215A CN109438248A CN 109438248 A CN109438248 A CN 109438248A CN 201811216215 A CN201811216215 A CN 201811216215A CN 109438248 A CN109438248 A CN 109438248A
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- castexplosive
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
- C07C201/06—Preparation of nitro compounds
- C07C201/14—Preparation of nitro compounds by formation of nitro groups together with reactions not involving the formation of nitro groups
Abstract
The invention belongs to technical field of compound preparation, disclose a kind of preparation method of fluoro- 1, the 5- dinitrobenzene of castexplosive 2,3,4- tri-, comprising the following steps: under low temperature stirring, nitrate or nitric acid are added in the 95-98% concentrated sulfuric acid；Then 2,3,4- trifluoronitrobenzenes are added, continue to be stirred to react complete；Reaction mixture is poured into ice water, precipitating is precipitated, is filtered, washing is dried to obtain 2,3,4- tri- fluoro- 1,5- dinitrobenzenes.Prepared by the present invention 2,3,4- tri- fluoro- 1,5- dinitrobenzenes compare TNT, have better detonation property, and higher density, the raw materials used safety of this method, required equipment is simple, and simple and easy, yield is higher, purity is also higher, easy purification, easily recrystallization.
Description
Technical field
The invention belongs to technical field of compound preparation, and in particular to a kind of fluoro- 1, the 5- dinitro of castexplosive 2,3,4- tri-
The preparation method of base benzene.
Background technique
Castexplosive refers to the composite explosives that casting dress can be carried out with molten state, is that current application is widest a kind of military mixed
Explosive is closed, 90% or more of military composite explosives is accounted for about.They adapt to the powder charge of various shape coyote hole, and comprehensive performance is preferable,
It is chiefly used in mortar, grenade, shell, guided missile warhead and mine explosive charge, occupies an important position in military composite explosives.Its
Carrier can be nitrified by nitrating agents such as nitric-sulfuric acid, fuming nitric aicd and nitric-acetic acid anhydrides and be synthesized.Ideal castexplosive should have
Have following property: (1) fusing point is 70~120 DEG C；(2) low-steam pressure (lower poison gas soakage)；(3) in fusing point and chemistry point
Solution has enough separation of charge before starting；(4) it does not shrink and expands when cooling；(5) very close to each other between ammunition and shell case；
(6) high density and excellent explosion property；(7) it prematurely explodes；(8) green syt.But there is contradiction between these performances,
As the castexplosive carrier and its formula of good behaviour performance are easy to shrink and expand while cooling.
The 2 of early application, 4,6- trinitrophenols (TNP) although detonation property it is good compared with TNT, mechanical sensitivity ratio TNT
Height, heat sensitivity is also higher and acid very strong, corrodes metal, safety is low.Therefore, TNP is gradually replaced by TNT, market of fading out.It is existing
Stage castexplosive mainly uses TNT as liquid phase carrier explosive, and TNT has played for the castexplosive of base in 20th century huge
Effect, has obtained worldwide approval, has been widely used in commercial explosive and military explosive.However TNT not only production process
The waste of middle discharge is all harmful to workers ' health and environment, and there are permeability, contraction, cavity, embrittlements and swollen for TNT class explosive
Swollen phenomenon can all have an impact the sensitivity of ammunition, vulnerability and transport.With the development of modern weapons, TNT is no longer able to satisfy
The requirement of current Desensitive ammunition standard, both at home and abroad all in the high-energy insensitive energetic material for finding alternative TNT energetically.
Summary of the invention
The purpose of the present invention is to provide a kind of preparation method of fluoro- 1, the 5- dinitrobenzene of castexplosive 2,3,4- tri-,
2 obtained, 3,4- tri- fluoro- 1,5- dinitrobenzenes compare TNT, have better detonation property, higher density.
To achieve the above object, the invention adopts the following technical scheme:
A kind of preparation method of fluoro- 1, the 5- dinitrobenzene of castexplosive 2,3,4- tri-, comprising the following steps: under low temperature stirring,
Nitrate or nitric acid are added in the 95-98% concentrated sulfuric acid；Then 2,3,4- trifluoronitrobenzenes are added, continue to be stirred to react
Completely；Reaction mixture is poured into ice water, precipitating is precipitated, is filtered, washing is dried to obtain 2,3,4- tri- fluoro- 1,5- dinitros
Benzene.
It further, is potassium nitrate, sodium nitrate or ammonium nitrate in the nitrate.
Further, the concentration of the nitric acid is 65%-100%.
Further, NO in the nitrate3 -Molal quantity is 1.1 times of 2,3,4 trifluoro nitrobenzene molal quantity.
Compared to existing castexplosive, the beneficial effects of the present invention are:
1. fluoro- 1, the 5- dinitrobenzene superior performance of the obtained target compound 2,3,4- tri- of preparation method of the present invention, can be extensive
Apply to the special dimensions such as castexplosive；It compares common castexplosive, such as TNT (2,4,6-trinitrotoluene), has more preferable
Detonation property, higher density, heated that smaller volume change etc. can occur, furthermore the compound is not soluble in water, to environment
Close friend, potential industrialization value is higher, is of great significance to the research of New Melt-cast Explosive Formulation.
2. preparation method of the present invention, raw materials used safety, required equipment is simple, simple and easy, yield is higher, purity also compared with
Height, easy purification, easily recrystallization.
3. preparation method of the present invention is compared with TNT, it is easier to which industrialized production is easy to purify.
Specific embodiment
The following examples are intended to illustrate the invention, but is not used to limit the scope of protection of the present invention.Unless otherwise specified, real
Apply the conventional means that technological means used in example is well known to those skilled in the art.Test method in following embodiments, such as
It is conventional method without special instruction.
Thin-layer chromatography (Thin Layer Chromatography, TLC), also known as thin-layer chromatography, belong to solid-liquid adsorption color
Spectrum.The present invention judges whether reaction is complete using the surplus of TLC technology detection 2,3,4- trifluoronitrobenzene (ZXC-16) of reaction kettle
At, if surplus be 0, react completion.
In the embodiment of the present invention, 2,3,4- tri- fluoro- 1.5- dinitrobenzenes are denoted as ZXC-16, and structural formula is
Embodiment 1
A kind of preparation method of fluoro- 1, the 5- dinitrobenzene (ZXC-16) of castexplosive 2,3,4- tri-, comprising the following steps:
Under ice-water bath, weighs potassium nitrate 5.55g (55mmol, 1.1eq) and be slowly added in the cold 50ml concentrated sulfuric acid that (sulfuric acid is dense
Degree is completely dissolved 95%), after addition to continue stirring to potassium nitrate, then, then is slowly added into 2,3,4- trifluoronitrobenzene 8.85g
(50mmol, 1.0eq) after adding, continues to be stirred to react complete (TLC detection) at room temperature.
After complete reaction, reaction mixture is slowly poured into ice water, there are a large amount of Precipitations, filtered, washed, it is dry
Obtain faint yellow solid, yield 89.01%.
Its hydrogen nuclear magnetic resonance spectrogram is1H NMR(600MHz,CDCl3-d1)δppm:8.79m,1H)；13C NMR(125MHz,
CDCl3-d1)；δppm:150.68-148.91(d),143.10-141.33(d),133.24,118.07；19F NMR(564MHz,
CDCl3-d 1)；δppm:-124.20,146.21；ESI-HRMS:m/z anion calcd for C6HF3N2O4,[M]-:
221.0792,found:221.0743；Elemental analysis calcd (%) for C6HF3N2O4 (222.08): C
32.47；H 0.46；F 25.67；N,12.79；found:C 32.45,H 0.45,F 25.66,N 12.61,O 28.82.
Embodiment 2
A kind of preparation method of fluoro- 1, the 5- dinitrobenzene (ZXC-16) of castexplosive 2,3,4- tri-, comprising the following steps:
Under ice-water bath, weighs ammonium nitrate 4.4g (55mmol, 1.1eq) and be slowly added in the cold 50ml concentrated sulfuric acid that (sulfuric acid is dense
Degree is completely dissolved 95%), after addition to continue stirring to potassium nitrate, then, then is slowly added into 2,3,4- trifluoronitrobenzene 8.85g
(50mmol, 1.0eq) after adding, continues to be stirred to react complete (TLC detection) at room temperature.
After complete reaction, reaction mixture is slowly poured into ice water, there are a large amount of Precipitations, filtered, washed, it is dry
Obtain faint yellow solid, yield 86.67%.
Embodiment 3
A kind of preparation method of fluoro- 1, the 5- dinitrobenzene (ZXC-16) of castexplosive 2,3,4- tri-, comprising the following steps:
Under ice-water bath, weighs potassium nitrate 5.55g (55mmol, 1.1eq) and be slowly added in the cold 50ml concentrated sulfuric acid that (sulfuric acid is dense
Degree is completely dissolved 98%), after addition to continue stirring to potassium nitrate, then, then is slowly added into 2,3,4- trifluoronitrobenzene 8.85g
(50mmol, 1.0eq) after adding, continues to be stirred to react complete (TLC detection) at room temperature.
After complete reaction, reaction mixture is slowly poured into ice water, there are a large amount of Precipitations, filtered, washed, it is dry
Obtain faint yellow solid, yield 87.34%.
Embodiment 4
A kind of preparation method of fluoro- 1, the 5- dinitrobenzene (ZXC-16) of castexplosive 2,3,4- tri-, comprising the following steps:
Under ice-water bath magnetic agitation, the nitric acid (concentration 65%) of 25ml is slowly added to (sulphur in the cold 50ml concentrated sulfuric acid
Acid concentration is 97%), then, then to be slowly added into 2,3,4- trifluoronitrobenzene 8.85g (50mmol, 1.0eq), after adding, in room
Continue to be stirred to react complete (TLC detection) under temperature.
After complete reaction, reaction mixture is slowly poured into ice water, there are a large amount of Precipitations, filtered, washed, it is dry
Obtain faint yellow solid, yield 81.63%.
Embodiment 5
A kind of preparation method of fluoro- 1, the 5- dinitrobenzene (ZXC-16) of castexplosive 2,3,4- tri-, comprising the following steps:
Under ice-water bath magnetic agitation, the nitric acid of 25ml (concentration 80%) is slowly added to (sulphur in the cold 50ml concentrated sulfuric acid
Acid concentration is 98%), then, then to be slowly added into 2,3,4- trifluoronitrobenzene 8.85g (50mmol, 1.0eq), after adding, by body
System continues to be stirred to react complete (TLC detection) after being slowly warming up to 100 DEG C.
After complete reaction, reaction mixture is slowly poured into ice water, there are a large amount of Precipitations, filtered, washed, it is dry
Obtain faint yellow solid, yield 83.45%.
Embodiment 6
A kind of preparation method of fluoro- 1, the 5- dinitrobenzene (ZXC-16) of castexplosive 2,3,4- tri-, comprising the following steps:
Under ice-water bath magnetic agitation, 25ml fuming nitric aicd is slowly added to in the cold 50ml concentrated sulfuric acid (sulfuric acid concentration is
95%), then, then 2,3,4- trifluoronitrobenzene 8.85g (50mmol, 1.0eq) are slowly added into, after adding, system is slowly risen
Temperature is to continuing after 100 DEG C to be stirred to react complete (TLC detection).
After complete reaction, reaction mixture is slowly poured into ice water, there are a large amount of Precipitations, filtered, washed, it is dry
Obtain faint yellow solid, yield 89.32%.
Embodiment 7
A kind of preparation method of fluoro- 1, the 5- dinitrobenzene (ZXC-16) of castexplosive 2,3,4- tri-, comprising the following steps:
Under ice-water bath magnetic agitation, 25ml nitric acid (concentration 100%) is slowly added to (sulfuric acid in the cold 50ml concentrated sulfuric acid
Concentration is 98%), then, then to be slowly added into 2,3,4- trifluoronitrobenzene 8.85g (50mmol, 1.0eq), after adding, by system
Continue to be stirred to react complete (TLC detection) at room temperature.
After complete reaction, reaction mixture is slowly poured into ice water, there are a large amount of Precipitations, filtered, washed, it is dry
Obtain faint yellow solid, yield 88.35%.
Embodiment 8
A kind of preparation method of fluoro- 1, the 5- dinitrobenzene (ZXC-16) of castexplosive 2,3,4- tri-, comprising the following steps:
Under ice-water bath, weighs potassium nitrate 5.55g (55mmol, 1.1eq) and be slowly added in the cold 50ml concentrated sulfuric acid that (sulfuric acid is dense
Degree is completely dissolved 96%), after addition to continue stirring to potassium nitrate, then, then is slowly added into 2,3,4- trifluoronitrobenzene 8.85g
(50mmol, 1.0eq) after adding, system is slowly raised to continue to be stirred to react complete (TLC detection) after room temperature.
After complete reaction, reaction mixture is slowly poured into ice water, there are a large amount of Precipitations, filtered, washed, it is dry
Obtain faint yellow solid, yield 89.56%.
Embodiment 9
A kind of preparation method of fluoro- 1, the 5- dinitrobenzene (ZXC-16) of castexplosive 2,3,4- tri-, comprising the following steps:
Under ice-water bath, accurately weighs sodium nitrate 4.67g (55mmol, 1.1eq) and be slowly added to (sulphur in the cold 50ml concentrated sulfuric acid
Acid concentration is 95%), to continue stirring after addition and be completely dissolved to sodium nitrate, then, then be slowly added into 2,3,4- trifluoronitrobenzenes
8.85g (50mmol, 1.0eq) after adding, system is slowly raised to continue to be stirred to react complete (TLC detection) after room temperature.
After complete reaction, reaction mixture is slowly poured into ice water, there are a large amount of Precipitations, filtered, washed, it is dry
Obtain faint yellow solid, yield 89.13%.
Embodiment 10
A kind of preparation method of fluoro- 1, the 5- dinitrobenzene (ZXC-16) of castexplosive 2,3,4- tri-, comprising the following steps:
Under ice-water bath, weighs potassium nitrate 555g (5.5mol, 1.1eq) and be slowly added to (sulfuric acid concentration in the cold 5L concentrated sulfuric acid
It is completely dissolved 95%), after addition to continue stirring to potassium nitrate, then, then is slowly added into 2,3,4- trifluoronitrobenzene 885g
(5.0mol, 1.0eq) after adding, system is slowly raised to continue to be stirred to react complete (TLC detection) after room temperature.
After complete reaction, reaction mixture is slowly poured into ice water, there are a large amount of Precipitations, filtered, washed, it is dry
Obtain faint yellow solid, yield 91.03%.This example demonstrates that in the case where material quantity amplification, the receipts of this preparation method
Rate is also higher；Compared with TNT, this preparation method is easier to industrialized production, is easy to purify.
11 performance parameter of embodiment compares
Bibliography (Shreeve J, Yin P, Mitchell L, et al.Comparative Study of Various
Pyrazole-based Anions:A Promising Family of Ionic derivatives as Insensitive
Energetic Materials. [J] .Chemistry-An Asian Journal, 2017,12.) the method measurement is implemented
The enthalpy of formation of the 1 fluoro- 1,5- dinitro (ZXC-16) of resulting 2,3,4- tri- of example and 2,4,6- trinitrotoluene (TNT), generate heat,
It is fluoro- to survey 2,3,4- tri- using densimeter (3H-2000, purchased from scientific and technological (Beijing) Co., Ltd of Bei Shide instrument) for explosion velocity and detonation pressure
The density of 1,5- dinitro (ZXC-16) and 2,4,6-trinitrotoluene (TNT), see Table 1 for details.
The performance parameter of table 1 ZXC-16 and TNT
As the result is shown: the big 0.318g/cm of density ratio TNT of ZXC-163, the impact sensitivity ratio TNT of ZXC-16 increases 31J,
The explosion velocity of ZXC-16 is 1.16 times of TNT, and the detonation pressure of ZXC-16 is also 1.5 times of TNT.
The embodiment of the above, only presently preferred embodiments of the present invention, is only used to explain the present invention, not limit
The scope of the present invention processed to those of ordinary skill in the art certainly can be according to skill disclosed in this specification
Art content makes other embodiments easily by way of replacing or changing, therefore all made in the principle of the present invention
Changes and improvements etc., should be included in scope of the present invention patent.
Claims (4)
1. a kind of preparation method of fluoro- 1, the 5- dinitrobenzene of castexplosive 2,3,4- tri-, which comprises the following steps:
Under low temperature stirring, nitrate or nitric acid are added in the 95-98% concentrated sulfuric acid；Then 2,3,4- trifluoronitrobenzenes are added, after
It is continuous be stirred to react it is complete；Reaction mixture is poured into ice water, precipitating is precipitated, is filtered, washing is dried to obtain 2,3,4- tri-
Fluoro- 1,5- dinitrobenzene.
2. the preparation method of fluoro- 1, the 5- dinitrobenzene of castexplosive 2,3,4- tri- according to claim 1, feature exist
In, in the nitrate be potassium nitrate, sodium nitrate or ammonium nitrate.
3. the preparation method of fluoro- 1, the 5- dinitrobenzene of castexplosive 2,3,4- tri- according to claim 1, feature exist
In the concentration of the nitric acid is 65%-100%.
4. the preparation method of fluoro- 1, the 5- dinitrobenzene of castexplosive 2,3,4- tri- according to claim 1, feature exist
In NO in the nitrate3 -Molal quantity is 1.1 times of 2,3,4 trifluoro nitrobenzene molal quantity.
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Cited By (3)
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| CN110218164A (en) * | 2019-05-30 | 2019-09-10 | 信阳师范学院 | Bis- (the fluoro- 2,6- dinitrophenyl of 3,4,5- tri-) urea of energetic material 1,3- and its preparation method and application |
| CN110437131A (en) * | 2019-09-04 | 2019-11-12 | 山东省鄄城县方源轴承化工有限公司 | A kind of preparation method of N- methyl -4- nitrophthalimide |
| CN111269126A (en) * | 2020-03-12 | 2020-06-12 | 北京理工大学重庆创新中心 | Preparation method of fusion-cast carrier 1, 2-difluoro-4, 5-dinitrobenzene |
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110218164A (en) * | 2019-05-30 | 2019-09-10 | 信阳师范学院 | Bis- (the fluoro- 2,6- dinitrophenyl of 3,4,5- tri-) urea of energetic material 1,3- and its preparation method and application |
| CN110218164B (en) * | 2019-05-30 | 2021-10-01 | 信阳师范学院 | Energetic material 1, 3-bis (3,4, 5-trifluoro-2, 6-dinitrophenyl) urea and preparation method and application thereof |
| CN110437131A (en) * | 2019-09-04 | 2019-11-12 | 山东省鄄城县方源轴承化工有限公司 | A kind of preparation method of N- methyl -4- nitrophthalimide |
| CN111269126A (en) * | 2020-03-12 | 2020-06-12 | 北京理工大学重庆创新中心 | Preparation method of fusion-cast carrier 1, 2-difluoro-4, 5-dinitrobenzene |
| CN111269126B (en) * | 2020-03-12 | 2023-04-07 | 北京理工大学重庆创新中心 | Preparation method of fusion casting carrier 1,2-difluoro-4,5-dinitrobenzene |
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Application publication date: 20190308 |