CN108821983A - It is a kind of using phenyl ring as heat resistive compounds of parent and its preparation method and application - Google Patents
It is a kind of using phenyl ring as heat resistive compounds of parent and its preparation method and application Download PDFInfo
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- CN108821983A CN108821983A CN201810807332.9A CN201810807332A CN108821983A CN 108821983 A CN108821983 A CN 108821983A CN 201810807332 A CN201810807332 A CN 201810807332A CN 108821983 A CN108821983 A CN 108821983A
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- dinitrobenzene
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/44—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring
- C07C211/52—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring the carbon skeleton being further substituted by halogen atoms or by nitro or nitroso groups
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- C—CHEMISTRY; METALLURGY
- C06—EXPLOSIVES; MATCHES
- C06B—EXPLOSIVES OR THERMIC COMPOSITIONS; MANUFACTURE THEREOF; USE OF SINGLE SUBSTANCES AS EXPLOSIVES
- C06B25/00—Compositions containing a nitrated organic compound
- C06B25/04—Compositions containing a nitrated organic compound the nitrated compound being an aromatic
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/04—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups
- C07C209/06—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of halogen atoms
- C07C209/10—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of halogen atoms with formation of amino groups bound to carbon atoms of six-membered aromatic rings or from amines having nitrogen atoms bound to carbon atoms of six-membered aromatic rings
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Abstract
The invention belongs to technical field of compound preparation, disclose a kind of using phenyl ring as heat resistive compounds of parent and its preparation method and application.Heat resistive compounds are fluoro- 1,3- diamino -4, the 6- dinitrobenzene of 2-, and preparation method includes the following steps：Under room temperature magnetic agitation, by the alcoholic solution of ammonium hydroxide or ammonia and solid 2,3,4- tri- fluoro- 1,5- dinitrobenzene mixing, stirring is filtered, washed after completion of the reaction, is dried to obtain fluoro- 1,3- diamino -4, the 6- dinitrobenzene of heat resistive compounds 2- shown in Formulas I.Compared with TATB, the detonation property of fluoro- 1,3- diamino -4, the 6- dinitrobenzene of 2- is more excellent, and sensitivity is close with TATB, and synthetic method is very easy, and yield is higher, easy to industrialized production；The compound is not soluble in water, environmentally friendly, thus, potential industrialization value is higher, is of great significance to the research of heat resistance explosive.
Description
Technical field
The invention belongs to technical field of compound preparation, and in particular to it is a kind of using phenyl ring as the heat resistive compounds of parent and its
Preparation method and application.
Background technique
Precision strike, efficient Kill capability and failure-survival capability are the targets that modern weapons are pursued, and to realize these targets,
High Energy Density Materials (HEDM) as weapon energy carrier must satisfy high-energy, high density, Low vulnerability, environment and adapt to
The requirement of property and high thermal stability.In recent years, with the subterranean resource such as space travel cause and petroleum gas exploit development,
A kind of energy high pressure resistant (or low pressure), explosive resistant to high temperature of more more and more urgent needs, abbreviation heat-resistant explosive.Heat-resistant explosive, which refers to, to be subjected to
A kind of explosive of mechanical sensitivity appropriate and reliable initiation is still able to maintain after prolonged hot environment, this kind of explosive is removed with general
Outside the detonation property that logical explosive is possessed, it usually should also have higher fusing point and higher thermal decomposition temperature (more than 250 DEG C).
The research of heat-resistant explosive is that (universe for such as needing to be subjected to hot environment flies in order to meet the needs of military and aerospace etc. earliest
Row device, separation at different levels of airship etc.), now, the most important purposes of heat-resistant explosive is the explosive for perforating oil gas well bullet
In, it is divided into heat-resisting single chmical compound explosive and heat-resisting composite explosives.Meanwhile by the difference of institute's tolerable temperature, heat-resistant explosive is drawn
It is divided into high temperature resistant explosive (thermal decomposition temperature is in 250 DEG C or more and 300 DEG C of energy-containing compounds below) and superhigh temperature resistant degree explosive
(thermal decomposition temperature is more than 300 DEG C or more of energy-containing compound).Heat-resisting single chmical compound explosive can be used for loading heat-resisting detonator and resistance to thermal conductivity
In quick-fried rope, it is often more important that, it can be used as the basic components of heat-resisting composite explosives, and such as obtaining widely applied is in petroleum technology
Perforating bullet powder charge etc.；On the other hand, put forth effort to develop some new heat-resisting single chmical compound explosives to be to meet cosmonautic special type
It needs, because the development of rocket, guided missile and space shuttle in speed, the especially appearance of space weapon, propose explosive
The requirement of thermostability.Spaceship is in flight course due to will receive aerodynamic effects and space and moon vacuum
The influence of environment etc., thus space vehicle is both needed to heating before entering space and returning to the earth with sterilization, but routine is fried
Medicine (such as heisuojin) is not sufficiently stable under high temperature or low pressure for a long time, or even is easy to evaporate under aerodynamic effects, is not able to satisfy
Above-mentioned requirements.Thus, in recent years, some countries both focus on how research improves now developed explosive such as hexogen, Losec support
The thermostability of gold etc., and put forth effort to develop the heat-resistant explosive of some new superhigh temperature resistants to meet the special type of space travel etc.
It needs.
Summary of the invention
The purpose of the present invention is to provide a kind of using phenyl ring as the heat resistive compounds of parent --- the fluoro- 1,3- diamino-of 2-
4,6- dinitrobenzenes (ZXC-10), the heat resistive compounds thermal stability are very good.
Another object of the present invention is to provide the preparation method of above-mentioned heat resistive compounds, raw materials used safety is required to set
Standby simple, preparation method is simple, and yield is higher.
To achieve the above object, the present invention uses following technical scheme：
The present invention provides a kind of using phenyl ring as the heat resistive compounds of parent, and structural formula is shown in formula I：
The present invention provides the preparation method of above-mentioned heat resistive compounds again, includes the following steps：
Under room temperature magnetic agitation, by the alcoholic solution of ammonium hydroxide or ammonia and solid 2,3,4- tri- fluoro- 1,5- dinitrobenzene mixing are stirred
It mixes, is filtered, washed after completion of the reaction, is dried to obtain fluoro- 1,3- diamino -4, the 6- dinitro of heat resistive compounds 2- shown in Formulas I
Benzene.
Method one：Under magnetic stirring, that the alcoholic solution of certain density ammonium hydroxide or ammonia is added to solid 2,3,4- tri- is fluoro-
It in 1,5- dinitrobenzene, after fully reacting, filters, washing, obtains fluoro- 1,3- diamino -4, the 6- dinitrobenzene of product 2-, reaction temperature
Degree is 0~100 DEG C；
Method two：Under magnetic stirring, fluoro- 1, the 5- dinitrobenzene of solid 2,3,4- tri- is added to certain density ammonium hydroxide or ammonia
Alcoholic solution in, after fully reacting, filter, washing, obtain fluoro- 1,3- diamino -4, the 6- dinitrobenzene of product 2-, reaction temperature is
0~100 DEG C.
Further, the molar ratio of the ammonia and 2 in the alcoholic solution of ammonium hydroxide or ammonia, 3,4- tri- fluoro- 1,5- dinitrobenzenes is greater than
Equal to 4.
Further, the concentration of ammonia is 10~100% in the alcoholic solution of the ammonium hydroxide or ammonia.
Further, the concentration of ammonia is 40% in the ammonium hydroxide.
The present invention also provides the heat resistive compounds to prepare the application in heat-resistant explosive.
Compared to the heat-resistant explosive of existing superior performance, the beneficial effects of the present invention are：
1. obtained fluoro- 1,3- diamino -4, the 6- dinitrobenzene performance (being shown in Table 1) of target compound 2- of the present invention is superior, can
It is widely used in the special dimensions such as deep oil well or space exploration；It compares common heat-resistant explosive, such as TATB (1,3,5- tri- amido-
2,4,6-trinitrotoluene), there is better detonation property, not soluble in water, environmentally friendly, potential industrialization value is more
Height is of great significance to the research of heat resistance explosive.
2. raw materials used in the preparation method of the fluoro- 1,3- diamino -4,6- dinitrobenzene of target compound 2- of the invention
Safety, required equipment is simple, and preparation method is simple and easy more than TATB, and yield is higher, purity is also higher, easy purification, Yi Chongjie
It is brilliant.
3. the compounds of this invention is compared with TATB, it is easier to industrialized production.
Detailed description of the invention
Fig. 1 is the crystal shape of the fluoro- 1,3- diamino -4,6- dinitrobenzene of heat resistive compounds 2- of the present invention.
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 fluoro- 1, the 5- dinitrobenzene of reaction kettle 2,3,4- tri-
At, if surplus be 0, react completion.
In the present invention, fluoro- 1,3- diamino -4, the 6- dinitrobenzene of 2- is denoted as ZXC-10；Tri- amido -2,4,6- three of 1,3,5-
Nitrotoleune is denoted as TATB.
Embodiment 1
It is a kind of using phenyl ring as the preparation of fluoro- 1,3- diamino -4, the 6- dinitrobenzene of the heat resistive compounds 2- of parent, including following step
Suddenly：
2,3,4- tri- 5.0 grams of fluoro- 1,5- dinitrobenzenes are accurately weighed, are put into one 100 milliliters of eggplant-shape bottle, room temperature magnetic force
It is added with stirring 50 milliliters of 40% concentrated ammonia liquor, after adding, continues to be stirred to react completely that (TLC detection, time is about at room temperature
21 hours), it filters, washing obtains bright yellow solid (fluoro- 1,3- diamino -4, the 6- dinitrobenzene of 2-), yield 93.01%；
Its hydrogen nuclear magnetic resonance spectrogram is1H NMR(600MHz,DMSO-d6, TMS, ppm), δ=8.63 (s, 1H), 7.55 (s, 4H)；13C
NMR(125MHz,DMSO-d6, TMS, ppm), δ=138.30,136.10,123.23,122.39；Elemental Analysis
for C6H5FN4O4(216.13):calcd.C,33.75；H,2.16；F:8.65；N,25.89；found:C,33.34；H,
2.33；F:8.79；N,25.92；O,29.61.
Embodiment 2
It is a kind of using phenyl ring as the preparation of fluoro- 1,3- diamino -4, the 6- dinitrobenzene of the heat resistive compounds 2- of parent, including following step
Suddenly：
2,3,4- tri- 5.0 grams of fluoro- 1,5- dinitrobenzenes are accurately weighed, are put into one 100 milliliters of eggplant-shape bottle, room temperature magnetic force
It is added with stirring 10 milliliters of 40% concentrated ammonia liquor, after adding, continues to be stirred to react completely that (TLC detection, time is about at room temperature
47 hours), it filters, washing obtains bright yellow solid (fluoro- 1,3- diamino -4, the 6- dinitrobenzene of 2-), yield 90.65%.
Embodiment 3
It is a kind of using phenyl ring as the preparation of fluoro- 1,3- diamino -4, the 6- dinitrobenzene of the heat resistive compounds 2- of parent, including following step
Suddenly：
It accurately weighs 2,3,4- tri- 5.0 grams of fluoro- 1,5- dinitrobenzenes, under room temperature magnetic agitation, is added to one equipped with 50 milliliters
In 100 milliliters of eggplant-shape bottles of 40% concentrated ammonia liquor, after adding, continue to be stirred to react completely that (TLC detection, the time is about at room temperature
It is 21 hours), it filters, washing obtains bright yellow solid (fluoro- 1,3- diamino -4, the 6- dinitrobenzene of 2-), yield is
92.76%.
Embodiment 4
It is a kind of using phenyl ring as the preparation of fluoro- 1,3- diamino -4, the 6- dinitrobenzene of the heat resistive compounds 2- of parent, including following step
Suddenly：
2,3,4- tri- 5.0 grams of fluoro- 1,5- dinitrobenzenes are accurately weighed, are put into one 100 milliliters of eggplant-shape bottle, room temperature magnetic force
20 milliliters of ethylene glycol are added with stirring, ammonia is passed through, until having reacted (TLC detection, the time is about 11 hours), is filtered, washing,
It obtains bright yellow solid (fluoro- 1,3- diamino -4, the 6- dinitrobenzene of 2-), yield 84.23%.
Embodiment 5
It is a kind of using phenyl ring as the preparation of fluoro- 1,3- diamino -4, the 6- dinitrobenzene of the heat resistive compounds 2- of parent, including following step
Suddenly：
It accurately weighs 2,3,4- tri- 100.0 grams of fluoro- 1,5- dinitrobenzenes, under room temperature magnetic agitation, is added to one equipped with 300 millis
In 500 milliliters of eggplant-shape bottles for rising 40% concentrated ammonia liquor, after adding, continue to be stirred to react (TLC detection, time completely at room temperature
About 21 hours), it filters, washing obtains bright yellow solid (fluoro- 1,3- diamino -4, the 6- dinitrobenzene of 2-), yield is
93.76%.
6 performance parameter of embodiment compares
Bibliography (Yin P, Parrish D A, Shreeve J M.Energetic Multifunctionalized
Nitraminopyrazoles and Their Ionic Derivatives:Ternary Hydrogen-Bond Induced
High Energy Density Materials[J].Journal of the American Chemical Society,
2015,137(14):4778.) the method measures the fluoro- 1,3- diamino -4,6- dinitrobenzene (ZXC- of the resulting 2- of embodiment 1
10) and 1,3,5- tri- amidos -2,4,6-trinitrotoluene (TATB) enthalpy of formation, generation heat, explosion velocity, detonation pressure use densimeter
(3H-2000 Bei Shide company) surveys the fluoro- 1,3- diamino -4,6- dinitrobenzene (ZXC-10) of 2- and tri- amido -2,4 1,3,5-,
The density of 6- trinitrotoluene (TATB), as a result see Table 1 for details.
The performance parameter of table 1ZXC-10 and TATB
As the result is shown：The enthalpy of formation ratio TATB of big 0.09, the ZXC-10 of density ratio TATB of ZXC-10 increases 17.64%,
The explosion velocity ratio TATB that the generation heat ratio TATB of ZXC-10 increases 14.12%, ZXC-10 increases the detonation pressure of 2.41%, ZXC-10
8.00% is increased than TATB.
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 (6)
1. a kind of using phenyl ring as the heat resistive compounds of parent, which is characterized in that its structural formula is shown in formula I：
。
2. the preparation method of heat resistive compounds described in claim 1, which is characterized in that under room temperature magnetic agitation, by ammonium hydroxide
Or the alcoholic solution of ammonia and fluoro- 1, the 5- dinitrobenzene of solid 2,3,4- tri- mix, stirring is filtered, washed after completion of the reaction, dries
To the fluoro- 1,3- diamino -4,6- dinitrobenzene of heat resistive compounds 2- shown in Formulas I.
3. the preparation method of heat resistive compounds according to claim 2, which is characterized in that in the alcoholic solution of ammonium hydroxide or ammonia
The molar ratio of ammonia and the fluoro- 1,5- dinitrobenzene of 2,3,4- tri- is more than or equal to 4.
4. the preparation method of heat resistive compounds according to claim 2, which is characterized in that the alcoholic solution of the ammonium hydroxide or ammonia
The concentration of middle ammonia is 10~100%.
5. the preparation method of heat resistive compounds according to claim 2, which is characterized in that the concentration of ammonia in the ammonium hydroxide
It is 40%.
6. heat resistive compounds described in claim 1 are preparing the application in heat-resistant explosive.
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Cited By (2)
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| CN109810006A (en) * | 2019-02-21 | 2019-05-28 | 信阳师范学院 | Fluoro- 2,6- dinitroaniline of a kind of castexplosive 3,4,5- tri- and its preparation method and application |
| CN112266181A (en) * | 2020-11-17 | 2021-01-26 | 衡阳凌云特种材料有限公司 | Heat-proof/insulation composite material and preparation method and application thereof |
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