CN115160142A - Method for extracting high-purity trinitrotoluene from retired ammunition - Google Patents
Method for extracting high-purity trinitrotoluene from retired ammunition Download PDFInfo
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- CN115160142A CN115160142A CN202210845147.5A CN202210845147A CN115160142A CN 115160142 A CN115160142 A CN 115160142A CN 202210845147 A CN202210845147 A CN 202210845147A CN 115160142 A CN115160142 A CN 115160142A
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- SPSSULHKWOKEEL-UHFFFAOYSA-N 2,4,6-trinitrotoluene Chemical compound CC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O SPSSULHKWOKEEL-UHFFFAOYSA-N 0.000 title claims abstract description 118
- 239000000015 trinitrotoluene Substances 0.000 title claims abstract description 117
- 238000000034 method Methods 0.000 title claims abstract description 77
- 239000000706 filtrate Substances 0.000 claims abstract description 153
- 239000013078 crystal Substances 0.000 claims abstract description 99
- 238000001914 filtration Methods 0.000 claims abstract description 95
- 239000000047 product Substances 0.000 claims abstract description 84
- 238000001816 cooling Methods 0.000 claims abstract description 75
- 239000012467 final product Substances 0.000 claims abstract description 71
- 239000002904 solvent Substances 0.000 claims abstract description 67
- 238000010438 heat treatment Methods 0.000 claims abstract description 34
- 238000001035 drying Methods 0.000 claims abstract description 33
- 238000002425 crystallisation Methods 0.000 claims abstract description 16
- 230000008025 crystallization Effects 0.000 claims abstract description 16
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 45
- 239000000203 mixture Substances 0.000 claims description 41
- 230000008569 process Effects 0.000 claims description 31
- 239000002360 explosive Substances 0.000 claims description 29
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 23
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 15
- 239000000126 substance Substances 0.000 claims description 12
- 238000003756 stirring Methods 0.000 claims description 11
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 10
- 238000004090 dissolution Methods 0.000 claims description 10
- 238000003303 reheating Methods 0.000 claims description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 8
- UPSVYNDQEVZTMB-UHFFFAOYSA-N 2-methyl-1,3,5-trinitrobenzene;1,3,5,7-tetranitro-1,3,5,7-tetrazocane Chemical compound CC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O.[O-][N+](=O)N1CN([N+]([O-])=O)CN([N+]([O-])=O)CN([N+]([O-])=O)C1 UPSVYNDQEVZTMB-UHFFFAOYSA-N 0.000 claims description 6
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 4
- 238000003860 storage Methods 0.000 claims description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 4
- 238000002156 mixing Methods 0.000 claims description 2
- 239000000463 material Substances 0.000 abstract description 8
- 238000006243 chemical reaction Methods 0.000 abstract description 5
- 238000003889 chemical engineering Methods 0.000 abstract description 2
- 231100000053 low toxicity Toxicity 0.000 abstract description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 39
- 239000001257 hydrogen Substances 0.000 description 39
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 25
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 18
- -1 methyl hydrogen Chemical compound 0.000 description 15
- 238000004128 high performance liquid chromatography Methods 0.000 description 14
- 238000005481 NMR spectroscopy Methods 0.000 description 9
- 238000001514 detection method Methods 0.000 description 9
- 230000009467 reduction Effects 0.000 description 9
- 238000004611 spectroscopical analysis Methods 0.000 description 8
- 238000005160 1H NMR spectroscopy Methods 0.000 description 7
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 7
- 229910052799 carbon Inorganic materials 0.000 description 5
- 238000001228 spectrum Methods 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 4
- 230000008901 benefit Effects 0.000 description 3
- 230000001376 precipitating effect Effects 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000000638 solvent extraction Methods 0.000 description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 230000001737 promoting effect Effects 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 238000005422 blasting Methods 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- 239000003586 protic polar solvent Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
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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
- C07C201/16—Separation; Purification; Stabilisation; Use of additives
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The application relates to the field of chemical engineering and new materials, and provides a method for extracting high-purity trinitrotoluene from retired ammunition, based on the accurate control of the solubility of trinitrotoluene in different solvents, selecting a proper solvent and the using amount of the solvent to dissolve retired ammunition, filtering to obtain filtrate, repeatedly heating and cooling the filtrate for a first preset number of times, filtering to obtain final filtrate, wherein the final filtrate is used for crystallization; and cooling and crystallizing the final filtrate, filtering to obtain a crystal product, and drying the crystal product to obtain a final product, wherein the final product is trinitrotoluene crystal, and the purity of the final product is more than 99%. The method can efficiently, safely, low-toxicity and low-cost extract the trinitrotoluene from the retired ammunition, and the trinitrotoluene extracted from the retired ammunition has high purity, so that a foundation is laid for the conversion of the trinitrotoluene into a high value-added product.
Description
Technical Field
The embodiment of the application relates to the field of chemical engineering and new materials, in particular to a method for extracting high-purity trinitrotoluene from retired ammunition.
Background
2,4, 6-trinitrotoluene (TNT, trinitrotoluene) is the most widely applied energy-containing compound in the global scope and plays an important role in the fields of military weaponry, civil blasting equipment and the like. However, with the sharp decrease of the demand of TNT in the peaceful period of recent decades and the emergence and practical application of energy-containing compounds with more excellent performance, such as RDX, HMX and the like, the application field and the demand of trinitrotoluene are continuously reduced. Particularly in the military field, a large number of trinitrotolyl-based ammunition continue to face retirement scrap. The difficulty of the ammunition treatment is caused by how to extract and separate the trinitrotoluene component in the waste and old retired ammunition.
At present, the method for separating trinitrotoluene from old retired ammunition mainly comprises a melting separation method and a solvent extraction method. However, the application scenes of the two methods are concentrated in the field of energetic materials, no specific requirement is made on the purity of trinitrotoluene, and the problems of low material utilization rate and high potential safety hazard risk exist.
Disclosure of Invention
The embodiment of the application aims to provide a method for extracting high-purity trinitrotoluene from retired ammunition, aims to solve the problems in the prior art, and can efficiently, safely, low-toxicity and low-cost extract high-purity trinitrotoluene from retired ammunition.
The embodiment of the application provides a method for extracting high-purity trinitrotoluene from retired ammunition, which comprises the following steps:
dissolving retired ammunition in a solvent, and filtering to obtain a filtrate, wherein the solvent is determined based on the solubility of trinitrotoluene in the solvent;
heating and cooling the filtrate for a first preset number of times, and filtering to obtain final filtrate, wherein the final filtrate is used for crystallization;
and cooling and crystallizing the final filtrate, filtering to obtain a crystal product, and drying the crystal product to obtain a final product, wherein the final product is trinitrotoluene crystal, and the purity of the final product is more than 99%.
Optionally, the method comprises the steps of dissolving retired ammunition in a solvent, and filtering to obtain a filtrate, and specifically comprises the following steps:
mixing the retired ammunition with the solvent according to a preset proportion to obtain a mixture to be filtered;
heating the mixture to be filtered to a first dissolving temperature, and stirring and preserving heat within a first preset time;
and filtering the mixture to be filtered while the mixture is hot, and removing insoluble substances in the mixture to be filtered to obtain the filtrate.
Optionally, heating, cooling, and filtering the filtrate for a first preset number of times to obtain a final filtrate, specifically including the following steps:
naturally cooling the filtrate to a preset cooling temperature, and then reheating to a second dissolving temperature;
immediately stopping heating, and filtering the filtrate;
and repeating the processes of naturally cooling, reheating and filtering the filtrate for the first preset times, and combining the filtrates obtained by each filtration to obtain the final filtrate.
Optionally, cooling and crystallizing the final filtrate, filtering to obtain a crystal product, and drying the crystal product to obtain a final product, specifically including the following steps:
heating the final filtrate to a third dissolution temperature;
rapidly cooling the final filtrate at the third dissolving temperature to a rapid cooling temperature, crystallizing within a preset crystallization time, and filtering through a positive pressure filter to obtain the crystal product separated out from the final filtrate, wherein the crystal product is trinitrotoluene crystal;
and putting the crystal product into a vacuum oven, and drying at a drying temperature and under a vacuum pressure to obtain the final product.
Optionally, after dissolving retired ammunition in a solvent and filtering to obtain a filtrate, the method further comprises:
naturally cooling the filtrate to a target natural cooling temperature, standing for a second preset time, and filtering to obtain the crystal product;
repeating the processes of dissolving, filtering, natural cooling crystallization and filtering the crystal product for a second preset number of times;
and drying the crystal product to obtain the final product.
Optionally, the method comprises at least one of the following features:
(1) The solvent is one of toluene, acetone, ethyl acetate, chloroform, tetrahydrofuran and dioxane;
(2) The decommissioned ammunition comprises one or more of storage decommissioned trinitrotoluene explosive, B explosive, TNT-Al, HBX-3 and Octol explosive;
(3) The first dissolving temperature is 50-100 ℃;
(4) The first preset time is 0.5-5h;
(5) The preset ratio is (1.
Optionally, the method comprises at least one of the following features:
(1) The second dissolving temperature is 50-100 ℃;
(2) The preset cooling temperature is 0-40 ℃;
(3) The first preset times are 5-10 times.
Optionally, the method comprises at least one of the following features:
(1) The third dissolving temperature is 50-100 ℃;
(2) The rapid cooling temperature is-5 to 5 ℃;
(3) The preset crystallization time is 1-10h;
(3) The drying temperature is 30 ℃;
(4) The vacuum pressure is 0.1-0.5MPa.
Optionally, the method comprises at least one of the following features:
(1) The target natural cooling temperature is 0-30 ℃;
(2) The second preset time is 0.5-5h;
(3) The second preset times is 3-5 times.
Has the advantages that:
the application provides a method for extracting high-purity trinitrotoluene from decommissioned ammunition, through utilizing the specific solvent of preset proportion under the preset temperature, selectively dissolve trinitrotoluene in decommissioned ammunition, remove the insoluble substance to utilize the solubility of trinitrotoluene in the filtrate of specific solvent to be along with the difference of temperature variation, high-purity trinitrotoluene crystal is selectively crystallized out, has following advantage:
(1) By selecting specific solvent, temperature and proportion, the trinitrotoluene extracted from retired ammunition has high purity, and the solvent can be reused, so that the production cost and the pollution to the environment are reduced.
(2) The method selects a recrystallization process to separate and purify trinitrotoluene in decommissioned ammunition, has simple process, and is favorable for promoting the decommissioning conversion application process of energetic materials.
(3) The method is a wet process, all steps and reaction conditions in the process are safe and controllable, the safety risk in the production flow is small, the types of applicable retired ammunition are numerous, and the application range is wide.
Drawings
In order to more clearly illustrate the technical solutions of the embodiments of the present application, the drawings needed to be used in the description of the embodiments of the present application will be briefly introduced below, and it is obvious that the drawings in the following description are only some embodiments of the present application, and it is obvious for those skilled in the art that other drawings can be obtained according to these drawings without inventive exercise.
FIG. 1 is a flow diagram of a process for extracting high purity trinitrotoluene from decommissioned ammunition as set forth in one embodiment of the present application;
FIG. 2 is a flow chart of the process for extracting trinitrotoluene by directly cooling and crystallizing the filtrate in the air according to an embodiment of the present application;
FIG. 3 is a NMR spectrum of the final product of example one of the present application;
FIG. 4 is an IR spectrum of the final product of example one of the present application;
FIG. 5 shows the final product of the first embodiment of the present application 13 C-APT nuclear magnetic resonance spectrogram;
FIG. 6 is a HPLC detection chart of the final product in example one of the present application;
FIG. 7 is a NMR spectrum of the final product of example II of the present application;
FIG. 8 is a HPLC detection of the final product of example two of the present application;
FIG. 9 is a NMR spectrum of the final product in example III of the present application;
FIG. 10 is a HPLC check of the final product in example III of the present application.
Detailed Description
The following examples are provided to better understand the present invention, not to limit the best mode, and not to limit the content and protection scope of the present invention, and any product that is the same or similar to the present invention and is obtained by combining the present invention with other features of the prior art and the present invention falls within the protection scope of the present invention.
The specific experimental procedures or conditions are not indicated in the examples and can be performed according to the procedures or conditions of the conventional experimental procedures described in the prior art in this field. The reagents and other instruments used are conventional reagent products which are commercially available, and manufacturers are not indicated.
In the related technology, the method for separating trinitrotoluene from old retired ammunition mainly comprises a melting separation method and a solvent extraction method. The melting separation method is to heat the explosive to be in a melting state and then separate the explosive by utilizing the difference of physical properties of all components, and the solvent extraction method mainly utilizes the solubility difference of different components in the waste and old retired ammunition in a solvent to separate the explosive. However, the application scenes of the two methods are concentrated in the field of energetic materials, no specific requirement is made on the purity of trinitrotoluene, and the problems of low material utilization rate and high potential safety hazard risk exist.
In view of the above, the embodiment of the present application provides a method for extracting high-purity trinitrotoluene from retired ammunition, in which trinitrotoluene in retired ammunition is selectively dissolved by using a predetermined proportion of a specific solvent at a predetermined temperature, insoluble substances are removed, and high-purity trinitrotoluene crystals are selectively crystallized and precipitated by using the difference of solubility of trinitrotoluene in a filtrate of the specific solvent as a function of temperature, and fig. 1 shows a flow chart of a method for extracting high-purity trinitrotoluene from retired ammunition, as shown in fig. 1, the method comprises the following specific steps:
s101, dissolving retired ammunition in a solvent, and filtering to obtain a filtrate.
In specific implementation, the decommissioned ammunition is mixed with a solvent according to a preset proportion to obtain a mixture to be filtered; then heating the mixture to be filtered to a first dissolving temperature, and stirring and preserving heat within a preset time; and filtering the mixture to be filtered while the mixture is hot, and removing insoluble substances in the mixture to be filtered to obtain the filtrate.
In some embodiments, the solvent is one of toluene, acetone, ethyl acetate, chloroform, tetrahydrofuran, dioxane;
in some embodiments, the decommissioned ammunition comprises one or more of storage decommissioned trinitrotoluene explosive, B explosive, TNT-Al, HBX-3, octol explosive;
in some embodiments, the first dissolution temperature is 50-100 ℃;
in some embodiments, the first predetermined period of time is 0.5-5 hours;
in some embodiments, the preset ratio is (1.
The solvents in the examples of the present application were determined based on the solubility of trinitrotoluene in the solvents, and table 1 shows the solubility of trinitrotoluene in different solvents (100 g of solvent).
TABLE 1 solubility of trinitrotoluene in different solvents (100 g of solvent)
As shown in Table 1, trinitrotoluene has a low solubility in water, even at 100 ℃ of water, the solubility is only 0.1475g; in polar protic solvent ethanol, the solubility of trinitrotoluene is not high, and in 95% ethanol at 75 ℃, the solubility of trinitrotoluene is only 19.5g; in specific organic solvents such as chloroform, ethyl acetate, acetone, toluene, pyridine and the like, the solubility of the trinitrotoluene is very high, and is more than 100g at 60 ℃, which shows that the specific solvents can effectively and selectively dissolve the trinitrotoluene in retired ammunition without introducing other impurities which are difficult to separate, and the purity of the trinitrotoluene prepared subsequently is greatly improved.
In addition, the specific temperature of the first dissolution temperature in the examples of the present application is determined based on the solubility of the specific solvent to trinitrotoluene, and since the solubility of the specific solvent to trinitrotoluene is different although it is large, the first dissolution temperature is determined differently for the solvent than for the solvent selected.
And S102, repeatedly heating and cooling the filtrate for a first preset time, and filtering to obtain the final filtrate.
In specific implementation, the filtrate is naturally cooled to a preset cooling temperature, and then is reheated to a second dissolving temperature. And then immediately stopping heating, filtering the filtrate, repeating the processes of naturally cooling, reheating and filtering the filtrate for the first preset times, and combining the filtrates obtained by each filtration to obtain the final filtrate.
In some embodiments, the second dissolution temperature is 50-100 ℃;
in some embodiments, the preset reduced temperature is 0-40 ℃;
in some embodiments, the first predetermined number of times is 5 to 10 times.
S103, cooling and crystallizing the final filtrate, filtering to obtain a crystal product, and drying the crystal product to obtain the final product.
In specific implementation, heating the final filtrate to a third dissolution temperature; and then rapidly cooling the final filtrate at the third dissolution temperature to a rapid cooling temperature, and performing crystallization within a preset crystallization time. As can be seen from the contents in table 1, the solubility of trinitrotoluene in a specific solvent is greatly changed with temperature, so that the solubility of trinitrotoluene in the solvent is rapidly reduced with rapid reduction of temperature, so that a crystal product is precipitated from a final filtrate, and the crystal product precipitated from the final filtrate is obtained by filtering through a positive pressure filter, and the crystal product is trinitrotoluene crystals; and putting the crystal product into a vacuum oven, and drying at a drying temperature and under a vacuum pressure to obtain the final product.
In some embodiments, the third dissolution temperature is 50-100 ℃;
in some embodiments, the rapid cooling temperature is between-5 and 5 ℃;
in some embodiments, the preset crystallization time is 1 to 10 hours;
in some embodiments, the drying temperature is 30 ℃;
in some embodiments, the vacuum pressure is 0.1 to 0.5MPa.
In addition, in the embodiment of the present application, after the above S101, the method for extracting high-purity trinitrotoluene from retired ammunition may also be implemented by directly subjecting the filtrate to natural cooling crystallization, and fig. 2 shows a flow chart of extracting trinitrotoluene by directly subjecting the filtrate to natural cooling crystallization, as shown in fig. 2, the specific steps are as follows:
s201, dissolving retired ammunition in a solvent, and filtering to obtain filtrate.
In specific implementation, the decommissioned ammunition is mixed with a solvent according to a preset proportion to obtain a mixture to be filtered; then heating the mixture to be filtered to a first dissolving temperature, and stirring and preserving heat within a preset time; and filtering the mixture to be filtered while the mixture is hot, and removing insoluble substances in the mixture to be filtered to obtain the filtrate.
In some embodiments, the solvent is one of toluene, acetone, ethyl acetate, chloroform, tetrahydrofuran, dioxane;
in some embodiments, the decommissioned ammunition comprises one or more of storage decommissioned trinitrotoluene explosive, B explosive, TNT-Al, HBX-3, octol explosive;
in some embodiments, the first dissolution temperature is 50-100 ℃;
in some embodiments, the first predetermined period of time is 0.5-5 hours;
in some embodiments, the preset ratio is (1.
For details of this step, refer to the content of S101 above, and details are not described here.
And S202, naturally cooling the filtrate to a target natural cooling temperature, standing, and filtering to obtain a crystal product.
During specific implementation, naturally cooling the filtrate to a target natural cooling temperature, standing for a second preset time, separating out white solids, namely crystal products, from the filtrate along with the volatilization of the solvent and the reduction of the temperature in the standing process, and filtering through a positive pressure filter to obtain the crystal products (trinitrotoluene crystals).
And S203, repeating the processes of dissolving, filtering, naturally cooling and crystallizing and filtering the crystal product for a second preset number of times.
In specific implementation, the processes of dissolving, filtering, naturally cooling and crystallizing and filtering the crystal products of the S201-S202 are repeated for the second preset times on the crystallized filtrate, and the obtained crystal products are combined together.
And S204, drying the crystal product to obtain a final product.
In specific implementation, all the crystal products combined together are put into a vacuum oven and dried at a drying temperature and a vacuum pressure to obtain the final product.
In some embodiments, the target free cooling temperature is 0-30 ℃;
in some embodiments, the second preset time period is 0.5-5h;
in some embodiments, the second predetermined number of times is 3 to 5 times;
in some embodiments, the drying temperature is 30 ℃;
in some embodiments, the vacuum pressure is 0.1 to 0.5MPa.
Based on the method for extracting high-purity trinitrotoluene from retired ammunition provided by the embodiment, the obtained final product is trinitrotoluene crystals, and the purity is more than 99%.
In order to make the present application more clearly understood by those skilled in the art, a method for extracting high-purity trinitrotoluene from retired ammunition as described herein will now be described in detail by way of the following examples.
Example one
S101, dissolving retired ammunition in a solvent, and filtering to obtain filtrate.
In specific implementation, the retired ladder black aluminum explosive is added into an ethyl acetate solvent at room temperature, wherein the ratio of the retired ladder black aluminum explosive to the ethyl acetate is 1. And slowly heating the mixture to be filtered to 100 ℃, stirring and preserving heat for 1h. The mixture to be filtered is then filtered while hot to remove insoluble matter from the mixture to be filtered, yielding a filtrate.
And S102, repeatedly heating and cooling the filtrate for a first preset time, and filtering to obtain the final filtrate.
In specific implementation, the filtrate is naturally cooled to 40 ℃, and then is heated to 100 ℃. And then immediately stopping heating, filtering the filtrate, repeating the processes of naturally cooling, reheating and filtering the filtrate for 6 times, and combining the filtrates obtained by each filtration to obtain the final filtrate.
And S103, cooling and crystallizing the final filtrate, filtering to obtain a crystal product, and drying the crystal product to obtain the final product.
In specific implementation, heating the final filtrate to 100 ℃; and then, quickly cooling the final filtrate at the temperature of 100 ℃ to 0 ℃, along with the rapid reduction of the temperature, reducing the solubility of the trinitrotoluene in the solvent, precipitating a crystal product from the final filtrate, and filtering by using a positive pressure filter to obtain the crystal product precipitated from the final filtrate, wherein the crystal product is trinitrotoluene crystals. And (3) putting the crystal product into a vacuum oven, and drying at room temperature and under the pressure of 0.1MPa to obtain the final product.
Fig. 3 shows the nmr hydrogen spectrum of the final product obtained in this example, as shown in fig. 3, 1 H-NMR (400MHz, DMSO-D6) delta 9.02,2.56ppm, and it can be seen that CH (9.02 ppm) and CH 3 (2.56 ppm), benzene ring hydrogen and methyl hydrogen in trinitrotoluene respectively, no other peak appears, which proves that only benzene ring hydrogen and methyl hydrogen exist in the final product obtained by the embodiment and are consistent with the structure of trinitrotoluene.
Fig. 4 shows the ir spectrum of the final product obtained in this example, and as shown in fig. 4, two peaks (1536.17, 1345.05) in the ir spectrum indicate the presence of nitro group, which confirms that the nitro group is present in the final product obtained in this example and matches with trinitrotoluene.
FIG. 5 shows the final product obtained in this example 13 C-APT NMR spectrum, as shown in FIG. 5, the peak value of 123.04ppm represents the benzene ring Carbon (CH) at the 3,5-position in trinitrotoluene, and the peak value of 15.41ppm represents the methyl Carbon (CH) in trinitrotoluene 3 ) The peaks at 133.39ppm, 146.16ppm and 151.31ppm characterize the carbon of the benzene ring at the 4-position (methyl para-position), the carbon of the benzene ring at the 2,6-position (methyl ortho-position) and the carbon of the benzene ring at the 1-position, which is consistent with the structure of trinitrotoluene, and no other peaks appear, proving that no other impurities exist in the final product. In combination with the characterizations of fig. 3, 4, and 5, the final product was determined to be trinitrotoluene.
Fig. 6 shows a HPLC detection chart of the final product obtained in this example, and as shown in fig. 6, it can be seen that the purity of trinitrotoluene in the final product of this example is 99.43%.
Example two
S101, dissolving retired ammunition in a solvent, and filtering to obtain filtrate.
In specific implementation, the decommissioned trinitrotoluene explosive is added into a toluene solvent at room temperature, wherein the ratio of the decommissioned trinitrotoluene explosive to toluene is 1. And slowly heating the mixture to be filtered to 60 ℃, stirring and preserving heat for 1h. The mixture to be filtered is then filtered while hot to remove insoluble substances from the mixture to be filtered, yielding a filtrate.
And S102, repeatedly heating and cooling the filtrate for the first preset times, and filtering to obtain the final filtrate.
In specific implementation, the filtrate is naturally cooled to 25 ℃, and then is reheated to 60 ℃. And then immediately stopping heating, filtering the filtrate, repeating the processes of naturally cooling, reheating and filtering the filtrate for 5 times, and combining the filtrates obtained by each filtration to obtain the final filtrate.
S103, cooling and crystallizing the final filtrate, filtering to obtain a crystal product, and drying the crystal product to obtain the final product.
In specific implementation, the final filtrate is heated to 60 ℃; and then, rapidly cooling the final filtrate at the temperature of 60 ℃ to 20 ℃, along with rapid reduction of the temperature, reducing the solubility of the trinitrotoluene in the solvent, precipitating a crystal product from the final filtrate, and filtering by using a positive pressure filter to obtain the crystal product precipitated from the final filtrate, wherein the crystal product is trinitrotoluene crystals. And putting the crystal product into a vacuum oven, and drying at room temperature under the pressure of 0.1MPa to obtain the final product.
Fig. 7 shows the nmr hydrogen spectrum of the final product obtained in this example, as shown in fig. 7, 1 H-NMR (400MHz, DMSO-D6) delta 9.02,2.56ppm, and it can be seen that CH (9.02 ppm) and CH 3 (2.56 ppm), benzene ring hydrogen and methyl hydrogen in trinitrotoluene respectively, no other peak appears, which proves that only benzene ring hydrogen and methyl hydrogen exist in the final product obtained by the embodiment and are consistent with the structure of trinitrotoluene.
Fig. 8 shows an HPLC detection chart of the final product obtained in this example, and as shown in fig. 8, it can be seen that the purity of trinitrotoluene in the final product of this example is 99.92%.
EXAMPLE III
S201, dissolving retired ammunition in a solvent, and filtering to obtain filtrate.
In specific implementation, the ex-service ammunition B explosive is added into an ethyl acetate solvent at room temperature, wherein the ratio of the ex-service ammunition B explosive to the ethyl acetate is 1. And slowly heating the mixture to be filtered to 50 ℃, stirring and preserving heat for 0.5h. The mixture to be filtered is then filtered while hot to remove insoluble substances from the mixture to be filtered, yielding a filtrate.
And S202, naturally cooling the filtrate to a target natural cooling temperature, standing, and filtering to obtain a crystal product.
In specific implementation, the obtained filtrate is naturally cooled to 25 ℃, and after standing for 2 hours, white solids, namely crystal products, can be separated out from the filtrate along with the volatilization of the solvent and the reduction of the temperature in the standing process, and the crystal products (trinitrotoluene crystals) are obtained by filtering through a positive pressure filter.
And S203, repeating the processes of dissolving, filtering, naturally cooling and crystallizing and filtering the crystal product for a second preset number of times.
In specific implementation, the processes of dissolving, filtering, naturally cooling and crystallizing and filtering the crystal products of the S201-S202 are repeated for 3 times again on the filtrate after crystallization, and the obtained crystal products are combined together.
And S204, drying the crystal product to obtain a final product.
In specific implementation, all the crystal products combined together are put into a vacuum oven and dried at room temperature and under the drying pressure of 0.1MPa to obtain the final product.
Fig. 9 shows the nmr hydrogen spectrum of the final product obtained in this example, as shown in fig. 9, 1 H-NMR(400MHz,DMSO-D6)δ9.02,2.56ppmit can be seen that CH (9.02 ppm) and CH 3 (2.56 ppm), benzene ring hydrogen and methyl hydrogen in trinitrotoluene respectively, no other peak appears, which proves that only benzene ring hydrogen and methyl hydrogen exist in the final product obtained by the embodiment and are consistent with the structure of trinitrotoluene.
Fig. 10 shows an HPLC detection chart of the final product obtained in this example, and as shown in fig. 10, it can be seen that the purity of trinitrotoluene in the final product of this example is 99.54%.
Example four
S101, dissolving retired ammunition in a solvent, and filtering to obtain filtrate.
In specific implementation, the decommissioned trinitrotoluene explosive is added into an ethyl acetate solvent at room temperature, wherein the ratio of the decommissioned trinitrotoluene explosive to the ethyl acetate is 1. And slowly heating the mixture to be filtered to 60 ℃, stirring and preserving heat for 1h. The mixture to be filtered is then filtered while hot to remove insoluble matter from the mixture to be filtered, yielding a filtrate.
And S102, repeatedly heating and cooling the filtrate for the first preset times, and filtering to obtain the final filtrate.
In specific implementation, the filtrate is naturally cooled to 25 ℃, and then is reheated to 60 ℃. And then immediately stopping heating, filtering the filtrate, repeating the processes of naturally cooling, reheating and filtering the filtrate for 5 times, and combining the filtrates obtained by each filtration to obtain the final filtrate.
S103, cooling and crystallizing the final filtrate, filtering to obtain a crystal product, and drying the crystal product to obtain the final product.
In specific implementation, the final filtrate is heated to 60 ℃; and then, rapidly cooling the final filtrate at the temperature of 60 ℃ to 20 ℃, along with rapid reduction of the temperature, reducing the solubility of the trinitrotoluene in the solvent, precipitating a crystal product from the final filtrate, and filtering by using a positive pressure filter to obtain the crystal product precipitated from the final filtrate, wherein the crystal product is trinitrotoluene crystals. And (3) putting the crystal product into a vacuum oven, and drying at room temperature and under the pressure of 0.1MPa to obtain the final product.
The final product obtained in this example was subjected to nuclear magnetic resonance hydrogen spectroscopy and HPLC detection, and the nuclear magnetic resonance hydrogen spectroscopy 1 H-NMR (400MHz, DMSO-D6) delta 9.02,2.56ppm, CH (9.02 ppm) and CH 3 (2.56 ppm), which are benzene ring hydrogen and methyl hydrogen in trinitrotoluene respectively, and no other peak appears, which proves that only benzene ring hydrogen and methyl hydrogen exist in the final product obtained in the embodiment and are consistent with the structure of trinitrotoluene; the purity of the final product was 99.9% by HPLC.
EXAMPLE five
S201, dissolving retired ammunition in a solvent, and filtering to obtain filtrate.
In specific implementation, the ex-service ammunition B explosive is added into an ethyl acetate solvent at room temperature, wherein the ratio of the ex-service ammunition B explosive to the ethyl acetate is 1. And slowly heating the mixture to be filtered to 60 ℃, stirring and preserving heat for 1h. The mixture to be filtered is then filtered while hot to remove insoluble substances from the mixture to be filtered, yielding a filtrate.
And S202, naturally cooling the filtrate to a target natural cooling temperature, standing, and filtering to obtain a crystal product.
In specific implementation, the obtained filtrate is naturally cooled to 20 ℃, and after standing for 2 hours, white solids, namely crystal products, can be separated out from the filtrate along with the volatilization of the solvent and the reduction of the temperature in the standing process, and the crystal products (trinitrotoluene crystals) are obtained by filtering through a positive pressure filter.
And S203, repeating the processes of dissolving, filtering, naturally cooling and crystallizing and filtering the crystal product for a second preset number of times.
In specific implementation, the processes of dissolving, filtering, naturally cooling and crystallizing and filtering the crystal products of the S201-S202 are repeated for 3 times again on the filtrate after crystallization, and the obtained crystal products are combined together.
And S204, drying the crystal product to obtain a final product.
In specific implementation, all the crystal products combined together are put into a vacuum oven and dried at room temperature and under the drying pressure of 0.1MPa to obtain the final product.
The final product obtained in this example was subjected to nuclear magnetic resonance hydrogen spectroscopy and HPLC detection, and the nuclear magnetic resonance hydrogen spectroscopy 1 H-NMR (400MHz, DMSO-D6) delta 9.02,2.56ppm, CH (9.02 ppm) and CH 3 (2.56 ppm), which are benzene ring hydrogen and methyl hydrogen in trinitrotoluene respectively, and no other peak appears, which proves that only benzene ring hydrogen and methyl hydrogen exist in the final product obtained in the embodiment and are consistent with the structure of trinitrotoluene; the purity of the final product was 99.5% by HPLC.
Example six
S101, dissolving retired ammunition in a solvent, and filtering to obtain filtrate.
In specific implementation, the decommissioned Octol explosive is added into an ethyl acetate solvent at room temperature, wherein the ratio of the decommissioned Octol explosive to the ethyl acetate is 1. And slowly heating the mixture to be filtered to 60 ℃, stirring and preserving heat for 1h. The mixture to be filtered is then filtered while hot to remove insoluble substances from the mixture to be filtered, yielding a filtrate.
And S102, repeatedly heating and cooling the filtrate for a first preset time, and filtering to obtain the final filtrate.
In specific implementation, the filtrate is naturally cooled to 25 ℃, and then is reheated to 60 ℃. And then immediately stopping heating, filtering the filtrate, repeating the processes of naturally cooling, reheating and filtering the filtrate for 5 times, and combining the filtrates obtained by each filtration to obtain the final filtrate.
And S103, cooling and crystallizing the final filtrate, filtering to obtain a crystal product, and drying the crystal product to obtain the final product.
In specific implementation, the final filtrate is heated to 60 ℃; and then, rapidly cooling the final filtrate at the temperature of 60 ℃ to 0 ℃, along with the rapid reduction of the temperature, reducing the solubility of the trinitrotoluene in the solvent, separating out a crystal product from the final filtrate, and filtering through a positive pressure filter to obtain the crystal product separated out from the final filtrate, wherein the crystal product is trinitrotoluene crystals. And putting the crystal product into a vacuum oven, and drying at room temperature under the pressure of 0.1MPa to obtain the final product.
The final product obtained in this example was subjected to nuclear magnetic resonance hydrogen spectroscopy and HPLC detection, and the nuclear magnetic resonance hydrogen spectroscopy 1 H-NMR (400MHz, DMSO-D6) delta 9.02,2.56ppm, CH (9.02 ppm) and CH 3 (2.56 ppm), which are benzene ring hydrogen and methyl hydrogen in trinitrotoluene respectively, and no other peak appears, which proves that only benzene ring hydrogen and methyl hydrogen exist in the final product obtained in the embodiment and are consistent with the structure of trinitrotoluene; the purity of the final product was 99.5% by HPLC.
EXAMPLE seven
S101, dissolving retired ammunition in a solvent, and filtering to obtain a filtrate.
In specific implementation, the decommissioned HBX-3 explosive is added into a toluene solvent at room temperature, wherein the ratio of the decommissioned HBX-3 explosive to the toluene is 1. And slowly heating the mixture to be filtered to 80 ℃, stirring and preserving heat for 1h. The mixture to be filtered is then filtered while hot to remove insoluble substances from the mixture to be filtered, yielding a filtrate.
And S102, repeatedly heating and cooling the filtrate for the first preset times, and filtering to obtain the final filtrate.
In specific implementation, the filtrate is naturally cooled to 25 ℃, and then is reheated to 80 ℃. And then immediately stopping heating, filtering the filtrate, repeating the processes of naturally cooling, reheating and filtering the filtrate for 5 times, and combining the filtrates obtained by each filtration to obtain the final filtrate.
S103, cooling and crystallizing the final filtrate, filtering to obtain a crystal product, and drying the crystal product to obtain the final product.
In specific implementation, heating the final filtrate to 80 ℃; and then, rapidly cooling the final filtrate at the temperature of 80 ℃ to 0 ℃, along with the rapid reduction of the temperature, reducing the solubility of the trinitrotoluene in the solvent, separating out a crystal product from the final filtrate, and filtering through a positive pressure filter to obtain the crystal product separated out from the final filtrate, wherein the crystal product is trinitrotoluene crystals. And (3) putting the crystal product into a vacuum oven, and drying at room temperature and under the pressure of 0.1MPa to obtain the final product.
The final product obtained in this example was subjected to nuclear magnetic resonance hydrogen spectroscopy and HPLC detection, and the nuclear magnetic resonance hydrogen spectroscopy 1 H-NMR (400MHz, DMSO-D6) delta 9.02,2.56ppm, CH (9.02 ppm) and CH 3 (2.56 ppm) which are benzene ring hydrogen and methyl hydrogen in trinitrotoluene respectively, and no other peaks appear, which proves that only benzene ring hydrogen and methyl hydrogen exist in the final product obtained by the embodiment and are consistent with the structure of trinitrotoluene; the purity of the final product was 99.4% by HPLC.
The embodiment of the application provides a method for extracting high-purity trinitrotoluene from retired ammunition, which comprises the steps of selectively dissolving trinitrotoluene in retired ammunition by using a specific solvent with a preset proportion at a preset temperature, removing insoluble substances, and selectively crystallizing and separating out high-purity trinitrotoluene crystals by using the difference of the solubility of trinitrotoluene in a filtrate of the specific solvent along with the change of the temperature, and has the following advantages:
(1) Specific solvent, temperature and ratio are selected, trinitrotoluene extracted from retired ammunition is high in purity, the solvent can be reused, and production cost and pollution to the environment are reduced.
(2) The method selects a recrystallization process to separate and purify trinitrotoluene in decommissioned ammunition, has simple process, and is favorable for promoting the decommissioning conversion application process of energetic materials.
(3) The method is a wet process, all steps and reaction conditions in the process are safe and controllable, the safety risk in the production flow is small, the types of the ex-service ammunition which can be applied are numerous, and the application range is wide.
It should be noted that, in the present specification, the embodiments are all described in a progressive manner, each embodiment focuses on differences from other embodiments, and the same and similar parts among the embodiments may be referred to each other.
The technical solutions provided by the present application are described in detail above, and the principles and embodiments of the present application are described herein by using specific examples, which are only used to help understanding the present application, and the content of the present description should not be construed as limiting the present application. While various modifications of the illustrative embodiments and applications will be apparent to those skilled in the art based upon this disclosure, it is not necessary or necessary to exhaustively enumerate all embodiments, and all obvious variations and modifications can be resorted to, falling within the scope of the disclosure.
Claims (9)
1. A method for extracting high-purity trinitrotoluene from retired ammunition is characterized by comprising the following steps:
dissolving retired ammunition in a solvent, and filtering to obtain a filtrate, wherein the solvent is determined based on the solubility of trinitrotoluene in the solvent;
heating and cooling the filtrate for the first preset times, and filtering to obtain final filtrate, wherein the final filtrate is used for crystallization;
and cooling and crystallizing the final filtrate, filtering to obtain a crystal product, and drying the crystal product to obtain a final product, wherein the final product is trinitrotoluene crystal, and the purity of the final product is more than 99%.
2. The method for extracting high-purity trinitrotoluene from retired ammunition according to claim 1, wherein retired ammunition is dissolved in a solvent, and a filtrate is obtained by filtration, and the method comprises the following steps:
mixing the retired ammunition and the solvent according to a preset proportion to obtain a mixture to be filtered;
heating the mixture to be filtered to a first dissolving temperature, and stirring and preserving heat within a first preset time;
and filtering the mixture to be filtered while the mixture is hot, and removing insoluble substances in the mixture to be filtered to obtain the filtrate.
3. The method for extracting high-purity trinitrotoluene from retired ammunition according to claim 1, wherein the filtrate is repeatedly heated, cooled and filtered for a first preset number of times to obtain a final filtrate, and the method specifically comprises the following steps:
naturally cooling the filtrate to a preset cooling temperature, and then reheating to a second dissolving temperature;
immediately stopping heating, and filtering the filtrate;
and repeating the processes of naturally cooling, reheating and filtering the filtrate for a first preset number of times, and combining the filtrates obtained by each filtration to obtain the final filtrate.
4. The method for extracting high-purity trinitrotoluene from retired ammunition as claimed in claim 1, wherein the final filtrate is cooled and crystallized, filtered to obtain crystal product, and dried to obtain final product, and the method comprises the following steps:
heating the final filtrate to a third dissolution temperature;
rapidly cooling the final filtrate at the third dissolving temperature to a rapid cooling temperature, crystallizing within a preset crystallization time, and filtering through a positive pressure filter to obtain the crystal product separated out from the final filtrate, wherein the crystal product is trinitrotoluene crystal;
and putting the crystal product into a vacuum oven, and drying at a drying temperature and under a vacuum pressure to obtain the final product.
5. The method for extracting high-purity trinitrotoluene from retired ammunition according to claim 1, wherein after the retired ammunition is dissolved in a solvent and filtered to obtain a filtrate, the method further comprises:
naturally cooling the filtrate to a target natural cooling temperature, standing for a second preset time, and filtering to obtain the crystal product;
repeating the processes of dissolving, filtering, natural cooling crystallization and filtering the crystal product for a second preset number of times;
and drying the crystal product to obtain the final product.
6. A method of extracting high purity trinitrotoluene from decommissioned ammunition according to claim 2, characterized by comprising at least one of the following features:
(1) The solvent is one of toluene, acetone, ethyl acetate, chloroform, tetrahydrofuran and dioxane;
(2) The ex-service ammunition comprises one or more of trinitrotoluene explosive, B explosive, TNT-Al, HBX-3 and Octol explosive which are ex-service in storage;
(3) The first dissolving temperature is 50-100 ℃;
(4) The first preset time is 0.5-5h;
(5) The preset ratio is (1.
7. A method of extracting high purity trinitrotoluene from decommissioned ammunition according to claim 3, characterized by comprising at least one of the following features:
(1) The second dissolving temperature is 50-100 ℃;
(2) The preset cooling temperature is 0-40 ℃;
(3) The first preset times are 5-10 times.
8. A method of extracting high purity trinitrotoluene from decommissioned ammunition according to claim 4, characterized by comprising at least one of the following features:
(1) The third dissolving temperature is 50-100 ℃;
(2) The rapid cooling temperature is-5 to 5 ℃;
(3) The preset crystallization time is 1-10h;
(3) The drying temperature is 30 ℃;
(4) The vacuum pressure is 0.1-0.5MPa.
9. A method of extracting high purity trinitrotoluene from decommissioned ammunition according to claim 5, characterized by comprising at least one of the following features:
(1) The target natural cooling temperature is 0-30 ℃;
(2) The second preset time is 0.5-5h;
(3) The second preset times is 3-5 times.
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| US6777586B1 (en) * | 2003-05-23 | 2004-08-17 | Gradient Technology | Reclaiming RDX and TNT from composition B and composition B containing military shells |
| CN104311501A (en) * | 2014-09-15 | 2015-01-28 | 甘肃银光化学工业集团有限公司 | Waste HMX and TNT mixed explosive recovery method |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6777586B1 (en) * | 2003-05-23 | 2004-08-17 | Gradient Technology | Reclaiming RDX and TNT from composition B and composition B containing military shells |
| CN104311501A (en) * | 2014-09-15 | 2015-01-28 | 甘肃银光化学工业集团有限公司 | Waste HMX and TNT mixed explosive recovery method |
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| 吴翼 等: "用溶剂萃取法分离废旧梯黑铝炸药TNT组分的研究", 《兵工学报》, vol. 36, pages 348 - 352 * |
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