CN103588719B - A kind of octogen and dimethyl sulfoxide (DMSO) complex compound and preparation method thereof - Google Patents
A kind of octogen and dimethyl sulfoxide (DMSO) complex compound and preparation method thereof Download PDFInfo
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- CN103588719B CN103588719B CN201310602054.0A CN201310602054A CN103588719B CN 103588719 B CN103588719 B CN 103588719B CN 201310602054 A CN201310602054 A CN 201310602054A CN 103588719 B CN103588719 B CN 103588719B
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- Prior art keywords
- dmso
- complex compound
- octogen
- hmx
- dimethyl sulfoxide
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- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 title claims abstract description 125
- 239000000028 HMX Substances 0.000 title claims abstract description 51
- UZGLIIJVICEWHF-UHFFFAOYSA-N octogen Chemical compound [O-][N+](=O)N1CN([N+]([O-])=O)CN([N+]([O-])=O)CN([N+]([O-])=O)C1 UZGLIIJVICEWHF-UHFFFAOYSA-N 0.000 title claims abstract description 51
- 150000001875 compounds Chemical class 0.000 title claims abstract description 36
- 238000002360 preparation method Methods 0.000 title claims abstract description 14
- 229960001760 dimethyl sulfoxide Drugs 0.000 claims abstract description 19
- 239000007864 aqueous solution Substances 0.000 claims abstract description 12
- 239000002904 solvent Substances 0.000 claims abstract description 7
- 238000003756 stirring Methods 0.000 claims abstract description 7
- 239000000243 solution Substances 0.000 claims abstract description 6
- 238000010438 heat treatment Methods 0.000 claims abstract description 5
- 239000007787 solid Substances 0.000 claims abstract description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 abstract description 2
- 238000004519 manufacturing process Methods 0.000 abstract description 2
- 239000013078 crystal Substances 0.000 description 8
- 238000000034 method Methods 0.000 description 6
- 238000010926 purge Methods 0.000 description 4
- 238000010792 warming Methods 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 2
- 239000002360 explosive Substances 0.000 description 2
- -1 wherein Substances 0.000 description 2
- DVARTQFDIMZBAA-UHFFFAOYSA-O ammonium nitrate Chemical class [NH4+].[O-][N+]([O-])=O DVARTQFDIMZBAA-UHFFFAOYSA-O 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 229910002056 binary alloy Inorganic materials 0.000 description 1
- 230000000536 complexating effect Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000005474 detonation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000000329 molecular dynamics simulation Methods 0.000 description 1
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000001149 thermolysis Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
- C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a kind of octogen and dimethyl sulfoxide (DMSO) complex compound and preparation method thereof, described preparation method comprises the following steps: step one: octogen be dissolved in dimethyl sulfoxide (DMSO) or dimethyl sulphoxide aqueous solution, stirring heating, makes solid all dissolve; Step 2: by direct for the solution of step one decrease temperature crystalline; Step 3: step 2 decrease temperature crystalline thing is filtered under dry air flowing and drains, by nonpolar or that polarity is little easy volatile solvent drip wash, then drain under dry air flowing, obtain the complex compound of varigrained octogen and dimethyl sulfoxide (DMSO).HMX/DMSO complex compound prepared by the present invention is the mol ratio forming HMX and DMSO on molecule is the complex compound of 1:1 or 1:2, operation steps is simple, reaction conditions is gentle, production cost is low, rapidly and efficiently, the DMSO solution being dissolved in different concns by HMX obtains varigrained HMX/DMSO complex compound in preparation.
Description
Technical field
The invention belongs to the field of energetic material technology of preparing, be specifically related to a kind of octogen and dimethyl sulfoxide (DMSO) complex compound and preparation method thereof.
Background technology
Octogen (HMX) is one of explosive that in existing single chmical compound explosive, the over-all properties such as crystalline density, detonation energy, thermal safety is best, has been widely used in all kinds of weapon powder charge.Because octogen is multi-crystalline compounds, in intermolecular and molecule, there is strong or weak H-bonding capability, since nineteen fifty-three, find that octogen can form complex compound with tens kinds of solvents, the complex compound having HMX and DMF be wherein widely studied, and utilize the content analysis of quantitative composition for HMX in RDX of HMX and DMF, also adopt molecular dynamics simulation HMX/DMF complex compound to be carried out to the research of structure and Intermolecular Forces.And complexing action also may play a role in the purifying of product, recycling etc., it also may be the effective way that sense or insensitiveness fall in some ammonium nitrate compounds.Existing document is little to the report of HMX and DMSO complex compound, is only described as the equimolecular solvate of the instability that can obtain, also there are no the research of physicochemical property.
Summary of the invention
The object of this invention is to provide a kind of octogen and dimethyl sulfoxide (DMSO) complex compound and preparation method thereof, it is the method preparing HMX/DMSO complex compound in binary system HMX being dissolved in DMSO or the DMSO aqueous solution, wherein, HMX is dissolved in DMSO or the DMSO aqueous solution and is mixed with different concentration, will obtain varigrained HMX/DMSO complex compound.
In order to reach above-mentioned technique effect, the present invention takes following technical scheme:
A preparation method for octogen and dimethyl sulfoxide (DMSO) complex compound, comprises the following steps:
Step one: octogen is dissolved in dimethyl sulfoxide (DMSO) or dimethyl sulphoxide aqueous solution, stirring heating, solid is all dissolved;
Step 2: by direct for the solution of step one decrease temperature crystalline, the rate of temperature fall of its decrease temperature crystalline is 1 DEG C/min ~ 10 DEG C/min;
Step 3: step 2 decrease temperature crystalline thing is filtered under dry air flowing and drains, by nonpolar or that polarity is little easy volatile solvent drip wash, then drain under dry air flowing, obtain the complex compound of varigrained octogen and dimethyl sulfoxide (DMSO).
In step 2, the crystallisate of decrease temperature crystalline is due at room temperature unstable, easily absorbs water, and therefore needs to filter under dry air flowing to drain, then by nonpolar or that polarity is little easy volatile solvent drip wash, drains under dry air flowing.According to embodiments of the invention, in above-mentioned method, in described dimethyl sulphoxide solution, the content of water is 0 ~ 15%.
According to embodiments of the invention, in above-mentioned method, the temperature of described heating is 50 DEG C ~ 90 DEG C.
According to embodiments of the invention, in above-mentioned method, described easy volatile solvent is the one in ether, acetone, tetracol phenixin.
A kind of octogen and dimethyl sulfoxide (DMSO) complex compound, adopt above-mentioned preparation method's preparation and obtain.
The present invention compared with prior art, has following beneficial effect:
HMX/DMSO complex compound prepared by present method is the mol ratio forming HMX and DMSO on molecule is the complex compound of 1:1 or 1:2, operation steps is simple, reaction conditions is gentle, production cost is low, rapidly and efficiently, the DMSO solution being dissolved in different concns by HMX obtains varigrained HMX/DMSO complex compound in preparation.
Accompanying drawing explanation
Fig. 1 is the single crystal diffraction space structure figure of HMX.
Fig. 2 is the single crystal diffraction space structure figure of DMSO.
The single crystal diffraction space structure figure of Fig. 3 to be molecule mol ratio be HMX/DMSO complex compound of 1:2.
The DSC figure of Fig. 4 to be embodiment 2 general molecular ratio be HMX/DMSO complex compound of 1:2.
Embodiment
Below in conjunction with embodiments of the invention, the invention will be further elaborated.
Embodiment 1
DMSO9.5g is joined the DMSO aqueous solution being made into water content 5% in the water of 0.5g, 5.5gHMX is added in the DMSO aqueous solution of 10g, be warming up to 80 DEG C, fully stir; With the speed decrease temperature crystalline of 1 DEG C/min; Crystal filters and drains under the purging of dry air, with 30ml ether drip wash once, obtaining median size is the HMX/DMSO complex compound 6.1g of 213 μm.
Embodiment 2
102gHMX is added in 150gDMSO, is warmed up to 70 DEG C, fully stirs, with the speed decrease temperature crystalline of 5 DEG C/min, filter under the purging of dry air and drain, with 50ml acetone drip wash once, obtaining median size is the HMX/DMSO complex compound 106g of 152 μm.
Fig. 1 and Fig. 2 respectively illustrates the single crystal diffraction space structure figure of HMX and DMSO, Fig. 3 shows the single crystal diffraction space structure figure that molecule mol ratio that the present embodiment prepares is the HMX/DMSO complex compound of 1:2, and as can be seen from the figure HMX/DMSO complex compound defines the complex compound that HMX:DMSO mol ratio is 1:2 on molecule.
Fig. 4 shows the DSC figure that molecule mol ratio that the present embodiment prepares is the HMX/DMSO complex compound of 1:2, and DSC detects and shows, near 117 DEG C, first decomposition peak appears in HMX/DMSO, then just occurs phase in version peak and the thermolysis peak of HMX simple substance.
Embodiment 3
DMSO9g is added the aqueous solution being made into water content 10% in the water of 1g, 3.5gHMX is added in the aqueous solution of 10g, be warming up to 90 DEG C, fully stir; With the speed decrease temperature crystalline of 10 DEG C/min; Crystal filters and drains under the purging of dry air, with 30ml ether drip wash once, obtaining median size is the HMX/DMSO complex compound 3.2g of 89 μm.
Embodiment 4
DMSO8.5g is added the aqueous solution being made into water content 15% in the water of 1.5g, 1.5gHMX is added in the aqueous solution of 10g, be warming up to 60 DEG C, fully stir; With the speed decrease temperature crystalline of 10 DEG C/min; Crystal filters and drains under the purging of dry air, with 30ml ether drip wash once, obtaining median size is the HMX/DMSO complex compound 1.2g of 89 μm.
Although with reference to explanatory embodiment of the present invention, invention has been described here, above-described embodiment is only the present invention's preferably embodiment, embodiments of the present invention are not restricted to the described embodiments, should be appreciated that, those skilled in the art can design a lot of other amendment and embodiment, these amendments and embodiment will drop within spirit disclosed in the present application and spirit.
Claims (3)
1. a preparation method for octogen and dimethyl sulfoxide (DMSO) complex compound, is characterized in that comprising the following steps:
Step one: octogen be dissolved in dimethyl sulphoxide aqueous solution, stirring heating, makes solid all dissolve;
Step 2: by direct for the solution of step one decrease temperature crystalline;
Step 3: step 2 decrease temperature crystalline thing is filtered under dry air flowing and drains, by nonpolar or that polarity is little easy volatile solvent drip wash, then drain under dry air flowing, obtain the complex compound of varigrained octogen and dimethyl sulfoxide (DMSO);
The rate of temperature fall of the decrease temperature crystalline wherein described in step 2 is 1 DEG C/min ~ 10 DEG C/min;
In described dimethyl sulphoxide aqueous solution, the content of water is 5 ~ 15%.
2. the preparation method of a kind of octogen according to claim 1 and dimethyl sulfoxide (DMSO) complex compound, is characterized in that described Heating temperature is 50 DEG C ~ 90 DEG C.
3. the preparation method of a kind of octogen according to claim 1 and dimethyl sulfoxide (DMSO) complex compound, is characterized in that described easy volatile solvent is the one in ether, acetone, tetracol phenixin.
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| CN201310602054.0A CN103588719B (en) | 2013-11-25 | 2013-11-25 | A kind of octogen and dimethyl sulfoxide (DMSO) complex compound and preparation method thereof |
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| CN201310602054.0A CN103588719B (en) | 2013-11-25 | 2013-11-25 | A kind of octogen and dimethyl sulfoxide (DMSO) complex compound and preparation method thereof |
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| Publication Number | Publication Date |
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| CN103588719A CN103588719A (en) | 2014-02-19 |
| CN103588719B true CN103588719B (en) | 2016-03-23 |
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| CN115246840B (en) * | 2021-07-13 | 2023-09-26 | 南京理工大学 | HMX hybrid compound, synthesis method and application |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2009051692A (en) * | 2007-08-27 | 2009-03-12 | Nippon Koki Co Ltd | Polyhedral rdx, method for making rdx polyhedral and method for producing spherical rdx |
| CN102320903A (en) * | 2011-06-16 | 2012-01-18 | 中国工程物理研究院化工材料研究所 | Method for preparing high-quality energetic crystal material fine particles |
| CN102503905A (en) * | 2011-09-28 | 2012-06-20 | 中国工程物理研究院化工材料研究所 | Method for preparing porous ultrafine HMX |
-
2013
- 2013-11-25 CN CN201310602054.0A patent/CN103588719B/en not_active Expired - Fee Related
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2009051692A (en) * | 2007-08-27 | 2009-03-12 | Nippon Koki Co Ltd | Polyhedral rdx, method for making rdx polyhedral and method for producing spherical rdx |
| CN102320903A (en) * | 2011-06-16 | 2012-01-18 | 中国工程物理研究院化工材料研究所 | Method for preparing high-quality energetic crystal material fine particles |
| CN102503905A (en) * | 2011-09-28 | 2012-06-20 | 中国工程物理研究院化工材料研究所 | Method for preparing porous ultrafine HMX |
Non-Patent Citations (6)
| Title |
|---|
| HMX/DMSO络合物的制备及表征;陈娅 等;《2013年第二届全国危险物质与安全应急技术研讨会论文集》;20131114;56-59 * |
| HMX与DMF的络合行为;田宏远 等;《含能材料》;20091015;第17卷(第5期);541-543 * |
| HMX的合成工艺研究进展;于娜娜 等;《化工中间体》;20110315(第3期);22-26 * |
| Partial Phase Behavior of HMX/DMSO Solutions;D. Mark Hoffman 等;《Propellants, Explosives, Pyrotechnics》;19991212;第24卷;301-307 * |
| 于海利 等.ＨＭＸ溶液结晶的分子动力学模拟.《含能材料》.2013,第21卷(第5期),589-593. * |
| 重结晶制备超细HMX;汪小艳 等;《爆破》;20130915;第30卷(第3期);125-128 * |
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