CN85105850A - The preparation of dinitrobenzene benzo furoxan and its esters - Google Patents
The preparation of dinitrobenzene benzo furoxan and its esters Download PDFInfo
- Publication number
- CN85105850A CN85105850A CN 85105850 CN85105850A CN85105850A CN 85105850 A CN85105850 A CN 85105850A CN 85105850 CN85105850 CN 85105850 CN 85105850 A CN85105850 A CN 85105850A CN 85105850 A CN85105850 A CN 85105850A
- Authority
- CN
- China
- Prior art keywords
- preparation
- benzo furoxan
- dinitrobenzene benzo
- dinitrobenzene
- furoxan
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- OKEAMBAZBICIFP-UHFFFAOYSA-N 3-oxido-2,1,3-benzoxadiazol-3-ium Chemical compound C1=CC=CC2=[N+]([O-])ON=C21 OKEAMBAZBICIFP-UHFFFAOYSA-N 0.000 title claims abstract description 20
- 238000002360 preparation method Methods 0.000 title claims abstract description 20
- WDCYWAQPCXBPJA-UHFFFAOYSA-N 1,3-dinitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC([N+]([O-])=O)=C1 WDCYWAQPCXBPJA-UHFFFAOYSA-N 0.000 title claims abstract description 10
- 150000002148 esters Chemical class 0.000 title abstract description 3
- AGUIVNYEYSCPNI-UHFFFAOYSA-N N-methyl-N-picrylnitramine Chemical group [O-][N+](=O)N(C)C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O AGUIVNYEYSCPNI-UHFFFAOYSA-N 0.000 claims abstract description 8
- 238000000034 method Methods 0.000 claims abstract description 8
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims abstract description 6
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims abstract description 6
- 229910052788 barium Inorganic materials 0.000 claims abstract description 6
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 claims abstract description 6
- 229910052700 potassium Inorganic materials 0.000 claims abstract description 6
- 239000011591 potassium Substances 0.000 claims abstract description 6
- 239000002994 raw material Substances 0.000 claims abstract description 6
- 150000003839 salts Chemical class 0.000 claims abstract description 6
- 229910052708 sodium Inorganic materials 0.000 claims abstract description 6
- 239000011734 sodium Substances 0.000 claims abstract description 6
- 238000004519 manufacturing process Methods 0.000 claims abstract description 4
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 3
- 238000000197 pyrolysis Methods 0.000 claims description 3
- SFAXANKELJNWSA-UHFFFAOYSA-N 2-azido-1,3,5-trinitrobenzene Chemical compound [O-][N+](=O)C1=CC([N+]([O-])=O)=C(N=[N+]=[N-])C([N+]([O-])=O)=C1 SFAXANKELJNWSA-UHFFFAOYSA-N 0.000 claims description 2
- 239000002798 polar solvent Substances 0.000 claims description 2
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 239000002360 explosive Substances 0.000 abstract description 5
- 239000000126 substance Substances 0.000 abstract description 3
- 239000000463 material Substances 0.000 abstract description 2
- -1 dinitrobenzene benzo furoxan salt Chemical class 0.000 abstract 1
- 238000009776 industrial production Methods 0.000 abstract 1
- 239000007864 aqueous solution Substances 0.000 description 4
- 159000000000 sodium salts Chemical class 0.000 description 3
- HJRJRUMKQCMYDL-UHFFFAOYSA-N 1-chloro-2,4,6-trinitrobenzene Chemical compound [O-][N+](=O)C1=CC([N+]([O-])=O)=C(Cl)C([N+]([O-])=O)=C1 HJRJRUMKQCMYDL-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- IWOUKMZUPDVPGQ-UHFFFAOYSA-N barium nitrate Chemical compound [Ba+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O IWOUKMZUPDVPGQ-UHFFFAOYSA-N 0.000 description 2
- 159000000009 barium salts Chemical class 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 235000011164 potassium chloride Nutrition 0.000 description 2
- 239000001103 potassium chloride Substances 0.000 description 2
- FGIUAXJPYTZDNR-UHFFFAOYSA-N potassium nitrate Chemical compound [K+].[O-][N+]([O-])=O FGIUAXJPYTZDNR-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 208000006558 Dental Calculus Diseases 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000001540 azides Chemical class 0.000 description 1
- WDIHJSXYQDMJHN-UHFFFAOYSA-L barium chloride Chemical compound [Cl-].[Cl-].[Ba+2] WDIHJSXYQDMJHN-UHFFFAOYSA-L 0.000 description 1
- 229940045511 barium chloride Drugs 0.000 description 1
- 229910001626 barium chloride Inorganic materials 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 235000010333 potassium nitrate Nutrition 0.000 description 1
- 239000004323 potassium nitrate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000037452 priming Effects 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The present invention is a kind of preparation method of military chemical material.Dinitrobenzene benzo furoxan is a kind of high explosive, is again a kind of important explosive intermediate, and salts such as its sodium, potassium, barium all can be made burster, and preparation method in the past is difficult for realizing suitability for industrialized production.
The present invention proposes with the tetryl that is easy to get and make raw material manufacturing 4,6---the novel method of dinitrobenzene benzo furoxan.The invention allows for 4,6---the preparation approach of dinitrobenzene benzo furoxan salt: promptly with aforesaid method make 4,6---dinitrobenzene benzo furoxan is made intermediate, prepares its esters with it again.Present method is simple, yield is high, and industrial production is easy to implement.
Description
The present invention is a kind of preparation method of military chemical material.
4,6-dinitrobenzene benzo furoxan is a kind of high explosive, and it still is a kind of important explosive intermediate, and its structural formula is (I), and salt such as its sodium, potassium, barium all can be made priming explosive,
Structure is (II), and sylvite detonates functional, detonates easily, and the barium salt sensitivity is low, and is high temperature resistant.
4,6-dinitrobenzene benzo furoxan had multiple preparation method in the past, abroad, and Australian author Spear, Robert J; Norris William P; Read Roger W, at Tech Note-Mater.Res, lab(Aust) 1983 MRL-TN-470 deliver in the recent period and have described 4, the preparation of 6-dinitrobenzene benzo furoxan, so far still make raw material with picryl chloride, by azide denitrogenation preparation again, but its preparation condition harshness of picryl chloride is difficult to obtain; Other method is to prepare by nitrated with the benzo furoxan, China author Lu Mingjiu, Liu Hongyu " war industry's journal " fire, chemical industry fascicle 3 12(1982) publish an article, also prepare with this method, but this method long reaction time, yield is lower.Therefore above-mentioned two kinds of methods all are difficult for realizing suitability for industrialized production.
Purpose of the present invention is exactly with facile raw material-tetryl preparation 4,6-dinitrobenzene benzo furoxan, and with this as intermediate, prepare salt such as its sodium, potassium, barium.
4, the preparation method of 6-dinitrobenzene benzo furoxan: sodiumazide and tetryl are reacted in ethanol or other general polar solvents, the consumption of sodiumazide is greater than theoretical amount, stir down at 15～50 ℃, the thin up after-filtration can obtain faint yellow precipitation, promptly 2,4,6-trinitro-phenylazide is added to pyrolysis denitrogenation in the acetate (temperature of reaction is about 100 ℃) with it, cooling then, thin up after the yellow solid of separating out is washed after filtration, can obtain crude product 4,6-dinitrobenzene benzo furoxan, yield can reach more than 80% in tetryl, can make with extra care with chloroform or acetate etc. again.
Product structure obtains infrared spectra, ultimate analysis, the affirming of organic mass spectrometry and nuclear magnetic resonance spectrum.
4, the preparation method of 6-dinitrobenzene benzo furoxan salt: with the tetryl is that raw material is prepared intermediate 4 by above-mentioned condition, 6-dinitrobenzene benzo furoxan, and water with reaction of sodium bicarbonate, can make its sodium salt as medium about 50 ℃ again; As the aqueous solution of this sodium salt and the reactant aqueous solution of saltpetre or vitriolate of tartar can be made its sylvite; With this sodium-salt aqueous solution and bariumchloride or barium nitrate aqueous solution reaction, can get its barium salt again.
The used basic raw material tetryl of the present invention is cheap Industrial products, and raw material is easy to get.The preparation method is simple, and preparation condition is less demanding, and the reaction times is shorter, and the yield height, equally from tetryl through intermediate 4,6-dinitrobenzene benzo furoxan preparation 4, salts such as the sodium of 6-dinitrobenzene benzo furoxan, potassium, barium, industrial easy to implement, and cost is low.
Claims (3)
1, preparation 4, the method for 6-dinitrobenzene benzo furoxan is characterized by: make 2,4 with tetryl as raw material and reaction of sodium azide, 6-trinitro-phenylazide, in acetate with 2,4,6-trinitro-phenylazide pyrolysis denitrogenation generates 4,6-dinitrobenzene benzo furoxan.
2, preparation method according to claim 1 is characterized by: azido reaction, its solvent are ethanol or other general polar solvents, and temperature of reaction is 15～50 ℃, and the consumption of sodiumazide is greater than theoretical amount, and the pyrolysis denitrification temperature is about 100 ℃.
3, preparation 4, the approach of salt such as the sodium of 6-dinitrobenzene benzo furoxan, potassium, barium is characterized by: be that feedstock production goes out intermediate 4 with the tetryl, 6-dinitrobenzene benzo furoxan, further reaction again, preparation 4, salts such as the sodium of 6-dinitrobenzene benzo furoxan, potassium, barium.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN85105850A CN85105850B (en) | 1985-08-03 | 1985-08-03 | Preparation of nitro benzene-oxidized furan and its salt |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN85105850A CN85105850B (en) | 1985-08-03 | 1985-08-03 | Preparation of nitro benzene-oxidized furan and its salt |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN85105850A true CN85105850A (en) | 1986-01-10 |
| CN85105850B CN85105850B (en) | 1987-02-18 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN85105850A Expired CN85105850B (en) | 1985-08-03 | 1985-08-03 | Preparation of nitro benzene-oxidized furan and its salt |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN85105850B (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102702131A (en) * | 2012-06-29 | 2012-10-03 | 太仓市新星轻工助剂厂 | Method for synthesizing plasticizer 3-nitro furazan-4-methyl ether |
| CN102952124A (en) * | 2011-08-23 | 2013-03-06 | 北京理工大学 | 3,4-bis(1-hydro-5-tetrazolyl)furoxan ionic salt containing energy and preparation method thereof |
| CN103450108A (en) * | 2012-06-04 | 2013-12-18 | 南京理工大学 | Polyaminopolynitrobenzofuroxan metal complex and preparation method thereof |
| CN107501293A (en) * | 2017-10-11 | 2017-12-22 | 中国工程物理研究院化工材料研究所 | Two furazano piperazine nitramine class energetic ion salt and its synthetic method |
-
1985
- 1985-08-03 CN CN85105850A patent/CN85105850B/en not_active Expired
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102952124A (en) * | 2011-08-23 | 2013-03-06 | 北京理工大学 | 3,4-bis(1-hydro-5-tetrazolyl)furoxan ionic salt containing energy and preparation method thereof |
| CN102952124B (en) * | 2011-08-23 | 2016-08-17 | 北京理工大学 | 3,4-double (1-hydrogen-5-tetrazole radical) furoxans are containing energy ion salt and preparation method thereof |
| CN103450108A (en) * | 2012-06-04 | 2013-12-18 | 南京理工大学 | Polyaminopolynitrobenzofuroxan metal complex and preparation method thereof |
| CN102702131A (en) * | 2012-06-29 | 2012-10-03 | 太仓市新星轻工助剂厂 | Method for synthesizing plasticizer 3-nitro furazan-4-methyl ether |
| CN107501293A (en) * | 2017-10-11 | 2017-12-22 | 中国工程物理研究院化工材料研究所 | Two furazano piperazine nitramine class energetic ion salt and its synthetic method |
Also Published As
| Publication number | Publication date |
|---|---|
| CN85105850B (en) | 1987-02-18 |
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