CN103788000A - 5-((5-nitro-2H-tetrazole-2-yl)methyl)-1H-tetrazole-1-ol and preparation method thereof - Google Patents
5-((5-nitro-2H-tetrazole-2-yl)methyl)-1H-tetrazole-1-ol and preparation method thereof Download PDFInfo
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Abstract
The invention discloses 5-((5-nitro-2H-tetrazole-2-yl)methyl)-1H-tetrazole-1-ol and a preparation method thereof. The preparation method comprises the steps: preparing an ammonium nitrotetrazole salt by using aminotetrazole through diazotization; then performing an alkylation reaction to prepare 2-(5-nitro-2H-tetrazole-2-yl) acetonitrile; then performing oximation to prepare N'-hydroxyl-2-(5-nitro-2H-tetrazole-2H-yl) ethanamidine; then performing diazotization to obtain N'-hydroxyl-2-(5-nitro-2H-tetrazole-2H-yl) trifluoroacetimidoyl chloride; then performing azidation to prepare N'-hydroxyl-2-(5-nitro-2H-tetrazole-2H-yl) trifluoroacetimidoyl azide; finally cyclizing to prepare 5-((5-nitro-2H-tetrazole-2-yl)methyl)-1H-tetrazole-1-ol. Hydroxyl is introduced on a tetrazole ring so that enthalpies of formation can be reduced and the intermolecular force is increased to ensure that the mechanical sensitivity is reduced; the hydroxyl is introduced on the tetrazole ring so that oxygen balance is favorably improved and the combustion heat is improved; the hydroxyl is introduced on the tetrazole ring so that the density, detonation velocity and detonation pressure of a high-energetic material are facilitated. The high-nitrogen energetic material is widely applied to the fields such as national defense, spaceflight, civil use and the like.
Description
Technical field
The present invention relates to a kind of 5-((5-nitro-2
h-tetrazolium-2-yl) methyl)-1
h-tetrazolium-1-alcohol and preparation method thereof, belongs to the field of chemical synthesis.
Background technology
Unique good characteristics such as tetrazolium class high Energy Density Materials (HEDM) has that nitrogen content is high, high-density, Enthalpies of Formation is high, gas production rate is large and products of combustion is clean, its derivative not only can be made energetic material and use in the field such as national defence and space flight, and is also widely used at civil area.Therefore, especially noticeable to the synthetic and applied research of these compounds.Thomas has synthesized 2-((1
h-tetrazolium-5-yl) methyl)-5-nitro-2
htetrazolium (Thomas M Klapotke,
et al. Synthesis and properties of 5-nitrotetrazole derivatives as new energetic materials[J]. Mater. Chem., 2009,19,2240 – 2252).Its density is 1.802 gcm
-1; Explosion velocity 8588 ms
-1; Detonation pressure 30.2 GPa; Impact sensitivity < 2 J; Friction sensitivity <180 N.Bi Fuqiang, and Fan Xuezhong etc. (insensitive tetrazolium is nonmetal containing progress .[J that can ionic compound]. energetic material 2003,11,231-234) propose to introduce hydroxyl on tetrazole ring and can reduce Enthalpies of Formation and increase Intermolecular Forces, its mechanical sensitivity is reduced; On tetrazole ring, introduce hydroxyl and contribute to improve oxygen balance, improve the combustion heat; On tetrazole ring, introduce density, explosion velocity, detonation pressure that hydroxyl is conducive to improve energetic material.
Summary of the invention
In order to improve 2-((1
h-tetrazolium-5-yl) methyl)-5-nitro-2
hthe performance of tetrazolium, the invention provides a kind of 5-((5-nitro-2
h-tetrazolium-2-yl) methyl)-1
h-tetrazolium-1-alcohol and preparation method thereof, the method raw material is easy to get, cost is low, it is little to pollute, simple to operate, productive rate is higher.
The object of the invention is to be achieved through the following technical solutions:
A kind of 5-((5-nitro-2
h-tetrazolium-2-yl) methyl)-1
h-tetrazolium-1-alcohol, its structural formula is as follows:
The preparation method of above-claimed cpd, its syntheti c route is as follows:
The method comprises the steps:
(1) by 2-(5-nitro-2
h-tetrazolium-2-yl) acetonitrile, oxammonium hydrochloride, sodium bicarbonate add in solvent, and reacting by heating, removes by filter inorganic salt, and solvent removed in vacuo obtains
n'-hydroxyl-2-(5-nitro-2
h-tetrazolium-2-yl) ethanamidine;
(2) by above-mentioned
n'-hydroxyl-2-(5-nitro-2
h-tetrazolium-2-yl) ethanamidine is dissolved in hydrochloric acid soln under certain conditions, drips sodium nitrite in aqueous solution, reacts under heating condition after dripping completely, and after reaction finishes, through extraction, dry dewatering, vacuum-drying obtains
n'-hydroxyl-2-(5-nitro-2
h-tetrazolium-2-yl) imines is for Acetyl Chloride 98Min.;
(3) by above-mentioned
n'-hydroxyl-2-(5-nitro-2
h-tetrazolium-2-yl) imines adds in solvent for Acetyl Chloride 98Min., sodiumazide, under heating condition, reacts, and after reaction finishes, through extraction, dry dewatering, vacuum-drying obtains
n'-hydroxyl-2-(5-nitro-2
h-tetrazolium-2-yl) imines is for acetyl nitrine;
(4) by above-mentioned
n'-hydroxyl-2-(5-nitro-2
h-tetrazolium-2-yl) imines is dissolved in acid and reacts for acetyl nitrine, and after reaction finishes, through extraction, dry dewatering, vacuum-drying obtains 5-((5-nitro-2
h-tetrazolium-2-yl) methyl)-1
h-tetrazolium-1-alcohol.
Wherein, the solvent described in step (1) is selected methyl alcohol, ethanol, water or acetone; Temperature of reaction is 20 ~ 65 ℃, and the reaction times is 0.5 ~ 5 hour.
2-(5-nitro-2 in step (1)
h-tetrazolium-2-yl) mol ratio of acetonitrile and oxammonium hydrochloride is 1:1 ~ 4; 2-(5-nitro-2
h-tetrazolium-2-yl) mol ratio of acetonitrile and sodium bicarbonate is 1:1 ~ 4.
In step (2), temperature of reaction is first 0 ~ 20 ℃, then is 30 ~ 75 ℃, and the reaction times is 1 ~ 6 hour.
In step (2)
n'-hydroxyl-2-(5-nitro-2
h-tetrazolium-2-yl) ethanamidine and hydrochloric acid 1:1 ~ 6;
n'-hydroxyl-2-(5-nitro-2
h-tetrazolium-2-yl) mol ratio of ethanamidine and Sodium Nitrite is 1:1 ~ 6.
Described in step (3), solvent is the mixed solvent of acetone, DMF, NMP and water, and the reaction times is 1 ~ 12 hour, and temperature of reaction is 20 ~ 60 ℃.
In step (3)
n'-hydroxyl-2-(5-nitro-2
h-tetrazolium-2-yl) imines is for Acetyl Chloride 98Min.: the mol ratio of sodiumazide is 1:1 ~ 6.
Acid in step (4) is 37% hydrochloric acid.
Reaction times in step (4) is 2 ~ 12 hours; Temperature of reaction is 0 ~ 50 ℃.
2-(5-nitro-2 in above-mentioned steps (1)
h-tetrazolium-2-yl) acetonitrile preparation method is as follows:
The first step, under cryosel bath condition, by soluble in water to anhydrous cupric sulfate and Sodium Nitrite, and drips the sulfuric acid-aqueous solution of 5-amino tetrazole, after dripping completely, and room temperature reaction half an hour; Add sodium hydroxide to react half an hour under 70 ℃ of conditions; Add sulphur acid for adjusting pH to 2 ~ 4, be extracted with ethyl acetate, anhydrous magnesium sulfate drying, revolves and steams part ethyl acetate; Pass into ammonia filtration and obtain anhydrous 5-nitro tetrazolium ammonium salt
Second step, is dissolved in above-mentioned anhydrous 5-nitro tetrazolium ammonium salt and Sodium Bromide in DMF, slowly drips chloromethyl cyanide, under 90 ~ 95 ℃ of conditions, reacts four hours, removes by filter inorganic salt, and DMF solvent adds water, puts into refrigerator and leaves standstill, and filters and obtains 2-(5-nitro-2
h-tetrazolium-2-yl) acetonitrile.
Accompanying drawing explanation
Fig. 1 is 5-((5-of the present invention nitro-2
h-tetrazolium-2-yl) methyl)-1
hthe Fourier transform infrared spectroscopy figure of-tetrazolium-1-alcohol.
Fig. 2 is 5-((5-of the present invention nitro-2
h-tetrazolium-2-yl) methyl)-1
hthe hydrogen nuclear magnetic resonance spectrogram of-tetrazolium-1-alcohol.
Fig. 3 is 5-((5-of the present invention nitro-2
h-tetrazolium-2-yl) methyl)-1
hthe carbon-13 nmr spectra figure of-tetrazolium-1-alcohol.
Fig. 4 is 5-((5-of the present invention nitro-2
h-tetrazolium-2-yl) methyl)-1
hthe MS(ESI of-tetrazolium-1-alcohol) secondary level spectrogram.
Embodiment
the preparation of nitro tetrazolium ammonium salt
Copper sulfate 7.4 g and Sodium Nitrite 20.1 g join in the there-necked flask of 1 L and add in 100 mL water and dissolve, and under cryosel bath condition, are cooled to 0-5 ℃.Simultaneously 5-amino tetrazole 8.6 g add a small amount of copper sulfate and join and in 140 mL water, add the 6.6 mL vitriol oils again and make 5-amino tetrazole entirely molten, slowly join in solution above 1 hour drip off by constant pressure funnel, stir at ambient temperature 10 min; Hydro-oxidation sodium 9 g are dissolved in the solution that is added drop-wise to stirring at room temperature after 100 mL water, drip complete post-heating to 70 ℃ reaction 1 hour; By diatomite filtration cupric oxide, washing filter cake, the filtrate obtaining adds sulfuric acid 6.4 mL; With ethyl acetate 6 × 80 mL extractions, each extraction all adds a small amount of acid; After anhydrous magnesium sulfate drying ethyl acetate solution, revolve and steam to 80 mL; Pass into ammonia two minutes, filter and obtain nitro tetrazolium ammonium salt 10 g, yield 76%.
Only directly be extracted with ethyl acetate and obtain nitro tetrazolium ammonium salt 3.2 g, yield 24% adding after sulfuric acid 6.4 mL in embodiment 1.
(5-nitro-2
h-tetrazolium-2-yl) preparation of acetonitrile
embodiment 3
Nitro tetrazolium ammonium salt 4.8 g and Sodium Bromide 3.9 g are dissolved in 100 mL DMF, chloromethyl cyanide 5 mL slowly drip, after dripping completely, being warming up to 90 ~ 95 ℃ stirs 4 hours, with Büchner funnel filtering inorganic salt, with several DMF filter wash cakes, filtrate adds 100 mL remaining mother liquor before, puts into refrigerator and leaves standstill a night, filter, filter cake obtains 2-(5-nitro-2 with dehydrated alcohol recrystallization
h-tetrazolium-2-yl) acetonitrile 4 g, yield 72%.
embodiment 4
Only the filtrate in embodiment 3 is added to 100 mL water, obtain 2-(5-nitro-2
h-tetrazolium-2-yl) acetonitrile 2.5 g, yield 45%.
n'-hydroxyl-2-(5-nitro-2
h-tetrazolium-2-yl) preparation of ethanamidine
embodiment 5
By above-mentioned 2-(5-nitro-2
h-tetrazolium-2-yl) acetonitrile 0.23 g, oxammonium hydrochloride 0.16 g, sodium bicarbonate 0.19 g adds in 20 mL methyl alcohol, is heated to 65 ℃ of reactions 2 hours; Remove by filter inorganic salt, vacuum is removed methyl alcohol and is obtained
n'-hydroxyl-2-(5-nitro-2
h-tetrazolium-2-yl) ethanamidine 0.24 g, productive rate 86%.
embodiment 6
Only change the reaction times in embodiment 5 into 0.5 hour, solvent makes water into and obtains
n'-hydroxyl-2-(5-nitro-2
h-tetrazolium-2-yl) ethanamidine 0.20 g, productive rate 72%.
embodiment 7
Only change the temperature of reaction in embodiment 5 into 20 ℃, solvent changes ethanol into and obtains
n'-hydroxyl-2-(5-nitro-2
h-tetrazolium-2-yl) ethanamidine 0.18 g, productive rate 65%.
embodiment 8
Only change the reaction times in embodiment 5 into 5 hours, 2-(5-nitro-2
h-tetrazolium-2-yl) acetonitrile 0.23 g, oxammonium hydrochloride 0.41 g, sodium bicarbonate 0.5 g, obtains
n'-hydroxyl-2-(5-nitro-2
h-tetrazolium-2-yl) ethanamidine 0.24 g, productive rate 86%.
embodiment 9
Only by 2-(5-nitro-2 in embodiment 5
h-tetrazolium-2-yl) acetonitrile 0.23 g, oxammonium hydrochloride 0.11 g, sodium bicarbonate 0.13 g, obtains
n'-hydroxyl-2-(5-nitro-2
h-tetrazolium-2-yl) ethanamidine 0.1 g, productive rate 36%.
n'-hydroxyl-2-(5-nitro-2
h-tetrazolium-2-yl) imines is for the preparation of Acetyl Chloride 98Min.
Will
n'-hydroxyl-2-(5-nitro-2
h-tetrazolium-2-yl) ethanamidine 0.19 g is dissolved in 37% hydrochloric acid soln 3 mL under the condition of 0 ~ 5 ℃, drips the aqueous solution of Sodium Nitrite 0.14 g, press
n'-hydroxyl-2-(5-nitro-2
h-tetrazolium-2-yl) ethanamidine: hydrochloric acid: the mol ratio of Sodium Nitrite is that 1:3:2 drips, and drips completely and reacts 2 hours under 75 ℃ of conditions afterwards; Be extracted with ethyl acetate, with anhydrous magnesium sulfate drying, vacuum-drying obtains
n'-hydroxyl-2-(5-nitro-2
h-tetrazolium-2-yl) imines is for Acetyl Chloride 98Min. 0.16 g, productive rate 80%.
embodiment 11
Only change the reaction times in embodiment 10 into 6 hours, temperature of reaction changes 30 ℃ into and obtains
n'-hydroxyl-2-(5-nitro-2
h-tetrazolium-2-yl) imines is for Acetyl Chloride 98Min. 0.1 g, productive rate 48%.
Only change the temperature of reaction in embodiment 10 into 75 ℃,
n'-hydroxyl-2-(5-nitro-2
h-tetrazolium-2-yl) ethanamidine: hydrochloric acid: the mol ratio 1:2:1 of Sodium Nitrite, obtains
n'-hydroxyl-2-(5-nitro-2
h-tetrazolium-2-yl) imines is for Acetyl Chloride 98Min. 0.11 g, productive rate 53%.
embodiment 13
Only by embodiment 10
n'-hydroxyl-2-(5-nitro-2
h-tetrazolium-2-yl) ethanamidine: hydrochloric acid: the mol ratio 1:1:1 of Sodium Nitrite, obtains
n'-hydroxyl-2-(5-nitro-2
h-tetrazolium-2-yl) imines is for Acetyl Chloride 98Min. 0.09 g, productive rate 44%.
n'-hydroxyl-2-(5-nitro-2
h-tetrazolium-2-yl) imines is for the preparation of acetyl nitrine
embodiment 14
Will
n'-hydroxyl-2-(5-nitro-2
h-tetrazolium-2-yl) imines is for Acetyl Chloride 98Min. 0.21 g: sodiumazide 0.33 1:6 in molar ratio, add in the mixed solution of acetone and water 20 mL, heat 60 ℃ of reactions 12 hours; With ethyl acetate 5 × 30 mL extractions, with anhydrous magnesium sulfate drying, revolve vacuum-drying and obtain
n'-hydroxyl-2-(5-nitro-2
h-tetrazolium-2-yl) imines is for acetyl nitrine 0.16 g, productive rate 74%.
embodiment 15
Only change the temperature of reaction in embodiment 14 into 20 ℃, the mixed solvent that solvent changes DMF and water into obtains
n'-hydroxyl-2-(5-nitro-2
h-tetrazolium-2-yl) imines is for acetyl nitrine 0.16 g, productive rate 74%.
embodiment 16
Only change the reaction times in embodiment 14 into 1 hour, temperature changes 60 ℃ into and obtains
n'-hydroxyl-2-(5-nitro-2
h-tetrazolium-2-yl) imines is for acetyl nitrine 0.08 g, productive rate 39%.
embodiment 17
Only by embodiment 14
n'-hydroxyl-2-(5-nitro-2
h-tetrazolium-2-yl) imines changes 1:1 into for Acetyl Chloride 98Min. and sodiumazide mol ratio,
n'-hydroxyl-2-(5-nitro-2
h-tetrazolium-2-yl) imines is for acetyl nitrine 0.07 g, productive rate 33%.
5-((5-nitro-2
h-tetrazolium-2-yl) methyl)-1
hthe preparation of-tetrazolium-1-alcohol
embodiment 18
n'-hydroxyl-2-(5-nitro-2
h-tetrazolium-2-yl) imines is dissolved in 37% hydrochloric acid 10 mL 10 ℃ of reactions 12 hours for acetyl nitrine 0.21 g; Ethyl acetate extraction 5 × 20 mL, anhydrous magnesium sulfate drying, vacuum-drying obtains 5-((5-nitro-2
h-tetrazolium-2-yl) methyl)-1
h-tetrazolium-1-alcohol 0.17 g, productive rate 80%.
1H?NMR?(DMSO，500?MHz)?
δ:?5.94?(m，2H)；
13C?NMR?(DMSO，125?MHz)
δ:?167.03，166.49，55.09；?MS?(ESI)?m/z:?211.92?(M-H)。
embodiment 19
Only change the reaction times in embodiment 18 into 2 hours, temperature of reaction changes 0 ℃ into and obtains 5-((5-nitro-2
h-tetrazolium-2-yl) methyl)-1
h-tetrazolium-1-alcohol 0.14 g, productive rate 66%.
Only change the temperature of reaction of embodiment 18 into 50 ℃, the reaction times changes 12 hours into and obtains 5-((5-nitro-2
h-tetrazolium-2-yl) methyl)-1
h-tetrazolium-1-alcohol 0.03 g, productive rate 14%.
This compound has tetrazolium structure, and nitrogen content is up to 59%, and Theoretical Calculation explosion velocity has reached 9122 ms
-1density is 1.88 gcm
-1, have potential application in high energy energetic material field.
Claims (10)
1.5-((5-nitro-2
h-tetrazolium-2-yl) methyl)-1
h-tetrazolium-1-alcohol, is characterized in that: have following structural formula:
2. 5-((5-according to claim 1 nitro-2
h-tetrazolium-2-yl) methyl)-1
hthe preparation method of-tetrazolium-1-alcohol, is characterized in that: said method comprising the steps of:
(1) by 2-(5-nitro-2
h-tetrazolium-2-yl) acetonitrile, oxammonium hydrochloride, sodium bicarbonate add in solvent, and reacting by heating, removes by filter inorganic salt, and solvent removed in vacuo obtains
n'-hydroxyl-2-(5-nitro-2
h-tetrazolium-2-yl) ethanamidine;
(2) by above-mentioned
n'-hydroxyl-2-(5-nitro-2
h-tetrazolium-2-yl) ethanamidine is dissolved in hydrochloric acid soln under certain conditions, drips sodium nitrite in aqueous solution, reacts under heating condition after dripping completely, and after reaction finishes, through extraction, dry dewatering, vacuum-drying obtains
n'-hydroxyl-2-(5-nitro-2
h-tetrazolium-2-yl) imines is for Acetyl Chloride 98Min.;
(3) by above-mentioned
n'-hydroxyl-2-(5-nitro-2
h-tetrazolium-2-yl) imines adds in solvent for Acetyl Chloride 98Min., sodiumazide, under heating condition, reacts, and after reaction finishes, through extraction, dry dewatering, vacuum-drying obtains
n'-hydroxyl-2-(5-nitro-2
h-tetrazolium-2-yl) imines is for acetyl nitrine;
(4) by above-mentioned
n'-hydroxyl-2-(5-nitro-2
h-tetrazolium-2-yl) imines is dissolved in acid and reacts for acetyl nitrine, and after reaction finishes, through extraction, dry dewatering, vacuum-drying obtains 5-((5-nitro-2
h-tetrazolium-2-yl) methyl)-1
h-tetrazolium-1-alcohol.
3. 5-((5-nitro-2 according to claim 2
h-tetrazolium-2-yl) methyl)-1
hthe preparation method of-tetrazolium-1-alcohol, is characterized in that the solvent described in step (1) selects methyl alcohol, ethanol, water or acetone; Temperature of reaction is 20 ~ 65 ℃, and the reaction times is 0.5 ~ 5 hour.
4. 5-((5-nitro-2 according to claim 2
h-tetrazolium-2-yl) methyl)-1
hthe preparation method of-tetrazolium-1-alcohol, is characterized in that 2-(5-nitro-2 in step (1)
h-tetrazolium-2-yl) mol ratio of acetonitrile and oxammonium hydrochloride is 1:1 ~ 4; 2-(5-nitro-2
h-tetrazolium-2-yl) mol ratio of acetonitrile and sodium bicarbonate is 1:1 ~ 4.
5. 5-((5-nitro-2 according to claim 2
h-tetrazolium-2-yl) methyl)-1
hthe preparation method of-tetrazolium-1-alcohol, is characterized in that in step (2), temperature of reaction is first 0 ~ 20 ℃, then is 30 ~ 75 ℃, the reaction times is 1 ~ 6 hour.
6. 5-((5-nitro-2 according to claim 2
h-tetrazolium-2-yl) methyl)-1
hthe preparation method of-tetrazolium-1-alcohol, is characterized in that in step (2)
n'-hydroxyl-2-(5-nitro-2
h-tetrazolium-2-yl) ethanamidine and hydrochloric acid 1:1 ~ 6;
n'-hydroxyl-2-(5-nitro-2
h-tetrazolium-2-yl) mol ratio of ethanamidine and Sodium Nitrite is 1:1 ~ 6.
7. 5-((5-nitro-2 according to claim 2
h-tetrazolium-2-yl) methyl)-1
hthe preparation method of-tetrazolium-1-alcohol, is characterized in that described in step (3), solvent is the mixed solvent of acetone, DMF, NMP and water, and the reaction times is 1 ~ 12 hour, and temperature of reaction is 20 ~ 60 ℃.
8. 5-((5-nitro-2 according to claim 2
h-tetrazolium-2-yl) methyl)-1
hthe preparation method of-tetrazolium-1-alcohol, is characterized in that in step (3)
n'-hydroxyl-2-(5-nitro-2
h-tetrazolium-2-yl) imines is for Acetyl Chloride 98Min.: the mol ratio of sodiumazide is 1:1 ~ 6.
9. 5-((5-nitro-2 according to claim 2
h-tetrazolium-2-yl) methyl)-1
hthe preparation method of-tetrazolium-1-alcohol, is characterized in that the acid in step (4) is 37% hydrochloric acid.
10. 5-((5-nitro-2 according to claim 2
h-tetrazolium-2-yl) methyl)-1
hthe preparation method of-tetrazolium-1-alcohol, is characterized in that the reaction times in step (4) is 2 ~ 12 hours; Temperature of reaction is 0 ~ 50 ℃.
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| CN111153864A (en) * | 2020-01-17 | 2020-05-15 | 西北大学 | Nitrogen-rich heat-resistant insensitive energetic compound and preparation method and application thereof |
| CN112010816A (en) * | 2020-09-11 | 2020-12-01 | 西北大学 | Methylene bridged nitrogen-rich heterocyclic compound and derivative and preparation method thereof |
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| US20100298384A1 (en) * | 2006-12-04 | 2010-11-25 | Mohamed Takhi | Novel oxazolidinone compounds as antiinfective agents |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN111153864A (en) * | 2020-01-17 | 2020-05-15 | 西北大学 | Nitrogen-rich heat-resistant insensitive energetic compound and preparation method and application thereof |
| CN111153864B (en) * | 2020-01-17 | 2021-06-29 | 西北大学 | Nitrogen-rich heat-resistant insensitive energetic compound and preparation method and application thereof |
| CN112010816A (en) * | 2020-09-11 | 2020-12-01 | 西北大学 | Methylene bridged nitrogen-rich heterocyclic compound and derivative and preparation method thereof |
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Application publication date: 20140514 |