GB2355714A - Ammonium 3,5-diaminopicrate - Google Patents
Ammonium 3,5-diaminopicrate Download PDFInfo
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- GB2355714A GB2355714A GB9925151A GB9925151A GB2355714A GB 2355714 A GB2355714 A GB 2355714A GB 9925151 A GB9925151 A GB 9925151A GB 9925151 A GB9925151 A GB 9925151A GB 2355714 A GB2355714 A GB 2355714A
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- trinitrobenzene
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- diaminopicrate
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/74—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
- C07C215/76—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton of the same non-condensed six-membered aromatic ring
- C07C215/80—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton of the same non-condensed six-membered aromatic ring containing at least two amino groups bound to the carbon skeleton
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- C—CHEMISTRY; METALLURGY
- C06—EXPLOSIVES; MATCHES
- C06B—EXPLOSIVES OR THERMIC COMPOSITIONS; MANUFACTURE THEREOF; USE OF SINGLE SUBSTANCES AS EXPLOSIVES
- C06B25/00—Compositions containing a nitrated organic compound
- C06B25/04—Compositions containing a nitrated organic compound the nitrated compound being an aromatic
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Abstract
Ammonium 3,5-diaminopicrate is prepared from 1,3,5-trialkoxy-2,4,6-trinitrobenzene by amination using ammonia gas at elevated temperature and pressure or liquid ammonia at room temperature and elevated pressure.
Description
1 2355714 AMMONIUM 3,5-DIAMINOPICRATE This invention relates to the
synthesis of a new compound, ammonium 3, 5 - diaminopi crate (ADAP) which may be used as an explosive.
There is a wide variety of explosive materials known in the art. Indeed there is a considerable body of literature on this subject and for a general review of the art the reader is referred to Urbanski, Chemistry and Technology of Explosives, Volumes 1-4, Pergamon Press.
Explosi-ves are highly energetic materials which on initiation release large amounts of heat and gas. It is the rapid gaseous expansion of the products of decomposition that is responsible for many of the explosive or propellant qualities of these materials.
In the art explosives are typically nitro-organic materials such as nitroaromatics, nitro-esters and nitro-amine compounds although recently new varieties of explosive have been developed that incorporate difluoramines.
A disadvantage of many of these modern explosives is that they are made from noxious or environmentally unsuitable reagents, often using harsh reaction conditions such as high temperatures. The current manufacturing route for the synthesis of 1,3,5-triamino-2,4,6-trinitrobenzene (TATB) uses oleum and sodium nitrite at high temperatures. Furthermore, the synthesis of TATB requires the use of halogenated precursors. There are environmental concerns that such precursors (and derivatives generated therefrom during synthesis) may cause environmental harm.
2 There is, therefore, a need to find new explosives or alternative routes to known explosives that can be manufactured through relatively inexpensive and environmentally friendly means.
Accordingly, there is provided a new compound - ammonium 3,5diaminopicrate (ADAP).
There is further provided a method for preparing ammonium 3,5diaminopicrate comprising the sequential steps of:
(i) deriving 1,3,5-trihydroxy-2,4,6-trinitrobenzene fr-om 1,3,5trihydroxybenzene precursor; (ii) deriving 1,3,5-trialkoxy-2,4,6-trinitrobenzene from 1,3,5-trihydroxy2,4,6-trinitrobenzene by alkylation; and (iii) deriving ammonium 3,5-diaminopicrate from 1,3,5-trialkoxy-2,4,6- trinitrobenzene by amination.
The step (i) of deriving 1,3,5-trihydroxy-2,4,6trinitrobenzene from 1,3,5trihydroxybenzene precursor can comprise the nitration of 1,3,5trihydroxybenzene.
Alternatively, this step can comprise the sequential steps:
(a) acetylation of 1,3,5-trihydroxybenzene to form 1,3,5triacetoxybenzene; and (b) nitration of 1,3,5-triacetoxybenzene to form 1,3,5trihydroxy-2,4,6- trinitrobenzene.
Suitable nitrating reagents would be sodium nitrite in conjunction with nitric acid. Alternatively, dinitrogen pentoxide in sulphuric acid can be used. A mixture of sulphuric and nitric acids would be a suitable alternative nitration agent.
3 A suitable acetylating reagent would be sodium acetate in acetic anhydride.
A suitable alkylating reagent for step (ii) would be potassium carbonate in dimethyl sulphate or in an alternative embodiment trimethyl orthoformate. In a preferred embodiment triethyl orthoformate is used.
A suitable amination for step (iii) comprises the use of ammonia gas introduced at elevated pressure 8-9 bar and at elevated temperature (130 OC - 170 OC).
In another embodiment, the amination comprises the following sequential steps:
(i) the use of a base at elevated temperature; (ii) the use of liquid ammonia at room temperature and elevated pressure; and (iii)purification using acid and subsequently ammonia.
An advantage of the current invention is that it provides a novel alternative explosive for the market.
Another advantage of the current invention is that it provides an explosive material of sufficient stability for a variety of practical purposes.
ADAP is soluble in water, an environmentally-friendly solvent. A high solubility in water ensures that the explosive is convenient to process and should facilitate easy demilitarisation of unwanted ordnance.
Yet another advantage of the current invention is that it provides an environmentally friendly method of fabrication that employs relatively mild reaction conditions..
4 Embodiments of the invention will now be described by way of the following examples and with reference to the accompanying drawing in which:
Figure 1 illustrates a first synthetic route to the new explosive ADAP; and Figure 2 illustrates an alternative synthetic route to ADAP.
The new compound ammonium 3,5-diaminopicrate (ADAP)_ The chemical structure of the ammonium 3,5-diaminopicrate was confirmed through FTIR, NMR and elemental analysis.
Use of ammonium 3,5-diaminopicrate as a new explosive The new explosive was found to have a sensitivity value that is applicable for practical commercial purposes. To this effect, using the Rotter Impact Test (RIT), the new explosive was found to have a figure of insensitiveness of 90. This can be compared with a value of 80 for RDX.
Preparation of ammonium 3,5-diaminopicrate (ADAP) from 1,3,5trihydroxybenzene (A) Step (i), the preparation of 1,3,5-trihydrox_V-2,4,6trinitrobenzene from 1,3,5-trih_ydroxybenzene.
A.1 Step (i) can be achieved by nitration of 1,3,5trihydroxybenzene. Two examples are given in A. 1. (i) and (ii) below.
A. 1 1,3,5-trihydroxybenzene (16.2 g, 0.1 mol) was added to a solution of sodium hydroxide (8.0 g, 0.2 mol) and sodium nitrite (27.6 g, 0.4 mol) in water (75 ml) at 30 OC. The resultant solution was added dropwise to a mixture of ice (108 g) and 99 % nitric acid (21 ml, 0.48 mmol), whilst maintaining the temperature below 5 1C. After stirring for 20 min at 15 OC, this suspension was added slowly to 65 % nitric acid (100 ml) at 50 OC. The mixture was stirred at 50 OC for 45 min, cooled and the solid then filtered off. It was washed with 3M hydrochloric acid (60 ml) and dried to give 1,3,5-trihydroxy-2,4,6-trinitrobenzene mono-hydrate (19.5 (f, 70 %), m.p. 168 OC, with loss of water at 138 OC (7.01 wt %; calculated for the mono-hydrate 6.45 wt This was identified by IR and NMR spectral analysis.
A.1.(ii) A solution of dinitrogen pentoxide (13.0 g, 120 mmol) in 98 % sulphuric acid (86 ml) was slowly added to a solution of anhydrous 1,3,5trihydroxybenzene (5.0 g, 40 mmol) in 98 % sulphuric acid (40 ml), whilst maintaining the temperature below -8 1C. The resultant solution was stirred for 4 h at -8 to 10 1C. During this period a yellow precipitate separated. This was filtered off, washed with cold 3M hydrochloric acid (50 ml) and dried to give 1,3,5trihydroxy-2,4,6-trinitrobenzene (8.84 g, 83 %), m.p. 166 1C, with loss of water at 130 OC (6.67 wt %) This was identified by FTIR and NMR spectral analysis.
A.2 Step (i) can also be achieved by acetylation of 1,3, 5trihydroxybenzene and subsequent nitration of 1,3,5triacetoxybenzene Acetylation can be performed as shown in example A.2. (i) below.
6 A. 2. (i) Sodium acetate (1.0 g, 12 mmol) was added to anhydrous 1,3,5trihydroxybenzene (1.0 g, 7.9 mmol) in acetic anhydride (6 ml). The resultant mixture was stirred at 1300C for 2 h, after which period it was cooled and poured into ice-water (33 g). The resultant precipitate was filtered off, was washed with water and dried to give 1,3,5-triacetoxybenzene (1.89 g, 95 %), m.p.105 IC. This was identified by FTIR and NMR spectral analysis. The 1,3,5- triacetoxybenzene can then be nitrated as described in the following examples A.2.(ii).(a) and A.2.(ii).(b) below. Note that the nitration process effectively nitrates the 2,4 and 6 positions and deacetylates the 1,3 and 5 positions of the 1,3,5triacetoxybenzene to give 1,3,5- trihydroxy-2,4,6trinitrobenzene. A. 2. (i i). (a) A solution of dinitrogen pentoxide (3.28 g, 30 mmol) in 98 % sulphuric acid (34 ml) was slowly added to 1,3,5triacetoxybenzene (2.21 g, 8.8 mmol) in 98% sulphuric acid (5ml), whilst maintaining the temperature below -5 OC. The resultant solution was stirred at -10 OC to 10 OC for 4 h. The yellow solid that separated was extracted into dichloromethane (500 ml) and treated with methanol (100 ml). The solvents were evaporated to give 1,3,5-trihydroxy2,4,6-trinitrobenzene (2.24 g, 98 %), m.p. 169 IC. This was identified by FTIR and NMR spectral analysis.
A. 2. (i i). (b) A solution of 1,3,5-triacetoxybenzene (20g, 79mmol)in 98% sulphuric acid (50ml) was slowly added to 99% nitric acid (13.5ml, 325mmol) in 98% sulphuric acid (100ml), whilst 7 maintaining the temperature below -100C. The resultant solution was stirred for 4 hours at -8 to 10'C ' during which time a yellow precipitate had formed. The solid was filtered off, was washed with cold 3M hydrochloric acid (50ml) and dried to give 1,3,5-trihydroxy-2,4, 6trinitrobenzene (21.4g, 97%), m.p. 164'C.
(B) Step (ii) involving the preparation of 1,3,5-trialkoxy 2,4,6-trinitrobenzene from 1,3,5-trihydroxy-2,4,6- trinitrobenzene.
Examples B.1.(i) and B.1.(ii) show how the methoxy derivative can be synthesised. B.2.(i) shows how the ethoxy derivative can be formed.
B.1.(i) 1,3,5-trihydroxy-2,4,6-trinitrobenzene (5.0 g, 19.2 mmol) and potassium carbonate (12.5 g, 90.6 mmol) in dimethyl sulphate (100 ml, 1.06 mol) was heated at 125 IC for 4 h. The resultant solution was poured into cold water (100 ml), the mixture was basified with 30 % sodium hydroxide solution and then heated to almost boiling. on cooling, a solid separated and was filtered off and dried. Extraction of the solid with acetone (150 ml) and concentration of the extract gave 1,3,5-trimethoxy-2,4,6trinitrobenzene (2.0 g, 34 %), m.p. 73-74 IC. This was identified by FTIR and NMR spectral analysis.
B.1.(ii) 1,3,5-trihydroxy-2,4,6-trinitrobenzene (5.22 g, 20 mmol) in trimethyl orthoformate (30 ml) was heated at 95-100 IC for 4 h. A mixture of methanol and methyl formate distilled off, b.p. 65-78 OC. The temperature was then raised to 105-110 OC for a further 0.5 h, and more distillate was collected, b.p. 92-98 OC. The solution was then 8 concentrated at lower temperature to give 1,3,5-trimethoxy2,4,6trinitrobenzene (5.99 g, 99 %), m.p. 740C. This was identified by FTIR and NMR spectral analysis.
B.2.(i) 1,3,5-trihydroxy-2,4,6-trinitrobenzene (11.1 g, 39.8 Mmol) in triethyl orthoformate (100 ml) was heated at 100 OC for 1.25 h. A mixture of ethanol and ethyl formate distilled off, b.p. 70-75 1C. The temperature was then raised to 120-125 OC for lh and 140-145 OC for 0.5 h, and more distillate was collected, b.p. 65-75 1C. The solution was then concentrated at a lower temperature to give a beige solid T13.9 g) which was recrystallised from ethanol (50 ml) to give 1,3,5-triethoxy-2,4,6trinitrobenzene (12.4 g, 90 %), m.P. 117 1C. This was identified by FTIR and NMR spectral analysis.
(C) Step (iii) involving the preparation of ammonium 3,5diaminopicrate (ADAP) from 1,3,5-trimethoxy-2,4,6trinitrobenzene.
Examples C.1.(i)-C.1.(iv) illustrate how ADAP can be synthesised from 1,3, 5-methoxy-2,4,6-trinitrobenzene. It is anticipated that ADAP can be synthesised from other 1,3,5alkoxy-2,4,6-nitrobenzenes using this method.
C.1.(i) A solution of 1,3,5-trimethoxy-2,4,6-trinitrobenzene (2.5 g) in toluene (50 ml) was sealed in an autoclave at room temperature. The temperature was raised to 150 OC, and ammonia gas was introduced at a pressure of 8-9 bar for 4 h. The product was filtered off, was washed with toluene (25 ml) and dried to give a mixture of TATB and ammonium 3,5diaminopicrate (ADAP). This was mixed with water (100 9 ml) and heated to boiling point. The undissolved solid was filtered off and washed to give TATB (0.71 g, 33 %). The filtrate was concentrated to give ammonium 3,5diaminopicrate mono-hydrate (1.57 g, 65 %). This was purified by recrystallisation from water (100 ml) to give the mono- hydrate (1.10 g).
DSC analysis (10 K/min) exhibited an endotherm at 104 OC, and an exotherm at 278 OC.
FTIR (KBr disc) 3243, 1589, 1559, 1431, 1222, 1165, 925, 798 and 686cm-1. 1H NMR (DMSO-d6) 7.1 (4H, t, J=52Hz, NH4+) and 9.a4ppm (4H, S, NH'). 13C NMR (DMSO-d6) 110, 123, 150 and 166ppm.
C.I.(ii) A solution of 1,3,5-trimethoxy-2,4,6-trinitrobenzene (2.0 g) in toluene (50 ml) was sealed in an autoclave at room temperature. The temperature was raised to 170 OC, and ammonia gas was introduced at a pressure of 8-9 bar for 4 h. The product was filtered off, was washed with toluene (25 ml) and dried to give a mixture of 1,3,5-triamino2,4,6-trinitrobenzene (TATB) and ammonium 3,5diaminopicrate. This was mixed with water (100 ml) and heated to boiling point. The undissolved solid was filtered off, washed and dried to give TATB (0.59g, 35%). The filtrate was concentrated to give ammonium 3,5diaminopicrate(l.24 g, 64 %) This was confirmed by FTIR and HPLC analysis.
C.1.(iii) A solution of 1,3,5-trimethoxy-2,4,6-trinitrobenzene (2.0 g) in toluene (50 ml) was sealed in an autoclave at room temperature. The temperature was raised to 135 IC, and ammonia gas was introduced at a pressure of 8-9 bar for 4 h. The product was filtered off, was washed with toluene (25 ml) and dried to give a mixture of TATB and ammonium 3,5-diaminopicrate. This was mixed with water (100 ml) and heated to boiling point. The undissolved solid was filtered off, washed and dried to give TATB (1-00g, 59%). The filtrate was concentrated to give ammonium 3,5diaminopi crate (0. 8 g, 41 %). This was confirmed by FTIR and HPLC.
C.l.(iv) Sodium hydroxide (0.66 g, 16.5 mmol) was added to 1,3,5trimethoxy-2,4,6- trinitrobenzene (5.0 g, 16.5 mmol) in methanc-i (100 ml) and the mixture was heated at 60 IC for 24 h. The solvent was evaporated and the residue was washed with diethyl ether (30 ml) and dried. Dried liquid ammonia (50 ml) was added to the residue in an autoclave, the vessel was sealed and the temperature was allowed to rise to room temperature (8-9 bar). After 24 h, the ammonia was allowed to evaporate whilst toluene (50 ml) was added. The resultant orange solid was filtered off, was washed with toluene (25 ml) and dried.
This solid was added to 3 M hydrochloric acid (500 ml) and the mixture was stirred for 24 h. The solid was again filtered off, was washed with water until the washings were no longer acidic and then dried. Liquid ammonia (25 ml) was added to the solid in an autoclave, the vessel was sealed and left at room temperature for 0.5 h. Toluene (50 ml) was added and the ammonia was allowed to evaporate. The yellow solid was filtered off, was washed with toluene (20 ml) and then dried to give pure ammonium 3,5-diaminopicrate (4.23 g, 93 %). This was confirmed by FTIR analysis.
DSC analysis exhibited a single exotherm at 275 OC. Elemental analysis found a composition of C 26.63, H 2.69, I I N 29.84% by weight. These ratios compare with theoretical values of C26. 10, H 2.92, N 30.43% for ADAP. Such a close agreement indicates that the isolated product is ADAP.
12
Claims (16)
1. A compound ammonium 3,5-diaminopicrate.
2. The use of ammonium 3,5-diaminopicrate as an explosive.
3. A method for preparing ammonium 3,5-diaminopicrate comprising the sequential steps of:
(i) deriving 1,3,5-trihydroxy-2,4,6-trinitrobenzene from 1,3,5trihydroxybenzene precursor; (ii) deriving 1,3,5-trialkoxy-2,4,6-trinitrobenzene from 1,3,5-trihydroxy2,4,6-trinitrobenzene by alkylation; and (iii) deriving ammonium 3,5-diaminopicrate from 1,3,5-trialkoxy-2,4,6- trinitrobenzene by amination.
4. The method as described in claim 3 wherein the step (i) comprises the nitration of 1,3,5-trihydroxybenzene.
5. The method as described in claim 3 wherein the step W comprises the sequential steps:
(a) acetylation of 1,3,5-trihydroxybenzene to form 1,3,5triacetoxybenzene; and (b) nitration of 1,3,5-triacetoxybenzene to form 1,3,5trihydroxy-2,4,6- trinitrobenzene.
6. The method as described in claim 5 wherein the acetylation comprises the use of sodium acetate in acetic anhydride.
7. The method as described in any one of claims 4 to 6 wherein the nitration comprises the use of dinitrogen pentoxide in sulphuric acid.
13
8. The method as described in any one of claims 4 to 6 wherein the nitration comprises the use of sodium nitrite with nitric acid.
9. The method as described in any one of claims 4 to 6 wherein the nitration comprises the use of a mixture of sulphuric acid and nitric acid.
10. The method as described in any one of claims 3 to 9 wherein the alkylation comprises the use of trialkyl orthoformate.
11. The-method as described in claim 10 wherein the alkylation comprises the use of one of trimethyl, triethyl or tripropyl orthoformate.
12. The method as described in any one of claims 3 to 9 wherein the alkylation comprises the use of potassium carbonate in dimethyl sulphate.
13. The method as described in any one of claims 3 to 12 wherein the amination comprises the use of ammonia gas introduced at elevated pressure 8-9 bar and at elevated temperature (1300C - 170'C).
14. The method as described in any one of claims 3 to 12 wherein the amination comprises the following sequential steps:
(i) the use of base at elevated temperature; (ii) the use of liquid ammonia at room temperature and elevated pressure; and (iii)purification using acid and subsequently ammonia.
14
15. A method for preparing ammonium 3,5-diaminopicrate as substantially as herein before described with reference to figure 1.
16. A method for preparing ammonium 3, 5 - diaminopi crate as substantially as herein before described with reference to figure 2.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB9925151A GB2355714B (en) | 1999-10-26 | 1999-10-26 | Ammonium 3,5-diaminopicrate |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB9925151A GB2355714B (en) | 1999-10-26 | 1999-10-26 | Ammonium 3,5-diaminopicrate |
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| Publication Number | Publication Date |
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| GB9925151D0 GB9925151D0 (en) | 2000-05-03 |
| GB2355714A true GB2355714A (en) | 2001-05-02 |
| GB2355714B GB2355714B (en) | 2004-03-17 |
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7737308B1 (en) | 2009-06-15 | 2010-06-15 | Alliant Techsystems Inc. | Methods for nitrating compounds |
| US7910776B2 (en) | 2009-06-15 | 2011-03-22 | Alliant Techsystems Inc. | Methods of producing 1,3,5-triamino-2,4,6-trinitrobenzene |
| US8030521B2 (en) | 2007-05-07 | 2011-10-04 | Alliant Techsystems Inc. | Methods of producing 1,3,5-triamino-2,4,6-trinitrobenzene |
| CN104926660A (en) * | 2015-05-29 | 2015-09-23 | 中国科学院青岛生物能源与过程研究所 | Green synthetic method of trinitrophloroglucinol and application thereof |
| CN104987293A (en) * | 2015-07-22 | 2015-10-21 | 中国科学院青岛生物能源与过程研究所 | Green nitrification method and application for phenolic compound |
| CN107778184A (en) * | 2017-11-08 | 2018-03-09 | 中国工程物理研究院化工材料研究所 | It is a kind of to synthesize the method without chlorine photoacoustic spectroscopy with microchannel reaction technology |
| CN109485571A (en) * | 2018-11-02 | 2019-03-19 | 南京理工大学 | The method of etherificate synthesis TORTNB in microreactor |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7763753B1 (en) * | 2009-06-15 | 2010-07-27 | Alliant Techsystems Inc. | Methods for the production of 1,3,5-triamino-2,4,6-trinitrobenzene |
| CN114605273B (en) * | 2022-03-29 | 2023-06-02 | 南昌航空大学 | Method for synthesizing arylaminophenol compound by palladium-catalyzed CO-participated 1, 4-eneyne aromatization reaction |
-
1999
- 1999-10-26 GB GB9925151A patent/GB2355714B/en not_active Expired - Fee Related
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8030521B2 (en) | 2007-05-07 | 2011-10-04 | Alliant Techsystems Inc. | Methods of producing 1,3,5-triamino-2,4,6-trinitrobenzene |
| US7737308B1 (en) | 2009-06-15 | 2010-06-15 | Alliant Techsystems Inc. | Methods for nitrating compounds |
| US7910776B2 (en) | 2009-06-15 | 2011-03-22 | Alliant Techsystems Inc. | Methods of producing 1,3,5-triamino-2,4,6-trinitrobenzene |
| CN104926660A (en) * | 2015-05-29 | 2015-09-23 | 中国科学院青岛生物能源与过程研究所 | Green synthetic method of trinitrophloroglucinol and application thereof |
| CN104987293A (en) * | 2015-07-22 | 2015-10-21 | 中国科学院青岛生物能源与过程研究所 | Green nitrification method and application for phenolic compound |
| CN104987293B (en) * | 2015-07-22 | 2017-05-31 | 中国科学院青岛生物能源与过程研究所 | A kind of green nitration method of phenolic compound and application |
| CN107778184A (en) * | 2017-11-08 | 2018-03-09 | 中国工程物理研究院化工材料研究所 | It is a kind of to synthesize the method without chlorine photoacoustic spectroscopy with microchannel reaction technology |
| CN109485571A (en) * | 2018-11-02 | 2019-03-19 | 南京理工大学 | The method of etherificate synthesis TORTNB in microreactor |
| CN109485571B (en) * | 2018-11-02 | 2021-09-10 | 南京理工大学 | Method for synthesizing TORTNB by etherification in microreactor |
Also Published As
| Publication number | Publication date |
|---|---|
| GB9925151D0 (en) | 2000-05-03 |
| GB2355714B (en) | 2004-03-17 |
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