CN105777587B - N- nitro Trinitroethyls carbamate ion salt containing energy, preparation method and application - Google Patents

N- nitro Trinitroethyls carbamate ion salt containing energy, preparation method and application Download PDF

Info

Publication number
CN105777587B
CN105777587B CN201610164724.9A CN201610164724A CN105777587B CN 105777587 B CN105777587 B CN 105777587B CN 201610164724 A CN201610164724 A CN 201610164724A CN 105777587 B CN105777587 B CN 105777587B
Authority
CN
China
Prior art keywords
nitro
carbamate
carbonate
trinitroethyl
ion salt
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.)
Expired - Fee Related
Application number
CN201610164724.9A
Other languages
Chinese (zh)
Other versions
CN105777587A (en
Inventor
杨军
李营
黄海丰
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Shanghai Institute of Organic Chemistry of CAS
Original Assignee
Shanghai Institute of Organic Chemistry of CAS
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Shanghai Institute of Organic Chemistry of CAS filed Critical Shanghai Institute of Organic Chemistry of CAS
Priority to CN201610164724.9A priority Critical patent/CN105777587B/en
Publication of CN105777587A publication Critical patent/CN105777587A/en
Application granted granted Critical
Publication of CN105777587B publication Critical patent/CN105777587B/en
Expired - Fee Related legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C271/06—Esters of carbamic acids
    • C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C279/00—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
    • C07C279/02—Guanidine; Salts, complexes or addition compounds thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C279/00—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
    • C07C279/20—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups containing any of the groups, X being a hetero atom, Y being any atom, e.g. acylguanidines
    • C07C279/24—Y being a hetero atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C281/00—Derivatives of carbonic acid containing functional groups covered by groups C07C269/00 - C07C279/00 in which at least one nitrogen atom of these functional groups is further bound to another nitrogen atom not being part of a nitro or nitroso group
    • C07C281/16—Compounds containing any of the groups, e.g. aminoguanidine
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/04—1,2,3-Triazoles; Hydrogenated 1,2,3-triazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D249/14—Nitrogen atoms
    • 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
    • C07D257/04—Five-membered rings
    • C07D257/06—Five-membered rings with nitrogen atoms directly attached to the ring carbon atom

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The N nitro Trinitroethyls carbamate of present invention ion salt containing energy, preparation method and applications.System dissolves N nitro Trinitroethyls carbamate in organic solvent and carbonate, bicarbonate or the amino azole compound of alkali react acquisition at room temperature.Involved N nitro Trinitroethyls carbamate ion salt containing energy is a kind of energy-containing compound, has the characteristics of high oxygen balance and high explosion velocity, is expected to be applied to explosive wastewater and solid propellant.

Description

N- nitro Trinitroethyls carbamate ion salt containing energy, preparation method and application
Technical field
The present invention relates to N- nitro Trinitroethyls carbamate ion salt containing energy, preparation method and application, belong to and contain It can field of material technology.
Background technology
Modern war requirement weaponry can realize long-range strike and efficiently injure, and propellant and explosive are proposed The demand of energetic, this just needs to realize energetic first as the energetic material of energy carrier.The ion salt containing energy has steam It forces down, the features such as sensitivity is low, is one of hot spot of current development energy-rich compound.Oxygen balance is the important ginseng of energy-containing compound It counts, the energy level of energy-containing compound can be effectively improved by improving oxygen balance in the case where oxygen balance is less than or equal to zero.But It is current containing can ion salt generally have the characteristics that oxygen balance is low, mainly using the azotic heterocyclic compound of negative oxygen balance as containing The anion of energy ion salt, relatively low so as to cause the ion salt oxygen balance containing energy is obtained, correspondingly, energy is relatively low.
N- nitro Trinitroethyl carbamates (NTNC) are by GermanyTeach a kind of oxygen balance of report For+14.9% Halogen oxidant, contain there are one acid value NH, so as to which the compound be made to show stronger acidity, therefore, N- Nitro Trinitroethyl carbamate can be as the anion of the ion salt containing energy.Acid compound is in use to bullet Body material has stronger corrosivity, and neutral energy-containing compound can be obtained by the modification of ion salt, during avoiding use Corrosion to airframe material.In addition, the oxygen balance due to N- nitro Trinitroethyl carbamates is high, by with rich nitrogen sun from The collocation of son can obtain the energy-rich compound balanced with higher oxygen.、
The present invention has designed and synthesized N- nitro Trinitroethyls carbamate ion salt containing energy, such energy-containing compound Have the characteristics of high energy, be expected to be applied to explosive wastewater and propellant.
Invention content
The object of the present invention is to provide N- nitro Trinitroethyls carbamate ion salt containing energy, preparation method and answer With.
The N- nitro Trinitroethyl carbamates of present invention ion salt containing energy is a kind of novel energy-rich compound, is had Have following structural formula：
The N- nitro Trinitroethyl carbamates of the present invention are realized by following route：
Its specific preparation process is as follows：
At room temperature, N- nitro Trinitroethyl carbamates are dissolved in organic solvent, added thereto under stirring Enter the carbonate, bicarbonate or amino azole compound of alkali, reaction 1-5 hours is stirred at room temperature；The N- nitro trinitro-s The molar ratio of the carbonate of ethyl carbamate and alkali, bicarbonate or amino azole compound is 1:0.5-1.0；Described The carbonate of alkali is ammonium carbonate, guanidine carbonate, an aminoguanidine carbonate, diaminoguanidine carbonate or triaminoguanidine carbonate；Institute The bicarbonate stated is guanidine bicarbonate, an aminoguanidin carbonate, diaminoguanidine bicarbonate or triaminoguanidine bicarbonate； The amino azole compound for 4- amino -1,2,4- triazoles, 3- amino -1,2,4- triazoles, 1,5- diamino-tetrazolium, 3, 4,5- triamido -1,2,4- triazoles, 3,5- diaminostilbenes, 2,4- triazoles or 1- amino -1,2,3- triazoles.
Filtering, organic solvent washing, the purification process that solvent or drying is evaporated off may be used in above-mentioned reaction product.
The present invention method described in organic solvent can be methanol, ethyl alcohol, dichloromethane, chloroform, acetonitrile or Ethyl acetate.
Not only method of the invention is simple, but also the characteristics of the compound of the present invention tool high energy, can be applied to energetic material, Such as explosive wastewater and propellant.
Specific embodiment
The preparation of embodiment 1N- nitro Trinitroethyl carbamate ammonium salts (1)
Its structural formula is as follows：
After 100.3mg N- nitro Trinitroethyl carbamates (0.37mmol) are dissolved in 2mL dichloromethane, stir It mixes down and adds in 17.9mg ammonium carbonates (0.18mmol) thereto, reaction 5 hours is stirred at room temperature, white solid is precipitated, filtering precipitates, And it is washed with dichloromethane, dry 107.9mg products.1H NMR([D6]DMSO,300MHz):δ=7.24 (s, 1H), 7.08 (s,1H),6.91(s,1H),5.58(s,2H)ppm；13C NMR([D6]DMSO,100MHz):δ=156.6,125.4, 60.6ppm.IR(KBr):3115.9,2360.2,2341.2,1720.7,1596.8,1424.6,1400.5,1304.9, 1230.0,1118.0,1093.7,787.4,667.9cm-1Elemental analysis Elemental analysis for C3H6N6O10 (286.01):Calculated value Calculated:C:12.59H:2.11N:29.37；Measured value Measured:C:12.05H:2.39N: 29.49.
The preparation of embodiment 2N- nitro Trinitroethyl carbamate guanidine salts (2)
After 134.5mg N- nitro Trinitroethyl carbamates (0.50mmol) are dissolved in 2mL dichloromethane, stir It mixes down and adds in 44.8mg guanidine carbonates (0.25mmol) thereto, reaction 3 hours is stirred at room temperature, white solid is precipitated, filtering is heavy It forms sediment, and is washed with dichloromethane, product is obtained with quantitative yield after drying.1H NMR([D6]DMSO,300MHz):δ=6.90 (s, 6H),5.58(s,2H)ppm；13C NMR([D6]DMSO,100MHz):δ=158.0,157.4,125.6,60.5ppm.IR (KBr):3445.9,3273.4,3206.8,3012.8,2951.4,1716.7,1662.7,1593.2,1432.2,1382.5, 1304.1,1222.5,1113.4,1036.6,967.0,885.5,856.1,811.9,784.0,539.6cm-1.Elemental analysis for C4H8N8O10(328.04):Calculated:C:14.64H:2.46N:34.15；Measured:C: 14.78H:2.65N:34.30.
The preparation of one aminoguanidinium salts (3) of embodiment 3N- nitro Trinitroethyls carbamate
Its structural formula is as follows：
After 301.2mg N- nitro Trinitroethyl carbamates (1.10mmol) are dissolved in 2mL methanol, under stirring 155.5mg guanidines bicarbonate (1.10mmol) is added in thereto, reaction 1 hour is stirred at room temperature, concentration removes solvent, with quantitative receipts Rate obtains 385.2mg products.1H NMR([D6]DMSO,300MHz):δ=8.56 (s, 2H), 7.26 (s, 2H), 6.73 (s, 2H), 5.59(s,2H),4.42(s,2H)ppm；13C NMR([D6]DMSO,100MHz):δ=158.80,156.76,125.60, 60.57ppm.IR(KBr):3507.96,3422.99,3392.06,3332.36,3241.02,2990.41,2952.48, 2894.16,2359.92,2340.02,2191.85,1686.94,1667.12,1581.04,1530.27,1418.50, 1384.86,1301.66,1231.97,1116.29,1089.29,959.40,855.38,822.03,786.10,739.89, 667.79,547.35,437.48cm-1.Elemental analysis for C4H9N9O10(343.05):Calculated:C: 14.00H:2.64N:36.73；Measured:C:14.11H:2.70N:36.68.
The preparation of embodiment 4N- nitro Trinitroethyl carbamate 4- amino -1,2,4- triazolium salts (4)
Its structural formula is as follows：
After 200.2mg N- nitro Trinitroethyl carbamates (0.75mmol) are dissolved in 2mL dichloromethane, stir It mixes down and adds in 62.5mg4- amino-1,2,4-triazoles (0.75mmol) thereto, reaction 2 hours is stirred at room temperature, it is solid that white is precipitated Body, filtering precipitation, and washed with dichloromethane, it is dry that 257.0mg products are obtained with quantitative yield.1H NMR([D6]DMSO, 300MHz):δ=9.27 (s, 2H), 8.64 (s, 2H), 5.70 (s, 2H) ppm；13C NMR([D6]DMSO,100MHz):δ= 154.33,144.08,125.11,60.79ppm.IR(KBr):3298.3,3112.1,3049.2,2961.3,1687.0, 1622.1,1592.5,1538.0,1462.4,1415.0,1392.8,1370.7,1354.5,1307.8,1265.1,1205.2, 1157.2,1106.8,1040.4,962.0,947.0,905.5,881.1,858.7,831.2,781.3,708.9,680.1, 651.9,622.8,541.6,489.8,472.9,424.3cm-1.Elemental analysis for C5H7N9O10 (353.03):Calculated:C:17.00H:2.00N:35.70；Measured:C:17.13H:2.10N:36.88.
The preparation of embodiment 5N- nitro Trinitroethyl carbamate 3- amino -1,2,4- triazolium salts (5)
Its structural formula is as follows：
After 200.2mg N- nitro Trinitroethyl carbamates (0.75mmol) are dissolved in 2mL dichloromethane, stir It mixes down and adds in 62.8mg3- amino-1,2,4-triazoles (0.75mmol) thereto, reaction 2 hours is stirred at room temperature, it is solid that white is precipitated Body, filtering precipitation, and washed with dichloromethane, it is dry that 255.7mg products are obtained with quantitative yield.1H NMR([D6]DMSO, 300MHz):δ=8.30 (s, 1H), 5.60 (s, 2H) ppm；13C NMR([D6]DMSO,100MHz):δ=156.09,150.75, 139.25,125.10,60.63ppm.IR(KBr):3391.8,3318.0,3264.4,3190.7,2999.7,2956.7, 2896.2,2727.7,2627.5,2568.2,1721.6,1696.1,1622.0,1593.8,1527.2,1499.0,1466.4, 1436.2,1382.5,1325.2,1305.4,1258.4,1229.9,1148.5,1121.4,1095.4,1056.0,1029.6, 986.4,943.9,888.4,864.5,856.4,813.9,790.1,781.3,764.4,747.1,730.7,673.9, 599.3,538.0,490.4,477.1,441.6,404.9cm-1.Elemental analysis for C5H7N9O10 (353.03):Calculated:C:17.00H:2.00N:35.70；Measured:C:17.39H:2.02N:37.39.
The performance of part of compounds is as shown in the table：
The ion salt performance parameter containing energy of table 1

Claims (5)

1. for N- nitro Trinitroethyls carbamate ion salt containing energy in energetic material field, with following knot Structure：
2. a kind of synthetic method of N- nitros Trinitroethyl carbamate according to claim 1 ion salt containing energy, It is characterized in that：In organic solvent and at room temperature, the carbonate of N- nitros Trinitroethyl carbamate and alkali, bicarbonate Salt or amino azole compound are reacted 1~5 hour；The N- nitro Trinitroethyl carbamates and the carbonate of alkali, The molar ratio of bicarbonate or amino azole compound is 1:0.5~1.0；The carbonate of the alkali is ammonium carbonate, guanidine carbonic acid Salt, an aminoguanidine carbonate or diaminoguanidine carbonate；
Wherein, bicarbonate is guanidine bicarbonate, an aminoguanidin carbonate or diaminoguanidine bicarbonate；And the ammonia Base azole compounds are 1,5- diamino-tetrazolium.
3. the synthetic method of N- nitros Trinitroethyl carbamate according to claim 2 ion salt containing energy, special Sign is：Product is by filtering, organic solvent washing, the purification process that solvent or drying is evaporated off.
4. the synthetic method of N- nitro Trinitroethyl carbamates ion salt containing energy according to Claims 2 or 3, It is characterized in that：Solvent is methanol, ethyl alcohol, dichloromethane, chloroform, acetonitrile or ethyl acetate.
5. a kind of N- nitros Trinitroethyl carbamate as described in claim 1 ion salt containing energy is used for energetic material.
CN201610164724.9A 2016-03-22 2016-03-22 N- nitro Trinitroethyls carbamate ion salt containing energy, preparation method and application Expired - Fee Related CN105777587B (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN201610164724.9A CN105777587B (en) 2016-03-22 2016-03-22 N- nitro Trinitroethyls carbamate ion salt containing energy, preparation method and application

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN201610164724.9A CN105777587B (en) 2016-03-22 2016-03-22 N- nitro Trinitroethyls carbamate ion salt containing energy, preparation method and application

Publications (2)

Publication Number Publication Date
CN105777587A CN105777587A (en) 2016-07-20
CN105777587B true CN105777587B (en) 2018-06-26

Family

ID=56390524

Family Applications (1)

Application Number Title Priority Date Filing Date
CN201610164724.9A Expired - Fee Related CN105777587B (en) 2016-03-22 2016-03-22 N- nitro Trinitroethyls carbamate ion salt containing energy, preparation method and application

Country Status (1)

Country Link
CN (1) CN105777587B (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN106349173B (en) * 2016-08-23 2018-08-14 中国工程物理研究院化工材料研究所 A kind of trinitro- methyl azole energy-containing compound and preparation method thereof

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7745635B1 (en) * 2003-06-16 2010-06-29 Drake Greg W Energetic ionic salts
CN103059009A (en) * 2013-01-24 2013-04-24 北京理工大学 4-nitro-3-(5-tetrazole) furoxan energetic ionic salt and preparation method thereof
CN103992227A (en) * 2014-05-16 2014-08-20 南京理工大学 Energetic salt based on 2, 4, 6-trinitro-1, 3-di(2', 4', 6'-trinitro-3'-hydroxyl styryl) benzene, synthetic method and application thereof
CN104557761A (en) * 2015-01-09 2015-04-29 西安近代化学研究所 3,3'-dinitramino-4,4'-azoxyfurazan energetic ion salt compound
CN104710363A (en) * 2015-04-09 2015-06-17 中国工程物理研究院化工材料研究所 Energetic compound 1-(2,2,2-trinitroethylamino)-3,5-dinitropyrazole and preparation method thereof

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7745635B1 (en) * 2003-06-16 2010-06-29 Drake Greg W Energetic ionic salts
CN103059009A (en) * 2013-01-24 2013-04-24 北京理工大学 4-nitro-3-(5-tetrazole) furoxan energetic ionic salt and preparation method thereof
CN103992227A (en) * 2014-05-16 2014-08-20 南京理工大学 Energetic salt based on 2, 4, 6-trinitro-1, 3-di(2', 4', 6'-trinitro-3'-hydroxyl styryl) benzene, synthetic method and application thereof
CN104557761A (en) * 2015-01-09 2015-04-29 西安近代化学研究所 3,3'-dinitramino-4,4'-azoxyfurazan energetic ion salt compound
CN104710363A (en) * 2015-04-09 2015-06-17 中国工程物理研究院化工材料研究所 Energetic compound 1-(2,2,2-trinitroethylamino)-3,5-dinitropyrazole and preparation method thereof

Non-Patent Citations (4)

* Cited by examiner, † Cited by third party
Title
"The Energetic Nitrocarbamate O2NN(H)CO[OCH 2C(NO2)3] Derived from Phosgene";Quirin J. Axthammer等;《Z. Anorg. Allg. Chem.》;20131017;第76-83页 *
"含能分子合成最新进展";田均均等;《含能材料》;20160104;第24卷(第1期);第2页第1段 *
"含能离子化合物的分子设计与性能研究进展";李娜等;《含能材料》;20100815;第18卷(第4期);第467-475页 *
"钝感高能含能离子盐的研究进展";梁丽轩等;《火炸药学报》;20140228;第37卷(第1期);第1-11页 *

Also Published As

Publication number Publication date
CN105777587A (en) 2016-07-20

Similar Documents

Publication Publication Date Title
CN103059009A (en) 4-nitro-3-(5-tetrazole) furoxan energetic ionic salt and preparation method thereof
CN105777587B (en) N- nitro Trinitroethyls carbamate ion salt containing energy, preparation method and application
CN116284189B (en) Method for synthesizing MANT-GTPγS
CN107488181B (en) 1,4- dinitro amido -3,6- binitropyrazole [4,3-c] and two diazanyl tetrazine salt compound of pyrazoles
CN104447762A (en) Energetic ionic salts of 7-nitryl-4-ketone-4,8-dihydro-[1,2,4] triazole [5,1-d] [1,2,3,5] tetrazine-2-oxide and preparation method of energetic ionic salt
CN102952124B (en) 3,4-double (1-hydrogen-5-tetrazole radical) furoxans are containing energy ion salt and preparation method thereof
CN103483330A (en) Energy containing ionic salts of 4, 4'-bi [3, 3'-(1-H-5-tetrazolium)] furazan and preparation method thereof
CN103524489B (en) The synthesis technique of 2 chlorine 5 ((base of 2 (Nitromethylene) imidazolidine 1) methyl) pyridines
CN110386938A (en) Trintriamine triazol triazole and its ion salt containing energy and preparation
US5256792A (en) Amine salts of nitroazoles
US7964626B2 (en) Process for producing N,N′-carbonyldiimidazole
CN106045981A (en) Preparation method for hectogram-scale energy-containing 4,5-di(tetrazolyl)triazole organic compound
CN110551144A (en) Preparation method of amoxicillin
Coburn et al. An improved synthesis of 3, 6‐diamino‐1, 2, 4, 5‐tetrazine. I
JPH11508258A (en) 2,4,6,8,10,12-hexabenzyl-2,4,6,8,10,12-hexaazatetracyclo [5.5.0.0 {5,9} above. 0 {top 3, 11}] Improved synthesis of dodecane
CN107586267B (en) Synthetic method of taurine hydrochloride (2-amino ethyl taurine hydrochloride)
CN103025743B (en) The manufacture method of carbon imide compound
US4522756A (en) Alkyl, azido, nitro ethers and method of preparation
CN103613593B (en) A kind of preparation method of amide urea derivative
US8697886B2 (en) Di(aminoguanidium) 4,4′,5,5′-tetranitro-2,2′-biimidazole, and preparation method thereof
CN111393360A (en) Nitrogen-rich energetic ionic salt of 2,4, 6-trinitro-3-hydroxypyridine and preparation method thereof
CN105440037A (en) Preparation method for 1,4,5,8-tetranitro-1,4,5,8-tetraazabicyclo[4.4.0]decane
US7220328B1 (en) Low-smoke gas generating low order pressure pulse compositions
NISHIKAWA et al. Behavior of sulfinic acid toward N-chloramines and related compounds
CN107501293A (en) Two furazano piperazine nitramine class energetic ion salt and its synthetic method

Legal Events

Date Code Title Description
C06 Publication
PB01 Publication
C10 Entry into substantive examination
SE01 Entry into force of request for substantive examination
GR01 Patent grant
GR01 Patent grant
CF01 Termination of patent right due to non-payment of annual fee

Granted publication date: 20180626

Termination date: 20210322

CF01 Termination of patent right due to non-payment of annual fee