Bis(1-alkyl-5-aminotetrazolium)dodecahydrododecaborate or bis(2-alkyl-5-aminotetrazolium)dodecahydrododecaborate and bis(5-amino-1,4-dialkyltetrazolium)dodecahydrododecaborate or bis(5-amino-1,3-dialkyltetrazolium)dodecahydrododecaborate as well as preparation method thereof

A technology of dodecahydrododecaboron and aminotetrazolium salts, which is applied in the field of high-energy-density material preparation chemistry, can solve the problems of limitation, inconvenient performance testing and application research, complicated preparation and purification processes, etc., and achieves easy purification and processing The effect of convenience and simple procedures

Inactive Publication Date: 2018-01-05
BEIJING INSTITUTE OF TECHNOLOGYGY
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  • Abstract
  • Description
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AI Technical Summary

Problems solved by technology

However, so far, the reports of borohydride anion 5-aminotetrazolium salts are very limited, and there are only two types, one is bistetrazole-substituted hydroborate (Janiak, Christoph; Esser, LotharZ.Natur., B: Chem.Sci.1993,48(3),394-6); Another kind is icosahedral closed cage type dodecahydrododecaborate 5-aminotetrazole salt (Belletire, J.L.; Schneider, S.; Wight, B.A.; Strauss, S.L. and Shackelford, S.A., Synth. Commun. 2012, 42:155–169)
The latter is extremely hygroscopic, and the preparation and purification processes are complicated, which causes a lot of inconvenience to performance testing and application research.

Method used

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  • Bis(1-alkyl-5-aminotetrazolium)dodecahydrododecaborate or bis(2-alkyl-5-aminotetrazolium)dodecahydrododecaborate and bis(5-amino-1,4-dialkyltetrazolium)dodecahydrododecaborate or bis(5-amino-1,3-dialkyltetrazolium)dodecahydrododecaborate as well as preparation method thereof
  • Bis(1-alkyl-5-aminotetrazolium)dodecahydrododecaborate or bis(2-alkyl-5-aminotetrazolium)dodecahydrododecaborate and bis(5-amino-1,4-dialkyltetrazolium)dodecahydrododecaborate or bis(5-amino-1,3-dialkyltetrazolium)dodecahydrododecaborate as well as preparation method thereof
  • Bis(1-alkyl-5-aminotetrazolium)dodecahydrododecaborate or bis(2-alkyl-5-aminotetrazolium)dodecahydrododecaborate and bis(5-amino-1,4-dialkyltetrazolium)dodecahydrododecaborate or bis(5-amino-1,3-dialkyltetrazolium)dodecahydrododecaborate as well as preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] 9. Suspend 9018g of 1-methyl-5-aminotetrazole in methanol, heat to reflux at 70°C, add excess concentrated hydrochloric acid, react for 2 hours, remove the solvent by suspension evaporation, and then recrystallize with water / methanol to obtain 1-methyl-5 -aminotetrazole hydrochloride; then 1-methyl-5-aminotetrazole hydrochloride and Ag 2 B 12 h 12 Dissolve or suspend in appropriate amount of distilled water respectively, react for half an hour, filter to remove solid matter, then concentrate and cool to crystallize to obtain bis(5-amino-1-methyltetrazole) dodecahydrododecaborate; at 70°C Dry under reduced pressure. 1 H NMR (DMSO-d 6 ,ppm,600MHz):δ8.36(s,6H,2NH 3 ),3.71(s,6H,2NCH 3 ), 1.3-0.4 (platform, 12H, B 12 h 12 ). 13 C NMR (DMSO-d 6 ,ppm,600MHz):δ155.16(ring C),32.26(N-C). 11 BNMR (DMSO-d 6 ,ppm,600MHz):δ-15.5.IR(cm -1 ):ν3358,3302,3246,3172,2459,1681,1027,712,684.ESI-MS(m / z):100([M C2H6N5 ] + ),70.95([M B12H12 / 2] - )

Embodiment 2

[0038] 0.66g K 2 B 12 h 12 and 1.45g of 5-amino-1,4-dimethyltetrazolium iodide were dissolved in deionized water and methanol respectively, and the two were mixed and reacted for 1.5h, then heated at 65°C for half an hour, concentrated and crystallized to obtain twelve Bis(5-amino-1,4-dimethyltetrazolium) hydrogen dodecaborate salt white crystal; dried under reduced pressure at 80°C. 1 H NMR (DMSO-d 6 ,ppm,600MHz):δ9.09(s,4H,2NH 2 ),3.87(s,12H,4NCH3 ), 1.3-0.4 (platform, 12H, B 12 h 12 ). 13 C NMR (DMSO-d 6 ,ppm,600MHz):δ149.0(ring C),34.5(N-C). 11 B NMR (DMSO-d 6 ,ppm,600MHz):δ-15.5.IR(cm -1 ):ν3341,3294,3248,3116,2487,1681,1606,1532,1437,1185,1046,771,716.ESI-MS(m / z):114([M C3H8N5 ] + ),71.35([M B12H12 / 2] - )

Embodiment 3

[0040] (Et 3 NH) 2 B 12 h 12 and 5 amino-1,4-dimethyltetrazolium iodide were mixed in water and acetonitrile at a molar ratio of 1:2 and reacted at reflux for 2 hours, the solvent was removed under reduced pressure, and the residue was recrystallized from water-methanol to obtain twelve Bis(5-amino-1,4-dimethyltetrazolium) hydrogen dodecaborate salt white crystal. Test data is with embodiment 1.

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Abstract

The invention discloses a preparation method of a kind of new high-energy density materials bis(1-alkyl-5-aminotetrazolium)dodecahydrododecaborate or bis(2-alkyl-5-aminotetrazolium)dodecahydrododecaborate and bis(5-amino-1,4-dialkyltetrazolium)dodecahydrododecaborate or bis(5-amino-1,3-dialkyltetrazolium)dodecahydrododecaborate as well as pure products without crystal water. The preparation methodmainly comprises a metathesis reaction between dodecahydrododecaborate and 1-alkyl-5-aminotetrazolium salt and 2-alkyl-5-aminotetrazolium salt or 5-amino-1,4-dialkyltetrazolium salt and 5-amino-1,3-dialkyltetrazolium salt in a suitable medium. The preparation method has the characteristics of simple program, routine operation, treatment convenience and easy purification.

Description

technical field [0001] The invention discloses a novel high-energy nitrogen-rich material dodecahydrododecaboric acid monoalkylation and dialkylation 5-aminotetrazole salt and a preparation method thereof, belonging to the field of high energy density material preparation chemistry. Background technique [0002] Nitrogen-rich heterocyclic compounds play an important role in the research of high-energy-density materials; a large number of studies on nitrogen-rich heterocyclic compounds such as imidazole, triazole, and tetrazole have been reported (Gao, X.; Shreeve, J.M.Chem.Rev.2011 , 111, 7377-7436). As far as tetrazole derivatives are concerned, due to their high nitrogen content, they have high energy density and good gas-forming properties; in addition, their majority sensitivity is low, and the combustion products are environmentally friendly. In the research of high-energy-density materials such as explosives and propellants received great attention from people. Among...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D257/06
Inventor 杨荣杰绳利丽单自兴郭晓燕
Owner BEIJING INSTITUTE OF TECHNOLOGYGY
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