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Studies On Synthesis Of Energetic Compounds Derived From Furazan

Posted on:2014-01-14Degree:MasterType:Thesis
Country:ChinaCandidate:L GaoFull Text:PDF
GTID:2231330395982983Subject:Applied Chemistry
Abstract/Summary:PDF Full Text Request
3,4-Diaminofurazan (DAF) was prepared from glyoxal via diaminoglyoxime (DAG) as an mtermediate.The mechanism of cycloaddition reaction and effect of temperature on this reaction were invesitagated.3,3’-Diamino-4,4’-azofurazan (DAAF) and3,3’-diamino-4,4’-a-zoxyfurazan (DAOAF) were synthesized by using the oxidant NaCIO and OXONETM from DAF respectively. The impact of the ratio of base and OXONETM, temperature of reaction on the yield of DAOAF were studied. DAF, DAAF and DAOAF were nitrated with the pure nitric acid respectively to generate3,4-dinitraminofurazan,3,3’-dinitramino-4,4’-azofurazan, and3,3’-dinitramino-4,4’-azoxyfurazan.3-Amino-4-azidofurazan,3,3’-diazido-4,4’-azofura-zan,3-amino-3’-azido-4,4’-azoxyfurazan or3,3’-diazido-4,4’-azoxyfurazan were prepared separately from bis-diazonium salt of DAF, DAAF and DAOAF by the treatment with NaN3-After storing for several days,3,3’-diazido-4,4’-azofurazan was transformed to5-[4-azido-furazan]-5//-[1,2,3]triazolo[4,5-c]furazan. And the corresponding mechanism of transformation was proposed.3-Amino-4-nitrofurazan(ANF) and3-nitro-4-azidofurazan were prepared separately from DAF and3-amino-4-azidofurazan by using H2O2as the oxidant.N-(2,4,6-trinitrophenyl)-3-amino-4-nitrofurazan was obtained from the substitution reaction of3-amino-4-nitrofurazan and2,4,6-trinitro-chlorobenzene. The effect of solvents and acid scavengers on yield was investigated.3-Amino-4-(tetrazole-5-yl)furazan was obtained from the cycloaddition reaction of sodium azide and3-amino-4-cyanofurazan.3-Amino-4-(tetrazole-5-yl)furazan was treated with KMnO4as azo coupling reagent or oxidant system with H2O2, Na2WO4and CH3SO3H as oxidant to afford azotetrazolylfurazan or3-nitro-4-tetrazolylfurazan, respectively.3-Amino-4-(4-cyano-5-amino-1,2,3-triazol)furaz-an was prepared by cycloaddition from3-amino-4-azidofurazan and malononitrile. The optimal cycloaddition reaction conditions and mechanism were studied.These compounds were characterized by NMR, IR and MS. Explosive parameters were calculated. For furazan compounds, azido or azo group can be attributed to enhance the heats of formation. And nitroamino or azoxy group can increase density and detonation velocity. Combination of furazan ring with azo, azoxy, aromatic ring, triazole or tetrazole group can improve the thermal stability accoding to the analysis result from TG and DSC.
Keywords/Search Tags:organic chemistry, energetic material, furazan, synthesis
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