Amino-nitrobenzene Oxidation To Furosemide Tantamount Synthesis And Properties Of Research

The development trend in explosives is towards high density, high energy and low sensitivity.The replacement of nitro groups by furoxan groups can result in increase of density ,detonation velocity of explosives .So these superior performance of benzofuroxan system compounds have aroused much attention. In the recent years, the studies about benzofuroxans have already got import breakthrough.But we also know, benzofuroxan(BTF) exists a problem of high sensitivity and using insecurely . We have more interest in benzofuroxans with amino and nitro substituents because the effect of pushing electron of amino group increases the bond energy of C-NO2 ,and there are strong intramolecular and intermolecular hydrogen bonds between amino and nitro group. These hydrogen contacts can make the molecular structure more stability .So aminonitrobenzodifuroxan may have good heat resistance and low impact sensitivity. This term has finished some work as follows:(1) We have synthesized aminonitrobenzodifuroxan which have not ever been seen in our country. And there are only one or two reports about it in America. American named aminonitrobenzodifuroxan CL-18. Its molecular structure is between TATB and BTF. CL-18 have amino and nitro groups like TATB, also have furoxans like BTF. Property depends on structure. So CL-18 maybe has low sensitivity like TATB and high energy like BTF. With reference to an American patent, CL-18 was synthesized from 3,5-dinitrobenzoic acid through Schmidt reaction, nitration, azidation and thermal decomposition.(2) The molecular structure of CL-18 and intermediates was determined by FT-IR, MS, NMR and element analysis. XPS of CL-18 was examined and got the binding energy of nitrogen and oxygen elements.(3) The studies on solubility of CL-18 in different organic solvents was tested. Its surface shape was characterized by SEM. The thermal performance analysis was done including thermal loss of weigh(latm,100℃,48h), 5S detonation point, DSC, DTA etc. The nonisothermal formal chemical kinetics of CL-18 was investigatedusing DTA technique, and the datas were dealed with method of Kissinger and Ozawa. The parameters of thermal decomposition of CL-18 including E, A, K were obtained.(4) DATB was synthesized and the possibility of application CL-18 to the explosives of detonation was disscussed . Four explosive formulations were made as follows: ① CL-18: TATB: F2311=50:48:2; ② CL-18: DATE: F2311=30: 68: 2. Among them, CL-18 and DATB were synthesized by us while TATB was got from others.(5) The performances including impact sensitivit), friction sensitivity and electrostatic sensitivity of CL-18 were determined. The impact sensitivity of CL-18 is similar to that of Tetryl. CL-18 which had been fined and F2311 were mixed to get molding powder formulation(CL-18: F2311=98.5 : 1.5). Then the molding powder formulation was used to detonate as impact sheets. The possibility of application CL-18 to detonator was studied.(6) 4,6-diamino-5-nitrobenzofuroxan is designed to synthesis from trichlorobenzene through nitration aminatiom azidation and thermal decomposition. This compound is a new explosive. But we only got the intermediates of the first and second steps(nitration , amination) because the limit of time. The intermediate 3,5-diamino-2,4-dinitrochlorobenzene is also a new compound.( 7 ) Molecular geometry structure and infrared spectrogram of CL-18 were theoretically studied using DFT-B3LYP/6-31G**.