超分子含能化合物的制备及其钝感性能研究
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摘要
钝感炸药是目前含能材料发展的方向之一。论文首次提出超分子含能化合物来实现弹药钝感的目的。合成了5个未见文献报道的氮杂杯芳烃及其衍生物,制备了15个未见文献报道的超分子含能化合物。论文首次提出采用超分子化学的手段来降低含能化合物的机械感度。
合成了对硝基杯[8]芳烃,采用量子化学半经验AM1和密度泛函B3LYP/6-31G*方法,分别对主、客体及其超分子体系进行了结构优化和理论计算,计算结果表明对硝基杯[8]芳烃分别与RDX、HMX通过一系列氢键综合作用形成了超分子体系。采用发射光谱与紫外光谱法对超分子体系中主客体的化学计量比进行了确定,结果表明:对硝基杯[8]芳烃与RDX在DMF溶液中和HMX在氯仿溶液中均能形成化学计量比为1:1的配合物,稳定常数分别为20803和3119.90。采用溶剂扩散技术制备了超分子含能化合物,通过X-射线衍射对其进行了表征。
合成了间苯二胺[2]-一氯均三嗪[2]氮杂杯芳烃和未见文献报道的对苯二胺[2]-一氯均三嗪[2]氮杂杯芳烃,通过叠氮化和胺解反应合成了4个未见文献报道的氮杂杯芳烃衍生物,并进行了结构表征。通过量子化学计算探讨了氮杂杯芳烃与含能化合物黑索今、奥克托今之间的相互作用,结果表明黑索今与氮杂杯[4]芳烃及其衍生物之间通过氢键作用可以形成超分子体系;而奥克托今不能与氮杂杯[4]芳烃及其衍生物形成稳定的超分子体系。采用荧光光谱法研究了黑索今、奥克托今与氮杂杯[4]芳烃及其衍生物在溶液中的配合性能,结果表明只有对苯二胺[2]-(6-叠氮基)均三嗪[2]氮杂杯芳烃可以与黑索今形成较为稳定的超分子体系。采用溶剂扩散技术制备了超分子含能化合物,通过X-射线衍射进行了表征。
分别以混酸和浓硝酸为硝化剂合成了β-环糊精硝酸酯,通过柱层析得到了5种不同硝化度的产物。以β-环糊精及其5种硝酸酯为主体,含能化合物黑索今、奥克托今为客体,采用共沉淀法制备了12种超分子含能化合物,通过红外光谱、DSC与XRD对其进行了表征,采用Job连续滴定法确定了该类超分子化合物中主客体的化学计量比为1:1。
采用卡斯特落锤法考察了15种超分子含能化合物的撞击感度。结果表明对硝基杯[8]芳烃、氮杂杯芳烃、环糊精、环糊精硝酸酯-7和环糊精硝酸酯-9这几种化合物通过与黑索今、奥克托今配合,都能够对黑索今和奥克托今起到显著的降低感度的作用。
It is one of the research and development focus on energetic materials to study insensitive explosive. Five new N-azo calixarene derivatives were synthesized and fifteen novel energetic supramolecule compounds were prepared and the new idea, i.e to depress the sensitive of the energetic material through supramolecule chemistry, was put forward for the first time in this thesis.
p-Nitro-calix[8]arene was synthesized using p-t-butylphenol and formaldehyde as starting materials, the structural optimization and theoretical analysis of host, guest and supramolecule system were operated by quantum chemistry half-empirical AM1 and DFT-B3LYP/6-31G* methods. The result showed that the complex be obtained between p-nitro-calix[8]arene and RDX, HMX through a series of hydrogen bonds. The molar ratio between host and guest of the complex was determined via UV and Fluroscence spectrum. Results revealed that p-nitro-calix[8]arene can complex with RDX in DMF and HMX in CHCl3, and the molar ratio of host and guest is 1:1. The stability constant of these two complexes are 20803 and 3119.90, respectively. Two superamoleculs were prepared via solvent diffusion method and charactered by XRD.
Two aza-bridged calix[2]arene[2]triazines were synthesized by using cyanuric chloride, m-phenylenediamine and p-phenylenediamine as starting materials, and four novel derivatives were prepared through azotization and amination reactions. Their structures were charactered. Interactions between tetraazacalix[2]arene[2]triazines and RDX, HMX were discussed through quatum chemistry. The result showed RDX can just be embedded by tetraaza-p-phenyldiaminecalix[2]arene-[2]-(6-azido)triazine to make a complex through a series of hydrogen bonds, whereas HMX can’t. One superamolecule that tetraazacalix[2]arene[2]triazines as host and RDX as guest was prepared via solvent diffusion method and charactered by XRD.
β-Cyclodextrin nitric esters(NCD) were synthesized by using HNO3 and mix acid, respectively. Five pure NCD with different nitration degree were obtained through column chromatography. Twelve superamolecule energetic compounds were prepared via co-deposition method using five NCD with different nitration degree as host and RDX, HMX as guest. Their structures were identified through XRD and IR. The molar ratio of host to guest is 1:1 which was determined by Job’s method.
Impact sensitivity of fifteen supramolecule energetic compounds prepared above were measured by using Kust drop hammer. Results showed that the impact sensitivity of RDX and HMX were decreased remarkably after they were embeded by p-nitro-calix[8]arene, tetraazacalix[2]arene[2]triazines, cyclodextrin, NCD-7, and NCD-9, respectively.
合成了对硝基杯[8]芳烃,采用量子化学半经验AM1和密度泛函B3LYP/6-31G*方法,分别对主、客体及其超分子体系进行了结构优化和理论计算,计算结果表明对硝基杯[8]芳烃分别与RDX、HMX通过一系列氢键综合作用形成了超分子体系。采用发射光谱与紫外光谱法对超分子体系中主客体的化学计量比进行了确定,结果表明:对硝基杯[8]芳烃与RDX在DMF溶液中和HMX在氯仿溶液中均能形成化学计量比为1:1的配合物,稳定常数分别为20803和3119.90。采用溶剂扩散技术制备了超分子含能化合物,通过X-射线衍射对其进行了表征。
合成了间苯二胺[2]-一氯均三嗪[2]氮杂杯芳烃和未见文献报道的对苯二胺[2]-一氯均三嗪[2]氮杂杯芳烃,通过叠氮化和胺解反应合成了4个未见文献报道的氮杂杯芳烃衍生物,并进行了结构表征。通过量子化学计算探讨了氮杂杯芳烃与含能化合物黑索今、奥克托今之间的相互作用,结果表明黑索今与氮杂杯[4]芳烃及其衍生物之间通过氢键作用可以形成超分子体系;而奥克托今不能与氮杂杯[4]芳烃及其衍生物形成稳定的超分子体系。采用荧光光谱法研究了黑索今、奥克托今与氮杂杯[4]芳烃及其衍生物在溶液中的配合性能,结果表明只有对苯二胺[2]-(6-叠氮基)均三嗪[2]氮杂杯芳烃可以与黑索今形成较为稳定的超分子体系。采用溶剂扩散技术制备了超分子含能化合物,通过X-射线衍射进行了表征。
分别以混酸和浓硝酸为硝化剂合成了β-环糊精硝酸酯,通过柱层析得到了5种不同硝化度的产物。以β-环糊精及其5种硝酸酯为主体,含能化合物黑索今、奥克托今为客体,采用共沉淀法制备了12种超分子含能化合物,通过红外光谱、DSC与XRD对其进行了表征,采用Job连续滴定法确定了该类超分子化合物中主客体的化学计量比为1:1。
采用卡斯特落锤法考察了15种超分子含能化合物的撞击感度。结果表明对硝基杯[8]芳烃、氮杂杯芳烃、环糊精、环糊精硝酸酯-7和环糊精硝酸酯-9这几种化合物通过与黑索今、奥克托今配合,都能够对黑索今和奥克托今起到显著的降低感度的作用。
It is one of the research and development focus on energetic materials to study insensitive explosive. Five new N-azo calixarene derivatives were synthesized and fifteen novel energetic supramolecule compounds were prepared and the new idea, i.e to depress the sensitive of the energetic material through supramolecule chemistry, was put forward for the first time in this thesis.
p-Nitro-calix[8]arene was synthesized using p-t-butylphenol and formaldehyde as starting materials, the structural optimization and theoretical analysis of host, guest and supramolecule system were operated by quantum chemistry half-empirical AM1 and DFT-B3LYP/6-31G* methods. The result showed that the complex be obtained between p-nitro-calix[8]arene and RDX, HMX through a series of hydrogen bonds. The molar ratio between host and guest of the complex was determined via UV and Fluroscence spectrum. Results revealed that p-nitro-calix[8]arene can complex with RDX in DMF and HMX in CHCl3, and the molar ratio of host and guest is 1:1. The stability constant of these two complexes are 20803 and 3119.90, respectively. Two superamoleculs were prepared via solvent diffusion method and charactered by XRD.
Two aza-bridged calix[2]arene[2]triazines were synthesized by using cyanuric chloride, m-phenylenediamine and p-phenylenediamine as starting materials, and four novel derivatives were prepared through azotization and amination reactions. Their structures were charactered. Interactions between tetraazacalix[2]arene[2]triazines and RDX, HMX were discussed through quatum chemistry. The result showed RDX can just be embedded by tetraaza-p-phenyldiaminecalix[2]arene-[2]-(6-azido)triazine to make a complex through a series of hydrogen bonds, whereas HMX can’t. One superamolecule that tetraazacalix[2]arene[2]triazines as host and RDX as guest was prepared via solvent diffusion method and charactered by XRD.
β-Cyclodextrin nitric esters(NCD) were synthesized by using HNO3 and mix acid, respectively. Five pure NCD with different nitration degree were obtained through column chromatography. Twelve superamolecule energetic compounds were prepared via co-deposition method using five NCD with different nitration degree as host and RDX, HMX as guest. Their structures were identified through XRD and IR. The molar ratio of host to guest is 1:1 which was determined by Job’s method.
Impact sensitivity of fifteen supramolecule energetic compounds prepared above were measured by using Kust drop hammer. Results showed that the impact sensitivity of RDX and HMX were decreased remarkably after they were embeded by p-nitro-calix[8]arene, tetraazacalix[2]arene[2]triazines, cyclodextrin, NCD-7, and NCD-9, respectively.
引文
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