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Study on the Synthesis of Halo and Nitro Derivatives of Adamantane

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Tutor: WangJianLong
School: University of North
Course: Applied Chemistry
Keywords: adamantane,1-carboxyadamantane,photocatalytic,halogenated reaction
CLC: TQ560.1
Type: Master's thesis
Year:  2014
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Abstract:
With the increasing request on energetic materials from goals of precision strike,efficient damage and high survivability capabilities proposed in the development of modernweapons, the synthesis of the organic cage energetic material has become a hotspot of novelsingle compound explosive. Polynitroadamantane is an ideal military explosive which is ofheat-resistan and high-energy with low sense. Halogenated adamantane is an importantintermediate of polynitroadamantane Therefore, it is important to study on the synthesis ofhalogenated adamantane and polynitroadmantane.As to the study on the synyhesis of chlorinated adamantane, various chlorinatedderivatives of adamantane were prepared using adamantane as raw material and using t-butylchloride, thionyl chloride and carbon tetrachloride as chlorinating agent. The products werecharacterized by IR,13CMR and GC-MS. The results showed that1-Chloroadamantane waspure and polychloroadamantane was a mixture of isomers. The effects of different catalysts onthe yield were studied in the preparation of1-Chloroadamantane. The results indicated theyield was the highest using AlCl3as catalyst. Thionyl chloride as a chlorinating agent hadhigher activity than carbon tetrachloride in the preparation of polychloroadamantane, and thebest reaction condition was determined by single factor experiments.Polychloroadamantanecarboxylic acid was exploratorily synthesized under UV using1-Carboxyadamantane as raw material for the first time in the domestic. The products werecharacterized by melting point, thin layer chromatography and infrared spectroscopy. Theinfluences on the reaction were studied, for example, the UV light source and the reactiontemperature. The results showed that UV mercury lamp had better action than ordinaryultraviolet disinfection lamp.The reaction temperature had little effect on the reaction andventilation rate must be controled.1-Bromoadamantane,1,3-Dibromoadamantane and1,3,5,7-Tetrabromoadamantane wereprepared by changing the catalysts and reaction conditions using bromine as brominatingagent.1,3,5,7-Tetraiodoadamantane was synthesized by halogen replacement reaction.1,3,5, 7-Tetranitroadamantane(TNA) was tentatively prepared by1,3,5,7-Tetraiodoadamantaneusing HNO3as nitrating agents. However, TNA was not successfully prepared.The vacuum crystal morphology of TNA was predicted using molecular dynamicsmethod. The results showed that the crystal of TNA was nearly spherical in vacuum conditionand the important crystal planes in morphology were (101),(110) and (002). The detonationperformance of TNA was calculated by Kamlet formula, and the result was6984m/s and19.98GPa, which was very close to the literature values.
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