硝基富勒烯衍生物的合成及应用研究
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摘要
本论文主要包括三部分:富勒烯原材料制备研究,新型硝基富勒烯吡咯烷衍生物的理论设计与合成研究,富勒烯及其衍生物在高能炸药和硝胺改性双基推进剂(RDX-CMDB)中的应用研究。
以石墨为原料,采用自制电弧炉制备富勒烯烟炱,研究并获得了电弧法制备富勒烯的最佳工艺条件:氦气压力0.05 MPa,直流电流强度100A,进棒速度6 rad/min,此时富勒烯产率达9.0%;探讨并获得了采用柱色谱法分离C_(60)的适宜工艺条件:以质量比2:1:1的活性炭、三氧化二铝和硅胶混合物为固定相,甲苯为流动相分离,C_(60)提取率达60%,并探讨了其制备机理。
以TNT、硝基苯甲醛、C_(60)、氨基酸以及硝基卤苯等为主要原料,根据Prato反应原理设计、采用间接法合成并分离得到了三类九种新型稳定的硝基富勒烯衍生物,对其中六种的详细工艺条件进行了研究,获得了产物合成的最佳工艺条件,①产物1:C_(60),2-硝基苯甲醛和N-甲基甘氨酸的物质的量比为1:3:6、温度为55℃、反应时间为12h、溶剂甲苯体积为40ml,产率53.5%;②产物2:C_(60),3-硝基苯甲醛和N-甲基甘氨酸的物质的量比为1:1:2、温度为100℃、反应时间为16 h、产率94.8%;③产物3:C_(60),2,4-二硝基苯甲醛和N-甲基甘氨酸的物质的量比为1:2:6、温度为95℃、反应时间为40 h,产率65.8%;④产物5:C_(60),2-硝基苯甲醛和甘氨酸的物质的量比为1:4:6、温度为80℃、反应时间为48 h、溶剂甲苯体积为70 ml,产率81.2%;⑤产物6:C_(60),3-硝基苯甲醛和甘氨酸的物质的量比为1:4:6、温度为100℃、溶剂甲苯体积为80 ml、反应时间为24 h,产率82.1%;⑥产物7:C_(60),4-硝基苯甲醛和甘氨酸的物质的量比为1:2:4、温度为90℃、溶剂甲苯体积为80 ml、反应时间为48 h,产率79.6%;同时,针对微波固相法和油浴加热固相法合成产物8时的立体选择性不同,提出了可能的反应机理,并从理论上进行了解释。
利用UV-Vis、IR、~1H NMR、~(13)C NMR以及MS等结构表征手段对产物的结构进行了确认,证明所合成的九种产物结构与所设计分子相符,为目标化合物。
利用差热分析仪和DSC-TG综合热分析仪对C_(60)及其硝基衍生物的热稳定性进行了研究,结果表明,环境气氛对C_(60)热稳定性影响很大,C_(60)在空气中423.5℃开始分解,放热峰值温度为668.5℃,在氦气中很稳定,仅表现为升华,C_(60)的晶型对其热稳定性也有一定的影响;合成得到的九种硝基富勒烯衍生物都具有较好的热稳定性,分解峰值温度均高于350℃;产物4的5秒爆发点测试结果为253℃。富勒烯[60]硝基衍生物种类、硝基数目、硝基位置对其热稳定性均有影响,同类衍生物,硝基数目越多,热稳定性越差;硝基数量相同时,苯环上硝基不同位置热稳定性顺序为:对位＞邻位＞间位。
首次实验探讨了四种硝基富勒烯衍生物作为HMX的钝感剂的可行性,结果表明,富勒烯的结晶方式对HMX的钝感作用有很大影响,通过CS_2/石油醚快速结晶得到的C_(60)在同等实验条件下对HMX撞击感度降感作用可与石墨相当,摩擦感度也降低到70%;产物2对HMX的钝感作用与石墨相当,产物4对HMX有明显增感作用,促进HMX从燃烧转爆轰;同时,采用DFT/BLYB方法从理论上计算了产物4的气相标准摩尔生成焓、标准摩尔燃烧焓、爆热、爆压和爆速,并通过理论计算探讨了其热分解机理,表明产物4在分解时能释放出较大的能量,具备了新型含能材料的特征。
首次将硝基富勒烯衍生物2引入固体推进剂配方中,进行了实验室模拟研究,运用火焰温度分布实验,研究推进剂燃烧表面温度和催化剂的相关性;通过燃速测试,得出推进剂燃速随压强变化等关系。实验结果表明,相对于单组分催化剂Φ-Pb,CB或2-FS添加剂都能明显增加RDX-CMDB推进剂的燃速,2-FS的效果显著优于CB;相对于双组元催化剂Φ-Pb/β-Cu,CB、产物2、CF和FS添加剂均能使RDX-CMDB推进剂的燃速明显增加,产物2、CF和2-FS的催化效果明显高于CB;在Φ-Pb/β-Cu/C三组元催化体系中,CB、产物2、CF和FS添加剂的催化效果是FS＞产物2＞CF＞CB。产物2与邻苯二甲酸铅(Φ-Pb)具有较好的协同催化作用,能够加剧双基体系凝聚相的分解过程,催化分解产物之间反应,使推进剂的表面温度有所增加,提高推进剂的燃速,降低压强指数,燃烧平台范围增宽且向高压方向移动。
This paper includes three parts:preparation of fullerene,the theoretical design and synthesis of novel pyrrolidine nitro-derivatives,the investigation of the application of fullerene and its derivatives in high energetic explosives and nitramine modified double base propellant(RDX-CMDB).
The fullerence soot is preparated with graphite by arc discharge method.The yield of fullerene is 9.0%under the optimum conditions:0.05MPa Helium pressure,100A direct current intensity,6 rad/min advancing velocity of graphite rod.
The optimum conditions for the column chromatography separation condition of fullerence are:activated carbon,alumina and silica gel mixed in mass ratio of 2:1:1 as stationary phases,toluene as a mobile phase.Under the optimum conditions,the C_(60) extraction rate of 60%is given and the mechanism of preparation is also discussed.
The nine nitro stable fullerene derivatives have been designed,prepared and separated in accordance with the principle of Prato Reaction using TNT,fullerene,amino acids and nitrobenzaldehyde as raw materials.The reaction conditions affecting the yields of the six products of those are investigated in full detail,and the optimum synthetic technology conditions of the products are:①product 1:the molar ratio of C_(60),2-nitrobenzaldehyde and N-methyl-glycine 1:3:6,the temperature 55℃,the reaction time 12h,the volume of toluene 40ml,with the yield of 53.5%;②product 2:the molar ratio of C_(60),3-nitrobenzaldehyde and N-methyl-glycine 1:1:2,the temperature 100℃,the reaction time 16 h,with the yield of 94.8%;③product 3:the molar ratio of C_(60),2,4-2-nitrobenzaldehyde and N-methyl-glycine 1:2:6,the temperature 95℃,the reaction time 40 h,with the yield of 65.8%;④product 5: the molar ratio of C_(60),2-nitrobenzaldehyde and glycine 1:4:6,the temperature 80℃,the reaction time 48 h,the volume of toluene 70ml,with the yield of 81.2%;⑤product 6:the molar ratio of C_(60),3-nitrobenzaldehyde and glycine 1:4:6,the temperature 100℃,the volume of toluene 80 ml,the reaction time 24 h,with the yield of 82.1%;⑥product 7:the molar ratio of C_(60),4-nitrobenzaldehyde and glycine 1:2:4,the temperature 90℃,volume of toluene 80 ml,the reaction time 48 h,with the yield of 79.6%.For the different stereoselectiveity of the product 8 synthesized by microwave-assisted solid-phase reaction and oil bath heating solid-phase reaction,a possible reaction mechanism is put forward and explained in theory.
The structures of the products are characterized by UV-vis,FT-IR,~(13)C NMR,~1H NMR and MS.It proves the molecular structure of the products are the aim compounds.
The thermal stability of C_(60) and its nitro-fullerene derivatives are studied by DTA and DSC-TG.The results show that the atmosphere has a big influence on the thermal stability of C_(60).C_(60) begins to decompose at 423.5℃in the air,the deomposed peak temperature is 668.5℃,but very stable in the helium atmosphere,only sublimate,the crystal shape of C_(60) has a certain influence to its thermal stability.The synthesized nine kinds of nitro-fullerene derivatives all have good thermal stability and their decomposed peak temperatures all exceed 350℃.The thermal explosion temperature for 5 seconds delay of product 4 is 253℃.The category,number and position of nitryl group in nitro-fullerene derivatives all have influence on their thermal stability.To the analogous derivatives,the bigger the number of nitro group is,the worse thermal stability is.The sequence on the thermal stability of nitro group position is:para site＞ortho site＞meta site when the number of nitro group is equal.
The insensitive action of the four products on HMX is studied preliminarily.The results show that the crystal forms of fullerene have some effect to the desensitization of HMX.C_(60) obtained through the rapid crystallization of CS_2/petroleum has the same effect on the impact sensitivity of HMX as well as Graphite,friction sensitivity is also reduced to 70%.Insensitive action of the product 2 on HMX is equivalent to that of graphite,the product 4 has a sensitization to HMX,promoting change of HMX from combustion to detonation.At the same time,the gas standard molar enthalpy of formation,standard molar enthalpy of combustion,explosion heat,detonation pressure and detonation velocity are calculated theoretically using DFT/BLYB method.The theoretical analysis has carried on to reaction mechanism of thermal decomposition of the product 4 which indicate product 4 will release larger energy in the decomposition and has the properties of new type of energetic material.
The nitro fullerene derivative 2 are introduced into solid propellant firstly in simulation test,the relevance of the temperature of propellant burning surface and the catalyst is studied by flame temperature distribution experiment,and the relations of propellant burning rate with the pressure changing are obtained.The experimental result indicate that,compared toΦ-Pb for the single-component catalyst,CB and 2-FS additives could increase the burning rate of RDX-CMDB propellant obviously,and 2-FS is significantly superior to the effect of CB;compared toΦ-Pb/β-Cu for the bicomponent catalyst,CB,product 2,CF and 2-FS additives could increase the burning rate of RDX-CMDB propellant obviously,and product 2,CF and 2-FS are significantly superior to the effect of CB;for tripropellant catalyst system,the catalytic effect of FS,product 2,CF and CB increase in succession. nitro-fullerenes and p-phthalic acid lead(Φ-Pb) had better coordination catalysis,which can intensify the decomposition of condensed phase of double-base system,catalyze the reaction between the decomposition products,increase the surface temperature of catalysis,increase the propellant burning rate,reduce the pressure exponent,widen the scope of the burning platform and make it move in the direction of high pressure.
以石墨为原料,采用自制电弧炉制备富勒烯烟炱,研究并获得了电弧法制备富勒烯的最佳工艺条件:氦气压力0.05 MPa,直流电流强度100A,进棒速度6 rad/min,此时富勒烯产率达9.0%;探讨并获得了采用柱色谱法分离C_(60)的适宜工艺条件:以质量比2:1:1的活性炭、三氧化二铝和硅胶混合物为固定相,甲苯为流动相分离,C_(60)提取率达60%,并探讨了其制备机理。
以TNT、硝基苯甲醛、C_(60)、氨基酸以及硝基卤苯等为主要原料,根据Prato反应原理设计、采用间接法合成并分离得到了三类九种新型稳定的硝基富勒烯衍生物,对其中六种的详细工艺条件进行了研究,获得了产物合成的最佳工艺条件,①产物1:C_(60),2-硝基苯甲醛和N-甲基甘氨酸的物质的量比为1:3:6、温度为55℃、反应时间为12h、溶剂甲苯体积为40ml,产率53.5%;②产物2:C_(60),3-硝基苯甲醛和N-甲基甘氨酸的物质的量比为1:1:2、温度为100℃、反应时间为16 h、产率94.8%;③产物3:C_(60),2,4-二硝基苯甲醛和N-甲基甘氨酸的物质的量比为1:2:6、温度为95℃、反应时间为40 h,产率65.8%;④产物5:C_(60),2-硝基苯甲醛和甘氨酸的物质的量比为1:4:6、温度为80℃、反应时间为48 h、溶剂甲苯体积为70 ml,产率81.2%;⑤产物6:C_(60),3-硝基苯甲醛和甘氨酸的物质的量比为1:4:6、温度为100℃、溶剂甲苯体积为80 ml、反应时间为24 h,产率82.1%;⑥产物7:C_(60),4-硝基苯甲醛和甘氨酸的物质的量比为1:2:4、温度为90℃、溶剂甲苯体积为80 ml、反应时间为48 h,产率79.6%;同时,针对微波固相法和油浴加热固相法合成产物8时的立体选择性不同,提出了可能的反应机理,并从理论上进行了解释。
利用UV-Vis、IR、~1H NMR、~(13)C NMR以及MS等结构表征手段对产物的结构进行了确认,证明所合成的九种产物结构与所设计分子相符,为目标化合物。
利用差热分析仪和DSC-TG综合热分析仪对C_(60)及其硝基衍生物的热稳定性进行了研究,结果表明,环境气氛对C_(60)热稳定性影响很大,C_(60)在空气中423.5℃开始分解,放热峰值温度为668.5℃,在氦气中很稳定,仅表现为升华,C_(60)的晶型对其热稳定性也有一定的影响;合成得到的九种硝基富勒烯衍生物都具有较好的热稳定性,分解峰值温度均高于350℃;产物4的5秒爆发点测试结果为253℃。富勒烯[60]硝基衍生物种类、硝基数目、硝基位置对其热稳定性均有影响,同类衍生物,硝基数目越多,热稳定性越差;硝基数量相同时,苯环上硝基不同位置热稳定性顺序为:对位＞邻位＞间位。
首次实验探讨了四种硝基富勒烯衍生物作为HMX的钝感剂的可行性,结果表明,富勒烯的结晶方式对HMX的钝感作用有很大影响,通过CS_2/石油醚快速结晶得到的C_(60)在同等实验条件下对HMX撞击感度降感作用可与石墨相当,摩擦感度也降低到70%;产物2对HMX的钝感作用与石墨相当,产物4对HMX有明显增感作用,促进HMX从燃烧转爆轰;同时,采用DFT/BLYB方法从理论上计算了产物4的气相标准摩尔生成焓、标准摩尔燃烧焓、爆热、爆压和爆速,并通过理论计算探讨了其热分解机理,表明产物4在分解时能释放出较大的能量,具备了新型含能材料的特征。
首次将硝基富勒烯衍生物2引入固体推进剂配方中,进行了实验室模拟研究,运用火焰温度分布实验,研究推进剂燃烧表面温度和催化剂的相关性;通过燃速测试,得出推进剂燃速随压强变化等关系。实验结果表明,相对于单组分催化剂Φ-Pb,CB或2-FS添加剂都能明显增加RDX-CMDB推进剂的燃速,2-FS的效果显著优于CB;相对于双组元催化剂Φ-Pb/β-Cu,CB、产物2、CF和FS添加剂均能使RDX-CMDB推进剂的燃速明显增加,产物2、CF和2-FS的催化效果明显高于CB;在Φ-Pb/β-Cu/C三组元催化体系中,CB、产物2、CF和FS添加剂的催化效果是FS＞产物2＞CF＞CB。产物2与邻苯二甲酸铅(Φ-Pb)具有较好的协同催化作用,能够加剧双基体系凝聚相的分解过程,催化分解产物之间反应,使推进剂的表面温度有所增加,提高推进剂的燃速,降低压强指数,燃烧平台范围增宽且向高压方向移动。
This paper includes three parts:preparation of fullerene,the theoretical design and synthesis of novel pyrrolidine nitro-derivatives,the investigation of the application of fullerene and its derivatives in high energetic explosives and nitramine modified double base propellant(RDX-CMDB).
The fullerence soot is preparated with graphite by arc discharge method.The yield of fullerene is 9.0%under the optimum conditions:0.05MPa Helium pressure,100A direct current intensity,6 rad/min advancing velocity of graphite rod.
The optimum conditions for the column chromatography separation condition of fullerence are:activated carbon,alumina and silica gel mixed in mass ratio of 2:1:1 as stationary phases,toluene as a mobile phase.Under the optimum conditions,the C_(60) extraction rate of 60%is given and the mechanism of preparation is also discussed.
The nine nitro stable fullerene derivatives have been designed,prepared and separated in accordance with the principle of Prato Reaction using TNT,fullerene,amino acids and nitrobenzaldehyde as raw materials.The reaction conditions affecting the yields of the six products of those are investigated in full detail,and the optimum synthetic technology conditions of the products are:①product 1:the molar ratio of C_(60),2-nitrobenzaldehyde and N-methyl-glycine 1:3:6,the temperature 55℃,the reaction time 12h,the volume of toluene 40ml,with the yield of 53.5%;②product 2:the molar ratio of C_(60),3-nitrobenzaldehyde and N-methyl-glycine 1:1:2,the temperature 100℃,the reaction time 16 h,with the yield of 94.8%;③product 3:the molar ratio of C_(60),2,4-2-nitrobenzaldehyde and N-methyl-glycine 1:2:6,the temperature 95℃,the reaction time 40 h,with the yield of 65.8%;④product 5: the molar ratio of C_(60),2-nitrobenzaldehyde and glycine 1:4:6,the temperature 80℃,the reaction time 48 h,the volume of toluene 70ml,with the yield of 81.2%;⑤product 6:the molar ratio of C_(60),3-nitrobenzaldehyde and glycine 1:4:6,the temperature 100℃,the volume of toluene 80 ml,the reaction time 24 h,with the yield of 82.1%;⑥product 7:the molar ratio of C_(60),4-nitrobenzaldehyde and glycine 1:2:4,the temperature 90℃,volume of toluene 80 ml,the reaction time 48 h,with the yield of 79.6%.For the different stereoselectiveity of the product 8 synthesized by microwave-assisted solid-phase reaction and oil bath heating solid-phase reaction,a possible reaction mechanism is put forward and explained in theory.
The structures of the products are characterized by UV-vis,FT-IR,~(13)C NMR,~1H NMR and MS.It proves the molecular structure of the products are the aim compounds.
The thermal stability of C_(60) and its nitro-fullerene derivatives are studied by DTA and DSC-TG.The results show that the atmosphere has a big influence on the thermal stability of C_(60).C_(60) begins to decompose at 423.5℃in the air,the deomposed peak temperature is 668.5℃,but very stable in the helium atmosphere,only sublimate,the crystal shape of C_(60) has a certain influence to its thermal stability.The synthesized nine kinds of nitro-fullerene derivatives all have good thermal stability and their decomposed peak temperatures all exceed 350℃.The thermal explosion temperature for 5 seconds delay of product 4 is 253℃.The category,number and position of nitryl group in nitro-fullerene derivatives all have influence on their thermal stability.To the analogous derivatives,the bigger the number of nitro group is,the worse thermal stability is.The sequence on the thermal stability of nitro group position is:para site＞ortho site＞meta site when the number of nitro group is equal.
The insensitive action of the four products on HMX is studied preliminarily.The results show that the crystal forms of fullerene have some effect to the desensitization of HMX.C_(60) obtained through the rapid crystallization of CS_2/petroleum has the same effect on the impact sensitivity of HMX as well as Graphite,friction sensitivity is also reduced to 70%.Insensitive action of the product 2 on HMX is equivalent to that of graphite,the product 4 has a sensitization to HMX,promoting change of HMX from combustion to detonation.At the same time,the gas standard molar enthalpy of formation,standard molar enthalpy of combustion,explosion heat,detonation pressure and detonation velocity are calculated theoretically using DFT/BLYB method.The theoretical analysis has carried on to reaction mechanism of thermal decomposition of the product 4 which indicate product 4 will release larger energy in the decomposition and has the properties of new type of energetic material.
The nitro fullerene derivative 2 are introduced into solid propellant firstly in simulation test,the relevance of the temperature of propellant burning surface and the catalyst is studied by flame temperature distribution experiment,and the relations of propellant burning rate with the pressure changing are obtained.The experimental result indicate that,compared toΦ-Pb for the single-component catalyst,CB and 2-FS additives could increase the burning rate of RDX-CMDB propellant obviously,and 2-FS is significantly superior to the effect of CB;compared toΦ-Pb/β-Cu for the bicomponent catalyst,CB,product 2,CF and 2-FS additives could increase the burning rate of RDX-CMDB propellant obviously,and product 2,CF and 2-FS are significantly superior to the effect of CB;for tripropellant catalyst system,the catalytic effect of FS,product 2,CF and CB increase in succession. nitro-fullerenes and p-phthalic acid lead(Φ-Pb) had better coordination catalysis,which can intensify the decomposition of condensed phase of double-base system,catalyze the reaction between the decomposition products,increase the surface temperature of catalysis,increase the propellant burning rate,reduce the pressure exponent,widen the scope of the burning platform and make it move in the direction of high pressure.
引文
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