以磁性Fe3O4负载质子化过氧钨酸盐为催化剂,在不用三氟乙酸的情况下,以双氧水为氧化剂,将2,6-二甲氧基吡嗪、2,6-二氯吡嗪和2-氯-6-甲氧基吡嗪高效地氧化为其相应的氮氧化物2,6-二氨基-3,5-二硝基-1-氧吡嗪(LLM-105).典型条件为:底物10 mmol,CH3 CN 30 mL,催化剂Fe3O4/CS/HWO 0.1 g(约0.1 mmol),60℃分5次逐滴加入30%双氧水5 mL.反应混合物溶液经萃取和柱色谱法提纯,得产物,收率一般为60%~73%.使用高斯03量化计算程序对氧化过程进行了理论计算,结果与实验数据相符.
参考文献
[1] | Korkin A A,Bartlett R J.Theoretical Prediction of 2,4,6-Trinitro-1,3,5-triazine (TNTA).A New,Powerful,High-Energy Density Material[J].J Am Chem Soc,1996,118:12244-12245. |
[2] | Fried L E,Manaa M R,Pagoria P F,et al.Design and Synthesis of Energetic Materials[J].Annu Rev MaterRes,2001,31:291-323. |
[3] | Strout D L.A Cage Isomers of N14 and N16:Nitrogen Molecules That Are Not a Multiple of Six[J].J Phys Chem,2004,108:10911-10916. |
[4] | Lee R S,Cutting J L,Hodgin R L,et al.The 11th International Detonation Symposium[R],1998,UCRL-JL-127795. |
[5] | Cutting J L,Hodgin R L,Hoffman M D,et al.The 1 1 th International Detonation Symposium[R],1998,UCRL-JL-131623. |
[6] | Tarver C M,Urtiew P A,Tran T D.Sensitivity of 2,6-Diamino-3,5-dinitropyrazine-1-oxide[J].J Energy Mater,2005,23(3):183-203. |
[7] | Pagoria P F.Synthesis of LLM-105[R].JOWOG 9 Meeting,1997,UCRL-JC-117228. |
[8] | Pagoria P F.Synthesis,Scale-up and Characterization of 2,6-Diamino-3,5-dinitro-pyrazine-l-oxide (LLM-105)[R].JOWOG 9 Meeting,1998,UCRL-JC-130518. |
[9] | Pagoria P F,Mitchell A R,Schmidt R D.Munitions Technology Development Program[R],1999,UCRL-ID-103483-99. |
[10] | Pagoria P F,Lee G S,Mitchell A R,et al.The Synthesis of Amino-and Nitro-Substituted Heterocycles as Insensitive Energetic Materials[R],2001,UCRL-JC-142918. |
[11] | Tran T D,Pagoria P F,Hoffman M D,et al.The 12th International Detonation Symposium[R],2002,UCRL-JC-144963. |
[12] | LI Haibo,CHENG Bibo,LI Hongzhen.Synthesis of 2,6-Diamino-3,5-dinitro Pyrazine-l-oxide[J].Chinese J Org Chem,2007,27(1):112-115 (in Chinese).李海波,程碧波,李洪珍,等.2,6-二氨基-3,5-二硝基吡嗪-1-氧化物的合成[J].有机化学,2007,27(1):112-115. |
[13] | DENG Mingzhe,YE Zhihu,SU Haipeng.The Recycling of Trifluoroacetic Acid in the Synthesis of LLM-105 Explosive[J].Chinese J Explos Propell,2009,32(4):50-52(in Chinese).邓明哲,叶志虎,苏海鹏.LLM-105炸药合成中三氟乙酸的回收利用[J].火炸药学报,2009,32(4):50-52. |
[14] | Pagoria P F.New Synthesis of 2,6-Diamino-3,5-dinitropyrazine-1-oxide from 2,6-Diaminopyrazine-1-oxide,US Patent,20090299067A1[P],2009. |
[15] | Karimi B,Farhangi E.A Highly Recyclable Magnetic Core-Shell Nanoparticle-Supported TEMPO Catalyst for Efficient Metal-and Halogen-Free Aerobic Oxidation of Alcohols in Water[J].Chem Eur J,2011,17:6056-6060. |
[16] | Ishimoto R,Kamata K,Mizuno N.A Highly Active Protonated Tetranuclear Peroxotungstate for Oxidation with Hydrogen Peroxide[J].Angew Chem Int Ed,2012,51:4662-4665. |
[17] | Hirschhiiuser C,Haseler C A,Gallagher T.Core Modification of Cytisine:A Modular Synthesis[J].Angew Chem,Int E,2011,50:5162-5165. |
[18] | Cui Z M,Xing W,Liu C P,et al.Chitesan/heteropolyacid Composite Membranes for Direct Methanol Fuel Cell[J].J Power Sources,2009,188:24-29. |
上一张
下一张
上一张
下一张
计量
- 下载量()
- 访问量()
文章评分
- 您的评分:
-
10%
-
20%
-
30%
-
40%
-
50%