|本期目录/Table of Contents|

[1]王彬,周彦水,吴敏杰,等.3-氨基-4-偕氨肟基呋咱及其含能衍生物合成研究进展[J].火炸药学报,2018,41(3):213-222.[doi:10.14077/j.issn.1007-7812.2018.03.001]
 WANG Bin,ZHOU Yan-shui,WU Min-jie,et al.Research Progress on Synthesis of 3-Amino-4-aminoximiofurazan and Its Energetic Derivatives[J].,2018,41(3):213-222.[doi:10.14077/j.issn.1007-7812.2018.03.001]
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3-氨基-4-偕氨肟基呋咱及其含能衍生物合成研究进展()
     
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《火炸药学报》[ISSN:1007-7812/CN:61-1310/TJ]

卷:
41卷
期数:
2018年第3期
页码:
213-222
栏目:
出版日期:
2018-06-29

文章信息/Info

Title:
Research Progress on Synthesis of 3-Amino-4-aminoximiofurazan and Its Energetic Derivatives
作者:
王彬 周彦水 吴敏杰 李普瑞 李亚南 王伯周
西安近代化学研究所, 陕西 西安 710065
Author(s):
WANG Bin ZHOU Yan-shui WU Min-jie LI Pu-rui LI Ya-nan WANG Bo-zhou
Xi’an Modern Chemistry Research Institute, Xi’an 710065, China
关键词:
3-氨基-4-偕氨肟基呋咱AAOF呋咱含能衍生物高能量密度化合物呋咱胺呋咱醚
Keywords:
3-amino-4-aminoximiofurazanAAOFfurazan energetic derivativeshigh energy density materialfurazan aminefurazan ether
分类号:
TJ55;O62
DOI:
10.14077/j.issn.1007-7812.2018.03.001
文献标志码:
-
摘要:
综述了3-氨基-4-偕氨肟基呋咱(AAOF)的几种典型合成方法;基于AAOF分子结构中氨基、偕氨肟基的反应活性,可合成3,4-双(4’-氨基呋咱-3’-基)氧化呋咱(DATF)、3,4-双(4’-硝基呋咱-3’-基)氧化呋咱(DNTF)、3,4-双(4’-叠氮基呋咱-3’-基)氧化呋咱(DAZTF)、呋咱胺含能化合物、呋咱醚(FOF-2、FOF-13、BFFO、TFO)等典型含能化合物。系统介绍了上述8大系列30种高含能化合物的合成技术途径及主要的物化性能,有望在高能炸药、高能推进剂等领域得到应用。附参考文献56篇。
Abstract:
Several typical synthetic methods of 3-amino-4-aminoximiofurazan(AAOF)were reviewed. Based on the reaction activity of amino and amidoximo group in the AAOF, typical energetic compounds such as 3,4-bis(4’-aminofurazano-3’) furoxan(DATF),3,4-bis(4’-nitrofurazan-3’-yl) furoxan(DNTF),3,4-bis(4’-azidofurazano-3’-yl) furoxan(DAZTF), furazan amine energetic compounds and furazan ethers(FOF-2, FOF-13, BFFO, TFO)etc. can be synthesized. The synthetic technology and main physicochemical properties of the above eight series, thirty kinds of high energetic compounds, were systematically introduced and are expected to be applied in the fields of high energy explosives and high energy propellants. 56 References are attached.

参考文献/References:

[1] Sheremetev A B.Chemistry of furazans fused to five-menbered rings[J]. Journal of Heterocyclic Chemistry,1995,32(2):371-385.
[2] Sheremetev A B,Kulagina V O,Aleksandrova N S. Amino as key synthons for construction of high energetic materials[C]//Proceeding of the 21st International Pyrotechnics Seminar.Beijing:International Pyrotechnics Society,1995:249-254.
[3] Pivina T S,Sukhachev D V,Evtushenko A V. Comparative characteristic of energy content calculating methods for the furazan series as an example of energetic materials[J]. Propellants,Explosives,Pyrotechnics,1995,20:5-10.
[4] 李战雄,唐松青,欧育湘,等.呋咱含能衍生物合成研究进展[J].含能材料,2002,10(2):59-65. LI Zhan-xiong,TANG Song-qing,OU Yu-xiang,et al.Synthesis status of furazano energetic derivatives[J]. Chinese Journal of Energetic Materials,2002,10(2):59-65.
[5] 苗艳玲,张同来,乔小晶,等.4,6-二硝基苯并氧化呋咱的制备、晶体结构及热分解机理[J].有机化学,2004,24(2):205-209. MIAO Yan-ling,ZHANG Tong-lai,QIAO Xiao-jing,et al. Preparation crystal structure and thermal decomposition mechanisms of 4,6-dinitrobenzofuroxan[J]. Journal of Organic Chemistry,2004,24(2):205-209.
[6] LI Zhan-xiong,TANG Song-qing,LIU Jin-tao,et al.Synthesis and crystal structure of 3,4-bis(azidoacetamino)furazan[J]. Chinese Journal Structure Chemistry,2003,22(1):25-28.
[7] 胡焕性,张志忠,赵凤起,等.高能量密度材料3,4-二硝基呋咱基氧化呋咱性能及应用研究[J].兵工学报, 2004,25(2):155-158. HU Huan-xing,ZHANG Zhi-zhong,ZHAO Feng-qi,et al.A study on the properties and applicaion of high energy density material DNTF[J]. Acta Armamentarii, 2004,25(2):155-158.
[8] 李洪珍,周小清,李金山,等.3-氨基-4-硝基呋咱和3,3’-二硝基-4,4’-偶氮呋咱的合成研究[J].有机化学,2008,28(9):1646-1648. LI Hong-zhen,ZHOU Xiao-qing,LI Jin-shan,et al. Synthesis of 3-aminno-4-nitrofurazan and 3,3’-dinitro-4,4’-azofurazan[J]. Chinese Journal of Organic Chemistry,2008,28(9):1646-1648.
[9] 王建龙,欧育湘,吕连营,等.氨基硝基苯并二氧化呋咱与二甲基甲酰胺分子加合物的制备和晶体结构[J].有机化学,2004,24(4):419-422. WANG Jian-long,OU Yu-xiang,Lü Lian-ying, et al.Preparation and crystal structure of adduct of aminonitrobenzodifuroxan and N,N-dimethylformamide[J]. Journal of Organic Chemistry,2004,24(4):419-422.
[10] 王亲会. DNTF基熔铸炸药的性能研究[J].火炸药学报,2003,26(3):57-59. WANG Qin-hui. Properties of DNTF-based melt-cast explosives[J]. Chinese Journal of Explosives & Propellants(Huozhayao Xuebao), 2003,26(3):57-59.
[11] 王亲会, 张亦安, 金大勇.DNTF炸药的能量及可熔铸性[J].火炸药学报,2004,27(4):14-16. WANG Qin-hui,ZHANG Yi-an,JIN Da-yong.Energy and castibility of DNTF explosive[J]. Chinese Journal of Explosives & Propellants(Huozhayao Xuebao),2004,27(4):14-16.
[12] 王浩,王亲会,金大勇,等.DNTF基含硼和含铝炸药的水下能量[J].火炸药学报,2007,30(6):38-40. WANG Hao,WANG Qin-hui,JIN Da-yong,et al.Underwater energy of DNTF based boron-contained and aluminum-contained explosive[J]. Chinese Journal of Explosives & Propellants(Huozhayao Xuebao),2007,30(6):38-40.
[13] 蒋秋黎,王浩,罗一鸣,等.TNAZ/DNTF最低共熔物的熔铸性能[J].火工品,2004(3):42-45. JIANG Qiu-li,WANG Hao,LUO Yi-ming,et al.Study on properties of melt-cast explosive of lowest eutectic mixture TNAZ/DNTF[J]. Initiators & Pyrotechnics,2004(3):42-45.
[14] 王浩, 高杰, 罗一鸣, 等. DNTF/HMX炸药金属加速做功能力及其JWL状态方程[J].兵工自动化,2014,33(7):60-62. WANG Hao,GAO Jie,LUO Yi-ming,et al. Metal accelerating ability and JWL EOS of DNTF/HMX explosive[J]. Ordnance Industry Automation, 2014,33(7):60-62.
[15] 王旭朋,罗运军,郭凯,等.含3,3’-二硝基-4,4’-氧化偶氮呋咱推进剂的能量特性研究[J].含能材料,2009,17(1):79-82. WANG Xu-peng,LUO Yun-jun,GUO Kai,et al.Energy characteristics computation of propellant containing 3,3’-dinitro-4,4’-oxazafurazan[J]. Chinese Journal of Energetic Materials,2009,17(1):79-82.
[16] 张腊莹,衡淑云,刘子如,等.PBT与高能氧化剂的相互作用的热分析法研究[J].含能材料,2009,17(6):668-673. ZHANG La-yin,HENG Shu-yun,LIU Zi-ru,et al. Interactions of PBT with some high energy oxidizers by thermal analysis[J]. Chinese Journal of Energetic Materials, 2009,17(6):668-673.
[17] 李玉斌,黄辉,李金山,等.含DAAzF的HMX基低感高能炸药研究[J].含能材料,2008,16(3):244-246. LI Yu-bin,HUANG Hui,LI Jin-shan,et al. HMX-based low-sensitive high explosives containing DAAzF[J]. Chinese Journal of Energetic Materials, 2008,16(3):244-246.
[18] 郑伟,王江宁,周彦水.含DNTF的改性双基推进剂燃烧性能[J].推进技术,2006,27(5):469-472. ZHENG Wei,WANG Jiang-ning,ZHOU Yan-shui. Combustion performance of DNTF-CMDB propellant[J]. Journal of Propulsion Technology,2006,27(5):469-472.
[19] Rashid M A M,Cho S G,Cho T H,et al. Heat of formation predictions of various nitro-substituted zaoles by G4MP2-SFM scheme[J]. Theoretical Chemistry Accounts,2015,134(11):1-11.
[20] 王军,董海山,黄奕刚,等. 3, 4-二氨基呋咱基氧化呋咱的合成及其晶体结构[J].合成化学,2006,14(1):18-22. WANG Jun,DONG Hai-shan,HUANG Yi-gang,et al. Synthesis of 3,4-diaminofurazanofuroxan and its crystal structure[J]. Chinese Journal of Synthetic Chemistry, 2006,14(1):18-22.
[21] 王军,董海山,黄奕刚,等.3, 4-二氨基呋咱基氧化呋咱异构体的合成与表征[J].合成化学, 2006,14(2):131-134. WANG Jun,DONG Hai-shan,HUANG Yi-gang,et al.Synthesis and characterization of 3,4-diaminofurazanofuroxan isomer[J]. Chinese Journal of Synthetic Chemistry,2006,14(2):131-134.
[22] 王军,董海山,黄奕刚,等.3-氨基-4-氨基肟基呋咱500克级合成[J].含能材料,2006,14(1):27-28. WANG Jun,DONG Hai-shan,HUANG Yi-gang,et al. 500 Gram-grade synthesis of 3-amino-4-aminoximinofurazan[J].Chinese Journal of Energetic Materials,2006,14(1):27-28.
[23] 王军,董海山,黄奕刚,等.3-氨基-4-氨基肟基呋咱的合成及其晶体结构[J].合成化学,2006,14(3):234-239. WANG Jun,DONG Hai-shan,HUANG Yi-gang,et al. Synthesis of 3-amino-4-am inoxmi idofurazan and its crystal structure[J]. Chinese Journal of Synthetic Chemistry, 2006,14(3):234-239.
[24] 陈启凡,董明东,张福辰.3-氨基-4-氨基肟基呋咱的绿色合成工艺[J].辽东学院学报(自然科学版),2010,14(4):281-283. CHEN Qi-fan,DONG Ming-dong,ZHANG Fu-chen.Green synthesis of 3-amino-4-aminoximinofurazan[J].Journal of Eastern Liaoning University(Science and Technology), 2010,14(4):281-283.
[25] Lim C H,Kim T K,Kim K H,et al.Synthesis and characterization of bisnitrofurazanofuroxan[J]. Bulletin of the Korean Chemical Society, 2010, 31(5):1400-1402.
[26] 周彦水,周诚,王伯周,等.高收率合成3-氨基-4-偕氨肟基呋咱研究[J].含能材料,2011,19(5):509-512. ZHOU Yan-shui,ZHOU Cheng,WANG Bo-zhou,et al. Synthesis of 3-amino-4-amidoximinofurazan with high yield[J]. Chinese Journal of Energetic Materials,2011,19(5):509-512.
[27] 王军,董海山,黄奕刚,等.3,4-二氨基呋咱基氧化呋咱的合成[J].含能材料,2004,12(增刊):91-94. WANG Jun,DONG Hai-shan,HUANG Yi-gang, et al.Synthesis of 3,4-diaminofurazanofuroxan[J]. Chinese Journal of Energetic Materials, 2004,12(supplement):91-94.
[28] 王军,董海山,黄奕刚,等.3,4-二氨基呋咱基氧化呋咱的制备及晶体结构研究[J].化学学报,2006,64(2):158-162. WANG Jun,DONG Hai-shan,HUANG Yi-gang,et al. Study on the preparation and crystal structure of 3,4-diaminofurazanofuroxan[J]. Acta Chimca Sinica,2006,64(2):158-162.
[29] 周彦水,李建康,黄新萍,等.3,4-双(4’-氨基呋咱基-3’)氧化呋咱的合成及性能[J].火炸药学报,2007,30(1):54-56. ZHOU Yan-shui,LI Jian-kang,HUANG Xin-ping,et al.Synthesis and properties of 3,4-bis(4’-aminofurazano-3’)furoxan[J]. Chinese Journal of Explosives & Propellants(Huozhayao Xuebao),2007,30(1):54-56.
[30] Philip W L,Colin J P,David E C,et al.3,6-Bis(4-nitro-1,2,5-oxadiazol-3-yl)-1,4,2,5-dioxadiazene (BNDD):a powerful sensitive explosive[J]. Synlett,2011(14):2097-2099.
[31] 周彦水,王伯周,李建康,等. 3,4-双(4’-硝基呋咱基-3’)氧化呋咱合成、表征与性能研究[J].化学学报,2011,69(14):1673-1680. ZHOU Yan-shui,WANG Bo-zhou,LI Jian-kang,et al. Study on synthesis,characterization and properties of 3,4-bis(4’-nitrofurazano-3’-yl)furoxan[J]. Acta Chimca Sinica,2011,69(14):1673-1680.
[32] 王军.3,3’-二(3-氨基呋咱基氧化呋咱-4-基)-4,4’-偶氮呋咱的合成与表征[J],含能材料,2008,16(2):238-241. WANG Jun.Synthesis and characterization of 3,3’-bis (3-aminofuroxime-4-yl)-4-4’-diazepoxide[J]. Chinese Journal of Energetic Materials, 2008,16(2):238-241.
[33] 周彦水,王伯周,周诚,等.3,4-双(4’-叠氮基呋咱-3’-基)氧化呋咱合成、表征与晶体结构研究[J].有机化学,2010,30(7):1044-1050. ZHOU Yan-shui,WANG Bo-zhou,ZHOU Cheng,et al.Synthesis,characterization and crystal structure study on 3,4-bis(4’-azidofurazano-3’-yl)furoxan[J]. Chinese Journal of Organic Chemistry,2010,30(7):1044-1050.
[34] Stepanov A I,Dashko D V, Astrat’ev A A. 3,4-Bis(4’-nitrofurazan-3’-yl)furoxan:a melt cast powerful explosive and a valuable building block in 1,2,5-oxadiazole chemistry[J].Central European Journal of Energetic Materials,2012,9(4):329-342.
[35] Stepanov A I,Dashko D V,Astrat’ev A A.3,4-Bis(3-nitrofurazan-4-yl)furoxan with nucleophilic agents[J].Vestnik Kazanskogo Gosudarstvennogo Technologicheskogo Universiteta,2001,21:35-44.
[36] Astrat’ev A A,Dashko D V,Stepanov A I.Unusnal reaction of 3,4-bis(3-nitrofurazan-4-yl)furoxan with ammonia,primary amines and hydrazine[J]. Central European Journal of Energetic Materials,2012,10(4):1087-1094.
[37] Stepanov A I,Astrat’ev A A,Dashko D V,et al.Synthesis of linear and cyclic compounds containing the 3,4-bis(3-furazan-3-yl)furoxan fragment[J].Russian Chemica Bulletin,Internationa Editionl,2012,61(5):1024-1040.
[38] 贾思媛,张海昊,周诚,等. 7H-三呋咱并双呋咱并[3,4-b:3’,4’-f:3",4"-d]氮杂环庚三烯及衍生物的合成与表征[J].有机化学,2015,35(7):851-857. JIA Si-yuan,ZHANG Hai-hao,ZHOU Cheng,et al. Synthesis and characterization of 7H-trifurazano-[3,4-b:3’,4’-f:3",4"-d]azepine and its analogues[J]. Chinese Journal of Organic Chemistry,2010,30(7):1044-1050.
[39] Sheremeteev A B,Alexander N B.An efficient synthesis of hydroxyfurazans[J]. Mendeleev Communication, 1998:238-239.
[40] Sheremetev A B. 3,3’-Bis(1-fluoro-1,1-dinitromethyl)difurazanyl ether[C]//Proceeding of the 29th International ICT Conference. Karlsruhe:ICT,1998:1-13.
[41] Sheremetev A B,Aleksandrova N S,Melnikova T M,et al. Synthesis of difurazanyl ethers from 4,4’-dinitroazoxyfurazan[J].Heteroatom Chemistry,2000, 11(1):48-56.
[42] 范艳洁,王伯周,来蔚鹏,等.3,3’-二氰基二呋咱基醚(FOF-2)的合成、表征及量子化学研究[J].有机化学,2009,29(4):614-620. FAN Yan-jie,WANG Bo-zhou,LAI Wei-peng,et al.Synthesis,characterization and quantum chemistry study on 3,3’-dicyanodifurazanyl ether(FOF-2)[J]. Chinese Journal of Organic Chemistry,2009,29(4):614-620.
[43] Sheremetev A B,Kulagina V O,Batog L V,et al.Furazan derivatives:high energetic materials from diaminofurazan[C]//Proceeding of the 22nd International Pyseminar. Colorado:International Pyrotechnics Society,1996:377-388.
[44] Zelenin A K,Trudell M L. A two step synthesis of diaminofurazan and synthesis of N-monoarylmethyl and N,N’-diarylmethyl derivatives[J]. Journal of Heterocyclic Chemistry,1997,34:1057-1060.
[45] Cannizzo L F,Hamilton R S,HighsmithT K,et al.Furazan-based energetic ingredients, ADA405840/XAB[R].Springfield:NTIS,1999.
[46] 翟连杰,王伯周,霍欢,等.3,3’-二(N-羟基偕胺肟基)二呋咱基醚合成及歧化反应[J].含能材料,2013,21(6):697-701. ZHAI Lian-jie,WANG Bo-zhou,HUO Huan,et al. Synthesis and disproportionation reactions of 3,3’-bis(N-hydroxy amidoxime)difurazanyl ether[J]. Chinese Journal of Energetic Materials, 2013,21(6):697-701.
[47] 王伯周,翟连杰,廉鹏,等.3,3’-二(氟偕二硝基)二呋咱基醚(FOF-13)新法合成[J].含能材料,2014,22(6):884-886. WANG Bo-zhou,ZHAI Lian-jie,LIAN Peng,et al.A novel synthesis of 3,3’-bis(fluorodinitromethyl)difurazanyl ether(FOF-13)[J]. Chinese Journal of Energetic Materials,2014,22(6):884-886.
[48] 周彦水,王伯周,王锡杰,等. 双呋咱并[3,4-b:3’,4’-f]氧化呋咱并[3",4"-d]氧杂环庚三烯的合成[J].含能材料,2012,20(1):137-138. ZHOU Yan-shui,WANG Bo-zhou,WANG Xi-jie,et al. Synthesis of bifurazano[3,4-b:3’,4’-f] furoxano[3",4"-d] oxacyclohetpatriene[J]. Chinese Journal of Energetic Materials,2012,20(1):137-138.
[49] 王锡杰,王伯周,贾思媛,等.三呋咱并氧杂环庚三烯(TFO)合成研究[J].含能材料,2012,20(2):258-259. WANG Xi-jie,WANG Bo-zhou,JIA Si-yuan,et al. Synthesis study of trifurazano oxacyclohetpatriene[J]. Chinese Journal of Energetic Materials,2012,20(2):258-259.
[50] 范艳洁,王伯周,周彦水,等.3,3’-二氰基-4,4’-偶氮呋咱(DCAF)合成及晶体结构[J].含能材料,2009,17(4):385-388. FAN Yan-jie,WANG Bo-zhou,ZHOU Yan-shui,et al. Synthesis and crystal structure of 3,3’-dicyano-4,4’-azofurazan(DCAF)[J]. Chinese Journal of Energetic Materials,2009,17(4):385-388.
[51] 李辉,王伯周,于倩倩,等. 3,3’-二(四唑-5-基)二呋咱基醚的合成与表征[J].含能材料,2012,20(1):18-21. LI Hui,WANG Bo-zhou,YU Qian-qian,et al. Synthesis and characterization of 3,3’-bis(tetrazol-5-y1)difurazanyl ether[J].Chinese Journal of Energetic Materials,2012,20(1):18-21.
[52] 高莉,杨红伟,伍波,等.五种呋咱衍生物的新法合成[J].含能材料,2013,21(2):226-229. GAO Li,YANG Hong-wei,WU Bo,et al. New synthetic route of five furazan derivatives[J]. Chinese Journal of Energetic Materials,2013,21(2):226-229.
[53] 李辉,于倩倩,王伯周,等. 3,3’-二(四唑-5-基)-4,4’-偶氮呋咱及其含能离子盐的合成及热性能[J].含能材料,2013,21(6):821-824. LI Hui,YU Qian-qian,WANG Bo-zhou,et al. Synthesis and thermal properties of 3,3’-bis(tetrazol-5-yl)-4,4’-azofurazan and its energetic salts[J]. Chinese Journal of Energetic Materials,2013,21(6):821-824.
[54] Stepanov A I,Sannikov V S,Dashko D V,et al.A new preparative method and some chemical properties of 4-R-furazan-3-carboxylic acid amidrazones[J].Chemistry of Heterocyclic Compounds,2015,51(4):350-360.
[55] Zhang J H,Mitchell L A,Parrish D A,et al.Enforced layer-by-layer stacking of energetic salts towards high performance insensitive energetic materialss[J].Journal of the American Chemical Society,2015,137(33):10532-10535.
[56] HAO Wei,HE Chun-lin,ZHANG Jia-heng,et al. Combination of 1,2,4-oxadiazole and 1,2,5-oxadiazole moieties for the generation of high-performance energetic materials[J].Angewandte Chemie International Edition,2015,54(32):9367-9371.

相似文献/References:

备注/Memo

备注/Memo:
收稿日期:2017-07-31;改回日期:2017-09-24。
基金项目:国家自然科学基金(No.21373157)
作者简介:王彬(1985-),男,硕士,助理研究员,从事含能材料合成及性能研究。E-mail:wangbinyh@163.com
通讯作者:王伯周(1967-),男,博士,研究员,从事含能材料合成及性能研究。E-mail:wangbozhou@163.com
更新日期/Last Update: 1900-01-01