[1]高耸松,谢兴兵,王元和.多种绿色起爆药的合成方法研究进展[J].爆破器材,2022,51(02):1-10.[doi:10.3969/j.issn.1001-8352.2022.02.001]
　GAO Songsong,XIE Xingbing,WANG Yuanhe.Research Progress on the Synthesis of Various Green Primary Explosives[J].EXPLOSIVE MATERIALS,2022,51(02):1-10.[doi:10.3969/j.issn.1001-8352.2022.02.001]
点击复制

多种绿色起爆药的合成方法研究进展()
分享到：

《爆破器材》[ISSN:1001-8352/CN:32-1163/TJ]

卷:
51
期数:
2022年02
页码:
1-10
栏目:
基础理论
出版日期:
2022-04-06

文章信息/Info

Title:
Research Progress on the Synthesis of Various Green Primary Explosives
文章编号:
5684
作者:
高耸松; 谢兴兵; 王元和
陕西应用物理化学研究所（陕西西安，710061）
Author(s):
GAO Songsong;  XIE Xingbing;  WANG Yuanhe
Shaanxi Applied Physics and Chemistry Research Institute (Shaanxi Xi＇an, 710061)
关键词:
绿色起爆药;  合成;  四唑类起爆药;  呋咱类起爆药
Keywords:
green primary explosive;  synthesis;  tetrazole primary explosive;  furazan primary explosive
分类号:
TQ560.5
DOI:
10.3969/j.issn.1001-8352.2022.02.001
文献标志码:
A
摘要:
起爆药在火工品领域中具有其他含能材料所难以替代的地位。随着环境保护与可持续发展的理念越来越深入人心，研究无污染、安全性好、输出能力强的绿色起爆药对于今后火工品的进一步发展显得尤为重要。绿色起爆药主要分为四唑类、呋咱类和叠氮类。对近年来在合成较有应用前景的绿色起爆药时，所采用的反应路线与方法进行了整理与综述，并对相关反应机理、药剂性能与用途进行了讨论，为该领域的研究与发展提供参考。
Abstract:
Primary explosive, which is difficult to be replaced by other energetic materials, plays a significant role in the field of pyrotechnics. With the awareness of environmental protection and sustainable development becoming more and more supported by the masses, green primary explosives should have the ability to be pollution-free, good security and strong output performance. Therefore, it is particularly important that the study of green primary explosive for the further development of initiating explosive devices in the future. These explosives can be classified into three types, including tetrazoles, furazans and azides. In this paper, reaction routes and methods, which are used in the synthesis of the green primary explosives with promising application in recent years, were reviewed and summarized. Meanwhile, the reaction mechanism, properties and applications of green primary explosives were also discussed, so as to provide references for the research and development of this field.

参考文献/References:

［1］MATYAS R, PACHMAN J. 起爆药学［M］. 张建国, 张至斌, 许彩霞,译. 北京: 北京理工大学出版社, 2016: 3-6.
MATYAS R, PACHMAN J. Primary explosives［M］. ZHANG J G, ZHANG Z B, XU C X, translated.Beijing:Beijing Institute of Technology Press, 2016: 3-6.
［2］ILICH J Z, KERSTETTER J E. Nutrition in bone health revisited: a story beyond calcium［J］. Journal of American College of Nutrition, 2000, 19(6): 715-737.
［3］COUNCIL N. Measuring lead exposure in infants, children, and other sensitive populations［C］// National Research Council (US) Committee on Measuring Leed in Critical Populations. Washingtion, US: The National Academies Press, 2014: 20418.
［4］HUYNH M H V, HISKEY M A, MEYER T J, et al. Green primaries: environmentally friendly energetic complexes［J］. Proceedings of the National Academy of Sciences of the United States of America, 2006, 103(14): 5409-5412.
［5］李靖, 潘永飞, 汪营磊, 等. 绿色起爆药的研究进展［J］. 爆破器材, 2019, 48(4): 1-10.
LI J, PAN Y F, WANG Y L, et al. Research progress of green primary explosive［J］. Explosive Materials, 2019, 48(4): 1-10.
［6］史胜楠, 倪德彬, 庞丛丛, 等. 绿色起爆药2,4,6-三叠氮-1,3,5-三嗪的制备及性能研究［J］. 火工品, 2017 (4): 33-36．
SHI S N, NI D B, PANG C C, et al. Synthesis and characterization of green primary explosive of 2,4,6- triazido-1,3,5-triazine (TAT) ［J］. Initiators ＆ Pyrotechnics, 2017(4): 33-36．
［7］FISCHER D, KLAPOTKE T M, STIERSTORFER J. Synthesis and characterization of guanidinium difluoroiodate, ［C(NH2)3］+［IF2O2］- and its evaluation as an ingredient in agent defeat weapons［J］. Journal of Inorganic and General Chemistry, 2011, 637(6): 660-665.
［8］王小军, 苏强, 张广源, 等. 二叠氮基乙二肟合成及表征［J］. 含能材料, 2014, 22(6): 741-743.
WANG X J, SU Q, ZHANG G Y, et al. Synthesis and characterization of diazidoglyoxime［J］. Chinese Journal of Energetic Materials, 2014, 22(6): 741-743.
［9］FISCHER N, FISCHER D, KLAPOTKE T M, et al. Pushing the limits of energetic materials: the synthesis and characterization of dihydroxylammonium 5,5-bistetrazole-1,1-diolate［J］. Journal of Material Chemistry, 2012, 22(38): 20418-20422.
［10］KLAP-TKE T M, STRIN M, STIERSTORFER J. Salts of 1H-tetrazole-synthesis, characterization and properties［J］. Zeitschrift fur Anorganische und Allgemeine Chemie, 2008, 634(10): 1711-1723.
［11］杨利, 张同来. 新型火工药剂理论与技术［M］. 北京: 北京理工大学出版社，2019: 116-117.
YANG L, ZHANG T L. The theory and technology of new initiating explosives［M］. Beijing: Beijing Institute of Technology Press, 2019: 116-117.
［12］张苏杭, 韩琳, 王新德. 5-氨基四唑及其衍生物的合成和应用综述［J］. 洛阳师范学院学报, 2006, 25(5): 74-78.
ZHANG S H, HAN L, WANG X D. Review of synthesis and application of 5-aminotetrazole and 5-ATZ derivatives［J］. Journal of Luoyang Normal University, 2006, 25(5): 74-78.
［13］CHERNOVA N G, VESELOVSKAYA G I, VIGRAN V K, et al. 5-Amino-tetrazole. Khimicheskaya promcyshlennost［J］. Seriya: Reaktivy Osobo Chistye Veschestva, 1980 (2): 5-8.
［14］MUROTANI M, MURA H, TAKEDA M, et al. Process for producing 5-aminotetrazole:US05594146A［P］. 1997-02-22.
［15］JOO Y H, SHREEVE J M. 1-Substituted 5-aminotetrazoles: syntheses from CNN3 with primary amines［J］. Organic Letters, 2008, 10(20): 4665-4667.
［16］仝辉, 盛涤伦. 近十年单质起爆药的研究进展［C］//2017年第十九届中国科协年会论文集. 长春, 2017: 1-7.
TONG H, SHENG D L. The progress in elemental primary explosive over the past decade［C］//Proceeding of the 19th Annual Conference of China Association for Science and Technology 2017. Changchun, 2017:1-7.
［17］KLAP-TKE T M, STIERSTORFER J. Nitration products of 5-amino-1H-tetrazole and methyl-5-amino-1H?tetrazoles: structures and properties of promising energetic materials［J］. Helvetica Chimica Acta, 2007, 90(11): 2132-2150.
［18］王杰平, 易文斌, 蔡春. 1-甲基-5-硝亚胺基四唑及其盐的合成与表征［J］. 火炸药学报, 2011, 34(6): 1-4.
WANG J P, YI W B, CAI C. Synthesis and characterization of 1-methyl-5-nitroiminotetrazolate and its salts［J］. Chinese Journal of Explosives & Propellants, 2011, 34(6): 1-4.
［19］GEISBERGER G, KLAP-TKE T M, STIERSTORFER J. Copper bis(1-methyl-5-nitriminotetrazolate): a promising new primary explosive［J］. European Journal of Inorganic Chemistry, 2007 (30): 4743-4750.
［20］佟文超, 王士卫, 武碧栋, 等. 新型绿色起爆药硝氨基四唑钙（II）五水化合物的晶体结构［J］. 含能材料, 2013, 21(5): 578-582.
TONG W C, WANG S W, WU B D, et al. Crystal structure of a novel green initiating explosive calcium nitriminotetrazolate pentahydrate［J］. Chinese Journal of Energetic Materials, 2013, 21(5): 578-582.
［21］KLAP-TKE T M, SABAT- C M, WELCH J M. Alkali metal 5nitrotetrazolate salts: prospective replacements for service lead (II) azide in explosive initiators［J］. Dalton Transactions, 2008 (45): 6372-6380.
［22］CHENG G, MEHTA N, OYLER K D. Green primary explosives［C］//2011 International Automn Seminar on Propellant, Explosives and Pyrotechnics. Nanjing, 2011: 949-953.
［23］TALAWAR M B, AGRAWAL A P, ASTHANA S N. Energetic coordination compounds: synthesis, characterization and thermolysis studies on bis-(5-nitro-2H-tetrazolato-N2) tetraammine cobalt (III) perchlorate (BNCP) and its new transition metal (Ni/Cu/Zn) perchlorate analogues［J］. Journal of Hazardous Materials, 2005, 120(1/2/3): 25-35.
［24］SPEAR R J, ELISCHER P P. Studies of stab initiation. Sensitization of lead azide by energetic sensitizers［J］. Australian Journal of Chemistry, 1982, 35(1): 1-13.
［25］GILLIGAN W H, KAMLET M J. Method of preparing the acid copper salt of 5-nitrotetrazole:US 04093623A［P］. 1977-05-05.
［26］FRONABARGER J W, WILLIAMS M D, SANBORN W B. Lead-free primary explosive composition and method of preparation:US 20110108172A1［P］. 2011-05-12.
［27］蒲彦利, 盛涤伦, 朱雅红, 等. 5硝基四唑亚铜的合成与表征［J］. 火工品, 2009(5): 43-45.
PU Y L, SHENG D L, ZHU Y H, et al. Synthesis and characterization of cooper (I) nitrotetrazolate［J］. Initiators ＆ Pyrotechnics, 2009(5): 43-45.
［28］FRONABARGER J W, WILLIAMS M D, SANBORN W B, et al. DBX-1: a lead-free replacement for lead azide［J］. Propellants, Explosives, Pyrotechnics, 2011, 36(6): 541-550.
［29］MEHTA N, OYLER K D, CHENG G. Green replacements for lead-based materials and safe synthesis and characterization of primary explosives［C］//Proceedings of the 38th International Pyrotechnics Seminar. Denver, CO,US, 2012: 433-443.?
［30］HUYNH M H, HISKEY M A, MEYER T J, et al. Green primaries: environmentally friendly energetic complexes［J］. Proceedings of the National Academy of Sciences of the United States of America, 2006, 103(14): 5409-5412.
［31］张光全. 绿色四唑起爆药研究的最新进展［J］. 含能材料, 2011, 19(4): 473-478.
ZHANG G Q. Recent progress in green tetrazoles primary explosives［J］. Chinese Journal of Energetic Materials, 2011, 19(4): 473-478.
［32］朱雅红, 盛涤伦, 王燕兰, 等. 环保起爆药四(5硝基四唑)·二水合铁-化钠的合成和特性［J］. 含能材料, 2012, 20(6): 726-730.
ZHU Y H, SHENG D L, WANG Y L, et al. Synthesis and performances of green primary explosive sodium tetra (5-nitrotetrazolate) diaquate ferrate (II)［J］. Chinese Journal of Energetic Materials, 2012, 20(6): 726-730.
［33］HUYNH M H V, COBUM M D, MEYER T J, et al. Green primary explosives: 5-nitrotetrazolato?N2?ferrate hierarchies［J］. Proceedings of the National Academy of Sciences of the United States of America, 2006, 103(27): 10322-10327.
［34］盛涤伦, 朱雅红, 蒲彦利. 新一代起爆药设计与合成研究进展［J］. 含能材料, 2012, 20(3): 263-272.
SHENG D L, ZHU Y H, PU Y L. Development of a new-generation primary explosives designing and synthesis［J］. Chinese Journal of Energetic Materials, 2012, 20(3): 263-272.
［35］WARNER K F, GRANHOLM R H. Synthesis of insensitive 5,5＇-azotetrazolate salts［J］. Journal of Energetic Materials, 2011, 29(1): 1-6.
［36］高晓敏, 舒远杰, 熊鹰, 等. 可作起爆药的四唑金属含能配合物的合成及性能研究概况［J］. 高分子通报, 2013(3): 99-104.
GAO X M, SHU Y J, XIONG Y, et al. Energetic tetrazole-metal complexes for initiating agent: synthesis and propertis review［J］. Polymer Bulletin, 2013(3): 99-104.
［37］刘晓建, 张慧娟, 林秋汉,等.唑类含能离子化合物的合成研究进展［J］.火炸药学报,2010,33(1):6-10.
LIU X J, ZHANG H J, LIN Q H, et al.Progress of study on the synthesis of azole energetic ionic compounds［J］.Chinese Journal of Explosive & Propellants,2010,33(1): 6-10.
［38］孙艳苓, 颜冬林, 朱顺官, 等. 5,5＇-偶氮四唑锌的合成及表征［J］. 含能材料, 2012, 20(3): 297-301.
SUN Y L, YAN D L, ZHU S G, et al. Synthesis and characterization of zinc 5,5＇-azotetrazolate［J］. Chinese Journal of Energetic Materials, 2012, 20(3): 297-301.
［39］谢兴兵, 朱顺官, 陈鹏源, 等. 二水偶氮四唑四氨合铜(II)的合成及性能［J］. 火炸药学报, 2014, 37(6): 31-34.
XIE X B, ZHU S G, CHEN P Y, et al. Synthesis and performance of tetraamminecopper (II) azo tetrazolate dihydrate［J］. Chinese Journal of Explosive & Propellants, 2014, 37(6): 31-34.
［40］FISCHER N, KLAP-TKE T M, REYMANN M, et al. Nitrogen-rich salts of 1H,1＇-H-5,5＇-bitetrazole-1,1＇diol: energetic materials with high thermal stability［J］. European Journal of Inorgnic Chemistry, 2013, 2013 (12): 2167-2180．
［41］SINDITSKII V P, FILATOV S A, KOLESOV V I, et al. Combustion behavior and physicochemical properties of dihydroxylammonium of 5,5＇-bistetrazole-1,1＇-diolate- (TKX-50)［J］. Thermochimica Acta, 2015, 614: 85-92．
［42］张至斌, 尹磊, 李彤, 等. 新型绿色起爆药1,1＇-二羟基-5,5＇-联四唑钾的晶体结构及性能研究［J］. 含能材料, 2016, 24(12): 1173-1177.
ZHANG Z B, YIN L, LI T, et al. Crystal structure and properties of a novel green initiation explosive dipotassium 5,5＇-bis(tetrazole-1-oxide)［J］. Chinese Journal of Energetic Materials, 2016, 24(12): 1173-1177.
［43］董岩.多氨基多硝基苯并氧化呋咱及其金属配合物的合成与性能研究［D］.南京:南京理工大学,2014: 3.
DONG Y. Research on synthesis and performance of polyamino and polynitro benzofuroxan and their metal complex［D］. Nanjing: Nanjing University of Science ＆ Technology, 2014: 3.
［44］SITZMANN M E, BICHAY M, FRONABARGER J W, et al. Hydroxynitrobenzodifuroxan and its salts［J］. Journal of Heterocyclic Chemistry, 2005, 42(6): 1117-1125.
［45］OTT D G, BENZIGER T M. Preparation of 1,3,5-triamino-2,4,6-trinitrobenzene from 3,5-dichloranisole: US 04952733A［P］. 1990-08-28.
［46］SITZMANN M, BICHAY M, FRONABARGER J W, et al. Preparation, characterization and output testing of the novel primary explosive, bis(furoxano)nitrophenol, potassium salt［C］//31st International Pyrotechnics Seminar. Fort Collins, CO, US, 2004: 729-734.
［47］张裕峰, 盛涤伦, 马凤娥, 等. 新型起爆药双呋咱硝基酚钾盐的研究［J］. 含能材料, 2007, 15(6): 600-603.
ZHANG Y F, SHENG D L, MA F E, et al. New primary explosive bis-furoxano-nitrophenol potassium salt［J］. Chinese Journal of Energetic Materials, 2007, 15(6): 600-603.
［48］FRONABARGER J W, SITZMANN M E. Nitrobenzodifuroxan compounds, including their salts, and methods thereof:US T145016B1［P］. 2006-12-05.
［49］DE HEER A H, BACSA W S, CH-TELAIN A, et al. Aligned carbon nanotube films: production and optical and electronic properties［J］. Science, 1995, 268:845-847.
［50］WAN X G, DONG J M, XING D Y. Symmetry effect on the optical properties of armchair and zigzag nanotubes［J］. Solid State Communications, 1998, 107(12): 791-795.
［51］李洪丽, 郑晓东, 姜俊, 等. 4,6-二硝基苯并氧化呋咱钠盐的合成表征［J］. 化工新型材料, 2014, 42(6): 160-161,164.
LI H L, ZHENG X D, JIANG J, et al. Synthesis and characterization of the sodium of 4,6-dinitrobenzofuroxan［J］. New Chemical Materials, 2014, 42(6): 160-161,164.
［52］WANG S Z, ZHANG T L, YANG L, et al. Synthesis, thermal decomposition and sensitivity study of CsDNBF［J］. Propellants, Explosives, Pyrotechnics, 2007, 32(1): 16-19.
［53］SHINDE P D, MEHILAL M, SALUNKE R B, et al. Some transition metal salts of 4,6-dinitrobenzofuroxan: synthesis characterization and evaluation of their properties［J］. Propellants, Explosives, Pyrotechnics, 2003, 28(2): 77-82.
［54］LI Y F, ZHANG T L, MIAO Y L, et al. A new way to synthesize spherical KDNBF［J］. Chinese Journal of Explosive & Propellants, 2003, 26(3): 53-56.
李玉峰，张同来，苗艳玲，等.制备球形ＫＤＮＢＦ的新方法［J］. 火炸药学报，2003, 26(3): 53-56.
［55］SINDITSKII V P, EGORSHEV V Y, SERUSHKIN V V,et al. Study on combustion of metalderivatives of 4,6-dinitrobenzofuroxan［C］//Theory and Practice of Energetic Materials Vol.4. Beijing: China Science Technology Press, 2001: 69-77.
［56］BROWN N E, KEYES R T. Structure of salts of 4,6-dinitrobenzofuroxan［J］. The Journal of Organic Chemistry, 1965, 30(7):2452-2454.
［57］MEI G C, PICKETT J W. Lead-free nontoxic priming mix:EP 1440958B1 ［P］. 2005-09-14.
［58］FRONABARGER J W, WILLIAMS M D, SANBORN W B, et al. Preparation, characterization and output testing of salts of 7-hydroxy-4,6-dinitrobenzofuroxan［J］. Safe Journal, 2007, 35(1): 14-18.
［59］FRONABARGER J W, WILLIAMS M D, SANBORN W B, et al. KDNP: a lead free replacement for lead styphnate［J］. Propellants, Explosives, Pyrotechnics, 2011, 36(5): 459-470.
［60］FRONABARGER J W, WILLIAMS M D, SANBORN W B, et al.Characterization and output testing of the novel primary explosive,bis(furoxano)nitrophenol,potassium salt［C］//41st AIAA/ASME/SAE/ASEE Joint Propulsion Conference & Exhibit. Tucson,AZ, US, 2005: 1-6.
［61］张诗欣, 盛涤伦, 朱雅红, 等. 4,6-二硝基-7-氧-苯并氧化呋咱钾:水合物（KDNP·H2O）的合成、晶体结构与性能［J］. 含能材料, 2017, 25(9): 732-737.
ZHANG S X, SHENG D L, ZHU Y H, et al. Synthesis, crystal structure and properties of potassium 7-hydroxy-4,6-dinitrobenzofuroxan monohydrate(KDNP·H2O)［J］. Chinese Journal of Energetic Materials, 2017, 25(9): 732-737.

相似文献/References:

[1]李婧①,潘永飞②,汪营磊②,等.绿色起爆药的研究进展[J].爆破器材,2019,48(04):1.[doi:10.3969/j.issn.1001-8352.2019.04.001]
　LI Jing,PAN Yongfei,WANG Yinglie,et al.Research Progress of Green Primary Explosive[J].EXPLOSIVE MATERIALS,2019,48(02):1.[doi:10.3969/j.issn.1001-8352.2019.04.001]

备注/Memo

备注/Memo:
收稿日期：2021-12-07
第一作者：高耸松(1990-)，女，博士，高级工程师，主要从事火工品设计、新型火工药剂研究与应用等。E-mail：gss0803001@sina.com
更新日期/Last Update: 2022-04-06