三硝基乙醇及其脂肪族衍生物研究进展
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摘要
三硝基乙醇及其脂肪族衍生物具有含氧量高、密度高等优点,是一类重要的含能材料。综述了三硝基乙醇及其脂肪族衍生物等30余种三硝基乙基类含能化合物的最新研究成果,重点阐述了三硝基乙醇及其脂肪族衍生物的合成、性能及应用研究进展;并结合三硝基乙基类含能化合物的性能特点,进一步探讨了在炸药、固体推进剂等含能材料领域中的应用前景。
2,2,2-Trinitroethanol-based energetic material with high oxygen content and high density is an important category of energetic materials. The latest research advances in 2,2,2-Trinitroethanol(TNE) and its aliphatic derivatives were briefly reviewed, especially including synthesis, performance and application investigation of TNE-based energetic materials. Application prospects of TNE and its derivatives in insensitive high energy explosives and propellants were further investigated.
2,2,2-Trinitroethanol-based energetic material with high oxygen content and high density is an important category of energetic materials. The latest research advances in 2,2,2-Trinitroethanol(TNE) and its aliphatic derivatives were briefly reviewed, especially including synthesis, performance and application investigation of TNE-based energetic materials. Application prospects of TNE and its derivatives in insensitive high energy explosives and propellants were further investigated.
引文
[1] G?BEL M, KLAP?TKE T M. Development and testing of energetic materials: the concept of high densities based on the trinitroethyl functionality[J]. Advanced Func-tional Materials, 2009, 19(3): 347-365.
[2] KLAP?TKE T M, KRUMM B, MOLL R. Polynitroethyl- and fluorodinitroethyl substituted boron esters[J]. Che-mistry:A European Journal, 2013, 19 (36): 12113-12123.
[3] KLAP?TKE T M, KRUMM B, REST S F,et al. Polynitro containing energetic materials based on carbonyl-diisocyanate and 2,2-dinitropropane-1,3-diol[J]. Jounal of Inorganic and General Chemistry, 2014, 640(1): 84-92.
[4] KLAP?TKE T M, PIERCEY D G, STIERSTORFER J. Amination of energetic anions: high-performing energetic materials[J]. Dalton Transactions, 2012, 41(31): 9451-9459.
[5] GIDASPOV A A, BAKHAREV V V, KUKUSHKIN I K. Trinitromethylation reactions of chloro-l,3,5-triazines[J]. Russian Chemical Bulletin, 2009, 58(10): 2154-2163.
[6] TANG Y X, ZHANG J H, MITCHELl L A, et al. Taming of 3,4-di(nitramino)furazan[J]. Journal of the American Chemical Society, 2015, 137(51): 15984-15987.
[7] HUANG H F,SHI Y M, LIU Y F, et al. High-oxygen-balance furazan anions: a good choice for high-performance energetic salts[J]. Chemistry:An Asian Journal, 2016, 11(11): 1688-1696.
[8] MATHIEU D. Sensitivity of energetic materials: theoretical relationships to detonation performance and molecular structure[J]. Industrial & Engineering Chemistry Research, 2017, 56(29): 8191-8201.
[9] STARCHENKOV I B, ANDRIANOV V G, MISHNEV A F. The chemistry of furazano-[3,4-b]pyrazine.7:properties of 5,6-diamino- and 5,6-dihydrazino furazano[3,4-b]pyrazine[J]. Chemistry of Heterocyclic Compounds, 1999, 35(4): 499-508.
[10] STARCHENKOV I B, ANDRIANOV V G,MISHNEV A F. The chemistry of furazano-[3,4-b]pyrazine.1:synthesis and thermodynamic appraisal of 4,8-dihydrodifurazano [3,4-b,e]pyrazine and its derivatives[J]. Chemistry of Heterocyclic Compounds, 1997, 33(2): 216-228.
[11] ROMANOVA T V, ZELENOV M P. MEL'NIKOVA S F,et al. Esterification of 1,2,5-oxadiazolylacetic acids with polynitro alcohols[J]. Russian Chemical Bulletin, 2009, 58(10): 2188-2190.
[12] SHEREMETEV A B, YUDIN I L, SUPONITSKY K Y. Ionic liquid-assisted synthesis of trinitroethyl esters[J]. Mendeleev Communications, 2006, 16(5): 264-266.
[13] CHAVEZ D E, SCHULZE M C, PARRISH D A. Synthesis and characterization of N3-(2,2,2-trinitroethyl)-1,2,4-oxadiazole-3,5-diamine[J]. Chemistry of Hete-rocyclic Compounds, 2017, 53(6/7): 737-739.
[14] ZHANG Q H, ZHANG J H, PARRISH D A, et al. Energetic N-trinitroethyl-substituted mono-,di-, and triaminotetrazoles[J].Chemistry:A European Journal, 2013,19(33):11000-11006.
[15] KLAP?TKE T M, KRUMM B, MOLL R, et al. CHNO based molecules containing 2,2,2-trinitroethoxy moieties as possible high energy dense oxidizers[J]. Journal of Inorganic and General Chemistry, 2011, 637(14/15): 2103-2110.
[16] KLAP?TKE T M, LEROUX M, SCHMID P C, et al. Energetic materials based on 5,5'-diamino-4,4'-dinitramino-3,3'-bi-1,2,4-triazole [J]. Chemistry:An Asian Journal, 2016, 11(6): 844-851.
[17] YIN P, ZHANG J H, PARRISH D A, et a1. Energetic N,N'-ethylene-bridged bis(nitropyrazoles): diversified functionalities and properties [J]. Chemistry:A Euro-pean Journal, 2014, 20: 16529-16536.
[18] LI S H, ZHANG W W, WANG Y, et a1. 2,4,6-Tris(2,2,2-trinitroethylamino)-1,3,5-triazine: synthesis, characterization, and energetic properties[J]. Journal of Energetic Materials, 2014, 32(suppl.1): S33-S40.
[19] EPISHINA M A, FINOGENOV A O, KULIKOV A S, et a1. Synthesis and nitration of 3-R-4-(2,2,2-trinitroethyl) aminofuroxans [J]. Russian Chemical Bulletin, 2012, 61(8): 1575-1581.
[20] YIN P, ZHANG J H, HE C L, et a1. Polynitro-substituted pyrazoles and triazoles as potential energetic materials and oxidizers[J]. Journal of Materials Chemistry A, 2014, 2(9): 3200-3208.
[21] YU Q, YANG H W, JU X H, et a1. The synthesis and study of compounds based on 3,4-bis(aminofurazano) furoxan [J]. Chemistry Select, 2017, 2(2): 688-696.
[22] THOTTEMPUDI V, ZHANG J H, HE C L, et a1. Azo substituted 1,2,4-oxadiazoles as insensitive energetic materials [J]. RSC Advances, 2014, 4: 50361-50364.
[23] TANG Y X, SHREEVE J M. Nitroxy/azido-functiona-lized triazoles as potential energetic plasticizers [J]. Chemistry:A European Journal, 2015, 21: 7285-7291.
[24] ZEMAN S, LIU N, JUNGOVá M, et a1. Crystal lattice free volume in a study of initiation reactivity of nitramines: impact sensitivity[J]. Defence Technology, 2018, 14(2): 93-98.
[25] FRANKEL M B. Synthesis and reactions of trinitromethyl compounds[J].Tetrahedron, 1963, 19(Suppl.1): 213-217.
[26] AXTHAMMER Q J, KRUMM B, KLAP?TKE T M, et al. Synthesis of energetic nitrocarbamates from polynitro alcohols and their potential as high energetic oxidizers[J].The Journal of Organic Chemistry, 2015, 80(12): 6329-6335.
[27] MARANS N S, ZELINSIU R P. 2,2,2-Trinitroethanol: preparation and properties[J]. Journal of the American Chemical Society, 1950, 72(11): 5329-5330.
[28] 刘利钊. 硝仿及其衍生物的合成及工艺优化[D]. 南京:南京理工大学, 2016. LIU L Z. Synthesis and process optimization of nitroform and its derivatives[D]. Nanjing:Nanjing University of Science & Technology, 2016.
[29] FEUER H, KUCERA T. Preparation of 2,2,2-trinitroethanol [J]. The Journal of Organic Chemistry, 1960, 25(11): 2069-2070.
[30] HARTMAN P F. Process for production of 2,2,2-trinitroethanol:3041383[P]. 1962-06-26.
[31] EPISHINA M A, OVCHINNIKOV I V, KULIKOV A S, et al. Henry and Mannich reactions of polynitroalkanes in ionic liquids[J].Mendeleev Communications, 2011, 21(1): 21-23.
[32] KON'KOVA T S, MATYUSHIN Yu N. Combined study of thermochemical properties of nitroform and its salts[J]. Russian Chemical Bulletin, 1998, 47(12):2371-2374.
[33] LU H Y, LI J R, YANG D L, et al. A novel synthesis of nitroform by the nitrolysis of cucurbituril[J]. Chinese Chemical Letters, 2015, 26(3): 365-368.
[34] NAZIN G N, MANELIS G B, DUBOVITSKII F I.Thermal decomposition of nitroform and related compounds in the gas phase[J]. Bulletin of the Academy of Sciences of the USSR, Division of the Chemical Sicence,1969, 18(5): 945-948.
[35] YAN C, DING P, YANG H W, et al. New synthetic route of nitroform (NF) from acetylacetone and study of the reaction mechanism[J]. Industrial & Engineering Chemistry Research, 2016, 55(41): 11029-11034.
[36] 刘利钊, 靳昕, 王鹏程, 等. N,N-二(三硝基乙基)硝胺(BTNNA)的合成工艺优化及热性能[J].爆破器材, 2016, 45(3): 47-50.LIU L Z,JIN X, WANG P C, et al. Synthesis improvement and thermal properties of bis(2,2,2-trinitroethyl)-nitramine(BTNNA) [J]. Explosive Materials, 2016, 45(3): 47-50.
[37] 汪惠英, 文亮, 杨红伟, 等. 硝仿肼的合成工艺与晶体结构[J].火炸药学报, 2013, 36(6): 43-46,59. WANG H Y, WEN L, YANG H W, et al.Synthesis technique and crystal structure of HNF[J].Chinese Journal of Explosives and Propellants, 2013, 36(6): 43-46,59.
[38] 毕福强, 王伯周, 许诚, 等. 含能材料中间体硝仿的研究进展[J].化学试剂, 2012, 34(3): 219-223,260. BI F Q, WANG B Z, XU C,et al. Progress of nitroform (NF), an important intermediate in the preparation of energetic materials[J].Chemical Reagents, 2012, 34(3): 219-223,260.
[39] MURRAY J S, LANE P, G?BEL M, et al. Intra-and intermolecular electrostatic interactions and their significance for the structure, acidity, and tautomerization behavior of trinitromethane [J]. The Journal of Chemical Physics, 2009, 130(10): 104304.
[40] G?BEL M, KLAP?TKE T M. 2,2,2-Trinitroethanol [J]. Acta Crystallographica Section C:Structural Chemistry, 2007, 63(9): O562-O564.
[41] HU R Z, ZHAO F Q, GAO H X, et al. The thermal safety and a density functional theoretical study on N,N'-bis[N-(2,2,2-trinitroethyl)-N-nitro]ethylenediamine(BTNEDA)[J]. Chinese Journal of Energetic Materials, 2012, 20(5):505-513.胡荣祖, 赵凤起, 高红旭, 等. N,N'-二[2,2,2-三硝基乙基-N-硝基)]乙二胺的热安全性和密度泛函理论研究[J]. 含能材料, 2012, 20(5):505-513.
[42] HU R Z, YANG D S, GAO S L, et al. Kinetics and mechanism of the exothermic first-stage decomposition reaction of 1,3-bis(2,2,2-trinitroethyl)-1,3-diazacyclopentanone-2[J]. Journal of Hazardous Materials, 2003, 102(2/3): 147-153.
[43] ZHAO H A, HU R Z, YANG D S, et al. Kinetics and mechanism of the exothermic first-stage decomposition reaction for 1,5-dimethyl-2,6-bis(2,2,2-trinitroethyl)-4,8-dinitroglycoluril[J].Thermochimica Acta, 2004, 416(1/2): 1-4.
[44] AXTHAMMER Q J, KLAP?TKE T M, KRUMM B, et al. The energetic nitrocarbamate O2NN(H)CO[OCH2C(NO2)3]derived from phosgene [J]. Journal of Inorganic and General Chemistry, 2014, 640(1): 76-83.
[45] ABD-ELGHANY M, KLAP?TKE T M, ELBEIH A. Thermal behavior and decomposition kinetics of bis(2,2,2- trinitroethyl)-oxalate as a high energy dense oxidizer and its mixture with nitrocellulose [J]. Propellants,Explosives,Pyrotechnics, 2017, 42(12): 1373-1381.
[46] G?BEL M, KLAP?TKE T M. Exceeding the oxygen content of liquid oxygen: bis(2,2,2-trinitroethyl)carbonate [J]. Acta Crystallographica Section C:Structu-ral Chemistry, 2008, 64(2): O58-O60.
[47] KLAP?TKE T M, KRUMM B, SCHERR M, et a1. Facile synthesis and crystal structure of 1,1,1,3-tetranitro-3-azabutane [J]. Journal of Inorganic and General Chemistry, 2008, 634(8): 1244-1246.
[48] KLAP?TKE T M, PIERCEY D G, STIERSTORFER J. Amination of energetic anions: high-performing energetic materials[J]. Dalton Transactions, 2012,41(31): 9451-9459.
[49] KLAP?TKE T M, KRUMM B, SCHARF R. Oxalyl chloride and hydrazide based energetic polynitro derivatives[J]. Eurpean Journal of Inorganic Chemistry, 2016, 19: 3086-3093.
[50] ERMAKOV A S, BULATOV P V, VINOGRAGRADOV D B, et al. Synthesis of new polynitro dicarboxiylic acid esters[J]. Russian Journal of Organic Chemistry, 2004, 40(7):1062-1063.
[51] STEPANOV R S, KRUGLYAKOVA L A, ASTAKHOV A M. Effect of the structure of 2,2,2-Trinitroethyl-N-nitroamines on the rate of their thermal decomposition[J]. Russian Journal of Organic Chemistry, 2001,37(12):1793.
[52] KLAP?TKE T M, KRUMM B, SCHARF R. From amino acids to high-energy dense oxidizers: polynitro materials derived from β-alanine and L-aspartic acid[J]. Journal of Inorganic and General Chemistry, 2016, 642(16): 887-895.
[53] KLAP?TKE T M, KRUMM B, SCHARF R. N-Nitrosarcosine: an economic precursor for the synthesis of new energetic materials [J]. Chemistry:An Asian Journal,2016, 11(21): 3134-3144.
[54] ABD-ELGHANY M, KLAP?TKE T M, ELBEIH A. Investigation of 2,2,2-trinitroethylnitrocarbamate as a high energy dense oxidizer and its mixture with nitrocellulose (thermal behavior and decomposition kinetics)[J]. Journal of Analytical and Applied Pyrolysis, 2017, 128: 397-404.
[2] KLAP?TKE T M, KRUMM B, MOLL R. Polynitroethyl- and fluorodinitroethyl substituted boron esters[J]. Che-mistry:A European Journal, 2013, 19 (36): 12113-12123.
[3] KLAP?TKE T M, KRUMM B, REST S F,et al. Polynitro containing energetic materials based on carbonyl-diisocyanate and 2,2-dinitropropane-1,3-diol[J]. Jounal of Inorganic and General Chemistry, 2014, 640(1): 84-92.
[4] KLAP?TKE T M, PIERCEY D G, STIERSTORFER J. Amination of energetic anions: high-performing energetic materials[J]. Dalton Transactions, 2012, 41(31): 9451-9459.
[5] GIDASPOV A A, BAKHAREV V V, KUKUSHKIN I K. Trinitromethylation reactions of chloro-l,3,5-triazines[J]. Russian Chemical Bulletin, 2009, 58(10): 2154-2163.
[6] TANG Y X, ZHANG J H, MITCHELl L A, et al. Taming of 3,4-di(nitramino)furazan[J]. Journal of the American Chemical Society, 2015, 137(51): 15984-15987.
[7] HUANG H F,SHI Y M, LIU Y F, et al. High-oxygen-balance furazan anions: a good choice for high-performance energetic salts[J]. Chemistry:An Asian Journal, 2016, 11(11): 1688-1696.
[8] MATHIEU D. Sensitivity of energetic materials: theoretical relationships to detonation performance and molecular structure[J]. Industrial & Engineering Chemistry Research, 2017, 56(29): 8191-8201.
[9] STARCHENKOV I B, ANDRIANOV V G, MISHNEV A F. The chemistry of furazano-[3,4-b]pyrazine.7:properties of 5,6-diamino- and 5,6-dihydrazino furazano[3,4-b]pyrazine[J]. Chemistry of Heterocyclic Compounds, 1999, 35(4): 499-508.
[10] STARCHENKOV I B, ANDRIANOV V G,MISHNEV A F. The chemistry of furazano-[3,4-b]pyrazine.1:synthesis and thermodynamic appraisal of 4,8-dihydrodifurazano [3,4-b,e]pyrazine and its derivatives[J]. Chemistry of Heterocyclic Compounds, 1997, 33(2): 216-228.
[11] ROMANOVA T V, ZELENOV M P. MEL'NIKOVA S F,et al. Esterification of 1,2,5-oxadiazolylacetic acids with polynitro alcohols[J]. Russian Chemical Bulletin, 2009, 58(10): 2188-2190.
[12] SHEREMETEV A B, YUDIN I L, SUPONITSKY K Y. Ionic liquid-assisted synthesis of trinitroethyl esters[J]. Mendeleev Communications, 2006, 16(5): 264-266.
[13] CHAVEZ D E, SCHULZE M C, PARRISH D A. Synthesis and characterization of N3-(2,2,2-trinitroethyl)-1,2,4-oxadiazole-3,5-diamine[J]. Chemistry of Hete-rocyclic Compounds, 2017, 53(6/7): 737-739.
[14] ZHANG Q H, ZHANG J H, PARRISH D A, et al. Energetic N-trinitroethyl-substituted mono-,di-, and triaminotetrazoles[J].Chemistry:A European Journal, 2013,19(33):11000-11006.
[15] KLAP?TKE T M, KRUMM B, MOLL R, et al. CHNO based molecules containing 2,2,2-trinitroethoxy moieties as possible high energy dense oxidizers[J]. Journal of Inorganic and General Chemistry, 2011, 637(14/15): 2103-2110.
[16] KLAP?TKE T M, LEROUX M, SCHMID P C, et al. Energetic materials based on 5,5'-diamino-4,4'-dinitramino-3,3'-bi-1,2,4-triazole [J]. Chemistry:An Asian Journal, 2016, 11(6): 844-851.
[17] YIN P, ZHANG J H, PARRISH D A, et a1. Energetic N,N'-ethylene-bridged bis(nitropyrazoles): diversified functionalities and properties [J]. Chemistry:A Euro-pean Journal, 2014, 20: 16529-16536.
[18] LI S H, ZHANG W W, WANG Y, et a1. 2,4,6-Tris(2,2,2-trinitroethylamino)-1,3,5-triazine: synthesis, characterization, and energetic properties[J]. Journal of Energetic Materials, 2014, 32(suppl.1): S33-S40.
[19] EPISHINA M A, FINOGENOV A O, KULIKOV A S, et a1. Synthesis and nitration of 3-R-4-(2,2,2-trinitroethyl) aminofuroxans [J]. Russian Chemical Bulletin, 2012, 61(8): 1575-1581.
[20] YIN P, ZHANG J H, HE C L, et a1. Polynitro-substituted pyrazoles and triazoles as potential energetic materials and oxidizers[J]. Journal of Materials Chemistry A, 2014, 2(9): 3200-3208.
[21] YU Q, YANG H W, JU X H, et a1. The synthesis and study of compounds based on 3,4-bis(aminofurazano) furoxan [J]. Chemistry Select, 2017, 2(2): 688-696.
[22] THOTTEMPUDI V, ZHANG J H, HE C L, et a1. Azo substituted 1,2,4-oxadiazoles as insensitive energetic materials [J]. RSC Advances, 2014, 4: 50361-50364.
[23] TANG Y X, SHREEVE J M. Nitroxy/azido-functiona-lized triazoles as potential energetic plasticizers [J]. Chemistry:A European Journal, 2015, 21: 7285-7291.
[24] ZEMAN S, LIU N, JUNGOVá M, et a1. Crystal lattice free volume in a study of initiation reactivity of nitramines: impact sensitivity[J]. Defence Technology, 2018, 14(2): 93-98.
[25] FRANKEL M B. Synthesis and reactions of trinitromethyl compounds[J].Tetrahedron, 1963, 19(Suppl.1): 213-217.
[26] AXTHAMMER Q J, KRUMM B, KLAP?TKE T M, et al. Synthesis of energetic nitrocarbamates from polynitro alcohols and their potential as high energetic oxidizers[J].The Journal of Organic Chemistry, 2015, 80(12): 6329-6335.
[27] MARANS N S, ZELINSIU R P. 2,2,2-Trinitroethanol: preparation and properties[J]. Journal of the American Chemical Society, 1950, 72(11): 5329-5330.
[28] 刘利钊. 硝仿及其衍生物的合成及工艺优化[D]. 南京:南京理工大学, 2016. LIU L Z. Synthesis and process optimization of nitroform and its derivatives[D]. Nanjing:Nanjing University of Science & Technology, 2016.
[29] FEUER H, KUCERA T. Preparation of 2,2,2-trinitroethanol [J]. The Journal of Organic Chemistry, 1960, 25(11): 2069-2070.
[30] HARTMAN P F. Process for production of 2,2,2-trinitroethanol:3041383[P]. 1962-06-26.
[31] EPISHINA M A, OVCHINNIKOV I V, KULIKOV A S, et al. Henry and Mannich reactions of polynitroalkanes in ionic liquids[J].Mendeleev Communications, 2011, 21(1): 21-23.
[32] KON'KOVA T S, MATYUSHIN Yu N. Combined study of thermochemical properties of nitroform and its salts[J]. Russian Chemical Bulletin, 1998, 47(12):2371-2374.
[33] LU H Y, LI J R, YANG D L, et al. A novel synthesis of nitroform by the nitrolysis of cucurbituril[J]. Chinese Chemical Letters, 2015, 26(3): 365-368.
[34] NAZIN G N, MANELIS G B, DUBOVITSKII F I.Thermal decomposition of nitroform and related compounds in the gas phase[J]. Bulletin of the Academy of Sciences of the USSR, Division of the Chemical Sicence,1969, 18(5): 945-948.
[35] YAN C, DING P, YANG H W, et al. New synthetic route of nitroform (NF) from acetylacetone and study of the reaction mechanism[J]. Industrial & Engineering Chemistry Research, 2016, 55(41): 11029-11034.
[36] 刘利钊, 靳昕, 王鹏程, 等. N,N-二(三硝基乙基)硝胺(BTNNA)的合成工艺优化及热性能[J].爆破器材, 2016, 45(3): 47-50.LIU L Z,JIN X, WANG P C, et al. Synthesis improvement and thermal properties of bis(2,2,2-trinitroethyl)-nitramine(BTNNA) [J]. Explosive Materials, 2016, 45(3): 47-50.
[37] 汪惠英, 文亮, 杨红伟, 等. 硝仿肼的合成工艺与晶体结构[J].火炸药学报, 2013, 36(6): 43-46,59. WANG H Y, WEN L, YANG H W, et al.Synthesis technique and crystal structure of HNF[J].Chinese Journal of Explosives and Propellants, 2013, 36(6): 43-46,59.
[38] 毕福强, 王伯周, 许诚, 等. 含能材料中间体硝仿的研究进展[J].化学试剂, 2012, 34(3): 219-223,260. BI F Q, WANG B Z, XU C,et al. Progress of nitroform (NF), an important intermediate in the preparation of energetic materials[J].Chemical Reagents, 2012, 34(3): 219-223,260.
[39] MURRAY J S, LANE P, G?BEL M, et al. Intra-and intermolecular electrostatic interactions and their significance for the structure, acidity, and tautomerization behavior of trinitromethane [J]. The Journal of Chemical Physics, 2009, 130(10): 104304.
[40] G?BEL M, KLAP?TKE T M. 2,2,2-Trinitroethanol [J]. Acta Crystallographica Section C:Structural Chemistry, 2007, 63(9): O562-O564.
[41] HU R Z, ZHAO F Q, GAO H X, et al. The thermal safety and a density functional theoretical study on N,N'-bis[N-(2,2,2-trinitroethyl)-N-nitro]ethylenediamine(BTNEDA)[J]. Chinese Journal of Energetic Materials, 2012, 20(5):505-513.胡荣祖, 赵凤起, 高红旭, 等. N,N'-二[2,2,2-三硝基乙基-N-硝基)]乙二胺的热安全性和密度泛函理论研究[J]. 含能材料, 2012, 20(5):505-513.
[42] HU R Z, YANG D S, GAO S L, et al. Kinetics and mechanism of the exothermic first-stage decomposition reaction of 1,3-bis(2,2,2-trinitroethyl)-1,3-diazacyclopentanone-2[J]. Journal of Hazardous Materials, 2003, 102(2/3): 147-153.
[43] ZHAO H A, HU R Z, YANG D S, et al. Kinetics and mechanism of the exothermic first-stage decomposition reaction for 1,5-dimethyl-2,6-bis(2,2,2-trinitroethyl)-4,8-dinitroglycoluril[J].Thermochimica Acta, 2004, 416(1/2): 1-4.
[44] AXTHAMMER Q J, KLAP?TKE T M, KRUMM B, et al. The energetic nitrocarbamate O2NN(H)CO[OCH2C(NO2)3]derived from phosgene [J]. Journal of Inorganic and General Chemistry, 2014, 640(1): 76-83.
[45] ABD-ELGHANY M, KLAP?TKE T M, ELBEIH A. Thermal behavior and decomposition kinetics of bis(2,2,2- trinitroethyl)-oxalate as a high energy dense oxidizer and its mixture with nitrocellulose [J]. Propellants,Explosives,Pyrotechnics, 2017, 42(12): 1373-1381.
[46] G?BEL M, KLAP?TKE T M. Exceeding the oxygen content of liquid oxygen: bis(2,2,2-trinitroethyl)carbonate [J]. Acta Crystallographica Section C:Structu-ral Chemistry, 2008, 64(2): O58-O60.
[47] KLAP?TKE T M, KRUMM B, SCHERR M, et a1. Facile synthesis and crystal structure of 1,1,1,3-tetranitro-3-azabutane [J]. Journal of Inorganic and General Chemistry, 2008, 634(8): 1244-1246.
[48] KLAP?TKE T M, PIERCEY D G, STIERSTORFER J. Amination of energetic anions: high-performing energetic materials[J]. Dalton Transactions, 2012,41(31): 9451-9459.
[49] KLAP?TKE T M, KRUMM B, SCHARF R. Oxalyl chloride and hydrazide based energetic polynitro derivatives[J]. Eurpean Journal of Inorganic Chemistry, 2016, 19: 3086-3093.
[50] ERMAKOV A S, BULATOV P V, VINOGRAGRADOV D B, et al. Synthesis of new polynitro dicarboxiylic acid esters[J]. Russian Journal of Organic Chemistry, 2004, 40(7):1062-1063.
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