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2018 | OriginalPaper | Buchkapitel

2. Hexanitrohexaazaisowurtzitane (HNIW, CL-20)

verfasst von : Dabir S. Viswanath, Tushar K. Ghosh, Veera M. Boddu

Erschienen in: Emerging Energetic Materials: Synthesis, Physicochemical, and Detonation Properties

Verlag: Springer Netherlands

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Abstract

Hexanitrohexaazaisowurtzitane, a nitroamine compound, has emerged as an important insensitive energetic material. This caged compound offers several interesting properties. This chapter discusses the properties and more importantly the formulations using CL-20.

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Literatur
1.
Zurück zum Zitat Nielsen AT (1997) Caged polynitramine compound. US Patent 5693794 Nielsen AT (1997) Caged polynitramine compound. US Patent 5693794
2.
Zurück zum Zitat USA Navy Manteca (2004) Report of 2003. Dept of Navy, Fiscal Year 2003 Rpt USA Navy Manteca (2004) Report of 2003. Dept of Navy, Fiscal Year 2003 Rpt
3.
Zurück zum Zitat Nielsen AT, Nissan RA, Vanderah DJ, Coon CL, Gilardi RD, George CF, Lippen-Anderson JF (1990) Polyazapolycyclics by condensation of aldehydes with amines 2 Formation of 2,4,6,8,10,12-Hexabenzyl-2,4,6,8,10,12-hexaazatetra – cyclo [55000] dodecanes from glyoxal and benzylamines. J Org Chem 55(5):1459–1466CrossRef Nielsen AT, Nissan RA, Vanderah DJ, Coon CL, Gilardi RD, George CF, Lippen-Anderson JF (1990) Polyazapolycyclics by condensation of aldehydes with amines 2 Formation of 2,4,6,8,10,12-Hexabenzyl-2,4,6,8,10,12-hexaazatetra – cyclo [55000] dodecanes from glyoxal and benzylamines. J Org Chem 55(5):1459–1466CrossRef
4.
Zurück zum Zitat Crampton MR, Hamid J, Millar R, Ferguson G (1993) Studies of the synthesis, protonation and decomposition of 2,4,6,8,10,12-hexabenzyl-2,4,6,8,10,12-hexaazatetracyclo[55005,903,11]dodecane (HBIW). J Chem Soc Perkin Trans 2(5):923–929CrossRef Crampton MR, Hamid J, Millar R, Ferguson G (1993) Studies of the synthesis, protonation and decomposition of 2,4,6,8,10,12-hexabenzyl-2,4,6,8,10,12-hexaazatetracyclo[55005,903,11]dodecane (HBIW). J Chem Soc Perkin Trans 2(5):923–929CrossRef
5.
Zurück zum Zitat Edwards WW, Wardle RB (1998) Process for making 2,4,6, 8,10,12- hexanitro- 2,4,6,8,10, 12- hexa azatetracyclo 550 0 5,9 0 3,11] –dodecane. EP 1153025 A2 (WO2000052011A2), US Patent 5739325 Edwards WW, Wardle RB (1998) Process for making 2,4,6, 8,10,12- hexanitro- 2,4,6,8,10, 12- hexa azatetracyclo 550 0 5,9 0 3,11] –dodecane. EP 1153025 A2 (WO2000052011A2), US Patent 5739325
6.
Zurück zum Zitat Kodama T (1994) Preparation of hexakis (trimethylsilylethylcarbamyl) hexaazaisowurtzitane. JP06321962A Kodama T (1994) Preparation of hexakis (trimethylsilylethylcarbamyl) hexaazaisowurtzitane. JP06321962A
7.
Zurück zum Zitat Kodama T, Tojo M, Ikeda M (1996) Acylated hexaazaisowurtzitane derivatives and process for producing the same. WO9623792A1 Kodama T, Tojo M, Ikeda M (1996) Acylated hexaazaisowurtzitane derivatives and process for producing the same. WO9623792A1
8.
Zurück zum Zitat Ou Y-x, Xu Y-j, Liu L-h, Zheng F-p, Wang C, Chen J-t (1999) Comparison of acetonitrile process with ethanol process for synthesis of hexabenzylhexaazaisowurtzitane. Hanneng Cailiao 7(4):152–155 Ou Y-x, Xu Y-j, Liu L-h, Zheng F-p, Wang C, Chen J-t (1999) Comparison of acetonitrile process with ethanol process for synthesis of hexabenzylhexaazaisowurtzitane. Hanneng Cailiao 7(4):152–155
9.
Zurück zum Zitat Ou Y, Xu Y, Chen B, Liu L, Wang C (1999) Synthesis of hexanitrohexaazaisowurtzitane from tetraacetyldiformylhexaazaisowurtzitane. Proc Int Pyrotech Semin 26th:406–411 Ou Y, Xu Y, Chen B, Liu L, Wang C (1999) Synthesis of hexanitrohexaazaisowurtzitane from tetraacetyldiformylhexaazaisowurtzitane. Proc Int Pyrotech Semin 26th:406–411
10.
Zurück zum Zitat Ou Y, Meng Z, Liu J (2007) Advance in high energy density compound CL-20-developments of synthesis route and production technologies of CL-20. Huagong Jinzhan 26(6):762–768 Ou Y, Meng Z, Liu J (2007) Advance in high energy density compound CL-20-developments of synthesis route and production technologies of CL-20. Huagong Jinzhan 26(6):762–768
12.
Zurück zum Zitat Wang C, Ou Y-X, Chen B-R (2000) One pot synthesis of hexabenzylhexaazaiso-wurtzitane. Beijing LigongDaxueXuebao 20(4):521–523 Wang C, Ou Y-X, Chen B-R (2000) One pot synthesis of hexabenzylhexaazaiso-wurtzitane. Beijing LigongDaxueXuebao 20(4):521–523
15.
Zurück zum Zitat Hamilton RS, Sanderson AJ, Wardle RB, Warner KF (2000) Studies of the crystallization of CL-20. International Annual Conference of ICT [Institut ChemischeTechnologie], 31st (Energetic Materials), 21/1–21/8 Hamilton RS, Sanderson AJ, Wardle RB, Warner KF (2000) Studies of the crystallization of CL-20. International Annual Conference of ICT [Institut ChemischeTechnologie], 31st (Energetic Materials), 21/1–21/8
16.
Zurück zum Zitat Bellamy AJ (1995) Reductive debenzylation of hexabenzylhexaazaisowurtzitane. Tetrahedron 51(16):4711–4722CrossRef Bellamy AJ (1995) Reductive debenzylation of hexabenzylhexaazaisowurtzitane. Tetrahedron 51(16):4711–4722CrossRef
17.
Zurück zum Zitat Surapaneni R, Damavarapu R, Kumar RA, Dave PR (2000) Process improvements in CL-20 manufacture. International Annual Conference of ICT, 31st (Energetic Materials), 108/1–108/4 Surapaneni R, Damavarapu R, Kumar RA, Dave PR (2000) Process improvements in CL-20 manufacture. International Annual Conference of ICT, 31st (Energetic Materials), 108/1–108/4
18.
Zurück zum Zitat Qian H, Ye Z-W, Lv C-X (2007) Efficient and facile synthesis of hexanitrohexaazaisowurtzitane (HNIW) for high energetic materials. Lett Org Chem 4(7):482–485CrossRef Qian H, Ye Z-W, Lv C-X (2007) Efficient and facile synthesis of hexanitrohexaazaisowurtzitane (HNIW) for high energetic materials. Lett Org Chem 4(7):482–485CrossRef
19.
Zurück zum Zitat Qian H, Chunxu LV, Zhiwen YE (2008) Synthesis of CL-20 by clean nitrating agent dinitrogen pentoxide. J Indian Chem Soc 85(4):434–439 Qian H, Chunxu LV, Zhiwen YE (2008) Synthesis of CL-20 by clean nitrating agent dinitrogen pentoxide. J Indian Chem Soc 85(4):434–439
20.
Zurück zum Zitat Qian H, Ye Z-W, Lu C-X (2008) Synthesis of CL-20 via nitration and nitrolysis of 2,6,8,12-tetraacety l-2,4,6,8,10,12-hexaazaisowurtzitane with N2O5/HNO3. Yingyong Huaxue 25(3):378–380 Qian H, Ye Z-W, Lu C-X (2008) Synthesis of CL-20 via nitration and nitrolysis of 2,6,8,12-tetraacety l-2,4,6,8,10,12-hexaazaisowurtzitane with N2O5/HNO3. Yingyong Huaxue 25(3):378–380
21.
Zurück zum Zitat Song ZW, Yan QL, Li XJ, Qi XF, Lim M (2010) Crystal transition of CL-20 in different solvents. Chin J Energ Mater 6:648–653 Song ZW, Yan QL, Li XJ, Qi XF, Lim M (2010) Crystal transition of CL-20 in different solvents. Chin J Energ Mater 6:648–653
22.
Zurück zum Zitat Gore GM, Sivabalan R, Nair UR, Saikia A, Venugopalan S, Gandhe BR (2007) Synthesis of CL-20: By oxidative debenzylation with cerium (IV) ammonium nitrate (CAN). Indian J Chem, Sect B: Org Chem Incl Med Chem 46B(3):505–508 Gore GM, Sivabalan R, Nair UR, Saikia A, Venugopalan S, Gandhe BR (2007) Synthesis of CL-20: By oxidative debenzylation with cerium (IV) ammonium nitrate (CAN). Indian J Chem, Sect B: Org Chem Incl Med Chem 46B(3):505–508
23.
Zurück zum Zitat Kawabe S, Miya H, Kodama T, Miyake N (2007) Process for the preparation of 1,3,5,7-tetranitro-1,3,5,7-tetraazacyclooctane. US 6297372 B1, EP 0547735 Kawabe S, Miya H, Kodama T, Miyake N (2007) Process for the preparation of 1,3,5,7-tetranitro-1,3,5,7-tetraazacyclooctane. US 6297372 B1, EP 0547735
24.
Zurück zum Zitat Cagnon G, Eck G, Herve G, Jacob G (2007) Method for making new polycyclic polyamides as precursors for energetic polycyclic polynitramine oxidizers. US Patent 7279572 Cagnon G, Eck G, Herve G, Jacob G (2007) Method for making new polycyclic polyamides as precursors for energetic polycyclic polynitramine oxidizers. US Patent 7279572
25.
Zurück zum Zitat Latypov NV, Wellmar U, Goede P, Bellamy AJ (2000) Synthesis and Scale-Up of 2,4,6,8,10,12-Hexanitro-2,4,6,8,10,12-hexaazaisowurtzitane from 2,6,8,12-Tetraacetyl-4,10-dibenzyl-2,4,6,8,10,12- hexaazaisowurtzitane (HNIW, CL-20). Org Proc Res Dev 4(3):156–158CrossRef Latypov NV, Wellmar U, Goede P, Bellamy AJ (2000) Synthesis and Scale-Up of 2,4,6,8,10,12-Hexanitro-2,4,6,8,10,12-hexaazaisowurtzitane from 2,6,8,12-Tetraacetyl-4,10-dibenzyl-2,4,6,8,10,12- hexaazaisowurtzitane (HNIW, CL-20). Org Proc Res Dev 4(3):156–158CrossRef
26.
Zurück zum Zitat Pang S-P, Yu Y-Z, X-Q Zhao () A novel synthetic route to hexanitrohexa- azaisowurtzitane. Propellants, Explosives, Pyrotechnics 30(6):442–444 Pang S-P, Yu Y-Z, X-Q Zhao () A novel synthetic route to hexanitrohexa- azaisowurtzitane. Propellants, Explosives, Pyrotechnics 30(6):442–444
27.
Zurück zum Zitat Chapman RD, Hollins RA (2008) Benzylamine-Free, heavy-metal-free synthesis of CL-20 via hexa(1-propenyl)hexaazaisowurtzitane. J Energ Mater 26(4):246–273CrossRef Chapman RD, Hollins RA (2008) Benzylamine-Free, heavy-metal-free synthesis of CL-20 via hexa(1-propenyl)hexaazaisowurtzitane. J Energ Mater 26(4):246–273CrossRef
28.
Zurück zum Zitat Herve G, Jacob G, Gallo R (2006) Preparation and structure of novel hexaazaisowurtzitane cages. Chem Eur J 12(12):3339–3344CrossRef Herve G, Jacob G, Gallo R (2006) Preparation and structure of novel hexaazaisowurtzitane cages. Chem Eur J 12(12):3339–3344CrossRef
30.
Zurück zum Zitat Lu L, Xu B, Ma Z, Yue H, Mu W, Ou Y (2007) New method for synthesis and crystallizing of HNIW in nitric acid. In: Huang P, Wang Y, Li S (eds) 2007 Science Press, Proc Intl Autumn Seminar on Propellants, Explosives and Pyrotechnics, 7th, Xi’an, China, Oct 23–26, pp 64–65 Lu L, Xu B, Ma Z, Yue H, Mu W, Ou Y (2007) New method for synthesis and crystallizing of HNIW in nitric acid. In: Huang P, Wang Y, Li S (eds) 2007 Science Press, Proc Intl Autumn Seminar on Propellants, Explosives and Pyrotechnics, 7th, Xi’an, China, Oct 23–26, pp 64–65
31.
Zurück zum Zitat Wang J, Li J, An C, Hou C, Xu W, Li X (2012) Study on ultrasound- and spray-assisted precipitation of CL-20. Propellants, Explos, Pyrotech 37(6):670–675CrossRef Wang J, Li J, An C, Hou C, Xu W, Li X (2012) Study on ultrasound- and spray-assisted precipitation of CL-20. Propellants, Explos, Pyrotech 37(6):670–675CrossRef
32.
Zurück zum Zitat van der Heijden AEDM, Bouma RHB (2004) Crystallization and characterization of RDX, HMX, and CL-20. Cryst Growth Des 4(5):999–1007CrossRef van der Heijden AEDM, Bouma RHB (2004) Crystallization and characterization of RDX, HMX, and CL-20. Cryst Growth Des 4(5):999–1007CrossRef
33.
Zurück zum Zitat Bellamy AJ (2003) A simple method for the purification of crude hexanitrohexaazaisowurtzitane (HNIW or CL20). Propellants, Explos, Pyrotech 28(3):145–152CrossRef Bellamy AJ (2003) A simple method for the purification of crude hexanitrohexaazaisowurtzitane (HNIW or CL20). Propellants, Explos, Pyrotech 28(3):145–152CrossRef
34.
Zurück zum Zitat Degirmenbasi N, Peralta-Inga Z, Olgun U, Gocmez H, Kalyon DM (2006) Recrystallization of CL-20 and HNFX from solution for rigorous control of the polymorph type: part II, experimental studies. J Energ Mater 24(2):103–139. doi:10.1080/07370650600672090 CrossRef Degirmenbasi N, Peralta-Inga Z, Olgun U, Gocmez H, Kalyon DM (2006) Recrystallization of CL-20 and HNFX from solution for rigorous control of the polymorph type: part II, experimental studies. J Energ Mater 24(2):103–139. doi:10.​1080/​0737065060067209​0 CrossRef
35.
Zurück zum Zitat Agrawal JP (2011) High Energy Materials. Wiley, Weinheim, Germany Agrawal JP (2011) High Energy Materials. Wiley, Weinheim, Germany
36.
Zurück zum Zitat Nair UR, Sivabalan R, Gore GM, Geetha M, Asthana SN, Singh H (2005) Hexanitrohexaazaisowurtzitane (CL-20) and CL-20-based formulations (Review). Combust Explosion Shock Waves 41:121–132CrossRef Nair UR, Sivabalan R, Gore GM, Geetha M, Asthana SN, Singh H (2005) Hexanitrohexaazaisowurtzitane (CL-20) and CL-20-based formulations (Review). Combust Explosion Shock Waves 41:121–132CrossRef
37.
Zurück zum Zitat Chapman RD, Hollins RA, Groshens TJ, Nissan DA (2006) Benzylamine-Free, heavy-metal-free synthesis of CL-20. SERDP seed Prohect WP-1518 Chapman RD, Hollins RA, Groshens TJ, Nissan DA (2006) Benzylamine-Free, heavy-metal-free synthesis of CL-20. SERDP seed Prohect WP-1518
38.
Zurück zum Zitat Jin S, Shu Q, Chen S, Shi Y (2007) Preparation of e-HNIW by a one-pot method in concentrated nitric acid from tetraacetyldiformylhexaazaisowurtzitane. Propellants, Explos, Pyrotech 32(6):468–471CrossRef Jin S, Shu Q, Chen S, Shi Y (2007) Preparation of e-HNIW by a one-pot method in concentrated nitric acid from tetraacetyldiformylhexaazaisowurtzitane. Propellants, Explos, Pyrotech 32(6):468–471CrossRef
39.
Zurück zum Zitat Duddu R, Dave PR (1999) Processes and Compositions for Nitration of N-Substituted Isowurtzitane Compounds. Paten WO9957104, USA Duddu R, Dave PR (1999) Processes and Compositions for Nitration of N-Substituted Isowurtzitane Compounds. Paten WO9957104, USA
40.
Zurück zum Zitat Wardle RB, Hinshaw JC (2000) Synthesis and reactions of hexaazaisowurtzitane-type compounds in synthesis of hexanitrohexaazaisowurtzitane (HNIW) explosive. In: Cordant Technologies Inc, USA, Division of US Ser No 292 028, pp 8 Wardle RB, Hinshaw JC (2000) Synthesis and reactions of hexaazaisowurtzitane-type compounds in synthesis of hexanitrohexaazaisowurtzitane (HNIW) explosive. In: Cordant Technologies Inc, USA, Division of US Ser No 292 028, pp 8
41.
Zurück zum Zitat Russell TP, Miller PJ, Piermarini GJ, Block S (1992) High-pressure phase transition in γ-hexanitrohexaazaisowurtzitane. J Phys Chem 96(13):5509–5512CrossRef Russell TP, Miller PJ, Piermarini GJ, Block S (1992) High-pressure phase transition in γ-hexanitrohexaazaisowurtzitane. J Phys Chem 96(13):5509–5512CrossRef
42.
Zurück zum Zitat Ciezak JA, Jenkins TA, Liu Z (2007) Evidence for a high-pressure phase transition of ε-2,4,6,8,10,12-hexanitrohexaazaisowurtzitane (CL-20) using vibrational spectroscopy. Propellants, Explos, Pyrotech 32(6):472–477. doi:10.1002/prep200700209 CrossRef Ciezak JA, Jenkins TA, Liu Z (2007) Evidence for a high-pressure phase transition of ε-2,4,6,8,10,12-hexanitrohexaazaisowurtzitane (CL-20) using vibrational spectroscopy. Propellants, Explos, Pyrotech 32(6):472–477. doi:10.​1002/​prep200700209 CrossRef
43.
Zurück zum Zitat Gump JC, Peiris SM (2008) Phase transitions and isothermal equations of state of epsilon hexanitrohexaazaisowurtzitane (CL-20). J Appl Phys 104(8):083509/1–083509/5. doi:10.1063/1.2990066 Gump JC, Peiris SM (2008) Phase transitions and isothermal equations of state of epsilon hexanitrohexaazaisowurtzitane (CL-20). J Appl Phys 104(8):083509/1–083509/5. doi:10.​1063/​1.​2990066
44.
Zurück zum Zitat Turcotte R, Vachon M, Kwok QSM, Wang R, Jones DEG (2005) Thermal study of HNIW (CL-20). Thermochim Acta 433:105–115CrossRef Turcotte R, Vachon M, Kwok QSM, Wang R, Jones DEG (2005) Thermal study of HNIW (CL-20). Thermochim Acta 433:105–115CrossRef
45.
Zurück zum Zitat Ghosh M, Venkatesan V, Sikder AK, Sikder N (2012) Preparation and characterisation of ε-CL-20 by solvent evaporation and precipitation methods. Def Sci J 62(6):390–398CrossRef Ghosh M, Venkatesan V, Sikder AK, Sikder N (2012) Preparation and characterisation of ε-CL-20 by solvent evaporation and precipitation methods. Def Sci J 62(6):390–398CrossRef
46.
Zurück zum Zitat Meents A, Dittrich B, Johnas SKJ, Thome V, Weckert EF (2008) Charge-density studies of energetic materials: CL-20 and FOX-7. Acta Crystallogr B 64(Pt 1):9–42 Meents A, Dittrich B, Johnas SKJ, Thome V, Weckert EF (2008) Charge-density studies of energetic materials: CL-20 and FOX-7. Acta Crystallogr B 64(Pt 1):9–42
47.
Zurück zum Zitat Chen H, Chen S, Li L, Jin S (2008) Quantitative determination of e-phase in polymorphic HNIW using diffraction patterns. Propellants, Explos, Pyrotech 33:467–471CrossRef Chen H, Chen S, Li L, Jin S (2008) Quantitative determination of e-phase in polymorphic HNIW using diffraction patterns. Propellants, Explos, Pyrotech 33:467–471CrossRef
48.
Zurück zum Zitat Cabalo JB, Sausa RC (2005) Explosive residue detection by laser surface photo-fragmentation–fragment detection spectroscopy: II In Situ and Real-time Monitoring of RDX, HMX, CL20, and TNT, by an Improved ion probe. Report ARL-TR-3478 Cabalo JB, Sausa RC (2005) Explosive residue detection by laser surface photo-fragmentation–fragment detection spectroscopy: II In Situ and Real-time Monitoring of RDX, HMX, CL20, and TNT, by an Improved ion probe. Report ARL-TR-3478
49.
Zurück zum Zitat Larson SL, felt DR, Escalon L, JD Davis, Hansen LD (2001) Analysis of CL-20 in environmental matrices water and soil. ERDC/EL TR-01-21 Larson SL, felt DR, Escalon L, JD Davis, Hansen LD (2001) Analysis of CL-20 in environmental matrices water and soil. ERDC/EL TR-01-21
50.
Zurück zum Zitat Liu Y, Chen S, Luo S (2000) HPLC method for analysis of CL-20 in explosive mixture. Huaxue Yanjiu Yu Yingyong 12(4):446–448 Liu Y, Chen S, Luo S (2000) HPLC method for analysis of CL-20 in explosive mixture. Huaxue Yanjiu Yu Yingyong 12(4):446–448
51.
Zurück zum Zitat Monteil-Rivera F, Paquet L, Deschamps S, Balakrishnan VK, Beaulieu C, Hawari J (2004) Physico-chemical measurements of CL-20 for environmental applications Comparison with RDX and HMX. J Chromatogr A 1025(1):125–132. doi:10.1016/jchroma200308060 CrossRef Monteil-Rivera F, Paquet L, Deschamps S, Balakrishnan VK, Beaulieu C, Hawari J (2004) Physico-chemical measurements of CL-20 for environmental applications Comparison with RDX and HMX. J Chromatogr A 1025(1):125–132. doi:10.​1016/​jchroma200308060​ CrossRef
52.
Zurück zum Zitat Anthony JS, Davis EA, Haley MV, Kolakowski JE, Kurnas CW, Phillips CT, Simini M, Kuperman RG, Checkai RT (2004) HPLC determination of hexanitrohexaazaisowurtzitane (CL 20) in soil and aqueous matrices. US Army Res Dev Eng Command Edgewood chem Bio Center, ECBE-TR, p 403 Anthony JS, Davis EA, Haley MV, Kolakowski JE, Kurnas CW, Phillips CT, Simini M, Kuperman RG, Checkai RT (2004) HPLC determination of hexanitrohexaazaisowurtzitane (CL 20) in soil and aqueous matrices. US Army Res Dev Eng Command Edgewood chem Bio Center, ECBE-TR, p 403
53.
Zurück zum Zitat Makarov A, LoBrutto R, Christodoulatos C, Jerkovich A (2009) The use of ultra high-performance liquid chromatography for studying hydrolysis kinetics of CL-20 and related energetic compounds. J Hazard Mater 162(2–3):1034–1040. doi:10.1016/jjhazmat200805157 CrossRef Makarov A, LoBrutto R, Christodoulatos C, Jerkovich A (2009) The use of ultra high-performance liquid chromatography for studying hydrolysis kinetics of CL-20 and related energetic compounds. J Hazard Mater 162(2–3):1034–1040. doi:10.​1016/​jjhazmat20080515​7 CrossRef
54.
Zurück zum Zitat Oehrle SA (1994) Analysis of CL-20 and TNAZ in the presence of other nitroaromatic and nitramine explosives using HPLC with photodiode array (PDA) detection. J Energ Mater 12(4):22–211. doi:10.1080/07370659408018651 Oehrle SA (1994) Analysis of CL-20 and TNAZ in the presence of other nitroaromatic and nitramine explosives using HPLC with photodiode array (PDA) detection. J Energ Mater 12(4):22–211. doi:10.​1080/​0737065940801865​1
55.
Zurück zum Zitat Persson B, Ostmark H, Bergman H (1997) An HPLC method for analysis of HNIW and TNAZ in an explosive mixture. Propellants, Explos, Pyrotech 22(4):238–239CrossRef Persson B, Ostmark H, Bergman H (1997) An HPLC method for analysis of HNIW and TNAZ in an explosive mixture. Propellants, Explos, Pyrotech 22(4):238–239CrossRef
56.
Zurück zum Zitat Agilent Technology, LC/MS Application Note, April 2004 Agilent Technology, LC/MS Application Note, April 2004
57.
Zurück zum Zitat Toghiani RK, Toghiani H, Maloney SW, Boddu VM (2008) Prediction of physicochemical properties of energetic materials. Fluid Phase Equilib 264:86–92CrossRef Toghiani RK, Toghiani H, Maloney SW, Boddu VM (2008) Prediction of physicochemical properties of energetic materials. Fluid Phase Equilib 264:86–92CrossRef
58.
Zurück zum Zitat Qasim MM, Furey J, Fredrickson HL, Szecsody J, McGrath C, Bajpai R (2004) Semiempirical predictions of chemical degradation reaction mechanisms of CL-20 as related to molecular structure. Struct Chem 15(5):493–499. doi:10.1023/B:STUC000003790727898f5 CrossRef Qasim MM, Furey J, Fredrickson HL, Szecsody J, McGrath C, Bajpai R (2004) Semiempirical predictions of chemical degradation reaction mechanisms of CL-20 as related to molecular structure. Struct Chem 15(5):493–499. doi:10.​1023/​B:​STUC000003790727​898f5 CrossRef
59.
Zurück zum Zitat Zeman S, Jalovy Z (2000) Heats of fusion of polynitro derivatives of polyazaisowurtzitane. Thermochim Acta 345(1):31–38CrossRef Zeman S, Jalovy Z (2000) Heats of fusion of polynitro derivatives of polyazaisowurtzitane. Thermochim Acta 345(1):31–38CrossRef
60.
Zurück zum Zitat Jenkins TF, Bartolini C, Ranney TA (2003) Stability of CL-20,TNAZ, HMX, RDX,NG, and PETN in moist, unsaturated soil. ERDC/CRREL TR-03-7 Jenkins TF, Bartolini C, Ranney TA (2003) Stability of CL-20,TNAZ, HMX, RDX,NG, and PETN in moist, unsaturated soil. ERDC/CRREL TR-03-7
61.
Zurück zum Zitat Simpson RL, Urtiew PA, Ornellas DL, Moody GL, Scribner KJ, Hoffmann DM (1997) CL-20 performance exceeds that of HMX and its sensitivity is moderate. Propellants, Explos, Pyrotech 22(5):249–255CrossRef Simpson RL, Urtiew PA, Ornellas DL, Moody GL, Scribner KJ, Hoffmann DM (1997) CL-20 performance exceeds that of HMX and its sensitivity is moderate. Propellants, Explos, Pyrotech 22(5):249–255CrossRef
62.
Zurück zum Zitat Greenlief CM, Ghosh TK, Viswanath DS, Boddu VM (2010) Vapor Pressure of Hexanitrohexaazaisowurtzitane (HNIW, CL-20). Report to Leonard Wood Institute, LWI-101.1, MO, USA Greenlief CM, Ghosh TK, Viswanath DS, Boddu VM (2010) Vapor Pressure of Hexanitrohexaazaisowurtzitane (HNIW, CL-20). Report to Leonard Wood Institute, LWI-101.1, MO, USA
63.
Zurück zum Zitat Sinditskii VP, Egorshev VY, Berezin MV, Serushkin VV, Milekhin YM, Gusev SA, Matveev AA (2003) Combustion characteristics of the high-energy cage hexanitrohexaazaisowurtzitane nitramine. Khim Fiz 22(7):69–74 Sinditskii VP, Egorshev VY, Berezin MV, Serushkin VV, Milekhin YM, Gusev SA, Matveev AA (2003) Combustion characteristics of the high-energy cage hexanitrohexaazaisowurtzitane nitramine. Khim Fiz 22(7):69–74
64.
Zurück zum Zitat Boddu VM, Maloney SW, Toghiani RK, Toghiani H (2010) Prediction of physicochemical properties of energetic materials for identification of treatment technologies for waste streams. U.S. Army Engineer Research and Development Center, ERDC/CERL TR-10-27 Boddu VM, Maloney SW, Toghiani RK, Toghiani H (2010) Prediction of physicochemical properties of energetic materials for identification of treatment technologies for waste streams. U.S. Army Engineer Research and Development Center, ERDC/CERL TR-10-27
65.
Zurück zum Zitat Osmont A, Catoire L, Gökalp I, Yang V (2007) Ab initio quantum chemical predictions of enthalpies of formation, heat capacities, and entropies of gas-phase energetic compounds. Combust Flame 151:262–273CrossRef Osmont A, Catoire L, Gökalp I, Yang V (2007) Ab initio quantum chemical predictions of enthalpies of formation, heat capacities, and entropies of gas-phase energetic compounds. Combust Flame 151:262–273CrossRef
66.
Zurück zum Zitat Karakaya P, Sidhoum M, Christodoulatos C, Nicolich S, Balas W (2005) Aqueous solubility and alkaline hydrolysis of the novel high explosive hexanitrohexaazaisowurtzitane (CL-20). J Hazard Mater 120(1–3):183–191CrossRef Karakaya P, Sidhoum M, Christodoulatos C, Nicolich S, Balas W (2005) Aqueous solubility and alkaline hydrolysis of the novel high explosive hexanitrohexaazaisowurtzitane (CL-20). J Hazard Mater 120(1–3):183–191CrossRef
67.
Zurück zum Zitat von Holtz E, Ornellas D, Foltz MF, Clarkson JE (1994) The solubility of ε-CL-20 in selected materials. Propellants, Explos, Pyrotech 19:206–212CrossRef von Holtz E, Ornellas D, Foltz MF, Clarkson JE (1994) The solubility of ε-CL-20 in selected materials. Propellants, Explos, Pyrotech 19:206–212CrossRef
68.
Zurück zum Zitat Turcotte R, Vachon M, Kwok QSM, Wang R, Jones DEG (2005) Thermal study of HNIW (CL-20). Thermochim Acta 433(1–2):105–115CrossRef Turcotte R, Vachon M, Kwok QSM, Wang R, Jones DEG (2005) Thermal study of HNIW (CL-20). Thermochim Acta 433(1–2):105–115CrossRef
69.
Zurück zum Zitat Highsmith T, Johnston H (2004) Continuous process for preparing alkoxynitroarenes. ALLIANT TECHSYSTEMS INC., MINNESOTA, US 10/338,767, USA Highsmith T, Johnston H (2004) Continuous process for preparing alkoxynitroarenes. ALLIANT TECHSYSTEMS INC., MINNESOTA, US 10/338,767, USA
70.
Zurück zum Zitat Korsounskii BL, Nedel’ko VV, Chuk anov NV, Larikova TS, Volk F (2000) Kinetics of thermal decomposition of hexanitrohexaazaisowurzitane, Russ Chem Bull 49:812–817 Korsounskii BL, Nedel’ko VV, Chuk anov NV, Larikova TS, Volk F (2000) Kinetics of thermal decomposition of hexanitrohexaazaisowurzitane, Russ Chem Bull 49:812–817
71.
Zurück zum Zitat Ding T, Yang H, Zhang Y (2013) Thermal decomposition of CL-20/RDX mixed system. Huaxue Tuijinji Yu Gaofenzi Cailiao 11(6):84–86 Ding T, Yang H, Zhang Y (2013) Thermal decomposition of CL-20/RDX mixed system. Huaxue Tuijinji Yu Gaofenzi Cailiao 11(6):84–86
72.
Zurück zum Zitat Bohn MA (2002) Kinetic description of mass loss data for the assessment of stability, compatibility and aging of energetic components and formulations exemplified with ε-CL20. Propellants, Explos, Pyrotech 27(3):125–135CrossRef Bohn MA (2002) Kinetic description of mass loss data for the assessment of stability, compatibility and aging of energetic components and formulations exemplified with ε-CL20. Propellants, Explos, Pyrotech 27(3):125–135CrossRef
73.
Zurück zum Zitat Qasim MM, Moore B, Taylor L, Honea P, Gorb L, Leszczynski J (2007) Structural characteristics and reactivity relationships of nitroaromatic and nitramine explosives—a review of our computational chemistry and spectroscopic research. Int J Mol Sci 8:1234–1264CrossRef Qasim MM, Moore B, Taylor L, Honea P, Gorb L, Leszczynski J (2007) Structural characteristics and reactivity relationships of nitroaromatic and nitramine explosives—a review of our computational chemistry and spectroscopic research. Int J Mol Sci 8:1234–1264CrossRef
74.
Zurück zum Zitat Pavlov J, Christodoulatos C, Sidhoum M, Nicolich S, Balas W, Koutsospyros A (2007) Hydrolysis of hexanitrohexaazaisowurtzitane (CL-20). J Energ Mater 25(1):1–18 Pavlov J, Christodoulatos C, Sidhoum M, Nicolich S, Balas W, Koutsospyros A (2007) Hydrolysis of hexanitrohexaazaisowurtzitane (CL-20). J Energ Mater 25(1):1–18
75.
Zurück zum Zitat Santiago L, Felt DR, Davis JL (2007) Chemical remediation of an ordnance-related compound: thealkaline hydrolysis of CL-20. ERDC/El TR-07-18 Report Santiago L, Felt DR, Davis JL (2007) Chemical remediation of an ordnance-related compound: thealkaline hydrolysis of CL-20. ERDC/El TR-07-18 Report
76.
Zurück zum Zitat Naik NH, Gore GM, Gandhe BR, Sikder AK (2008) Studies on thermal decomposition mechanism of CL-20 by pyrolysis gas chromatography-mass spectrometry (Py-GC/MS). J Hazard Mater 159(2–3):5–630 Naik NH, Gore GM, Gandhe BR, Sikder AK (2008) Studies on thermal decomposition mechanism of CL-20 by pyrolysis gas chromatography-mass spectrometry (Py-GC/MS). J Hazard Mater 159(2–3):5–630
77.
Zurück zum Zitat Trott S, Nishino SF, Hawari J, Spain JC (2003) Biodegradation of the nitramine explosive CL-20. Appl Environ Microbiol 69(3):1871–1874CrossRef Trott S, Nishino SF, Hawari J, Spain JC (2003) Biodegradation of the nitramine explosive CL-20. Appl Environ Microbiol 69(3):1871–1874CrossRef
78.
Zurück zum Zitat Crocker FH, Indest KJ, Fredrickson HL (2006) Biodegradation of the cyclic nitramine explosives RDX, HMX, and CL-20. Appl Microbiol Biotechnol 73(2):274–290; Fournier D, Monteil-Rivera F, Halasz A, Bhatt M, Hawari J (2006) Degradation of CL-20 by white-rot fungi Chemosphere 63(1):175–181 Crocker FH, Indest KJ, Fredrickson HL (2006) Biodegradation of the cyclic nitramine explosives RDX, HMX, and CL-20. Appl Microbiol Biotechnol 73(2):274–290; Fournier D, Monteil-Rivera F, Halasz A, Bhatt M, Hawari J (2006) Degradation of CL-20 by white-rot fungi Chemosphere 63(1):175–181
79.
Zurück zum Zitat Balakrishnan VK, Monteil-Rivera F, Gautier MA, Hawari J (2004) Sorption and stability of the polycyclic nitramine explosive CL-20 in soil. J Environ Qual 33(4):1362–1368CrossRef Balakrishnan VK, Monteil-Rivera F, Gautier MA, Hawari J (2004) Sorption and stability of the polycyclic nitramine explosive CL-20 in soil. J Environ Qual 33(4):1362–1368CrossRef
80.
Zurück zum Zitat Balakrishnan VK, Monteil-Rivera F, Halasz A, Corbeanu A, Hawari J (2004) Decomposition of the Polycyclic Nitramine Explosive, CL-20, by Fe0. Environ Sci Technol 38(24):6861–6866CrossRef Balakrishnan VK, Monteil-Rivera F, Halasz A, Corbeanu A, Hawari J (2004) Decomposition of the Polycyclic Nitramine Explosive, CL-20, by Fe0. Environ Sci Technol 38(24):6861–6866CrossRef
81.
Zurück zum Zitat Bhushan B, Paquet L, Spain JC, Hawari J (2003) Biotransformation of 2,4,6,8,10,12-hexanitro-2,4,6,8,10,12-hexaazaisowurtzitane (CL-20) by denitrifying Pseudomonas sp strain FA1. Appl Environ Microbiol 69(9):5216–5221CrossRef Bhushan B, Paquet L, Spain JC, Hawari J (2003) Biotransformation of 2,4,6,8,10,12-hexanitro-2,4,6,8,10,12-hexaazaisowurtzitane (CL-20) by denitrifying Pseudomonas sp strain FA1. Appl Environ Microbiol 69(9):5216–5221CrossRef
82.
Zurück zum Zitat Kholod Y, Okovytyy S, Kuramshina G, Qasim M, Gorb L, Leszczynski J (2007) An analysis of stable forms of CL-20: a DFT study of conformational transitions, infrared and Raman spectra. J Mol Struct 843(1–3):14–25CrossRef Kholod Y, Okovytyy S, Kuramshina G, Qasim M, Gorb L, Leszczynski J (2007) An analysis of stable forms of CL-20: a DFT study of conformational transitions, infrared and Raman spectra. J Mol Struct 843(1–3):14–25CrossRef
83.
Zurück zum Zitat Qasim M, Fredrickson H, Honea P, Furey J, Leszcznski J, Okovytyy S, Szecsody J, Kholod Y (2005) Prediction of CL-20 chemical degradation pathways, theoretical and experimental evidence for dependence on competing modes of reaction. SAR QSAR Environ Res 16:495–515CrossRef Qasim M, Fredrickson H, Honea P, Furey J, Leszcznski J, Okovytyy S, Szecsody J, Kholod Y (2005) Prediction of CL-20 chemical degradation pathways, theoretical and experimental evidence for dependence on competing modes of reaction. SAR QSAR Environ Res 16:495–515CrossRef
84.
Zurück zum Zitat Foltz MF (1994) Thermal stability of ε-hexanitrohexaazaisowurtzitane in an Estane formulation. Propellants, Explos, Pyrotech 19(2):63–69CrossRef Foltz MF (1994) Thermal stability of ε-hexanitrohexaazaisowurtzitane in an Estane formulation. Propellants, Explos, Pyrotech 19(2):63–69CrossRef
85.
Zurück zum Zitat Goede P, Latypov NV, Oestmark H (2004) Fourier transform Raman Spectroscopy of the four crystallographic phases of α, β, γ and ε 2,4,6,8,10,12-hexanitro-2,4,6,8,10,12-hexaazatetracyclo[55005,903,11]dodecane (HNIW, CL-20). Propellants, Explos, Pyrotech 29(4):205–208CrossRef Goede P, Latypov NV, Oestmark H (2004) Fourier transform Raman Spectroscopy of the four crystallographic phases of α, β, γ and ε 2,4,6,8,10,12-hexanitro-2,4,6,8,10,12-hexaazatetracyclo[55005,903,11]dodecane (HNIW, CL-20). Propellants, Explos, Pyrotech 29(4):205–208CrossRef
86.
Zurück zum Zitat Ulrich TF (2005) Energetic materials: particle processing and characterization. Wiley, New York Ulrich TF (2005) Energetic materials: particle processing and characterization. Wiley, New York
87.
Zurück zum Zitat Nair UR, Gore GM, Sivabalan R, Satpute RS, Asthana SN, Singh H (2004) Studies on polymer coated CL-20-the most powerful explosive J Polym Mater 21(4):377–382 Nair UR, Gore GM, Sivabalan R, Satpute RS, Asthana SN, Singh H (2004) Studies on polymer coated CL-20-the most powerful explosive J Polym Mater 21(4):377–382
88.
Zurück zum Zitat Nair UR, Sivabalan R, Gore GM, Dudek K, Marecek P, Vavra P (2000) Laboratory testing of HNIW mixtures. Proc. 31st Int Conf ICT, Karlsruhe, June 27–30 (2000), pp 110/1–110/6 Nair UR, Sivabalan R, Gore GM, Dudek K, Marecek P, Vavra P (2000) Laboratory testing of HNIW mixtures. Proc. 31st Int Conf ICT, Karlsruhe, June 27–30 (2000), pp 110/1–110/6
89.
Zurück zum Zitat Mezger MJ, Nicholich SM, Geiss DA et al (1999) Performance and hazard characterzation of CL-20 formulations. In: Proceedings of 30th International Annual Conference of ICT, Karlsruhe, June 29–July 2 (1999), pp. 4/1–4/14 Mezger MJ, Nicholich SM, Geiss DA et al (1999) Performance and hazard characterzation of CL-20 formulations. In: Proceedings of 30th International Annual Conference of ICT, Karlsruhe, June 29–July 2 (1999), pp. 4/1–4/14
90.
Zurück zum Zitat Tian Y, Xu R, Zhou Y, Nie F (2001) Study on formulation of CL-20. In: Procecings of 4th International Autumn Seminar on Propellants, Explos, Pyrotech Shaoxing, China, pp 43–47 Tian Y, Xu R, Zhou Y, Nie F (2001) Study on formulation of CL-20. In: Procecings of 4th International Autumn Seminar on Propellants, Explos, Pyrotech Shaoxing, China, pp 43–47
91.
Zurück zum Zitat Golfier M, Graindorge H, Longevialle Y, Mace H (1998) New energetic molecules and their applications in the energetic materials. In: Proceedings of 29th International Annual Conf. of ICT, Karlsruhe, 30 June–3 July 1998, pp 3/1–3/17 Golfier M, Graindorge H, Longevialle Y, Mace H (1998) New energetic molecules and their applications in the energetic materials. In: Proceedings of 29th International Annual Conf. of ICT, Karlsruhe, 30 June–3 July 1998, pp 3/1–3/17
92.
Zurück zum Zitat Li J, Brill TB (2006) Nanostructured energetic composites of CL-20 and binders synthesized by sol gel methods. Propellants, Explos, Pyrotech 31:61–69CrossRef Li J, Brill TB (2006) Nanostructured energetic composites of CL-20 and binders synthesized by sol gel methods. Propellants, Explos, Pyrotech 31:61–69CrossRef
93.
Zurück zum Zitat Wagstaff DC (2002) Desensitization of energetic materialsby energetic plasticizer, Brit. UK Pat. Appl GB 2374867 A1, 30 October 2002 Wagstaff DC (2002) Desensitization of energetic materialsby energetic plasticizer, Brit. UK Pat. Appl GB 2374867 A1, 30 October 2002
95.
Zurück zum Zitat Weiser V, Eisenreich N, Eckl W, Eisele S, Menke K (2000) Burning behavior of CL-20/GAP and HMX/GAP rocket propellants. In: International Annual Conference on ICT 31st (Energetic Materials), pp 144/141–144/146 Weiser V, Eisenreich N, Eckl W, Eisele S, Menke K (2000) Burning behavior of CL-20/GAP and HMX/GAP rocket propellants. In: International Annual Conference on ICT 31st (Energetic Materials), pp 144/141–144/146
96.
Zurück zum Zitat Nair UR, Gore GM, Sivabalan R, Divekar CN, Asthana SN, Singh H (2004) Studies on advanced CL-20-based composite modified double-base propellants. J Propul Power 20(5):952–955; Thepenier J, Fanblanc G (2001) Acta Austronautica, 38:245 Nair UR, Gore GM, Sivabalan R, Divekar CN, Asthana SN, Singh H (2004) Studies on advanced CL-20-based composite modified double-base propellants. J Propul Power 20(5):952–955; Thepenier J, Fanblanc G (2001) Acta Austronautica, 38:245
97.
Zurück zum Zitat Thepenier J, Fanblanc G (2001) Advanced technologies available for future solid propellant grains. Acta Austronautica 48(5–12):245–255CrossRef Thepenier J, Fanblanc G (2001) Advanced technologies available for future solid propellant grains. Acta Austronautica 48(5–12):245–255CrossRef
98.
Zurück zum Zitat Kuperman RG, Checkai RT, Simini M, Phillips CT, Anthony JS, Kolakowski JE, Kumas CW, Davis EA (2006) U S Army Research, Development and Engineering., ECBC-TR-485 Kuperman RG, Checkai RT, Simini M, Phillips CT, Anthony JS, Kolakowski JE, Kumas CW, Davis EA (2006) U S Army Research, Development and Engineering., ECBC-TR-485
99.
Zurück zum Zitat Kuperman RG, Checkai RT, Simini M, Phillips CT, Anthony JS, Kolakowski JE, Davis EA (2006) Toxicity of emerging energetic soil contaminant CL-20 to potworm Enchytraeus crypticus in freshly amended or weathered and aged treatments. Chemosphere 62(8):1282–1293CrossRef Kuperman RG, Checkai RT, Simini M, Phillips CT, Anthony JS, Kolakowski JE, Davis EA (2006) Toxicity of emerging energetic soil contaminant CL-20 to potworm Enchytraeus crypticus in freshly amended or weathered and aged treatments. Chemosphere 62(8):1282–1293CrossRef
100.
101.
Zurück zum Zitat Aldoshin SM, Aliev ZG, Goncharov TK (2014) Crystal structure of 2,4,6,8,10,12-hexanitro-2,4,6,8,10,12-hexaazaisowurtzitane solvate with ε-caprolactam. J Struct Chem 55(4):709–712. doi:10.1134/S0022476614040179 CrossRef Aldoshin SM, Aliev ZG, Goncharov TK (2014) Crystal structure of 2,4,6,8,10,12-hexanitro-2,4,6,8,10,12-hexaazaisowurtzitane solvate with ε-caprolactam. J Struct Chem 55(4):709–712. doi:10.​1134/​S002247661404017​9 CrossRef
102.
Zurück zum Zitat Aldoshin SM, Aliev ZG, Goncharov TK, Korchagin DV, Milekhin YM, Shishov NI (2011) New conformer of 2,4,6,8,10,12-hexanitro-2,4,6,8,10,12-hexaazaisowurtzitane (CL-20). Crystal and molecular structures of the CL-20 solvate with glyceryl triacetate. Russ Chem Bull 60(7):1394–1400. doi:10.1007/s11172-011-0209-5 Aldoshin SM, Aliev ZG, Goncharov TK, Korchagin DV, Milekhin YM, Shishov NI (2011) New conformer of 2,4,6,8,10,12-hexanitro-2,4,6,8,10,12-hexaazaisowurtzitane (CL-20). Crystal and molecular structures of the CL-20 solvate with glyceryl triacetate. Russ Chem Bull 60(7):1394–1400. doi:10.​1007/​s11172-011-0209-5
103.
Zurück zum Zitat Aldoshin SM et al (2014) Crystal structure of cocrystals 2,4,6,8,10,12-hexanitro-2,4,6,8,10,12-hexaazatetracyclo[5.5.0.05.9.03.11]dodecane with 7H-tris-1,2,5-oxadiazolo(3,4-b:3′,4′-d:3″,4″-f)azepine. J Struct Chem 55(2):327–331. doi:10.1134/S0022476614020206 CrossRef Aldoshin SM et al (2014) Crystal structure of cocrystals 2,4,6,8,10,12-hexanitro-2,4,6,8,10,12-hexaazatetracyclo[5.5.0.05.9.03.11]dodecane with 7H-tris-1,2,5-oxadiazolo(3,4-b:3′,4′-d:3″,4″-f)azepine. J Struct Chem 55(2):327–331. doi:10.​1134/​S002247661402020​6 CrossRef
104.
Zurück zum Zitat Alnemrat S, Hooper JP (2013) Predicting temperature-dependent solid vapor pressures of explosives and related compounds using a quantum mechanical continuum solvation model. J Phys Chem A 117(9):2035–2043. doi:10.1021/jp400164j CrossRef Alnemrat S, Hooper JP (2013) Predicting temperature-dependent solid vapor pressures of explosives and related compounds using a quantum mechanical continuum solvation model. J Phys Chem A 117(9):2035–2043. doi:10.​1021/​jp400164j CrossRef
105.
Zurück zum Zitat Alnemrat S, Hooper JP (2014) Predicting solubility of military, homemade, and green explosives in pure and saline water using COSMO-RS. Propellants, Explos, Pyrotech 39(1):79–89. doi:10.1002/prep.201300071 CrossRef Alnemrat S, Hooper JP (2014) Predicting solubility of military, homemade, and green explosives in pure and saline water using COSMO-RS. Propellants, Explos, Pyrotech 39(1):79–89. doi:10.​1002/​prep.​201300071 CrossRef
106.
Zurück zum Zitat Ammon HL (2008) Updated atom/functional group and atom_code volume additivity parameters for the calculation of crystal densities of single molecules, organic salts, and multi-fragment materials containing H, C, B, N, O, F, S, P, Cl, Br, and I. Propellants, Explos, Pyrotech 33(2):92–102. doi:10.1002/prep.200700054 CrossRef Ammon HL (2008) Updated atom/functional group and atom_code volume additivity parameters for the calculation of crystal densities of single molecules, organic salts, and multi-fragment materials containing H, C, B, N, O, F, S, P, Cl, Br, and I. Propellants, Explos, Pyrotech 33(2):92–102. doi:10.​1002/​prep.​200700054 CrossRef
107.
Zurück zum Zitat Amwele HR, Papirom P, Chukanhom K, Beamish FHW, Petkam R (2015) Acute and subchronic toxicity of metal complex azo acid dye and anionic surfactant oil on fish Oreochromis niloticus. J Environ Biol 36(1):199–205, 7p Amwele HR, Papirom P, Chukanhom K, Beamish FHW, Petkam R (2015) Acute and subchronic toxicity of metal complex azo acid dye and anionic surfactant oil on fish Oreochromis niloticus. J Environ Biol 36(1):199–205, 7p
108.
Zurück zum Zitat Andelkovic-Lukic M (2000) New high explosive—polycyclic nitramine hexanitrohexaazaisowurtzitane (HNIW, CL-20). Naucno-Teh Pregl 50(6):60–64 Andelkovic-Lukic M (2000) New high explosive—polycyclic nitramine hexanitrohexaazaisowurtzitane (HNIW, CL-20). Naucno-Teh Pregl 50(6):60–64
109.
Zurück zum Zitat Anderson SR, am Ende DJ, Salan JS, Samuels P (2014) Preparation of an energetic-energetic cocrystal using resonant acoustic mixing. Propellants, Explos, Pyrotech 39(5):637–640 doi:10.1002/prep.201400092 Anderson SR, am Ende DJ, Salan JS, Samuels P (2014) Preparation of an energetic-energetic cocrystal using resonant acoustic mixing. Propellants, Explos, Pyrotech 39(5):637–640 doi:10.​1002/​prep.​201400092
110.
Zurück zum Zitat Atwood AI et al (1999) Burning rate of solid propellant ingredients, part 1: pressure and initial temperature effects. J Propul Power 15(6):740–747. doi:10.2514/2.5522 CrossRef Atwood AI et al (1999) Burning rate of solid propellant ingredients, part 1: pressure and initial temperature effects. J Propul Power 15(6):740–747. doi:10.​2514/​2.​5522 CrossRef
112.
Zurück zum Zitat Atwood AI et al (1999) Burning rate of solid propellant ingredients, part 2: determination of burning rate temperature sensitivity. J Propul Power 15(6):748–752. doi:10.2514/2.5523 CrossRef Atwood AI et al (1999) Burning rate of solid propellant ingredients, part 2: determination of burning rate temperature sensitivity. J Propul Power 15(6):748–752. doi:10.​2514/​2.​5523 CrossRef
114.
Zurück zum Zitat Balakrishnan VK, Halasz A, Hawari J (2003) Alkaline Hydrolysis of the cyclic nitramine explosives RDX, HMX, and CL-20: new insights into degradation pathways obtained by the observation of novel intermediates. Environ Sci Technol 37(9):1838–1843. doi:10.1021/es020959h CrossRef Balakrishnan VK, Halasz A, Hawari J (2003) Alkaline Hydrolysis of the cyclic nitramine explosives RDX, HMX, and CL-20: new insights into degradation pathways obtained by the observation of novel intermediates. Environ Sci Technol 37(9):1838–1843. doi:10.​1021/​es020959h CrossRef
115.
Zurück zum Zitat Balakrishnan VK, Monteil-Rivera F, Gautier MA, Hawari J (2004) Sorption and stability of the polycyclic nitramine explosive CL-20 in soil. J Environ Qual 33(4):1362–1368. doi:10.2134/jeq2004.1362 CrossRef Balakrishnan VK, Monteil-Rivera F, Gautier MA, Hawari J (2004) Sorption and stability of the polycyclic nitramine explosive CL-20 in soil. J Environ Qual 33(4):1362–1368. doi:10.​2134/​jeq2004.​1362 CrossRef
116.
Zurück zum Zitat Balakrishnan VK, Monteil-Rivera F, Halasz A, Corbeanu A, Hawari J (2004) Decomposition of the polycyclic nitramine explosive, CL-20, by FeO. Environ Sci Technol 38(24):6861–6866. doi:10.1021/es049423h CrossRef Balakrishnan VK, Monteil-Rivera F, Halasz A, Corbeanu A, Hawari J (2004) Decomposition of the polycyclic nitramine explosive, CL-20, by FeO. Environ Sci Technol 38(24):6861–6866. doi:10.​1021/​es049423h CrossRef
117.
Zurück zum Zitat Bardai G, Sunahara GI, Spear PA, Martel M, Gong P, Hawari J (2005) Effects of dietary administration of CL-20 on Japanese Quail Coturnix coturnix japonica. Arch Environ Contam Toxicol 49(2):215–222. doi:10.1007/s00244-004-0231-9 CrossRef Bardai G, Sunahara GI, Spear PA, Martel M, Gong P, Hawari J (2005) Effects of dietary administration of CL-20 on Japanese Quail Coturnix coturnix japonica. Arch Environ Contam Toxicol 49(2):215–222. doi:10.​1007/​s00244-004-0231-9 CrossRef
118.
Zurück zum Zitat Bardai GK et al (2006) In vitro degradation of hexanitrohexaazaisowurtzitane (CL-20) by cytosolic enzymes of Japanese quail and the rabbit. Environ Toxicol Chem 25(12):3221–3229. doi:10.1897/06-068R.1 CrossRef Bardai GK et al (2006) In vitro degradation of hexanitrohexaazaisowurtzitane (CL-20) by cytosolic enzymes of Japanese quail and the rabbit. Environ Toxicol Chem 25(12):3221–3229. doi:10.​1897/​06-068R.​1 CrossRef
119.
Zurück zum Zitat Bayat Y et al (2013) Synthesis of 2,4,6,8,10,12-Hexanitro-2,4,6,8,10,12-hexaazaisowurtzitane using Melaminium-tris(hydrogensulfate) by a Simple One-pot Nitration Procedure. Propellants, Explos, Pyrotech 38(6):745–747. doi:10.1002/prep.201300034 CrossRef Bayat Y et al (2013) Synthesis of 2,4,6,8,10,12-Hexanitro-2,4,6,8,10,12-hexaazaisowurtzitane using Melaminium-tris(hydrogensulfate) by a Simple One-pot Nitration Procedure. Propellants, Explos, Pyrotech 38(6):745–747. doi:10.​1002/​prep.​201300034 CrossRef
121.
Zurück zum Zitat Bayat Y, Pourmortazavi SM, Ahadi H, Iravani H (2013) Taguchi robust design to optimize supercritical carbon dioxide anti-solvent process for preparation of 2,4,6,8,10,12-hexanitro-2,4,6,8,10,12-hexaazaisowurtzitane nanoparticles. Chem Eng J 230:432–438 doi:10.1016/j.cej.2013.06.100 Bayat Y, Pourmortazavi SM, Ahadi H, Iravani H (2013) Taguchi robust design to optimize supercritical carbon dioxide anti-solvent process for preparation of 2,4,6,8,10,12-hexanitro-2,4,6,8,10,12-hexaazaisowurtzitane nanoparticles. Chem Eng J 230:432–438 doi:10.​1016/​j.​cej.​2013.​06.​100
122.
Zurück zum Zitat Bayat Y, Soleyman R, Zarandi M (2015) Synthesis and characterization of novel 2,4,6,8,10,12-hexanitro-2,4,6,8,10,12-hexaazaisowurtzitane (2,4,6,8,10,12-hexanitro-2,4,6,8,10,12-hexaazatetracyclo dodecane based nanopolymer-bonded explosives by microemulsion. J Mol Liq 206:190–194. doi:10.1016/j.molliq.2015.02.019 CrossRef Bayat Y, Soleyman R, Zarandi M (2015) Synthesis and characterization of novel 2,4,6,8,10,12-hexanitro-2,4,6,8,10,12-hexaazaisowurtzitane (2,4,6,8,10,12-hexanitro-2,4,6,8,10,12-hexaazatetracyclo dodecane based nanopolymer-bonded explosives by microemulsion. J Mol Liq 206:190–194. doi:10.​1016/​j.​molliq.​2015.​02.​019 CrossRef
124.
Zurück zum Zitat Behler KD, Pesce-Rodriguez R, Cabalo J, Sausa R (2013) Infrared spectroscopy and density functional theory of crystalline β-2,4,6,8,10,12-hexanitrohexaaziosowurtzitane (β CL-20) in the region of its C-H stretching vibrations. Spectrochim Acta, Part A 114:708–712. doi:10.1016/j.saa.2013.05.075 CrossRef Behler KD, Pesce-Rodriguez R, Cabalo J, Sausa R (2013) Infrared spectroscopy and density functional theory of crystalline β-2,4,6,8,10,12-hexanitrohexaaziosowurtzitane (β CL-20) in the region of its C-H stretching vibrations. Spectrochim Acta, Part A 114:708–712. doi:10.​1016/​j.​saa.​2013.​05.​075 CrossRef
125.
Zurück zum Zitat Behrens R (2005) Thermal decomposition processes of energetic materials in the condensed phase at low and moderate temperatures. Adv Ser Phys Chem 16(Overviews of Recent Research on Energetic Materials):29–73 Behrens R (2005) Thermal decomposition processes of energetic materials in the condensed phase at low and moderate temperatures. Adv Ser Phys Chem 16(Overviews of Recent Research on Energetic Materials):29–73
127.
128.
Zurück zum Zitat Bhushan B, Halasz A, Thiboutot S, Ampleman G, Hawari J (2004) Chemotaxis-mediated biodegradation of cyclic nitramine explosives RDX, HMX, and CL-20 by Clostridium sp. EDB2. Biochem Biophys Res Commun 316(3):816–821. doi:10.1016/j.bbrc.2004.02.120 CrossRef Bhushan B, Halasz A, Thiboutot S, Ampleman G, Hawari J (2004) Chemotaxis-mediated biodegradation of cyclic nitramine explosives RDX, HMX, and CL-20 by Clostridium sp. EDB2. Biochem Biophys Res Commun 316(3):816–821. doi:10.​1016/​j.​bbrc.​2004.​02.​120 CrossRef
129.
Zurück zum Zitat Bolton O, Simke LR, Pagoria PF, Matzger AJ (2012) High power explosive with good sensitivity: A 2:1 cocrystal of CL-20:HMX. Cryst Growth Des 12(9):4311–4314. doi:10.1021/cg3010882 CrossRef Bolton O, Simke LR, Pagoria PF, Matzger AJ (2012) High power explosive with good sensitivity: A 2:1 cocrystal of CL-20:HMX. Cryst Growth Des 12(9):4311–4314. doi:10.​1021/​cg3010882 CrossRef
130.
Zurück zum Zitat Bonin PML, Bejan D, Radovic-Hrapovic Z, Halasz A, Hawari J, Bunce NJ (2005) Indirect oxidation of RDX, HMX, and CL-20 cyclic nitramines in aqueous solution at boron-doped diamond electrodes. Environ Chem 2(2):125–129. doi:10.1071/EN05006 CrossRef Bonin PML, Bejan D, Radovic-Hrapovic Z, Halasz A, Hawari J, Bunce NJ (2005) Indirect oxidation of RDX, HMX, and CL-20 cyclic nitramines in aqueous solution at boron-doped diamond electrodes. Environ Chem 2(2):125–129. doi:10.​1071/​EN05006 CrossRef
131.
Zurück zum Zitat Boudreau AE, Hoatson DM (2004) Halogen variations in the paleoproterozoic layered mafic-ultramafic intrusions of East Kimberley, Western Australia: implications for platinum group element mineralization. Econ Geol 99(5):1015–1026CrossRef Boudreau AE, Hoatson DM (2004) Halogen variations in the paleoproterozoic layered mafic-ultramafic intrusions of East Kimberley, Western Australia: implications for platinum group element mineralization. Econ Geol 99(5):1015–1026CrossRef
132.
Zurück zum Zitat Bresler PI (1966) Gas analyzer for determination of chlorine concentrations in gas mixtures. Zavod Lab 32(6):7–766 Bresler PI (1966) Gas analyzer for determination of chlorine concentrations in gas mixtures. Zavod Lab 32(6):7–766
134.
Zurück zum Zitat Byrd EFC, Chabalowski CF, Rice BM (2007) An Ab initio study of nitromethane, HMX, RDX, CL-20, PETN, and TATB. Science Press, pp 696–700 Byrd EFC, Chabalowski CF, Rice BM (2007) An Ab initio study of nitromethane, HMX, RDX, CL-20, PETN, and TATB. Science Press, pp 696–700
135.
Zurück zum Zitat Byrd EFC, Rice BM (2006) Improved prediction of heats of formation of energetic materials using quantum mechanical calculations. J Phys Chem A 110(3):1005–1013CrossRef Byrd EFC, Rice BM (2006) Improved prediction of heats of formation of energetic materials using quantum mechanical calculations. J Phys Chem A 110(3):1005–1013CrossRef
136.
Zurück zum Zitat Byrd EFC, Rice BM (2007) Ab initio study of compressed 1,3,5,7-tetranitro-1,3,5,7-tetraazacyclooctane (HMX), cyclotrimethylenetrinitramine (RDX), 2,4,6,8,10,12-hexanitrohexaazaisowurzitane (CL-20), 2,4,6-trinitro-1,3,5-benzenetriamine (TATB), and pentaerythritol tetranitrate (PETN). J Phys Chem C 111(6):2787–2796. doi:10.1021/jp0617930 CrossRef Byrd EFC, Rice BM (2007) Ab initio study of compressed 1,3,5,7-tetranitro-1,3,5,7-tetraazacyclooctane (HMX), cyclotrimethylenetrinitramine (RDX), 2,4,6,8,10,12-hexanitrohexaazaisowurzitane (CL-20), 2,4,6-trinitro-1,3,5-benzenetriamine (TATB), and pentaerythritol tetranitrate (PETN). J Phys Chem C 111(6):2787–2796. doi:10.​1021/​jp0617930 CrossRef
137.
Zurück zum Zitat Bywater WG, Coleman WR, Kamm O, Merritt HH (1945) Synthetic anticonvulsants. Preparation and properties of some benzoxazoles. J Am Chem Soc 67:7–905. doi:10.1021/ja01222a008 CrossRef Bywater WG, Coleman WR, Kamm O, Merritt HH (1945) Synthetic anticonvulsants. Preparation and properties of some benzoxazoles. J Am Chem Soc 67:7–905. doi:10.​1021/​ja01222a008 CrossRef
138.
140.
Zurück zum Zitat Chan RKS, Anselmo KJ, Reynolds CE, Worman CH (1978) Diffusion of vinyl chloride from PVC packaging material into food simulating solvents. Polym Eng Sci 18(7):6–601. doi:10.1002/pen.760180709 CrossRef Chan RKS, Anselmo KJ, Reynolds CE, Worman CH (1978) Diffusion of vinyl chloride from PVC packaging material into food simulating solvents. Polym Eng Sci 18(7):6–601. doi:10.​1002/​pen.​760180709 CrossRef
141.
Zurück zum Zitat Chang C-L, Lee J-S, Hsu C-K, Shieh B (2001) Thermal decomposition properties of CL-20 and NTO. Proc NATAS Annu Conf Therm Anal Appl 29th:685–690 Chang C-L, Lee J-S, Hsu C-K, Shieh B (2001) Thermal decomposition properties of CL-20 and NTO. Proc NATAS Annu Conf Therm Anal Appl 29th:685–690
143.
Zurück zum Zitat Chernyshev EA, Mironov VF, Petrov AD (1960) New method of preparation of organosilicon monomers by high temperature condensation of alkenyl chlorides, aryl chlorides, and olefins with hydrosilanes. Izv Akad Nauk SSSR, Ser Khim:2147–2156 Chernyshev EA, Mironov VF, Petrov AD (1960) New method of preparation of organosilicon monomers by high temperature condensation of alkenyl chlorides, aryl chlorides, and olefins with hydrosilanes. Izv Akad Nauk SSSR, Ser Khim:2147–2156
145.
Zurück zum Zitat Clawson JS, Anderson KL, Pugmire RJ, Grant DM (2004) 15 N NMR Chemical Shift Tensors of Substituted Hexaazaisowurtzitanes: The Intermediates in the Synthesis of CL-20. J Phys Chem A 108(14):2638–2644. doi:10.1021/jp0373999 CrossRef Clawson JS, Anderson KL, Pugmire RJ, Grant DM (2004) 15 N NMR Chemical Shift Tensors of Substituted Hexaazaisowurtzitanes: The Intermediates in the Synthesis of CL-20. J Phys Chem A 108(14):2638–2644. doi:10.​1021/​jp0373999 CrossRef
146.
Zurück zum Zitat Collet C, Dervaux M, Werschine M (2011) B2514A: a novel enhanced blast explosive. Proc Int Pyrotech Semin 37th(EUROPYRO 2011):72–84 Collet C, Dervaux M, Werschine M (2011) B2514A: a novel enhanced blast explosive. Proc Int Pyrotech Semin 37th(EUROPYRO 2011):72–84
148.
149.
Zurück zum Zitat DeTata D, Collins P, McKinley A (2013) A fast liquid chromatography quadrupole time-of-flight mass spectrometry (LC-QToF-MS) method for the identification of organic explosives and propellants. Forensic Sci Int 233(1–3):63–74. doi:10.1016/j.forsciint.2013.08.007 CrossRef DeTata D, Collins P, McKinley A (2013) A fast liquid chromatography quadrupole time-of-flight mass spectrometry (LC-QToF-MS) method for the identification of organic explosives and propellants. Forensic Sci Int 233(1–3):63–74. doi:10.​1016/​j.​forsciint.​2013.​08.​007 CrossRef
150.
Zurück zum Zitat Divekar CN, Sanghavi RR, Nair UR, Chakraborthy TK, Sikder AK, Singh A (2010) Closed-vessel and thermal studies on triple-base gun propellants containing CL-20. J Propul Power 26(1):120–124. doi:10.2514/1.40895 CrossRef Divekar CN, Sanghavi RR, Nair UR, Chakraborthy TK, Sikder AK, Singh A (2010) Closed-vessel and thermal studies on triple-base gun propellants containing CL-20. J Propul Power 26(1):120–124. doi:10.​2514/​1.​40895 CrossRef
153.
Zurück zum Zitat Dubovik AV, Kozak GD, Aleshkina EA (2007) Theoretical estimation of explosion hazard of NTO, FOX-7, TNAZ, and CL-20. University of Pardubice, pp 484–495 Dubovik AV, Kozak GD, Aleshkina EA (2007) Theoretical estimation of explosion hazard of NTO, FOX-7, TNAZ, and CL-20. University of Pardubice, pp 484–495
154.
Zurück zum Zitat Dumas S, Gauvrit JY, Lanteri P (2012) Determining the polymorphic purity of ε-CL20 contaminated by other polymorphs through the use of FTIR spectroscopy with PLS regression. Propellants, Explos, Pyrotech 37(2):230–234. doi:10.1002/prep.200900090 CrossRef Dumas S, Gauvrit JY, Lanteri P (2012) Determining the polymorphic purity of ε-CL20 contaminated by other polymorphs through the use of FTIR spectroscopy with PLS regression. Propellants, Explos, Pyrotech 37(2):230–234. doi:10.​1002/​prep.​200900090 CrossRef
155.
Zurück zum Zitat Dziura R, Kazimierczuk R, Skupinski W, Pienkowski L, Grzelczyk S (2003) Reductive debenzylation in synthesis of hexanitrohexaazaisowurtzitane (HNIW, CL-20). Organika:31–43 Dziura R, Kazimierczuk R, Skupinski W, Pienkowski L, Grzelczyk S (2003) Reductive debenzylation in synthesis of hexanitrohexaazaisowurtzitane (HNIW, CL-20). Organika:31–43
158.
Zurück zum Zitat Gar KA (1958) Field trials of 65% chlorten. Org Insektofungitsidy i Gerbitsidy:208–230 Gar KA (1958) Field trials of 65% chlorten. Org Insektofungitsidy i Gerbitsidy:208–230
159.
Zurück zum Zitat Geetha M, Nair UR, Sarwade DB, Gore GM, Asthana SN, Singh H (2003) Studies on CL-20: The most powerful high energy material. J Therm Anal Calorim 73(3):913–922CrossRef Geetha M, Nair UR, Sarwade DB, Gore GM, Asthana SN, Singh H (2003) Studies on CL-20: The most powerful high energy material. J Therm Anal Calorim 73(3):913–922CrossRef
160.
Zurück zum Zitat Ghosh M et al (2014) Probing crystal growth of ε- and α-CL-20 polymorphs via metastable phase transition using microscopy and vibrational spectroscopy. Cryst Growth Des 14(10):5053–5063. doi:10.1021/cg500644w CrossRef Ghosh M et al (2014) Probing crystal growth of ε- and α-CL-20 polymorphs via metastable phase transition using microscopy and vibrational spectroscopy. Cryst Growth Des 14(10):5053–5063. doi:10.​1021/​cg500644w CrossRef
161.
Zurück zum Zitat Ghule VD, Jadhav PM, Patil RS, Radhakrishnan S, Soman T (2010) Quantum-chemical studies on hexaazaisowurtzitanes. J Phys Chem A 114(1):498–503. doi:10.1021/jp9071839 CrossRef Ghule VD, Jadhav PM, Patil RS, Radhakrishnan S, Soman T (2010) Quantum-chemical studies on hexaazaisowurtzitanes. J Phys Chem A 114(1):498–503. doi:10.​1021/​jp9071839 CrossRef
162.
Zurück zum Zitat Gnirke AU, Weidle UH (1998) Investigation of prevalence and regulation of expression of progression associated protein (PAP). Anticancer Res 18(6A):4363–4369 Gnirke AU, Weidle UH (1998) Investigation of prevalence and regulation of expression of progression associated protein (PAP). Anticancer Res 18(6A):4363–4369
163.
Zurück zum Zitat Gnirke AU, Weidle UH (1998) Investigation of prevalence and regulation of expression of progression associated protein (PAP). Anticancer Res 18(6A):4363–4369 Gnirke AU, Weidle UH (1998) Investigation of prevalence and regulation of expression of progression associated protein (PAP). Anticancer Res 18(6A):4363–4369
164.
Zurück zum Zitat Goede P, Latypov NV, Oestmark H (2004) Fourier transform Raman Spectroscopy of the four crystallographic phases of α, β, γ and ε 2,4,6,8,10,12-hexanitro-2,4,6,8,10,12-hexaazatetracyclo[5.5.0.05,9.03,11]dodecane (HNIW, CL-20). Propellants, Explos, Pyrotech 29(4):205–208 doi:10.1002/prep.200400047 Goede P, Latypov NV, Oestmark H (2004) Fourier transform Raman Spectroscopy of the four crystallographic phases of α, β, γ and ε 2,4,6,8,10,12-hexanitro-2,4,6,8,10,12-hexaazatetracyclo[5.5.0.05,9.03,11]dodecane (HNIW, CL-20). Propellants, Explos, Pyrotech 29(4):205–208 doi:10.​1002/​prep.​200400047
165.
168.
Zurück zum Zitat Greenberg BL, Kalyon DM, Erol M, Mezger M, Lee K, Lusk S (2003) Analysis of slurry-coating effectiveness of CL-20 using grazing incidence x-ray diffraction. J Energ Mater 21(3):185–199. doi:10.1080/716100383 CrossRef Greenberg BL, Kalyon DM, Erol M, Mezger M, Lee K, Lusk S (2003) Analysis of slurry-coating effectiveness of CL-20 using grazing incidence x-ray diffraction. J Energ Mater 21(3):185–199. doi:10.​1080/​716100383 CrossRef
169.
Zurück zum Zitat Groom CA, Halasz A, Paquet L, D’Cruz P, Hawari J (2003) Cyclodextrin-assisted capillary electrophoresis for determination of the cyclic nitramine explosives RDX, HMX and CL-20. Comparison with high-performance liquid chromatography. J Chromatogr, A 999(1–2):17–22 doi:10.1016/S0021-9673(03)00389-3 Groom CA, Halasz A, Paquet L, D’Cruz P, Hawari J (2003) Cyclodextrin-assisted capillary electrophoresis for determination of the cyclic nitramine explosives RDX, HMX and CL-20. Comparison with high-performance liquid chromatography. J Chromatogr, A 999(1–2):17–22 doi:10.​1016/​S0021-9673(03)00389-3
170.
Zurück zum Zitat Hakansson K, Coorey RV, Zubarev RA, Talrose VL, Hakansson P (2000) Low-mass ions observed in plasma desorption mass spectrometry of high explosives. J Mass Spectrom 35(3):337–346CrossRef Hakansson K, Coorey RV, Zubarev RA, Talrose VL, Hakansson P (2000) Low-mass ions observed in plasma desorption mass spectrometry of high explosives. J Mass Spectrom 35(3):337–346CrossRef
172.
Zurück zum Zitat Hoffmann RW, Sieber W, Guhn G (1965) Decomposition of 1,2,3-benzothiadiazole 1,1-dioxide. Chem Ber 98(11):8–3470CrossRef Hoffmann RW, Sieber W, Guhn G (1965) Decomposition of 1,2,3-benzothiadiazole 1,1-dioxide. Chem Ber 98(11):8–3470CrossRef
174.
Zurück zum Zitat Isayev O, Gorb L, Qasim M, Leszczynski J (2008) Ab initio molecular dynamics study on the initial chemical events in nitramines: thermal decomposition of CL-20. J Phys Chem B 112(35):11005–11013. doi:10.1021/jp804765m CrossRef Isayev O, Gorb L, Qasim M, Leszczynski J (2008) Ab initio molecular dynamics study on the initial chemical events in nitramines: thermal decomposition of CL-20. J Phys Chem B 112(35):11005–11013. doi:10.​1021/​jp804765m CrossRef
175.
Zurück zum Zitat Kaste PJ, Rice BM (2004) Novel energetic materials for the future force: the army pursues the next generation of propellants and explosives. AMPTIAC Q 8(4):85–89 Kaste PJ, Rice BM (2004) Novel energetic materials for the future force: the army pursues the next generation of propellants and explosives. AMPTIAC Q 8(4):85–89
177.
Zurück zum Zitat Kholod Y et al (2006) Are 1,5- and 1,7-dihydrodiimidazo[4,5-b:4’,5’-e]pyrazine the main products of 2,4,6,8,10,12-hexanitro-2,4,6,8,10,12-hexaazaisowurtzitane (CL-20) alkaline hydrolysis? A DFT study of vibrational spectra. J Mol Struct 794(1–3):288–302. doi:10.1016/j.molstruc.2006.02.061 CrossRef Kholod Y et al (2006) Are 1,5- and 1,7-dihydrodiimidazo[4,5-b:4’,5’-e]pyrazine the main products of 2,4,6,8,10,12-hexanitro-2,4,6,8,10,12-hexaazaisowurtzitane (CL-20) alkaline hydrolysis? A DFT study of vibrational spectra. J Mol Struct 794(1–3):288–302. doi:10.​1016/​j.​molstruc.​2006.​02.​061 CrossRef
178.
179.
Zurück zum Zitat Kim J-H, Park Y-C, Yim Y-J, Han J-S (1998) Crystallization behavior of hexanitrohexaazaisowurtzitane at 298 K and quantitative analysis of mixtures of its polymorphs by FTIR. J Chem Eng Jpn 31(3):478–481. doi:10.1252/jcej.31.478 CrossRef Kim J-H, Park Y-C, Yim Y-J, Han J-S (1998) Crystallization behavior of hexanitrohexaazaisowurtzitane at 298 K and quantitative analysis of mixtures of its polymorphs by FTIR. J Chem Eng Jpn 31(3):478–481. doi:10.​1252/​jcej.​31.​478 CrossRef
180.
Zurück zum Zitat Kim J-H, Park Y-C, Yim Y-J, Han J-S (1998) Crystallization behavior of hexanitrohexaazaisowurtzitane at 298 K and quantitative analysis of mixtures of its polymorphs by FTIR. J Chem Eng Jpn 31(3):478–481. doi:10.1252/jcej.31.478 CrossRef Kim J-H, Park Y-C, Yim Y-J, Han J-S (1998) Crystallization behavior of hexanitrohexaazaisowurtzitane at 298 K and quantitative analysis of mixtures of its polymorphs by FTIR. J Chem Eng Jpn 31(3):478–481. doi:10.​1252/​jcej.​31.​478 CrossRef
184.
Zurück zum Zitat Koslik P, Stas J, Wilk Z, Zakrzewski A (2007) Research of high explosives based on RDX, HMX and CL-20 in the small scale underwater test examination. Cent Eur J Energ Mater 4(3):3–13 Koslik P, Stas J, Wilk Z, Zakrzewski A (2007) Research of high explosives based on RDX, HMX and CL-20 in the small scale underwater test examination. Cent Eur J Energ Mater 4(3):3–13
188.
Zurück zum Zitat Lizlovs EA, Bond AP (1975) Effect of low-temperature aging on corrosion resistance of chromium-molybdenum (18Cr-2Mo) titanium-stabilized ferritic stainless steel. J Electrochem Soc 122(5):93–589. doi:10.1149/1.2134271 CrossRef Lizlovs EA, Bond AP (1975) Effect of low-temperature aging on corrosion resistance of chromium-molybdenum (18Cr-2Mo) titanium-stabilized ferritic stainless steel. J Electrochem Soc 122(5):93–589. doi:10.​1149/​1.​2134271 CrossRef
189.
Zurück zum Zitat Maksimowski P, Skupinski W, Szczygielska J (2013) Comparison of the crystals obtained by precipitation of CL-20 with different chemical purity. Propellants, Explos, Pyrotech 38(6):791–797. doi:10.1002/prep.201300064 CrossRef Maksimowski P, Skupinski W, Szczygielska J (2013) Comparison of the crystals obtained by precipitation of CL-20 with different chemical purity. Propellants, Explos, Pyrotech 38(6):791–797. doi:10.​1002/​prep.​201300064 CrossRef
192.
194.
Zurück zum Zitat Molt RW, Bartlett RJ, Watson T, Bazante AP (2012) Conformers of CL-20 explosive and ab initio refinement using perturbation theory: implications to detonation mechanisms. J Phys Chem A 116(49):12129–12135. doi:10.1021/jp305443h CrossRef Molt RW, Bartlett RJ, Watson T, Bazante AP (2012) Conformers of CL-20 explosive and ab initio refinement using perturbation theory: implications to detonation mechanisms. J Phys Chem A 116(49):12129–12135. doi:10.​1021/​jp305443h CrossRef
195.
Zurück zum Zitat Monteil-Rivera F et al (2009) Fate of CL-20 in sandy soils: degradation products as potential markers of natural attenuation. Environ Pollut 157(1):77–85CrossRef Monteil-Rivera F et al (2009) Fate of CL-20 in sandy soils: degradation products as potential markers of natural attenuation. Environ Pollut 157(1):77–85CrossRef
197.
Zurück zum Zitat Namasivayam C, Kanagarathinam A (1992) Distillery wastewater treatment using waste iron(3+)/chromium(3+) hydroxide sludge and polymer flocculants. J Environ Sci Health, Part A A 27(7):37–1721 Namasivayam C, Kanagarathinam A (1992) Distillery wastewater treatment using waste iron(3+)/chromium(3+) hydroxide sludge and polymer flocculants. J Environ Sci Health, Part A A 27(7):37–1721
200.
201.
Zurück zum Zitat Okovytyy S, Kholod Y, Qasim M, Fredrickson H, Leszczynski J (2005) The Mechanism of Unimolecular Decomposition of 2,4,6,8,10,12-Hexanitro-2,4,6,8,10,12-hexaazaisowurtzitane. A computational DFT study. J Phys Chem A 109(12):2964–2970. doi:10.1021/jp045292v CrossRef Okovytyy S, Kholod Y, Qasim M, Fredrickson H, Leszczynski J (2005) The Mechanism of Unimolecular Decomposition of 2,4,6,8,10,12-Hexanitro-2,4,6,8,10,12-hexaazaisowurtzitane. A computational DFT study. J Phys Chem A 109(12):2964–2970. doi:10.​1021/​jp045292v CrossRef
203.
Zurück zum Zitat Paulin A, Jobson BA, Vukcevic S (1981) Chlorination of alumina-containing materials in fluidized bed. Trav Com Int Etude Bauxites, Alumine Alum 16:70–161 Paulin A, Jobson BA, Vukcevic S (1981) Chlorination of alumina-containing materials in fluidized bed. Trav Com Int Etude Bauxites, Alumine Alum 16:70–161
204.
Zurück zum Zitat Peralta-Inga Z, Degirmenbasi N, Olgun U, Gocmez H, Kalyon DM (2006) Recrystallization of CL-20 and HNFX from solution for rigorous control of the polymorph type: part I, mathematical modeling using molecular dynamics method. J Energ Mater 24(2):69–101. doi:10.1080/07370650600672082 CrossRef Peralta-Inga Z, Degirmenbasi N, Olgun U, Gocmez H, Kalyon DM (2006) Recrystallization of CL-20 and HNFX from solution for rigorous control of the polymorph type: part I, mathematical modeling using molecular dynamics method. J Energ Mater 24(2):69–101. doi:10.​1080/​0737065060067208​2 CrossRef
205.
Zurück zum Zitat Pivina T, Korolev V, Khakimov D, Petukhova T, Ivshin V, Lempert D (2012) Computer simulation of decomposition mechanisms for CL-20, hydrazine, and their binary system. Propellants, Explos, Pyrotech 37(4):502–509. doi:10.1002/prep.201100098 CrossRef Pivina T, Korolev V, Khakimov D, Petukhova T, Ivshin V, Lempert D (2012) Computer simulation of decomposition mechanisms for CL-20, hydrazine, and their binary system. Propellants, Explos, Pyrotech 37(4):502–509. doi:10.​1002/​prep.​201100098 CrossRef
207.
Zurück zum Zitat Robidoux PY et al (2004) Acute and chronic toxicity of the new explosive CL-20 to the earthworm (Eisenia andrei) exposed to amended natural soils. Environ Toxicol Chem 23(4):1026–1034. doi:10.1897/03-308 CrossRef Robidoux PY et al (2004) Acute and chronic toxicity of the new explosive CL-20 to the earthworm (Eisenia andrei) exposed to amended natural soils. Environ Toxicol Chem 23(4):1026–1034. doi:10.​1897/​03-308 CrossRef
210.
Zurück zum Zitat Sausa RC, Cabalo JB (2012) The detection of energetic materials by laser photoacoustic overtone spectroscopy. Appl Spectrosc 66(9):993–998. doi:10.1366/12-06699 CrossRef Sausa RC, Cabalo JB (2012) The detection of energetic materials by laser photoacoustic overtone spectroscopy. Appl Spectrosc 66(9):993–998. doi:10.​1366/​12-06699 CrossRef
211.
Zurück zum Zitat Schefflan R, Kovenklioglu S, Kalyon D, Redner P, Heider E (2006) Mathematical model for a fed-batch crystallization process for energetic crystals to achieve targeted size distributions. J Energ Mater 24(2):157–172. doi:10.1080/07370650600672058 CrossRef Schefflan R, Kovenklioglu S, Kalyon D, Redner P, Heider E (2006) Mathematical model for a fed-batch crystallization process for energetic crystals to achieve targeted size distributions. J Energ Mater 24(2):157–172. doi:10.​1080/​0737065060067205​8 CrossRef
212.
Zurück zum Zitat Sikder AK, Sikder N, Gandhe BR, Agrawal JP, Singh H (2002) Hexanitrohexaazaisowurtzitane or CL-20 in India: synthesis and characterisation. Def Sci J 52(2):135–146CrossRef Sikder AK, Sikder N, Gandhe BR, Agrawal JP, Singh H (2002) Hexanitrohexaazaisowurtzitane or CL-20 in India: synthesis and characterisation. Def Sci J 52(2):135–146CrossRef
213.
Zurück zum Zitat Sinditskii VP, Burzhava AV, Sheremetev AB, Aleksandrova NS (2012) Thermal and combustion properties of 3,4-bis(3-nitrofurazan-4-yl)furoxan (DNTF). Propellants, Explos, Pyrotech 37(5):575–580. doi:10.1002/prep.201100095 CrossRef Sinditskii VP, Burzhava AV, Sheremetev AB, Aleksandrova NS (2012) Thermal and combustion properties of 3,4-bis(3-nitrofurazan-4-yl)furoxan (DNTF). Propellants, Explos, Pyrotech 37(5):575–580. doi:10.​1002/​prep.​201100095 CrossRef
215.
Zurück zum Zitat Singh H (2005) Current trend of R&D in the field of high energy materials: an overview. Explosion 15(3):120–132 Singh H (2005) Current trend of R&D in the field of high energy materials: an overview. Explosion 15(3):120–132
216.
218.
Zurück zum Zitat Steinmetz I, Rott L, Boer C (1966) Enrichment of ground waters with surface waters. Hidrobiologia 7:195–201 Steinmetz I, Rott L, Boer C (1966) Enrichment of ground waters with surface waters. Hidrobiologia 7:195–201
219.
Zurück zum Zitat Strigul N, Braida W, Christodoulatos C, Balas W, Nicolich S (2005) The assessment of the energetic compound 2,4,6,8,10,12-hexanitro-2,4,6,8,10,12-hexaazaisowurtzitane (CL-20) degradability in soil. Environ Pollut 139(2):353–361. doi:10.1016/j.envpol.2005.05.002 Strigul N, Braida W, Christodoulatos C, Balas W, Nicolich S (2005) The assessment of the energetic compound 2,4,6,8,10,12-hexanitro-2,4,6,8,10,12-hexaazaisowurtzitane (CL-20) degradability in soil. Environ Pollut 139(2):353–361. doi:10.​1016/​j.​envpol.​2005.​05.​002
220.
Zurück zum Zitat Suzuki J et al (1984) Performance of Shimadzu clinical chemistry analyzer CL-20. Shimadzu Hyoron 41(4):45–229 Suzuki J et al (1984) Performance of Shimadzu clinical chemistry analyzer CL-20. Shimadzu Hyoron 41(4):45–229
222.
Zurück zum Zitat Talawar MB et al (2006) Effect of organic additives on the mitigation of volatility of 1-nitro-3,3’-dinitroazetidine (TNAZ): Next generation powerful melt castable high energy material. J Hazard Mater 134(1–3):8–18. doi:10.1016/j.jhazmat.2003.10.008 CrossRef Talawar MB et al (2006) Effect of organic additives on the mitigation of volatility of 1-nitro-3,3’-dinitroazetidine (TNAZ): Next generation powerful melt castable high energy material. J Hazard Mater 134(1–3):8–18. doi:10.​1016/​j.​jhazmat.​2003.​10.​008 CrossRef
223.
Zurück zum Zitat Talawar MB, Sivabalan R, Polke BG, Nair UR, Gore GM, Asthana SN (2005) Establishment of process technology for the manufacture of dinitrogen pentoxide and its utility for the synthesis of most powerful explosive of today—CL-20. J Hazard Mater 124(1–3):153–164. doi:10.1016/j.jhazmat.2005.04.021 CrossRef Talawar MB, Sivabalan R, Polke BG, Nair UR, Gore GM, Asthana SN (2005) Establishment of process technology for the manufacture of dinitrogen pentoxide and its utility for the synthesis of most powerful explosive of today—CL-20. J Hazard Mater 124(1–3):153–164. doi:10.​1016/​j.​jhazmat.​2005.​04.​021 CrossRef
224.
Zurück zum Zitat Tappan AS, Basiliere M, Ball JP, Snedigar S, Fischer GJ, Salton J (2010) Linear actuation using milligram quantities of CL-20 and TAGDNAT. Propellants, Explos, Pyrotech 35(3):207–212. doi:10.1002/prep.201000025 CrossRef Tappan AS, Basiliere M, Ball JP, Snedigar S, Fischer GJ, Salton J (2010) Linear actuation using milligram quantities of CL-20 and TAGDNAT. Propellants, Explos, Pyrotech 35(3):207–212. doi:10.​1002/​prep.​201000025 CrossRef
225.
Zurück zum Zitat Tappan BC, Brill TB (2003) Thermal decomposition of energetic materials 86. Cryogel synthesis of nanocrystalline CL-20 coated with cured nitrocellulose. Propellants, Explos, Pyrotech 28(5):223–230 doi:10.1002/prep.200300009 Tappan BC, Brill TB (2003) Thermal decomposition of energetic materials 86. Cryogel synthesis of nanocrystalline CL-20 coated with cured nitrocellulose. Propellants, Explos, Pyrotech 28(5):223–230 doi:10.​1002/​prep.​200300009
226.
Zurück zum Zitat Thiboutot S, Brousseau P, Ampleman G, Pantea D, Cote S (2008) Potential use of CL-20 in TNT/ETPE-based melt cast formulations. Propellants, Explos, Pyrotech 33(2):103–108. doi:10.1002/prep.200700223 CrossRef Thiboutot S, Brousseau P, Ampleman G, Pantea D, Cote S (2008) Potential use of CL-20 in TNT/ETPE-based melt cast formulations. Propellants, Explos, Pyrotech 33(2):103–108. doi:10.​1002/​prep.​200700223 CrossRef
227.
Zurück zum Zitat Tian Q et al (2013) Thermally induced damage in hexanitrohexaazaisowurtzitane. Cent Eur J Energ Mater 10(3):359–369 Tian Q et al (2013) Thermally induced damage in hexanitrohexaazaisowurtzitane. Cent Eur J Energ Mater 10(3):359–369
228.
Zurück zum Zitat Tomas-Alonso F, Rubio AM, Alvarez R, Ortuno JA (2013) Dynamic potential response and SEM-EDX studies of polymeric inclusion membranes based on ionic liquids. Int J Electrochem Sci 8(4):4955–4969 Tomas-Alonso F, Rubio AM, Alvarez R, Ortuno JA (2013) Dynamic potential response and SEM-EDX studies of polymeric inclusion membranes based on ionic liquids. Int J Electrochem Sci 8(4):4955–4969
229.
230.
Zurück zum Zitat Van der Heijden AEDM (1998) Crystallization and characterization of energetic materials. Curr Top Cryst Growth Res 4:99–114 Van der Heijden AEDM (1998) Crystallization and characterization of energetic materials. Curr Top Cryst Growth Res 4:99–114
231.
Zurück zum Zitat van der Heijden AEDM, Bouma RHB, van der Steen AC (2004) Physicochemical parameters of nitramines influencing shock sensitivity. Propellants, Explos, Pyrotech 29(5):304–313. doi:10.1002/prep.200400058 CrossRef van der Heijden AEDM, Bouma RHB, van der Steen AC (2004) Physicochemical parameters of nitramines influencing shock sensitivity. Propellants, Explos, Pyrotech 29(5):304–313. doi:10.​1002/​prep.​200400058 CrossRef
232.
Zurück zum Zitat van der Heijden AEDM, Bouma RHB, van der Steen AC (2004) Physicochemical parameters of nitramines influencing shock sensitivity. Propellants, Explos, Pyrotech 29(5):304–313. doi:10.1002/prep.200400058 CrossRef van der Heijden AEDM, Bouma RHB, van der Steen AC (2004) Physicochemical parameters of nitramines influencing shock sensitivity. Propellants, Explos, Pyrotech 29(5):304–313. doi:10.​1002/​prep.​200400058 CrossRef
233.
Zurück zum Zitat Viswanath DS, Reinig M, Ghosh TK, Boddu VM (2010) Vapor pressure of nitro compounds, vol Pt. 1. University of Pardubice, Institute of Energetic Materials, pp 306–309 Viswanath DS, Reinig M, Ghosh TK, Boddu VM (2010) Vapor pressure of nitro compounds, vol Pt. 1. University of Pardubice, Institute of Energetic Materials, pp 306–309
234.
Zurück zum Zitat Viswanath JV, Venugopal KJ, Rao NVS, Venkataraman A (2016) An overview on importance, synthetic strategies and studies of 2,4,6,8,10,12-hexanitro-2,4,6,8,10,12-hexaazaisowurtzitane (HNIW). Defence Technol 12(5), October 2016, pp 401–418 Viswanath JV, Venugopal KJ, Rao NVS, Venkataraman A (2016) An overview on importance, synthetic strategies and studies of 2,4,6,8,10,12-hexanitro-2,4,6,8,10,12-hexaazaisowurtzitane (HNIW). Defence Technol 12(5), October 2016, pp 401–418
236.
Zurück zum Zitat Volk F, Bathelt H (1995) Influence of energetic materials on the energy-output of gun propellants. Am Defense Preparedness Assoc: 82–89 Volk F, Bathelt H (1995) Influence of energetic materials on the energy-output of gun propellants. Am Defense Preparedness Assoc: 82–89
237.
Zurück zum Zitat von Holtz E, Ornellas D, Foltz MF, Clarkson JE (1994) The solubility of ε-CL-20 in selected materials. Propellants, Explos, Pyrotech 19(4):12–206. doi:10.1002/prep.19940190410 von Holtz E, Ornellas D, Foltz MF, Clarkson JE (1994) The solubility of ε-CL-20 in selected materials. Propellants, Explos, Pyrotech 19(4):12–206. doi:10.​1002/​prep.​19940190410
238.
Zurück zum Zitat Wu Y, Ou Y, Liu Z, Liu J, Meng Z, Chen B (2004) Theoretical studies on the possible conformers and properties of tetranitrodiazidoacetylhexaazaisowurtzitane (TNDAIW). Sci China, Ser B: Chem 47(5):414–419. doi:10.1360/04yb0046 Wu Y, Ou Y, Liu Z, Liu J, Meng Z, Chen B (2004) Theoretical studies on the possible conformers and properties of tetranitrodiazidoacetylhexaazaisowurtzitane (TNDAIW). Sci China, Ser B: Chem 47(5):414–419. doi:10.​1360/​04yb0046
239.
Zurück zum Zitat Xing X et al (2015) Thermal decomposition behavior of hexanitrohexaazaisowurtzitane and its blending with BTATz (expand) and Al by microcalorimetry. J Therm Anal Calorim: Ahead of Print. doi:10.1007/s10973-015-4431-5 Xing X et al (2015) Thermal decomposition behavior of hexanitrohexaazaisowurtzitane and its blending with BTATz (expand) and Al by microcalorimetry. J Therm Anal Calorim: Ahead of Print. doi:10.​1007/​s10973-015-4431-5
243.
Zurück zum Zitat Zubarev RA, Hakansson P, Hakansson K, Talrose VL (1998) Matrix assisted particle desorption techniques: use of explosive matrixes. Adv Mass Spectrom 14:B061920/1–B061920/8 Zubarev RA, Hakansson P, Hakansson K, Talrose VL (1998) Matrix assisted particle desorption techniques: use of explosive matrixes. Adv Mass Spectrom 14:B061920/1–B061920/8
Metadaten
Titel
Hexanitrohexaazaisowurtzitane (HNIW, CL-20)
verfasst von
Dabir S. Viswanath
Tushar K. Ghosh
Veera M. Boddu
Copyright-Jahr
2018
Verlag
Springer Netherlands
DOI
https://doi.org/10.1007/978-94-024-1201-7_2