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Insensitive High Explosives: III. Nitroguanidine – Synthesis

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Insensitive High Explosives: III. Nitroguanidine – Synthesis Review 1 DOI: 10.1002/prep.201800253 2 3 4 Insensitive High Explosives: III. Nitroguanidine – Synthesis 5 – Structure – Spectroscopy – Sensitiveness 6 7 Ernst-Christian Koch*[a] 8 9 10 11 Abstract: This paper reviews the production, synthesis, sensitive high explosives such as 1,3,5-triamino-2,4,6-trini- 12 crystallography, particle morphology and spectroscopy of trobenzene (TATB), 1,1-diamino-2,2-dinitroethylene (FOX-7) 13 the insensitive high explosive nitroguanidine, (NGu, and N-guanylurea dinitramide (FOX-12), Nitroguanidine 2 14 CH4N4O2), CAS-No: [556-88-7] and its isotopologues [ D4]- proves to be the least sensitive. The review gives 170 refer- 15 15 NGu and [ N4]-NGu]. When compared with standard in- ences to the public domain. For Part II see ref. [1]. 16 Keywords: Nitroguanidine · Nitrimine · Guanidinium nitrate · Insensitive Munitions · Sensitiveness 17 18 19 20 1 Introduction 21 22 Nitroguanidine is an important ingredient in triple base and 23 insensitive, low erosion gun propellants, rocket propellants, 24 gas generators for automobile restraint systems, smoke free 25 pyrotechnics and shock insensitive high explosives [2]. 26 Though nitroguanidine is a frequently used energetic mate- Figure 1. Correct nitrimine structure A (left) and wrong nitramine 27 rial in said different roles it lacks a comprehensive review of structure B (right). 28 its synthesis, structure, spectroscopy and sensitiveness. 29 Nitroguanidine (NGu) (2) has been prepared for the first 30 time by Jousselin [3] through action of concentrated sulphu- 31 ric acid on guanidinium nitrate (GuN) (1) in 1877 cluding FOX-7 (1,1-diamino-2,2-dinitroethylene) [7,8], TATB 32 (Scheme 1). However, he did not correctly identify nitro- (1,3,5-triamino-2,4,6-trinitrobenzene) [9] or LLM-116 (4-ami- 33 guanidine but due to an erroneous nitrogen determination no-3,5-dinitro-1H-pyrazole) [10] as is depicted in Figure 2. 34 misinterpreted NGu for nitrosoguanidine, CAS-No: [674–81– 35 7]. Hence both Pellizzari [4] and Thiele [5] are credited with 36 the first correct identification of nitroguanidine in 1891 and 2 Nomenclature and Property Briefs 37 1892 respectively. 38 The IUPAC name for nitroguanidine is 2-nitroguanidine. Oth- 39 er names include „Petrolite“,„Guanite“or„Picrite“. Some- 40 times nitroguanidine is misspelled in the English literature 41 with a „q“ in lieu of „g“ (which both admittedly may look 42 similar in hand writing) forming the word „nitroquanidine“ 43 and possibly explaining the etymology of the acronym 44 „NQ“. Another common acronym for nitroguanidine used 45 both in the English and German is „NGu“ [11,12]. In wartime 46 Germany „G-Salz“ was used as a disguise for NGu and Scheme 1. Jousselin’s Synthesis of Nitroguanidine later also applied 47 by Pellizzari and Thiele. nowadays „Nigu“ is another common acronym used in Ger- 48 many. However, the latter may be confused with the lead- 49 ing manufacturers name (NIGU Chemie GmbH). In the con- 50 text of this paper we will solely refer to nitroguanidine as 51 Nitroguanidine is a nitrimine – see structure A in Fig- 52 ure 1 – but despite clear scientific evidence [6] also in terms [a] E.-C. Koch 53 of reactivity and spectroscopic data has long been falsely Lutradyn – Energetic Materials 54 described as a nitramine – see structure B in Figure 1. Burgherrenstrasse 132, D-67661 Kaiserslautern, Germany 55 NGu possesses the same vicinal amino-nitro-arrange- *e-mail: [email protected] 56 ment as a number of other insensitive high explosives in- Homepage: www.lutradyn.com Propellants Explos. Pyrotech. 2019, 44, 1–27 © 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim 1 These are not the final page numbers! ÞÞ Review E.-C. Koch 1 2 3 4 5 6 7 8 9 10 11 Figure 2. Emphasized vicinal amino-nitro-arrangement in NGu (2), FOX-7 (3), TATB (4) and LLM-116 (5). 12 13 14 Table 1. Properties of nitroguanidine (NGu) and its precursor gua- 15 NGu (2). NGu is characterised by its chemical formula, nidinium nitrate (GuN) after Ref. [7,13,14]. 16 CH4N4O2 and its CAS-No [556–88–7] (though the entry in 17 CAS is linked to the erroneous nitramine – structure B as Unit NGu (2) GuN (1) 18 depicted in Figure 2). CAS-No. [556–88–7] [506–93–4] 19 NGu is an off-white crystalline material occurring in solid Formula CH4N4O2 CH6N4O3 20 and hollow needles of large l/d ratio, as platelets from crys- W wt.-% À30.75 À26.21 21 tallisation with colloidal agents and as spherical grains N wt.-% 53.83 45.89 m gmolÀ1 104.068 122.084 22 through crystallization from special solvents. Important r 1 at 298 K gcmÀ3 1.759 1.444 23 physical and chemical properties of NGu and of its direct À1 DfH kJmol À86 À387 24 precursor, guanidinium nitrate (1), are depicted in Table 1. Mp 8C 257 (dec.) 217 25 Tdec 8C 254 250 À1 26 DexH kJmol À405.7 À345.7 À1 27 3 Producer kJg À3.898 À2.831 kJcmÀ3 À6.857 À4.066 28 À1 À1 cp Jg K 1.198 – 29 In NATO member states the exclusive bulk producer for À1 cL ms 3350* – 30 NGu is AlzChem Trostberg GmbH with headquarters in Trost- k WmÀ1 KÀ1 4.1 10À3 – 31 berg, Germany located in the Bavarian Chemical Triangle À1 S(H2O) at 258Cgkg 3.45 165 32 [15]. ARC 8C 159, f= 5.82 – À1 # À3 33 VD ms 8344 3700 (at 1.436 gcm ) # 34 PCJ GPa 29.0 p À1 # 35 4 Synthesis and Formation of Nitroguanidine 2EG ms 2435 – Impact J >50 >50 36 Friction N >355 >355 37 The process flow chart for Nitroguanidine production start- À3 # 38 ing from burnt lime stone and coke is depicted in * 95 wt.-% NGu, 5 wt.-% Estane, 1=1.704 gcm (98. 7% TMD). À3 39 Scheme 2. 95 wt.-% NGu, 5 wt.-% Viton A, 1=1.742 gcm (97.9% TMD). Index: ARC= Adiabatic self-heating onset temperature (8C); CAS= 40 Chemical Abstracts Service Registry Number; cL =Velocity of sound 41 À1 À1 À1 (longitudinal) (ms ); cp =Specific heat (Jg K ); Friction=Friction 42 4.1 Industrial Process Sensitivity with BAM-apparatus; GuN= Guandine nitrate, CH6N4O3; 43 Impact = Impact Sensitivity with BAM-apparatus; Mp= Melting À1 44 4.1.1 NGu-Precursor point (8C); mr =Molecular mass (gmol ); PCJ =Detonation (Chap- À1 45 man Jouguet) Pressure (GPa); S= Solubility (gkg ); Tdec =Decom- = = 46 4.1.1.1 Calcium Carbide – Calcium Cyanamide position temperature (8C); Ti Ignition temperature (8C); DexH Enthalpy of explosion (kJmolÀ1); D H = Enthalpy of formation 47 f (kJmolÀ1); k=Thermal conductivity (WmÀ1 KÀ1); W= Oxygen bal- 48 The largescale industrial process chain of NGu typically ance (wt.-%), N=Nitrogen Content (wt.-%); 1=Density (gcmÀ3); p À1 49 starts with the production of calcium carbide from burnt 2EG = Gurney Velocity (ms ) 50 limestone and carbon according to 51 1 1 52 CaOðsÞþ3CðsÞþ0:23 kWhÀ molÀ replaced by plastic waste fraction. The reaction of calcium electrically heated furnance ð1Þ 53 carbide in the presence of catalytic amounts of CaCl2 or !CaC2ðlÞþCOðgÞ 54 CaF2 with nitrogen yields calcium cyanamide, CaCN2 (Polze- 55 with an increasing amount of anthracite being nowadays niusz-Krauß process). 56 2 www.pep.wiley-vch.de © 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim Propellants Explos. Pyrotech. 2019, 44, 1–27 ÝÝ These are not the final page numbers! Insensitive High Explosives: III. Nitroguanidine – Synthesis – Structure – Spectroscopy – Sensitiveness 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 Scheme 2. Flow chart for state-of-the-art Nitroguanidine production. 22 23 700À900C; CaX 24 2 À1 Table 2. Properties of dicyandiamide, DCD (6). CaC2ðsÞþN2ðgÞ ! CaCN2ðsÞþCðsÞþ286 kJ mol 25 Unit 26 ð2Þ 27 CAS-No. 461-58-5 The alternative Frank-Caro process operates at higher 28 Formula C2H4N4 temperature and requires initial ignition of a reaction mix- 29 W wt.-% À114.17 ture diluted with ~20 wt.-% CaCN2. N wt.-% 66.64 30 À1 mr gmol 84.081 31 1 at 298 K gcmÀ3 1.404 32 4.1.1.2 Dicyandiamide À1 DfH kJmol +23 À1 À1 33 cp Jg K 1,415 À1 34 Calcium cyanamide is hydrolysed in cold water to yield di- S(H2O) at 208Cgkg 32 35 cyandiamide (DCD)(6) (Figure 3) in a two-step reaction: Mp 8C211 36 Tdec 8C 252 37 Abbreviations: CAS= Chemical Abstracts Service; cp =Specific heat À1 À1 À1 38 (Jg K ); Mp=Melting point (8C); mr =Molecular mass (gmol ); À1 39 S=Solubility (gkg ); Tdec =Decomposition temperature (8C); DfH= À1 40 Enthalpy of formation (kJmol ); W=Oxygen balance (wt.-%), N= Nitrogen Content (wt.-%); 1= Density (gcmÀ3); 41 42 Figure 3. Structure of dicyandiamide, (6). 43 44 4.1.1.3 Guanidinium Nitrate 45 46 There are around twenty different routes for the synthesis 2CaCN2ðsÞþ2H2OðlÞ!CaðCN2HÞ2ðsÞþCaðOHÞ2ðsÞð3aÞ 47 of GuN. In the following only those relevant on a technical 48 scale will be discussed. CaðCN2HÞ2 þ 2H2OðlÞ!CaðOHÞ2þ 49 ð3bÞ H N C N C N 16 50 ð 2 Þ2 ¼ À ½ 4.1.1.3.1 Guanidinium Nitrate from Ammonium Thio- 51 cyanate Important properties of DCD are given in Table 2. 52 53 Ammonium thiocyanate, NH4SCN, (CAS-No. [172–95–41]) 54 was long a very abundant chemical resulting from the de- 55 sulphurization of coal gas in municipal gas works with am- 56 monia. Disproportionation of NH4SCN (eq. 4) yields guani- Propellants Explos. Pyrotech. 2019, 44, 1–27 © 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim www.pep.wiley-vch.de 3 These are not the final page numbers! ÞÞ Review E.-C.
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