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DOI: 10.1002/prep.201300017

Prediction of Sensitivity of Energetic Compounds with a New Computer Code

Mohammad Hossein Keshavarz,*[a] Hadi Motamedoshariati,[a] Reza Moghayadnia,[a] Majid Ghanbarzadeh,[a] and Jamshid Azarniamehraban[a]

Abstract : Impact, electrostatic, and shock sensitivities of energetic compounds are three important parameters for the assessment of hazardous energetic materials. A novel easy to handle and user-friendly computer code, written in Visual Basic, is introduced to predict these parameters, by solely using the molecular structure of an energetic molecule. It is able to predict impact sensitivity for different types of energetic compounds including nitropyridines, nitroimidazoles, nitropyrazoles, nitrofurazanes, nitrotriazoles,

nitropyrimidines, polynitro arenes, benzofuroxans, polynitro arenes with a-CH, nitramines, nitroaliphatics, nitroaliphatic containing other functional groups, and nitrate energetic compounds. It can also provide reliable results for electrostatic and shock sensitivities of some classes of high explosives including nitroaromatic and nitramine compounds. The prediction of this code give good values for some newly reported energetic compounds, where experimental data are available.

Keywords: Energetic material Hazard assessment Impact sensitivity Electrostatic sensitivity Shock sensitivity

1 Introduction
It is important to understand the relationship between the molecular structures of energetic molecules and their sensitivities to specific stimuli. Impact, friction, shock, electrostatic discharges, and heat are some of the well-known stimuli for decomposition of an energetic molecule by deflagration and detonation. Values of impact, electrostatic and shock sensitivities of energetic compounds have been reviewed elsewhere [15]. For calculation of the potential performance of the energetic material of interest, the condensed phase heat of formation should be used in the corresponding computer codes such as CHEETAH [6] and NASA-CEC-71 [7]. Moreover, the crystal or loading density is also an input parameter in the complex well-known thermochemical/hydrodynamic computer codes such as CHEETAH [6] to predict various thermodynamic and detonation parameters. LOTUSES [8] and EDPHT [9] are two suitable computer codes that are based on empirical models. The new version of EDPHT, i.e. EDPHT 2.0 [10], can calculate crystal density, the condensed phase heat of formation and activation energy of thermolysis of high explosive, the velocity of detonation, detonation pressure, heat of detonation, detonation temperature, Gurney velocity, adiabatic exponent, and specific impulse of high explosives. The purpose of this work is to develop a novel computer code for prediction of impact, electrostatic and shock sensitivities of energetic compounds on the basis of recent developments of the predictive methods. This computer code is able to calculate the impact sensitivity of different types
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of energetic compounds including nitropyridines, nitroimidazoles, nitropyrazoles, nitrofurazanes, nitrotriazoles, nitropyrimidines, polynitro arenes, benzofuroxans, polynitro arenes with a-CH, nitramines, nitroaliphatics, nitroaliphatic containing other functional groups, and nitrate energetic compounds. For some classes of high explosives including nitroaromatic and nitramine compounds, it can predict quickly reliable results of electrostatic and shock sensitivities. The predicted results of this code will be tested for some newly reported energetic compounds.

2 Theory
Simple and reliable approaches have been recently introduced to predict impact, electrostatic and shock sensitivities of energetic compounds [15,1121].
2.1 Impact Sensitivity

The impact sensitivity test involves subjecting a sample to the impact of the standard mass falling from different
[a] M. H. Keshavarz, H. Motamedoshariati, R. Moghayadnia, M. Ghanbarzadeh, J. Azarniamehraban Department of Chemistry Malek-ashtar University of Technology Shahin-shahr P. O. Box 83145/115, Iran *e-mail: mhkeshavarz@mut-es.ac.ir keshavarz7@gmail.com

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heights, typically with a 2.5 kg mass. Since hot spots in the material contribute to initiation in the drop weight impact test, a height of 50% probably in causing an explosion (h50) is measured during hitting of sample by a hammer. Despite the limitations and uncertainties associated with the impact test, there are many approaches to assess impact sensitivity through different molecular properties, e.g. simple correlations [14,12,14,18,21] and quantum mechanical methods [2,5,2227] as well as artificial neural network and quantitative structure-property relationship (QSPR) on the basis of molecular structure or suitable property [28 32], especially within chemical families.
2.1.1 Reliable Approach for Prediction of Impact Sensitivity of Nitroaromatics, Nitramines, and Nitroaliphatics

only the additive contribution of the number of carbon and hydrogen atoms. The values h50ds and h50is can be predicted on the basis of molecular structure as given in Table 2. For the presence of another more active site for initiation of decomposition in polynitroheteroarenes, e.g. R NO2, the values of h50ds and h50is can be taken as zero.
2.2 Electrostatic Sensitivity

Among different studies, it was recently indicated that a general reliable correlation can be given for the prediction of impact sensitivity of nitroaromatics, benzofuroxans, nitroaromatics with a-CH, nitramines, nitroaliphatics, nitroaliphatic containing other functional groups, and nitrate energetic compounds with general formula CaHbNcOd, which can be given as follows [21]:
is 111:6hds 50 132:3h50 MW

Electrostatic or electric spark sensitivity is defined as the degree of sensitivity to the electrostatic discharge. It can be measured by the electrostatic discharge energy (EES) required for 50% initiation probability. It also depends on the configuration of the electrodes and the structure of the circuit, which can provide diverse results by different test specification of electrode energy [33]. Two different instruments RDAD and ESZ KTTV have relatively simple constructions, which can be used to determine the values of EES [33, 34].
2.2.1 Using Molecular Structure to Predict Electrostatic Sensitivity of Nitroaromatic Energetic Compounds

log h50 log h50 elem log h50 elem

1a 1b

A reliable correlation was introduced with respect to the other methods for prediction of electric spark sensitivity of nitroaromatic energetic compounds, which can be given as follows [15]: E ES 4:600:733a 0:724d 9:16r b=d 5:14CR,OR 3

48:81a 25:94b 13:73c 4:786d MW

where (log h50)elem is the contribution of elemental composition to impact sensitivity, h50ds and h50is are decreasing and increasing sensitivity structural parameters, respectively, and MW is the molecular mass of the energetic compound. The values of h50ds and h50is can be specified according to the molecular structures as given in Table 1.

where EES is electric spark sensitivity in J, rb/d is the ratio of the number of hydrogen to oxygen atoms, CR,OR is the existence of alkyl (R) or alkoxy groups (OR) in a nitroaromatic energetic compound. The values of CR,OR are 1.0 and 2.0 for the attachment of alkyl and alkoxy groups to nitroaromatic ring, respectively.
2.2.2 Prediction of Electrostatic Sensitivity of Nitramines

2.1.2 Suitable Method for Estimation of Impact Sensitivities of Polynitro Heteroarenes

As compared to the other methods, a simple and reliable correlation has been recently introduced to predict impact sensitivity of different types of polynitro heteroarenes, which include nitropyridine, nitroimidazole, nitropyrazole, nitrofurazane, nitrooxadiazole, nitro-1,2,4-triazole, nitro1,2,3-trazole, and nitropyrimidine explosives [18], as follows: 117:6 log h50 log h50 0 elem log h50 0 elem 52:13a 31:80b MW P
i

Another simple and reliable relationship has also been introduced for prediction of electrostatic sensitivity on the basis of the existence of two molecular moieties as [19]: EES J 3:46 6:504ra=d 4059CCH2 NNO2 3;COO or NH 4

is hds 50 i h50 i

2a

MW 2b

where CCH2 NNO2 3;COO or NH is the existence of methylenenitramine greater than or equal three in cyclic nitramines or the presence of COO- or CONH-functional groups. The values of CCH2 NNO2 3;COO or NH are 1.0 and 1.0 for cyclic nitramines containing CH2NNO2  3 and nitramines including COO- or CONH-functional groups, respectively.
2.3 Shock Sensitivity

In contrast to (log h50)elem, the value of (log h50)elem depends 96

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For indication of the shock sensitivity of an explosive, various gap tests were used to qualitatively measure the shock
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Prediction of Sensitivity of Energetic Compounds Table 1. Summary of h50ds and h50is given in Equation (1a). Name Functional groups or molecular moi- h50ds eties h50is Illustration or condition If n(NO2)  3 per each aromatic cycle

Benzofuroxanes Nitroaromatics NH2 group

Presence of only OH groups OR groups attached to aromatic rings

0.6 0.7 [for n(NH2) = 1 per each aro- matic cycle] 1.2 [for n(NH2) = 2 per each aro- matic cycle] 1.7 [for n(NH2) = 3 per each aro- matic cycle] 0.9 0.7

If n(NO2)=n(NH) If NH2 group has also attached to aromatic ring simultaneously, the value of h50ds changes to 1.2

0.5 O groups attached to aromatic rings Double and triple bonds on carbon 1.0 attached to aromatic ring (e.g. C(= O) and CN) 2.0 Presence of one methyl group An alpha CH linkage attached to nitroaromatic ring Azido or diazo functional group

If n(NO2)  3 in aromatic ring

Nitramines

Nitroaliphatics

The existence of CH3C(NO2)2CH2 simultaneously attached to COO functional group 0.8 If there is one phenyl or one OH group in meta position with respect to methyl group 0.5 The presence of one methyl group is an exception that can decrease sensitivity the value of h50ds equals 1.2 0.7 0.5 The presence of molecular structure =CN NO2 has reverse effect so that the value of h50ds is 0.45. Nitroaliphatics that contain COO functional The number of CH3C(NO2)2CH2 and (CH3)2C(NO2)(CH2) attached group to COO

wave amplitude required to initiate detonation in explosives, e.g. at Naval Surface Warfare Center (NSWC) and Los Alamos National Laboratory (LANL). A standard test can be used to measure shock sensitivity in which the collection of information has been gathered by NSWC using Navy small scale gap test [35]. The suitable equations can be given as: P90%TMD 1679:0 226:3L 631:4EaCH=NNO2 1771:9G pure 5a P95%TMD 2196:4 247:9L 636:8EaCH=NNO2 3292:1G pure 5b P98%TMD 2544:9 221:1L 416:2EaCH=NNO2 4639:2G pure 5c where P90%TMD, P95%TMD, and P98%TMD are the pressure in MPa required to initiate the material pressed to 90%, 95%, and 98% of theoretical maximum density (TMD), respectively; L and Gpure are a + b/2d and 193nNH2 nNO2 , respectively; and EaCH=NNO2 is equal to 1.0 for nitramines or a-CH linkage in nitroaromatic compounds.
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3 Computation of Impact, Electrostatic and Shock Sensitivities by New Computer Code

A new version of the computer code, EDPHT 3.0, is improved to run on windows operating system using modern modular and object-oriented techniques in Visual Basic 6.0. It occupies about 4.8 MB of hard disk space in the computer and its output can be directly printed. Furthermore, EDPHT 3.0 can be installed in Windows 98, 2000, XP as well as Windows 7.0. The algorithm of EDPHT 3.0 in prediction of impact, electrostatic and shock sensitivities of pure CaHbNcOd energetic materials is shown in Figure 1 as flow chart. There is no need to use any further experimental data. The knowledge of the molecular structure of energetic compounds is only essential parameter. Empirical formula and specific molecular moieties affecting the predicted values of h50 and EES as well as P90%TMD, P95%TMD, and P98%TMD are used as input parameters.

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Polynitro heteroarene

M. H. Keshavarz, H. Motamedoshariati, F. Gharagheizi, R. Moghayadnia, M. Ghanbarzadeh, J. Azarniamehraban

Table 2. Summary of h50ds and h50is given in Equation (2a). Molecular moieties h50ds h50is Illustration or condition 0

Amino derivatives as substituents in central heteroarene

Central heteroarene containing four nitrogens or three nitrogens attached subsequently in one ring or nitropyrimidine explosives with attaching an aromatic ring to nitrogen Central heteroarene including nitropyridine Central heteroarene including nitrofurazane (or nitrooxidazole) Central heteroarene including nitro1,2,4-triazole (or nitropyrimidine) Central heteroarene containing only nitrogen as hetero atoms The attachment of an aromatic ring The attachment of aromatic ring to nitrogen (e.g. picryl) to nitrogen and presence in imidazole (or only in mononitro imidazol) of one nitro group in specific position The attachment of aromatic ring to nitrogen in nitropyrazole The existence of polynitrophenyl as an attachment on nitrogen atom at 4-position for 1,2,4-triazole The existence of one nitro group in positions of 2 in 3 (or 5) in nitropyrazole

0.5 0.6 2.5 2.0 1.0

For the existence of only two aromatic substituents attached to heteroarene ring without further substituents, the value of is 2.0

0.6 0.7

0.6

This condition is valid for nitroimidazole up to only disubstitueted nitroimidazole explosives.

Derivatives of nitro-1,2,3-triazole explosives

The existence of one nitro group in positions 0.8 of 2 in 3 (or 5) in nitroimidazole The existence of one nitro group in positions 1.0 of 3 in nitro-1,2,4-triazole The attachment of an aromatic ring to nitro- gen in position 1

1.0 This condition is valid for the absence of amino derivatives

Figure 1. Block diagram of the software EDPHT 3.0.

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Prediction of Sensitivity of Energetic Compounds Table 3. Comparison of the calculated impact sensitivity /cm by EDPHT 3.0 for several new explosives with the measured values [41]. Name 2,4,6-Tris(3,5-diamino-2,4,6-trinitrophenylamino)-1,3,5-triazine (PL-1) 3-Amino-5-nitro-1,2,4-triazole (ANTA) 5-Nitro-4,6-bis(5-amino-3-nitro-1H-1,2,4-triazole-1yl) (DANTNP) 4-Picrylamino-2,6-dinitrotoluene (PADNT) N,N-Bis(1,2,4-triazol-3-yl)-4,4-diamino-2,2,3,3,5,5,6,6-octanitroazobenzene (BTDAONAB) 2,4,6,8,10,12-Hexanitro-2,4,6,8,10,12-hexaazaisowurtzitane (CL-20) 4,4-Dinitro-3,3-bifurazan (DNBF) 7-Amino-4,6-dinitrobenzofuroxan (ADNBF) 2,6-Bis(picrylamino)-3,5-dinitropyridine (PYX) Formula C21H15N21O18 C2H3N4O2 C8H5N13O6 C13H8N6O10 C16H6N18O16 C6H6N12O12 C4N2O6 C6H3N5O6 C17H7N11O16 Exp. 170 > 170 > 170 135 87 12 to 21 20 to 28 12 53 63 Calcd. 134 > 170 138 97 61 13 16 49 61 Dev. 36 0.0 32 38 26 1 to 8 7 to 15 4 4 2

Table 4. Comparison of the calculated electrostatic sensitivity /J by EDPHT 3.0 for several new explosives with the measured values. Name 2,4,6,8,10,12-Hexanitro-2,4,6,8,10,12-hexaazaisowurtzitane (CL-20) 2,4,6-Tris(3,5-diamino-2,4,6-trinitrophenylamino)-1,3,5-triazine (PL-1) 3-Amino-5-nitro-1,2,4-triazole (ANTA) N,N-Bis(1,2,4-triazol-3-yl)-4,4-diamino-2,2,3,3,5,5,6,6-octanitroazobenzene (BTDAONAB) 3,5-Dinitropyridine-2,6-diamine (DADNPy) 2,4,6-Trinitrobenzene-1,3,5-triamine (TATB) 1,4,5,8-Tetranitrodecahydropyrazino[2,3-b]pyrazine (TNAD) 1,4-Dinitrotetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dione (DINGU) Cyclotetramethylenetetranitramine Formula C6H6N12O12 C21H15N21O18 C2H3N4O2 C16H6N18O16 C5H5N5O6 C6H6N6O6 C6H10N8O8 C4H4N6O6 C4H8N8O8 Exp. 12.40 [42] 17.71 [42] 5.43 [43] 15.19 [43] 2.89 [43] Calcd. 2.65 16.47 18.32 7.89 15.28 13.71 4.28 11.86 2.65 Dev. 2.88 4.00 1.15 3.33 0.24

4 Validation of New Computer Code

The computed values of sensitivity of EDPHT 3.0 can be validated by comparing outputs with the experimentally determined results reported in the literature.

4.3 The Predicted Values of P90%TMD, P95%TMD, and P98%TMD

4.1 Comparison of the Values of h50

A comparison of the calculated impact sensitivities of the new explosives with experimental data are given in Table 3. As seen in Table 3, the predicted results of EDPHT 3.0 are close to experimental data, which confirm its reliability.

Shock sensitivity is another important kind of sensitivity, which is interpreted as being directly proportional to the maximum gap width through which a given shock wave generated by another explosive such as RDX initiate the test material in 50% of the trials. Table 5 shows the predicted values of P90%TMD, P95%TMD, and P98%TMD for some energetic compounds. For high performance and sensitive explosives such as CL-20, positive values of their condensed phase enthalpy of formation are responsible for increasing detonation performance, thermodynamic instability and sensitivity.
4.4 Restrictions of EDPHT 3.0

4.2 Estimation of EES

It was indicated that experimental values of electrostatic sensitivity of energetic materials depend on various factors such as granulometry and particle shape [36,37], moisture content [36], the molecular electronic properties [38], the configuration of electrodes [3840], and the general structure of the circuit [36]. As seen in Table 4, the predicted electrostatic sensitivities for the compounds are consistent with their impact sensitivities given in Table 3. Higher electric spark energy is required for less sensitive energetic compounds according to the following order: ANTA > PL-1 > BTDAONAB > CL-20

The new computer code EDPHT 3.0 has the advantage that it only requires elemental composition and some molecular fragments for calculation of impact, electrostatic and shock sensitivity of different classes of energetic compounds. It has also several limitations: (a) The EDPHT 3.0 can be applied to those explosives that contain only carbon, hydrogen, nitrogen, and oxygen atoms. (b) Since sensitivity of explosives depends on particle size especially nanoscale with respect to macroscale, the EDPHT 3.0 can predict sensitivity only for macroscale energetic compounds. (c) The reliability of new computer code may be reduced for the prediction of the electric spark sensitivity because
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Name

M. H. Keshavarz, H. Motamedoshariati, F. Gharagheizi, R. Moghayadnia, M. Ghanbarzadeh, J. Azarniamehraban

Table 5. Comparison of P90%TMD, P95%TMD, and P98%TMD /MPa by EDPHT 3.0 for several new explosives with the measured values [35]. Formula C12H4N8O Exp. 3443 4126 7038 12192 16486 1081 1432 1749 Calcd. 3036 3684 3871 7301 12125 16151 1048 1560 2129 2697 3312 3540 369 816 1465 2018 2568 2877 2358 2940 3208 1226 1701 2103 Dev. 407 442 263 67 335 33 128 380

1,3,7,9-Tetranitrodibenzo-1,3a,4,6a-tetraazapentalene (TACOT-z)

2,4,6-Trinitrobenzene-1,3,5-triamine (TATB)

C6H6N6O6

Cyclotetramethylenetetranitramine

C4H8N8O8

2,6-Bis(picrylamino)-3,5-dinitropyridine (PYX)

C17H7N11O16

2,4,6,8,10,12-Hexanitro-2,4,6,8,10,12-hexaazaisowurtzitane (CL-20)

C6H6N12O12

7-Amino-4,6-dinitrobenzofuroxan (ADNBF)

C6H3N5O6

N,N-Bis(1,2,4-triazol-3-yl)-4,4-diamino-2,2,3,3,5,5,6,6-octanitroazobenzene (BTDAONAB)

C16H6N18O16

4,4-Dinitro-3,3-bifurazan (DNBF)

C4N2O6

some external parameters such as the configuration of electrodes may affect the experimental values.
[3]

5 Conclusions
A novel easy to handle computer code was introduced that can provide a reliable estimation of impact, electrostatic and shock sensitivity for a wide range of energetic compounds. Elemental composition and some molecular fragments are the only input parameters for this code. To validate EDPHT 3.0 for the prediction of impact, electrostatic and shock sensitivity, several new compounds of different classes of explosives have been tested.

[4]

[5]

[6]

[7]

Acknowledgments
We would like to thank the research committee of Malek-ashtar University of Technology (MUT) for supporting this work. [8]

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