Predicting explosibility properties of chemicals from quantitative structure-property relationships

Process Safety Progress

Volumn 29, Issue 4, 2010, Pages 359-371

  Fayet, G ^a,b   Rotureau, P ^b   Joubert, L ^a   Adamo, C ^a  

^a PSL RESEARCH UNIVERSITY   (France)

^b INSTITUT NATIONAL DE L ENVIRONNEMENT INDUSTRIEL ET DES RISQUES INERIS   (France)

Author keywords

DFT; Explosibility; QSPR

Indexed keywords

ALTERNATIVE METHODS; DENSITY FUNCTIONAL THEORY CALCULATIONS; DESCRIPTORS; DFT; ECOTOXICOLOGICAL; EUROPEAN REGULATION; EXPLOSIBILITY; HAZARDOUS PROPERTIES; MOLECULAR DESCRIPTORS; MULTI-LINEAR REGRESSION; PHYSICO-CHEMICALS; PHYSICOCHEMICAL PROPERTY; QSPR; QUANTITATIVE STRUCTURE PROPERTY RELATIONSHIPS; QUANTUM CHEMICAL; QUANTUM CHEMICAL CALCULATIONS; SCREENING PROCESS; STATISTICAL ANALYSIS; THEORETICAL CALCULATIONS; THERMAL STABILITY; TYPE METHODS;

AROMATIC COMPOUNDS; CHEMICAL ANALYSIS; CHEMICAL PROPERTIES; DENSITY FUNCTIONAL THEORY; ELECTRIC SPARKS; FORECASTING; QUANTUM CHEMISTRY;

INDICATORS (CHEMICAL);

EID: 79953760937     PISSN: 10668527     EISSN: 15475913     Source Type: Journal    
DOI: 10.1002/prs.10379     Document Type: Article

References (64)

1. Regulation (EC) No 1907/2006 of the European Parliament and of the Council of 18 December 2006 concerning the Registration, Evaluation, Authorisation and Restriction of Chemicals (REACH). OJ L 396, 30.12.2006.
2. United Nations, Globally Harmonized System of Classification and Labelling of Chemicals (GHS), Second Revised Edition, Geneva, 2007.
3. United Nations, Recommendations on the Transport of Dangerous Goods: Manual of Tests and Criteria,Fifth Revised Edition, Geneva, 2009.
4. E.S. Shanley and G.A. Melhem, A review of ASTM CHETAH 7.0 hazard evaluation criteria, J Loss Prev Process Ind 8 (1995), 261-264.
5. S.W. Benson, Thermochemical Kinetics, Wiley, New York, 1976.
6. W.C. Lothrop and G.R. Handrick, The relationship between performance and constitution of pure organic explosive compounds. Chem Rev 44 (1949), 419-445.
7. G.A. Melhem and E.S. Shanley, On the estimation of hazard potential for chemical substances, Process Saf Prog 15 (1996), 168-172.
8. S.R. Saraf, W.J. Rogers, and M.S. Mannan, Prediction of reactive hazards based on molecular structure, J Hazard Mater 98 (2003), 15-29.
9. C.D. Selassie, R. Garg, S. Kapur, A. Kurup, R.P. Verma, S.B. Mekapati, and C. Hansch, Comparative QSAR and the radical toxicity of various functional groups, Chem Rev 102 (2002), 2585-2606.
10. S.P. Bradbury, Quantitative structure-activity relationships and ecological risk assessment: An overview of predictive aquatic toxicology research, Toxicol Lett 79 (1995), 229-237.
11. H. Gao, J.A. Katzenellenbogen, R. Garg, and C. Hansch, Comparative QSAR analysis of estrogen receptor ligands, Chem Rev 99 (1999), 723-744.
12. D.A. Winkler, The role of quantitative structure-activity relationships (QSAR) in biomolecular discovery, Brief Bioinf 3 (2002), 73-86.
13. M. Grover, B. Singh, M. Bakshi, and S. Singh, Quantitative structure-property relationships in pharmaceutical research-Part 1, Pharm Sci Tech Today 3 (2000), 28-35.
14. M. Grover, B. Singh, M. Bakshi, and S. Singh, Quantitative structure-property relationships in pharmaceutical research-Part 2, Pharm Sci Tech Today 3 (2000), 50-57.
15. A.R. Katritzky, V.S. Lobanov, and M. Karelson, QSPR: The correlation and quantitative prediction of chemical and physical-properties from structure, Chem Soc Rev 24 (1995), 279-287.
16. A.R. Katritzky, M. Karelson, and V.S. Lobanov, QSPR as a means of predicting and understanding chemical and physical properties in terms of structure, Pure Appl Chem 69 (1997), 245-248.
17. J. Taskinen and J. Yliruusi, Prediction of physicochemical properties based on neural network modelling, Adv Drug Deliv Rev 55 (2003), 1163-1183.
18. E.E. Bolton, Y. Wang, P.A. Thiessen, and S.H. Bryant,PubChem: Integrated platform of small molecules and biological activities, annual reports in computational chemistry, Elsevier, Amsterdam (2008), pp. 217-241.
19. PubChem,http://pubchem.ncbi.nlm.nih.gov.
20. G. Fayet, L. Joubert, P. Rotureau, and C. Adamo, Theoretical study of the decomposition reactions in substituted nitrobenzenes, J Phys Chem A 112 (2008), 4054-4059.
21. T.B. Brill and K.J. James, Kinetics and mechanisms of thermal decomposition of nitroaromatic explosives, Chem Rev 93 (1993), 2667-2692.
22. G. Fayet, L. Joubert, P. Rotureau, and C. Adamo, A theoretical study of the decomposition mechanisms on substituted ortho-nitrotoluenes, J Phys Chem A 113 (2009), 13621-13627.
23. M.H. Keshavarz and H.R. Pouretedal, Simple empirical method for prediction of impact sensitivity of selected class of explosives, J Hazard Mater 124 (2005), 27-33.
24. M.H. Keshavarz and M. Jaafari, Investigation of the various structure parameters for predicting impact sensitivity of energetic molecules via artificial neural network, Propel Explos Pyrotechn 31 (2006), 216-225.
25. M.H. Keshavarz, H.R. Pouretedal, and A. Semnani, Novel correlation for predicting impact sensitivity of nitroheterocyclic energetic molecules, J Hazard Mater 141 (2007), 803-807.
26. M.H. Keshavarz, Prediction of impact sensitivity of nitroaliphatic, nitroaliphatic containing other functional groups and nitrate explosives, J Hazard Mater 148 (2007), 648-652.
27. M.J. Kamlet, The Relationship of Impact Sensitivity with Structure of Organic High Explosives. I. Polynitroaliphatic Explosives, Sixth Symposium (International) on Detonation, Coronads, CA, (1976), pp. 69-72.
28. M.J. Kamlet and H.G. Adolph, The relationship of impact sensitivity with structure of organic high explosives. II. Polynitroaromatic explosives, Propel Explos 4 (1979), 30-34.
29. B.M. Rice and J.J. Hare, A quantum mechanical investigation of the relation between impact sensitivity and the charge distribution in energetic molecules, J Phys Chem A 106 (2002), 1770-1783.
30. B.M. Rice, S. Sahu, and F.J. Owens, Density functional calculations of bond dissociation energies for NO2 scission in some nitroaromatic molecules, J Mol Struct (THEOCHEM) 583 (2002), 69-72.
31. J. Gasteiger and J. Zupan, Neural networks in chemistry, Angew Chem Int Ed Engl 32 (1993), 503-527.
32. R. Leardi, Genetic algorithms in chemometrics and chemistry: A review, J Chemometr 15 (2001), 559-569.
33. M. Karelson, Molecular Descriptors in QSAR/QSPR, Wiley, New York, 2000.
34. M. Karelson, V.S. Lobanov, and A.R. Katritzky, Quantum-chemical descriptors in QSAR/QSPR studies, Chem Rev 96 (1996), 1027-1044.
35. C. Adamo and V. Barone, Toward reliable density functional methods without adjustable parameters: The PBE0 model, J Chem Phys 110 (1999), 6158-6170.
36. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, J.A. Montgomery, T. Vreven, K.N. Kudin, J.C. Burant, J.M. Millam, S.S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G.A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J.E. Knox, H.P. Hratchian, J.B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, P.Y. Ayala, K. Moro-kuma, G.A. Voth, P. Salvador, J.J. Dannenberg, V.G. Zakrzewski, S. Dapprich, A.D. Daniels, M.C. Strain, O. Farkas, D.K. Malick, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J.V. Ortiz, Q. Cui, A.G. Baboul, S. Clifford, J. Cioslowski, B.B. Stefa-nov, G. Liu, A. Liashenko, P. Piskorz, I. Komar-omi, R.L. Martin, D.J. Fox, T. Keith, M.A. Al-Laham, C.Y. Peng, A. Nanayakkara, M. Challa-combe, P.M.W. Gill, B. Johnson, W. Chen, M.W. Wong, C. Gonzalez, and J.A. Pople, Gaussian03, Gaussian Inc., Wallington CT, 2004.
37. M.J.S. Dewar, E.G. Zoebisch, E.F. Healy, and J.J.P. Stewart, Development and use of quantum mechanical molecular models. 76. AM1: A new general purpose quantum mechanical molecular model, J Am Chem Soc 107 (1985), 3902-3909.
38. Hyperchem 7.0, Hypercube Inc., Gainesville, 2002
39. A.R. Katritzky, R. Petrukhin, R. Jain, and M. Karelson, QSPR analysis of flash points, J Chem Inf Comput Sci 41 (2001), 1521-1530.
40. A.R. Katritzky, I.B. Stoyanova-Slavova, D.A. Dobchev, and M. Karelson, QSPR modeling of flash points: An update, J Mol Graph Model 26 (2007), 529-536.
41. A.R. Katritzky, L. Pacureanu, D. Dobchev, and M. Karelson, QSPR study of critical micelle concentration of anionic surfactants using computational molecular descriptors, J Chem Inf Model 47 (2007), 782-793.
42. A.R. Katritzky, S.H. Slavov, D.A. Dobchev, and M. Karelson, Rapid QSPR model development technique for prediction of vapor pressure of organic compounds, Comput Chem Eng 31 (2007) ,1123-1130.
43. CodessaPro, University of Florida, 2002.
44. T. Grewer, Thermal Hazards of Chemical Reactions, Elsevier, Amsterdam, 1994.
45. L.J.O. Figueiredo and F.M.S. Garrido, Chemomet-ric analysis of nonlinear optical chromophores structure and thermal stability, J Mol Struct (THE-OCHEM) 539 (2001), 75-81.
46. X. Yu, Z. Xie, B. Yi, X. Wang, and F. Liu, Prediction of the thermal decomposition property of polymers using quantum chemical descriptors, Eur Polym J 43 (2007), 818-823.
47. M.C. Kroon, W. Buijs, C.J. Peters, and G.-J. Wit-kamp, Quantum chemical aided prediction of the thermal decomposition mechanisms and temperatures of ionic liquids, Thermochim Acta 465 (2007), 40-47.
48. T. Grewer, The influence of chemical structure on exothermic decomposition, Thermochim Acta 187 (1991), 133-149.
49. E. Theerlynck, D. Mathieu, and P. Simonetti, Towards improved models to rationalize and estimate the decomposition temperatures of nitroal-kanes, nitramines and nitric esters, Thermochim Acta 426 (2005), 123-129.
50. S.R. Saraf, W.J. Rogers, and M.S. Mannan, Application of transition state theory for thermal stability prediction, Ind Eng Chem Res 42 (2003), 1341-1346.
51. M.H. Keshavarz, Simple method for prediction of activation energies of the thermal decomposition of nitramines, J Hazard Mater 162 (2009), 1557-1562.
52. M.H. Keshavarz, H.R. Pouretedal, A. Shokrolahi, A. Zali, and A. Semnani, Predicting activation energy of thermolysis of polynitro arenes through molecular structure, J Hazard Mater 160 (2008), 142-147.
53. Y.S. Duh, C. Lee, C.C. Hsu, D.R. Hwang, and C.S. Kao, Chemical incompatibility of nitrocom-pounds, J Hazard Mater 53 (1997), 183-194.
54. G. Fayet, P. Rotureau, L. Joubert, and C. Adamo, On the prediction of thermal stability of nitroaromatic compounds using quantum chemical calculations, J Hazard Mater 171 (2009), 845-850.
55. G. Fayet, L. Joubert, P. Rotureau, and C. Adamo, On the use of descriptors arising from the conceptual density functional theory for the prediction of chemicals explosibility, Chem Phys Lett 467 (2009), 407-411.
56. E.S. Shanley and G.A. Melhem, The oxygen balance criterion for thermal hazards assessment, Process Saf Prog 14 (1995), 29-31.
57. M.H. Keshavarz, Theoretical prediction of electric spark sensitivity of nitroaromatic energetic compounds based on molecular structure, J Hazard Mater 153 (2008), 201-206.
58. G. Fayet, P. Rotureau, L. Joubert, and C. Adamo, QSPR modeling of thermal stability of nitroaromatic compounds: DFT vs. AM1 calculated descriptors. J Mol Model. (in press).
59. S. Zeman, "A study of chemical micro-mechanisms of initiation of organic polynitro compounds, Energetic Materials. Part 2: Detonation, Combustion," P. Politzer and J. S. Murray, (Editors), Elsevier, Amsterdam (2003), pp. 25-52.
60. F. Hosoya, K. Shiino, and K. Itabashi, Electric-spark sensitivity of heat-resistant polynitroaromatic compounds, Propel Explos Pyrotechn 16 (1991), 119-122.
61. S. Zeman, V. Pelikan, and J. Majzlik, Electric spark sensitivity of nitramines. Part I. Aspects of molecular structure, Centr Eur J Energ Mat 3 (2006), 27-44.
62. V. Zeman, J. Koci, and S. Zeman, Electric spark sensitivity of polynitro compounds: Part III. A correlation with detonation velocities of some nitramines, HanNeng Cailiao 7 (1999), 172-175.
63. G. Wang, H. Xiao, X. Ju, and X. Gong, Calculation of detonation velocity, pressure and electric spark sensitivity of nitro arenas based on quantum chemistry, Propel Explos Pyrotechn 31 (2006), 361-368.
64. M.H. Keshavarz, H.R. Pouretedal, and A. Semnani, Reliable prediction of electric spark sensitivity of nitramines: A general correlation with detonation pressure, J Hazard Mater 167 (2009), 461-466.