Predictive Models for Thermal Stability and Explosive Properties of Chemicals from Molecular Structure

Industrial chemical processes may involve thermal risks as most of the reactions performed are exothermic, the chemicals used are often thermally unstable, and the operating conditions are set to induce high conversion and throughput. Besides the reactive steps, all operations from mixing to storage and from processing to transport involving sensitive chemicals should be conducted under strictly controlled conditions ensuring safe operations. Performing an efficient risk assessment and implementing the proper risk mitigation measures are essential to avoid, or at least reduce, accidents and their potentially disastrous consequences. For optimal design and implementation of safety measures, it is important that these considerations are taken into account at early stages of process development. The required data should be made available at the appropriate time so it can be properly accounted for and efficiently serve the design. Yet, at early design phases, some information may be unavailable due to several reasons: the process design being still in development, some parameters can be unknown; experimental analysis of chemicals could be hindered or impossible due to products availability in required quantities; several alternatives are under investigation which raises the necessary resources (time and material) for experimental tests. Predictions would be the appropriate response to such scenario. The aim of this dissertation is to develop predictive models for two hazardous behaviors of chemicals: explosive sensitivity and thermal stability. For the models to be applicable at early development phases, it is preferable to minimize the information feed requirements, and therefore, structure-based approaches are applied. Two methods were identified: Quantitative Structure-Property Relationships (QSPR) and Group Contributions Method (GCM). The hazardous behaviors are studied through characteristic measurements: the Minimal Ignition Energy (MIE) to represent explosive sensitivity and Differential Scanning Calorimetry (DSC) for thermal stability. These measurements are widely employed in safety studies and deliver necessary information to identify potential hazards. Moreover, their specificities call for predictive models: MIE tests require repetitive analysis and hence are time and material consuming; regarding DSC experiments, experts have noted that they seem to exhibit structurally dependent features, and so far no study has comprehensively investigated this phenomenon. This work presents in a first part the structure-based approaches that are applied and the elements of Data Analysis necessary for developing predictive models and simulating experimental results. Secondly, both experimental analysis are detailed and the important information our models should be able to represent will be exposed. Finally, the third and last part is dedicated to the applications: the obtained predictive models are presented, evaluated and discussed. Most of the initial objectives are met as efficient solutions are proposed, nonetheless, some improvement strategies may also be considered.

[1]  P. Rotureau,et al.  QSPR modeling of thermal stability of nitroaromatic compounds: DFT vs. AM1 calculated descriptors , 2010, Journal of molecular modeling.

[2]  S. L. Boersma,et al.  A Theory of Differential Thermal Analysis and New Methods of Measurement and Interpretation , 1955 .

[3]  C. Hansch,et al.  Structure--activity correlations in the metabolism of drugs. , 1968, Archives of biochemistry and biophysics.

[4]  Z. Friedl,et al.  Electric Spark Sensitivity of Nitramines. Part I. Aspects of Molecular Structure , 2006 .

[5]  Yong Pan,et al.  Predicting the auto-ignition temperatures of organic compounds from molecular structure using support vector machine. , 2009, Journal of hazardous materials.

[6]  Takahiro Suzuki,et al.  Quantitative Structure-Property Relationships for Auto-Ignition Temperatures of Organic Compounds , 1994 .

[7]  M. Keshavarz Simple method for prediction of activation energies of the thermal decomposition of nitramines. , 2009, Journal of hazardous materials.

[8]  Raúl Rojas,et al.  Neural Networks - A Systematic Introduction , 1996 .

[9]  Michael L. Mavrovouniotis,et al.  Estimation of Properties of Acyclic Organic Compounds Using Conjugation Operators , 1994 .

[10]  Heinz Haase Electrostatic Hazards: Their Evaluation and Control , 1976 .

[11]  E. Pardillo-Fontdevila,et al.  Estimation of pure compound properties using group‐interaction contributions , 1999 .

[12]  J. Stewart Optimization of parameters for semiempirical methods I. Method , 1989 .

[13]  J. Dodge,et al.  Structure/activity relationships , 1998 .

[14]  Paolo Grillo,et al.  Cancer incidence in the population exposed to dioxin after the "Seveso accident": twenty years of follow-up , 2009, Environmental health : a global access science source.

[15]  Aage Fredenslund,et al.  Vapor−Liquid Equilibria by UNIFAC Group Contribution. 6. Revision and Extension , 1979 .

[16]  Mohammad Hossein Keshavarz,et al.  Relationship between thermal stability and molecular structure of polynitro arenes , 2009 .

[17]  H. Akaike A new look at the statistical model identification , 1974 .

[18]  Yong Pan,et al.  Prediction of flammability characteristics of pure hydrocarbons from molecular structures , 2009 .

[19]  W. A. Sexton,et al.  STRUCTURE—ACTIVITY RELATIONSHIPS , 1958, The Journal of pharmacy and pharmacology.

[20]  J. Devillers,et al.  Practical applications of quantitative structure-activity relationships (QSAR) in environmental chemistry and toxicology , 1990 .

[21]  Lockwood,et al.  Thermal stability of the , 1992, Physical review. B, Condensed matter.

[22]  Cheng Xin-lu,et al.  Neural networks study on the correlation between impact sensitivity and molecular structures for nitramine explosives , 2006 .

[23]  Patricia Rotureau,et al.  Predicting the Thermal Stability of Nitroaromatic Compounds Using Chemoinformatic Tools , 2011, Molecular informatics.

[24]  G. Schwarz Estimating the Dimension of a Model , 1978 .

[25]  G. Höhne,et al.  Calorimetry: Fundamentals, Instrumentation and Applications , 2014 .

[26]  S. Sarge Determination of characteristic temperatures with the scanning calorimeter , 1991 .

[27]  E. Gmelin,et al.  Calibration of differential scanning calorimeters , 1995 .

[28]  Alan R. Katritzky,et al.  Quantum-Chemical Descriptors in QSAR/QSPR Studies , 1996 .

[29]  I. Eckerman,et al.  The Bhopal Saga—Causes and Consequences of the World's Largest Industrial Disaster , 2005, Prehospital and Disaster Medicine.

[30]  Edward S. Blake,et al.  Thermal Stability as a Function of Chemical Structure. , 1961 .

[31]  T. A. Albahri Flammability characteristics of pure hydrocarbons , 2003 .

[32]  B. K. Harrison,et al.  Prediction of thermal hazards of chemical reactions , 1999 .

[33]  Yong Pan,et al.  QSPR Study on Electric Spark Sensitivity of Nitro Arenes , 2011 .

[34]  Dennis J. Beal SAS Code to Select the Best Multiple Linear Regression Model for Multivariate Data Using Information Criteria , 2005 .

[35]  Hassan Golmohammadi,et al.  Evaluations of thermal decomposition properties for optically active polymers based on support vector machine , 2014, Journal of Thermal Analysis and Calorimetry.

[36]  Rafiqul Gani,et al.  Molecular structure based estimation of properties for process design , 1996 .

[37]  Gürkan Sin,et al.  Group-contribution+ (GC+) based estimation of properties of pure components: Improved property estimation and uncertainty analysis , 2012 .

[38]  W. Kohn,et al.  Self-Consistent Equations Including Exchange and Correlation Effects , 1965 .

[39]  P. Rotureau,et al.  A General Guidebook for the Theoretical Prediction of Physicochemical Properties of Chemicals for Regulatory Purposes. , 2015, Chemical reviews.

[40]  T. Grewer The influence of chemical structure on exothermic decomposition , 1991 .

[41]  Tareq A. Albahri,et al.  MNLR and ANN structural group contribution methods for predicting the flash point temperature of pure compounds in the transportation fuels range , 2015 .

[42]  P. Walmsley,et al.  Statistical Method , 1923, Nature.

[43]  Marcia L. Harris,et al.  Participation of large particles in coal dust explosions , 2014 .

[44]  The Correlation between Electric Spark Sensitivity of Polynitroaromatic Compounds and Their Molecular Electronic Properties , 2010 .

[45]  E. Cancès,et al.  Computational quantum chemistry: A primer , 2003 .

[46]  Rajarshi Guha,et al.  On the interpretation and interpretability of quantitative structure–activity relationship models , 2008, J. Comput. Aided Mol. Des..

[47]  M. Keshavarz,et al.  Simple method for reliable predicting flash points of unsaturated hydrocarbons. , 2011, Journal of hazardous materials.

[48]  Juan A. Lazzús,et al.  A group contribution method to predict the thermal decomposition temperature of ionic liquids , 2012 .

[49]  W J Dunn,et al.  Linear relationships between lipophilic character and biological activity of drugs. , 1972, Journal of pharmaceutical sciences.

[50]  Ameet Talwalkar,et al.  Foundations of Machine Learning , 2012, Adaptive computation and machine learning.

[51]  K. Luthman,et al.  Evaluation of dynamic polar molecular surface area as predictor of drug absorption: comparison with other computational and experimental predictors. , 1998, Journal of medicinal chemistry.

[52]  Eli Schwartz,et al.  Regression Analysis And Forecasting Models , 2007 .

[53]  V. Buss,et al.  Quantum-mechanically calculated properties for the development of quantitative structure-activity relationships (QSAR'S). pKA-values of phenols and aromatic and aliphatic carboxylic acids , 1989 .

[54]  Vytenis Babrauskas Ignition Handbook: Principles and Applications to Fire Safety Engineering, Fire Investigation, Risk Management and Forensic Science , 2003 .

[55]  J. Flynn The isoconversional method for determination of energy of activation at constant heating rates , 1983 .

[56]  Attila Felinger,et al.  Data Analysis and Signal Processing in Chromatography , 2011 .

[57]  Lemont B. Kier,et al.  Electrotopological State Indices for Atom Types: A Novel Combination of Electronic, Topological, and Valence State Information , 1995, J. Chem. Inf. Comput. Sci..

[58]  J. Pople,et al.  Approximate Self‐Consistent Molecular Orbital Theory. III. CNDO Results for AB2 and AB3 Systems , 1966 .

[59]  C. Russom,et al.  QSAR modelling of the ERL-D fathead minnow acute toxicity database. , 1991, Xenobiotica; the fate of foreign compounds in biological systems.

[60]  M. Abdelghani-Idrissi,et al.  Kinetic parameter estimation for decomposition of organic peroxides by means of DSC measurements , 2011 .

[61]  H. Calcote,et al.  Spark Ignition. Effect of Molecular Structure. , 1952 .

[62]  J. F. Liebman,et al.  Enthalpies of vaporization of some highly branched hydrocarbons , 1995 .

[63]  H. Koseki,et al.  Thermal decomposition kinetic of liquid organic peroxides , 2005 .

[64]  N. S. Ostlund,et al.  Approximate self-consistent molecular orbital theory of nuclear spin coupling. V. Proton-proton coupling constants in substituted benzenes , 1970 .

[65]  Zhen-hua Chen,et al.  Predicting the thermal stability of RE-based bulk metallic glasses , 2010 .

[66]  C. Selassie,et al.  History of Quantitative Structure–Activity Relationships , 2010 .

[67]  Aage Fredenslund,et al.  A modified UNIFAC group-contribution model for prediction of phase equilibria and heats of mixing , 1987 .

[68]  Wolfgang Bartknecht,et al.  Explosions, course, prevention, protection , 1981 .

[69]  Nasser M. Nasrabadi,et al.  Pattern Recognition and Machine Learning , 2006, Technometrics.

[70]  Martin Glor,et al.  Ignition hazard due to static electricity in particulate processes , 2003 .

[71]  S. Hada,et al.  Prediction of energy release hazards using a simplified adiabatic temperature rise , 2007 .

[72]  M. Mannan,et al.  Prediction of the Reactivity Hazards for Organic Peroxides Using the QSPR Approach , 2011 .

[73]  G. Höhne,et al.  Differential Scanning Calorimetry , 2007 .

[74]  Trevor Kletz Chapter 1 – Preparation for Maintenance , 1999 .

[75]  M. J. O'neill,et al.  A Differential Scanning Calorimeter for Quantitative Differential Thermal Analysis. , 1964 .

[76]  David J. Livingstone,et al.  Application of QSPR to Mixtures , 2006, J. Chem. Inf. Model..

[77]  Peter C. Jurs,et al.  Descriptions of molecular shape applied in studies of structure/activity and structure/property relationships , 1987 .

[78]  Stephane Bernard,et al.  Statistical method for the determination of the ignition energy of dust cloud-experimental validation , 2010 .

[79]  Peter C. Jurs,et al.  Prediction of Autoignition Temperatures of Organic Compounds from Molecular Structure , 1997, J. Chem. Inf. Comput. Sci..

[80]  L. McCarty,et al.  The use of quantitative structure-activity relationships to predict the acute and chronic toxicities of organic chemicals to fish , 1985 .

[81]  Trevor Kletz Inherently Safer Design—Its Scope and Future , 2003 .

[82]  Eugene N Muratov,et al.  Universal Approach for Structural Interpretation of QSAR/QSPR Models , 2013, Molecular informatics.

[83]  Jean-Noël Jaubert,et al.  VLE predictions with the Peng–Robinson equation of state and temperature dependent kij calculated through a group contribution method , 2004 .

[84]  E. Homberger,et al.  The Seveso accident: its nature, extent and consequences. , 1979, The Annals of occupational hygiene.

[85]  H. Golmohammadi,et al.  Quantitative structure–property relationship studies of gas-to-wet butyl acetate partition coefficient of some organic compounds using genetic algorithm and artificial neural network , 2010 .

[86]  Richard L. Rowley,et al.  Estimation of the flash point of pure organic chemicals from structural contributions , 2010 .

[87]  Jiajia Jiang,et al.  Predicting the net heat of combustion of organic compounds from molecular structures based on ant colony optimization , 2011 .

[88]  Justin Felix,et al.  A universal approach , 2013 .

[89]  A. Albert,et al.  Selective Toxicity , 1973, Springer US.

[90]  A. Leo,et al.  Structure-activity relationships in antitumor aniline mustards. , 1978, Journal of medicinal chemistry.

[91]  Danail Bonchev,et al.  Statistical modelling of molecular descriptors in QSAR/QSPR , 2012 .

[92]  Robert C. Reid,et al.  Estimation of critical properties with group contribution methods , 1984 .

[93]  T. R. Chouhan,et al.  The unfolding of Bhopal disaster , 2005 .

[94]  Kenneth L. Cashdollar,et al.  Explosives dust cloud combustion , 1992 .

[95]  W. C. Lothrop,et al.  The Relationship between Performance and Constitution of Pure Organic Explosive Compounds. , 1949 .

[96]  V. Pareto Manual of Political Economy: A Critical and Variorum Edition , 2014 .

[97]  Iva B. Stoyanova-Slavova,et al.  QSPR modeling of flash points: an update. , 2007, Journal of molecular graphics & modelling.

[98]  Suhani J. Patel,et al.  Prediction models for the flash point of pure components , 2011 .

[100]  J. A. Lazzús Neural network/particle swarm method to predict flammability limits in air of organic compounds , 2011 .

[101]  K. G. Berger,et al.  Some applications of differential thermal analysis to oils and fats , 2007 .

[102]  Stanley S. Grossel Safety considerations in conveying of bulk solids and powders , 1988 .

[103]  P. A. Carson,et al.  4 – Toxic chemicals , 1994 .

[104]  J. Prausnitz,et al.  Correlation of liquid-liquid equilibria for some water-organic liquid systems in the region 20-250.degree.C , 1988 .

[105]  T. Ozawa A New Method of Analyzing Thermogravimetric Data , 1965 .

[106]  T. Ando,et al.  Analysis of differential scanning calorimetric data for reactive chemicals , 1991 .

[107]  M S Mannan,et al.  Prediction of reactive hazards based on molecular structure. , 2003, Journal of hazardous materials.

[108]  Suhani J. Patel,et al.  Quantitative Structure Property Relationship Studies for Predicting Dust Explosibility Characteristics (Kst, Pmax) of Organic Chemical Dusts , 2011 .

[109]  Kazuya Saito,et al.  Base line drawing for the determination of the enthalpy of transition in classical dta, power-compensated dsc and heat-flux dsc , 1986 .

[110]  Eamonn F. Healy,et al.  Development and use of quantum mechanical molecular models. 76. AM1: a new general purpose quantum mechanical molecular model , 1985 .

[111]  G. W. Snedecor Statistical Methods , 1964 .

[112]  Patricia Rotureau,et al.  Predicting explosibility properties of chemicals from quantitative structure‐property relationships , 2009 .

[113]  Zdeňka Kolská,et al.  Group Contribution Methods for Estimation of Selected Physico-Chemical Properties of Organic Compounds , 2012 .

[114]  J. Pople,et al.  Approximate Self‐Consistent Molecular‐Orbital Theory. V. Intermediate Neglect of Differential Overlap , 1967 .

[115]  S. C. Chen,et al.  Approximate Self‐Consistent Molecular Orbital Theory II. CNDO‐MO Calculation of Methane Chlorine Derivatives , 1975 .

[116]  L. Angelini,et al.  Statistical Physics and the Clustering Problem , 2004 .

[117]  M. Brandsch,et al.  Three-dimensional quantitative structure-activity relationship analyses of peptide substrates of the mammalian H+/peptide cotransporter PEPT1. , 2003, Journal of medicinal chemistry.

[118]  P. Rotureau,et al.  Global and local quantitative structure–property relationship models to predict the impact sensitivity of nitro compounds , 2012 .

[119]  G. A. Melhem,et al.  A review of ASTM CHETAH 7.0 hazard evaluation criteria , 1995 .

[120]  Jules J. Berman,et al.  Principles of Big Data: Preparing, Sharing, and Analyzing Complex Information , 2013 .

[121]  Jean-Michel Cense,et al.  Prediction of the Impact Sensitivity by Neural Networks , 1996, J. Chem. Inf. Comput. Sci..

[122]  A. Cavallini,et al.  Thermodynamic properties of eight fluorinated olefins , 2010 .

[123]  Mehdi Bagheri,et al.  BPSO-MLR and ANFIS based modeling of lower flammability limit , 2012 .

[124]  F. Gharagheizi Prediction of upper flammability limit percent of pure compounds from their molecular structures. , 2009, Journal of hazardous materials.

[125]  T. Ishii,et al.  The Application of Differential Thermal Analysis to the Study of Reaction Kinetics , 1967 .

[126]  Ian H. Witten,et al.  Data mining - practical machine learning tools and techniques, Second Edition , 2005, The Morgan Kaufmann series in data management systems.

[127]  Jolanta Klos,et al.  Thermal parameters of phenylcarbamic acid derivatives using calculated molecular descriptors with MLR and ANN , 2008 .

[128]  Ian Witten,et al.  Data Mining , 2000 .

[129]  K. Joback,et al.  ESTIMATION OF PURE-COMPONENT PROPERTIES FROM GROUP-CONTRIBUTIONS , 1987 .

[130]  Dongwei Cao Support vector machines and QSAR/QSPR , 2011 .

[131]  D. G. Clark,et al.  Inherently Safer Chemical Processes: A Life Cycle Approach , 1997 .

[132]  W. Bartknecht,et al.  Dust Explosions: Course, Prevention, Protection , 1989 .

[133]  Musa R. Kamal,et al.  Differential scanning calorimetry of epoxy cure: isothermal cure kinetics☆ , 1976 .

[134]  Jorge A. Marrero,et al.  Group-contribution based estimation of pure component properties , 2001 .

[135]  Yong Pan,et al.  Prediction of thermal stability of some reactive chemicals using the QSPR approach , 2014 .

[136]  Yih-Shing Duh,et al.  Chemical incompatibility of nitrocompounds , 1997 .

[137]  Peter C. Jurs,et al.  Estimation of autoignition temperatures of hydrocarbons, alcohols, and esters from molecular structure , 1992 .

[138]  Applicability and limitation of OSARs for the toxicity of electrophilic chemicals. , 2003, Environmental science & technology.

[139]  D. Carson,et al.  MIKE 3 versus HARTMANN apparatus: comparison of measured minimum ignition energy (MIE). , 2008, Journal of hazardous materials.

[140]  John B. Guerard,et al.  Introduction to Financial Forecasting in Investment Analysis , 2013 .

[141]  G. A. Melhem,et al.  On the estimation of hazard potential for chemical substances , 1996 .

[142]  S. Benson,et al.  Additivity Rules for the Estimation of Molecular Properties. Thermodynamic Properties , 1958 .

[143]  Kevin G. Joback Knowledge bases for computerized physical property estimation , 2001 .

[144]  Aage Fredenslund,et al.  Group‐contribution estimation of activity coefficients in nonideal liquid mixtures , 1975 .