Organic Chemistry of Explosives by Robert Hodgson PDF

Organic Chemistry of Explosives pdf

Organic Chemistry of Explosives is the first text to bring together the essential methods and routes used for the synthesis of organic explosives in a single volume.

Assuming no prior knowledge, the book discusses everything from the simplest mixed acid nitration of toluene, to the complex synthesis of highly energetic caged nitro compounds.

  • Reviews laboratory and industrial methods, which can be used to introduce aliphatic C-nitro, aromatic C-nitro, N-nitro, and nitrate ester functionality into organic compounds
  • Discusses the advantages and disadvantages of each synthetic method or route, with scope, limitations, substrate compatibility and other important considerations
  • Features numerous examples in the form of text, reaction diagrams, and tables.

TABLE OF CONTENTS

Foreword.

Preface.

Abbreviations.

Acknowledgements.

Background.

1 Synthetic Routes to Aliphatic C-Nitro Functionality.

1.1 Introduction.

1.2 Aliphatic C-nitro compounds as explosives.

1.3 Direct nitration of alkanes.

1.4 Addition of nitric acid, nitrogen oxides and related compounds to unsaturated bonds.

1.5 Halide displacement.

1.6 Oxidation and nitration of C–N bonds.

1.7 Kaplan–Shechter reaction.

1.8 Nitration of compounds containing acidic hydrogen.

1.9 Oxidative dimerization.

1.10 Addition and condensation reactions.

1.11 Derivatives of polynitroaliphatic alcohols.

1.12 Miscellaneous.

1.13 Chemical stability of polynitroaliphatic compounds.

2 Energetic Compounds 1: Polynitropolycycloalkanes.

2.1 Caged structures as energetic materials.

2.2 Cyclopropanes and spirocyclopropanes.

2.3 Cyclobutanes and their derivatives.

2.4 Cubanes.

2.5 Homocubanes.

2.6 Prismanes.

2.7 Adamantanes.

2.8 Polynitrobicycloalkanes.

3 Synthetic Routes to Nitrate Esters.

3.1 Nitrate esters as explosives.

3.2 Nitration of the parent alcohol.

3.3 Nucleophilic displacement with nitrate anion.

3.4 Nitrate esters from the ring-opening of strained oxygen heterocycles.

3.5 Nitrodesilylation.

3.6 Additions to alkenes.

3.7 Deamination.

3.8 Miscellaneous methods.

3.9 Synthetic routes to some polyols and their nitrate ester derivatives.

3.10 Energetic nitrate esters.

4 Synthetic Routes to Aromatic C-Nitro Compounds.

4.1 Introduction.

4.2 Polynitroarylenes as explosives.

4.3 Nitration.

4.4 Nitrosation–oxidation.

4.5 Nitramine rearrangement.

4.6 Reaction of diazonium salts with nitrite anion.

4.7 Oxidation of arylamines, arylhydroxylamines and other derivatives.

4.8 Nucleophilic aromatic substitution.

4.9 The chemistry of 2,4,6-trinitrotoluene (TNT).

4.10 Conjugation and thermally insensitive explosives.

References.

5 Synthetic Routes to N-Nitro Functionality.

5.1 Introduction.

5.2 Nitramines, nitramides and nitrimines as explosives.

5.3 Direct nitration of amines.

5.4 Nitration of chloramines.

5.5 N-Nitration of amides and related compounds.

5.6 Nitrolysis.

5.7 Nitrative cleavage of other nitrogen bonds.

5.8 Ring-opening nitration of strained nitrogen heterocycles.

5.9 Nitrosamine oxidation.

5.10 Hydrolysis of nitramides and nitroureas.

5.11 Dehydration of nitrate salts.

5.12 Other methods.

5.13 Primary nitramines as nucleophiles.

5.14 Aromatic nitramines.

5.15 The nitrolysis of hexamine.

6 Energetic Compounds 2: Nitramines and Their Derivatives.

6.1 Cyclopropanes.

6.2 Cyclobutanes.

6.3 Azetidines – 1,3,3-trinitroazetidine (TNAZ).

6.4 Cubane–based nitramines.

6.5 Diazocines.

6.6 Bicycles 271

6.7 Caged heterocycles – isowurtzitanes.

6.8 Heterocyclic nitramines derived from Mannich reactions.

6.9 Nitroureas.

6.10 Other energetic nitramines.

6.11 Energetic groups.

7 Energetic Compounds 3: N-Heterocycles.

7.1 Introduction.

7.2 5-Membered rings – 1N – pyrroles.

7.3 5-Membered rings – 2N.

7.4 5-Membered rings – 3N.

7.5 5-Membered rings – 4N.

7.6 6-Membered rings – 1N – pyridines.

7.7 6-Membered rings – 2N.

7.8 6-Membered rings – 3N.

7.9 6-Membered rings – 4N.

7.10 Dibenzotetraazapentalenes.

8 Miscellaneous Explosive Compounds.

8.1 Organic azides.

8.2 Peroxides.

8.3 Diazophenols.

8.4 Nitrogen-rich compounds from guanidine and its derivatives.

References.

9 Dinitrogen Pentoxide – An Eco-Friendly Nitrating Agent.

9.1 Introduction.

9.2 Nitrations with dinitrogen pentoxide.

9.3 The chemistry of dinitrogen pentoxide.

9.4 Preparation of dinitrogen pentoxide.

9.5 C-nitration.

9.6 N-nitration.

9.7 Nitrolysis.

9.8 O-nitration.

9.9 Ring cleavage nitration.

9.10 Selective O-nitration.

9.11 Synthesis of the high performance and eco-friendly oxidizer – ammonium dinitramide.

References.

Index.

REVIEWS – Organic Chemistry of Explosives

“With about 1500 references and many citations leading to existing reviews and further reading, this high quality book is an indispensable reference that should find its place in every good scientific library.” (SYNTHESIS, December 2007)

“…fill[s] a void in the literature by authoring a reference text that provides detailed information on the synthetic routes to a wide variety of energetic materials.” (Journal of Hazardous Metals, July 2007)

ABOUT THE AUTHOR

Jai Prakash Agrawal is the former Director of Materials of the Indian Defence Research and Development Organization. He obtained his PhD in Chemistry from the Gorakhpur University, India, and did postdoctoral work at the University of Saint-Etienne, France, and at the Cavendish Laboratory of the University of Cambridge, UK. In recognition of his achievements Dr. Agrawal was appointed a Fellow of the Royal Society of Chemistry, London.

The focus of his scientific and professional career is on research and development in the field of propellants, explosives and inhibitory materials. He has written a monograph on “Composite Materials” and is recipient of several honours including the prestigious DRDO Technology Award. Together with Robert Hodgson he has authored the book “Organic Chemistry of Explosives”, John Wiley & Sons.

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