Explosives Engineering - Paul Cooper - E-Book

Explosives Engineering E-Book

Paul Cooper

0,0
194,99 €

-100%
Sammeln Sie Punkte in unserem Gutscheinprogramm und kaufen Sie E-Books und Hörbücher mit bis zu 100% Rabatt.
Mehr erfahren.
Beschreibung

This graduate text, and Cooper's companion introductory text ('Introduction to the Technology of Explosives'), serve the same markets as the successful explosives reference by Meyer, now in its 4th edition. VCH also published the International Journal of Propellants, Explosives, and Pyrotechnics. The resulting package would give VCH the major presence in the field. This text presents the basic technologies used in the engineering of explosives and explosive systems, i.e., chemistry, burning, detonation, shock waves, initiation theories, scaling. The book is written for upper-division undergraduate or graduate-level scientists and engineers, and assumes a good grasp of basic physics, chemistry, mechanics and mathematic through calculus. It is based on lecture notes used for graduate courses at the Dept. of Energy Laboratories, and could serve as a core text for a course at schools of mining or military engineering. The intent of the book is to provide the engineer or scientist in the field with an understanding of the phenomena involved and the engineering tools needed to solve/ design/ analyze a broad range of real problems.

Sie lesen das E-Book in den Legimi-Apps auf:

Android
iOS
von Legimi
zertifizierten E-Readern

Seitenzahl: 571

Veröffentlichungsjahr: 2018

Bewertungen
0,0
0
0
0
0
0
Mehr Informationen
Mehr Informationen
Legimi prüft nicht, ob Rezensionen von Nutzern stammen, die den betreffenden Titel tatsächlich gekauft oder gelesen/gehört haben. Wir entfernen aber gefälschte Rezensionen.



Contents

Cover

Title page

Copyright page

Dedication

Preface

Section I: Chemistry of Explosives

Chapter 1: Organic Chemical Nomenclature

1.1 Basic Organic Structures

1.2 Alkanes

1.3 Alkenes

1.4 Alkynes

1.5 Cyclic Forms

1.6 Aromatics

1.7 Polycyclic Aromatic Structures

Chapter 2: Oxidation

2.1 Oxidation Reactions

2.2 Effects of Stoichiometry

2.3 Reaction Product Hierarchy

2.4 Oxygen Balance

Chapter 3: Pure Explosives

3.1 Grouping Explosives by Structure

3.2 Aromatic Pure Explosive Compounds

3.3 Aliphatic Explosive Compounds

3.4 Inorganic Explosives

Chapter 4: Use Forms of Explosives

4.1 Pressings

4.2 Castables

4.3 Plastic Bonded (PBX)

4.4 PUTTIES

4.5 Rubberized

4.6 Extrudables

4.7 Binary

4.8 Blasting Agents

4.9 Slurries and Aqueous Gels

4.10 Dynamites

Chapter 5: Estimating Properties of Explosives

5.1 Estimation of Theoretical Maximum Density

5.2 Estimation of Detonation Velocity AT TMD

5.3 Detonation Velocity as a Function of Density

5.4 Estimating Detonation Velocity of Mixtures

5.5 Estimating Detonation Pressure

Chapter 6: Decomposition

6.1 Decomposition Reactions

6.2 Thermal Stability Tests

6.3 Chemical Compatibility

References

Section II: Energetics of Explosives

Chapter 7: Basic Terms of Thermodynamics

7.1 Energy

7.2 Temperature and Heat

7.3 Internal Energy

7.4 Energy in Transition: Heat and Work

7.5 Energy Units

7.6 Enthalpy

Chapter 8: Thermophysics

8.1 Heat Capacity of Gases

8.2 Heat Capacity of Liquids

8.3 Heat Capacity of Solids

8.4 Latent Heat of Fusion

8.5 Heat of Vaporization

8.6 Heat of Transition

8.7 Summary

Chapter 9: Thermochemistry

9.1 Heat of Reaction

9.2 Heat of Formation

9.3 Heats of Reaction from Heats of Formation

9.4 Heat of Combustion

9.5 Heat of Detonation or Explosion

9.6 Heat of Afterburn

Chapter 10: Group Additivity

10.1 Group Additivity Notation

10.2 Data for the Ideal Gas State

10.3 Data for the Solid State

Chapter 11: Reaction Temperature

11.1 Reaction Temperature at Constant Pressure

11.2 Reaction Temperature at Constant Volume

Chapter 12: Closed-Vessel Calculations

12.1 Effect of Free Volume

12.2 Heat Produced

12.3 Temperature of the Gases

12.4 Pressure in the Vessel

12.5 Summary

Chapter 13: Estimating Detonation Properties

13.1 KJ Assumed Product Hierarchy

13.2 Detonation Velocity

13.3 Detonation (CJ) Pressure

13.4 Modifications of the KJ Method

References

Section III: Shock Waves

Chapter 14: Qualitative Description of a Shock Wave

14.1 Stress-Strain

14.2 Sound, Particle, and Shock Velocities

14.3 Attenuation Behind Shock Waves

Chapter 15: The Bead Model

15.1 Arrangement of the Model

15.2 Wave and Particle Velocity

15.3 Energy Partition

15.4 Density Changes

Chapter 16: Rankine-Hugoniot Jump Equations

16.1 Mass Balance

16.2 Momentum Balance

16.3 Energy Balance

Chapter 17: The Hugoniot Planes,

U-u, P-v, P-u

17.1 The Hugoniot

17.2 The

U-u

Plane

17.3 The

P-v

Plane

17.4 The

P-u

Plane

Chapter 18: Interactions of Shock Waves

18.1 Impact of Two Slabs

18.2 Shock at a Material Interface Case a,

Z

A

< Z

B

18.3 Shock at a Material Interface Case b,

Z

A

> Z

B

18.4 Collision of Two Shock Waves

18.5 Summary of Shock Waves and Interactions

Chapter 19: Rarefaction Waves

19.1 Development of a Rarefaction Wave

19.2 Interactions Involving Rarefactions

19.3 Summary of Rarefactions

References

Section IV: Detonation

Chapter 20: Detonations, General Observations

20.1 Simple Theory of Steady Ideal Detonation

20.2 Estimating Detonation Parameters

20.3 Detonation Interactions

20.4 Summary

Chapter 21: Real Effects in Explosives

21.1 The Reaction Zone

21.2 Diameter Effects

21.3 Density Effects

21.4 Temperature Effects

21.5 Geometry Effects (

L/D

)

21.6 Summary

References

Section V: Initiation and Initiators

Chapter 22: Theories of Initiation

22.1 Initiation of Deflagration

22.2 Initiation of Detonation

22.3 Deflagration-to-Detonation Transition

Chapter 23: Nonelectric Initiators

23.1 Flame or Spark Initiators

23.2 Friction-Initiated Devices

23.3 Stab Initiators

23.4 Percussion Initiators

23.5 Energy-Power Relationship

Chapter 24: Hot-Wire Initiators

24.1 Electric Matches

24.2 Electric Blasting Caps

24.3 Short Lead and Connectorized Initiators

24.4 Energy-Power Relationship

24.5 Firing at Minimum Energy

24.6 Safety Considerations in Design

24.7 Quality Control Testing

Chapter 25: Exploding Bridgewire Detonators

25.1 Construction of EBWs

25.2 Explosion of the Bridgewire

25.3 Detonation of Initial Pressing

25.4 Effects of Cables

25.5 Function Time

25.6 Series and Parallel Firing Considerations

25.7 Safety Considerations

References

Section VI: Engineering Applications

Chapter 26: Theories of Scaling

26.1 Units and Dimensions

26.2 Scaling by Geometric Similarity

26.3 Scaling by Dimensional Analysis

26.4 Work Functions or Available Energy

Chapter 27: Acceleration, Formation, and Flight of Fragments

27.1 Acceleration of the Gurney Model

27.2 Fragmentation of Cylinders

27.3 Flight of Fragments

Chapter 28: Blast Effects in Air, Water, and on the Human Body

28.1 Scaling Air Shock

28.2 Scaling Shocks in Water

28.3 Physiological Response to Air Blast

Chapter 29: Scaling Craters

29.1 Crater Formation Mechanisms

29.2 Surface Bursts

29.3 Above-Surface Bursts

29.4 Buried Bursts

Chapter 30: Jetting, Shaped Charges, and Explosive Welding

30.1 Shaped Charges

30.2 Explosive Welding

References

Index

End User License Agreement

Guide

Cover

Copyright

Contents

Begin Reading

Pages

iii

iv

v

vi

vii

viii

ix

1

2

3

4

5

6

7

8

9

10

11

12

13

14

15

16

17

18

19

20

21

22

23

24

25

26

27

28

29

30

31

32

33

34

35

36

37

38

39

40

41

42

43

44

45

46

47

48

49

50

51

52

53

54

55

56

57

58

59

60

61

62

63

64

65

66

67

68

69

70

71

72

73

74

75

76

77

78

79

80

81

82

83

84

85

86

87

88

89

90

91

92

93

94

95

96

97

98

99

100

101

102

103

104

105

106

107

108

109

110

111

112

113

114

115

116

117

118

119

120

121

122

123

124

125

126

127

128

129

130

131

132

133

134

135

136

137

138

139

140

141

142

143

144

145

146

147

148

149

150

151

152

153

154

155

156

157

158

159

160

161

162

163

164

165

166

167

168

169

170

171

172

173

174

175

176

177

178

179

180

181

182

183

184

185

186

187

188

189

190

191

192

193

194

195

196

197

198

199

200

201

202

203

204

205

206

207

208

209

210

211

212

213

214

215

216

217

218

219

220

221

222

223

224

225

226

227

228

229

230

231

232

233

234

235

236

237

238

239

240

241

242

243

244

245

246

247

248

249

250

251

252

253

254

255

256

257

258

259

260

261

262

263

264

265

266

267

268

269

270

271

272

273

274

275

276

277

278

279

280

281

282

283

284

285

286

287

288

289

290

291

292

293

294

295

296

297

298

299

300

301

302

303

304

305

306

307

308

309

310

311

312

313

314

315

316

317

318

319

320

321

322

323

324

325

326

327

328

329

330

331

332

333

334

335

336

337

338

339

340

341

342

343

344

345

346

347

348

349

350

351

352

353

354

355

356

357

358

359

360

361

362

363

364

365

366

367

368

369

370

371

372

373

374

375

376

377

378

379

380

381

382

383

384

385

386

387

388

389

390

391

392

393

394

395

396

397

398

399

400

401

402

403

404

405

406

407

408

409

410

411

412

413

414

415

416

417

418

419

420

421

422

423

424

425

426

427

428

429

430

431

432

433

434

435

436

437

438

439

440

441

442

443

444

445

446

447

448

449

450

451

452

453

454

455

456

457

458

459

460

Explosives Engineering

 

 

Paul W. Cooper

 

 

 

 

 

 

 

The procedures in this text are intended for use only by persons with prior training in the field of explosives. In the checking and editing of these procedures, every effort has been made to identify potentially hazardous steps and safety precautions have been inserted where appropriate. However, these procedures must be conducted at one’s own risk. The authors and the publisher, its subsidiaries and distributors, assume no liability and make no guarantees or warranties, express or implied, for the accuracy of the contents of this book or the use of information, methods or products described in this book. In no event shall the authors, the publisher, its subsidiaries or distributors, be liable for any damages or expenses, including consequential damages and expenses, resulting from the use of the information, methods or products described in this book.

 

Paul W. Cooper424 Girard Blvd., SEAlbuquerque, NM 87106

Library of Congress Cataloging-in-Publication Data

Cooper, Paul W., 1937–

       Explosives engineering / Paul W. Cooper.             p. cm.        Includes bibliographical references (p. –) and index.        ISBN 0-471-18636-8 (alk. paper)        1. Explosives. I. Title.   TP270.C7438 1997   662′.2—dc20

Copyright © 1996 Wiley-VCH, Inc.

All rights reserved. Published simultaneously in Canada.

No part of this publication may be reproduced, stored in a retrieval system or transmitted in any form or by any means, electronic, mechanical, photocopying, recording, scanning or otherwise, except as permitted under Sections 107 or 108 of the 1976 United States Copyright Act, without either the prior written permission of the Publisher, or authorization through payment of the appropriate per-copy fee to the Copyright Clearance Center, 222 Rosewood Drive, Danvers, MA 01923, (978) 750-8400, fax (978) 750-4470. Requests to the Publisher for permission should be addressed to the Permissions Department, John Wiley & Sons, Inc., 111 River Street, Hoboken, NJ 07030, (201) 748-6011, fax (201) 748-6008.

Dedicated to my Dad, the late Nathan Cooper, a helluva engineer!

Preface

The field of explosives engineering incorporates a broad variety of sciences and engineering technologies that are brought together to bear on each particular design problem. These technologies include chemistry, thermodynamics, fluid dynamics, aerodynamics, mechanics, electricity, and electronics, and even meteorology, biology, and physiology. Although excellent textbooks and research papers are found in each of these areas, there has been little, if any, literature available that ties all these diverse technologies together into a unified engineering discipline for this complex field of explosives engineering.

The purpose of this text is to attempt to fill that gap. It is based, in large part, upon engineering philosophies and approaches I have developed during my career to solve numerous design problems. The text is broken into six general areas, each of which is bound together by a common technical thread.

Section I deals with the chemistry of explosives. It starts with definitions and nomenclature of organic chemicals, based on molecular structure, which is included to bring nonchemists up to speed on being able recognize and describe pure explosive compounds and mixtures and not to be intimidated by chemists’ jargon. It then describes the many forms in which these explosive chemicals are used. Using molecular structure as the common thread, the text then goes into the estimation of the stoichiometry of oxidation reactions, the prediction of explosive detonation velocity and pressure properties, and the quantitative analysis of thermal stability.

Section II deals with the energetics of explosive reactions: Where does the energy come from, and how much do we get out of a particular explosive reaction? This section also uses molecular structure as the common thread tying together the thermophysical and thermochemical behavior of these reactions. In this section the thermochemical properties of the materials are used to predict the explosive properties.

Section III deals with nonreactive shock waves. The thread here is composed of three simple equations that describe the conservation of mass, momentum, and energy across the shock front. In this section we learn how to deal quantitatively with shock waves interacting with material interfaces and other shock waves.

Section IV combines the thermochemistry from Section II with the shock behavior of Section III to describe detonation (reactive shock waves). This section begins with simple ideal detonation theory and then goes on to quantitative calculations of detonation interactions at interfaces with other materials, and then deals with nonideal effects, those that cannot be predicted by ideal theory, such as the effects of size and geometry.

Section V describes the initiation of explosive reactions and the application of initiation theory to the design and analysis of initiating devices such as nonelectric, hot-wire, and exploding-bridgewire igniters and detonators. The thread that sews together all initiation phenomena is an energy-power balance, which describes the rate at which energy is deposited in an explosive and the rate of energy lost from the explosive through heat transfer.

Section VI takes all the previous information and, hanging that on a common thread of dimensional analysis, goes into the development of design scaling and scaling databases. Scaling theory and data are used here to predict the formation and flight of fragments generated by explosive devices; the production and behavior of air- and water-blast waves; the formation of craters from above-ground, ground-level, and buried explosive charges; the formation of material jetting and how that is applied to the design and behavior of lined cavity-shaped charges, as well as to the process of explosive welding.

Missing from this text is any mention of the computer codes and programs that may be used for the solution of many explosive design problems. That is an intentional omission. This text is intended to give the reader the basic understanding and working tool kit to deal with various explosive phenomena. When computer codes are used, this basic understanding of the phenomena provides a reality check of the output of computer-derived solutions.

Acknowledgments

I wish to acknowledge and thank the following people who helped with bringing this book to completion: Glenda Ponder for the editing and typing and formatting of the original manuscript; Dr. Olden L. Burchett (Sandia National Laboratories, retired), Dr. Brigita M. Dobratz (Lawrence Livermore National Laboratory, retired), and Stanley R. Kurowski (Sandia National Laboratories, retired), who devoted so much time and work in the editing and checking of the final manuscript.

My sincere thanks and appreciation also to the following people who reviewed the manuscripts and provided many excellent comments and improvements: John L. Montoya (Sandia National Laboratories), Dr. Gerald Laib (Naval Surface Warfare Center White Oak), Dr. James E. Kennedy (Los Alamos National Laboratory), Dr. Carl-Otto Lieber (Bundesinstitut fur Chemisch-Technische, BICT, Germany), Dr. Hugh R. James (Atomic Weapons Establishment, England), Dr. Pascal A. Bauer (Professor, Ecole Nationale Superieure de Mecanique et d’Aerotechnique, Paris, France), Dr. Eric J. Rinehart (Field Command, U.S. Defense Nuclear Agency). Mr. J. Christopher Ronay (Institute of Makers of Explosives), and Dr. Ronald Varosh (Reynolds Industries Systems, Inc.).

Paul W. CooperAlbuquerque, NM

SECTION ICHEMISTRY OF EXPLOSIVES

CHAPTER 1Organic Chemical Nomenclature

1.1 Basic Organic Structures

The carbon atom is the basic building block of organic molecules. A brief look at the carbon atom reveals that its atomic number is six, which means that it has six protons in its nucleus and six electrons around its nucleus. Its atomic weight is 12, which means that it must have six neutrons as well as six protons in its nucleus. The first electron shell is complete with two electrons, which leaves four more electrons for the second or outer shell. The second electron shell needs eight electrons to be complete, and thus the carbon atom can either gain or lose four electrons to have a complete outer shell. In other words, the carbon atom has a valence of four. In organic chemicals, the carbon atom fills the outer shell by sharing electrons with other atoms forming shared pairs of electrons or covalent bonds.

The four bonds with which carbon attaches to other atoms are equally distributed in a singly bonded carbon atom. Picture, then, that the bond sites of carbon are like the corners of a tetrahedron. Organic molecules, therefore, are three dimensional. Because it is difficult to draw complex, three-dimensional figures, we represent organic molecules by convention with a two-dimensional system of notation.

Carbon, with nothing bonded to it, is represented in Figure 1.1(a). Each dot represents one of the four electrons in the outer shell. Carbon can share its electrons with the electrons of other carbon atoms to form complex chains. If there is one shared pair of electrons between two carbon atoms, it is a single bond [Figure 1.1(b)]. Each shared pair of electrons can also be represented by a line. If there are two shared pairs of electrons between two carbon atoms, it is called a double bond [Figure 1.1(c)]. A triple bond, shown in Figure 1.1(d), consists of three shared pairs of electrons between two carbon atoms.

Figure 1.1. (a) Carbon; (b) single-bonded carbons; (c) double-bonded carbons; and (d) triple-bonded carbons.

If all the remaining electrons each form a covalent bond by sharing with the electron of a hydrogen atom (hydrogen has one available electron to form a covalent bond), then a molecule of hydrogen and carbon, or a hydrocarbon, is formed. Some examples are shown in Figure 1.2. Remember that in stable organic molecules, carbon has four covalent bonds and hydrogen has one.

Figure 1.2. Three simple hydrocarbon molecules.

1.2 Alkanes

Hydrocarbon molecules in which the carbon atoms are attached to each other only by means of single bonds are called saturated. Open-chain, saturated hydrocarbons form the group called alkanes, shown in Figure 1.3. Their names all end with the suffix ane.

Figure 1.3. Alkanes (saturated hydrocarbons): (a) methane, (b) ethane, (c) propane, and (d) butane.

The names of the four hydrocarbons of the alkane chains shown in Figure 1.3 are derived from the Latin named numbers as shown in Table 1.1. If one bond is not attached to hydrogen, thus leaving it open to attach to some other atom, the name can end with yl, instead of ane. Two different structures of butylbromide are shown in Figure 1.4(a) and (b). Each carbon in the chain is numbered starting from the end nearest the heteroatom.

Figure 1.4. (a)–(c) Butylbromide.

Table 1.1 Alkanes

Carbons in Chain

Name

  1

Methane

  2

Ethane

  3

Propane

  4

Butane

  5

Pentane

  6

Hexane

  7

Heptane

  8

Octane

  9

Nonane

10

Decane

11

Undecane

12

Dodecane

13

Tridecane

14

Tetradecane

15

Pentadecane

16

Hexadecane

17

Heptadecane

18

Octadecane

19

Nonadecane

Note that a shorthand version of the structure, -CHx, can be used where there is no ambiguity caused; thus the 1-butylbromide in Figure 1.4(a) could be written as shown in (c). The ending ane can also be retained, as shown in the same two structures of bromobutane in Figure 1.5.

Figure 1.5. (a) 1-Bromobutane; (b) 2-bromobutane.

If another shorter alkane is attached to one of the nonterminal carbons, forming a branched alkane, the longest carbon chain forms the basis of the name, and the attached alkane is the prefix as shown in Figure 1.6. Figure 1.7 shows the structural formula of 2-methyl-2,3-dibromopentane in four steps.

Figure 1.6. 2-Methylpentane (this material is also called isohexane).

Figure 1.7. Structural formula of 2-methyl-2,3-dibromopentane: (a) pentane is the major chain; therefore, there is a straight saturated five-carbon chain as the major backbone; (b) 2-methyl-; there is a methyl group on the number two carbon; (c) -2,3-dibromo; dibromo means two bromine atoms, and they are on the number 2 and 3 carbons; (d) the rest of the bonds are not specified; therefore, they are all bonded to hydrogen; thus we have 2-methyl-2,3-dibromopentane.

1.3 Alkenes

If there are one or more double bonds in a hydrocarbon, it is unsaturated. Unsaturated, straight-chain hydrocarbons with one double bond are called alkenes. Their names are identical to the alkanes, except they end with ene instead of ane. An example is shown in Figure 1.8. If there are two double bonds, the chain is called an alkadiene, and the names end in adiene, instead of ene. An example is given in Figure 1.9.

Figure 1.8. 2-Pentene.

Figure 1.9. 1,4-Hexadiene.

If three double bonds exist, the group is called alkatrienes, with the names ending in atriene. Exceptions are the compounds ethylene (CH2=CH2) and allene (CH2=C=CH2), which retain their common names.

1.4 Alkynes

When there is a triple bond in the chain, it is referred to as an alkyne. The names end with yne instead of ane, but otherwise are named similarly to the alkanes and alkenes. Chains with multiple triple bonds are likewise called alkadiynes, with names ending in adiyne; alkatriynes, with names ending in atriyne; and so forth. The exception is that the compound acetylene (CH≡CH) retains its common name. Unsaturated hydrocarbon chains are numbered starting at the end of the chain that gives the double or triple bonds the lowest numbers. See Figure 1.10.

Figure 1.10. Structural formula of 5,6-dibromo-l,3-hexadiyne: (a) the hexadiyne ending means that the major chain has six carbons and that there are two triple bonds in the chain. Since it is 1,3-hexadiyne, the triple bonds must be between the number 1 and 2 carbons and between the number 3 and 4 carbons. (b) The 5,6-dibromo, of course, indicates two bromine atoms, one each bonded to the number 5 and 6 carbons.

1.5 Cyclic Forms

Most of the chains mentioned with three or more carbons can be bent around and formed into a ring. Such ring compounds are named similarly to the straight chains, except that their name starts with the prefix cyclo. Cyclopropane and cyclohexane are shown in Figure 1.11.

Figure 1.11. (a) Cyclopropane; (b) cyclohexane.

We thus have the families cycloalkanes, cycloalkenes, and cycloalkynes, as well as the multi-double and triple-bond variants such as cycloalkadienes and -atrienes, and cycloalkadiynes, -atriynes, etc. Naming the cyclo compounds corresponds to the naming of the straight-chain forms except that carbon atoms are numbered such that substituents are on the lowest numbered carbon atoms. This is shown in the 1,3,4-tribromo-cyclopentane (Figure 1.12) and in 1,3-cyclohexadiene (Figure 1.13). In the latter case (Figure 1.13), the carbon atoms are numbered so that the double bonds receive the lowest possible numbers. Figure 1.14 shows the structural formula for the compound named 3,5-dibromo-1-cyclopentene.

Figure 1.12. 1,3,4-Tribromo-cyclopentane.

Figure 1.13. 1,3-cyclohexadiene.

Figure 1.14. 3,5-dibromo-1-cyclopentene: (a) the 1-cyclopentene indicates that this is a five-carbon ring with one double bond in it, and that bond is between the number 1 and 2 carbons. (b) 3,5-Dibromo means that there are two bromine atoms, one each bonded to the number 3 and 5 carbons. (c) The rest of the bonds are to hydrogen; thus we have the complete formula.

The compounds we have looked at so far (alkanes, alkenes, and alkynes—open chain or cyclic) are called aliphatic compounds.

1.6 Aromatics

A special ring compound, the six-carbon ring with three double bonds, is known by its common name benzene (Figure 1.15). This particular arrangement has a special stability that makes this ring the basis of a different class of compounds than cycloalkatrienes. All organic compounds that contain this benzene ring are included in a class called aromatic compounds. For simplicity the benzene ring can be represented by the symbol shown in Figure 1.16.

Figure 1.15. The benzene molecule.

Figure 1.16. Symbol for the benzene molecule.

Each corner represents a carbon atom, and if not otherwise indicated, each carbon is bonded to a hydrogen atom. If one hydrogen is removed, the resulting radical is named phenyl and is represented as in Figure 1.17. Therefore, the compound represented in Figure 1.18 is called phenylbromide. If two hydrogen atoms are removed, the resulting diradical is called phenylene. Thus the compound shown in Figure 1.19 is a phenylene-1,3-dibromide, or 1,3-dibromophenylene.

Figure 1.17. Symbol for phenyl, the benzene molecule with one hydrogen removed.

Figure 1.18. Phenylbromide molecule.

Figure 1.19. Phenylene-1,3-dibromide or 1,3-dibromophenylene.

Alternatively, the name benzene may be retained. In that case, this same compound may also be called 1,3-dibromobenzene. The carbons in the benzene ring, like all of the cyclo compounds, are numbered such that the substituents are on the lowest-numbered carbon atoms. In lieu of numbering the carbons, there is also a system of naming relative positions of substitution on the ring when there are two identical substituents. Sometimes this method is clearer to use; however, both the numbering and naming systems are used. If two like substituents are on adjacent carbons of the benzene ring, they are in the ortho form, as in Figure 1.20. If the two substituents are on alternate carbons, they are in the meta position, as shown in Figure 1.21. If the two substituents are on opposite carbons, they are in the para position (Figure 1.22).

Figure 1.20. o-Dibromobenzene (1,2-dibromobenzene).

Figure 1.21. m-Dibromobenzene (1,3-dibromobenzene).

Figure 1.22. p-Dibromobenzene (1,4-dibromobenzene).

The compound of which common moth balls are made is paradichlorbenzene. Certain substituted benzene compounds retain their common names. Some of these are shown in Figure 1.23.

Figure 1.23. (a) Toluene; (b) xylene (o shown); (c) mesitylene; (d) styrene; (e) cumene; and (f) cymene (p shown).

1.7 Polycyclic Aromatic Structures

When more than one benzene ring are in the same compound, they may be joined together in different ways. If both rings share common carbon atoms, they are called fused polycyclics. Examples of this are the compounds shown in Figure 1.24. Since the two common carbons have all four bonds already committed, they are not numbered.

Figure 1.24. Fused polycyclics: (a) naphthalene; (b) anthracene; (c) phenanthrene.

When rings are joined such that they are not sharing common carbon atoms, they are called ring assemblies. Three examples are shown in Figure 1.25.

Figure 1.25. Ring assemblies: (a) biphenyl; (b) p-terphenyl (c) m-terphenyl.

The structural formula of 3, 3′-dichloro-5, 5′-dibromo-byphenyl is shown in Figure 1.26.

Figure 1.26. 3,3′-Dichloro-5,5′-dibromobiphenyl. (a) Biphenyl (a two-ring assembly); (b) 3,3′-dichloro indicates two chlorine atoms, one each on the number 3 and 3′ carbons; (c) 5,5′-dibromo indicates two bromines, one each on the number 5 and 5′ carbons.

For more extensive rules in organic chemical nomenclature, consult Ref. 1.

CHAPTER 2Oxidation

2.1 Oxidation Reactions

When explosives react they produce energy by a process called oxidation. In this chapter we will examine this process and see how it is affected by the composition of the explosive. We will learn how to predict the composition of the products of oxidation and how to quantify the degree of oxidation.

An oxidation reaction is the chemical reaction that occurs when a fuel is burning or an explosive is detonating; it is the same in both cases. Oxidation reactions produce heat because the internal energy of the product (final) molecules is lower than the internal energy of the reactant (starting) molecules. This difference between the internal energies of the reactants and products is called the heat of reaction.