An Introduction to Industrial Chemistry

This book is dedicated to the memory of my Father, John Arthur Alan Heaton

An Introduction to Industrial Chemistry

Third edition

Edited by

Alan Heaton Reader in Industrial Chemistry

School of Pharmacy and Chemistry Liverpool John Moores University

SPRINGER-SCIENCE+BUSINESS MEDIA, B.V. IUIlI

First edition 1984 Second edition 1991 This edition 1996

© 1996 Springer Science+Business Media Dordrecht Originally published by Chapman & Hall in 1996

Typeset in 10/12 pt Times by AFS Image Setters Ltd, Glasgow

ISBN 978-0-7514-0272-8 ISBN 978-94-011-0613-9 (eBook) DOI 10.1007/978-94-011-0613-9

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Library of Congress Catalog Card Number: 95-80422

00 Printed on permanent acid-free text paper, manufactured in accordance with ANSIjNISO Z39.48-1992 and ANSIjNISO Z39.48-1984 (Permanence of Paper)

Preface to the Third Edition

Following the success of the first two editions of this book in which the core subject matter has been retained, we have taken the opportunity to add substantial new material, including an additional chapter on that most important activity of the chemical industry, research and development. Topical items such as quality, safety and environmental issues also receive enhanced coverage.

The team of authors for this edition comprises both those revising and updating their chapters and some new ones. The latter's different approach to the subject matter is reflected in the new titles: Organisational Structures - A Story of Evolution (chapter 5) and Environmental Impact of the Chemical Industry (chapter 9). The chapter on Energy retains its original title but different approach of the new authors is evident.

We have updated statistics and tables wherever possible and expanded the index. We hope readers find the brief 'pen pictures' of authors to be interesting.

It is worth stressing again that this book is designed to be used with its companion volume - The Chemical Industry, 2nd Edition, ed. Alan Heaton (referred to as Volume 2) - for a complete introduction to the chemical industry.

Thanks are due to all contributors and to my wife Joy for typing my contributions.

Alan Heaton

Contents

Editorial introduction Alan Heaton

The importance of industrial chemistry Statistics Units and nomenclature General bibliography References

1 Introduction Alan Heaton

1.1 Characteristics of the industry 1.2 Scale of operations 1.3 Major chemical producing countries 1.4 Major sectors and their products 1.5 Turning chemicals into useful end products 1.6 Environmental issues

1.6.1 Flixborough 1.6.2 Minamata Bay (Japan) 1.6.3 Thalidomide and drugs 1.6.4 Seveso, Bhopal and pesticides 1.6.5 Hickson and Weich, Castleford 1.6.6 CFCs (chlorofluorocarbons)

1.7 Quality and safety 1. 7.1 Quality 1. 7.2 Safety

2 Sources of chemicals Alan Heaton

2.1 Introduction 2.2 Sources of organic chemicals

2.2.1 Organic chemicals from oil and natural gas 2.2.2 Organic chemicals from coal 2.2.3 Organic chemicals from carbohydrates (biomass) 2.2.4 Organic chemicals from animal and vegetable oils and fats

2.3 Sources of inorganic chemicals 2.4 Recycling of materials

References Bibliography

3 Research and development Alan Heaton

3.1 General introduction 3.2 Research and development activities

3.2.1 Introduction 3.2.2 Types of industrial research and development 3.2.3 Variations in research and development activities across the

chemical industry 3.3 The importance of research and development

1

1 3 4 5 6

7

8 9

10 10 12 13 13 14 14 15 15 16 17 17 17

19

19 24 25 29 37 40 42 43 44 44

45

45 46 46 47

50 50

viii CONTENTS

3.4 Differences between academic and industrial research 53 3.5 Research and development case studies 54

3.5.1 Vinyl chloride monomer (VCM) 55 3.5.2 CFC replacements 57

3.6 Conclusions 60 Bibliography 61

4 The world's major chemical industries 62 Alan Heaton

4.1 History and development of the chemical industry 62 4.1.1 Origins of the chemical industry 62 4.1.2 Inter-war years, 1918-1939 65 4.1.3 Second World War period, 1939-1945 67 4.1.4 Post-1945 period 67

4.2 The chemical industry today 73 4.2.1 Definition of the chemical industry 73 4.2.2 The need for a chemical industry 74 4.2.3 The major chemicals 76

4.3 The United Kingdom chemical industry 77 4.3.1 Comparison with other U.K. manufacturing industries 77 4.3.2 International comparisons in the chemical industry 80 4.3.3 Major locations of the U.K. chemical industry 83 4.3.4 Some major U.K. chemical companies 84

4.4 The U.S. chemical industry 87 4.5 Other chemical industries 90

4.5.1 Japan 90 4.5.2 Germany 90 4.5.3 France 90 4.5.4 Italy 90 4.5.5 Netherlands 91

4.6 World's major chemical companies 91 4.7 General characteristics and future of the chemical industry 91

4.7.1 General characteristics 91 4.7.2 The future 92

References 94 Bibliography 94

S Organizational structures: A story of evolution 9S Jo McCloskey

5.1 Introduction 95 5.2 The chemical industry in the 1990s 95 5.3 Why change organizational structures? 96 5.4 Pre-structure decisions 97 5.5 Which type of structure? 98

5.5.1 Functional structure 98 5.5.2 Matrix structure 100 5.5.3 Multi-divisional structure 101

5.6 Joint ventures and strategic alliances 106 5.7 Summary 107

References 108

6 Technological economics 109 Derek Bew

6.1 Introduction 109

CONTENTS ix

6.2 Cost of producing a chemical 110 6.3 Variable costs 111

6.3.1 Raw material costs 112 6.3.2 Energy input costs 112 6.3.3 Royalty/licence payments 113 6.3.4 Effect of production rate on variable cost 114 6.3.5 Packaging and transport 114

6.4 Fixed costs 114 6.4.1 Labour charges 115 6.4.2 Depreciation 115 6.4.3 Rates and insurance 116 6.4.4 Overhead charges 116

6.5 Direct, indirect and capital related costs 116 6.6 Profit 117 6.7 Effects of scale operation 118

6.7.1 Variable costs 118 6.7.2 Fixed costs 118 6.7.3 Plant capital 119

6.8 Effect of low rate operation 122 6.8.1 Break-even production rate 125

6.9 Diminishing return 125 6.10 Absorption costing and marginality 126 6.11 Measuring profitability 130

6.11.1 Return on investment 130 6.11.2 Use of inflated capital - current cost accounting 131 6.11.3 Payback time 132 6.11.4 Equivalent maximum invested period 134

6.12 Time value of money 134 6.12.1 Net present value and discounted cash flow 135 6.12.2 Discounted cash flow return 138 6.12.3 Use of NPV and DCF as profitability measures 139

6.13 Project evaluation 140 6.13.1 Comparison of process variable costs 141 6.13.2 Estimation of plant capital 142 6.13.3 Process cost comparison 143 6.13.4 Estimating market/prices 144 6.13.5 Effects of uncertainty 146

6.14 Conclusion 150 Appendix (D.C.F. calculations) 150 References 159 Bibliography 159

7 Chemical engineering 160 Richard Szczepanski

7.1 Introduction 160 7.2 Material balances 160

7.2.1 The flowsheet 160 7.2.2 General balance equation 162 7.2.3 Material balance techniques 164 7.2.4 Multiple unit balances 166 7.2.5 Chemical reactions 168

7.3 Energy balances 176 7.3.1 Energy balance equations 177 7.3.2 Estimation of enthalpy changes 178 7.3.3 Reactive systems 180 7.3.4 Energy balance techniques 181

7.4 Fluid flow 185 7.4.1 Types of fluid 186

x CONTENTS

7.4.2 Flow regimes 7.4.3 Balance equations 7.4.4 Flow in pipes

7.5 Heat transfer 7.5.1 Mechanism 7.5.2 Shell and tube heat exchangers

7.6 Separation processes 7.6.1 Characteristics of separation processes 7.6.2 Phase equilibria 7.6.3 Binary distillation

7.7 Process control 7.7.1 Objectives of process control 7.7.2 The control loop 7.7.3 Measuring devices 7.7.4 The controller 7.7.5 Final control element 7.7.6 Computer control

Appendix References Bibliography

8 Energy Will Bland and Ted Laird

8.1 Introduction 8.1.1 Energy required by the chemical industry 8.1.2 Sources of energy 8.1.3 Cost of energy 8.1.4 Environmental factors 8.1.5 Properties of fuels

8.2 Types of energy 8.2.1 Variation in energy content requirement

8.3 Use of energy in the chemical industry 8.3.1 Batch reactors 8.3.2 Continuous reactors 8.3.3 Electrochemical reactors 8.3.4 Preparation and separation energy 8.3.5 Heat transfer media

8.4 Efficient utilization of energy 8.4.1 Exothermic reactions 8.4.2 Separation processes 8.4.3 Restriction of losses

8.5 Conclusions Appendix References Bibliography

9 Environmental impact of the chemical industry Andrew Hursthouse

187 188 191 200 200 205 210 210 211 213 220 221 222 223 223 226 227 229 231 231

232

232 232 233 235 236 237 238 240 240 240 241 242 242 243 245 245 246 247 248 249 249 250

251

9.1 The environment and human interactions 251 9.2 Sources of pollution 256

9.2.1 Atmospheric pollution 256 9.2.2 Aquatic pollution 259 9.2.3 Land contamination 263

9.3 Options for the control and treatment of pollution and wastes from industrial sites 265 9.3.1 The control of atmospheric discharges 267

9.3.2 The control of aquatic discharges 271 9.3.3 The disposal of solid wastes 274

9.4 Health and safety at work and hazards of the chemical industry 277 9.4.1 Hazards and historical evidence 277 9.4.2 Toxicity and exposure to chemicals 279

9.5 Conclusions - legislative controls affecting the environmental impact of the chemical industry 283

References 285 Bibliography 288

10 Chlor-alkali products Steve Kelham

10.1 Introduction 10.2 Uses of chlorine 10.3 Uses of caustic soda (sodium hydroxide) 10.4 Uses of hydrogen 10.5 Types of cell

10.5.1 Mercury cell process 10.5.2 Diaphragm cell process 10.5.3 Membrane cell process

10.6 Future developments Bibliography

11 Catalysts and catalysis John Pennington

11.1 Introduction 11.2 Definitions and constraints

11.2.1 Essential features 11.2.2 Initiators 11.2.3 Co-reactants 11.2.4 Inhibition

11.3 Thermodynamic relationships 11.3.1 Application 11.3.2 Effect of total pressure 11.3.3 Rough calculations 11.3.4 Thermodynamic traps

11.4 Homogeneous catalysis 11.4.1 General features 11.4.2 Catalyst life and poisons 11.4.3 Limitations

11.5 Heterogenization of homogeneous catalytic systems 11.6 Heterogeneous catalysis

11.6.1 Introduction 11.6.2 Major (primary) and minor (secondary) components 11.6.3 Operational modes 11.6.4 Chemisorption and active sites 11.6.5 Physical forms and their preparation 11.6.6 Support interactions 11.6.7 Catalyst structure 11.6.8 General kinetic behaviour 11.6.9 Catalyst deactivation and life 11.6.10 Studies on surface chemistry 11.6.11 Theoretical approaches

11. 7 Applications and mechanisms 11. 7.1 Introduction 11. 7.2 Acid catalysis

289

289 292 292 292 294 294 298 301 307 308

309

309 310 310 311 311 311 312 312 313 313 314 314 314 315 315 317 319 319 319 320 322 323 324 325 326 327 328 329 331 331 332

CONTENTS xi

xii CONTENTS

11.7.3 Hydrogenation 335 11.7.4 Dual-function catalysis 336 11.7.5 Olefin (alkene) polymerization and dismutation on metals 337 11.7.6 Base catalysis 338 11.7.7 Oxidations 338 11.7.8 Carbon monoxide chemistry 344

11.8 The future 347 References 348 Bibliography 349

12 Petrochemicals John Pennington

350

12.1 Introduction 350 12.1.1 Layout 350 12.1.2 The beginnings 350 12.1.3 Into the 1970s 351 12.1.4 The present 351 12.1.5 Individual feedstocks and routes 352

12.2 Crude oil, gas and refinery operations 353 12.2.1 Crude oil and natural gas 353 12.2.2 Refinery operations 353 12.2.3 Energy consumption 355

12.3 Lower olefins (alkenes) and acetylene (ethyne) 356 12.3.1 Cracking processes 356 12.3.2 Energy balances and economics 359 12.3.3 Lower olefins (alkenes) versus acetylene (ethyne) 364 12.3.4 Polyethylene (polyethene) and polypropylene (polypropene) 366 12.3.5 Production and use statistics 366

12.4 Synthesis gas, ammonia and methanol 368 12.4.1 Process descriptions 368 12.4.2 Energy balances and economics 371 12.4.3 Urea (carbamide), formaldehyde (methanal), amino resins

and polyacetal 373 12.4.4 Production and use statistics 374

12.5 Acetic (ethanoic) acid and anhydride 374 12.5.1 Acetic acid production 374 12.5.2 Acetic anhydride production 377 12.5.3 Production and use statistics 377

12.6 C1 products 378 12.6.1 Formic (methanoic) acid and derivatives 378 12.6.2 Hydrogen cyanide 379 12.6.3 Chloromethanes 379

12.7 C2 products 379 12.7.1 Ethanol 379 12.7.2 Acetaldehyde (ethanal) 380 12.7.3 Ethylene oxide (oxirane) and glycol (ethane-l,2-diol) 381 12.7.4 Vinyl acetate (ethenyl ethanoate) 381 12.7.5 Choroethylenes (chloroethenes) and chloroethanes 382

12.8 C3 products 383 12.8.1 Isopropanol (2-propanol) and acetone (propanone) 383 12.8.2 Propylene oxide (l-methyloxirane) and glycol (propane-l,2-

diol) 383 12.8.3 Acrylonitrile (propenonitrile) 384 12.8.4 Acrylates and acrolein (propenal) 384 12.8.5 Allylic (propenyl) derivatives 385 12.8.6 n-Propanol, propionaldehyde (propanal) and propionic

(propanoic) acid 385

12.9 C4 products 12.9.1 Butenes and butadiene 12.9.2 Sec-butanol (2-butanol) and methyl ethyl ketone

(2-butanone) 12.9.3 Tert-butanol 12.9.4 Maleic anhydride (cis-butanedioic anhydride) 12.9.5 Chloroprene (2-chlorobuta-1,3-diene) 12.9.6 Methacrylates (2-methylpropenoates) 12.9.7 Butyraldehydes (butanals) and primary butanols 12.9.8 C diols and related products

12.10 Cs aliphatics 12.10.1 Isoprene (2-methylbuta-1,3-diene) 12.10.2 Plasticizer alcohols 12.10.3 Detergent intermediates

12.11 Aromatics 12.11.1 Hydrocarbons 12.11.2 Phenol 12.11.3 Benzyls 12.11.4 Nitro-compounds and amines 12.11.5 Phthalic (benzene-1,2-dicarboxylic) anhydride 12.11.6 Terephthalic (benzene-1,4-dicarboxylic) acid

12.12 Nylon intermediates 12.13 The future

12.13.1 The products 12.13.2 Future raw materials and production routes

References Bibliography Periodical special issues and supplement

Index

386 386

386 387 387 388 388 388 389 390 390 390 391 392 392 393 394 394 395 395 396 398 398 399 400 401 402

403

CONTENTS xiii

Contributors

Dr. Derek Bew Formerly of I CI Petrochemicals & Plastics Division, Wilton Derek Bew obtained his M.Sc. in 1951 and Ph.D. in Organic Chemistry in 1954. He then joined ICI's Billingham Division and spent periods in Research and Market Development, Process Development and Plant Management and then in Project Management in the Technical Department. There followed an extended period in the Research and Technology Department working on Process Economics and Evaluation. Derek retired from ICI in 1990.

Dr. Will Bland Department of Chemistry and Applied Chemistry, Kingston University, Penrhyn Road, Kingston-upon-Thames, Surrey KT2IIEE Will Bland worked for three years as a research chemist in industry, obtained his B.Sc. and Ph.D. from the University of Leicester and is currently Acting Associate Head of the School of Applied Chemistry at Kingston University as well as being Course Director of the B.Sc. (Honours) Degree in Environmental Science. His main teaching and research interests are in Industrial Chemistry, Resources and the Environment. He is a Fellow of the Royal Society of Chemistry and a member of the Committee of Tertiary Education Group.

Dr. Alan Heaton School of Pharmacy and Chemistry, Liverpool John Moores University, Byrom Street, Liverpool L4 3AF Alan Heaton worked in the coal-tar chemicals industry as a young man whilst studying for the Grad. R.I.C. qualification. He obtained his Ph.D. in Organofluorine Chemistry at Durham University in 1967. Following a brief spell as Lecturer in Organic Chemistry at the University of Salford, he joined Liverpool Polytechnic in 1969, where he was given responsibility for developing courses in the area oflndustrial Chemistry. He is now Reader in Industrial Chemistry at Liverpool John Moores University and carries out research in the areas of organofluorine chemistry and pesticides.

Since 1971 he has been a Tutor, Tutor Counsellor and Consultant to the Open University. He is a nationally-elected member of the Council of the Royal Society of Chemistry and serves on the Awards Committee of the Society of Chemical Industry as well as being on a number of committees of each of these societies at regional and 10calleve1s.

Dr. Andrew S. Hursthouse Department of Chemistry and Chemical Engineering, University of Paisley, High Street, Paisley P Al 2BE Andrew Hursthouse is a geochemist and a senior lecturer in the Department of Chemistry and Chemical Engineering, University of Paisley. His research interests cover: environmental analysis, the mobility of inorganic and organic species in the environment, the biogeochemistry of metallic and organic compounds and the environmental impact of waste discharges. He has acted as a consultant for industrial and public bodies on a range of environmental problems and manages the Centre for Particle Characterisation and Analysis and R&D, problem solving facility for industry within the Faculty of Science and Technology.

Mr. Steve Kelham Process Development Group, Research and Technology Department, ICI Chemicals and Polymers, PO Box 8, The Heath, Runcorn WA74QD Steve Kelham has had over 20 years of experience of the Chlor-Alkali Industry. He graduated from Cambridge University in 1968 and joined ICI as a Chemical Engineer. He has been primarily involved in process design, plant troubleshooting, commissioning and business development activities linked to chI or-alkali production from mercury, diaphragm and membrane cells at plants around the world. Currently he is managing process development activities within the R&T area in ICI at Runcorn, Cheshire.

Mr. Ted Laird Department of Chemistry and Applied Chemistry, Kingston University, Penrhyn Road, Kingston-upon- Thames, Surrey KT2I 1 EE Ted Laird took his B.Sc. chemistry degree plus his Ph.D. in physical-organic chemistry at Southampton University. After 2 years in the RAF he joined ICI to work in a physical chemistry laboratory. He worked on plant problems at their Wilton Works and then moved on to BNFL to carry out similar work.

He became a chartered chemical engineer and has taught mainly industrial chemistry at Kingston Polytechnic and University for the last 27 years before recently retiring.

xvi CONTRIBUTORS

Mrs. Jo McCloskey Business School, Liverpool John Moores University, 98 Mount Pleasant, Liverpool L3 5UZ Jo McCloskey has studied at universities in Ireland and Scotland. She worked in the public sector before embarking on an academic career. She taught in Ireland and Africa before coming to England. She came to Liverpool Business School after having taught at Leicester Business School. Currently, she is Principal Lecturer and Head of Business Policy and Marketing.

Her research interests and recent publications have been in the areas of environmental management and marketing. She is an experienced marketing and management consultant, having completed various projects in Europe, U.S.A. and Africa.

Mr. John Pennington 4 Bessacarr Avenue, Willerby, Hull HUlO 6JA After graduation and a spell in research at Cambridge University, John Pennington joined the Research and Development laboratories attached to a manufacturing site for bulk organic chemicals near Hull, now owned by BP Chemicals. The work primarily involved factory support and new process development, in both laboratory and pilot plant, but occasionally more speculative research. John progressed in a technical capacity, latterly as a company-wide 'internal consultant' until (early) retirement (at the end of 1988).

Dr. Richard Szczepanski lnfochem Computer Services Ltd., South Bank Technopark, 90 London Road, London SEI 6LN Richard Szczepanski is a director of Infochem Computer Services Ltd., a consultancy specializing in physical property data and software for chemical engineering and petroleum engineering applications. His main area of work is in modelling phase and chemical equilibria. Dr. Szczepanski was formerly a Project Leader at the BP Research Centre and a lecturer in chemical engineering at Imperial College, London.

Conversion factors

1 tonne (metric ton) = 1000 kilograms = 2205 pounds =0·984 tons

1 ton = 1016 kilograms = 2240 pounds = 1·016 tonnes

1 litre = 0·220 gallons (U.K. or Imperial) = 1 cubic metre 1 gallon = 4·546 litres 1 gallon = 1·200 U.S. gallons = 0·00455 cubic metres 1 barrel = 42 U.S. gallons = 35 gallons = 0·159 cubic metres

(Densities of crude oil vary, but 7·5 barrels per tonne is an accepted average figure.)

1 cubic metre = 35·31 cubic feet 1 cubic foot = 0·02832 cubic metres

1 atmosphere = 1·013 bar = 14·696 pounds per square inch = 1·013 X 105 newtons per square metre = 1·013 x 105 pascal

Degrees Centigrade = 0·556 (degrees Fahrenheit - 32) Degrees Fahrenheit = 1·80 (degrees Centigrade) + 32 Degrees Kelvin = degrees Centigrade + 273

1 therm = 100000 British thermal units 1 British thermal unit = 0·252 kilocalories = 1·055 kilojoules 1 kilocalorie = 4·184 kilojoules 1 kilowatt hour = 3600 kilojoules = 859·8 kilocalories

= 3412 British thermal units.

1 horsepower = 0·746 kilowatts 1 kilowatt = 1·34 horsepower

Mass

Volume

Pressure

Temperature

Energy

Power

Nomenclature of organic compounds

Common or trivial Systematic (or IUPAC) name name

Paraffin Alkane Cycloparaffins or

Naphthenes Cycloalkanes Olefins Alkenes Acetylenes Alkynes Methacrylates 2-Methylpropenoates

Ethylene Ethene Propylene Propene

Styrene Phen y lethene

Acetylene Ethyne Isoprene 2-Methylbuta-I,3-diene

Ethylene oxide Oxirane

Propylene oxide I-Methyloxirane

Methyl iodide Iodomethane Methyl chloride Chloromethane Methylene dichloride Dichloromethane Chloroform Trichloromethane Carbon tetrachloride Tetrachloromethane Vinyl chloride Chloroethene Ethylene dichloride I,2-Dichloroethane Allyl chloride 3-Chloropropene Chloroprene 2-Chlorobuta-I,3-diene

Epichlorohydrin l-Chloromethyloxirane

Ethylene glycol Ethane-I,2-diol

Structure

(a) Classes of compounds

CH2=C-C02R I CH 3

CH2=CH 2 (b) Individual compounds CH3CH=CH2

OCH=CH 2

H-C=C-H CH2=C-CH=CH2

I CH3

,.0, CH2-CH2

,.0, CH3-CH-CH2

CH3I CH3CI CH2Cl2

CHCl3 CCl4

CH2=CH-CI CICH2CH 2CI CH2 =CH-CH2-CI CH2=C-CH=CH2

I CI

,.o~ ClCH 2C/l- H2

HOCH 2CH2OH

xx NOMENCLATURE OF ORGANIC COMPOUNDS

Propargyl alcohol Allyl alcohol iso-Propanol

Glycerol

sec-Butanol

Pentaerythritol

Prop-2-yn-I-ol Prop-2-en-I-ol 2-Propanol

Propane-I, 2, 3-triol

2-Butanol

2,2-Di (hydroxymethyl) propane-I,3-diol

Lauryl alcohol Dodecanol Acetone Propanone MethyIisobutyl ketone 4-Methylpentan-2-one

Formaldehyde Acetaldehyde Chloral Propionaldehyde Acrolein Bu tyraldehyde Formic acid Methyl formate Acetic acid Acetic anhydride Peracetic acid Vinyl acetate Acrylic acid Dimethyl oxalate

Propionic acid Methyl methacrylate

Maleic acid

Maleic anhydride

Methanal Ethanal 2,2,2-Trichloroethanal Propanal Propenal Butanal Methanoic acid Methyl methanoate Ethanoic acid Ethanoic anhydride Perethanoic acid Ethenyl ethanoate Propenoic acid Dimethyl ethanedioate

Propanoic acid Methyl

2-methylpropenoate

cis-Butenedioic acid

cis-Butenedioic anhydride

H-C-C-CH20H CH2=CH-CH20H CH3CHCH3

I OH

HOCH2-CH-CH20H I

OH CH3CHCH2CH3

I OH

CH20H I

HOCH2-C-CH20H I

CH20H CH3(CH2)10CH20H CH3COCH3 CH3COCH2CHCH3

I CH3

HCHO CH3CHO Cl3CCHO CH3CH2CHO CH2=CHCHO CH3CH2CH2CHO HC02H HC02CH3

CH3C02H (CH3COhO CH 3C03H CH 2=CH02CCH3

CH2=CH-C02H C02CH3 I C02CH3

CH 3CH 2C02H

H, ~ c-c II '0 c-c'

H/ II o

NOMENCLATURE OF ORGANIC COMPOUNDS XXI

CH2C02H I

Citric acid 2-Hydroxypropane-l, 2, 3- HO-C-C02H tricarboxylic acid I

CH2C02H Methyl laurate Methyl dodecanoate CH3(CH2)10C02CH3 Stearic acid Octadecanoic acid CH3(CH2)16C02H Acrylonitrile Propenonitrile CH2 =CH-CN Adiponitrile Hexane-I,6-dinitrile NC-(CH2)6-CN Urea Carbamide H 2NCONH 2

Ketene Ethenone CH2=C=O

Toluene Methylbenzene 6 Aniline Phenylamine 8

C~l/CH] CH

Cumene iso-Propyl benzene 6 Benzyl alcohol Phenylmethanol 60H

eHl

a-Xylene i,2-Dimethylbenzene (reH]

m-Xylene i,3-Dimethylbenzene & "" CH 1

p-Xylene i,4-Dimethylbenzene Q CH]

Phthalic acid Benzene-i,2-dicarboxylic C0 2H

(re02H

acid

Isophthalic acid Benzene-i,3-dicarboxylic 6 acid "" C02H

Terephthalic acid Benzene-I,4-dicarboxylic ¢" acid

C02 H

xxii NOMENCLATURE OF ORGANIC COMPOUNDS

(c) Additional compounds

o-Toluic acid

p-Toluic acid

p-Tolualdehyde

Benzidine

Furfural

HFA 134a LTBE MTBE TAME

2-Methylbenzoic acid

4-Methylbenzoic acid

4-Methylbenzaldehyde

4,4/ -Biphenyldiamine

2-Formylfuran

1,1,1,2-Tetrafluoroethane Ethyl t-butyl ether Methyl t-butyl ether t-Amyl methyl ether

C02H

(YCHJ

Q" CH l

CHO

¢ cAl

Hl.-OO-NH~

CrCHO

CF3CH2F CH 3CHzOqCH3h CH30 qCH3)3 H3C-C-OCH3

/1 H3C CH2CH3