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. IUIl I

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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 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 1
Alan Heaton
The importance of industrial chemistry 1
Statistics 3
Units and nomenclature 4
General bibliography 5
References 6

1 Introduction 7
Alan Heaton
1.1 Characteristics of the industry 8
1.2 Scale of operations 9
1.3 Major chemical producing countries 10
1.4 Major sectors and their products 10
1.5 Turning chemicals into useful end products 12
1.6 Environmental issues 13
1.6.1 Flixborough 13
1.6.2 Minamata Bay (Japan) 14
1.6.3 Thalidomide and drugs 14
1.6.4 Seveso, Bhopal and pesticides 15
1.6.5 Hickson and Weich, Castleford 15
1.6.6 CFCs (chlorofluorocarbons) 16
1.7 Quality and safety 17
1. 7.1 Quality 17
1. 7.2 Safety 17

2 Sources of chemicals 19
Alan Heaton
2.1 Introduction 19
2.2 Sources of organic chemicals 24
2.2.1 Organic chemicals from oil and natural gas 25
2.2.2 Organic chemicals from coal 29
2.2.3 Organic chemicals from carbohydrates (biomass) 37
2.2.4 Organic chemicals from animal and vegetable oils and fats 40
2.3 Sources of inorganic chemicals 42
2.4 Recycling of materials 43
References 44
Bibliography 44

3 Research and development 45

Alan Heaton
3.1 General introduction 45
3.2 Research and development activities 46
3.2.1 Introduction 46
3.2.2 Types of industrial research and development 47
3.2.3 Variations in research and development activities across the
chemical industry 50
3.3 The importance of research and development 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 187

7.4.3 Balance equations 188
7.4.4 Flow in pipes 191
7.5 Heat transfer 200
7.5.1 Mechanism 200
7.5.2 Shell and tube heat exchangers 205
7.6 Separation processes 210
7.6.1 Characteristics of separation processes 210
7.6.2 Phase equilibria 211
7.6.3 Binary distillation 213
7.7 Process control 220
7.7.1 Objectives of process control 221
7.7.2 The control loop 222
7.7.3 Measuring devices 223
7.7.4 The controller 223
7.7.5 Final control element 226
7.7.6 Computer control 227
Appendix 229
References 231
Bibliography 231

8 Energy 232
Will Bland and Ted Laird
8.1 Introduction 232
8.1.1 Energy required by the chemical industry 232
8.1.2 Sources of energy 233
8.1.3 Cost of energy 235
8.1.4 Environmental factors 236
8.1.5 Properties of fuels 237
8.2 Types of energy 238
8.2.1 Variation in energy content requirement 240
8.3 Use of energy in the chemical industry 240
8.3.1 Batch reactors 240
8.3.2 Continuous reactors 241
8.3.3 Electrochemical reactors 242
8.3.4 Preparation and separation energy 242
8.3.5 Heat transfer media 243
8.4 Efficient utilization of energy 245
8.4.1 Exothermic reactions 245
8.4.2 Separation processes 246
8.4.3 Restriction of losses 247
8.5 Conclusions 248
Appendix 249
References 249
Bibliography 250

9 Environmental impact of the chemical industry 251

Andrew Hursthouse
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
 CONTENTS xi

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 289

Steve Kelham
10.1 Introduction 289
10.2 Uses of chlorine 292
10.3 Uses of caustic soda (sodium hydroxide) 292
10.4 Uses of hydrogen 292
10.5 Types of cell 294
10.5.1 Mercury cell process 294
10.5.2 Diaphragm cell process 298
10.5.3 Membrane cell process 301
10.6 Future developments 307
Bibliography 308

11 Catalysts and catalysis 309

John Pennington
11.1 Introduction 309
11.2 Definitions and constraints 310
11.2.1 Essential features 310
11.2.2 Initiators 311
11.2.3 Co-reactants 311
11.2.4 Inhibition 311
11.3 Thermodynamic relationships 312
11.3.1 Application 312
11.3.2 Effect of total pressure 313
11.3.3 Rough calculations 313
11.3.4 Thermodynamic traps 314
11.4 Homogeneous catalysis 314
11.4.1 General features 314
11.4.2 Catalyst life and poisons 315
11.4.3 Limitations 315
11.5 Heterogenization of homogeneous catalytic systems 317
11.6 Heterogeneous catalysis 319
11.6.1 Introduction 319
11.6.2 Major (primary) and minor (secondary) components 319
11.6.3 Operational modes 320
11.6.4 Chemisorption and active sites 322
11.6.5 Physical forms and their preparation 323
11.6.6 Support interactions 324
11.6.7 Catalyst structure 325
11.6.8 General kinetic behaviour 326
11.6.9 Catalyst deactivation and life 327
11.6.10 Studies on surface chemistry 328
11.6.11 Theoretical approaches 329
11. 7 Applications and mechanisms 331
11. 7.1 Introduction 331
11. 7.2 Acid catalysis 332
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 350
John Pennington
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 C 1 products 378
12.6.1 Formic (methanoic) acid and derivatives 378
12.6.2 Hydrogen cyanide 379
12.6.3 Chloromethanes 379
12.7 C 2 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 C 3 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
 CONTENTS xiii

12.9 C4 products 386

12.9.1 Butenes and butadiene 386
12.9.2 Sec-butanol (2-butanol) and methyl ethyl ketone
(2-butanone) 386
12.9.3 Tert-butanol 387
12.9.4 Maleic anhydride (cis-butanedioic anhydride) 387
12.9.5 Chloroprene (2-chlorobuta-1,3-diene) 388
12.9.6 Methacrylates (2-methylpropenoates) 388
12.9.7 Butyraldehydes (butanals) and primary butanols 388
12.9.8 C diols and related products 389
12.10 C s aliphatics 390
12.10.1 Isoprene (2-methylbuta-1,3-diene) 390
12.10.2 Plasticizer alcohols 390
12.10.3 Detergent intermediates 391
12.11 Aromatics 392
12.11.1 Hydrocarbons 392
12.11.2 Phenol 393
12.11.3 Benzyls 394
12.11.4 Nitro-compounds and amines 394
12.11.5 Phthalic (benzene-1,2-dicarboxylic) anhydride 395
12.11.6 Terephthalic (benzene-1,4-dicarboxylic) acid 395
12.12 Nylon intermediates 396
12.13 The future 398
12.13.1 The products 398
12.13.2 Future raw materials and production routes 399
References 400
Bibliography 401
Periodical special issues and supplement 402

Index 403
 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 1EE
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 Mass

=0·984 tons
1 ton = 1016 kilograms = 2240 pounds
= 1·016 tonnes

1 litre = 0·220 gallons (U.K. or Imperial) = 1 cubic metre Volume

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 Pressure

= 1·013 X 10 5 newtons per square metre
= 1·013 x 10 5 pascal

Degrees Centigrade = 0·556 (degrees Fahrenheit - 32) Temperature

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

1 therm = 100000 British thermal units Energy

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 Power

1 kilowatt = 1·34 horsepower
Nomenclature of
organic compounds

Common or trivial Systematic (or IUPAC) Structure

name name
Paraffin Alkane (a) Classes of compounds
Cycloparaffins or
Naphthenes Cycloalkanes
Olefins Alkenes
Acetylenes Alkynes
Methacrylates 2-Methylpropenoates CH 2 =C-C0 2 R
I
CH 3

Ethylene Ethene CH 2 =CH 2 (b) Individual compounds

Propylene Propene CH 3 CH=CH 2
Styrene Phen ylethene OCH=CH 2

Acetylene Ethyne H-C=C-H

Isoprene 2-Methylbuta-I,3-diene CH 2 =C-CH=CH 2
I
CH 3
Ethylene oxide Oxirane ,.0,
CH2-CH 2

Propylene oxide I-Methyloxirane ,.0,

CH 3-CH-CH 2

Methyl iodide Iodomethane CH3I

Methyl chloride Chloromethane CH 3CI
Methylene dichloride Dichloromethane CH 2Cl 2
Chloroform Trichloromethane CHCl 3
Carbon tetrachloride Tetrachloromethane CCl 4
Vinyl chloride Chloroethene CH 2 =CH-CI
Ethylene dichloride I,2-Dichloroethane CICH 2 CH 2 CI
Allyl chloride 3-Chloropropene CH 2 =CH-CH 2 -CI
Chloroprene 2-Chlorobuta-I,3-diene CH 2 =C-CH=CH 2
I
CI
Epichlorohydrin l-Chloromethyloxirane ,.o~
ClCH 2C/l- H2

Ethylene glycol Ethane-I,2-diol HOCH 2 CH 2 OH

xx NOMENCLATURE OF ORGANIC COMPOUNDS

Propargyl alcohol Prop-2-yn-I-ol H-C-C-CH 20H

Allyl alcohol Prop-2-en-I-ol CH 2=CH-CH 20H
iso-Propanol 2-Propanol CH 3CHCH 3
I
OH
Glycerol Propane-I, 2, 3-triol HOCH 2-CH-CH 20H
I
OH
sec-Butanol 2-Butanol CH 3CHCH 2CH 3
I
OH
CH 20H
I
Pentaerythritol 2,2-Di (hydroxymethyl) HOCH 2-C-CH 20H
propane-I,3-diol I
CH 20H
Lauryl alcohol Dodecanol CH3(CH2)10CH20H
Acetone Propanone CH 3COCH 3
MethyIisobutyl ketone 4-Methylpentan-2-one CH 3 COCH 2CHCH 3
I
CH 3
Formaldehyde Methanal HCHO
Acetaldehyde Ethanal CH 3 CHO
Chloral 2,2,2-Trichloroethanal Cl 3 CCHO
Propionaldehyde Propanal CH 3CH 2CHO
Acrolein Propenal CH 2=CHCHO
Bu tyraldehyde Butanal CH 3CH 2CH 2CHO
Formic acid Methanoic acid HC0 2H
Methyl formate Methyl methanoate HC0 2CH 3
Acetic acid Ethanoic acid CH 3C0 2H
Acetic anhydride Ethanoic anhydride (CH 3COhO
Peracetic acid Perethanoic acid CH 3 C0 3 H
Vinyl acetate Ethenyl ethanoate CH 2=CH0 2CCH 3
Acrylic acid Propenoic acid CH 2=CH-C0 2H
Dimethyl oxalate Dimethyl ethanedioate C0 2CH 3
I
C0 2 CH 3
Propionic acid Propanoic acid CH 3 CH 2 C0 2 H
Methyl methacrylate Methyl
2-methylpropenoate

Maleic acid cis-Butenedioic acid

H, ~
c-c
Maleic anhydride cis-Butenedioic anhydride II
c-c'
'0
H/ II
o
 NOMENCLATURE OF ORGANIC COMPOUNDS XXI

CH 2C0 2 H
I
Citric acid 2-Hydroxypropane-l, 2, 3- HO-C-C0 2 H
tricarboxylic acid I
CH 2C0 2 H
Methyl laurate Methyl dodecanoate CH3(CH2)10C02CH3
Stearic acid Octadecanoic acid CH3(CH2)16C02H
Acrylonitrile Propenonitrile CH 2 =CH-CN
Adiponitrile Hexane-I,6-dinitrile NC-(CH 2)6-CN
Urea Carbamide H 2 NCONH 2
Ketene Ethenone CH 2 =C=O

Toluene Methylbenzene
6
Aniline Phenylamine
8
C~l/CH]

6
CH

Cumene iso-Propyl benzene

Benzyl alcohol Phenylmethanol

6eH l
0H

(reH]
a-Xylene i,2-Dimethylbenzene

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

p-Xylene i,4-Dimethylbenzene
QCH]

C0 2 H
Phthalic acid Benzene-i,2-dicarboxylic H
( r e 02
acid

Isophthalic acid Benzene-i,3-dicarboxylic

acid
6
"" C02H

Terephthalic acid Benzene-I,4-dicarboxylic

acid
¢"C0 2 H
xxii NOMENCLATURE OF ORGANIC COMPOUNDS

(YCHJ
C0 2 H

o-Toluic acid 2-Methylbenzoic acid

p-Toluic acid 4-Methylbenzoic acid Q"CHl

CHO

p- Tolualdehyde 4-Methylbenzaldehyde
¢cAl

Benzidine 4,4/ -Biphenyldiamine Hl.-OO-NH~

Furfural 2-Formylfuran
CrCHO

(c) Additional compounds HFA 134a 1,1,1,2-Tetrafluoroethane CF 3CH 2 F

LTBE Ethyl t-butyl ether CH 3 CH zOqCH 3h
MTBE Methyl t-butyl ether CH 30 qCH 3)3
TAME t-Amyl methyl ether H3C-C-OCH3
/1
H3C CH 2 CH 3