Alkenes and Aromatics

183 Pages·2002·25.82 MB·English

by  P.G. Taylor

CJ
RSeC
Theopen
University
ROYAL SOCIETY OF CHEMISTRY
The
Molecular
World
Alkenes and
Aromatics
This publication forms part of an Open University course, S205 The Molecular World. Most of
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First published 2002
Copyright 0 2002 The Open University
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Edited, (designed and typeset by The Open University.
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Printed 111 the United Kingdom by Bath Press Colourbooks, Glasgow.
ISBN 0 85404 680 1
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‘he titles in Tho Moleculur World series are:
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edited by Elaine Moore
edited by Peter Taylor and Michael Gagan
edited by Lesley Smart
edited by Charles Harding, David Johnson and Rob Janes
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PART 1 ADDITION - PATHWAYS
AND PRODUCTS
1.1 Introduction 11
1.2 ,4ddition of HX 13
1.3 Addition of halogens and related compounds 18
1.4 Summary of Section 1 25
2.1 syn-Additions; hydrogenation 28
2.2 Summary of Section 2 29
PART 2 AROMATIC COMPOUNDS
2.1 Summary of Sections 1 and 2 44
3.1 General principles 45
3.1. I Summary of Section 3, I 47
3.2 Nitration 48
3.3 Halogenation 50
3.4 Sulfonation 51
31.5 Friedel-Crafts reactions 53
3.5.1 Friedel-Crafts alkylation 54
3 .S .2 Friedel-Crafts acylation 58
3.6 Summary of Sections 3.2-3.5 59
4.1 Summary of Section 4 67
5.1 From coal tar to dyes 68
5.2 Coupling reactions of diazonium salts 72
5.3 Substitution reactions of diazonium salts 73
5.4 Summary of Section 5 74
P.ART 3 A FIRST LOOK AT SYNTHESIS
1.1 Neurotransmitters and receptors 93
2.1 Summary of Sections 1 and 2 100
4.1 General issues 102
4.2 Some golden rules 103
4.3 The next stage 105
4.4 Where will it all end? 108
4.5 Summary of Sections 3 and 4 110
S.1 Preparation of 2-1-phenyl-1-propene 111
5.2 How much do we have? 113
5.3 Preparation of the bromoalcohol 114
5.4 Making the oxirane and pseudoephedrine 117
5.5 How efficient was the synthesis? 120
5.6 Summary of Section 5 121
7.1 ‘Green chemistry’ 124
7.2 ‘Green chemistry’ in action 126
7.3 Summary of Sections 6 and 7 129
CASE STUDY: INDUSTRIAL ORGANIC CHEMISTRY
1.1 The chemical industry 139
1.2 Large- and small-scale production 143
1.3 Sub-division of the organic chemicals industry 143
.2.1 Theoretical considerations 144
2.2 Characteristics of the petrochemical sector 146
2.3 Energy considerations 147
2.4 Chemical considerations 147
2.4.1 Cracking 150
2.4.2 Reforming 151
2.4.3 Building blocks 151
2.4.4 Ethylene (ethene) 152
2.4.5 Propylene (propene) 152
2.4.6 Buta- 1,3-diene 152
2.4.7 Benzene 156
2.4.8 Toluene (methylbenzene) 157
2.4.9 Xylenes (dimethylbenzenes) 159
2.5 Environmental concerns 160
2.6 Location of plants 161
31.1 Some typical fine chemicals 162
3.1 . 1 FusiladeTM 162
3.1.2 Penicillins 164
3.1.3 Procion dyes 165
3.1.4 Kevlar 166
3.2 Characteristics of the speciality and fine chemicals sector 167
3.3 Chemical considerations 169
3.4 Location of plants 169