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Fundamentals of Fragrance Chemistry



Fundamentals of Fragrance Chemistry

Charles S. Sell

ISBN: 978-3-527-81978-2 April 2019 360 Pages

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Comprehensively teaches all of the fundamentals of fragrance chemistry

Ernest Beaux, the perfumer who created Chanel No. 5, said, "One has to rely on chemists to find new aroma chemicals creating new, original notes. In perfumery, the future lies primarily in the hands of chemists." This book provides chemists and chemists-to-be with everything they need to know in order to create welcome new fragrances for the world to enjoy. It offers a simplified introduction into organic chemistry, including separation techniques and analytical methodologies; discusses the structure of perfume creation with respect to the many reactive ingredients in consumer products; and shows how to formulate effective and long-lasting scents.

Fundamentals of Fragrance Chemistry starts by covering the structure of matter in order to show how its building blocks are held together. It continues with chapters that look at hydrocarbons and heteroatoms. A description of the three states of matter and how each can be converted into another is offered next, followed by coverage of separation and purification of materials. Other chapters examine acid/base reactions; oxidation and reduction reactions; perfume structure; the mechanism of olfaction; natural and synthetic fragrance ingredients; and much more.

-Concentrates on aspects of organic chemistry, which are of particular importance to the fragrance industry
-Offers non-chemists a simplified yet complete introduction to organic chemistry?from separation techniques and analytical methodologies to the structure of perfume creation
-Provides innovative perfumers with a framework to formulate stable fragrances from the myriad of active ingredients available
-Looks at future trends in the industry and addresses concerns about sustainability and quality management

Fundamentals of Fragrance Chemistry is an ideal resource for students who are new to the subject, as well as for chemists and perfumers already working in this fragrant field of science.

Preface xi

Introduction xiii

1 The Structure of Matter 1

The Route to the Atomic Theory 1

The Atomic Theory, Atomic Number, and Atomic Weight 4

Atomic Structure 7

Isotopes 8

The Electronic Structure of Atoms 9

Electronic Structure of Transition Metals 11

Hybridisation of Orbitals 11

Chemical Bonding, Ions, Cations, Anions, and Molecules 12

Review Questions 16

2 Carbon 1 – Hydrocarbons 17

Ethane: Conformational Isomers 17

Alkanes: Structural Isomers 20

Alkenes: Geometric Isomers 22

Alkynes 26

Cyclic Structures 26

Polycyclic Structures 28

Greek Letters 30

Aromatic Rings 31

Stereoisomerism 33

Rules for Hydrocarbon Nomenclature 36

Quick Rules for Isomers 37

Stereoisomers 37

Review Questions 38

3 Carbon 2 – Heteroatoms 39

Hydrogen Bonding 39

Alcohols 40

Phenols 43

Ethers 44

Aldehydes 45

Ketones 46

Carboxylic Acids 47

Esters 49

Acid Anhydrides and Chlorides 50

Acetals and Ketals 50

Peroxy Compounds 52

Nitrogen–Amines and Ammonium Salts 53

Nitrogen–Imines, Schiff’s Bases, and Enamines 54

Nitrogen–Amides/Peptides 55

Nitrogen–Nitriles 56

Nitrogen–Nitro Compounds 57

Sulfur 58

Heterocyclic Compounds 60

Review Question 66

4 States of Matter 67

Solids 67

Liquids 71

Gases 71

Phase Changes 71

Two‐Phase Systems 73

Solubility 74

Surfactants 75

Emulsions 79

Micelles 81

Detergency 81

Bilayers 82

Colloids 84

Review Questions 84

5 Separation and Purification 85

Distillation 85

Sublimation 93

Crystallisation 93

Solvent Extraction 94

Recent Developments in Commercial Extraction of Natural Fragrance

Ingredients 95

Chromatography 96

Paper Chromatography 98

Thin Layer Chromatography 98

Column Chromatography 99

High Performance Liquid Chromatography 100

Gas Chromatography 100

Review Questions 105

6 Analysis 107

Physical Methods of Analysis 108

Density 108

Melting Point 108

Boiling Point 108

Refractive Index 109

Optical Rotation 109

Flashpoint 109

Viscosity 109

Colour 109

Chemical Methods of Analysis 110

Titration 110

Acid Content 111

Base Content 111

Peroxide Content 111

Ester Value 111

Aldehyde/Ketone Content 112

Phenol Content 112

Chemical Oxygen Demand (COD) 112

Water Content 112

Atomic Absorption 113

Spectroscopic Methods of Analysis 113

Ultraviolet (UV) 114

Infrared (IR) 118

Nuclear Magnetic Resonance (NMR) 120

Mass Spectrometry (MS) 124

Gas Chromatography–Mass Spectrometry (GC–MS) 127

Eugenol as an Example of Spectroscopic Techniques 127

Quality Control 131

Review Questions 132

7 Chemical Reactivity 133

The Three Laws of Thermodynamics 133

Free Energy 135

Chemical Reactions 136

The Principle of Microscopic Reversibility and Chemical Equilibrium 137

Reaction Profiles 138

Catalysts 140

Types of Organic Reactions 140

Review Questions 145

8 Chemistry and Perfume 1: Acid/Base Reactions 147

Acids and Bases 147

Strong and Weak 149

pH 150

Electrophiles and Nucleophiles 152

Esterification and Ester Hydrolysis 154

The Aldol Reaction and Aldol Condensation 155

Acetals and Ketals 158

Schiff’s Bases and Enamines 160

Nitriles 161

Alcohol Dehydration 162

Acid‐Catalysed Addition to Olefins 163

The Michael Reaction 164

The Grignard Reaction 165

The Friedel–Crafts Reaction 167

Electrophilic Substitutions in Aromatic Molecules 168

Review Questions 170

9 Oxidation and Reduction Reactions 171

Review Questions 185

10 Perfume Structure 187

Notes, Chords, and Discords 187

Ingredients 187

Odour Families and Top, Middle, and Base Notes 188

Persistence/Tenacity 191

Threshold 192

Impact 192

Radiance/Bloom 193

Physical and Chemical Factors 194

Review Questions 196

11 Chemistry in Consumer Goods 197

Introduction 197

Acids in Consumer Goods 198

Bases in Consumer Goods 199

Nucleophiles in Consumer Goods 200

Oxidants in Consumer Goods 201

Reductants in Consumer Goods 202

Surfactants in Consumer Goods 204

Chelating Agents in Consumer Goods 205

Photoactive Agents in Consumer Goods 206

Antibacterial Agents in Consumer Goods 207

Other Reactive Ingredients in Consumer Goods 208

Types of Consumer Goods 209

Fine Fragrance 209

Cosmetics and Toiletries 210

Personal Wash 210

Laundry 211

Household 212

Review Questions 214

12 The Chemistry of Living Organisms 215

Molecular Recognition 215

Classes of Natural Chemicals 218

Carbohydrates 218

Nucleic Acids 221

Lipids 223

Proteins 225

Toxicity and Product Safety 230

Review Questions 239

13 The Mechanism of Olfaction 243

The Role of Olfaction in Biology 243

The Organs Used in Olfaction 244

The Process of Olfaction 246

Transport to the Receptors 246

The Receptor Event 247

The Combinatorial Nature of Olfaction 249

The Perception of Odour 252

Review Questions 256

14 Natural Fragrance Ingredients 257

Why Does Nature Produce Odorous Chemicals? 257

Basic Principles of Biosynthesis: Enzymes and Cofactors 258

General Pattern of Biosynthesis of Secondary Metabolites 261

Polyketide Biosynthesis 262

Lipid Biosynthesis 263

The Shikimic Acid Pathway 265

Terpenoids 267

Degradation Products 277

Malodours 279

Review Questions 281

15 Synthetic Fragrance Ingredients 283

Why the Industry Uses Synthetic Fragrance Ingredients? 283

The Economics of Fragrance Ingredient Manufacture 284

Production of Fragrance Ingredients from Polyketides and Shikimates 288

Terpenoid Production 290

Production of Fragrance Ingredients from Petrochemicals 302

What Is Required of a Fragrance Ingredient? 320

How Novel Fragrance Ingredients Are Designed? 322

Review Questions 326

16 Chemical Information 329

How New Chemical Information Is Generated and Published? 329

Patents 329

Reviews and Books 331

Abstracts 331

How to Find Chemical Information? 333

17 Towards a Sustainable Future 335

What Is Sustainability? 335

Commercial Feasibility 337

Safety in Use 337

Natural Fragrance Ingredients 340

Synthetic Fragrance Ingredients 341

Synthetic Fragrance Ingredients A: Use of By‐Products 341

Synthetic Fragrance Ingredients B: Environmental Impact 342

Synthetic Fragrance Ingredients C: Biotechnology 344

Synthetic Fragrance Ingredients D: Finding the Balance 345

The Symrise Route 347

The Takasago Route 347

The BASF Route 348

Menthol Sustainability 349

Pro‐fragrances 351

Social and Health Factors 353

Understanding Olfaction 353

Malodour Management 354

Health and Well‐Being 355

Information 356

Conclusion 356

Answers to Review Questions 357

Glossary 371

Bibliography 379

Index 381