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Engineering Perfumes

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Engineering Perfumes ENGINEERING PERFUMES Dissertation presented to the FACULDADE DE ENGENHARIA DA UNIVERSIDADE DO PORTO for the degree of Doctor in Chemical Engineering by Paula Cristina Baldaia M. S. Gomes Supervisors Professor Alírio E. Rodriges Doutora Vera G. Mata Departamento de Engenharia Química Faculdade de Engenharia Universidade do Porto May 2005 i TABLE OF CONTENTS LIST OF FIGURES viii LIST OF TABLES xv CHAPTER 1 INTRODUCTION 1 1.1 Relevance and Motivation 1 1.2 Objectives and Outline 3 CHAPTER 2 PERFUMERY œ A REVIEW 5 2.1 The F&F Industry 6 2.2 The regulatory context 14 2.3 The sense of smell 15 2.4 Classification of perfumery materials 17 2.4.1 The chemistry of flavour and fragrance materials 18 2.4.2 Aroma chemicals 18 2.4.3 Natural materials 21 2.5 Production of aromatic plants in Portugal 25 2.6 Production methods of natural perfumery materials 27 2.6.1 Distillation 28 2.6.2 Expression 30 2.6.3 Solvent Extraction 31 ii 2.6.4 Supercritical Fluid Extraction 33 2.7 Adding value to naturals 34 2.8 Formulation and production of perfumes 35 2.8.1 Perfume structure and evaporation 37 2.8.2 Classification of perfumes 40 2.8.3 Creation of perfume 42 2.8.4 Manufacturing of perfumes 44 2.9 The scientific contribution to perfumery 46 2.9.1 Isolation methods 46 2.9.2 Analytical methods 47 2.9.3 Physical basis 49 2.10 Conclusions 52 2.11 References 53 CHAPTER 3 CHARACTERIZATION OF TWO PORTUGUESE NATURAL 5 MATERIALS 6 3.1 Introduction 57 3.2 Portuguese-grown Geranium-rose (Pelargonium sp) essential 59 oil 3.2.1 Organoleptic characteristics 61 3.2.2 Perfumery and cosmetic applications 62 3.2.3 Review on geranium characterization 63 3.2.4 Materials and methods 64 3.2.5 Results and discussion 67 iii 3.2.6 Conclusions 76 3.3 Cistus (Cistus ladanifer) essential oil growing wild in Portugal 76 3.3.1 Organoleptic characteristics 78 3.3.2 Perfumery and cosmetic applications 78 3.3.3 Review on rockrose 79 3.3.4 Materials and methods 83 3.3.5 Results and discussion 84 3.3.6 Conclusions 90 3.4 References 90 CHAPTER 4 PRODUCTION OF ROSE GERANIUM OIL USING 93 SUPERCRITICAL FLUID EXTRACTION 4.1 Introduction 94 4.1.1 Fundamentals of supercritical technology 94 4.1.2 Description of plant material and its processing before extraction 100 4.1.3 The supercritical extraction process 101 4.1.4 Description of separation methods 103 4.2 Design and construction of a SFE equipment 104 4.2.1 Description of SCRITICAL equipment 106 4.3 Materials and methods 110 4.3.1 Plant material 110 4.3.2 Methods 111 4.4 Results 114 iv 4.4.1 Comparison of SFE extract with products obtained using traditional 114 techniques 4.4.2 Effect of operating parameters 117 4.4.3 Organoleptic description 130 2.5 Conclusions 131 4.6 References 132 CHAPTER 5 REFINING OF NATURAL MATERIALS USING PREPARATIVE LIQUID CHROMATOGRAPHY 135 5.1 Introduction 136 5.1.1 Deterpenation using adsorption 138 5.2 Preparative chromatography 139 5.3 Description of the preparative chromatography model 142 5.3.1 Model equations 142 5.3.2 Definition of operation modes 144 5.3.3 Numerical solution 145 5.3.4 Performance criteria 146 5.4 Case study: Fractionation of lemon oil 147 5.5 Experimental 148 5.5.1 Materials 148 5.5.2 Packing material 149 5.5.3 Description of equipment 149 5.5.4 Operating conditions 150 5.5.5 Samples 151 5.6 Results 151 v 5.6.1 Determination of the isotherm parameters 151 5.6.2 Optimisation of the separation of limonene/citral by simulation 154 5.7 Conclusion 160 5.8 References 160 CHAPTER 6 PERFUME DESIGN WITH SCIENTIFIC BASIS 163 6.1 Introduction: odour value concept 164 6.1.1 Objectives of this work 167 6.2 Case study: simple binary perfume mixture 167 6.2.1 Effect of the solvent on the OV 170 6.2.2 Effect of adding another fragrant note on the OV 173 6.3 Ternary perfume mixtures 175 6.3.1 Perfumery ternary diagram (PTD) concept 176 6.3.2 Perfume test case 177 6.3.3 Effect of the liquid non-ideality on the PTD 179 6.3.4 Effect of ethanol on the PTD 181 6.4 New case studies 183 6.5 Design of a perfume: how to choose the initial mixture? 190 6.6 Conclusions 191 6.7 References 192 CHAPTER 7 EXPERIMENTAL VALIDATION OF PERFUMERY TERNARY 193 DIAGRAM METHODOLOGY 7.1 Introduction 194 7.1.1 Odour threshold concentration 195 vi 7.1.2 Headspace concentration 198 7.2 Experimental 198 7.2.1 Measurement of odour threshold values 198 7.2.2 Headspace analysis 203 7.3 Results 207 7.3.1 Determination of odour threshold values 207 7.3.2 Comparison of headspace analysis methods 209 7.3.3 Binary perfume mixtures 212 7.3.4 Perfumery Ternary Diagrams as a predictive tool 221 7.3.5 Validation of PTD methodology 222 7.4 Conclusions 227 7.5 References 229 CHAPTER 8 CARACTERISATION OF ODOUR PERFORMANCE USING A 230 PERFUME DIFFUSION MODEL 8.1 Introduction 231 8.2 Description of diffusion model 233 8.2.1 Gas phase 233 8.2.2 Liquid phase 234 8.2.3 Boundary and initial conditions 235 8.2.4 Numerical solution 235 8.3 Case study 236 8.3.1 Caracterisation of the case study system 236 8.3.2 Effect of the top note 237 vii 8.3.3 Effect of middle and base notes 241 8.3.4 Evaporation over distance 245 8.3.5 Study of odour performance criteria 247 8.4 Conclusions 250 8.5 References 251 CHAPTER 9 CONCLUSIONS AND FUTURE WORK 252 9.1 Conclusions 252 9.2 Future work 255 APPENDIX A CALCULATION OF THE ACTIVITY COEFFICIENTS USING THE 257 UNIFAC METHOD APPENDIX B CALCULATION OF THE DIFFUSION COEFFICIENTS USING 262 THE FULLER ET AL. METHOD APPENDIX C CALCULATION OF ODOUR THRESHOLD VALUES 264 viii LIST OF FIGURES CHAPTER 2 Figure 2.1 Worldwide geographical distribution of top 10 F&F companies. 6 Figure 2.2 Market share of Flavour & Fragrance Industries in 2003 (source: Leffingwell & 7 Associates, in Leffingwell, 2004). Figure 2.3 The worldwide market of F&Fin 2002 (source: Freedonia Group and C&EN 7 estimates, in Short, 2002). Figure 2.4 Market of F&F industry by category of product in 2002 (source: Freedonia Group 8 and C&EN estimate, in Short, 2002). Figure 2.5 Sales volume of F&F products by application: (a) Fragrances; (b) Flavours (source: 9 Leffingwell & Associates and IAL consultants in Rouhi, 2003a). Figure 2.6 Production of naturals in poor countries: (a) harvest of jasmine flowers by handpick; 11 (b) distillation using rudimentary equipment. Figure 2.7 Cultivation fields of lavender and distillation unit, in Grasse, France (source: a- 12 Newman, 1998; b-Pybus and Sell, 1999). Figure 2.8 Volume of Imports and Exports in Portugal, for 1995 and 2002: (a) Essential oils, 13 Resinoids, Cosmetics and Perfumery products; (b) Perfumes and Eau de Toilettes (source: INEl, 2002). Figure 2.9 The olfaction mechanism (Nobel-prize.org, 2004). 16 Figure 2.10 Some examples of chemical structures of flavour & fragrance materials. 19 Figure 2.11 Capturing new scents by portable headspace analysis (source: Newman, 1998). 20 (Newman, 1998). Figure 2.12 Distribution of fields used for growing aromatic plants (source: INE, 1999). 26 Figure 2.13 Estimative of production per hectare for some aromatic plants with viability of being 27 cultivated in Portugal (source: INETI, 1982). Figure 2.14 Industrial methods used to produce natural materials. 28 Figure 2.15 Distillation process for producing essential oils. 29 Figure 2.16 Expression process to produce citrus essential oils. 31 Figure 2.17 Process of extraction with organic solvents to produce natural extracts (source: 32 Newman, 1998). Figure 2.18 Industrial plant for supercritical fluid extraction (Flavex,Germany). 34 Figure 2.19 Triangular structure of a perfume and relation between top, middle and base notes 39 for a perfume formulation used in the concentration of 12% to 18% in alcohol (Calkin and Jellinek, 1994). Figure 2.20 Odour profile during evaporation of a perfume with a triangular structure. 39 Figure 2.21 Classification of fragrances according to Poucher (1955). 42 ix Figure 2.22 Polarity of different kinds of fragrant compounds and the relation with other 51 physical properties (Calkin and Jellinek, 1994). CHAPTER 3 Figure 3.1 Aromatic garden in Fundação de Serralves, Porto (Portugal). 57 Figure 3.2 Aromatic garden created within this work, Vila da Feira (Portugal). 57 Figure 3.3 Pilot planting of geranium, Oliveira do Douro e Miramar (Portugal). 57 Figure 3.4 Rose-geranium plant (Pelargonium graveolens) and the trichomes that contain the 58 essential oil. Figure 3.5 Worldwide production and imports of geranium oil (source: Dermarne, 2002). 59 Figure 3.6 Composition of two perfumes with geranium note: (a) men‘s fragrance, Hugo, Hugo 61 Boss(1995); (b) women‘s fragrance, Paris, YSL (1983). Figure 3.7 Leaves of rose geranium fresh plant : (a) green;(b) yellow. 63 Figure 3.8 Equipment used for isolating the essential oil: (a) Clevenger apparatus;(b) Collection 64 of essential oil; (c) rotary evaporator under reduced pressure. Figure 3.9 Gas chromatography equipment Varian CP-3800, with FID (Varian) and MS 65 (Saturn2000) detectors. Figure 3.10 GC/MS chromatogram of Portuguese-grown geranium oil obtained from fresh green 67 foliage of Pelargonium sp.
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