The chemistry of oils and fats: sources, composition, properties and uses
Gespeichert in:
| 1. Verfasser: | |
|---|---|
| Format: | Buch |
| Sprache: | English |
| Veröffentlicht: |
Oxford [u.a.]
Blackwell Publ. [u.a.]
2004
|
| Ausgabe: | 1. publ. |
| Schlagworte: | |
| Online-Zugang: | Inhaltsverzeichnis |
| Beschreibung: | XVI, 288 S. graph. Darst. |
| ISBN: | 0849323738 1405116269 |
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| 245 | 1 | 0 | |a The chemistry of oils and fats |b sources, composition, properties and uses |c Frank D. Gunstone |
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Datensatz im Suchindex
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| adam_text | Titel: The chemistry of oils and fats
Autor: Gunstone, Frank D.
Jahr: 2004
Contents
Preface xiii
Abbreviations xv
1 Oils and fats: sources and constituents 1
1.1 Introduction 1
1.2 Specifications 1
1.3 Major oils and fats 2
1.3.1 Castor oil 3
1.3.2 Cocoa butter 3
1.3.3 Coconut oil 3
1.3.4 Corn oil 4
1.3.5 Cottonseed oil 5
1.3.6 Groundnut oil 5
1.3.7 Linseed (flaxseed, linola) 5
1.3.8 Olive oil 6
1.3.9 Palm oil 6
1.3.10 Palmkernel oil 7
1.3.11 Rapeseed oil (also called canola oil) 7
1.3.12 Rice bran oil 8
1.3.13 Safflower oil 9
1.3.14 Sesame oil 9
1.3.15 Soybean oil 9
1.3.16 Sunflower oil 11
1.3.17 Tall oil 11
1.3.18 Oils with modified fatty acid composition 12
1.4 Minor vegetable oils 12
1.4.1 Cocoa butter alternatives 13
1.4.2 Oils containing ^-linolenic acid and/or stearidonic acid 13
1.4.3 Avocado oil (Persea americana) 14
1.4.4 Chinese vegetable tallow and stillingia oil (Sapium sebifemm 14
and Stillingia sebifera)
1.4.5 Crambe (Crambe abvssinica and C. hispanica) 15
1.4.6 Cuphea 15
1.4.7 Dimorphotheca 15
1.4.8 Hemp (Marijuana, Cannabis sativa) 15
1.4.9 Gold of Pleasure (Camelina saliva, also called false flax) 16
1.4.10 Hazelnut (Corylus avellana, also called filberts) 16
1.4.11 Honesty {Lunaria annua) 16
vi CONTENTS
1.4.12 Lesquerella oils 16
1.4.13 Marigold (Calendula officinalis) 17
1.4.14 Meadowfoam (Limnanthes alba) 17
1.4.15 Sea buckthorn (Hippophae rhamnoides) 17
1.4.16 Tung oil (Aleurites fordii) 18
1.4.17 Walnut (Juglans regia) 18
1.4.18 Wheatgerm (Triticum aestivum) 18
1.5 Animal fats 18
1.5.1 Butter fat 18
1.5.2 Lard 20
1.5.3 Tallow 20
1.5.4 Fish oils 21
1.6 Major and minor components 23
1.6.1 Fatty acids, glycerol esters and waxes 23
1.6.2 Phospholipids 25
1.6.3 Sterols 26
1.6.4 Tocols 26
1.6.5 Fat soluble vitamins 29
1.6.6 Chlorophyll 30
1.6.7 Hydrocarbons 30
1.6.7.1 Alkanes 30
1.6.7.2 Squalene (C30H50) 31
1.6.7.3 Carotenes 31
1.6.7.4 Polycyclic aromatic hydrocarbons 32
1.7 Oils and fats in the market place 32
Bibliography and references 34
2 Extraction, refining and processing 36
36
38
39
39
40
40
4!
41
42
42
44
44
44
45
47
48
Bibliography and references 49
3 Structure of fatty acids and iipids 50
3.1 Introduction 50
3.2 Fatty-acid nomenclature 50
2.1 Extraction
2.2 Refining
2.2.1 Degumming
2.2.2 Neutralisation
2.2.3 Bleaching
2.2.4 Deodorisation and physical refining
2.2.5 Super-refining (chromatography)
2.3 Processing
2.3.1 Blending
2.3.2 Fractionation
2.3.2.1 Winterisation
2.3.2.2 Hydrophilisation
2.3.2.3 Urea fractionation
2.3.3 Hydrogenation
2.3.4 Interesterification with chemical catalysts
2.3.5 fnteresterification with an enzymic catalyst
CONTENTS
VII
3.3 Fatty acids — main structural features 52
3.4 Saturated acids 52
3.4.1 Short- and medium-chain acids (4:0-14:0) 53
3.4.2 Palmitic and stearic acid 53
3.4.3 Long-chain acids 54
3.5 Monoene acids 54
3.6 Methylene-interrupted polyene acids 56
3.7 Other unsaturated acids 57
3.8 Branched chain and cyclic acids 59
3.9 Oxygenated acids 61
3.9.1 Hydroxy acids 61
3.9.2 Epoxy, furanoid and oxa acids 63
3.10 Halogenated fatty acids 64
3.11 Introduction to lipid structure 64
3.12 Acylglycerols 66
3.12.1 Monoacylglycerols 66
3.12.2 Diacylglycerols 66
3.12.3 Triacylglycerols 67
3.13 Wax esters 68
3.14 Glycosyldiacylglycerols 68
3.15 Phospholipids 69
3.16 Ether lipids 72
3.17 Sphingolipids 73
Acknowledgement 75
Bibliography and references 75
4 Chemical and biological synthesis of fatty acids and lipids 76
4.1 ha try acid synthesis 76
4. . 1 Introduction 76
4. .2 Partial synthesis by chain extension 76
4. .3 Synthesis via acetylenic intermediates 77
4. .4 Synthesis by the Wittig reaction 78
4. .5 Other synthetic procedures 79
4. .6 Synthesis of isotopically labelled acids 80
4.2 Acylglycerol synthesis 81
4.2.1 Introduction 81
4.2.2 C3 synthons 81
4.2.3 Acylation procedures 81
4.2.4 Acyl migration 83
4.2.5 Protecting (blocking) groups 83
4.2.6 Synthesis of racemic acylglycerols 83
4.2.7 Synthesis of enantiomeric acylglycerols 86
4.2.8 Structured lipids 86
4.3 Phospholipid synthesis 87
4.4 Sphingolipid synthesis 88
4.5 Fatty-acid biosynthesis 88
4.5.1 Introduction 88
4.5.2 De novo synthesis of saturated acids 89
4.5.3 Desaruration to monoene and polyene acids and elongation
in plant systems 90
viii CONTENTS
4.5.4 Desaturation and elongation in animal systems 91
4.6 Lipid biosynthesis 92
4.6.1 Formation of triacylglycerols 92
4.6.2 Phospholipids 93
4.6.3 Sphingolipids 94
4.7 Isolation procedures 94
4.7.1 Crystallisation 94
4.7.2 Distillation under reduced pressure 94
4.7.3 Chromatography including silver ion systems 95
4.7.4 Urea fractionation 95
4.7.5 Enzymic enhancement 95
4.7.6 Chemical methods 96
Bibliography and references 98
5 Analytical procedures 100
5.1 Introduction 100
5.2 Classical analytical procedures 100
5.2.1 Introduction 100
5.2.2 Extraction 101
5.2.3 Melting behaviour 102
5.2.4 Unsaturation 102
5.2.5 Acidity, saponification and unsaponifiable material 103
5.2.6 Measurement of oxidative deterioration and of oxidative
stability 104
5.3 Present-day analytical techniques 106
5.3.1 Chromatography and spectroscopy 106
5.3.2 Thin-layer chromatography (TLC) and related chromatographic
systems 107
5.3.3 High performance liquid chromatography (HPLC) 108
5.3.4 Gas chromatography (GC) 108
5.3.5 NMR spectroscopy 109
5.3.6 Near-infrared and Fourier transform infrared spectroscopy 110
5.3.7 Mass spectrometry 110
5.3.8 Enzymatic procedures 112
5.4 Lipid analysis 112
5.4.1 Fatty acids 113
5.4.2 Acylglycerols 116
5.4.3 Phospholipids 122
5.4.4 Minor components (sterols and tocopherols) 122
Bibliography and references 123
6 Physical properties 124
6.1 Polymorphism, crystal structure and melting point 124
6.1.1 Alkanoic and alkenoic acids 124
6.1.2 Glycerol esters 126
6.2 Spectroscopic properties 129
6.2.1 Ultraviolet spectroscopy 129
6.2.2 Infrared spectroscopy 130
6.2.3 Electron spin resonance (ESR) spectroscopy 130
CONTENTS ix
6.2.4 H NMR spectroscopy 130
6.2.4.1 Low resolution NMR spectroscopy 131
6.2.4.2 High resolution NMR spectroscopy 131
6.2.5 I3C NMR spectroscopy 133
6.2.6 Mass spectrometry 135
6.3 Other physical properties 140
6.3.1 Density 140
6.3.2 Viscosity 140
6.3.3 Refractive index 141
6.3.4 Solubility of gases in oils 141
6.3.5 Other physical properties 141
Biblography and references 143
7 Chemical properties related to unsaturated centres 146
7.1 Hydrogenation 146
7.1.1 Catalytic hydrogenation 146
7.1.2 Other chemical reductions 148
7.1.3 Biohydrogenation 149
7.2 Oxidation through reaction with oxygen 150
7.2.1 Introduction 150
7.2.2 Autoxidation 151
7.2.3 Photo-oxidation 153
7.2.4 Hydroperoxide structures 154
7.2.4.1 Methyl oleate 155
7.2.4.2 Methyl linoleate 156
7.2.4.3 Methyl linolenate 158
7.2.4.4 Cholesterol 159
7.2.5 Decomposition of hydroperoxides to short-chain products 161
7.2.6 Other secondary reaction products 163
7.2.7 Antioxidants - introduction 164
7.2.8 Primary and secondary antioxidants 165
7.2.9 Synthetic and natural antioxidants 166
7.3 Biological oxidation 168
7.3.1 o-Oxidation 168
7.3.2 J-Oxidation 169
7.3.3 a Oxidation 169
7.3.4 Lipoxygenase 169
7.3.5 Production and function of eicosanoids 171
7.4 Other oxidation reactions 171
7.4.1 Epoxidation 171
7.4.1.1 Preparation of epoxides 173
7.4.1.2 Physical and chemical properties 174
7.4.1.3 Applications 175
7.4.2 Hydroxylation 176
7.4.3 Oxidative fission 176
7.5 Halogenation 178
7.6 Stereomutation 179
7.7 Metathesis 180
7.8 Double bond migration and cyclisation 181
X CONTENTS
7.9 Dimerisation (dimer acids, isostearic acid, estolides, Guerbet alcohols
and acids) 183
7.10 Neighbouring group participation 185
7.11 Friedel-Crafts acylation and related reactions 187
Bibliography and references 188
8 Chemical properties related to the carboxyl group 189
8.1 Introduction 189
8.2 Hydrolysis 190
8.3 Esterification 191
8.3.1 Reaction between carboxylic acids and alcohols 191
8.3.2 Acidolysis 192
8.3.3 Alcoholysis 193
8.3.4 Interesterification 195
8.3.5 Structured lipids 196
8.3.6 Lactones 198
8.4 Acid chlorides, acid anhydrides and ketene dimers 199
8.5 Peroxy acids and esters 200
8.6 Long-chain alcohols 201
8.6.1 Preparation of alcohols 201
8.6.2 Ethoxylation and propoxylation of alcohols and esters 203
8.6.3 Sulfates and other alcohol esters 204
8.6.4 Alkyl polyglycosides 205
8.6.5 Guerbet alcohols and acids 205
8.7 Acetals/ketals and orthoesters 206
8.8 Nitrogen-containing compounds 207
8.9 Sulfonation and other reactions at the a-position 209
8.10 Barton reaction 210
Bibliography and references 210
9 Nutritional properties 211
9.1 Dietary fat - sources and composition 211
9.2 Digestion, absorption and transport 214
9.3 Essential fatty acids 217
9.4 Recommendations for dietary intake 222
9.5 Cholesterol and phytosterols 224
9.6 Conjugated linoleic acid (CLA) 225
9.7 Role of fats in health and disease 226
9.7.1 Obesity 227
9.7.2 Coronary heart disease (CHD) 228
9.7.3 Diabetes 231
9.7.4 Inflammatory diseases 232
9.7.5 Psychiatric disorders 233
9.7.6 Cancer 233
9.8 Functional foods 233
9.8.1 Diacylglycerols 234
9.8.2 Phytosterols 235
Bibliography and references 236
CONTIATS xi
10 Edible uses of oils and fats 238
10.1 Spreads: butter and ghee 238
10.1.1 Butter 238
10.1.2 Ghee 240
10.2 Spreads: margarine and vanaspati 241
10.2.1 Margarine 241
10.2.2 Vanaspati 244
10.3 Baking fats, doughs and shortenings 245
10.4 Frying oils and fats 246
10.5 Salad oils, mayonnaise and salad cream and French dressings 247
10.6 Chocolate and confectionery fats 248
10.7 Ice cream 252
10.8 Incorporation of vegetable oils into dairy products 253
10.9 Edible coatings and spray processing 253
10.10 Emulsifying agents 254
Bibliography and references 255
11 Non-edible uses of oils and fats 257
11.1 Introduction 257
11.2 Basic oleochemicals 258
11.2.1 Acids 258
11.2.2 Esters 259
11.2.3 Alcohols 261
11.2.4 Fatty amines 261
11.3 Surfactants 261
11.3.1 Anionic surfactants 264
11.3.1.1 Production from carboxylic acids 264
11.3.1.2 Production from alcohols 264
11.3.2 Nonionic surfactants 265
11.3.3 Ethoxylation and propoxylation of alcohols and esters 265
11.3.4 Alkyl polyglycosides 266
11.3.5 Cationic surfactants: cyanides, amines and other nitrogen-
containing compounds 266
11.3.6 Gemini surfactants and cleavable surfactants 267
11.4 Personal care products 269
11.5 Lubricants 269
11.6 Biodiesel 271
11.7 Glycerol 274
11.8 Dibasic acids 274
11.9 Dimers. isostearic acid, estolides. Guerbet alcohols and acids 275
11.10 Oleochemicals from castor oil 276
11.11 Surface coatings and inks 277
11.12 Epoxides. hydroxy acids, polyurethanes 279
Bibliography and references 280
Index 282
|
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| publisher | Blackwell Publ. [u.a.] |
| record_format | marc |
| spelling | Gunstone, Frank D. Verfasser aut The chemistry of oils and fats sources, composition, properties and uses Frank D. Gunstone 1. publ. Oxford [u.a.] Blackwell Publ. [u.a.] 2004 XVI, 288 S. graph. Darst. txt rdacontent n rdamedia nc rdacarrier Huiles et graisses comestibles Óleos e gorduras vegetais comestíveis larpcal Oils and fats, Edible Fett (DE-588)4071189-4 gnd rswk-swf Chemie (DE-588)4009816-3 gnd rswk-swf Lipide (DE-588)4035873-2 gnd rswk-swf Öl (DE-588)4043225-7 gnd rswk-swf Lipide (DE-588)4035873-2 s DE-604 Fett (DE-588)4071189-4 s Chemie (DE-588)4009816-3 s Öl (DE-588)4043225-7 s HBZ Datenaustausch application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=013011505&sequence=000002&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis |
| spellingShingle | Gunstone, Frank D. The chemistry of oils and fats sources, composition, properties and uses Huiles et graisses comestibles Óleos e gorduras vegetais comestíveis larpcal Oils and fats, Edible Fett (DE-588)4071189-4 gnd Chemie (DE-588)4009816-3 gnd Lipide (DE-588)4035873-2 gnd Öl (DE-588)4043225-7 gnd |
| subject_GND | (DE-588)4071189-4 (DE-588)4009816-3 (DE-588)4035873-2 (DE-588)4043225-7 |
| title | The chemistry of oils and fats sources, composition, properties and uses |
| title_auth | The chemistry of oils and fats sources, composition, properties and uses |
| title_exact_search | The chemistry of oils and fats sources, composition, properties and uses |
| title_full | The chemistry of oils and fats sources, composition, properties and uses Frank D. Gunstone |
| title_fullStr | The chemistry of oils and fats sources, composition, properties and uses Frank D. Gunstone |
| title_full_unstemmed | The chemistry of oils and fats sources, composition, properties and uses Frank D. Gunstone |
| title_short | The chemistry of oils and fats |
| title_sort | the chemistry of oils and fats sources composition properties and uses |
| title_sub | sources, composition, properties and uses |
| topic | Huiles et graisses comestibles Óleos e gorduras vegetais comestíveis larpcal Oils and fats, Edible Fett (DE-588)4071189-4 gnd Chemie (DE-588)4009816-3 gnd Lipide (DE-588)4035873-2 gnd Öl (DE-588)4043225-7 gnd |
| topic_facet | Huiles et graisses comestibles Óleos e gorduras vegetais comestíveis Oils and fats, Edible Fett Chemie Lipide Öl |
| url | http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=013011505&sequence=000002&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |
| work_keys_str_mv | AT gunstonefrankd thechemistryofoilsandfatssourcescompositionpropertiesanduses |