Contents

Contributors ........................................................................ v

Preface ............................................................................... xi

Volume 1. Edible Oil and Fat Products: Chemistry,

Properties, and Health Effects
1.1 Chemistry of Fatty Acids ...................................................... 1:1
1.1.1 Introduction ..................................................... 1:1
1.1.2 Composition and Structure .............................. 1:2
1.1.3 Hydrolysis, Esterification, and Ester
Exchange ........................................................ 1:10
1.1.4 Oxidation ......................................................... 1:15
1.1.5 Reduction ........................................................ 1:25
1.1.6 Production of Surface Active Compounds
and Oleochemicals .......................................... 1:27
1.1.7 Modifying Fatty Acid Structure ......................... 1:32
1.1.8 Novel Chemistry for Functionalizing the Alkyl
Chain ............................................................... 1:36
References .................................................................... 1:39
1.2 Crystallization of Fats and Oils ............................................ 1:45
1.2.1 Introduction ..................................................... 1:45
1.2.2 Lipid Phase Behavior ....................................... 1:46
1.2.3 Crystallization Behavior ................................... 1:57
1.2.4 Controlling Crystallization ................................ 1:68
1.2.5 Summary ......................................................... 1:73
References .................................................................... 1:73

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1.3 Polymorphism in Fats and Oils ............................................ 1:77

1.3.1 Introduction ..................................................... 1:77
1.3.2 Basic Concepts of Polymorphism of Fats ........ 1:78
1.3.3 Polymorphism of Monoacid Triacylglycerols .... 1:85
1.3.4 Polymorphism of Mixed-acid
Triacylglycerols ................................................ 1:90
1.3.5 Fat Mixtures and Polymorphism ...................... 1:100
1.3.6 Polymorphism of Natural Fats ......................... 1:108
1.3.7 Summary ......................................................... 1:115
References .................................................................... 1:116
1.4 Fat Crystal Networks ............................................................ 1:121
1.4.1 Introduction ..................................................... 1:121
1.4.2 Mechanical Properties of Milkfat ...................... 1:122
1.4.3 Lipid Composition ............................................ 1:123
1.4.4 Processing Conditions ..................................... 1:125
1.4.5 Nucleation and Crystal Growth ........................ 1:126
1.4.6 Mechanical Properties ..................................... 1:148
1.4.7 Assessing the Validity of the Model:
Correlating Experimentally Determined
Parameters ...................................................... 1:154
Acknowledgments .......................................................... 1:158
References .................................................................... 1:158
1.5 Animal Fats ........................................................................... 1:161
1.5.1 Introduction ..................................................... 1:161
1.5.2 Sources, Fatty Acid Content, and
Acylglycerol Structure ...................................... 1:162
1.5.3 Acylglycerol Structure and Its Relationship to
Functionality and Use ...................................... 1:168
1.5.4 Quality Indicators for Edible Fats ..................... 1:171
1.5.5 Regulatory and Commercial Classifications
of Animal Fats ................................................. 1:174

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1.5.6 Patterns and Trends in the Production and

Use of Animal Fats .......................................... 1:179
1.5.7 Processing of Animal Fats ............................... 1:182
1.5.8 Antioxidants in Animal Fats ............................. 1:194
1.5.9 Characteristics of Animal Fat-based
Shortenings and Frying Fats ............................ 1:195
1.5.10 Recent Developments ..................................... 1:197
Acknowledgments .......................................................... 1:205
References .................................................................... 1:205
1.6 Vegetable Oils ...................................................................... 1:213
1.6.1 Introduction ..................................................... 1:213
1.6.2 Biosynthesis .................................................... 1:213
1.6.3 Minor Components .......................................... 1:217
1.6.4 Classification of Vegetable Oils ....................... 1:219
1.6.5 The Major Vegetable Oils and Fats ................. 1:224
1.6.6 Speciality and Minor Oils ................................. 1:232
1.6.7 Modification of Oils and Fats ........................... 1:242
1.6.8 Technological Procedures Used for Lipid
Modification ..................................................... 1:244
1.6.9 Biological Methods of Lipid Modification .......... 1:251
1.6.10 Production and Trade Statistics ....................... 1:258
1.6.11 Conclusion ....................................................... 1:259
References .................................................................... 1:259
1.7 Lipid Oxidation: Theoretical Aspects ................................... 1:269
1.7.1 Introduction ..................................................... 1:269
1.7.2 Initiation (LH L ) ........................................ 1:273
1.7.3 Propagation ..................................................... 1:304
1.7.4 Termination ..................................................... 1:333
1.7.5 Expanded Integrated Reaction Scheme .......... 1:341
References .................................................................... 1:343

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1.8 Lipid Oxidation: Measurement Methods .............................. 1:357

1.8.1 Introduction ..................................................... 1:357
1.8.2 Methods for Measuring Lipid Oxidation ............ 1:358
1.8.3 Measurement of Oxygen Absorption ................ 1:359
1.8.4 Measurement of Reactant Change .................. 1:360
1.8.5 Measurement of Primary Products of
Oxidation ......................................................... 1:361
1.8.6 Measurement of Secondary Products of
Oxidation ......................................................... 1:366
1.8.7 Measurement of Free Radicals ........................ 1:373
1.8.8 Other Methods ................................................. 1:374
1.8.9 Measurement of Frying Fat Deterioration ........ 1:377
1.8.10 Methods for Measuring Antioxidant Activity ..... 1:378
1.8.11 Conclusions and Recommendations ................ 1:380
References .................................................................... 1:380
1.9 Flavor Components of Fats and Oils ................................... 1:387
1.9.1 Free Radical Autoxidation of Lipids ................. 1:387
1.9.2 Hydroperoxides of Fatty Acids or Their
Esters .............................................................. 1:388
1.9.3 Major Volatile Compounds of Commercial
Fats and Oils ................................................... 1:395
References .................................................................... 1:408
1.10 Flavor and Sensory Aspects ................................................ 1:413
1.10.1 Introduction ..................................................... 1:413
1.10.2 Sensory Methods ............................................. 1:413
1.10.3 Factors Affecting Sensory Measurements ....... 1:415
1.10.4 Experimental Design and Statistical
Analysis ........................................................... 1:416
1.10.5 Sensory Testing Facility .................................. 1:416
1.10.6 Sample Preparation and Presentation ............. 1:418
1.10.7 Reference Samples ......................................... 1:420

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 Contents xvii

1.10.8 Selection and Training of Panelists .................. 1:422

1.10.9 Monitoring and Motivation of Panelists ............ 1:423
1.10.10 Sensory Evaluation of Oils ............................... 1:423
1.10.11 Sensory Evaluation of Oil-containing Foods .... 1:426
1.10.12 Sensory Evaluation of Frying Oils/Room
Odor ................................................................ 1:426
1.10.13 Sensory Evaluation of Fried Foods .................. 1:426
1.10.14 Electronic Nose ............................................... 1:427
1.10.15 Gas Chromatography-olfactometery ................ 1:427
1.10.16 Conclusions ..................................................... 1:427
References .................................................................... 1:428
1.11 Antioxidants: Science, Technology, and Applications ......... 1:431
1.11.1 An Antioxidant Definition ............................... 1:431
1.11.2 History of Antioxidants and Their Use .............. 1:432
1.11.3 Scope of Using Antioxidants in Food ............... 1:433
1.11.4 Oxidation of Fats and Oils and Mechanism of
Antioxidants ..................................................... 1:434
1.11.5 Classification of Antioxidants ........................... 1:436
1.11.6 Evaluation of Antioxidant Activity ..................... 1:445
1.11.7 Commonly Used Antioxidants in Foods ........... 1:455
1.11.8 Estimation and Analysis of Antioxidants in
Foods .............................................................. 1:474
1.11.9 Technological Considerations in Using
Antioxidants ..................................................... 1:474
1.11.10 Regulatory Status and Safety Issues of
Synthetic and Natural Antioxidants .................. 1:475
1.11.11 Safety Considerations of Antioxidants Used
in Foods .......................................................... 1:476
References .................................................................... 1:483
1.12 Antioxidants: Regulatory Status ........................................... 1:491
1.12.1 Introduction ..................................................... 1:491
1.12.2 Synthetic Antioxidants ..................................... 1:492

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1.12.3 Natural Antioxidants ........................................ 1:503

1.12.4 Conclusions ..................................................... 1:508
References .................................................................... 1:509
1.13 Toxicity and Safety of Fats and Oils .................................... 1:513
1.13.1 Introduction ..................................................... 1:513
1.13.2 Adverse Effects of Fats and Associated
Constituents .................................................... 1:515
1.13.3 Adverse Effects of Some Natural
Constituents in Fats and Oils ........................... 1:530
1.13.4 Bioactive Lipid-soluble Constituents ................ 1:533
1.13.5 Chemical Reactions in Fats ............................. 1:535
1.13.6 Adverse Products from Overheated Fats and
Oils .................................................................. 1:543
1.13.7 Toxic Substances Produced during Smoking,
Charbroiling, and Barbecuing of Foods ............ 1:545
1.13.8 Potential Hazards from Government
Approved Antioxidants ..................................... 1:547
1.13.9 Manufacturing Hazards in Processing Crude
Oils and Fats ................................................... 1:550
1.13.10 Conclusions ..................................................... 1:552
References .................................................................... 1:552
1.14 Quality Assurance of Fats and Oils ..................................... 1:565
1.14.1 Introduction ..................................................... 1:565
1.14.2 Oil Composition ............................................... 1:568
1.14.3 Minor Components .......................................... 1:570
1.14.4 Unsaponfiables Matter ..................................... 1:570
1.14.5 Characteristics of Fats and Oils ....................... 1:571
1.14.6 Color and Appearance ..................................... 1:571
1.14.7 Oxidative Quality and Stability Tests ............... 1:572
1.14.8 Carbonyl Compounds ...................................... 1:573
1.14.9 Polymers and Polar Components .................... 1:573
1.14.10 Antioxidants ..................................................... 1:574

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 Contents xix

1.14.11 Adulteration ..................................................... 1:574

1.14.12 Pollutants ........................................................ 1:574
References .................................................................... 1:574
1.15 Dietary Lipids and Health ..................................................... 1:577
1.15.1 Introduction ..................................................... 1:577
1.15.2 PUFA Biochemistry ......................................... 1:582
1.15.3 Molecular Actions ............................................ 1:583
1.15.4 Fat and Chronic Diseases ............................... 1:586
1.15.5 Role of Dietary Fat in Cardiovascular
Disease and Atherosclerosis ........................... 1:589
References .................................................................... 1:600

Volume 2. Edible Oil and Fat Products: Edible Oils

2.1 Butter .................................................................................... 2:1
2.1.1 Introduction ..................................................... 2:1
2.1.2 Chemical Composition ..................................... 2:2
2.1.3 Modification of Milkfat ...................................... 2:12
2.1.4 Quality Control ................................................. 2:21
2.1.5 Butter Manufacture .......................................... 2:26
2.1.6 Butter Fat Products .......................................... 2:45
2.1.7 Economics ....................................................... 2:52
References .................................................................... 2:55
2.2 Canola Oil ............................................................................. 2:61
2.2.1 Introduction ..................................................... 2:61
2.2.2 Origin ............................................................... 2:62
2.2.3 Development of Canola ................................... 2:62
2.2.4 Composition .................................................... 2:63
2.2.5 Physical Properties .......................................... 2:74
2.2.6 Canola Oil Extraction and Processing .............. 2:76
2.2.7 Nutritional Properties of Canola Oil .................. 2:93
2.2.8 Major Food Uses ............................................. 2:99

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2.2.9 Nonfood Uses of Standard Canola Oil ............. 2:109

2.2.10 Production of Oilseeds and Oils ....................... 2:113
References .................................................................... 2:116
2.3 Coconut Oil ........................................................................... 2:123
2.3.1 The Coconut Palm ........................................... 2:123
2.3.2 The Fruit .......................................................... 2:126
2.3.3 Copra .............................................................. 2:128
2.3.4 Oil Extraction ................................................... 2:129
2.3.5 Refining ........................................................... 2:132
2.3.6 Coconut Oil Composition ................................. 2:135
2.3.7 Chemical and Physical Tests ........................... 2:137
2.3.8 Uses ................................................................ 2:141
2.3.9 Storage ............................................................ 2:142
2.3.10 Economics ....................................................... 2:143
References .................................................................... 2:146
2.4 Corn Oil ................................................................................ 2:149
2.4.1 Overview ......................................................... 2:149
2.4.2 Extraction and Refining ................................... 2:151
2.4.3 Composition .................................................... 2:155
2.4.4 Properties of Corn Oil ...................................... 2:165
2.4.5 Major Food Uses of Corn Oil ........................... 2:167
2.4.6 Nonfood Uses of Corn Oil ................................ 2:168
2.4.7 Conclusions ..................................................... 2:168
References .................................................................... 2:169
2.5 Cottonseed Oil ...................................................................... 2:173
2.5.1 Introduction ..................................................... 2:173
2.5.2 Cottonseed Oil Industry Development ............. 2:174
2.5.3 Cottonseed Oil Properties ................................ 2:185
2.5.4 Cottonseed Handling, Oil Extraction and
Processing ....................................................... 2:207

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2.5.5 Regulatory Considerations: Cottonseed Oil

Extraction and Processing ............................... 2:235
2.5.6 Cottonseed Oil Products Finishing
Treatment ........................................................ 2:242
2.5.7 Cottonseed Oil Utilization ................................ 2:246
2.5.8 Liquid Oils ....................................................... 2:248
2.5.9 Shortenings ..................................................... 2:256
2.5.10 Margarine and Spreads ................................... 2:267
2.5.11 Other Cottonseed Oil Uses .............................. 2:272
References .................................................................... 2:272
2.6 Flax Oil and High Linolenic Oils ........................................... 2:281
2.6.1 Introduction ..................................................... 2:281
2.6.2 Flax ................................................................. 2:282
2.6.3 Perilla Oil ......................................................... 2:292
2.6.4 Camelina ......................................................... 2:294
2.6.5 Chia ................................................................. 2:298
References .................................................................... 2:298
2.7 Olive Oil ................................................................................ 2:303
2.7.1 Introduction and History ................................... 2:303
2.7.2 Statistics and Definitions ................................. 2:306
2.7.3 Extraction Technology ..................................... 2:310
2.7.4 Refining of Olive Oils ....................................... 2:314
2.7.5 Refining of Pomace Oil .................................... 2:316
2.7.6 Olive Oil Components ...................................... 2:317
2.7.7 Analysis of Olive Oils ....................................... 2:320
References .................................................................... 2:328
2.8 Palm Oil ................................................................................ 2:333
2.8.1 Introduction ..................................................... 2:333
2.8.2 Chemical and Physical Properties of Palm
Oil .................................................................... 2:339
2.8.3 Production Process ......................................... 2:351

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2.8.4 Refining and Fractionation ............................... 2:371

2.8.5 End Uses ......................................................... 2:388
2.8.6 Potential Developments ................................... 2:410
2.8.7 Nutritional Effects of Palm Oil .......................... 2:411
2.8.8 Prospects of Palm Oil and Market
Requirements .................................................. 2:417
References .................................................................... 2:423
2.9 Peanut Oil ............................................................................. 2:431
2.9.1 Peanut Origin and History ................................ 2:431
2.9.2 Global .............................................................. 2:432
2.9.3 Environmental and Genotype Effects on the
Composition Peanuts ...................................... 2:445
2.9.4 Modification of Oil Characteristics through
Breeding .......................................................... 2:445
2.9.5 Oil Color .......................................................... 2:446
2.9.6 Peanut Oil Evaluation and Composition ........... 2:447
2.9.7 Uses ................................................................ 2:453
2.9.8 Dietary Aspects ............................................... 2:454
2.9.9 Allergenicity ..................................................... 2:455
References .................................................................... 2:455
2.10 Rice Bran Oil ........................................................................ 2:465
2.10.1 Introduction ..................................................... 2:465
2.10.2 Composition of Rice and Rice Bran Lipids ....... 2:466
2.10.3 Milling of Rice .................................................. 2:470
2.10.4 Enzymes in Rice Bran ..................................... 2:473
2.10.5 Stabilization of Rice Bran ................................ 2:475
2.10.6 Rice Bran to Rice Bran Oil ............................... 2:477
2.10.7 Refining of the Oil ............................................ 2:478
2.10.8 Dewaxing ........................................................ 2:479
2.10.9 Degumming and Deacidification ...................... 2:479

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2.10.10 Bleaching, Hydrogenation and

Deodorerization ............................................... 2:480
2.10.11 Winterization .................................................... 2:481
2.10.12 Co-products from Processing .......................... 2:481
2.10.13 Composition of Refined Rice Bran Oil .............. 2:482
2.10.14 Rice Bran Oil Nutrition ..................................... 2:483
2.10.15 Rice Bran Oil Utilization ................................... 2:485
2.10.16 Rice Oil Production (Potential) ......................... 2:486
2.10.17 Summary ......................................................... 2:487
References .................................................................... 2:487
2.11 Safflower Oil ......................................................................... 2:491
2.11.1 History and Botanical Description .................... 2:491
2.11.2 Physical and Chemical Properties ................... 2:505
2.11.3 Processing ....................................................... 2:511
2.11.4 Economics and Marketing ............................... 2:514
2.11.5 Quality Assessment ......................................... 2:522
2.11.6 Storage and Transportation ............................. 2:525
2.11.7 Unique Uses .................................................... 2:527
References .................................................................... 2:530
2.12 Sesame Oil ........................................................................... 2:537
2.12.1 Introduction ..................................................... 2:537
2.12.2 Botany of Sesame ........................................... 2:538
2.12.3 World Production ............................................. 2:541
2.12.4 Chemical Composition ..................................... 2:544
2.12.5 Sesame Lignans and Lignan Glycosides ......... 2:549
2.12.6 Processing ....................................................... 2:555
2.12.7 Nutritional Characteristics ................................ 2:564
Reference ...................................................................... 2:570
2.13 Soybean Oil .......................................................................... 2:577
2.13.1 Introduction ..................................................... 2:577
2.13.2 Composition of Soybeans ................................ 2:578

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2.13.3 Physical Properties of Soybean Oil .................. 2:584

2.13.4 Grading ........................................................... 2:589
2.13.5 Recovery of Oil from Soybeans ....................... 2:591
2.13.6 Qualities of Soybean Oils and Meals
Extracted by Different Methods ........................ 2:600
2.13.7 Soy Protein Ingredients ................................... 2:603
2.13.8 Basic Processing Operations ........................... 2:604
2.13.9 Alternative Refining Methods ........................... 2:611
2.13.10 Coproducts and Utilization ............................... 2:612
2.13.11 Food and Biobased Product Uses of
Soybean Oil ..................................................... 2:614
2.13.12 Oxidative Quality of Soybean Oil ..................... 2:629
2.13.13 Dietary Fatty Acids and Their Health Effects ... 2:638
References .................................................................... 2:641
2.14 Sunflower Oil ........................................................................ 2:655
2.14.1 Historical Review ............................................. 2:655
2.14.2 Sunflower Crops .............................................. 2:658
2.14.3 Chemical and Physical Properties of Regular
Sunflower Oil ................................................... 2:664
2.14.4 Sunflower Seed of Modified Fatty Acid
Composition .................................................... 2:674
2.14.5 Extraction and Processing of Sunflower Oil ..... 2:685
2.14.6 Hydrogenation of Regular Sunflower Oil .......... 2:700
2.14.7 Storage and Deterioration of Sunflower Oil ...... 2:703
2.14.8 Uses of Sunflower Oil ...................................... 2:707
2.14.9 World Production and Distribution of
Sunflower Oil ................................................... 2:713
2.14.10 Sunflower Oil Extraction and Processing
by-products ...................................................... 2:719
References .................................................................... 2:725

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Volume 3. Edible Oil and Fat Products: Specialty

Oils and Oil Products
3.1 Conjugated Linoleic Acid Oils .............................................. 3:1
3.1.1 Introduction ..................................................... 3:1
3.1.2 Metabolism ...................................................... 3:2
3.1.3 Physiological Actions of CLA ........................... 3:3
3.1.4 Strategies to Increase Dietary Intake of CLA ... 3:8
3.1.5 Commercial Production of CLA ........................ 3:8
3.1.6 Analysis of Conjugated Linoleic Acids ............. 3:21
3.1.7 Conclusions ..................................................... 3:29
References .................................................................... 3:29
3.2 Diacylglycerols ..................................................................... 3:37
3.2.1 Introduction ..................................................... 3:37
3.2.2 Comparison of DAG Oil vs. TAG Oil ................ 3:39
3.2.3 Summary ......................................................... 3:44
References .................................................................... 3:46
3.3 Citrus Oils and Essences ..................................................... 3:49
3.3.1 Introduction ..................................................... 3:49
3.3.2 Oil Extraction ................................................... 3:50
3.3.3 Chemical Composition ..................................... 3:52
3.3.4 Storage of Citrus Oils ...................................... 3:58
3.3.5 Applications of Citrus Oils and Essences ......... 3:61
3.3.6 Challenges ...................................................... 3:62
3.3.7 Conclusions ..................................................... 3:63
References .................................................................... 3:63
3.4 Gamma Linolenic Acid Oils .................................................. 3:67
3.4.1 Introduction ..................................................... 3:67
3.4.2 Sources of GLA ............................................... 3:68
3.4.3 Extraction of Oil ............................................... 3:76
3.4.4 Metabolism of GLA .......................................... 3:80
3.4.5 Cardiovascular Effects ..................................... 3:83

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3.4.6 Cancer ............................................................. 3:87

3.4.7 Immune Function and Autoimmune
Diseases ......................................................... 3:93
3.4.8 Skin Conditions ............................................... 3:99
3.4.9 Diabetes .......................................................... 3:103
3.4.10 Premenstrual Syndrome (PMS) ....................... 3:106
3.4.11 Infant Nutrition and Development .................... 3:107
3.4.12 Drug/Nutrient Interactions ................................ 3:108
3.4.13 Safety of GLA-containing Oils .......................... 3:109
3.4.14 Current Research Focus .................................. 3:110
References .................................................................... 3:111
3.5 Oils from Microorganisms .................................................... 3:121
3.5.1 General Introduction and Background
Information ...................................................... 3:121
3.5.2 Commercial Microbial Oils ............................... 3:130
3.5.3 SCOs in Current (2003) Production ................. 3:137
3.5.4 Prospects for Production of Other PUFAs by
Microorganisms ............................................... 3:145
3.5.5 The Future of Microbial Oils ............................. 3:147
Acknowledgments .......................................................... 3:149
References .................................................................... 3:150
3.6 Transgenic Oils .................................................................... 3:155
3.6.1 Introduction ..................................................... 3:155
3.6.2 Technology for Altering Fatty Acid
Composition .................................................... 3:158
3.6.3 Canola from Traditional Breeding of Oilseed
Crops ............................................................... 3:159
3.6.4 High-oleic Sunflower from Mutagenesis of
Oilseed Crops .................................................. 3:160
3.6.5 Applications of High-oleate Oils ....................... 3:160
3.6.6 Altered Polyunsaturate Content through
Mutagenesis .................................................... 3:162

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3.6.7 Improved Oil Composition of a Transgenic

Soybean .......................................................... 3:162
3.6.8 Improved Industrial Use from Genetically
Engineering Oilseed Crops .............................. 3:163
3.6.9 Future Directions for Transgenic Oilseeds ....... 3:164
3.6.10 Potential New Oils for Food, Feed, and
Industruial Use ................................................ 3:165
3.6.11 Issues Related to Transgenic Oilseeds ............ 3:167
References .................................................................... 3:172
3.7 Tree Nut Oils ........................................................................ 3:175
3.7.1 Introduction ..................................................... 3:175
3.7.2 Almond ............................................................ 3:176
3.7.3 Hazelnut .......................................................... 3:179
3.7.4 Pecan .............................................................. 3:182
3.7.5 Walnut ............................................................. 3:183
3.7.6 Pistachio .......................................................... 3:185
3.7.7 Brazil Nut ......................................................... 3:186
3.7.8 Pine Nut .......................................................... 3:186
3.7.9 Macadamia Nut ............................................... 3:187
3.7.10 Cashew Nut ..................................................... 3:188
3.7.11 Use of Defatted Tree Nut Meals and Other
Byproducts as Protein Sources ........................ 3:188
3.7.12 Concluding Remarks ....................................... 3:190
References .................................................................... 3:190
3.8 Germ Oils from Different Sources ........................................ 3:195
3.8.1 Introduction ..................................................... 3:195
3.8.2 Wheat Germ .................................................... 3:196
3.8.3 Corn Germ Oil ................................................. 3:207
3.8.4 Rice Bran Oil ................................................... 3:215
3.8.5 Oat and Barley Oil ........................................... 3:223
3.8.6 Conclusions ..................................................... 3:227

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References .................................................................... 3:227

3.9 Oils from Herbs, Spices, and Fruit Seeds ........................... 3:233
3.9.1 Introduction ..................................................... 3:233
3.9.2 Edible Seed Oils Rich in -linolenic Acid
(18:3n3) ........................................................... 3:234
3.9.3 Edible Seed Oils Rich in -linolenic Acid
(18:3n6) ........................................................... 3:239
3.9.4 Edible Seed Oils Rich in Linoleic Acid
(18:2n6) ........................................................... 3:241
3.9.5 Edible Seed Oils Rich in Oleic Acid
(18:1n-9) .......................................................... 3:248
3.9.6 Other Special Seed Oils of Fruit, Spice, and
Herb ................................................................ 3:254
3.9.7 Summary ......................................................... 3:255
References .................................................................... 3:256
3.10 Marine Mammal Oils ............................................................ 3:259
3.10.1 Introduction ..................................................... 3:259
3.10.2 Lipid Classes ................................................... 3:260
3.10.3 Fatty Acid Composition .................................... 3:262
3.10.4 Oxidative Stability ............................................ 3:267
3.10.5 Processing ....................................................... 3:268
3.10.6 Production of 3 Fatty Acid Concentrates ....... 3:269
3.10.7 Applications ..................................................... 3:271
3.10.8 Health Benefits and Disease Prevention .......... 3:272
3.10.9 Health Effects of DPA ...................................... 3:273
3.10.10 Comparison of Fish Oil and Marine Mammal
Oil .................................................................... 3:274
Reference ...................................................................... 3:275
3.11 Fish Oils ................................................................................ 3:279
3.11.1 Introduction ..................................................... 3:279
3.11.2 Why Do We Still Have Fish Oils? ..................... 3:282

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 Contents xxix

3.11.3 Fish Oil Fatty Acids and Gas-liquid

Chromatography .............................................. 3:284
3.11.4 Saturated, Isomeric Monoenoic, and Unusual
Fatty Acids ...................................................... 3:290
3.11.5 Polyunsaturated Fatty Acids ............................ 3:293
3.11.6 Fish Oil Production and Quality ....................... 3:296
3.11.7 Concentrates of Fish Oil Omega-3 Products .... 3:303
3.11.8 The Other Oils ................................................. 3:309
3.11.9 Conclusion ....................................................... 3:311
References .................................................................... 3:313
3.12 Minor Components of Fats and Oils .................................... 3:319
3.12.1 Introduction ..................................................... 3:319
3.12.2 The Chemistry of Minor Lipid Components ...... 3:321
3.12.3 Significance of Minor Lipid Components .......... 3:336
3.12.4 Analysis of Minor Lipid Components ................ 3:346
References .................................................................... 3:347
3.13 Lecithins ............................................................................... 3:361
3.13.1 Introduction ..................................................... 3:361
3.13.2 Sources of Phospholipids ................................ 3:362
3.13.3 Nomenclature, Classification, Structure and
Composition, and Chemical/Physical
Properties ........................................................ 3:372
3.13.4 Manufacture, Fractionation, and Purification
of Lecithins ...................................................... 3:384
3.13.5 Food-grade Lecithin Products, Uses ................ 3:400
3.13.6 Animal Feeds, Uses ........................................ 3:420
3.13.7 Nonfood and Industrial Uses ........................... 3:427
3.13.8 Availability and Economics .............................. 3:438
3.13.9 Regulatory Aspects ......................................... 3:439
3.13.10 Future Prospects ............................................. 3:440
Acknowledgments .......................................................... 3:440

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xxx Contents

References .................................................................... 3:440

3.14 Lipid Emulsions .................................................................... 3:457
3.14.1 Introduction ..................................................... 3:457
3.14.2 Definitions ....................................................... 3:458
3.14.3 Droplet Characteristics .................................... 3:460
3.14.4 Emulsion Preparation ...................................... 3:468
3.14.5 Physicochemical Properties of Food
Emulsions ........................................................ 3:480
3.14.6 Conclusions ..................................................... 3:496
References .................................................................... 3:497
3.15 Dietary Fat Substitutes ......................................................... 3:503
3.15.1 Introduction ..................................................... 3:503
3.15.2 Reduced-calorie Structured Lipids as Fat
Substitutes ...................................................... 3:510
3.15.3 Fat Substitutes Based on Esters and Ethers .... 3:516
3.15.4 Fat Mimetics Based on Carbohydrates ............ 3:528
3.15.5 Fat Mimetics Based on Proteins ...................... 3:530
References .................................................................... 3:532
3.16 Structural Effects on Absorption, Metabolism, and
Health Effects of Lipids ........................................................ 3:535
3.16.1 Introduction ..................................................... 3:535
3.16.2 Stereospecific Effects of Fat Digestion and
Related Phenomena ........................................ 3:537
3.16.3 Differences in Metabolism between Esterified
and Free Fatty Acids ....................................... 3:543
3.16.4 Postprandial Effects ......................................... 3:545
3.16.5 Effects of Stereospecific Structure of Dietary
Acylglycerols on Chylomicron Clearing and
Tissue Targeting .............................................. 3:547
3.16.6 Effects of Stereospecific Structure of Dietary
Triacylglycerols on Their Health-related
Nutritional Effects ........................................... 3:547

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 Contents xxxi

3.16.7 Effects Related to Triacylglycerol

Hydrophobicity ................................................. 3:548
3.16.8 Effect of Acylglycerol Structure on Nutritional
Effects ............................................................. 3:549
3.16.9 Semi-synthetic Food Fats without
Acylglycerol Structure ...................................... 3:550
3.16.10 Conclusion ....................................................... 3:550
References .................................................................... 3:551
3.17 Modification of Fats and Oils via Chemical and
Enzymatic Methods .............................................................. 3:555
3.17.1 Introduction ..................................................... 3:555
3.17.2 Hydrogenation ................................................. 3:556
3.17.3 Fractionation .................................................... 3:557
3.17.4 Blending .......................................................... 3:558
3.17.5 Interesterification ............................................. 3:558
3.17.6 Hydrolysis and Esterification ............................ 3:569
3.17.7 Lipases in Lipid Modification ............................ 3:571
3.17.8 Modification of Fats and Oils to Produce
Structured Lipids ............................................. 3:579
References .................................................................... 3:582
3.18 Novel Separation Techniques for Isolation and
Purification of Fatty Acids and Oil by-products .................... 3:585
3.18.1 Introduction ..................................................... 3:585
3.18.2 Methods of Obtaining Fatty Acids .................... 3:586
3.18.3 Separation of Byproduct Components ............. 3:607
References .................................................................... 3:614

Volume 4. Edible Oil and Fat Products: Products

and Applications
4.1 Frying Oils ............................................................................ 4:1
4.1.1 Introduction ..................................................... 4:1
4.1.2 Role of Oil or Fat in Frying ............................... 4:3

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xxxii Contents

4.1.3 Applications of Frying Oil ................................. 4:3

4.1.4 Selection of Frying Oil ..................................... 4:4
4.1.5 The Frying Process ......................................... 4:5
4.1.6 Chemical Reactions Occurring in Oil during
Frying .............................................................. 4:7
4.1.7 Sources of Free Radicals ................................ 4:11
4.1.8 Polymerization ................................................. 4:11
4.1.9 Complexity of Oil Reactions in Frying .............. 4:12
4.1.10 Analytical Requirements for Fresh Frying
Oil .................................................................... 4:14
4.1.11 Impact of Tocopherols and Tocotrienols in
Frying Oil ......................................................... 4:16
4.1.12 Factors Affecting Frying Oil Quality ................. 4:17
4.1.13 Quality Standards of Oils (Table 3) .................. 4:19
4.1.14 Comments on Palm Oil .................................... 4:20
4.1.15 Enhancement of Frying Oil Performance ......... 4:21
4.1.16 Storage and Transportation of Frying Oil ......... 4:22
4.1.17 Hydrogenation and Trans-fat ........................... 4:23
4.1.18 Alternatives to Trans-fats ................................. 4:25
4.1.19 Frying Shortening versus Frying Oils ............... 4:27
4.1.20 Summary ......................................................... 4:28
References .................................................................... 4:29
4.2 Margarines and Spreads ...................................................... 4:33
4.2.1 Historical Development of Margarine (47) ...... 4:35
4.2.2 U.S. Trends ..................................................... 4:36
4.2.3 Regulatory Status in the United States ............ 4:37
4.2.4 Product Characteristics ................................... 4:42
4.2.5 Oils Used in Vegetable Oil Margarines and
Spreads ........................................................... 4:45
4.2.6 Other Common Ingredients ............................. 4:58
4.2.7 Processing ....................................................... 4:63

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 Contents xxxiii

4.2.8 Low-calorie Spreads ........................................ 4:68

4.2.9 Balanced Spreads ........................................... 4:70
4.2.10 Deterioration and Shelf Life ............................. 4:71
References .................................................................... 4:73
4.3 Shortenings: Science and Technology ................................ 4:83
4.3.1 Introduction ..................................................... 4:83
4.3.2 Plastic Theory .................................................. 4:88
4.3.3 Formulation ..................................................... 4:89
4.3.4 Manufacturing Processes and Equipment ........ 4:94
4.3.5 Shortening Production Systems ....................... 4:106
4.3.6 Analytical Evaluation and Quality Control ........ 4:114
4.3.7 Packaging and Storage ................................... 4:116
4.3.8 Innovations ...................................................... 4:117
References .................................................................... 4:123
4.4 Shortenings: Types and Formulations ................................. 4:125
4.4.1 Introduction ..................................................... 4:125
4.4.2 Shortening Attributes ....................................... 4:132
4.4.3 Base Stock System ......................................... 4:137
4.4.4 Shortening Formulation ................................... 4:140
4.4.5 Shortening Crystallization ................................ 4:147
4.4.6 Plasticized Shortening Consistency ................. 4:149
4.4.7 Liquid Opaque Shortenings ............................. 4:153
4.4.8 Shortening Chips and Flakes ........................... 4:155
References .................................................................... 4:156
4.5 Confectionery Lipids ............................................................. 4:159
4.5.1 Introduction ..................................................... 4:159
4.5.2 Chemistry of Chocolate ................................... 4:159
4.5.3 Characteristics of Cocoa Butter ....................... 4:160
4.5.4 Confectionery Fats .......................................... 4:165
4.5.5 Hard Butters .................................................... 4:168
4.5.6 Lauric CBS ...................................................... 4:168

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4.5.7 Non-lauric CBS ................................................ 4:170

4.5.8 Cocoa Butter Equivalents (CBEs) .................... 4:170
4.5.9 Organic Chocolate and Confectionery ............. 4:171
4.5.10 Recipe Engineering and Oil Processing ........... 4:172
4.5.11 Conclusions and Future Prospectives .............. 4:173
References .................................................................... 4:173
4.6 Cooking Oils, Salad Oils, and Dressings ............................. 4:175
4.6.1 Introduction ..................................................... 4:175
4.6.2 Natural and Processed Cooking and Salad
Oils .................................................................. 4:176
4.6.3 Stability of Salad and Cooking Oils .................. 4:178
4.6.4 Quality Evaluation of Salad and Cooking
Oils .................................................................. 4:180
4.6.5 Additives for Salad and Cooking Oils ............... 4:183
4.6.6 Nutrition-oriented Salad and Cooking Oils ....... 4:184
4.6.7 New Salad and Cooking Oils ........................... 4:184
4.6.8 Oil-based Dressings ........................................ 4:185
4.6.9 Viscous or Spoonable Dressings ..................... 4:185
4.6.10 Pourable Dressings ......................................... 4:191
4.6.11 Reduced-calorie Dressings .............................. 4:196
4.6.12 Fat-free Dressings ........................................... 4:198
4.6.13 Refrigerated Dressings .................................... 4:200
4.6.14 Heat-stable Dressings ..................................... 4:200
References .................................................................... 4:201
4.7 Fats and Oils in Bakery Products ........................................ 4:207
4.7.1 Introduction ..................................................... 4:207
4.7.2 Bread and Rolls ............................................... 4:208
4.7.3 Layered Doughs .............................................. 4:210
4.7.4 Cakes .............................................................. 4:212
4.7.5 Cake Donuts .................................................... 4:215
4.7.6 Cookies ........................................................... 4:216

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 Contents xxxv

4.7.7 Pie Crust, Biscuits ........................................... 4:219

4.7.8 Specifications for Bakery Shortenings ............. 4:219
References .................................................................... 4:227
4.8 Emulsifiers for the Food Industry ......................................... 4:229
4.8.1 Emulsifiers as Amphiphiles .............................. 4:229
4.8.2 Surfaces and Interfaces in Foods .................... 4:231
4.8.3 Surface Activity ................................................ 4:231
4.8.4 Emulsions ........................................................ 4:236
4.8.5 Foams ............................................................. 4:242
4.8.6 Wetting ............................................................ 4:243
4.8.7 Physical State of Emulsifier Plus Water ........... 4:244
4.8.8 Emulsifiers for Food Applications ..................... 4:248
4.8.9 Interactions with Other Food Components ....... 4:256
4.8.10. Some Food Applications .................................. 4:261
References .................................................................... 4:266
4.9 Frying of Foods and Snack Food Production ...................... 4:269
4.9.1 Introduction ..................................................... 4:269
4.9.2 Frying Process ................................................ 4:270
4.9.3 Types of Restaurant Fryers ............................. 4:270
4.9.4 Safety Issues ................................................... 4:277
4.9.5 Improving Restaurant Fryer Operation ............. 4:278
4.9.6 Measuring Oil Quality in the Fryer ................... 4:279
4.9.7 Physical Testing Devices ................................. 4:280
4.9.8 Chemical Tests ................................................ 4:282
4.9.9 Filtration and Treatment of Oil ......................... 4:284
4.9.10 Industrial Frying ............................................... 4:285
4.9.11 The Purpose of Frying Foods .......................... 4:288
4.9.12 Difference between the Frying and Other
Cooking Methods ............................................. 4:289
4.9.13 What Happens during Frying? .......................... 4:289
4.9.14 Types of Industrial Fryers ................................ 4:290

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xxxvi Contents

4.9.15 Criteria for Fryer Selection ............................... 4:294

4.9.16 Components in an Industrial Frying System ..... 4:295
4.9.17 Continuous Potato Chip Process ..................... 4:296
4.9.18 Extruded Products ........................................... 4:299
4.9.19 Heat Wave Fryers ............................................ 4:303
4.9.20 Evolution of the Frying Industry into Diverse
Products .......................................................... 4:304
4.9.21 Low Oil Snacks ................................................ 4:304
4.9.22 Generation of Fines and Their Removal .......... 4:305
4.9.23 Terminology Used in Industrial Frying ............. 4:307
4.9.24 Fryer Capacity ................................................. 4:307
4.9.25 Key Points in Determining the Fryer Size ........ 4:308
4.9.26 Heat Load Requirement ................................... 4:310
4.9.27 Air Requirement (for Combustion) ................... 4:313
4.9.28 Product Bulk Density ....................................... 4:313
4.9.29 Oil Quality Management .................................. 4:313
4.9.30 Fryer Sanitation ............................................... 4:314
4.9.31 Summary ......................................................... 4:314
References .................................................................... 4:315
4.10 Fats and Oils in Feedstuffs and Pet Foods ......................... 4:317
4.10.1 History ............................................................. 4:319
4.10.2 Information Sources, Authorities, and
Obligations ...................................................... 4:320
4.10.3 Availability, Characteristics, and
Composition .................................................... 4:323
4.10.4 Digestion Metabolism and Fats Feeding
Requirements .................................................. 4:341
4.10.5 Fat Utilization Practices ................................... 4:367
References .................................................................... 4:386
4.11 By-product Utilization ........................................................... 4:391
4.11.1 By-products of Seed Processing ...................... 4:391

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 Contents xxxvii

4.11.2 By-products of Oil Refining .............................. 4:405

References .................................................................... 4:413
4.12 Environmental Impact and Waste Management ................. 4:417
4.12.1 Introduction ..................................................... 4:417
4.12.2 Process Components and Major Wastewater
Sources ........................................................... 4:418
4.12.3 Process Factors Affecting Wastewater
Generation and Characteristics ....................... 4:421
4.12.4 Air Emissions, Sources, and Controls .............. 4:423
4.12.5 Solid and Hazardous Wastes, Sources, and
Controls ........................................................... 4:427
4.12.6 Current Issues ................................................. 4:429
4.12.7 Wastewater Treatment Processes and
Technologies ................................................... 4:431
References .................................................................... 4:440

Volume 5. Edible Oil and Fat Products: Processing

Technologies
5.1 A Primer on Oils Processing Technology ............................ 5:1
5.1.1 Introduction ..................................................... 5:1
5.1.2 Storage ............................................................ 5:2
5.1.3 Preparation ...................................................... 5:5
5.1.4 Mechanical Extraction ..................................... 5:9
5.1.5 Solvent Extraction ............................................ 5:11
5.1.6 Degumming, Lecithin Processing, and
Physical Refining Pretreatment ........................ 5:16
5.1.7 Caustic Refining .............................................. 5:20
5.1.8 Bleaching ........................................................ 5:25
5.1.9 Dewaxing ........................................................ 5:29
5.1.10 Hydrogenation ................................................. 5:33
5.1.11 Interesterification ............................................. 5:37
5.1.12 Fractionation .................................................... 5:39

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xxxviii Contents

5.1.13 Deodorization and Physical Refining ............... 5:42

5.1.14 Shortening and Margarine Manufacturing ........ 5:48
5.1.15 Acidulation ....................................................... 5:53
5.1.16 Summary ......................................................... 5:54
References .................................................................... 5:55
General References ....................................................... 5:56
5.2 Oil Extraction ........................................................................ 5:57
5.2.1 Evolution of Oil Extraction ............................... 5:57
5.2.2 Seed Preparation ............................................. 5:63
5.2.3 Mechanical Extraction ..................................... 5:71
5.2.4 Solvent Extraction ............................................ 5:75
5.2.5 Summary ......................................................... 5:97
References .................................................................... 5:97
5.3 Recovery of Oils and Fats from Oilseeds and Fatty
Materials ............................................................................... 5:99
5.3.1 Introduction ..................................................... 5:99
5.3.2 Mechanical Pretreatment ................................. 5:102
5.3.3 Heat Pretreatment ........................................... 5:109
5.3.4 Mechanical Expression of Oil .......................... 5:128
5.3.5 Solvent Extraction ............................................ 5:142
5.3.6 Types of Extractors .......................................... 5:160
5.3.7 Recovery of Solvent ........................................ 5:172
5.3.8 Obtaining Oil from Fruit Pulps .......................... 5:180
Acknowledgements ........................................................ 5:182
References .................................................................... 5:182
5.4 Storage, Handling, and Transport of Oils and Fats ............. 5:191
5.4.1 Introduction ..................................................... 5:191
5.4.2 Storage and Handling ...................................... 5:200
5.4.3 Deterioration Processes .................................. 5:220
5.4.4 Conclusions and Future Perspectives .............. 5:226
References .................................................................... 5:226

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 Contents xxxix

5.5 Packaging ............................................................................. 5:231

5.5.1 Conceptual Design of Packaging Systems for
Oil Products ..................................................... 5:231
5.5.2 Preliminary Engineering .................................. 5:238
5.5.3 Final Engineering ............................................ 5:241
5.5.4 Packaging Systems Components .................... 5:244
5.5.5 Edible Oil Operations ....................................... 5:258
5.5.6 Bulk Packaging Operations ............................. 5:262
5.5.7 Summary ......................................................... 5:263
5.5.8 Future Considerations ..................................... 5:264
References .................................................................... 5:264
5.6 Adsorptive Separation of Oils .............................................. 5:267
5.6.1 Definitions ....................................................... 5:267
5.6.2 Mathematical Models ....................................... 5:268
5.6.3 Mechanisms .................................................... 5:279
5.6.4 Mechanics ....................................................... 5:280
References .................................................................... 5:282
5.7 Bleaching .............................................................................. 5:285
5.7.1 Introduction ..................................................... 5:285
5.7.2 Background and Historical Perspective ........... 5:286
5.7.3 Adsorptive Purification Agents Description/
Preparation/Properties ..................................... 5:287
5.7.4 Trace Constituents in Lipid Oils and Fats ........ 5:297
5.7.5 Adsorptive Purification Process: General
Description ...................................................... 5:314
References .................................................................... 5:335
5.8 Deodorization ....................................................................... 5:341
5.8.1 Introduction ..................................................... 5:341
5.8.2 Deodorization Principle .................................... 5:343
5.8.3 Refined Oil Quality ........................................... 5:349
5.8.4 Deodorizer Technology .................................... 5:363

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xl Contents

5.8.5 Commercial Deodorizer Systems .................... 5:376

5.8.6 Future Challenges ........................................... 5:381
References .................................................................... 5:382
5.9 Hydrogenation: Processing Technologies ........................... 5:385
5.9.1 Introduction ..................................................... 5:385
5.9.2 Is There a Future for Hydrogenation? .............. 5:390
5.9.3 Research on Trans-reduction by
Hydrogenation ................................................. 5:390
5.9.4 The Trans-fat Issue ......................................... 5:391
5.9.5 Hydrogen Supply for Hydrogenation ................ 5:394
References .................................................................... 5:395
5.10 Supercritical Technologies for Further Processing of
Edible Oils ............................................................................ 5:397
5.10.1 Introduction ..................................................... 5:397
5.10.2 Definition and Properties of Supercritical
Fluids ............................................................... 5:398
5.10.3 Historic Development and Commercial
Applications ..................................................... 5:399
5.10.4 Solubility Behavior of Lipid Components .......... 5:400
5.10.5 Supercritical Fluid Processing of Fats and
Oils .................................................................. 5:408
5.10.6 Novel Process Development: an Integrated
Approach ......................................................... 5:423
References .................................................................... 5:424
5.11 Membrane Processing of Fats and Oils .............................. 5:433
5.11.1 Introduction ..................................................... 5:433
5.11.2 Composition of Crude Vegetable Oils .............. 5:434
5.11.3 Crude Vegetable Oil Refining .......................... 5:434
5.11.4 Vegetable Oil Degumming ............................... 5:435
5.11.5 Membrane Processing of Oils and Fats ........... 5:437
5.11.6 Conclusions ..................................................... 5:456
References .................................................................... 5:457

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 Contents xli

5.12 Margarine Processing Plants and Equipment ..................... 5:459

5.12.1 Crystallization of Oil and Fat Products ............. 5:460
5.12.2 Processing Equipment for Margarine and
Related Fat Products ....................................... 5:469
5.12.3 Refrigerants for the Future ............................... 5:498
5.12.4 Plant Layout and Process Flowsheet ............... 5:499
5.12.5 Processing of Low-fat Spreads, Puff Pastry
Margarine, and Puff Pastry Butter .................... 5:511
5.12.6 Production Control, Quality Control, and
Sanitation ........................................................ 5:523
References .................................................................... 5:528
5.13 Extrusion Processing of Oilseed Meals for Food and
Feed Production ................................................................... 5:533
5.13.1 Introduction ..................................................... 5:533
5.13.2 Types of Extruders .......................................... 5:534
5.13.3 Why Process Oilseed with Extrusion? ............. 5:538
5.13.4 Soybeans Can Be Converted into Full-fat
Soy by Using Dry or Wet Extruders ................. 5:546
5.13.5 Extrusion-expelling of Oilseeds ....................... 5:554
5.13.6 Extrusion-expelling of Soybeans ...................... 5:554
5.13.7 Nutritional Advantages of Extrusion-expelling
of Oilseeds ...................................................... 5:559
5.13.8 Mechanical Crushing with Expanders .............. 5:563
5.13.9 Extrusion of Oilseeds before Extraction ........... 5:564
5.13.10 Extrusion of High Oilseeds .............................. 5:567
References .................................................................... 5:569

Volume 6. Industrial and Nonedible Products from

Oils and Fats
6.1 Fatty Acids and Derivatives from Coconut Oil ..................... 6:1
6.1.1 The Worlds Fats and Oils Output .................... 6:1

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xlii Contents

6.1.2 The Role of Coconut Oil in the Oleochemical

Industry Worldwide .......................................... 6:2
6.1.3 Types of Fatty Acids and Derivatives from
Coconut Oil and Their General Applications .... 6:4
6.1.4 Fatty Acids ...................................................... 6:7
6.1.5 Methyl Esters ................................................... 6:13
6.1.6 Fatty Alcohols .................................................. 6:21
6.1.7 Glycerine ......................................................... 6:29
6.1.8 Monoalkyl Phosphates ..................................... 6:36
6.1.9 Alkanolamides ................................................. 6:39
6.1.10 Surfactants ...................................................... 6:43
6.1.11 Tertiary Amines ............................................... 6:52
References .................................................................... 6:54
6.2 Rendering ............................................................................. 6:57
6.2.1 Introduction ..................................................... 6:57
6.2.2 Modern Day Rendering .................................... 6:58
6.2.3 Byproducts ...................................................... 6:60
6.2.4 Processing ....................................................... 6:66
6.2.5 Product Composition ....................................... 6:75
6.2.6 Proteins ........................................................... 6:78
6.2.7 Fats ................................................................. 6:79
6.2.8 Oleochemistry ................................................. 6:82
6.2.9 Refining ........................................................... 6:85
6.2.10 Bleaching or Color Reduction .......................... 6:86
6.2.11 Uses of Refined and Bleached Fats ................ 6:87
6.2.12 Hydrogenation and Hydrogenated Products .... 6:87
6.2.13 Trans-esterification and Fatty Acid Esters ....... 6:89
6.2.14 Bio-fuel and Bio-diesel Products ...................... 6:93
6.2.15 Governmental Regulations .............................. 6:95
6.2.16 Environmental Issues ...................................... 6:98
6.2.17 Future Outlook ................................................. 6:99

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 Contents xliii

References .................................................................... 6:100

6.3 Soaps ................................................................................... 6:103
6.3.1 Introduction ..................................................... 6:103
6.3.2 Physical Properties of Surfactants ................... 6:104
6.3.3 Soap Raw Materials and Their Processing ...... 6:105
6.3.4 Soap Solution-phase Properties ...................... 6:108
6.3.5 Soap Solid-phase Properties and
Crystallization .................................................. 6:111
6.3.6 Commercial Processing ................................... 6:113
6.3.7 Bar Soap Manufacturing .................................. 6:122
6.3.8 Formulation of Soaps ...................................... 6:126
6.3.9 Economic Aspects ........................................... 6:132
6.3.10 Analytical Characterization of Soap ................. 6:132
6.3.11 Health, Safety, and Toxicology ........................ 6:133
6.3.12 Additional Uses of Soap .................................. 6:133
References .................................................................... 6:134
General References ....................................................... 6:136
6.4 Detergents and Detergency ................................................. 6:137
6.4.1 Introduction ..................................................... 6:137
6.4.2 Components of Detersive Systems .................. 6:140
6.4.3 Formulation ..................................................... 6:142
6.4.4 Surfactants ...................................................... 6:142
6.4.5 Factors Influencing Detergency ....................... 6:149
6.4.6 Mechanisms .................................................... 6:156
6.4.7 Solid-soil Detergency ....................................... 6:158
6.4.8 Oily-soil Detergency ........................................ 6:164
6.4.9 Measurement of Detergency ............................ 6:168
6.4.10 Fabric Detergency ........................................... 6:169
6.4.11 Hard-surface Detergency ................................. 6:170
6.4.12 Detergent Manufacture .................................... 6:173
6.4.13 Analysis ........................................................... 6:176

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xliv Contents

6.4.14 Health and Safety Factors ............................... 6:176

6.4.15 Environmental Considerations ......................... 6:179
References .................................................................... 6:181
General References ....................................................... 6:187
6.5 Glycerine .............................................................................. 6:191
6.5.1 Introduction ..................................................... 6:191
6.5.2 Processing Principals and Details .................... 6:194
6.5.3 Processing Plants ............................................ 6:212
6.5.4 Properties of Glyceine ..................................... 6:215
6.5.5 Quality and Testing .......................................... 6:216
6.5.6 Processing Losses .......................................... 6:218
6.5.7 Waste Management ........................................ 6:219
6.5.8 Uses, Applications, and Economics ................. 6:219
6.5.9 Future Considerations ..................................... 6:221
References .................................................................... 6:221
6.6 Vegetable Oils as Biodiesel ................................................. 6:223
6.6.1 Introduction ..................................................... 6:223
6.6.2 Biodiesel Quality .............................................. 6:224
6.6.3 Biodiesel and Diesel Emissions ....................... 6:230
6.6.4 Resources for Biodiesel Production ................. 6:233
6.6.5 Production Technology .................................... 6:234
6.6.6 Utilization Technology ..................................... 6:246
6.6.7 Coproduct Use ................................................ 6:251
6.6.8 The Future ....................................................... 6:252
References .................................................................... 6:252
6.7 Vegetable Oils as Lubricants, Hydraulic Fluids, and
Inks ....................................................................................... 6:259
6.7.1 Introduction ..................................................... 6:259
6.7.2 Vegetable Oil Structure and Composition ........ 6:260
6.7.3 Oxidative Stability ............................................ 6:261
6.7.4 Low-temperature Properties ............................ 6:269

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6.7.5 Viscosities, Pour Points, and Oxidative

Degradation Tendencies of Major Lubricant
Basestocks ...................................................... 6:272
6.7.6 Effect of Diluent and Additives on Low-
temperature Properties .................................... 6:274
6.7.7 Conclusions ..................................................... 6:275
References .................................................................... 6:276
6.8 Vegetable Oils in Production of Polymers and Plastics ...... 6:279
6.8.1 Introduction ..................................................... 6:279
6.8.2 Polymers from Renewable Resources ............. 6:280
6.8.3 Exploitation of the Functional Groups on
Triglycerol Molecules for the Production of
Polymers ......................................................... 6:289
6.8.4 Use of Naturally Functionalized
Triacylglycerol Oils in Interpenetrating
Polymer Networks ........................................... 6:299
6.8.5 Conclusions ..................................................... 6:303
References .................................................................... 6:303
6.9 Paints, Varnishes, and Related Products ............................ 6:307
6.9.1 Relationship of Fats and Oils to the Paint-
coating Industry ............................................... 6:307
6.9.2 A Brief Overview of the Coatings
Technology ...................................................... 6:309
6.9.3 Film Drying Process of Oil-based Coating
Materials .......................................................... 6:314
6.9.4 Oleoresinous Varnishes ................................... 6:318
6.9.5 Alkyd Resins .................................................... 6:319
6.9.6 Safety and Environmental Precautions ............ 6:343
6.9.7 Modification of Alkyd Resins by Blending
with Other Polymers ........................................ 6:343
6.9.8 Economic Aspects ........................................... 6:348
6.9.9 Future Prospects ............................................. 6:349

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xlvi Contents

References .................................................................... 6:349

6.10 Leather and Textile Uses of Fats and Oils .......................... 6:353
6.10.1 General Use of Fats and Oils in Leather .......... 6:353
6.10.2 Softening of Leather ........................................ 6:354
6.10.3 Softening with Fatliquor ................................... 6:355
6.10.4 Other Softening Materials ................................ 6:358
6.10.5 Evaluating Effects of Fat in Leather ................. 6:359
6.10.6 General Use of Fats and Oil for Textiles .......... 6:359
6.10.7 Common Textile Fibers .................................... 6:360
6.10.8 Processing of Fibers ........................................ 6:360
6.10.9 Physical Effects of Oils and Fats on Fibers
and Yarns ........................................................ 6:362
6.10.10 Oils and Fats in Textile Processing .................. 6:365
6.10.11 Concluding Remarks ....................................... 6:367
References .................................................................... 6:367
6.11 Edible Films and Coatings from Soybean and Other
Protein Sources .................................................................... 6:371
6.11.1 Edible Films and Coatings ............................... 6:371
6.11.2 Protein Films ................................................... 6:374
References .................................................................... 6:388
6.12 Pharmaceutical and Cosmetic Use of Lipids ....................... 6:391
6.12.1 Introduction ..................................................... 6:391
6.12.2 Lipids in Disease Prevention and Treatment .... 6:393
6.12.3 Lipids in Drug Delivery ..................................... 6:396
6.12.4 Lipids in Cosmetic Applications ....................... 6:400
6.12.5 Processing Oils for Pharmaceutical and
Cosmetics Applications ................................... 6:404
References .................................................................... 6:408

Index .................................................................................. I:1

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