Natural and Synthetic Waxes A compilation of all relevant information for the production and use of waxes in technical applications Waxes are among the oldest organic substances used by mankind. Before all others, beeswax is known to have played a role in human history for thousands of years. But over time, many other wax species have been detected and exploited, and prepared for different utilizations. Today, we possess knowledge of a great variety of different types of waxes. Unfortunately, there still is no broadly accepted definition of a wax: for the relatively few wax chemists, waxes are usually defined by their physico-chemical properties more than by their chemical constitution. Waxes are not uniform but oligomeric and polymeric substances, not simply describable with a chemical formula. The realm of waxes encompasses fully or partly natural, refined, partly or fully synthetic products, which can be extended by “wax-like” products which do not fulfil all definition criteria. Waxes are offered in different forms like pellets, granules, powders, or micropowders. Their number of technical applications runs into thousands. However, waxes in most cases are just adjuvants or additives, and with few exceptions like candles not known to a broader public. Only few publications over the last decades tried to present a more comprehensive overview of heir chemistry, chemical composition, their physical and analytical properties, their applications, and their sometimes astonishing history. Based on personal experience and expertise, the authors intend to present an overview on the main classes of waxes, their origin, history, future, and potential fate. Economical aspects like market size and development, ecological impacts and challenges, and regulatory issues are also addressed. Waxes are indispensable products in everyday life and in industry and technology, though mostly not even visible or distinguishable to experts. They deserve more than the role of a “poor cousin” in chemistry and technology.

Table of Contents:
Foreword xxv Part I Natural Waxes 1 1 Introduction 3 1.1 General Survey of Waxes 3 1.2 Definitions of Waxes 3 1.3 Brief History of Waxes 5 1.4 Origin of Natural Waxes 18 References 20 2 Waxes in Arts 23 2.1 Waxes in Paintings 23 2.2 Pre-encaustic Painting 24 2.3 The Faiyum Mummy Portraits 25 2.4 Greece and Rome 26 2.5 Post Roman Wax Paintings 27 2.6 Revival of Encaustic 28 2.7 Wax, Effigies, Sculptures, and Masks 30 2.8 Votive Figures in Religion 35 2.9 Wax as Processing Aid in Arts and Craft 37 2.10 Waxes, Crafts, and Arts in the New World 41 2.11 Wax Museums 44 2.12 Summary 45 References 45 3 Photosynthesis of Plant Waxes 47 3.1 Chemical Composition of Plant Waxes 48 3.2 The Biochemical Pathway to Plant Waxes 48 3.3 Photosynthesis to Plant Waxes 49 3.4 Relevant Phases of Photosynthesis: The First Stage of Plant Wax Production 51 3.5 Recent Research Results 55 3.6 From the Calvin Cycle to Wax 56 3.7 Artificial Photosynthesis and Engineering Natural Waxes 60 References 62 Section I Natural Waxes 65 Reference 66 4 The Natural Animal Waxes 67 5 Insect Waxes 69 5.1 Beeswax 69 References 87 6 Other Insect Waxes 89 6.1 Ghedda (Gedda) Wax 89 6.2 Chinese Insect Wax 92 6.3 Shellac Wax 94 References 101 7 Mammalian Animal Waxes 103 7.1 Introduction 103 7.2 Wool Wax 104 7.3 Mammalian Marine Waxes 113 7.4 Mammalian Human Waxes: Earwax/Cerumen 117 7.5 Marine Waxes 121 7.6 Other Marine Waxes 122 7.7 Bird Waxes 123 References 124 Section II Natural Plant Waxes 127 8 Carnaúba Wax 129 8.1 Introduction 129 8.2 History 130 8.3 General Properties of Carnaúba Wax 132 8.4 Economic Aspects 133 8.5 Origin 133 8.6 Occurrence and Exploitation 134 8.7 Harvesting Carnaúba 135 8.8 Grinding 137 8.9 Micronization 137 8.10 Carnaúba-Wax-Based Emulsions 138 8.11 Types and Specifications 138 8.12 Uses and Applications of Carnaúba Wax Grades 140 8.13 Cosmetics 142 8.14 Care Products 142 8.15 Candles 144 8.16 Printing Inks 144 8.17 Plastics Industry 145 8.18 Varnishes/Coatings 145 8.19 Economic Outlook 145 8.20 Physical and Chemical Properties 146 8.21 Chemical Composition of Carnaúba Wax 146 8.22 Physiological and Toxicological Aspects of Carnaúba Wax 148 8.23 Registration Status 149 8.24 Policosanol in Carnaúba Wax 150 References 150 9 Candelilla or the “Great Wax Rush” 153 9.1 History 153 9.2 Occurrence and Isolation 153 9.3 Working Up Candelilla 156 9.4 The Candelilla Wax Value Chain 157 9.5 Main Applications and Uses of Candelilla Wax 157 9.6 Physical and Chemical Properties and Composition of Candelilla Wax 159 9.7 Economic Aspects 162 9.8 Comparison Between Candelilla and Sugarcane Wax 163 9.9 Registration Status 164 References 165 10 Montan Wax 167 10.1 A General Description 167 10.2 The Future of Montan Wax 169 10.3 Formation and Occurrence of Montan Wax 169 10.4 The Origin of Montan Wax 169 10.5 Separation of Montan Wax from Lignite 171 10.6 Extraction 171 10.7 Details of Montan Wax Production 172 10.8 Properties and Composition 173 10.9 Montan Wax Components 174 10.10 Resins and Dark Residues 176 10.11 Applications for Crude Montan Wax 177 10.12 Refining and Derivatization 177 10.13 Further Processing and Refining of Bleached Montan Wax 181 10.14 Derivatization 182 10.15 Uses and Economic Aspects 183 10.16 Selected Technical Applications for Montan Waxes 185 10.17 Registration Status 192 10.18 Montan Wax and Other Natural Wax Substitutes from Linear Alpha Olefins 192 10.19 Modified Linear Alpha Olefin Waxes 194 10.20 Production of Linear Alpha-olefins 196 10.21 Summary of Applications of Alpha-Olefins 200 10.22 Short Overview of Technical Applications of Linear Alpha-olefin Waxes 201 10.23 Peat Wax 202 10.24 Ozokerite Wax 203 References 205 11 Sugarcane Wax 209 11.1 Introduction–General Considerations 209 11.2 Occurrence and Isolation 209 11.3 Production of Sugarcane Worldwide (2018) 210 11.4 Composition of Sugarcane Wax 211 11.5 Separation of Sugarcane Wax 211 11.5.1 Value Chain of Sugar: The Indian Company Godavari Biorefineries Ltd. 211 11.6 Delivery Forms and Composition 213 11.7 Production 214 11.8 Further Applications of Sugarcane Wax 215 11.9 Medical and Dietary Aspects of Sugarcane Wax 216 11.10 Description of Policosanol 216 11.11 Rice Bran Wax 221 References 223 12 Japan Wax 227 12.1 General Reflections About Japan Wax 227 12.2 Refining Japan Wax 228 12.3 Chemical Composition of Japan Wax 229 12.4 Uses of Japan Wax 229 12.5 Economy 230 12.6 Registration Status 230 12.7 Castor Wax or Ricinus Wax 231 12.8 Ricinus communis Linnaeus: “The Umbrella Murder Case” 236 References 237 13 Palm Wax 239 13.1 General Considerations 239 13.2 Origin of Palm Oils 240 13.3 Agriculture of Oil Palm Trees 241 13.4 Extraction of Palm Oil 241 13.5 Palm Kernel Oil 241 13.6 Outlook 243 References 243 14 Wax of Manzanita Leaves 245 14.1 A General 245 14.2 Potential Medical Effects 247 14.3 Manzanita Roots and Smoking Pipes 247 References 248 15 Waxes of Citrus Fruits and Leaves 249 15.1 Chemical Composition 249 15.2 Primary Alcohol Carbon Length Distribution in Citrus Fruits and Leaves 252 15.3 Fatty Acids and Wax Acids Length Distribution 253 15.4 Waxes from Larrea Leaves and Stems 256 15.5 Sunflower Wax 259 15.6 Soy (or Soybean) Wax 262 15.7 Other Waxes from Hydrogenated Oils 263 15.8 Tea Wax 264 15.9 Jasmine Wax 265 15.10 Rose Wax 265 References 266 Part II Synthetic Waxes 269 16 Synthetic Waxes 271 16.1 Introduction 271 16.2 The Building Blocks of Synthetic Waxes: Monomers, Oligomers, and Polymers 272 16.3 Short Introduction to Molar Mass and Distributions 275 16.4 The Chemical Structure of Synthetic Polymer and Chemically Related Waxes 280 16.5 Molecular Structure of Synthetic and Petroleum Waxes 281 16.6 Discrimination Between Waxes and Plastics – A Brief Excursion into Polymer Physics 284 References 287 17 Polyolefin Waxes 289 17.1 General 289 17.2 Industrial Production of Ethylene Polymers: Plastics and Waxes 299 17.3 Market and Economics 316 17.4 Use and Applications 316 References 425 18 Polypropylene Waxes 433 18.1 General Overview 433 18.2 History of Polypropylene Plastics and Waxes 434 18.3 Polypropylene Plastics and Waxes: A Symbiotic Relationship 436 18.4 Chirality and Tacticity: Principles 437 18.5 PP Wax Polymerization Reactions and Processes 441 18.6 Polyethylene and Polypropene Plastics and Waxes: A Comparison 444 18.7 Properties of Polypropylene Waxes 446 18.8 Atactic Polypropylene Wax-like Materials (APO/APAO) 448 18.9 Applications of Polypropylene Waxes 449 18.10 Regulatory Aspects 454 18.11 Economic Aspects 454 References 455 19 Petroleum and Related Crude Oil-Based Waxes 457 19.1 Definitions 457 19.2 Introduction to Paraffin Waxes 458 19.3 History 459 19.4 Petroleum Wax Production from Crude Oil 460 19.5 Refinery Process 462 19.6 Petroleum Waxes are in Order of Refining 486 References 507 20 Fischer–Tropsch Synthesis (FTS) and Waxes 515 20.1 Introduction 515 20.2 History 516 20.3 Fischer–Tropsch Reaction Mechanism 517 20.4 Fischer–Tropsch Synthesis (FTS) 518 20.5 Fischer-Tropsch Waxes – Key Manufacturers 523 20.6 FT Waxes: Chemical and Physical Properties 523 20.7 Oxidized FT Waxes 524 20.8 Liquid Applications of Waxes 526 20.9 Regulatory Compliance 567 References 568 21 Amide Waxes 573 21.1 General 573 21.2 History of Amide Waxes 574 21.3 N,N ′ -Ethylenebis(stearamide): EBS 574 21.4 Applications 576 21.5 Stearamide Wax 588 21.6 Erucamide Wax 590 21.7 Oleamide Wax 592 21.8 Comparison of Anti-blocking and Slip Properties Between Erucamide, Stearamide, and Oleamide Waxes 594 21.9 N,N ′ -Ethylene-bis-Oleamide (EBO) 596 References 598 22 Polytetrafluoroethylene (PTFE) Waxes 601 22.1 Introduction 601 22.2 Resume 614 References 615 Appendix A Final Tables A.I–A.V: Listing of Aliphatic Compounds in Waxes 617 References 637 Appendix B Candles – A Most Popular Application Area for Waxes 639 B.1 Short Summary 639 B.2 Candles in Religion 642 B.3 Candles in Modern Science 646 References 647 Appendix C Test Methods for Characterizing Waxes 649 C.1 Test Methods for Waxes 649 C.2 Safety Data Sheets 651 Epilogue: The Future of Waxes 653 Index 655