Chemistry of Renewables: An Introduction

Foreword
Preface
Contents
1 The Overview - Introduction
	1.1  Definitions
	1.2  The Different Types of Renewable Raw Materials
	1.3  Comparison with Fossil Raw Materials
	1.4  Advantages and Disadvantages of Renewable Raw Materials
		BOX: The SWOT analysis
	References
I Fats and Oils
Anchor 2
2 The Raw Materials of Oleochemistry - Oil Plants
	2.1  Introduction to Oleochemistry
		BOX: The Lazy Oleochemist
	2.2  Overview of Important Vegetable Oils and Animal Fats
		2.2.1  Coconut Oil
			BOX: The Trained Monkeys
		2.2.2  Palm Oil and Palm Kernel Oil
			BOX: Quality Criteria for Oleochemists
		2.2.3  Rapeseed Oil
		2.2.4  Sunflower Oil
			BOX: MUFA or PUFA?
		2.2.5  Soybean Oil
		2.2.6  Linseed Oil from Flax Plants
		2.2.7  Castor Oil
		2.2.8  Olive Oil
		2.2.9  Safflower Oil
		2.2.10  Jatropha Oil
			BOX: An Oil that Is not an Oil at All
		2.2.11  Other Fats and Oils
			BOX: The Healthy Eskimo
	2.3  Some Numbers
	References
3 The Basics of Oleochemistry - Basic Oleochemicals
	3.1  Production of Basic Oleochemicals
		3.1.1  Fat Splitting
		3.1.2  Transesterification
		3.1.3  Saponification
		3.1.4  Direct Hydrogenation
			BOX: The Oleochemical Industry: Yesterday - Today - Tomorrow
	3.2  Reactions at the Carboxy Group of Fatty Acids
		3.2.1  Hydrogenation to Fatty  Alcohols
			BOX: Fatty Alcohols - A Retroperspective and a Look at the Competitors
		3.2.2  Conversions of Fatty Alcohols
			Ethoxylation of Fatty Alcohols to Fatty Alcohol Ethoxylates (FAE)
			Sulfation of Fatty Alcohols to Fatty Alcohol Sulfates (FAS)
				BOX: The Correct Nomenclature for SO3 Reactions
				BOX: A Typical Hair Shampoo
			Sulfation of Fatty Alcohol Ethoxylates to Fatty Alcohol Ether Sulfates (FAES)
			Fischer Reaction of Fatty Alcohols with Glucose to Alkyl Polyglucosides (APG)
			Condensation of Fatty Alcohols Using the Guerbet Reaction
		3.2.3  Conversions to Fatty Amines
		3.2.4  Other Fatty Acid Derivatives
	References
4 There is More to Oleochemistry - Reactions at the Fatty Acid Alkyl Chain
	4.1  Synthesis of Substituted Fatty Acids
	4.2  Reactions at the C=C Double Bond of Unsaturated Oleochemicals
		4.2.1  Linkage of New C–O Bonds
		4.2.2  Linkage of New C–C Bonds
			Hydroformylation and Related Reactions
			Hydrocarboxylation and Alkoxycarbonylation
			Dimerization
			Metathesis
			BOX: Can Cashew Nuts Attract Tsetse Flies?
			Chemistry of Polyunsaturated Fatty Acids
			New Oleochemical Polymers
		4.2.3  Linkage of New C-H Bonds
		4.2.4  Further Additions to the C=C Double Bonds of Oleochemicals
	References
5 The Coproduct of Oleochemistry - Glycerol
	BOX: A Brief Look at the History of Glycerol
	5.1  Properties and Use of Glycerol
	5.2  Glyceryl Esters
		BOX: The History of “Nitroglycerol”
		BOX: The Slim Japanese
		BOX: Anything Is Good, if It Is Made of Chocolate
	5.3  Glycerol Ether
		5.3.1  Glycerol Oligomers
		5.3.2  Glycerol Polymers
		5.3.3  Glycerol Alkyl Ether
		5.3.4  Glycerol Alkenyl Ether
	5.4  Glycerol Acetals and Ketals
	5.5  From Glycerol to Propanediols
	5.6  From Glycerol to Epichlorohydrin
	5.7  Glycerol Oxidation
	5.8  Dehydration of Glycerol to Acrolein
	5.9  From Glycerol to Synthesis Gas
	References
II Carbohydrates
Anchor 2
6 Sweet Chemistry - Mono- and Disaccharides
	6.1  Introduction to Carbohydrates
	BOX: The Discovery of Carbohydrates and the “Sugar Pope” Emil Fischer
	6.2  Monosaccharides
		6.2.1  Fermentative Conversions
		6.2.2  Chemical Conversions of Monosaccharides
			Dehydration Reactions
			Oxidation Reactions
			Hydrogenation Reactions
			Glycosidation Reactions
			Esterification Reactions
			Amination Reactions
	6.3  Disaccharides
		6.3.1  Sucrose Production
		6.3.2  Sucrose Processing
	6.4  Outlook on Further Oligo- and Polysaccharides
	References
7 From Wood to Pulp - Cellulose
	7.1  Occurrence and Production of Cellulose
		BOX: The Discovery of Cellulose
		BOX: Hemp - A Plant with Many Faces
	7.2  Manufacture of Paper
	7.3  Derivatization of Cellulose
		7.3.1  Regenerated Cellulose
			BOX: What Is Nanocellulose?
		7.3.2  Cellulose Esters
			BOX: The Risky Properties of Cellulose Nitrates
		7.3.3  Cellulose Ether
	References
8 Products with a Little Twist - Starch
	8.1  Structure and Occurrence
		BOX: The Small Change from α to β
		BOX: A Brief History of Starch
	8.2  Starch Production
	8.3  Use of Starch
		BOX: The Classification of Hydrolyzed Starches - The Dextrose Equivalent
	8.4  Starch Products
		8.4.1  Partially Hydrolyzed Starches
		8.4.2  Starch Saccharification Products
		8.4.3  Chemical Derivatization of Starch
			Starch Esters
			Inorganic Esters
			Organic Esters
			Starch Ether
			Oxidized Starch Products
	References
9 Carbohydrates from the Sea - Chitin, Chitosan and Algae
	9.1  Structure and Occurrence of Chitin and Chitosan
	BOX: The Difficult Discovery of Chitin
	9.2  Production of Chitin and Chitosan
	9.3  Properties and Applications of Chitin and Chitosan
		9.3.1  Properties and Applications of Chitin
		9.3.2  Properties and Applications of Chitosan
	9.4  Other Marine Polysaccharides
		9.4.1  Alginic Acid and Alginates
		9.4.2  Carrageenans
		9.4.3  Agar-Agar
	BOX: The Harvesting and Production of Algae
	References
10 Cyclic Carbohydrates - Cyclodextrins
	10.1  Chemical Structure of Cyclodextrins
	10.2  Manufacture of Cyclodextrins
	BOX: The Winding Discovery of Cyclodextrins
	10.3  Applications of Cyclodextrins
	10.4  Derivatives of Cyclodextrins
	References
III Lignin
Anchor 2
11 The “Wood-Stuff” - Lignin
	11.1  Occurrence of Lignin
	11.2  Structure of Lignin
		11.2.1  Monolignols
		11.2.2  Binding Pattern of Lignin
		11.2.3  Composition of Lignin
	11.3  Lignin Recovery
		11.3.1  Classical Wood Pulping Processes
		11.3.2  Alternative Wood Pulping Methods for Lignin Recovery
	11.4  Use of Lignin
		11.4.1  Use of Lignin as a Dispersing Agent
		11.4.2  Use of Lignin in Biomaterials
		11.4.3  Use of Lignin for the Production of Chemicals
	BOX: Whisky and Lignin
	BOX: Biosolvents from Lignin?
	References
IV Terpenoids
Anchor 2
12 The Balm of the Trees - Terpenes
	12.1  Structure and Production of Terpenes
		BOX: How Were the Complex Structures of Terpenes Identified?
	12.2  Monoterpenes
	12.3  Higher Terpene Oligomers
		BOX: A Sesquiterpene for Malaria Control
	References
13 Elastomers from Nature! - Polyterpenes
	13.1  Introduction to Polyterpenes
		BOX: Dandelion Tires
		BOX: How Was Natural Rubber Discovered?
	13.2  Production of Natural Rubber
	13.3  Properties, Processing and Use of Natural Rubber
		BOX: How Caoutchouc Did Become Rubber?
	References
V Other Natural Substances
Anchor 2
14 Building Blocks of Life - Amino Acids
	14.1  Amino Acids
		BOX: The Miller–Urey Experiment
	14.2  Peptides
	14.3  Proteins
		BOX: The Optimally Grilled Steak
		BOX: Can Milk Proteins Replace Plastic?
	References
15 Showing Your Colors Sustainably! - Natural Dyes
	15.1  Looking Back in History
		BOX: Colorful Easter Eggs in a Quite Natural Way
	15.2  Tyrian Purple
	15.3  Alizarin
	15.4  Indigo, the “King of Dyes”
		BOX: Indigo - Yesterday, Today and Tomorrow
	15.5  Other Natural Dyes
		BOX: “Holy” Yellow from India: Indian Yellow
	References
16 Nature’s Pharmacy - Natural Pharmaceuticals
	16.1  Herbal Pharmaceuticals
	16.2  Aspirin
	16.3  Caffeine
	BOX: Decaffeination: “The Impotent Coffee”
	16.4  Quinine
	BOX: Shaken or Stirred?
	16.5  Morphine
	16.6  Penicillins and Cephalosporins
	16.7  Steroids
	References
17 Vital Amines - Vitamins
	17.1  Overview of the Vitamins
	17.2  The Vitamins in Detail
		17.2.1  Vitamin A (Retinol)
		17.2.2  Vitamin B1 (Thiamine)
		17.2.3  Vitamin B2 (Riboflavin)
		17.2.4  Vitamin B3 (Niacin)
		17.2.5  Vitamin B5 (Pantothenic Acid)
		17.2.6  Vitamin B6 (Pyridoxine)
		17.2.7  Vitamin B7 (Biotin, Vitamin H)
		17.2.8  Vitamin B9 (Folic Acid)
		17.2.9  Vitamin B12 (Cobalamin)
		17.2.10  Vitamin C (Ascorbic Acid)
	BOX: A “Good Hot Lemon”
		17.2.11  Vitamin D (Calciferols)
		17.2.12  Vitamin E (Tocopherols)
		17.2.13  Vitamin K (Phylloquinone and Others)
	References
18 Enchanting Chemistry - Natural Flavors and Fragrances
	18.1  Definition and History
	BOX: The “Perfume Capital” Grasse
	BOX: Genuine Eau de Cologne
	18.2  Fragrances and Flavors in Chemical Industry
	BOX: The Taste of Vanilla
	18.3  Extraction of Essential Oils
	References
19 Plastics from Nature - Biopolymers
	19.1  Definition and Classifications
	BOX: Radiocarbon Dating
	BOX: Composting of Bioplastics
	19.2  Biopolymer Representatives
		19.2.1  Polymers from Nature
			Cellulose
			Lignin
			Starch
			Chitin and Chitosan
			Collagens
			Keratins
			Silk
			Polyhydroxyalkanoates
			Cork/Suberine
			Shellac
			Natural Rubber/Guttapercha
		19.2.2  Biopolymers from Biogenic Monomers
			Polylactic Acid
			Other Biogenic Monomers
	References
VI Biorefinery
Anchor 2
20 Refined Raw Materials! – Biorefineries
	20.1  Definition of Biorefineries
	20.2  Classification of Biorefineries
	BOX: Grass-Green Biorefinery
	20.3  Examples of Biorefineries
	BOX: Bioethanol Production in Brazil
	BOX: Biomass-to-Liquids (BtL): Bioliq®
	BOX: Europes Biorefineries
	References
Answers to the Quickies
Index