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Fatty Alcohols

Fatty Alcohols

Stephen M Mudge | Scott E Belanger | Paul C DeLeo

(2018)

Additional Information

Abstract

Fatty alcohols are mainly used in the production of detergents and surfactants. They are also components of cosmetics, foods and as industrial solvents.

The 2008 edition originated from a multi-year review of the occurrence, behaviour and use of fatty alcohols to inform the registration of such chemicals through the REACH process in the EU. This review highlighted areas requiring further research. In this expanded edition, new information regarding products containing fatty alcohol derivatives, the fate of these down-the-drain products in wastewater systems and the use of compound specific stable isotope methods has been published. This work has been amalgamated with a number of aspects relating to the inclusion of these compounds in the EU bio-based economy drive.

Significant advances have been made since the first edition. No other book brings together all the disparate information regarding this group of chemicals that are of great interest to environmental scientist (as biomarkers), industry (as surfactants) and to regulators.


Table of Contents

Section Title Page Action Price
Cover Cover
Fatty Alcohols: Anthropogenic and Natural Occurrence in the Environment i
Preface v
Acknowledgements ix
About the Authors xi
Contents xiii
Chapter 1 - Definitions 1
1.1 Names and Structures 1
1.2 Physicochemical Properties 3
1.2.1 Solubility Versus Chain Length 3
1.2.2 Partitioning (Kow) and Sediment Associations 5
1.3 Summary 8
References 8
Chapter 2 - Biological Synthesis 11
2.1 Type I Fatty Acid Synthesis 11
2.1.1 Unsaturated Chains 13
2.2 Type II Fatty Acid Synthesis 14
2.2.1 Unsaturated Compounds 14
2.2.2 Branched Chains 16
2.3 Fatty Acid Degradation 17
2.4 Fatty Acyl-CoA Reductase (FAR) 18
2.5 Synthesis from Carbohydrates (Copepods) 20
2.6 Summary 21
References 21
Chapter 3 - Occurrence in Biota 24
3.1 Bacteria 25
3.2 Chlorophyll Side Chain (Phytol) 26
3.3 Marine Plants 27
3.4 Terrestrial Plant Waxes 28
3.5 Mosses and Other Peat Forming Plants 30
3.6 Marine Animals 31
3.7 Insects 33
3.8 Birds 34
3.9 Summary 35
References 35
Chapter 4 - Consumer and Cosmetic Product Uses and Production 40
4.1 Detergent Alcohols Manufacture 40
4.1.1 Oleochemical Based Alcohols 41
4.1.1.1 Fatty Acids 41
4.1.1.2 Fatty Acid Methyl Esters (FAMEs) 41
4.1.2 Oleochemical Fatty Alcohols 41
4.2 Petrochemical Based Alcohols 45
4.2.1 Normal Paraffin 45
4.2.2 Internal Olefins 45
4.2.3 Conventional OXO Alcohols Based on Internal Olefins 45
4.3 Alcohols Based on Ethylene 46
4.3.1 Ziegler Ethylene Growth Process 46
4.3.2 Ziegler Alcohols 47
4.4 Modified OXO Alcohols 47
4.4.1 SHOP (Shell Higher Olefin Process) α-Olefins 47
4.4.2 SHOP Internal Olefins and Modified OXO Alcohols 48
4.4.3 OXO Alcohols Derived from Fischer–Tropsch α-olefins 49
4.5 Summary of Production Methods 49
4.6 Detergent Formulations 50
4.7 Global Production 56
4.7.1 Asia 56
4.7.2 China 58
4.7.3 Japan 58
4.7.4 Southeast Asia 60
4.7.5 Western Europe 60
4.7.6 North America 62
4.8 Usage of Fatty Alcohol-based Consumer Products 64
4.8.1 Contributions to the WWTP Influent 69
4.9 Summary 72
References 72
Chapter 5 - Environmental Transformations 75
5.1 Metabolism of Fatty Alcohols 76
5.2 Natural Degradation 78
5.2.1 Short Chain Moieties 79
5.2.2 Long Chain Moieties 81
5.3 Degradation Rate Constants 83
5.3.1 Phytol Degradation 84
5.4 Branched Chains 85
5.5 Wastewater Treatment Plants (WWTPs) 85
5.6 Effect of Chemical Associations on Transformation Rates 87
5.6.1 “Natural” Fatty Alcohols in WWTPs 87
5.6.2 Anthropogenic Fatty Alcohols in Synthetic WWTPs 88
5.6.3 Faecal Fatty Alcohols 90
5.7 What We Still Don't Know 90
5.8 Summary 91
References 91
Chapter 6 - Analytical Methods 94
6.1 Overview of Methods 94
6.2 Methods for Analysis of Free Fatty Alcohols (and Ethoxylates) 94
6.3 Environmental Samples 96
6.4 Inter-laboratory Comparisons 98
6.5 Stable Isotope Analysis 99
6.6 Summary 102
References 102
Chapter 7 - Environmental Concentrations 104
7.1 The Marine Environment 107
A. Victoria Harbour, BC – Estuarine Surface Sediments 107
B1. Concepcíon Bay, Chile and B2. San Vicente Bay, Chile 109
C. Rio De Janeiro – Surface Sediments in a Contaminated Bay 111
D1. Ria Formosa Lagoon – Surface Sediments 112
D2. Ria Formosa Lagoon – Suspended and Settled Sediments 114
D3. Ria Formosa Lagoon – Shallow Core from Intertidal Sediments 116
E. Eastern North Atlantic 118
F. San Miguel Gap, California – Long Marine Core 118
G. Rio Grande Rise (516F of Leg 72 ODP), Brazil 120
H. Falkland Plateau (511 of Leg 71 ODP), S. Atlantic 121
I. Guatemalan Basin (Legs 66 & 67 ODP), Central America 121
J1. Continental Slope, SW of Taiwan 122
J2. East China Sea, N of Taiwan 122
7.2 The Terrestrial Environment 124
K. Pasture Land, Southern Australia 124
L. Prairie Zone Soils, Alberta, Canada 125
M. Luray River Catchment, Virginia 125
N. Ohio, Oklahoma and Oregon, USA 131
7.3 UK Studies 136
1. Conwy Estuary – Estuarine Core (50 cm) 137
2. Mawddach Estuary – Surface Sediments 139
3. The Menai Strait – Surface Sediments 141
4. Loch Riddon, Scotland – Mid-length Marine Core 143
5. Clyde Sea, Scotland – Surface Sediments 143
6. Loe Pool, Cornwall – Coastal Lake 145
7. Bolton Fell Moss, Cumbria–Mire 146
8. Lochnagar, Scotland – Mountain Lake 146
9a. Loch Eil, Scotland – a Marine Core and 9b. Loch Lochy, Scotland – a Freshwater Core 147
7.4 Summary of Concentrations 149
7.5 Summary 149
References 150
Chapter 8 - Using Fatty Alcohols as Biomarkers 154
8.1 Profiles 154
8.2 Stable Isotopes 155
8.2.1 13C Composition 155
8.2.2 2H Composition 155
8.3 Bacterial Biomass 156
8.4 Marine Fauna and Unicellular Algae 157
8.5 Terrestrial Plants 158
8.6 Photosynthetic Activity 159
8.7 Summary 160
References 160
Chapter 9 - Multivariate Statistics 162
9.1 Chemometric Methods of Use with Fatty Alcohols 162
9.1.1 Principal Components Analysis (PCA) 163
9.1.2 Partial Least Squares (PLS) 169
9.1.3 Polytopic Vector Analysis (PVA) 173
9.2 Summary 176
References 176
Chapter 10 - Environmental and Human Safety Aspects of Fatty Alcohols 178
10.1 Physical Chemistry Relevant to Safety Assessments 178
10.1.1 OECD SIAR Summary 178
10.1.2 Physicochemical Overview from the OECD SIAR 180
10.1.3 Conclusions for Characterising the OECD Long Chain Alcohols Category 180
10.2 Human Health and Risk 180
10.2.1 Uses and Products 180
10.2.2 Hazards for Human Health 183
10.2.3 Exposure Characterisation for Human Health 184
10.2.4 Risk Characterisation for Human Health 185
10.3 Environmental Risk 186
10.3.1 Pathways of Environmental Exposure 186
10.3.2 Environmental Effects 188
10.4 Measurements of Exposure for the Purpose of Environmental Risk Assessment 192
10.5 Risk Characterisation in the Environment 192
10.6 Summary 194
References 194
Subject Index 197