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The Extraction and Fractionation of Waxes from Biomass

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The Extraction and Fractionation of Waxes from Biomass The extraction and fractionation of waxes from biomass Emily H. K. Sin PhD University of York Department of Chemistry June 2012 Abstract The aim of this project was to extract and fractionate waxes from abundant and low-cost under-utilised renewable resources using a green alternative technology. Through a review of the literature, the waxes covering agricultural by-products such as straw were identified as a potential source of high value chemicals for a wide range of applications. Wheat straw waxes were extracted using organic solvents to demonstrate that straw contained high value wax compounds including free fatty acids, fatty alcohols, alkanes, wax esters, sterols, aldehydes and β-diketones. The solvent properties did not affect the composition of the extracts but changed the relative abundance of the different compounds. Linear solvation energy relationship (LSER) was used to model the extraction selectivity relating to total extraction yield and the various wax compounds. Lipophilic and aqueous fractions were separated and LSER results identified that the solvent properties affect only on the quantity of aqueous fraction recovered indicating the selectivity of the solvent. Extraction of wheat straw wax was carried out using a more environmentally friendly supercritical CO2 extraction. The compositional profiles can be tuned by the manipulation of temperature and pressure and compared with the organic solvent extractions. Optimisation of temperature and pressure was carried out and the total crude yields and wax chemical group yields were modelled using the Chrastil equation to gain a better understanding of conditions required to achieve optimum extraction. The optimisation was used as part of the industrial collaboration scale up with Sundown Products Limited and Evonik Industries where a total of three tonnes of wheat, barley and oat straws were extracted using supercritical CO2 which yielded approximately 60 kg of wax. The three cereal straws were selected based on yield and composition as raw materials for the scale up from the biomass screen of seven different straws using hexane and ethanol extractions. Economical assessment was carried out based on the scale up trial and it was concluded that currently the cereal straw wax would cost £12 per kg which is about 2 – 3 times higher than commercial waxes. The straw waxes were characterised and physical properties such as melting point were determined and found to be similar to commercial waxes such as beeswax. Fractionation by scCO2, GPC and saponification were used to further separate the 3 wax products for formulation trials and product tests with the project sponsor, Croda. The crude wax products were deeply coloured and highly hydrophobic with no emulsification properties therefore applications such as coatings and polishes were suggested. 4 Table of Contents Abtract 3 List of tables, figure and equations 9 List of abbreviations 17 Acknowledgements 21 Declaration 23 1. INTRODUCTION 27 1.1 Scope of the project 27 1.2 Sustainable development 28 1.2.1 Bio-refinery Concept 29 1.2.2 The twelve principles of Green Chemistry 31 1.2.3 Biorefinery and Green Chemistry as sustainable future 33 1.3 Agricultural waste 33 1.3.1 Availability 33 1.3.2 Straw and husk 36 1.3.3 The plant cuticle 37 1.4 Plant waxes 39 1.4.1 Classes of plant epicuticular waxes 39 1.5 Biosynthetic pathway of plant cuticular wax 42 1.5.1 Biosynthetic pathway 42 1.5.2 Cereal waxes 49 1.6 Commercial waxes 52 1.6.1 Manufacturing of commercial waxes 52 1.6.2 Chemical composition and physical properties 56 1.6.3 Wax market and applications 57 1.6.4 Wax market outlook and opportunities 58 1.7 Introduction to work in thesis 60 2. SOLVENT EXTRACTION OF WHEAT STRAW WAX 65 2.1 Introduction 65 2.2 Solvent selection and extraction 65 2.2.1 Solvent parameters and linear solvation energy relationships 65 2.2.2 Solvent green guides 67 2.2.3 Biomass pre-treatment techniques 69 2.2.4 Solvent extraction techniques 70 2.3 Optimisation of solvent extraction using LSER 72 2.4 Chemical composition identification using GC and GC-MS 84 5 2.4.1 Free fatty acids 87 2.4.2 Hydrocarbons 91 2.4.3 Free fatty alcohols 94 2.4.4 Aldehydes 96 2.4.5 Wax Esters 99 2.4.6 Sterols 104 2.4.7 Beta-diketones 113 2.4.8 Chemical composition of wheat straw wax summary 117 2.5 Quantification of key wax components in wheat straw wax 117 2.5.1 Quantification of key wax components by calibration 119 2.5.2 Free fatty acids 121 2.5.3 Hydrocarbons 123 2.5.4 Free fatty alcohols 125 2.5.5 Aldehydes 126 2.5.6 Wax esters 127 2.5.7 Sterols 130 2.5.8 β-Diketones 132 2.5.9 Summary of wax components quantified in organic solvent extracts 2.6 Conclusion and future work 141 3. SUPERCRITICAL CARBON DIOXIDE EXTRACTION OF WHEAT STRAW WAX 141 3.1 Introduction 141 3.2 Carbon dioxide extraction of wheat straw 151 3.2.1 Raw materials, pre-treatment and moisture content 151 3.2.2 Comparison of organic solvents and carbon dioxide extraction yields 152 3.2.3 Effect of temperature and pressure in supercritical carbon dioxide crude extraction yields by first order polynomial modelling 154 3.2.4 Effect of temperature and pressure in supercritical carbon dioxide extraction yields of different wax groups 159 3.2.5 Optimisation of wheat straw wax extraction using supercritical carbon dioxide by Chrastil modelling 164 3.3 Identification and quantification of key wax components in wheat straw wax 171 3.3.1 Free fatty acids 172 3.3.2 Hydrocarbons 175 3.3.3 Fatty alcohols 177 3.3.4 Aldehydes 178 3.3.5 Wax esters 179 3.3.6 Sterols 180 3.3.7 β-Diketones 182 3.3.8 Summary of wax components quantified in CO2 extracts 183 3.4 Conclusion and future work 189 6 4. STRAW WAX SCREEN AND PRODUCTION SCALE SUPERCRITICAL CARBON DIOXIDE EXTRACTION OF CEREAL STRAW WAXES 196 4.1 Introduction 196 4.2 Raw materials selection 196 4.2.1 Raw materials 196 4.2.2 Identification of hexane and ethanol extraction of raw materials 197 4.2.3 Quantification of hexane and ethanol extraction of raw materials 213 4.3 Production scale extraction of cereal straw wax 226 4.3.1 Raw materials 226 4.3.2 Laboratory extraction trials at York Green Chemistry Centre 227 4.3.3 Production scale extraction trials at Evonik Industries 229 4.4 Conclusion and future work 241 5. STRAW WAX PROCESSING, PHYSICAL PROPERTIES AND ECONOMIC CONSIDERATIONS 245 5.1 Introduction 245 5.2 Straw wax processing 245 5.2.1 Co-extraction of water 245 5.2.2 Fractionation by supercritical carbon dioxide 248 5.2.3 Fractionation by gel permeation chromatography (GPC) 253 5.2.4 Saponification 263 5.3 Physical properties 271 5.3.1 Melting point 271 5.3.2 Acid value, saponification value and drop point 281 5.3.3 Appearance and aroma 284 5.3.4 Water absorption 286 5.4 Applications and costs 287 5.4.1 Potential applications 287 5.4.2 Economic considerations 288 5.5 Conclusion and future work 293 6. EXPERIMENTAL PROCEDURES 299 6.1 Materials and reagents 299 6.2 Pre-treatment, extraction and fractionation procedures 300 6.2.1 Moisture content of raw materials 300 6.2.2 Pre-treatment of raw materials 300 6.2.3 Soxhlet extraction 301 6.2.4 FexIKA® extraction 301 6.2.5 Supercritical fluid extraction 302 6.2.6 Purification and fractionation of wax extracts 304 6.2.7 Saponification 305 7 6.3 Chemical compositions analysis procedures 306 6.3.1 GC analysis 306 6.3.2 GC-MS analysis 307 6.3.3 Derivatisation for GC analysis 307 6.3.4 FAME analysis 307 6.3.5 IR analysis 308 6.3.6 GPC analysis 308 6.3.7 MALDI TOF MS analysis and synthesis of LiDHB matrix 309 6.4 Physical properties of wax extracts 310 6.4.1 Decomposition by STA analysis 310 6.4.2 Thermal transition temperatures by DSC analysis 310 6.4.3 Acid value 310 6.4.4 Saponification value 311 6.4.5 Drop point 312 6.4.6 Slip point 312 6.4.7 Gardner colour 312 6.4.8 Water absorption 313 6.4.9 Base value 313 7. CONCLUSION AND FUTURE WORK 317 8. REFERENCES 325 8 List of tables, figures and equations 1. INTRODUCTION Figure 1.1: Comparison of oil-refinery vs. bio-refinery (originally in colour) 30 Figure 1.2: Straw bio-refinery (originally in colour) 31 Figure 1.3: The “Twelve Principles of Green Chemistry” (originally in colour) 32 Figure 1.4: Total breakdown of cereal and oilseed crops in UK in 2007 (originally in colour) 34 Figure 1.5: Breakdown of wheat, barley, oat and oilseed rape straw in the UK in 2007 (originally in colour) 35 Figure 1.6: Cereal straw and its botanical components (originally in colour) 36 Figure 1.7: The structure of the plant cuticle (originally in colour) 38 Figure 1.8: Molecular structure of cuticular waxes 39 Table 1.1: Common wax classes 41 Figure 1.9: Fatty acids de novo synthetic pathway 44 Figure 1.10: Wax biosynthesis including acyl reduction, fatty acids elongation and alkane pathways 46 Figure 1.11: Beta-diketone biosynthetic pathway 47 Figure 1.12: A simplified sterol biosynthetic pathway from the isoprenoid pathway 48 Table 1.2: Epicuticular wax of cereal plants 49 Table 1.3: Epicuticular wax from cereal waste 51 Figure 1.13: Wool grease retrieval from sheep wool 54 Figure 1.14: Wool grease processing at Croda 55 Table 1.4: Chemical composition and physical properties of four commercial waxes 57 Figure 1.15: Global wax applications 58 Figure 1.16: Wax market outlook in 2020 59 Figure 1.17: A poster by B&T Company at In-Cosmetics® 2010 (Picture taken at the exhibition) (originally in colour) 60 2.
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