Biofuels in Perspective

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Triglyceride Methanol E 3 E 3 E 3 E 1 E 1 E1 E 2 E 3 E 2 E 3 E 2 E 3 E 3 E 3 Enzymatic Production of Biodiesel 131 Methyl esters Glycerol Figure 8.2 Three types of lipase for methanolysis reaction. E1: Extracellular lipase; E2: Intracellular lipase; E3: Cell-surface-displayed lipase. Figure 8.1b. 19 The first step is the conversion of triglycerides to diglycerides, which is followed by the conversion of diglycerides to monoglycerides and of monoglycerides to glycerol, yielding one fatty acid ester molecule from each glyceride at each step. 20,21 The kinetics of triglyceride transesterification with methanol, i.e. methanolysis, catalyzed by Rhizopus oryzae lipase appears to follow a sequential reaction mechanism. 22 That is, triglycerides and partial glycerides are first hydrolyzed by lipase to partial glycerides and free fatty acids, respectively, after which methyl esters (MEs) are synthesized from free fatty acids and methanol (see Figure 8.1(b)). This suggests that, unlike in the case of alkali-catalyzed methanolysis, free fatty acids contained in used oils can be easily converted to MEs. Three types of lipase, i.e. the extracellular, intracellular, and cell-surface-displayed lipases shown in Figure 8.2, can be utilized for methanolysis reaction. Since they can be prepared by different methods and also utilized in different forms, each reveals a range of characteristics in methanolysis reaction. 8.3 Use of Extracellular Lipases Methanolysis reaction can be carried out using many kinds of extracellular lipase from different microorganisms. It is notable that both non-regiospecific and 1(3)-regiospecific lipases are utilized in methanolysis reaction and also that acyl migration in triglycerides is significant in the use of 1(3)-regiospecific lipase as it gives a higher conversion rate. The present section includes description of transesterification reactions using various types of extracellular lipase and a description of the effect of acyl migration on ME conversion with 1(3)-regiospecific lipase. 8.3.1 Transesterification with Various Types of Alcohol As shown in Table 8.1 various types of alcohol – primary, secondary, and straight- and branched-chain – can be employed in transesterification using lipases as catalysts. 19 Linko
132 Biofuels Table 8.1 Enzymatic transesterification reaction using various types of alcohol and lipase Oil Alcohol Lipase Conversion (%) Solvent Ref. Rapeseed 2-ethyl-1-hexanol C. RUGOSA 97 None 23 Mowrah, Mango, Kernel, Sal C4–C18:1 alcohols M. MIEHEI (LIPOZYME IM-20) Sunflower Ethanol M. MIEHEI (LYPOZYME) 86.8–99.2 None 24 83 None 25 Fish Ethanol C. ANTARCTICA 100 None 26 Recycled restaurant grease Tallow, Soybean, Rapeseed Ethanol P. CEPACIA (LIPASE PS-30) + C. ANTARCTICA (LIPASE SP435) 85.4 None 27 Primary alcoholsa M. MIEHEI (LIPOZYME IM60) 94.8–98.5 Hexane 28 Secondary alcoholsb C. antarctica (SP435) 61.2–83.8 Hexane M. MIEHEI 19.4 None Methanol (LIPOZYME IM60) Ethanol M. miehei (Lipozyme IM60) 65.5 None Sunflower Methanol P. FLUORESCENS 3 None 29 Methanol Ethanol Palm kernel Methanol Ethanol a Methanol, ethanol, propanol, butanol, and isobutanol. bIsopropanol and 2-butanol. P. CEPACIA (LIPASE PS-30) 79 82 Petroleum ether None 15 None 30 72 None et al. 23 have demonstrated the production of a variety of biodegradable esters and polyesters with lipase as the biocatalyst. In the transesterification of rapeseed oil with 2-ethyl-1hexanol, 97 % conversion of esters was obtained using Candida rugosa lipase powder. De et al. 24 investigated the conversion of fatty alcohol esters (C4–C18:1) using immobilized Mucor miehei lipase (Lipozyme IM-20) in a solvent-free system. The percentage rate of molar conversion of all corresponding alcohol esters ranged from 86.8 to 99.2 %, while the slip melting points of the esters were found to increase steadily with increasing alcohol chain length (from C4 to C18) and to decline with the incorporation of unsaturation for the same chain length (as from C18 to C18:1). Transesterification of sunflower oil, fish oil, and grease with ethanol, i.e. ethanolysis, has also been studied. In each case, high yields of beyond 80 % were achieved using lipases from M. miehei, 25 C. Antarctica, 26 and Pseudomonas cepacia. 27 Nelson et al. 28 investigated the ability of lipases in transesterification with short-chain alcohols to give alkyl esters. The lipase from M. miehei was the most efficient for converting triglycerides to their alkyl esters with primary alcohols, whereas that from C. antarctica
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Biofuels Biofuels. Edited by Wim So
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Biofuels Edited by WIM SOETAERT Ghe
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Contents Series Preface ix Preface
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Contents vii 6.3 Biomass Gasificati
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Series Preface Renewable resources,
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Preface This volume on Biofuels fit
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Editors List of Contributors Wim So
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1 Biofuels in Perspective W. Soetae
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Table 1.1 Approximate average world
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Table 1.3 Energy yields of bio-ener
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Biofuels in Perspective 7 is burnt
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2 Sustainable Production of Cellulo
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Sustainable Production of Cellulosi
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Figure 2.9 2004 US adoption rates o
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3 Bio-Ethanol Development in the US
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Bio-Ethanol Development in the USA
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Biorefineries in Production (115) B
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Cost of Cellulosic Ethanol, $ per g
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4 Bio-Ethanol Development(s) in Bra
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Bio-Ethanol Development(s) in Brazi
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Share of energy consumption 100% 90
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Table 4.2 Main technological improv
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4.7.4 Use of Fertilizers and Pestic
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78 Biofuels Table 5.1 Biodiesel pro
Page 95 and 96: 80 Biofuels CH 2 O CH O COR R1 + 3
Page 97 and 98: 82 Biofuels short reaction times. 9
Page 99 and 100: 84 Biofuels Table 5.4 Overview on h
Page 101 and 102: 86 Biofuels Table 5.5 Critical cond
Page 103 and 104: 88 Biofuels methoxide as catalyst u
Page 105 and 106: 90 Biofuels KOH Methano Oil/Fat Aci
Page 107 and 108: 92 Biofuels 16. J. Graille, P. Loza
Page 110 and 111: 6 Bio-based Fischer-Tropsch Diesel
Page 112 and 113: 6.2.1.2 Catalysts Bio-based Fischer
Page 114 and 115: Bio-based Fischer-Tropsch Diesel Pr
Page 132 and 133: 7 Plant Oil Biofuel: Rationale, Pro
Page 134 and 135: Table 7.1 Market milestones for pla
Page 136 and 137: Water CO 2 Figure 7.1 Closed CO 2 l
Page 138 and 139: Plant Oil Biofuel: Rationale, Produ
Page 140 and 141: Plant Oil Biofuel: Rationale, Produ
Page 142: Plant Oil Biofuel: Rationale, Produ
Page 145: 130 Biofuels Among the attractive f
Page 149 and 150: 134 Biofuels conversion was maintai
Page 151 and 152: 136 Biofuels (diglycerides) decreas
Page 153 and 154: 138 Biofuels ME content (wt.%) Reac
Page 155 and 156: 140 Biofuels Ratio of initial react
Page 157 and 158: 142 Biofuels (a) 34 kDa 31 kDa 34 k
Page 159 and 160: 144 Biofuels preparation of whole-c
Page 161 and 162: ability to reduce flocculation (% o
Page 163 and 164: 148 Biofuels 5. R. C. Strayer, J. A
Page 165 and 166: 150 Biofuels 46. H. Fukuda, Immobil
Page 168 and 169: 9 Production of Biodiesel from Wast
Page 170 and 171: Production of Biodiesel from Waste
Page 174 and 175: 9.3.2 Processing of Crude and Waste
Page 176 and 177: Heavy layer from alkaline neutralis
Page 182 and 183: CPO I 1 1 Heating 60°C Reaction st
Page 184 and 185: References Production of Biodiesel
Page 186 and 187: 10 Biomass Digestion to Methane in
Page 188 and 189: Cow manure Pig manure Yard manure B
Page 190 and 191: Number of plants 3000 2500 2000 150
Page 192 and 193: Biomass Digestion to Methane in Agr
Page 194 and 195: Biomass Digestion to Methane in Agr
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Table 10.4 Alternative forms of ene
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Biomass Digestion to Methane in Agr
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Wet fermentation 3 - 10% TS applica
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Rel. Frequency [%] 35 30 25 20 15 1
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Steam 2 1 Energy crops (& manure) D
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198 Biofuels 11.1 Introduction Hydr
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200 Biofuels lactate 6 glucose 1 GA
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Table 11.2 Continued Organism Domai
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204 Biofuels NADH is that the react
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206 Biofuels Clostridium thermocell
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208 Biofuels in particular in Cl. p
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210 Biofuels ferredoxin-dependent m
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212 Biofuels Concentration (mM) 45
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214 Biofuels genes of the glycolysi
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216 Biofuels 11. S. Tanisho and Y.
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218 Biofuels 49. M. J. Axley, D. A.
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220 Biofuels 83. P. J. Silva, E. C.
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12 Improving Sustainability of the
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Table 12.1 Corn ethanol dry mill: e
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Table 12.2 Atmospheric CO2 (equival
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Table 12.3 Incremental CO2 equivale
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Improving Sustainability of the Cor
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Improving Sustainability of the Cor
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Index italic entries indicate refer
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iorefineries 3, 10, 11, 41 and corn
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policy (official) 59-61 production
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NADH 200-6, 207, 210 natural gas 1
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