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the resulting over-fertilization, pesticide use, and land use conversion that they say would be needed to produce the additional vegetable oil Many advocates suggest that waste vegetable oil is the best source of oil to produce biodiesel However, the available supply is drastically less than the amount of petroleum-based fuel that is burned for transportation and domestic heating in the world
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952 Transesterification (Alcoholysis) Transesterification is the conversion of triacylglycerol lipids by alcohols to alkyl esters without first isolating the free fatty acids (May, 2004) Transesterification of a vegetable oil was conducted as early as 1853 many years before the first diesel engine became functional Rudolf Diesel s prime model, a single 10-ft(3-m)-iron cylinder with a flywheel at its base, ran on its own power for the first time in Augsburg, Germany, on August 10, 1893 Diesel later demonstrated his engine and received the Grand Prix (highest prize) at the World Fair in Paris, France in 1900 This engine stood as an example of Diesel s vision because it was powered by peanut oil, which is a biofuel, though not biodiesel, since it was not transesterified He believed that the utilization of biomass fuel was the real future of his engine and that the use of vegetable oils for engine fuels would become as important as petroleum and the coal-tar products of the present time The purpose of transesterification of vegetable oils to their methyl esters (biodiesel) process is to lower the viscosity of the oil The transesterification reaction is affected by alcohol type, molar ratio of glycerides to alcohol, type and amount of catalyst, reaction temperature, reaction time, and free fatty acids and water content of vegetable oils or animal fats The transesterification reaction proceeds with or without a catalyst by using primary or secondary monohydric aliphatic alcohols having one- to eight-carbon atoms as follows (Demirbas, 2006a; 2006b): Triglycerides + Monohydric alcohol Glycerin + Mono-alkyl esters Generally, the reaction temperature near the boiling point of the alcohol is recommended ( anak i and zsezen, 2005) The reactions take place at low temperatures (approximately 65 C) and at modest pressures (2 atm, 1 atm = 147 psi = 101325 kPa) Biodiesel is further purified by washing and evaporation to remove any remaining methanol The oil (87 percent), alcohol (9 percent), and catalyst (1 percent) are the inputs in the production of biodiesel (86 percent), the main output (Lucia et al, 2006) Pretreatment is not required if the reaction is carried out under high pressure (9000 kPa) and high temperature (240 C), where simultaneous esterification and transesterification take place with maximum yield obtained at temperatures ranging from 60 to 80 C at a molar ratio of 6:1 (Barnwal and Sharma, 2005) The alcohols employed in the transesterification are generally short chain alcohols such as methanol, ethanol, propanol, and butanol It was reported that when transesterification of soybean oil using methanol, ethanol, and butanol was performed, 96 to 98 percent of ester could be obtained after 1 hour (Dmytryshyn et al, 2004)
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953 Catalytic Transesterification Transesterification reactions can be catalyzed by alkalis (Fig 93) (Korytkowska et al, 2001; Dmytryshyn et al, 2004; Stavarache et al, 2005; Varghaa and Truterb, 2005; Meher et al, 2006a), acids (Lee et al, 2000; Goff et al, 2004; Lopez et al, 2005; Liu et al, 2006), or enzymes (Watanabe et al, 2000, 2002; Ghanem, 2003; Reyes-Duarte et al, 2005; Royon et al, 2007; Shah and Gupta, 2007; Bernardes et al, 2007) The catalytic transesterification
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FIGURE 93 Catalytic production of biodiesel
of vegetable oils with methanol is an important industrial method used in biodiesel synthesis Also known as methanolysis, this reaction is well studied and established using acids or alkalis, such as sulfuric acid or sodium hydroxide as catalysts However, these catalytic systems are less active or completely inactive for long chain alcohols Usually, industries use sodium or potassium hydroxide or sodium or potassium methoxide as catalyst, since they are relatively cheap and quite active for this reaction (Macedo et al, 2006) Enzymecatalyzed procedures, using lipase as catalyst, do not produce side reactions, but the lipases are very expensive for industrial scale production and a three-step process was required to achieve a 95 percent conversion The acid-catalyzed process is useful when a high amount of free acids are present in the vegetable oil, but the reaction time is very long (48 96 hours), even at the boiling point of the alcohol, and a high molar ratio of alcohol was needed (20:1 wt/wt to the oil) (Stavarache et al, 2005) The transesterification process is catalyzed by alkaline metal alkoxides, and hydroxides, as well as sodium or potassium carbonates Alkali-catalyzed transesterification with short-chain alcohols, for example, generates high yields of methyl esters in short reaction times (Jeong and Park, 1996) The alkaline catalysts show high performance for obtaining vegetable oils with high quality, but a question often arises, that is, the oils contain significant amounts of free fatty acids which cannot be converted into biodiesels but to a lot of soap (Furuta et al, 2004) These free fatty acids react with the alkaline catalyst to produce soaps that inhibit the separation of the biodiesel, glycerin, and wash water ( anakci and van Gerpen, 2003) Triglycerides are readily transesterified in a batch operation in the presence of alkaline catalyst at atmospheric pressure and at a temperature of approximately 60 to 70 C with an excess of methanol (Srivastava and Prasad, 2000) It often takes at least several hours to ensure the alkali (NaOH or KOH) catalytic transesterification reaction is complete Moreover, removal of these catalysts is technically difficult and brings extra cost to the final product (Demirbas, 2002, 2003) Nevertheless, they are a good alternative since they can give the same high conversions of vegetable oils just by increasing the catalyst concentration to 1 or 2 mole percent Alkaline metal alkoxides (as CH3ONa for the methanolysis) are the most active catalysts, since they give very high yields (>98 percent) in short reaction times (30 minutes) even if they are applied at low molar concentrations (05 mole percent) (Schuchardta et al, 1998) The transesterification process is catalyzed by sulfuric, hydrochloric, and organic sulfonic acids In general, acid-catalyzed reactions are performed at high alcohol-to-oil molar ratios, low-to-moderate temperatures and pressures, and high acid-catalyst concentrations (Lotero et al, 2006) These catalysts give very high yields in alkyl esters but these reactions are slow, requiring typically temperature above 100 C and more than 3 hours to complete the conversion (Meher et al, 2006b) Studies of the acid-catalyzed system have been very limited in number No commercial biodiesel plants to date have been reported to use the acid-catalyzed process Despite its relatively slow reaction rate, the acid-catalyzed process offers benefits with respect to its independence from free fatty acid content and the consequent
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