Lipase‐catalyzed transesterification of rapeseed oil and 2‐ethyl‐1‐hexanol

Linko, Yu‐Yen; Lämsä, Merja; Huhtala, Anne; Linko, P.

doi:10.1007/bf02541364

Cited by 65 publications

(22 citation statements)

References 27 publications

(12 reference statements)

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“…Several studies report alcoholyses of vegetable oils and animal fats with primary and secondary alcohols and straightand branched-chain alcohols using lipases as catalysts (3)(4)(5)(6). However, these reports do not contain the continuous methanolysis of oils and fats in an organic solvent-free environment.…”

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confidence: 99%

Conversion of vegetable oil to biodiesel using immobilized Candida antarctica lipase

Shimada

Watanabe

Samukawa

et al. 1999

J Americ Oil Chem Soc

556

270

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Biodiesel derived from vegetable oils has drawn considerable attention with increasing environmental consciousness. We attempted continuous methanolysis of vegetable oil by an enzymatic process. Immobilized Candida antarctica lipase was found to be the most effective for the methanolysis among lipases tested. The enzyme was inactivated by shaking in a mixture containing more than 1.5 molar equivalents of methanol against the oil. To fully convert the oil to its corresponding methyl esters, at least 3 molar equivalents of methanol are needed. Thus, the reaction was conducted by adding methanol stepwise to avoid lipase inactivation. The first step of the reaction was conducted at 30°C for 10 h in a mixture of oil/methanol (1:1, mol/mol) and 4% immobilized lipase with shaking at 130 oscillations/min. After more than 95% methanol was consumed in ester formation, a second molar equivalent of methanol was added and the reaction continued for 14 h. The third molar equivalent of methanol was finally added and the reaction continued for 24 h (total reaction time, 48 h). This three-step process converted 98.4% of the oil to its corresponding methyl esters. To investigate the stability of the lipase, the three-step methanolysis process was repeated by transferring the immobilized lipase to a fresh substrate mixture. As a result, more than 95% of the ester conversion was maintained even after 50 cycles of the reaction (100 d).Paper no. J9045 in JAOCS 76, 789-793 (July 1999). KEY WORDS:Biodiesel, Candida antarctica lipase, immobilized enzyme, methanolysis, vegetable oil.Biodiesel (fatty acid methyl esters) is produced by alcoholysis of vegetable oils and animal fats. The main advantages of biodiesel are its biodegradability, renewability, and improved exhaust emissions. Because of these environmental advantages, biodiesel has drawn considerable attention. Currently, biodiesel is produced from vegetable oils in Europe and North America (1,2), and from waste edible oil in Japan. At present, chemical methods are used for biodiesel production, but these methods have drawbacks, such as, difficulties in the recovery of glycerol, the need for removal of catalyst, and the energyintensive nature of the processes. Furthermore, oils containing free fatty acids and/or water are incompletely transesterified using chemical methods. A biochemical approach can overcome these problems, but has not been adopted industrially because of the high cost of the enzyme catalyst. The establishment of a continuous production process using an immobilized enzyme is strongly needed to decrease the production cost of biodiesel using this approach. Several studies report alcoholyses of vegetable oils and animal fats with primary and secondary alcohols and straightand branched-chain alcohols using lipases as catalysts (3-6). However, these reports do not contain the continuous methanolysis of oils and fats in an organic solvent-free environment. A continuous reaction system without organic solvent is necessary for the industrial production of biodiesel. Our ...

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mentioning

confidence: 99%

Conversion of vegetable oil to biodiesel using immobilized Candida antarctica lipase

Shimada

Watanabe

Samukawa

et al. 1999

J Americ Oil Chem Soc

556

270

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“…Recently, research has centered on the use of lipases to transesterify higher-molecular weight fatty acids to alkyl esters. Lipase-catalyzed alcoholyses of sunflower oil (7), rapeseed oil (8), soybean oil, and beef tallow (9) have been reported. The alcoholysis reactions generally involve primary alcohols with a few scattered reports on transesterifications with secondary alcohols (10).…”

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Lipase‐catalyzed production of biodiesel

Nelson

Foglia

Marmer

1996

J Americ Oil Chem Soc

480

225

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ABSTRACT:Lipases were screened for their ability to transesterify triglycerides with short-chain alcohols to alkyl esters. The lipase from Mucor miehei was most efficient for converting triglycerides to their alkyl esters with primary alcohols, whereas the lipase from Candida antarctica was most efficient for transesterffying triglycerides with secondary alcohols to give branched a|kyl esters. Conditions were established for converting tallow to short-chain alkyl esters at more than 90% conversion. These same conditions also proved effective for transesterifying vegetable oils and high fatty acid-containing feedstocks to their respective alkyl ester derivatives.

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“…The importance of controlling the water content in lipase-catalysed hexanol esterification has been emphasised in the literature. 6 In this study the reaction was achieved by direct esterification in which butyric acid, not tributyrin, was employed as acyl donor. The esterification water from direct esterification may accumulate during the reaction, so that the molar conversion is decreased.…”

Section: Results and Discussion Effect Of Solvent And Added Watermentioning

confidence: 99%

Lipase‐catalysed biosynthesis of hexyl butyrate by direct esterification: optimisation by response surface methodology

et al. 2003

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The ability of immobilised lipase from Rhizomucor miehei (Lipozyme IM-77) to catalyse the direct esterification of hexanol and butyric acid was investigated. Response surface methodology (RSM) and a four-factor/five-level central composite rotatable design (CCRD) were employed to evaluate the effects of synthesis parameters such as reaction time (2-10 h), temperature (25-65 • C), substrate molar ratio of hexanol to butyric acid (1:1-3:1) and enzyme amount (10-50%; 0.24-1.18 BAUN) on the percentage molar conversion of hexyl butyrate by direct esterification. All the parameters had significant effects on the percentage molar conversion. Based on ridge maximum analysis, the optimal conditions for synthesis were: reaction time 8.0 h, temperature 46.9 • C, substrate molar ratio 1:1.2 and enzyme amount 36.4% (0.87 BAUN). The predicted value was 100% and the actual experimental value 98.2% molar conversion. INTRODUCTIONHexyl esters with green note flavour, eg hexyl butyrate, are extremely aromatic compounds and widely used in the food industry. 1 Customarily, they are produced by chemical synthesis or extracted from natural sources. However, the biosynthesis of such esters by lipasecatalysed chemical reactions under mild conditions has been receiving much attention for producing these valuable products. An optimised enzymatic reaction of hexyl ester synthesis improves the yield conversion and reduces the cost of production for the manufacturers.Carvalho et al 2 reported that hexyl acetate was synthesised by the cutinase-catalysed transesterification reaction of butyl acetate with hexanol in a reversed micelle system. Bourg-Garros et al 3 synthesised (Z)-3-hexen-1-yl butyrate in high yield by direct esterification using Mucor miehei (Lipozyme IM) and Candida antarctica (Novozym 435) lipases in hexane and in a solvent-free system.The present work focuses on the parameters that affect Rhizomucor miehei (Lipozyme IM-77) lipase catalysis of the direct esterification of hexyl butyrate using butyric acid as acyl donor in n-hexane. Our purpose was to better understand relationships between the factors (reaction time, temperature, enzyme amount and substrate molar ratio) and

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Lipase‐catalyzed transesterification of rapeseed oil and 2‐ethyl‐1‐hexanol

Cited by 65 publications

References 27 publications

Conversion of vegetable oil to biodiesel using immobilized Candida antarctica lipase

Conversion of vegetable oil to biodiesel using immobilized Candida antarctica lipase

Lipase‐catalyzed production of biodiesel

Lipase‐catalysed biosynthesis of hexyl butyrate by direct esterification: optimisation by response surface methodology

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