Synthesis of Oleyl Oleate with Immobilized Lipase from <i>Mucor miehei</i>

Krmelj, V.; Habulin, Maja; Knez, Željko

doi:10.1002/lipi.19950970903

Cited by 2 publications

(4 citation statements)

References 5 publications

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“…The relatively high activation energy indicates that the reaction is not controlled exclusively by internal diusion within the enzyme beads (Levenspiel, 1999). The apparent activation energy for the reaction is of the same order that has been reported for other esteri®cation reactions (Jenta et al, 1997;Kee et al, 1999;Krmelj et al, 1995;Pecnik and Knez, 1992).…”

Section: Activation Energymentioning

confidence: 55%

Lipase‐catalyzed synthesis of geranyl acetate in n‐hexane with membrane‐mediated water removal

Bartling

Thompson

Pfromm

et al. 2001

Biotech & Bioengineering

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The esterification of geraniol with acetic acid in n-hexane was investigated. A commercial lipase preparation from Candida antarctica was used as catalyst. The equilibrium conversion (no water removal) was found to be 94% for the reaction of 0.1 M alcohol and 0.1 M acid in n-hexane at 30 degrees C. This was shown by both hydrolysis and esterification reactions. The activation energy of reaction over the temperature range 10 degrees to 50 degrees C was found to be 16 kJ/mol. The standard heat of reaction was -28 kJ/mol. Membrane pervaporation using a cellulose acetate/ceramic composite membrane was then employed for selective removal of water from the reaction mixture. The membrane was highly effective at removing water while retaining all reaction components. Negligible transport of the solvent n-hexane was observed. Water removal by pervaporation increased the reaction rate by approximately 150% and increased steady-state conversion to 100%.

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Section: Activation Energymentioning

confidence: 55%

Lipase‐catalyzed synthesis of geranyl acetate in n‐hexane with membrane‐mediated water removal

Bartling

Thompson

Pfromm

et al. 2001

Biotech & Bioengineering

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“…1B). As already noted, the rate of esterification was related to the amount of enzyme involved (9,12,19,(21)(22)(23). In our hands, the minimum concentration of Lipozym IM necessary to achieve maximum conversion yield (92% in 15 h) was 4% (w/w reactants).…”

Section: Resultsmentioning

confidence: 80%

“…Hence, the biological production of such esters is of much current commercial interest. In this context, the use of immobilized lipases working in nonaqueous media (3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14) has potential since esters produced from natural acids and alcohols may be considered as natural. This mode of production is of great interest, as it would make food industry less dependent on seasonal, climatic, and geographical variations.…”

mentioning

confidence: 99%

“…For safety, economic, technological and environmental reasons, enzyme-mediated direct esterification in a solventfree medium is of utmost importance especially in the food industry. In the last 6 yr, lipase-mediated direct esterification and transesterification have motivated research on M. miehei (9,23,25,31), C. cylindraceae (11,25), and C. antarctica (13,14,32,33) lipases. For instance, lipase from C. antarctica was reported (32) to mediate the transesterification synthesis of geranyl and β-citronellyl acetate in 94% yield (in 10 h) compared to 74% (in 6 h) for the direct esterification of β-citronellol by acetic acid (13).…”

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confidence: 99%

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Synthesis of (Z)‐3‐hexen‐1‐yl butyrate in hexane and solvent‐free medium using Mucor miehei and Candida antarctica lipases

Bourg-Garros¹,

Razafindramboa²,

Pavia

1997

J Americ Oil Chem Soc

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Z)-3-Hexen-1-yl butyrate is an important flavor and fragrance compound as it represents the model of a natural herbaceous (green) note. Two immobilized lipases from Mucor miehei (Lipozym IM) and from Candida antarctica (Novozym 435) were investigated for their use in the synthesis of (Z)-3-hexen-1-yl butyrate by direct esterification in n-hexane. To determine optimal conditions for esterification, we examined the following parameters: temperature, amount of lipase, acid/alcohol ratio, and absence of solvent. In n-hexane, bioconversion yields reached 95 (after 4 h) and 92% (after 6 h) for, respectively, Lipozym IM [17 (w/w reactants)] and Novozym 435 [2% (w/w reactants)]. In the absence of solvent, at 60°C, Novozym 435-catalyzed esterification afforded the title compound in 80% yield. Up to 250 g (in hexane) and 160 g (without solvent) of ester were easily prepared, in a single operation, at a laboratory scale, in few hours, using 2% (w/w reactants) lipase.Low-molecular-weight esters derived from short-chain carboxylic acids (acetates, propionates, butyrates, …) represent an important class of flavoring materials. They are responsible for the fruity odors of many foods and fragrances (1,2). In foodstuff industries, flavor and fragrance loss due to various reasons including manufacturing processes must be compensated for by the addition of aromas. Moreover, there is a growing demand for natural flavors containing green notes represented by C-6 alcohols derivatives. Hence, the biological production of such esters is of much current commercial interest. In this context, the use of immobilized lipases working in nonaqueous media (3-14) has potential since esters produced from natural acids and alcohols may be considered as natural. This mode of production is of great interest, as it would make food industry less dependent on seasonal, climatic, and geographical variations.The present work deals with the biosynthesis of (Z)-3-hexen-1-yl butyrate as a model compound catalyzed by two commercial immobilized lipases from Mucor miehei and from Candida antarctica. Our purpose was to determine best experimental conditions and procedure to produce rather large amounts of C 6 alcohol-derived esters (150 to 250 g), at a laboratory scale, in a single operation as an intermediate step to pilot scale, our ultimate goal being the industrial production from natural acids and alcohols of esters considered to be natural (15)(16)(17). The impact of several parameters on the bioreaction was carefully investigated and optimized, i.e., the nature and the amount of enzyme, the substrate concentration, the temperature, and the acid/alcohol ratio. We also investigated C. antarctica-catalyzed synthesis of the title compound in the absence of solvent. MATERIALS AND METHODS Materials.Lipases from M. miehei immobilized on macroporous anion exchange resin Lipozym IM [5-6 Batch Acidolysis Units NOVO (BAUN)·g −1 , cloned into Aspergillus oryzae] and C. antarctica immobilized on acrylic resin Novozym 435 [7000 Propyl Laurate Units (PLU)·g −1 , cloned...

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Synthesis of Oleyl Oleate with Immobilized Lipase from Mucor miehei

Cited by 2 publications

References 5 publications

Lipase‐catalyzed synthesis of geranyl acetate in n‐hexane with membrane‐mediated water removal

Lipase‐catalyzed synthesis of geranyl acetate in n‐hexane with membrane‐mediated water removal

Synthesis of (Z)‐3‐hexen‐1‐yl butyrate in hexane and solvent‐free medium using Mucor miehei and Candida antarctica lipases

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