Rapid and high yields of synthesis of butyl acetate catalyzed by Novozym 435: Reaction optimization by response surface methodology

Martins, Andréa Bercini; Graebin, Natália G.; Lorenzoni, André Soibelmann Glock; Fernández‐Lafuente, Roberto; Ayub, Marco Antônio Záchia; Rodrigues, Rafael C.

doi:10.1016/j.procbio.2011.09.011

Cited by 103 publications

(96 citation statements)

References 35 publications

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“…In contrast, lipase from Candida antarctica was found to have fatty acid specificity to straight chain fatty acid with 10-18 carbon atoms. For instance, lower fatty acid such as hexanoic, octanoic, and unsaturated 9-cis octadecenoic acid, were found to be poor substrates for ethyl D-glucopyranoside esters [14,16].…”

Section: Discussionmentioning

confidence: 99%

“…Enzymatic synthesis of wax ester, adipate ester, hexyl laurate, pentyl octanoate, and ethyl butyrate have been conducted in STR using solvent and solvent-free system with significant high yield of up to 80% [6,[16][17][18][19][20]. The combination of supercritical fluid and molecular sieves can improve the yield of sugar esters up to 67% [18,21].…”

Section: Discussionmentioning

confidence: 99%

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Lipase-Catalyzed Synthesis of Kojic Acid Derivative in Bioreactors and the Analysis of Its Depigmenting and Antioxidant Activities

et al. 2017

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Abstract:In this study, 7-O-kojic acid monopalmitate (7-O-KAP) was synthesized using palmitic acid and kojic acid where the yield and biological activities were analyzed. The highest yield of 7-O-KAP (43%) can be obtained at molar ratio of 1:1, enzyme loading of 5% (w/v), temperature of 70 • C, using immobilized lipase N435 in solvent-free system. Stirred tank reactor (STR) provides better mixing of the substrates and biocatalyst with better yield of 7-O-KAP, compared to fluidized tank reactor (FTR) and packed bed reactor (PBR). The 7-O-KAP exhibited pseudoplastic behavior with flow behavior index (n) being less than 1. The 7-O-KAP showed better depigmenting activity with the reduction of melanin content in Danio rerio embryo to 18.70%, significantly lower than the positive control, kojic acid (60.39%) at highest concentration tested (250 µg/mL). Intracellular tyrosinase in Danio rerio embryo was also reduced when treated with 7-O-KAP (12.53%), compared to kojic acid (37.36%) at concentration of 250 µg/mL. In FRAP assay, 7-O-KAP had antioxidant activity of 8156 AAE/mL, which was higher than kojic acid (6794 AAE/mL) at concentration of 2 mg/mL. The 7-O-KAP also reduced peroxidation activity to 12.21%, which was better compared to kojic acid (31.68%) at 2 mg/mL. Moreover, it was found that lipid peroxidation activity of 7-O-KAP (12.21%) was comparable to BHT (11.56%) at 2 mg/mL. Based on this study, 7-O-KAP could be an alternative compound for whitening agent and antioxidant compared to kojic acid and BHT, respectively.

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Section: Discussionmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 99%

Lipase-Catalyzed Synthesis of Kojic Acid Derivative in Bioreactors and the Analysis of Its Depigmenting and Antioxidant Activities

et al. 2017

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“…[41,54] Furthermore, an excess of alcohol will shift the thermodynamic equilibrium of the reaction towards the formation of ester. [49] Attaining optimum conditions and model verification The highest percentage conversion from the various run was 89.9% at 14 h of reaction time, 50 C and substrate molar ratio of 1:4 oleic acid:methanol (Table 2). Minimizing the production cost is an important aspect to keep in mind [41] when developing industrial processes for the esterification of methanol with oleic acid for the production of detergents, emulsifiers, wetting agents and also as intermediate stabilizers.…”

Section: Rsm Experiments and Model Fittingmentioning

confidence: 99%

“…The outcome can be explained by the thermodynamics of the reaction, which favour product formation when the starting material is present in excess. [50] For that very reason, many lipase catalysed esterification reactions intentionally employ an excess of alcohol to improve the yield of ester, [50] apart from reducing the toxicity of the acids in the reaction medium that could deactivate enzyme activity. [51] Effect of temperature and molar ratio Figure 10 depicts the mutual interaction on effect of temperature with molar ratio at a constant time of 10 h on the CRL-MWCNTs catalysed synthesis of methyl oleate.…”

Section: Rsm Experiments and Model Fittingmentioning

confidence: 99%

Modelling and optimization ofCandida rugosananobioconjugates catalysed synthesis of methyl oleate by response surface methodology

Marzuki

Huyop

Aboul‐Enein

et al. 2015

Biotechnology & Biotechnological Equipment

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Esters, such as methyl oleate, are functionally important compounds in many industrial sectors, mainly as components for manufacturing of emulsifiers, detergents, intermediate stabilizers and wetting agents. Acid functionalization of multiwalled carbon nanotubes (F-MWCNTs) by using a mixture of HNO 3 and H 2 SO 4 (1:3, v:v) was employed as the matrix for the adsorption of Candida rugosa lipase (CRL) as nanobioconjugates (CRL-MWCNTs) for the production of methyl oleate. Structural information of the developed CRL-MWCNTs was confirmed using Fourier Transform Infrared spectroscopy, thermogravimetric analysis and transmission electron microscopy, which revealed a successful attachment of CRL onto the F-MWCNTs. Process parameters (reaction time, temperature and alcohol:acid molar ratio) were optimized for high percent conversion of methyl oleate. Structural analysis established that CRL was successfully attached to the surface of the F-MWCNTs. Under the optimized conditions, which were 13.87 h, 51 C, molar ratio oleic acid: methanol (1:3.80), a high ester yield of 90.90% was attained. Also, under conditions of the shortest reaction time of 6 h, 47.07 C and acid:methanol ratio of 1:2.54, the CRL-MWCNTs catalysed a 74.51% ester yield. Hence, we established that response surface methodology (RSM) can be a practical technique for the prediction of the conditions that favour the high yield production of methyl oleate. Under optimized conditions, the CRL-MWCNTs nanobioconjugates are potentially good and economical biocatalysts for the production of methyl oleate, as well as other types of commercially important fatty-acid methyl esters.

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“…For instance, in certain cases, the immobilized enzyme is used in organic medium, and it is inactivated under operation due to the accumulation of hydrophilic compounds in the surroundings of the enzyme environment (e.g., water, glycerin, short chain carboxylic acids, etc.). This occurs, for example, in the production of biodiesel or esterification reactions [10][11][12]. Thus, the use of a very hydrophobic support may reduce and even eliminate this problem [13], compensating a decrease in the enzyme thermostability (Fig.…”

Section: Introductionmentioning

confidence: 99%

Immobilization of Proteins in Poly-Styrene-Divinylbenzene Matrices: Functional Properties and Applications

Rafael¹,

Hernández²,

Barbosa³

et al. 2015

COC

Self Cite

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Supports based on poly-styrene-divinylbenzene (PSD) are commercially available since a long time ago. However, they are not commonly used as enzyme immobilization matrices. The main reason for this lies in the negative effect of the very hydrophobic surface on enzyme stability that produces the instantaneous enzyme inactivation in many instances. However, they have recently regained some impact on enzyme immobilization. They are easy to modify, and have been prepared with different modifiers. We will pay special attention to the coating of these supports with ionic liquids, which permits to have the ionic liquid phase anchored to the solid and modulate the enzyme properties without risk of losing these expensive and potentially toxic compounds. Thus, this review will present the covalent or physical immobilization of enzymes on PSD supports, submitted to different modifications. Moreover, lipases immobilized via interfacial activation on some naked PSD supports have shown some unexpected improvement in their catalytic properties, with uses in reactions like hydrolysis, esterification or transesterification.

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Rapid and high yields of synthesis of butyl acetate catalyzed by Novozym 435: Reaction optimization by response surface methodology

Cited by 103 publications

References 35 publications

Lipase-Catalyzed Synthesis of Kojic Acid Derivative in Bioreactors and the Analysis of Its Depigmenting and Antioxidant Activities

Lipase-Catalyzed Synthesis of Kojic Acid Derivative in Bioreactors and the Analysis of Its Depigmenting and Antioxidant Activities

Modelling and optimization ofCandida rugosananobioconjugates catalysed synthesis of methyl oleate by response surface methodology

Immobilization of Proteins in Poly-Styrene-Divinylbenzene Matrices: Functional Properties and Applications

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