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

Shaw, Jei‐Fu; Chang, Shu‐Wei; Liao, Hui-Fen; Shieh, Chwen‐Jen

doi:10.1002/jsfa.1588

Cited by 5 publications

(4 citation statements)

References 4 publications

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“…It is applicable to both chemical and enzymatic catalysis. RSM has been used in both biodiesel production and other applications ,,,, . Shieh et al used Rhizomucor lipase (Lipozyme IM-77) to catalyze the alcoholysis of soybean oil with methanol to obtain a 92 wt % conversion to biodiesel in 6.3 h at 37 °C using a methanol/soybean oil molar ratio of 3.4:1 in the presence of 5.8% added water.…”

Section: Response Surface Methodology (Rsm)mentioning

confidence: 99%

Enzymatic Approach to Biodiesel Production

Akoh

Chang

Lee³

et al. 2007

J. Agric. Food Chem.

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364

209

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The need for alternative energy sources that combine environmental friendliness with biodegradability, low toxicity, renewability, and less dependence on petroleum products has never been greater. One such energy source is referred to as biodiesel. This can be produced from vegetable oils, animal fats, microalgal oils, waste products of vegetable oil refinery or animal rendering, and used frying oils. Chemically, they are known as monoalkyl esters of fatty acids. The conventional method for producing biodiesel involves acid and base catalysts to form fatty acid alkyl esters. Downstream processing costs and environmental problems associated with biodiesel production and byproducts recovery have led to the search for alternative production methods and alternative substrates. Enzymatic reactions involving lipases can be an excellent alternative to produce biodiesel through a process commonly referred to alcoholysis, a form of transesterification reaction, or through an interesterification (ester interchange) reaction. Protein engineering can be useful in improving the catalytic efficiency of lipases as biocatalysts for biodiesel production. The use of recombinant DNA technology to produce large quantities of lipases, and the use of immobilized lipases and immobilized whole cells, may lower the overall cost, while presenting less downstream processing problems, to biodiesel production. In addition, the enzymatic approach is environmentally friendly, considered a "green reaction", and needs to be explored for industrial production of biodiesel.

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Section: Response Surface Methodology (Rsm)mentioning

confidence: 99%

Enzymatic Approach to Biodiesel Production

Akoh

Chang

Lee³

et al. 2007

J. Agric. Food Chem.

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364

209

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“…The essential reactions of biodiesel component biosynthesis are transesterification of oils or triacylglycerols, alcoholysis, acidolysis and, in certain cases, direct esterification of alcohols by fatty acids [17][18][19]. Esterification of long-chain oleic acid with oleyl alcohol, which is also an attractive reaction for biolubricant production, is not studied enough.…”

Section: Resultsmentioning

confidence: 98%

Lipazės aliejų perdirbimui. Eksperimentinė kai kurių fermentų ir substratų atranka biodyzelino komponentų gamybai

Bendikienė¹,

Juodka²,

Surinėnaitė³

et al. 2008

Biologija

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Lipases of different origin were screened for substrates and different reactions from the practical approach to search for the optimal conditions for biodiesel component production. The commercial lipases under analysis were shown to be specific to p-nitrophenyl fatty acid esters of medium chain length, although Lipolase100 LEX also showed a relatively high hydrolytic activity on p-nitrophenyl palmitate. The soluble Enterobacter aerogenes lipase was shown also to be the most active when hydrolysing medium-chain-length p-nitrophenyl fatty acid esters. The specificity of immobilized commercial lipases did not change as compared with soluble analogues. The immobilized Enterobacter aerogenes lipase showed no significant differences of activity towards p-nitrophenyl butyrate and medium-chain p-nitrophenyl fatty acid esters versus the attached enzyme on polyurethane and chitosan and also showed the highest hydrolytic activity on p-nitrophenyl caprylate as for soluble lipase. Enterobacter aerogenes lipase-catalyzed esterification of oleic acid with oleoyl alcohol was a long-lasting process still in progress after 91 hours. The lipase showed the highest catalytic activity when esterifying oleic acid with ethanol and 1.2-ethanediol. The enzyme slightly esterified the acid with 1.3-propanediol and was almost inactive for esterification with 2-hydroxyethyl ether. Enterobacter aerogenes lipase more efficiently hydrolysed camelina oil than rapeseed oil, considering the former to be an alternative source to be converted into biodiesel components. Methanolysis of rapeseed oil catalyzed by the lipase adsorbed on chitin was also a long-lasting process still in progress during 124 hours. The optimal glycerol-tricaprylate-to-methanol ratio was 1 : 1 for methanolysis of the substrate catalysed by Resinase HT lipase immobilized on a polyurethane support. The lipase was completely depressed at the ratio 1 : 3.

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“…hexyl butyrate, are extremely fragrant compounds and widely used in the food industry [8], different hexyl esters were synthesized by direct esterification of several carboxylic acids, using the immobilized lipase Novozym 435 s from Candida antarctica. As hexyl esters with ecolabeled flavor, e.g.…”

Section: Introductionmentioning

confidence: 99%

“…As hexyl esters with ecolabeled flavor, e.g. hexyl butyrate, are extremely fragrant compounds and widely used in the food industry [8], different hexyl esters were synthesized by direct esterification of several carboxylic acids, using the immobilized lipase Novozym 435 s from Candida antarctica. Finally, it was attempted to prove the viability of supercritical carbon dioxide (SCCO 2 ) as an alternative to organic solvents.…”

Section: Introductionmentioning

confidence: 99%

Enzymatic synthesis of short‐chain esters in n‐hexane and supercritical carbon dioxide: Effect of the acid chain length

Diaz¹,

Gómez²,

Díaz-Suelto³

et al. 2010

Engineering in Life Sciences

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Enzymatic synthesis is the preferred way to produce so‐called “natural products.” Hydrolases have been used for short‐chain ester synthesis. These esters present a pleasant flavor and they have a lot of applications in different industries. Novozym 435 from Candida antarctica (EC 3.1.1.3, triacylglycerol lipase) was used for hexyl ester synthesis in n‐hexane and supercritical carbon dioxide (SCCO2). Direct esterification provided higher yields than transesterification for the synthesis of esters. Several carboxylic acids of different chain lengths were tested for the esterification reactions: acetic, propionic, butyric, caproic and caprylic acids. The reactions were carried out at 40°C and the amount of enzyme used was 13.8 g/mol alcohol. Substrates were added at equimolar concentrations, with sufficient stirring to avoid external diffusion control. Different substrate concentrations up to 1.5 M were used. The working pressure was 14 MPa in the case of SCCO2 and atmospheric pressure in the case of organic solvent. The results in both solvents show that the reaction rate increases with the chain length of the acid, but the final yields were similar. However, some of the reactions prove to be faster in SCCO2, except for hexyl acetate and propionate synthesis, in which acetic and propionic acid presented a lower solubility in SCCO2 due to its high polarity. Moreover, an acetic acid concentration of 1.5 M brought about a strong inhibition of the enzyme activity.

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

Cited by 5 publications

References 4 publications

Enzymatic Approach to Biodiesel Production

Enzymatic Approach to Biodiesel Production

Lipazės aliejų perdirbimui. Eksperimentinė kai kurių fermentų ir substratų atranka biodyzelino komponentų gamybai

Enzymatic synthesis of short‐chain esters in n‐hexane and supercritical carbon dioxide: Effect of the acid chain length

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