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1.
The lipase-catalyzed synthesis of fatty acid fructose esters in organic media and in supercritical carbon dioxide
Saša Šabeder, Maja Leitgeb, Željko Knez, 2006, izvirni znanstveni članek

Opis: Sugar fatty acid esters are biodegradable surface active compounds in foodstuffs and cosmetics or pharmaceuticals. They have potential in replacing pollutant chemically synthesized surfactants. The enzymatic synthesis of fructose palmitate catalyzed by Candida antarctica B lipase was performed in different organic media in a batch react at atmospheric pressure. The influence of the organic solvent and temperature on the esterification was studied. Since supercritical carbon dioxide (SC CO2) has several advantages over organic solvents, such as high reaction rate, high mass transfer, non-toxicity, non flammability and low price, it was also chosen as a reaction medium for fructose palmitate production. The influence of temperature on immobilized lipase activity was studied at 10 MPa and the results were compared to the results obtained from reactions performed at atmospheric pressure under the same reaction conditions. The highest conversion (67%) was obtained after 24 hours of reaction in SC C02 at 80°C. A change of the particle size distribution and morphology of the untreated lipase and lipase treated with 2-methyl 2-butanol and SC C02 was observed. This article was presented at 1st SEECChE, held in Belgrade, September 25-28, 2005
Ključne besede: chemical processing, high pressure technology, supercritical CO2, lipase catalyzed syntheses, esterification, fructose palmitate, biocatalysts, lipase, Candida antarctica B
Objavljeno: 31.05.2012; Ogledov: 1500; Prenosov: 219
.pdf Celotno besedilo (392,53 KB)
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2.
Ionic liquids as (co)solvents for enzymatic reactions
Muzafera Paljevac, Maja Leitgeb, Željko Knez, 2006, izvirni znanstveni članek

Opis: Ionic liquids are low melting point salts that represent an excitnq new class of reaction solvents. Many reactions show advantages when carried out in ionic liquids, either with regard to enhanced reaction rates, improved selectivity, or easier reuse of catalysts. To ascertain the influence of ionic liquids on the enzyme activity three different ionic liquids, 1-butyl-3-methylimidazolium chloride ([bmim] [Cl]), 1-butyl-3-methylimidazolium hexafluorophosphate ([bmim] [PF6]) and 1-butyl-3-methylimidazolium tetrafluoroborate ([bmim][BF4]) were synthesized and investigated as potential media for the hydrolysis of carboxymethyl cellulose, catalyzed by non-immobilized cellulase from Humicola insolens (Celluzyme 0,7T) and for ester synthesis, catalyzed by immobilized lipase from Rhyomucor miehei (Lipozyme RM IM). Enzyme-catalyzed reactions were performed in a batch stirred reactor at atmospheric pressure. Celluzyme 0.7T showed better activity in hydrophobic ionic liquid ([bmim] [PF6]), as compared to hydrophilic ionic liquid ([bmim] [BF4]). In the case of Lipozyme RM IM, the synthetic activity of the enzyme was strongly reduced by incubating the enzyme in ionic liquids. Paper presented at the 1st South-East European congress of chemical engineering, Belgrade, September 25-28, 2005
Ključne besede: chemical processing, ion liquids, organic salts, biotechnology, enzymatic catalysis, immobilized lipase stability
Objavljeno: 31.05.2012; Ogledov: 1305; Prenosov: 202
.pdf Celotno besedilo (360,03 KB)
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3.
Enzymatic synthesis of sugar fatty acid esters in organic solvent and in supercritical carbon dioxide and their antimicrobial activity
Maja Leitgeb, Saša Šabeder, Željko Knez, 2008, izvirni znanstveni članek

Opis: Lipase-catalyzed synthesis of different sugar fatty acid esters was performed in high yields in 2-methyl-2-butanol at atmospheric pressure and in supercritical carbon dioxide (SC CO2) at 10 MPa. Influence of molecular sievesconcentration on conversion in SC CO2 was studied. Growth inhibitory effect of commercial sucrose fatty acid esters and enzymatically synthesized sucrose and fructose fatty acid esters on Gram-positive and Gram-negative micro-organisms, as well as on yeast was tested. Sucrose laurate inhibited the growth of Bacillus cereus food poisoning bacteria at a concentration of 9.375 mg/ml.
Ključne besede: biocatalysis, lipase, sugar fatty acid ester, organic solvent, cupercritical CO2, antimicrobial activity
Objavljeno: 31.05.2012; Ogledov: 1307; Prenosov: 67
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4.
Enzyme-catalyzed acylation of (R,S)-1-phenylethanol in 1-butyl-3-methylimidazolium based ionic liquids
Muzafera Paljevac, Željko Knez, Maja Leitgeb, 2009, izvirni znanstveni članek

Opis: Ionic liquids represent an exciting new class of reaction solvents for catalysis, which have been used successfully for enzyme-catalyzed reactions. In present research, three different ionic liquids, 1-butyl-3-methylimidazolium tetrafluoroborate, 1-butyl-3-methylimidazolium hexafluorophosphate, and 1-ethyl-3-methylimidazolium bis[(trifluoromethyl)sulfonyl)] amide, were synthesized. They were used as a reaction medium for enzyme-catalyzed acylation of (R,S)-1- phenylethanol with vinyl acetate. Mentioned enzymatic reaction was performed in a batch stirred-tank reactor in order to optimise different reaction parameters (biocatalyst concentration, temperature, ...). The influence of three different immobilized lipases on reaction performance was studied as well. The highest reaction rate and conversion of 49.7% after 5 h of reaction performance was achieved in the case when immobilized lipase Novozym 435 from Candida antarctica was used as a biocatalyst and hydrophilic ionic liquid 1-butyl- 3-methylimidazolium tetrafluoroborate as a solvent. Therefore, the optimization of different reaction parameters on lipase- catalyzed acylation of (R,S)-1-phenylethanol was carried out in 1-butyl-3-methylimidazolium tetrafluoroborate.
Ključne besede: immobilized lipase, acylation, (R, S)-1-phenylethanol, ionic liquids, 1-butyl-3-methylimidazolium tetrafluoroborate
Objavljeno: 31.05.2012; Ogledov: 1201; Prenosov: 26
.pdf Celotno besedilo (271,40 KB)
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5.
Lipase-catalyzed transesterification of (R,S)-1-phenylethanol in SC $CO_2$ and in SC $CO_2$/ionic liquid systems
Muzafera Paljevac, Željko Knez, Maja Leitgeb, 2009, izvirni znanstveni članek

Opis: Commercial immobilized lipase B from Candida antarctica (CALB) was successfully applied to catalyzing the transesterification of (R,S)-1-phenylethanol in supercritical carbon dioxide and in supercritical carbon dioxide/ionic liquid biphasic system. Firstly, the variables affecting the performance of CALB in transesterification reactions in supercritical carbon dioxide, such as CALB concentration, temperature and pressure, were studied. An increase in the conversion and in the reaction rate was observed as the CALB/substrate ratio, temperature and pressure, were increased from 4.3 to 19.9, from 40 °C to 80 °C and from 8 MPa to 10 MPa, respectively. Further increase in temperature from 80 °C to 120 °C and pressure from 10 MPa to 30 MPa resulted in lower conversion and lower initial reaction rate. Furthermore, different vinyl esters were used as acyl donors for CALB-catalyzed transesterification of (R,S)-1-phenylethanol in supercritical carbon dioxide. The highest initial reaction rate was attained with vinyl butyrate, although 50% conversion was attained faster when vinyl acetate was used as acyl donor. Secondly, in transesterification of (R,S)-1-phenylethanol, performed in supercritical carbon dioxide/ionic liquid biphasic system, influence of concentration of 1-butyl-3-methylimidazolium tetrafluoroborate [bmim][BF$_4$] was studied. The addition of 50 mmol (70% w/w reaction mixture) of [bmim][BF$_4$] to the reaction system gave the best result in terms of transesterification rate.
Ključne besede: candida antarctica lipase B, transesterification, (R, S)-1-phenylethanol, ionic liquids, vinyl acetate, supercritical carbon dioxide
Objavljeno: 31.05.2012; Ogledov: 1428; Prenosov: 46
.pdf Celotno besedilo (446,49 KB)
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6.
Comparison of the esterification of fructose and palmitic acid in organic solvent and supercritical carbon dioxide
Saša Šabeder, Maja Leitgeb, Željko Knez, 2005, izvirni znanstveni članek

Opis: Sugar fatty acid esters are nonionic surfactants, which are used for personal care products, cosmetic applications, and as emulsifiers for food. In recent years, enzymatic synthesis of sugar fatty acid esters is attracting keen attention as a new manufacturing method for future application. Reaction parameters of lipase-catalyzed synthesis of fructose fatty acid esters in organic solvent were optimized in a batch reactor at atmospheric pressure. Optimum conditions for reaction performed in organic solvent at atmospheric pressure were 10% (wžw of substrates) of lipase from Candida antarctica B, 12.14% (wžw of reaction mixture) of molecular sieves at 60 C, and stirring rate of 600 rpm. Esterification of fructose and palmitic acid was performed insupercritical carbon dioxide with and without addition of cosolvent (organicsolvent) at 60 C. Effect of pressure on enzyme activity was studied.
Ključne besede: chemical processing, high pressure technology, supercritical CO2, esterification, organic solvent, lipase catalysed synthesis, fructose fatty esters, Candida antarctica B, enzyme activity
Objavljeno: 01.06.2012; Ogledov: 1282; Prenosov: 45
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7.
Enzymatic synthesis of isoamyl acetate with immobilized Candida antarctica lipase in supercritical carbon dioxide
M.P. Romero, L. Calvo, C. Alba, Maja Leitgeb, Mateja Primožič, Željko Knez, 2005, izvirni znanstveni članek

Opis: Isoamyl acetate was successfully synthesized from isoamyl alcohol in supercritical carbon dioxide by enzymatic catalysis. First, the impact of the acyl donor was investigated. Among several reactants, including acetic acid and two different acetates, acetic anhydride gave best yields. Then, two different immobilized lipases (Novozym 435 from Candida antarctica and Lipozyme RM-IM from Rhizomucor miehei) as biocatalysts for the above-mentionedreaction were compared. An esterification extent of 100% was obtained in continuous operation using acetic anhydride as acyl donor and Novozym 435 as enzyme. The amount of enzyme preparation was optimised to 6.25 g/mol alcohol. The effect of substrates load in the solvent was investigated. Operating at a CO2žsubstrates molar ratio below 7.0, the conversion of alcoholdecreased, probably due to an inhibitory effect on enzyme by high concentration of acetic anydride or by produced acetic acid. Pressure in the range of 8-30 MPa showed no effect on this reaction, while an increase in temperature (over 313 K) led to lower production of isoamyl acetate. Novozym 435 was very stable not finding any loss of activity during one month of continuous operation. Finally, carbon dioxide was compared to a conventional organic solvent (n-hexane). Initial reaction rate was higher in SC-CO2, although final esterification extent was similar in both media.
Ključne besede: chemical processing, high pressure technology, superkritical CO2, ester synthesis, isoamyl acetate, enzymatic catalysis, immobilized lipase, isoamyl acetate production, natural flavors
Objavljeno: 01.06.2012; Ogledov: 1296; Prenosov: 63
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8.
Enzymatic fatty ester synthesis
Simona Pečnik, Željko Knez, 1992, izvirni znanstveni članek

Opis: Fatty ester synthesis with immobilized 1,3-specific lipase from Mucor Miehei is described. 1,2-Isopropylidene glycerol was peoduced by condensation of glycerol with acetone was esterified with oleic acid in the presence of a Mucor Miehei lipaze (Lipozyme TM) to obtain 1,2 isopropylidene- 3-oleoyl glycerol. The effects of various process parameters (temperature and pressure)and various ratios (enzyme/substrate) have been investigated to determine optimal conditions for the esterification process. The highest conversion of oleic acid (80% w/w) was obtained at 55 oC and 57.057 bar, while the optimal addition of lipase to substrate was determined to be 0,096 g per gram of reaction mixture. The esterification can be modelled successfully as a reverse second order reaction. Thermodynamic properties of the reaction system at 55 oC and 0.057 bar were also determined. Activation energy was 20.82 kJ/mole, entropy of activation -0,26 kJ/(Kmole) and free energy of activation was 103.32 kJ/mole.
Ključne besede: chemical engineering, biotechnology, esterification, syntheses, esters, enzymes, lipase, Mucor miehei, reaction kinetics, reaction thermodynamics, 1, 2-isopropylidene-3-oleoyl glycerol
Objavljeno: 06.06.2012; Ogledov: 1304; Prenosov: 58
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9.
Enzymatic esterification of glycerol and stearic acid in non-conventional media
Zsófia Csanádi, Katalin Bélafi-Bakó, Eszter Szentgyörgyi, László Gubicza, Željko Knez, Maja Leitgeb, 2010, izvirni znanstveni članek

Opis: Ionic liquids as trihexyl-tetradecyl-phophonium-dicyanamide (Cyphos 105) and cocosalkyl-pentaethoxi-methyl-ammonium-methosulfate (Ammoeng 100) were applied for the esterification of stearic acid and glycerol using Candida antarctica lipase (Novozyme 435). When only ILs were applied as solvents at 1:15 initial substrate molar ratio the conversion was 76 and 78 % in the case of two kinds of ILs, respectively. Mixed the ILs and supercritical $CO_2$ the conversion reached 79 and 86 %. The conversion was found highest in supercritical $CO_2$, reached 90 %. Moreover formation of glycerol-di-stearate is much lower in the case of ILs comparing with $SCCO_2$.
Ključne besede: glycerol-mono-stearate, Lipase, ionic liquids, supercritical $CO_2$, carbon dioxide
Objavljeno: 10.07.2015; Ogledov: 441; Prenosov: 54
.pdf Celotno besedilo (128,92 KB)
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