Solubility of Glucose in Mixtures Containing 2-Methyl-2-butanol, Dimethyl Sulfoxide, Acids, Esters, and Water

Tsavas, Panayiotis; Polydorou, Spyridoula; Faflia, Ioanna; Voutsas, Epaminondas; Tassios, Dimitrios P.; Flores, María Victoria; Naraghi, Kaynoush; Halling, Peter J.; Chamouleau, Francoise; Ghoul, Mohamed; Engasser, Jean‐Marc; Ferrer, Manuel; Plou, Francisco J.

doi:10.1021/je0102457

Cited by 35 publications

(33 citation statements)

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“…Results were within 1% of those reported previously by our group for fructose solubility for systems possessing ME mass fraction, ω ME , between 0 and 0.5 (13). The solubility of saccharide (fructose) at saturation, i.e., the mass fraction, ω S , increased linearly from 0.002 to 0.07 to 0.13 as ω ME increased from 0.00 to 0.47 to 0.80, in agreement with previously published results for fructose and glucose (13,16). Moreover, the phase boundary of Figure 1 can be described by the following linear equation: [1] where A and B equal 0.125 and 0.122, respectively.…”

Section: Resultssupporting

confidence: 91%

Feed batch addition of saccharide during saccharide‐fatty acid esterification catalyzed by immobilized lipase: Time course, water activity, and kinetic model

Dang

Obiri

Hayes

2005

J Americ Oil Chem Soc

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A conversion of 80-93% was achieved for esterification of oleic acid and fructose (or sucrose) catalyzed by immobilized Rhizomucor miehei lipase (Lipozyme IM; Novozymes, Franklinton, NC) at 65°C using near-stoichiometric amounts of substrates. The product consisted of mono-and diester at a ratio of 9:1 g g −1 . The main obstacle for achieving a high rate of reaction, the poor miscibility of the substrates, was overcome by taking advantage of the greatly increased solubility of fructose as the proportion of ester increased. A phase diagram demonstrated that the solubility of fructose increased linearly from 0.002 to 0.07 to 0.13 g g −1 as the ester mass fraction increased from 0.00 to 0.47 to 0.80, respectively. Solvent (tert-butanol) was present only during the first phase of the time course of the reaction to enhance fructose solubility and was allowed to evaporate away completely on reaching 25% conversion. A conversion higher than 80-93% could not be achieved by reducing the bioreactor's water content through use of vacuum pressure or water activity control. Water adsorption isotherms demonstrate the significant increase of equilibrium liquid phase water content as the reaction progressed, which was due to higher water adsorption by the monoester relative to oleic acid. Increased removal of liquid phase water may result in the loss of water from the lipase, resulting in a reduction of its biocatalytic activity. Initial rate experiments were used to derive a Ping-Pong Bi Bi kinetic model that strongly agreed with measured data for the time course of the reaction. Lipozyme IM did not lose activity when employed for three successive fructose-oleate esterification batch reactions or, equivalently, for a 24-d reaction period.Paper no. J10971 in JAOCS 82, 487-493 (July 2005). KEY WORDS: Fructose monoester, lipase, Lipozyme RM IM, Ping-Pong Bi Bi kinetic model, saccharide esters, water activity.Saccharide-FA partial esters have numerous applications in the food and cosmetics industries as biodegradable and biocompatible surfactants and as antibiotics and insecticides (1,2). The general approach for their synthesis, via base-catalyzed ester bond formation between saccharide and acyl donor feedstocks, requires a high operating temperature (above 100°C) and results in a broad product distribution (3,4). A more recent chemical method, using disodium hydrogen phosphate catalyst at 40°C, resulted in a high yield and selectivity but required the use of activated acyl donors, vinyl esters, resulting in an increase of time, labor, and materials costs (5). An alternative approach, the use of immobilized lipases in nearly anhydrous media, involves low operating temperatures and other mild reaction conditions and is thus environmentally friendly. As reviewed elsewhere (6,7), early results for this approach demonstrated high regioselectivity toward saccharide mono-and diester formation and high yields for the stoichiometrically limiting substrate but a slow reaction rate due to the poor miscibility of acyl donor and acceptor. Pol...

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Section: Resultssupporting

confidence: 91%

Feed batch addition of saccharide during saccharide‐fatty acid esterification catalyzed by immobilized lipase: Time course, water activity, and kinetic model

Dang

Obiri

Hayes

2005

J Americ Oil Chem Soc

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“…In fact, although the sucrose loading increases, the dissolved sucrose diminishes from 4.8 to 2 g l (1 when increasing the concentration of vinyl palmitate from 0.3 to 0.9 mol l (1 . A similar influence on sugar solubility with rising fatty acid concentration has been reported by Tsavas et al (2002aTsavas et al ( , 2002b. A similar effect occurs with methyl palmitate, although the sucrose solubility is slightly lower compared with vinyl donor (Table I).…”

Section: Effect Of Sucrose Loading On Conversion and Yieldsupporting

confidence: 82%

Parameters affecting productivity in the lipase-catalysed synthesis of sucrose palmitate

Reyes‐Duarte

López-Cortés

Ferrer

et al. 2005

Biocatalysis and Biotransformation

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The industrial application of lipases for the synthesis of sucrose esters is usually limited by its low productivity, as we need a medium where a polar reagent (the sugar) and a non-polar fatty acid donor are soluble and able to react in the presence of the biocatalyst. In this work, we have studied the problems encountered when trying to increase the volumetric productivity of sucrose esters. The synthesis of sucrose palmitate was performed in 2-methyl-2-butanol:dimethylsulfoxide mixtures by transesterification of different palmitic acid donors with sucrose, catalysed by the immobilized lipase from Candida antarctica B (Novozym 435). A protocol for substrate preparation different from that previously reported was found to improve the reaction rate. Several parameters, such as sucrose and acyl donor loadings, the percentage of DMSO in the mixture and the nature of acyl donor, were investigated. Under the best experimental conditions (15% DMSO, 0.1 mol l (1 sucrose, 0.3 mol l (1 vinyl palmitate), a maximum of 45 g l (1 sucrose palmitate was obtained in 120 h. Using methyl or ethyl palmitate, the highest productivity was 7.3 g l (1 in 120 h using 20% DMSO with 0.2 mol l (1 sucrose and 0.6 mol l (1 acyl donor. The formation of free fatty acid, and the effect of the percentage of DMSO on the monoester/diester selectivity were also studied. To our knowledge, this is the first report on enzymatic synthesis of sucrose esters of long fatty acids using alkyl esters as acyl donors.

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“…The apparatus and the procedure are similar to the case described in the literature. 16 A mercury-in-glass thermometer is inserted through the hole in the stopper for the measurement of the temperature of the flask. The thermometer had a measurement range from (263.15 to 373.15) K with an uncertainty of (0.05 K. Mixtures are prepared by mass using a Mettler H542 balance.…”

Section: Methodsmentioning

confidence: 99%

Solubility of 2,6-Diaminopyridine in Toluene, o-Xylene, Ethylbenzene, Methanol, Ethanol, 2-Propanol, and Sodium Hydroxide Solutions

Chen

Zeng

Pu³

2007

J. Chem. Eng. Data

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Solubilities are reported for 2,6-diaminopyridine dissolved at atmospheric pressure in toluene, o-xylene, and ethylbenzene from (273.25 to 361.25) K, methanol, ethanol, and 2-propanol between (266.15 and 321.25) K, and sodium hydroxide solution containing mass fraction of 0.000 % to 17.308 % sodium hydroxide over the temperature range of (273.55 to 326.35) K. Results of these measurements are fitted with the combined binary solvent Margules equation. For the systems studied, the Margules equation is found to provide very reasonable mathematical representation, with average deviations between experimental values and calculated ones being on the order of (2.2 % or less. The coupler parameters of the Margules equation (A 21 , A 12 ) and the enthalpy of fusion (∆ fus H) of 2,6-diaminopyridine in different systems are obtained by regressing the experimental data.

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Solubility of Glucose in Mixtures Containing 2-Methyl-2-butanol, Dimethyl Sulfoxide, Acids, Esters, and Water

Cited by 35 publications

References 13 publications

Feed batch addition of saccharide during saccharide‐fatty acid esterification catalyzed by immobilized lipase: Time course, water activity, and kinetic model

Feed batch addition of saccharide during saccharide‐fatty acid esterification catalyzed by immobilized lipase: Time course, water activity, and kinetic model

Parameters affecting productivity in the lipase-catalysed synthesis of sucrose palmitate

Solubility of 2,6-Diaminopyridine in Toluene, o-Xylene, Ethylbenzene, Methanol, Ethanol, 2-Propanol, and Sodium Hydroxide Solutions

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