Improving the environmental compatibility of enzymatic synthesis of sugar-based surfactants using green reaction media

Vuillemin, Marie E.; Husson, Éric; Jamali, Arash; Lambertyn, Virginie; Pilard, Serge; Cailleu, Dominique; Sarazin, Catherine

doi:10.1016/j.procbio.2022.03.015

Cited by 9 publications

(9 citation statements)

References 65 publications

(93 reference statements)

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“…These solutions were prepared to investigate the influence of lauric acid on the system’s behavior. The molar ratios (0.3 mol %, 1.3 mol %, and 2.5 mol %) were chosen based on preliminary studies by Vuillemin et al and Barros et al The initial concentration of lauric acid was established by considering the future molar ratio of lauric acid to glucose to be employed in enzymatic reactions, equivalent to six moles of lauric acid for each mole of glucose. The amount analyzed did not impact the transition pressure, so the amount of lauric acid was increased to anticipate its behavior in the presence of glucose.…”

Section: Methodsmentioning

confidence: 99%

“…To overcome this limitation, one strategy adopted is the incorporation of cosolvents , such as 2-methyltetrahydrofuran-3-one (MeTHF-3-one), recognized for its effectiveness in supercritical environments . Widely used in the food industry and considered safe (GRAS), MeTHF-3-one improves the solubility of substrates, optimizing the interaction between the enzyme and reagents . This results in higher reaction rates, contributing to process efficiency. , Despite the environmental benefits, biodegradability, and safety offered by MeTHF-3-one, its use is still little explored, which may limit its application on an industrial scale.…”

Section: Introductionmentioning

confidence: 99%

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Phase Equilibrium and Thermodynamic Modeling of 2-Methyltetrahydrofuran-3-one, Carbon Dioxide, and Lauric Acid Systems

Barros,

Rebelatto,

Mayer

et al. 2024

J. Chem. Eng. Data

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In this study, the phase equilibrium behavior of the ternary system (CO 2 + MeTHF-3-one + lauric acid) was investigated to provide insights into the enzymatic synthesis of sugar-based surfactants. Experimental data were obtained over the 313.15 to 343.15 K temperature range and at pressures of up to 13.02 MPa using a static synthetic method with a variable volume visualization cell. Three different concentrations of lauric acid for MeTHF-3-one, 0.3%, 1.3%, and 2.5 mol %, were examined. Vapor− liquid transitions were successfully observed and modeled by the Peng−Robinson equation of state with the PR-vdW2 variant. Adding lauric acid did not impact the transition pressures compared with CO 2 -MeTHF-3-one binary systems. The LCST behavior type, with increasing transition pressures as temperatures increased, was consistent across all systems studied.

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Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Phase Equilibrium and Thermodynamic Modeling of 2-Methyltetrahydrofuran-3-one, Carbon Dioxide, and Lauric Acid Systems

Barros,

Rebelatto,

Mayer

et al. 2024

J. Chem. Eng. Data

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“…6-O-lauroyl-(α/β)-D-glucopyranose was obtained as a white solid and characterized as follows [19,33,37…”

Section: Enzymatic Synthesismentioning

confidence: 99%

“…Tertiary alcohols are reported in co-solvent systems too [31,32]. More recently, agro-based solvents have received attention, such as methylated derivatives of tetrahydrofuran [33], which are biobased and less toxic than THF, but expensive. Mixed organic solvents, so-called co-solvents, are generally preferred to the single solvent because the solvent ratio allows a variation in the solubility at the beginning of the reaction.…”

Section: Introductionmentioning

confidence: 99%

Optimization of Enzymatic Synthesis of D-Glucose-Based Surfactants Using Supported Aspergillus niger Lipase as Biocatalyst

Spalletta,

Joly,

Martin

2023

Chemistry

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Surfactants are amphiphilic molecules with the ability to modify the surface tension between two surfaces. They can be obtained by various methods, the main one being synthetic, from petroleum-based substrates. Their universal use in a wide range of fields has created a global market and, consequently, ecological, and economic expectations for their production. Biocatalyzed processes, involving enzymes, can address this objective with processes complying with the principles of green chemistry: energy saving, product selectivity, monodispersity, and reduction in the use of solvents, with energy eco-efficiency. For example, fatty-acid carbohydrate esters are biobased surfactants that can be synthesized by lipases. In this work, we were interested in the synthesis of D-glucose lauric ester, which presents interesting properties described in the literature, with Aspergillus niger lipase, rarely described with sugar substrates. We optimized the synthesis for different parameters and reaction media. This lipase appeared to be highly selective for 6-O-lauroyl-D-glucopyranose. However, the addition of DMSO (dimethyl sulfoxide) as a co-solvent displays a duality, increasing yields but leading to a loss of selectivity. In addition, DMSO generates more complex and energy-intensive purification and processing steps. Consequently, a bio-sourced alternative as co-solvent with 2MeTHF3one (2-methyltetrahydrofuran-3-one) is proposed to replace DMSO widely described in the literature.

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“…Sugar fatty acid esters have a market value that is at least two orders of magnitude greater than ethanol. [7][8][9] To date, SFAEs have mainly been produced using glucose; [10][11][12][13][14][15][16][17][18][19][20][21][22][23] the use of xylose thus represents a novel use of this sugar.…”

mentioning

confidence: 99%

Production of sugars from mixed hardwoods for use in the synthesis of sugar fatty acid esters catalyzed by immobilized‐stabilized derivatives of Candida antarctica lipase B

Gonçalves

Cansian

Tardioli

et al. 2023

Biofuels Bioprod Bioref

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The synthesis of sugar fatty acid esters (SFAEs) from lignocellulosic biomass and oleic acid (C18:1) was catalyzed by immobilized‐stabilized derivatives of Candida antarctica lipase B in a methyl ethyl ketone medium. After steam‐explosion pretreatment of mixed hardwoods and enzymatic hydrolysis at 15%wt solids, xylose and glucose were purified/concentrated to a mass ratio of ~3 to 1. These lignocellulosic sugars were superior to commercial sugars as the carbohydrate source for the esterification reaction in terms of sugar conversions. The highest conversions were obtained using 1.5% w/v of Novozyme 435 (N435, uncoated) as the biocatalyst for the synthesis of SFAEs. Coating the N435 with polyethyleneimine (PEI) prevented enzyme leakage into the reaction medium and produced 35% and 50% higher xylose and glucose conversions to SFAEs, respectively, at the same enzyme loading. After six 24 h reuse cycles with the PEI‐coated N435, xylose conversion decreased by 44%, while a 65% reduction in xylose conversion was observed with the uncoated lipase. Mass spectrometry analysis confirmed the production of xylose and glucose mono‐ and di‐esters. Our purified product presented an emulsion capacity (EC) close to that of a commercial sugar ester and the ECs of the xylose oleate, laurate, and palmitate synthesized in previous studies.

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Improving the environmental compatibility of enzymatic synthesis of sugar-based surfactants using green reaction media

Cited by 9 publications

References 65 publications

Phase Equilibrium and Thermodynamic Modeling of 2-Methyltetrahydrofuran-3-one, Carbon Dioxide, and Lauric Acid Systems

Phase Equilibrium and Thermodynamic Modeling of 2-Methyltetrahydrofuran-3-one, Carbon Dioxide, and Lauric Acid Systems

Optimization of Enzymatic Synthesis of D-Glucose-Based Surfactants Using Supported Aspergillus niger Lipase as Biocatalyst

Production of sugars from mixed hardwoods for use in the synthesis of sugar fatty acid esters catalyzed by immobilized‐stabilized derivatives of Candida antarctica lipase B

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