Ultrasound-assisted enzymatic synthesis of xylitol fatty acid esters in solvent-free conditions

Nieto, Susana; Villa, Rocío; Donaire, Antonio; Lozano, Pedro

doi:10.1016/j.ultsonch.2021.105606

Cited by 18 publications

(15 citation statements)

References 30 publications

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“…Similarly, based on the same considerations, better diffusion and distribution of the substrate and BCL, pore-making (macropores), and reduction of the macrosize can improve the catalytic efficiency (Figure 5b,c). Similar as reported in some literature studies, 28,46 ultrasonic treatment also helped to improve the enzyme activity to a certain extent (Figure 5d). These findings gave us some inspiration for the design of lipase-hybrid gel reactors; that is, the assembly of a large reactor from small lamellar-like gels, which are as thin as possible and have holes through them, will produce the desired catalytic performance.…”

Section: Catalytic Characteristics Of the Hybrid Gel Interfacial Cata...supporting

confidence: 89%

Novel Lipase Reactor based on Discontinuous Interfaces in Hydrogel-Organogel Hybrid Gel: A Preliminary Exploration

Ming

Sun

Chen

et al. 2023

J. Agric. Food Chem.

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According to the "interfacial activation" mechanism, constructing a sufficient interface is the key strategy for lipasecatalytic system designing. Based on the "infinite interface in finite three-dimensional space" logic, in the current study, poly(N,Ndimethylacrylamide) (PDMA)-polybutyl methacrylate (PBMA) hybrid gels were prepared by a two-step crosslinking strategy, subsequently constructed as lipase-interfacial catalytic systems. The results confirm that the PDMA-PBMA hybrid gels with "networks in pores" structures could swell both the aqueous phase and organic phase. The balance between water swelling and isooctane swelling, hybrid gel space (height control), and the lipase entry manner significantly affect the interface construction and consequently the catalytic efficiency. The enzyme−substrate contact rate affected by swelling leads to three catalytic stages. Considering the spatial barrier and distribution of lipases, a potential high-performance lipase reactor can be assembled from smallsize, lamellar-like, and porous hybrid gels. The reactors also show good time storage and low temperature tolerance.

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Section: Catalytic Characteristics Of the Hybrid Gel Interfacial Cata...supporting

confidence: 89%

Novel Lipase Reactor based on Discontinuous Interfaces in Hydrogel-Organogel Hybrid Gel: A Preliminary Exploration

Ming

Sun

Chen

et al. 2023

J. Agric. Food Chem.

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“…The conditions for the ultrasound-assistance setup were 40 °C, 70% amplitude, and 2 h reaction time, as previously reported. 28 …”

Section: Methodsmentioning

confidence: 99%

“…, xylitol) under solvent-free conditions. Thus, the use of ultrasounds was key to overcoming the mutual immiscibility of fatty acids and xylitol substrates and the semisolid character of the initial reaction mixtures, enabling the transport of substrate molecules to the enzyme catalytic site for an efficient synthesis of xylityl monoacyl and diacyl esters as the main products with a 96% yield …”

Section: Introductionmentioning

confidence: 99%

“…Thus, the use of ultrasounds was key to overcoming the mutual immiscibility of fatty acids and xylitol substrates and the semisolid character of the initial reaction mixtures, enabling the transport of substrate molecules to the enzyme catalytic site for an efficient synthesis of xylityl monoacyl and diacyl esters as the main products with a 96% yield. 28 Here, this work reports on the evaluation of different green protocols, i.e., ultrasound assistance, orbital shaking, rotary evaporator, and 500 g stirred reactor (see Figure 1B) for the biosynthesis and scale-up of PME synthesis under solvent-free conditions. The influence of the alkyl-chain length of the fatty acid, the amount of the enzyme, as well as the role of different setups for mixing that can be coupled to a vacuum system have been studied, being selected the best operational protocol and operation unit for scaling-up, with regard to the efficiency on yield, sustainability, and environmental impact as determined by using different green metric parameters, like the PMI, the Efactor, and the EcoScale tool.…”

Section: ■ Introductionmentioning

confidence: 99%

“…The conditions for the ultrasound-assistance setup were 40 °C, 70% amplitude, and 2 h reaction time, as previously reported. 28 To perform kinetic profiles, aliquots of 20 μL were withdrawn at regular intervals and suspended in 980 μL of acetonitrile/methanol/ H 2 O (35:15:50 v/v/v) for further analysis in HPLC.…”

Section: ■ Introductionmentioning

confidence: 99%

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Sustainable Setups for the Biocatalytic Production and Scale-Up of Panthenyl Monoacyl Esters under Solvent-Free Conditions

Nieto

Bernal

Villa

et al. 2023

ACS Sustainable Chem. Eng.

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A sustainable scaling-up process for the biocatalytic production of new bioactive provitamin-B 5 monoacyl esters has been demonstrated. A solvent-free reaction protocol, based on the formation of eutectic mixtures between neat substrates, renders highly efficient direct esterification of free fatty acids (i.e., from C 6 to C 18 alkyl-chain length) with panthenol catalyzed by lipase. The scale-up from 0.5 to 500 g was evaluated by means of using several reaction systems (i.e., ultrasound assistance, orbital shaking, rotary evaporator, and mechanical stirring coupled to vacuum). For all reactor systems, the yield in panthenyl monoacyl esters was improved by increasing the length of the alkyl chain of the fatty acid (i.e., from 63% yield for panthenyl butyrate to 83% yield for panthenyl myristate). The best results (87−95% product yield, for all cases) were obtained upon a scale-up (50−500 g size) and when a vacuum system was coupled to the biocatalytic reaction unit. Under the optimized conditions, a 5-fold reduction of the amount of biocatalysts with respect to reactors without vacuum was achieved. The recovery and reuse of the immobilized enzyme for five operation cycles were also demonstrated. Finally, different metrics have been applied to assess the greenness of the solvent-free biocatalytic synthesis of panthenyl monoesters here reported.

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Mechanoenzymatic Reactions – Challenges and Perspectives

Hollenbach,

Ochsenreither

2023

ChemCatChem

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Mechanoenzymology has emerged as a recent topic in modern research and process design in the transition towards green chemistry. Due to the almost solvent‐free character of mechanoenzymatic reactions solvent usage is considerably reduced and waste can be avoided. Moreover, mechanoenzymatic reactions show highly promising space‐time yields and conversions, however, are still less investigated than their chemical counterparts. The selectivity of enzymes is an important feature for designing green processes and avoiding formation of by‐products. In this review, different mechanoenzymatic strategies are pointed out, involving the most common applied devices, i.e., shaker ball mills, planetary ball mills and twin‐screw extruders. Their compatibility with upscaling and continuous processes is discussed and reusability of enzymes in the different mechanoenzymatic processes is evaluated. In addition, learnings from mechanochemistry are presented and their potential benefits for mechanoenzymology are outlined.

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Ultrasound-assisted enzymatic synthesis of xylitol fatty acid esters in solvent-free conditions

Abstract: Graphical abstract

Cited by 18 publications

References 30 publications

Novel Lipase Reactor based on Discontinuous Interfaces in Hydrogel-Organogel Hybrid Gel: A Preliminary Exploration

Novel Lipase Reactor based on Discontinuous Interfaces in Hydrogel-Organogel Hybrid Gel: A Preliminary Exploration

Sustainable Setups for the Biocatalytic Production and Scale-Up of Panthenyl Monoacyl Esters under Solvent-Free Conditions

Mechanoenzymatic Reactions – Challenges and Perspectives

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