Exceptionally active and reusable nanobiocatalyst comprising lipase non-covalently immobilized on multi-wall carbon nanotubes for the synthesis of diester plasticizers

Szelwicka, Anna; Boncel, Sławomir; Jurczyk, Sebastian; Chrobok, Anna

doi:10.1016/j.apcata.2019.01.030

Cited by 28 publications

(15 citation statements)

References 20 publications

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“…Nowadays, the progress achievable by applying hydrophobic MWCNTs for the immobilization of CALB is indisputable [ 20 ]. For instance, our previous studies have proved the high stability of MWCNTs-CALB hybrids (pristine and polytetrafluoroethylene-modified MWCNTs) with a consecutive high activity and stability in organic synthesis in both batch and flow systems [ 25 , 26 , 27 , 28 , 29 ].…”

Section: Introductionmentioning

confidence: 99%

“…It is worth underlining that the use of a commercially available biocatalytic system, i.e., Novozyme 435, was proven to be poorly stable in the recycle tests due to thermal and mechanical deterioration, occasionally even after the first reaction [ 25 , 26 , 27 , 28 , 29 ]. Further, the main advantage of SILP materials is to minimize the amount of ILs compared to the catalysis in bulk.…”

Section: Introductionmentioning

confidence: 99%

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Outperformance in Acrylation: Supported D-Glucose-Based Ionic Liquid Phase on MWCNTs for Immobilized Lipase B from Candida antarctica as Catalytic System

et al. 2021

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This study presents a highly efficient method of a synthesis of n-butyl acrylate via esterification of acrylic acid and n-butanol in the presence of supported ionic liquid phase (SILP) biocatalyst consisting of the lipase B from Candida antarctica (CALB) and multi-walled carbon nanotubes (MWCNTs) modified by D-glucose-based ionic liquids. Favorable reaction conditions (acrylic acid: n-butanol molar ratio 1:2, cyclohexane as a solvent, biocatalyst 0.150 g per 1 mmol of acrylic acid, temperature 25 °C) allowed the achievement of a 99% yield of n-butyl acrylate in 24 h. Screening of various ionic liquids showed that the most promising result was obtained if N-(6-deoxy-1-O-methoxy-α-D-glucopyranosyl)-N,N,N-trimethylammonium bis-(trifluoromethylsulfonyl)imide ([N(CH3)3GlcOCH3][N(Tf)2]) was selected in order to modify the outer surface of MWCNTs. The final SILP biocatalyst–CNTs-[N(CH3)3GlcOCH3][N(Tf)2]-CALB contained 1.8 wt.% of IL and 4.2 wt.% of CALB. Application of the SILP biocatalyst led to the enhanced activity of CALB in comparison with the biocatalyst prepared via physical adsorption of CALB onto MWCNTs (CNTs-CALB), as well as with commercially available Novozyme 435. Thus, the crucial role of IL in the stabilization of biocatalysts was clearly demonstrated. In addition, a significant stability of the developed biocatalytic system was confirmed (three runs with a yield of ester over 90%).

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Outperformance in Acrylation: Supported D-Glucose-Based Ionic Liquid Phase on MWCNTs for Immobilized Lipase B from Candida antarctica as Catalytic System

et al. 2021

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“…Immobilization was performed according to a literature method [ 9 , 38 , 40 ]. A native lipase (7.5 g), a hybrid MWCNT-PTFE support (1.0 g) and water (30 mL) (pH = 6.20–6.30) was introduced into a 100-mL round bottom flask and shaken in a thermostatic shaker (250 rpm) at 20 °C for 3 h. Then, the solid was filtered off under vacuum and washed 4 times with water (50 mL).…”

Section: Methodsmentioning

confidence: 99%

“…The scrupulous analysis of the up-to-date literature data—revealing medium yields of esters accompanied by rather moderate stability of the biocatalytic systems and extended esterification times—encouraged us to demonstrate the potential of the active solid carrier for CALB. In our previous studies, a highly active nanobiocatalyst from CALB non-covalently immobilized on multi-walled carbon nanotubes (MWCNTs) for the Baeyer–Villiger synthesis of lactones was presented [ 9 , 38 , 39 , 40 ]. The direct physical adsorption method was based on hydrophobic, electrostatic and hydrogen bonding interactions between MWCNTs and the enzyme.…”

Section: Introductionmentioning

confidence: 99%

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PTFE-Carbon Nanotubes and Lipase B from Candida antarctica—Long-Lasting Marriage for Ultra-Fast and Fully Selective Synthesis of Levulinate Esters

Szelwicka

Siewniak

Kolanowska³

et al. 2021

Materials

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An effective method for levulinic acid esters synthesis by the enzymatic Fischer esterification of levulinic acid using a lipase B from Candida antarctica (CALB) immobilized on the advanced material consisting of multi-wall carbon nanotubes (MWCNTs) and a hydrophobic polymer—polytetrafluoroethylene (Teflon, PTFE)—as a heterogeneous biocatalyst, was developed. An active phase of the biocatalyst was obtained by immobilization via interfacial activation on the surface of the hybrid material MWCNTs/PTFE (immobilization yield: 6%, activity of CALB: 5000 U∙L∙kg−1, enzyme loading: 22.5 wt.%). The catalytic activity of the obtained biocatalyst and the effects of the selected reaction parameters, including the agitation speed, the amount of PTFE in the CALB/MWCNT-PTFE biocatalyst, the amount of CALB/MWCNT-PTFE, the type of organic solvent, n-butanol excess, were tested in the esterification of levulinic acid by n-butanol. The results showed that the use of a two-fold excess of levulinic acid to n-butanol, 22.5 wt.% of CALB on MWCNT-PTFE (0.10 wt.%) and cyclohexane as a solvent at 20 °C allowed one to obtain n-butyl levulinate with a high yield (99%) and selectivity (>99%) after 45 min. The catalyst retained its activity and stability after three cycles, and then started to lose activity until dropping to a 69% yield of ester in the sixth reaction run. The presented method has opened the new possibilities for environmentally friendly synthesis of levulinate esters.

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A Review on the Use of Bio/Nanostructured Heterogeneous Catalysts in Biodiesel Production

Santos¹,

Puna

Gomes

et al. 2021

Nano‐ and Biocatalysts for Biodiesel Production

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Exceptionally active and reusable nanobiocatalyst comprising lipase non-covalently immobilized on multi-wall carbon nanotubes for the synthesis of diester plasticizers

Cited by 28 publications

References 20 publications

Outperformance in Acrylation: Supported D-Glucose-Based Ionic Liquid Phase on MWCNTs for Immobilized Lipase B from Candida antarctica as Catalytic System

Outperformance in Acrylation: Supported D-Glucose-Based Ionic Liquid Phase on MWCNTs for Immobilized Lipase B from Candida antarctica as Catalytic System

PTFE-Carbon Nanotubes and Lipase B from Candida antarctica—Long-Lasting Marriage for Ultra-Fast and Fully Selective Synthesis of Levulinate Esters

A Review on the Use of Bio/Nanostructured Heterogeneous Catalysts in Biodiesel Production

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