1-Butyl-2,3-dimethylimidazolium tetrafluoroborate: the most desirable ionic liquid solvent for recycling use of enzyme in lipase-catalyzed transesterification using vinyl acetate as acyl donor

Itoh, Toshiyuki; Nishimura, Yoshihito; Ouchi, Nozomi; Hayase, Shuichi

doi:10.1016/s1381-1177(03)00147-4

Cited by 108 publications

(45 citation statements)

References 20 publications

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“…Novozym 435 is an immobilized lipase from Candida antarctica B on a macroporous acrylic support and can facilitate the recycling and reusing of the enzyme in ILs. Additionally, no accumulation of acetaldehyde oligomer was observed by NMR analysis when the enzymatic resolution process was conducted in the IL with vinyl acetate being the acyl donor, which is very similar to the result described by Itoh et al 41 Accordingly, it is possible to use the immobilized lipase repeatedly for many times while still maintaining its fairly high activity and enantioselectivity. The lipase Novozym 435 was consequently selected as the catalyst for efficient kinetic resolution of (R,S)-1-TMSE through enzymatic enantioselective acylation in ILs.…”

Section: Resultssupporting

confidence: 85%

Efficient kinetic resolution of (R,S)‐1‐trimethylsilylethanol via lipase‐mediated enantioselective acylation in ionic liquids

Lou

Zong

2006

Chirality

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Efficient enantioselective acylation of (R,S)-1-trimethylsilylethanol {(R,S)-1-TMSE} with vinyl acetate catalyzed by immobilized lipase from Candida antarctica B (i.e., Novozym 435) was successfully conducted in ionic liquids (ILs). A remarkable enhancement in the initial rate and the enantioselectivity of the acylation was observed by using ILs as the reaction media when compared to the organic solvents tested. Also, the activity, enantioselectivity, and thermostability of Novozym 435 increased with increasing hydrophobicity of ILs. Of the six ILs examined, the IL C4MIm.PF6 gave the fastest initial rate and the highest enantioselectivity, and was consequently chosen as the favorable medium for the reaction. The optimal molar ratio of vinyl acetate to (R,S)-1-TMSE, water activity, and reaction temperature range were 4:1, 0.75, and 40 -50 degrees C, respectively, under which the initial rate and the enantioselectivity (E value) were 27.6 mM/h and 149, respectively. After a reaction time of 6 h, the ee of the remaining (S)-1-TMSE reached 97.1% at the substrate conversion of 50.7%. Additionally, Novozym 435 was effectively recycled and reused in C4MIm.PF6 for five consecutive runs without substantial lose in activity and enantioselectivity. The preparative scale kinetic resolution of (R,S)-1-TMSE in C4MIm.PF6 is shown to be very promising and useful for the industrial production of enantiopure (S)-1-TMSE.

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Section: Resultssupporting

confidence: 85%

Efficient kinetic resolution of (R,S)‐1‐trimethylsilylethanol via lipase‐mediated enantioselective acylation in ionic liquids

Lou

Zong

2006

Chirality

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“…Our results are in accordance with the work of Itoh et al [35], where in repeated recycling of the enzyme in 1-butyl-3-methylimidazolium hexafluorophosphate, [bmim] [PF 6 ], monophasic transesterification reaction in a batch mode was proven to be possible, although the reaction rate gradually dropped with repetition of the reaction process when vinyl acetate was used as acyl donor. Recyclability of ionic liquid together with the immobilized CaLB (Novozym 435) in isoamyl acetate synthesis from acetic acid and isoamyl alcohol was tested by Feher et al [36], and their results revealed the same level of lipase B activity within 10 cycles.…”

Section: Biotransformation With Reused Enzyme and Ionic Liquidsupporting

confidence: 92%

“…Because ionic liquids are still very expensive, processes involving these solvents are competitive only if the ionic liquid phase is recycled and reused as many times as possible [22]. Such protocols were already tested in several batch processes [14,22,23,35,36], while, to the best of our knowledge, the reuse of solvents within microfluidic devices employing biocatalysts has not yet been described.…”

Section: Introductionmentioning

confidence: 99%

Integrated lipase-catalyzed isoamyl acetate synthesis in a miniaturized system with enzyme and ionic liquid recycle

Novak

Žnidaršič–Plazl

2013

Green Processing and Synthesis

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Isoamyl acetate synthesis employing aqueous Candida antarctica lipase B (CaLB) solution was performed in a two-phase solvent system comprising hydrophilic ionic liquid 1-butyl-3-methylpyridinium dicyanamide and n-heptane. An X-junction glass microfluidic chip was used to obtain uniform microdroplets of n-heptane within a continuous phase of ionic liquid with dissolved enzyme and reactants, namely, isoamyl alcohol and acetic anhydride. A developed flow pattern resulted in a very large specific interfacial area for the reaction with amphiphilic CaLB and simultaneous extraction of isoamyl acetate in n-heptane. Biotransformation was performed within a continuously operated microfluidic system consisting of an X-junction chip and a silanized tube of a submillimeter diameter, which was further integrated with a microseparator based on a hydrophobic membrane. Efficient separation of n-heptane with product from ionic liquid phase containing enzyme and remaining substrates and products was achieved, enabling reuse of CaLB together with ionic liquid phase. More than 80% of productivity was preserved in each of the eight consecutive biotransformations within the integrated microfluidic system with reused lipase B in the ionic liquid phase. Subsequent ionic liquid regeneration accomplished by vacuum distillation enabled efficient reuse of this solvent in esterification with fresh enzyme.

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“…The potential of these "green solvents" lies in their unique physicochemical properties, such as non-volatility, nonflammability, thermal stability and good solubility for many polar and less polar organic compounds (Jain et al, 2005;Wilkes, 2004;Itoh et al, 2003;Van Rantwick et al, 2003). Probably the most promising advantage of the use of ionic liquids is their potential application in food, pharmaceutical and cosmetic preparations due to their reduced toxicity (Jarstoff et al, 2003).…”

Section: Solvent Referencementioning

confidence: 99%

Enzyme-Mediated Preparation of Flavonoid Esters and Their Applications

Viskupičová¹,

Ondrejovič²,

Maliar³

2012

Biochemistry

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1-Butyl-2,3-dimethylimidazolium tetrafluoroborate: the most desirable ionic liquid solvent for recycling use of enzyme in lipase-catalyzed transesterification using vinyl acetate as acyl donor

Cited by 108 publications

References 20 publications

Efficient kinetic resolution of (R,S)‐1‐trimethylsilylethanol via lipase‐mediated enantioselective acylation in ionic liquids

Efficient kinetic resolution of (R,S)‐1‐trimethylsilylethanol via lipase‐mediated enantioselective acylation in ionic liquids

Integrated lipase-catalyzed isoamyl acetate synthesis in a miniaturized system with enzyme and ionic liquid recycle

Enzyme-Mediated Preparation of Flavonoid Esters and Their Applications

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