Microwave assisted enzymatic esterification of lactic acid and ethanol in phosphonium type ionic liquids as co-solvents

Major, Brigitta; Kelemen-Horváth, I.; Csanádi, Zs.; Bélafi–Bakó, Katalin; Gubicza, L.

doi:10.1039/b820575b

Cited by 34 publications

(14 citation statements)

References 19 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…However, problems caused by these catalysts are not in conformity with the requirements for sustainable development, e.g., equipment corrosion, environmental pollution, undesirable side reactions, plaguy catalyst recovery and reuse. To avoid these drawbacks, heterogeneous catalysts such as solid superacids, [2][3][4][5] heteropolyacids, 6 zeolites, 7-9 resins 10 and enzymes [11][12][13][14] have been employed for esterification. Unfortunately, limited applications were found for these solid catalysts due to their disadvantages such as low activity, easy deactivation, formidable separation and recovery and so on.…”

Section: Introductionmentioning

confidence: 99%

Syntheses of novel halogen-free Brønsted–Lewis acidic ionic liquid catalysts and their applications for synthesis of methyl caprylate

Han

Hung

et al. 2015

Green Chem.

View full text Add to dashboard Cite

show abstract

Section: Introductionmentioning

confidence: 99%

Syntheses of novel halogen-free Brønsted–Lewis acidic ionic liquid catalysts and their applications for synthesis of methyl caprylate

Han

Hung

et al. 2015

Green Chem.

View full text Add to dashboard Cite

show abstract

“…25 Although most studies are focused on the enzymes catalytic activity in presence of aromatic ILs, particularly imidazolium-based, noncyclic and nonaromatic cations, such as phosphonium-based ILs, could lead to relevant improvements and contribute to the design of efficient biotechnological processes. [26][27][28] Imidazolium-based ILs have been applied as solvents in biocatalytic processes involving reactions such as transesterification and hydrolysis. [29][30][31][32][33][34] Mai et al 29 (1-butyl-3-methylimidazolium triflate:1-butyl-3-methylimidazolium bistrisflamide).…”

mentioning

confidence: 99%

Effects of phosphonium‐based ionic liquids on the lipase activity evaluated by experimental results and molecular docking

Barbosa

Freire

Souza

et al. 2019

Biotechnology Progress

View full text Add to dashboard Cite

In this work, the effect of several phosphonium‐based ionic liquids (ILs) on the activity of lipase from Burkholderia cepacia (BCL) was evaluated by experimental assays and molecular docking. ILs comprising different cations ([P4444]+, [P444(14)]+, [P666(14)]+) and anions (Cl−, Br−, [Deca]−, [Phosp]−, [NTf2]−) were investigated to appraise the individual roles of IL ions on the BCL activity. From the activity assays, it was found that an increase in the cation alkyl chain length leads to a decrease on the BCL enzymatic activity. ILs with the anions [Phosp]− and [NTf2]− increase the BCL activity, while the remaining [P666(14)]‐based ILs with the Cl−, Br−, and [Deca]− anions display a negative effect on the BCL activity. The highest activity of BCL was identified with the IL [P666(14)][NTf2] (increase in the enzymatic activity of BCL by 61% at 0.055 mol·L−1). According to the interactions determined by molecular docking, IL cations preferentially interact with the Leu17 residue (amino acid present in the BCL oxyanion hole). The anion [Deca]− has a higher binding affinity compared to Cl− and Br−, and mainly interacts by hydrogen‐bonding with Ser87, an amino acid residue which constitutes the catalytic triad of BCL. The anions [Phosp]− and [NTf2]− have high binding energies (−6.2 and −5.6 kcal·mol−1, respectively) with BCL, and preferentially interact with the side chain amino acids of the enzyme and not with residues of the active site. Furthermore, FTIR analysis of the protein secondary structure show that ILs that lead to a decrease on the α‐helix content result in a higher BCL activity, which may be derived from an easier access of the substrate to the BCL active site.

show abstract

“…57 The efficiency of microwaves has already been demonstrated in different systems involving enzymes. 57−64 Therefore, as esterification has polar transition states, 57 microwave irradiation may greatly decrease the energy of the transition state, thus leading to quicker reactions and higher conversions.…”

Section: ■ Introductionmentioning

confidence: 99%

Bioinspired Enzymatic Synthesis of Terpenoid-Based (Meth)acrylic Monomers: A Solvent-, Metal-, Amino-, and Halogen-Free Approach

Castagnet

Aguirre

Asúa

et al. 2020

ACS Sustainable Chem. Eng.

View full text Add to dashboard Cite

In an attempt to pave the way toward the substitution of petroleum-based monomers for monomers from sustainable and renewable resources, this work investigates the synthesis of a portfolio of new (meth)acrylic monomers using terpenoids as raw materials that can be conveniently extracted from wood waste and citrus fruits. The synthetic process is based on the enzymatic catalysis of the esterification of terpenoids and is solvent-, metal-, amino-, and halogen-free, overcoming the limitations of the common esterification techniques. The effect of employing microwaves in combination with the enzyme and the effect of the acyl donor choice [(meth)acrylic acids vs (meth)acrylic anhydrides] were studied. The process yielded complete conversion and then high-purity monomers with a variety of structures that would allow them to substitute many of the most commonly used petrochemical (meth)acrylic monomers.

show abstract

Microwave assisted enzymatic esterification of lactic acid and ethanol in phosphonium type ionic liquids as co-solvents

Cited by 34 publications

References 19 publications

Syntheses of novel halogen-free Brønsted–Lewis acidic ionic liquid catalysts and their applications for synthesis of methyl caprylate

Syntheses of novel halogen-free Brønsted–Lewis acidic ionic liquid catalysts and their applications for synthesis of methyl caprylate

Effects of phosphonium‐based ionic liquids on the lipase activity evaluated by experimental results and molecular docking

Bioinspired Enzymatic Synthesis of Terpenoid-Based (Meth)acrylic Monomers: A Solvent-, Metal-, Amino-, and Halogen-Free Approach

Contact Info

Product

Resources

About