53226-35-0

Upstream product

• 124-38-9 carbon dioxide 
• 141-43-5 ethanolamine 
• 64-18-6 formic acid 

Downstream Products

• 1357398-22-1 CH₂O₂*C₁₄H₁₆NOP 

Relevant academic research and scientific papers

Hydroxyl ammonium ionic liquids as media for biocatalytic oxidations

In this work, neoteric and biodegradable ionic liquids (ILs) based on various hydroxyl ammonium cations and formic acid anions have been used as media for biocatalytic oxidoreductions catalyzed by different metalloproteins. The effect of these ILs on the biocatalytic behavior and structure of solubilized enzymes was investigated using cytochrome c (cyt c) as a model protein. The use of IL-based media enhances the tolerance of cyt c against the denaturing effect of H2O2 and increases (up to 20 fold) its catalytic efficiency compared to that observed in buffer. This beneficial effect strongly correlates with the concentration of ILs used, as well as the chaotropicity of their cations. UV-vis, circular dichroism and Fourier transform infrared (FT-IR) spectroscopic studies indicated that, the effect of ILs on the catalytic behavior of cyt c could be correlated with slight structural changes on the protein molecule and/or perturbations of the heme microenvironment. The use of hydroxyl ammonium-based ILs as reaction media increased (up to 4-fold) the decolorization activity of cyt c. All ILs used were recycled and successfully reused three times indicating the potential application of these novel ILs as environmentally friendly media for biocatalytic processes of industrial interest.

Green synthesis of bis-(β-dicarbonyl)-methane derivatives and biological evaluation as putative anticandidial agents

In this work the effectiveness of two different reaction media, an Ionic Liquid (IL) and a Deep Eutectic Solvent (DES), as greener, alternative solvents for the synthesis of bioactive bis-(β-dicarbonyl)-methane derivatives is examined. A domino Knoevenage

Oxidized Lignin Depolymerization using Formate Ionic Liquid as Catalyst and Solvent

Lignin has been widely studied as a sustainable source of renewable materials, particularly aromatic feedstock chemicals, which are in great and increasing need in the world. Lignin oxidation and depolymerization presents a promising approach to functionalized phenolic products. In this work, a novel oxidative degradation of lignin using a formate ionic liquid was investigated resulting in ethyl acetate soluble and also water-soluble depolymerized lignin products. The β-O-4 bonds in lignin were oxidized and then depolymerized by a recyclable ionic liquid, 2-hydroxy ethylammonium formate. 2-Hydroxy ethylammonium formate, which could dissolve lignin acting as a solvent, was found to also catalyze the depolymerization of the oxidized lignin. The lignin depolymerization products were characterized.

The synthesis of multiphasic ionic liquid-coated Pt/Al2O 3 catalysts: The selective synchronous hydrogenation of CC and CO bonds and the modeling of the ionic liquid and solvent effects

Various ionic liquids (ILs) and their mixtures were coated on the Pt/Al2O3 catalyst and the resulting IL-coated catalysts were used in the synchronous hydrogenation of cyclohexene and acetone. The rate constant (k) and selectivity (S) toward CO hydrogenation were determined for several catalysts in various solvents. The solvatochromic parameters (E TN, normalized polarity parameter; π*, dipolarity-polarizability; β, hydrogen-bond acceptor basicity; α, hydrogen-bond donor acidity) were determined for the used ILs and solvents and the obtained selectivities were modeled based on the solvatochromic parameters of the IL layer and bulk solvent while using the Multiparameter Linear Regression (MLR) method for the first time. Selectivity toward the CO bond increases by increasing the percentage of 2-hydroxy ethylammonium formate (HEAF) in the IL layer and decreasing the polarity of the solvents. The single-parameter correlations of lnS versus π* presented the best correlation for the prepared catalysts in all solvents. The Royal Society of Chemistry.

Synthesis and structure-properties relationship studies of biodegradable hydroxylammonium-based protic ionic liquids

In this work sixteen hydroxyl ammonium Protic Ionic Liquids derived from a proton transfer reaction between four different substituted amines and four different low molecular weight aliphatic and alicyclic carboxylic acids have been synthesized. The synthesized PILs were structurally characterized by NMR and FT-IR spectroscopy whereas two of their more important physicochemical properties namely viscosity and glass transition temperature (Tg) were evaluated. The effect of alkyl chain length and substitution on the anionic and cationic component of the PILs scaffold has been discussed for the studied properties. It seems that Tg values are mainly affected by the carboxylate anion structure whereas viscosity is controlled mainly by the structural features of the cationic part of the PILs. In order to estimate their environmental impact and reinforce their “green” character, biodegradation studies, as well as toxicity evaluation experiments have also been conducted. The synthesized PILs can be confidently labelled as green considering that they are not toxic or present low toxicity to the nauplii of the brine shrimp A. salina whereas they show biodegradability levels between 41–64%, according to the manometric respirometric method which measures the biological oxygen demand (BOD5) by microorganisms in order to degrade PILs via bio-oxidation in five days.

Solvatochromic probes absorbance behavior in mixtures of 2-hydroxy ethylammonium formate with methanol, ethylene glycol and glycerol

Solute-solvent and solvent-solvent interactions were investigated for binary mixtures of an ionic liquid (IL) 2-hydroxy ethylammonium formate as with methanol, ethylene glycol and glycerol. The physicochemical properties of the solvent mixtures at 25 °C, over the whole range of mole fractions, were determined using solvatochromic probes. High normal polarity (ET N) in the alcohol-rich region confirms solute-solvent interactions in this medium. Dipolarity/polarizability (π *) show a different trend to ETN with a positive deviation from ideal behavior in IL-glycerol mixtures. However, these deviations for other solvent mixtures are insignificant. Contrary to what is observed for E TN and π*, hydrogen-bond donor (HBD) acidity and hydrogen-bond acceptor (HBA) basicity demonstrate similar trends. The applicability of the combined nearly-ideal binary solvent/Redlich-Kister (CNIBS/R-K) equation for the correlation of various parameters provides a simple computational model to correlate and/or predict various solvatochromic parameters for many binary solvent systems.

Basic ionic liquid, 2-hydroxyethylammonium formate, catalyzed one-pot synthesis of novel 2-(phenylsulfonyl)-1H-benzo[a]pyrano[2,3-c]phenazin-3-amine derivatives

A new, one-pot, efficient, and four-component condensation of 2-hydroxynaphthalene-1,4-dione, benzene-1,2-diamine, arylaldehydes and (phenylsulfonyl)acetonitrile in the presence of a reusable basic ionic liquid, 2-hydroxyethylammonium formate, as catalyst

Synthesis of renewable alkylated naphthalenes with benzaldehyde and angelica lactone

Herein, we report a new route for the synthesis of renewable alkylated naphthalenes (ANs) with benzaldehyde and angelica lactone, two platform compounds that can be derived from lignocellulose.

Cytotoxicity of protic ionic liquids towards the HaCat cell line derived from human skin

In this work we have investigated the toxicity of 10 PILs, consisting of ethyl-, ethanol-, diethanol- and triethanolammonium cations paired with nitrate, formate, acetate and glycolate anions. Their toxicity was quantified by the EC50 values of each of these PILs towards HaCat cells, which are derived from human skin cells. Additional salts and solvents were used for comparison including DMSO, choline chloride, potassium nitrate, sodium acetate and ethanol to distinguish if the toxicity changes were due to ionicity, short chain amphiphilic behaviour, or specific ion effects. The toxicity followed the general trend of choline chloride acetate containing PILs DMSO sodium acetate ethanol nitrate containing PILs or salt. Ethanolammonium acetate and ethylammonium acetate were identified as having the lowest toxicities of the PILs, being slightly more toxic than choline chloride or DMSO. Overall the toxicity was found to be highly dependent on the cation and anion combination, with the anion having a stronger affect. It was evident that the PILs can be tailored to vary their toxicities, and this is expected to be dependent on which cell lines are used.

Hydroxyl alkyl ammonium ionic liquid assisted green and one-pot regioselective access to functionalized pyrazolodihydropyridine core and their pharmacological evaluation

Herein our team explored a promising synthetic trail to Functionalized pyrazolodihydropyridine core using hydroxyl alkyl ammonium ionic liquid via one-pot fusion of 3-methyl-1-phenyl-1H-pyrazole-5-amine, different heterocyclic aldehydes and 1, 3-Cyclic diones. The aimed compounds were obtained by Domino-Knoevenagel condensation and Michael addition followed by cyclization. The reaction transformation involves the formation of two C–C and one C–N bond formation. The perspective of the present work is selectively approached to Functionalized pyrazolodihydropyridine core excluding other potential parallel reactions under environmentally benign reaction condition. The present protocol show features such as the low E-factor, ambiphilic behavior of ionic liquid during reaction transformation, scale-up to a multigram scale, reusability of the ionic liquid, mild reaction condition, and produce water as a byproduct. All newly derived compounds were evaluated for their in vitro biological activities. In preliminary biological studies compound, 4c showed better potency than the standard drug ampicillin against Gram-negative bacteria (E. coli); the compound 4i exhibited outstanding activity against S. aeruginosa which is far better than ampicillin, chloramphenicol, and ciprofloxacin. The compound 4m was found more potent against C. albicans, than that of griseofulvin and show equipotency to nystatin whereas, in preliminary antitubercular screening, compound 4o was exhibited more potency than rifampicin. Noteworthy compounds 4f and 4i were found most active in antiproliferative screening.