Browse
Submit Data
Databases
API
Help

Dataset Information

6 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Efficient Approach for the Tritylation of Alcohols Using Recyclable Lewis Acid-Based Ionic Liquid (EMIM·AlCl₄).

ABSTRACT: A new efficient approach has been reported for the tritylation of primary alcohols over secondary alcohols using triphenyl methyl alcohol and 4-monomethoxyl trityl alcohols in the presence of imidazolium-based ionic liquid 1-ethyl-3-methylimidazolium tetrachloroaluminate as catalyst. At room temperature, 5 mol % of catalyst in dichloromethane and acetonitrile solvent has been shown to be excellent for the tritylation of benzyl alcohol and various other alcohols The method was compatible with Fmoc/acetyl protecting group of amino and tert-butyldiphenylsilyl ether protecting group of alcohol. Moreover, the catalyst was reused for three to four catalytic cycles with little loss of catalytic activity. Excellent yields, reusability, chemoselectivity, and easy workup are advantages of this protocol.

SUBMITTER: Chaubey SA

PROVIDER: S-EPMC6644558 | biostudies-literature | 2018 Aug

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

Efficient Approach for the Tritylation of Alcohols Using Recyclable Lewis Acid-Based Ionic Liquid (EMIM·AlCl4).

Chaubey Snehkrishn A SA Mishra Jyoti S JS Mishra Roli R

ACS omega 20180821 8

A new efficient approach has been reported for the tritylation of primary alcohols over secondary alcohols using triphenyl methyl alcohol and 4-monomethoxyl trityl alcohols in the presence of imidazolium-based ionic liquid 1-ethyl-3-methylimidazolium tetrachloroaluminate as catalyst. At room temperature, 5 mol % of catalyst in dichloromethane and acetonitrile solvent has been shown to be excellent for the tritylation of benzyl alcohol and various other alcohols The method was compatible with Fmo ...[more]

PMID: 31459091

Similar Datasets

Tunable Aryl Imidazolium Recyclable Ionic Liquid with Dual Bronsted-Lewis Acid as Green Catalyst for Friedel-Crafts Acylation and Thioesterification.

Project description:Unique tunable aryl imidazolium ionic liquids successfully catalyzed Friedel-Crafts acylation and thioesterification in sealed tubes. These reactions can form a C-C bond and a C-S bond with high atom economy. Ionic liquids exhibited high activity and catalyzed essential reactions with good to excellent yields while retaining their catalytic activities for recycling.

| S-EPMC7024267 | biostudies-literature

Highly efficient enantioselective liquid-liquid extraction of 1,2-amino-alcohols using SPINOL based phosphoric acid hosts.

Project description:Access to enantiopure compounds on large scale in an environmentally friendly and cost-efficient manner remains one of the greatest challenges in chemistry. Resolution of racemates using enantioselective liquid-liquid extraction has great potential to meet that challenge. However, a relatively feeble understanding of the chemical principles and physical properties behind this technique has hampered the development of hosts possessing sufficient resolving power for their application to large scale processes. Herein we present, employing the previously untested SPINOL based phosphoric acids host family, an in depths study of the parameters affecting the efficiency of the resolution of amino-alcohols in the optic of further understanding the core principles behind ELLE. We have systematically investigated the dependencies of the enantioselection by parameters such as the choice of solvent, the temperature, as well as the pH and bring to light many previously unsuspected and highly intriguing interactions. Furthermore, utilizing these new insights to our advantage, we developed novel, highly efficient, extraction and resolving protocols which provide remarkable levels of enantioselectivity. It was shown that the extraction is catalytic in host by demonstrating transport in a U-tube and finally it was demonstrated how the solvent dependency could be exploited in an unprecedented triphasic resolution system.

| S-EPMC5628577 | biostudies-literature

Data for the synthesis of β-oxopropylcarbamates from propargylic alcohols, secondary amines and CO2 catalyzed by a recyclable AgBr/ionic liquid system under ambient pressure.

Project description:Data presented here are related with the research article entitled "Synthesis of ß -oxopropylcarbamates in a recyclable AgBr/ionic liquid catalytic system: An efficient assembly of CO2 under ambient pressure" (Song et al., 2018) [1]. In this data article, the general synthetic procedures of ß-oxopropylcarbamates through the three-component reaction of propargylic alcohols, secondary amines and carbon dioxide (CO2) catalyzed by a recyclable AgBr/ionic liquid (IL) system under mild pressure are described. Furthermore, the process for recycling the catalysts is supplied as well. Specifically, the investigative data for the temperature, amount of ILs, reaction time as well as the state of silver in the system are also reported. Finally, all the target products are confirmed by 1H NMR, 13C NMR, and high-resolution mass spectroscopy (HR-MS).

| S-EPMC6148840 | biostudies-literature

New nano-Fe3O4-supported Lewis acidic ionic liquid as a highly effective and recyclable catalyst for the preparation of benzoxanthenes and pyrroles under solvent-free sonication.

Project description:A novel magnetic nanomaterial-immobilized Lewis acidic ionic liquid was successfully synthesized by the covalent embedding of 3-(3-(trimethoxysilyl)propyl)-1H-imidazol-3-ium chlorozincate (ii) ionic liquid to the surface of Fe3O4 nanoparticles. The material was then characterized by FT-IR, SEM, TEM, TGA, ICP-OES, Raman, and EDS. Its performance as a new-generation Lewis acidic catalyst was also examined on the ultrasound-mediated synthesis of benzoxanthenes and pyrroles. Upon completion, the catalyst was simply recovered by an external magnet for multiple reuses without significant lessening of catalytic performance.

| S-EPMC9087937 | biostudies-literature

Task-specific ionic liquid and CO2-cocatalysed efficient hydration of propargylic alcohols to α-hydroxy ketones.

Project description:The hydration of propargylic alcohols is a green route to synthesize α-hydroxy ketones. Herein a CO2-reactive ionic liquid (IL), [Bu4P][Im], was found to display high performance for catalyzing the hydration of propargylic alcohols in the presence of atmospheric CO2, and a series of propargylic alcohols could be converted into the corresponding α-hydroxy ketones in good to excellent yields. In the IL/CO2 reaction system, CO2 served as a cocatalyst by forming α-alkylidene cyclic carbonates with propargylic alcohols, and was released via the rapid hydrolysis of the carbonates catalysed by the IL. This is the first example of the efficient hydration of propargylic alcohols under metal-free conditions.

| S-EPMC5645775 | biostudies-literature

Highly efficient electrochemical reduction of CO2 to CH4 in an ionic liquid using a metal-organic framework cathode.

Project description:Highly efficient electrochemical reduction of CO2 to CH4 is of great importance, but is challenging. Herein, Zn-1,3,5-benzenetricarboxylic acid metal-organic frameworks (Zn-BTC MOFs) deposited on carbon paper (CP) were used as cathodes in electrochemical reduction of CO2 using ionic liquids (ILs) as the electrolytes, which was the first work on combination of a MOF electrode and an pure IL electrolyte in the electrochemical reduction of CO2. It was found that the efficiency of the reaction depended strongly on the morphology of the Zn-MOFs. Compared with the commonly used metal electrodes, the electrochemical reaction showed much higher selectivity to CH4 and current density, and the overpotentials for CH4 is much lower. The excellent combination of the MOF cathodes and ILs opens a way for reduction of CO2 to CH4 effectively.

| S-EPMC5952524 | biostudies-literature

Combined Superbase Ionic Liquid Approach to Separate CO2 from Flue Gas.

Project description:Superbase ionic liquids (ILs) with a trihexyltetradecylphosphonium cation and a benzimidazolide ([P66614][Benzim]) or tetrazolide ([P66614][Tetz]) anion were investigated in a dual-IL system allowing the selective capture and separation of CO2 and SO2, respectively, under realistic gas concentrations. The results show that [P66614][Tetz] is capable of efficiently capturing SO2 in preference to CO2 and thus, in a stepwise separation process, protects [P66614][Benzim] from the negative effects of the highly acidic contaminant. This results in [P66614][Benzim] maintaining >53% of its original CO2 uptake capacity after 30 absorption/desorption cycles in comparison to the 89% decrease observed after 11 cycles when [P66614][Tetz] was not present. Characterization of the ILs post exposure revealed that small amounts of SO2 were irreversibly absorbed to the [Benzim]- anion responsible for the decrease in CO2 capacity. While optimization of this dual-IL system is required, this feasibility study demonstrates that [P66614][Tetz] is a suitable sorbent for reversibly capturing SO2 and significantly extending the lifetime of [P66614][Benzim] for CO2 uptake.

| S-EPMC9326967 | biostudies-literature

Improved extraction of fluoroquinolones with recyclable ionic-liquid-based aqueous biphasic systems.

Project description:In the past few years, the improvement of advanced analytical tools allowed to confirm the presence of trace amounts of metabolized and unchanged active pharmaceutical ingredients (APIs) in wastewater treatment plants (WWTPs) as well as in freshwater surfaces. It is known that the continuous contact with APIs, even at very low concentrations (ng L-1-μg L-1), leads to serious human health problems. In this context, this work shows the feasibility of using ionic-liquid-based aqueous biphasic systems (IL-based ABS) in the extraction of quinolones present in aqueous media. In particular, ABS composed of imidazolium- and phosphonium-based ILs and aluminium-based salts (already used in water treatment plants) were evaluated in one-step extractions of six fluoroquinolones (FQs), namely ciprofloxacin, enrofloxacin, moxifloxacin, norfloxacin, ofloxacin and sarafloxacin, and extraction efficiencies up to 98% were obtained. Despite the large interest devoted to IL-based ABS as extractive systems of outstanding performance, their recyclability/reusability has seldomly been studied. An efficient extraction/cleaning process of the IL-rich phase is here proposed by FQs induced precipitation. The recycling of the IL and its further reuse without losses in the ABS extractive performance for FQs were established, as confirmed by the four consecutive removal/extraction cycles evaluated. This novel recycling strategy supports IL-based ABS as sustainable and cost-efficient extraction platforms.

| S-EPMC5024758 | biostudies-literature

Phosphonium acidic ionic liquid: an efficient and recyclable homogeneous catalyst for the synthesis of 2-arylbenzoxazoles, 2-arylbenzimidazoles, and 2-arylbenzothiazoles.

Project description:A highly efficient and green strategy for the synthesis of 2-arylbenzoxazoles, 2-arylbenzimidazoles, and 2-arylbenzothiazoles catalyzed by phosphonium acidic ionic liquid has been developed via the condensation of o-aminophenol, o-phenylenediamines, and o-aminothiophenol, respectively, with aldehydes. The reaction has a good yield, the broad substrate scope, and mild condition. Triphenyl(butyl-3-sulphonyl)phosphonium toluenesulfonate catalyst was easily obtained from cheap and available starting materials through a one-pot synthesis. Its structure was identified by 1H NMR, 13C NMR, 31P NMR, and FT-IR techniques. Other properties including thermal stability and acidity were determined by TGA and Hammett acidity function method. Interestingly, the catalyst can maintain its constantly outstanding performance till the fourth recovery.

| S-EPMC9079114 | biostudies-literature

Efficient dehydration and recovery of ionic liquid after lignocellulosic processing using pervaporation.

Project description:BackgroundBiomass pretreatment using certain ionic liquids (ILs) is very efficient, generally producing a substrate that is amenable to saccharification with fermentable sugar yields approaching theoretical limits. Although promising, several challenges must be addressed before an IL pretreatment technology can become commercially viable. One of the most significant challenges is the affordable and scalable recovery and recycle of the IL itself. Pervaporation (PV) is a highly selective and scalable membrane separation process for quantitatively recovering volatile solutes or solvents directly from non-volatile solvents that could prove more versatile for IL dehydration.ResultsWe evaluated a commercially available PV system for IL dehydration and recycling as part of an integrated IL pretreatment process using 1-ethyl-3-methylimidazolium acetate ([C2C1Im][OAc]) that has been proven to be very effective as a biomass pretreatment solvent. Separation factors as high as 1500 were observed. We demonstrate that >99.9 wt% [C2C1Im][OAc] can be recovered from aqueous solution (≤20 wt% IL) and recycled five times. A preliminary technoeconomic analysis validated the promising role of PV in improving overall biorefinery process economics, especially in the case where other IL recovery technologies might lead to significant losses.ConclusionsThese findings establish the foundation for further development of PV as an effective method of recovering and recycling ILs using a commercially viable process technology.

| S-EPMC5472906 | biostudies-literature