scholarly journals Design Optimization of Deep Eutectic Solvent Composition and Separation Performance of Cyclohexane and Benzene Mixtures with Extractive Distillation

Processes ◽  
2021 ◽  
Vol 9 (10) ◽  
pp. 1706
Author(s):  
Fang Bai ◽  
Chao Hua ◽  
Yongzhi Bai ◽  
Mengying Ma
Keyword(s):  
Tetrabutylammonium Bromide ◽  
Deep Eutectic Solvent ◽  
Ternary Systems ◽  
Deep Eutectic Solvents ◽  
Extractive Distillation ◽  
Molar Concentration ◽  
Molar Ratio ◽  
Coefficient Of Determination ◽  
Separation Performance ◽  
Equilibrium Data

Deep eutectic solvents (DESs) have properties that make them suitable candidates to be used as entrainers for extractive distillation. In the previous work, it was proven that DES(1:2) (tetrabutylammonium bromide: levulinic acid, 1:2, molar ratio) can break the cyclohexane-benzene azeotrope. In the present work, the HBA and HBD ratio and molar concentration of DES were optimized to obtain a better constitute and condition of DES to be utilized in cyclohexane and benzene extractive distillation. The physical properties and structure of the prepared DESs were characterized. Vapor–liquid equilibrium data of the ternary system (benzene + cyclohexane + DESs) were also measured at atmospheric pressure. All experimental equilibrium data were correlated with Wilson, nonrandom two-liquid (NRTL), and universal quasichemical (UNIQUAC) activity coefficient models, from which the coefficient of determination (R2) of the three pseudo-ternary systems fitting was calculated. From the obtained results, the best HBA and HBD ratio in the DESs is elucidated as 1:2, the best molar concentration of DES is 0.1, and the NRTL model predicts the experimental data more accurately than the Wilson and UNIQUAC models. From the derived mechanism, the formation of stronger hydrogen bond and π–π bond interactions between DES and benzene is obtained when HBA and HBD ratio in DES is 1:2. In other conditions, the azeotrope cannot be broken, or the efficiency is low. The present work provides an environmentally friendly method to separate aromatic/aliphatic mixtures and act as a guide for further study of DESs in extractive distillation.

scholarly journals Performance of p-Toluenesulfonic Acid–Based Deep Eutectic Solvent in Denitrogenation: Computational Screening and Experimental Validation

Molecules ◽  
2020 ◽  
Vol 25 (21) ◽  
pp. 5093 ◽  
Author(s):  
Ainul F. Kamarudin ◽  
Hanee F. Hizaddin ◽  
Lahssen El-blidi ◽  
Emad Ali ◽  
Mohd A. Hashim ◽  
...  
Keyword(s):  
Deep Eutectic Solvent ◽  
Deep Eutectic Solvents ◽  
Fuel Oil ◽  
Proton Nuclear Magnetic Resonance ◽  
Molar Ratio ◽  
Nitrogen Compounds ◽  
Green Solvents ◽  
Computational Screening ◽  
Toluenesulfonic Acid ◽  
Fuel Oils

Deep eutectic solvents (DESs) are green solvents developed as an alternative to conventional organic solvents and ionic liquids to extract nitrogen compounds from fuel oil. DESs based on p-toluenesulfonic acid (PTSA) are a new solvent class still under investigation for extraction/separation. This study investigated a new DES formed from a combination of tetrabutylphosphonium bromide (TBPBr) and PTSA at a 1:1 molar ratio. Two sets of ternary liquid–liquid equilibrium experiments were performed with different feed concentrations of nitrogen compounds ranging up to 20 mol% in gasoline and diesel model fuel oils. More than 99% of quinoline was extracted from heptane and pentadecane using the DES, leaving the minutest amount of the contaminant. Selectivity was up to 11,000 for the heptane system and up to 24,000 for the pentadecane system at room temperature. The raffinate phase’s proton nuclear magnetic resonance (1H-NMR) spectroscopy and GC analysis identified a significantly small amount of quinoline. The selectivity toward quinoline was significantly high at low solute concentrations. The root-mean-square deviation between experimental data and the non-random two-liquid (NRTL) model was 1.12% and 0.31% with heptane and pentadecane, respectively. The results showed that the TBPBr/PTSADES is considerably efficient in eliminating nitrogen compounds from fuel oil.

Application of deep eutectic solvents (DES) to the denitrification of transportation fuels : insights from experimental liquid-liquid phase equilibrium data

2018 ◽  
Author(s):  
◽  
Sanele Enough Msibi
Keyword(s):  
Ethylene Glycol ◽  
Fossil Fuels ◽  
Choline Chloride ◽  
Deep Eutectic Solvent ◽  
Deep Eutectic Solvents ◽  
Distribution Coefficients ◽  
Liquid Equilibrium ◽  
Transportation Fuels ◽  
Basic Nitrogen ◽  
Equilibrium Data

Air pollution by combustion of fossil fuels is of global concern in this decade and beyond. The presence of nitrogen and sulphur impurities pose deleterious effects to refinery equipment, the environment, and human health. Therefore, many governments continue to impose stringent environmental regulations and standards on transportation fuels emissions. The current study evaluates alternate processing solutions to complement or replace the currently used processes to refine these impurities to meet the increasingly stringent fuel standards. This study evaluates the use of a class extractive solvents called Deep Eutectic Solvents (DES) for the removal of basic nitrogen impurities from refining streams by liquid-liquid extraction. This process is evinced as energy saving and environmentally friendly. The removal of pyridine and quinoline by the direct analytical method with choline chloride based deep eutectic solvent (DES) was studied. Liquid-liquid equilibrium measurements data were undertaken at 298.15 K and atmospheric pressure for n-heptane + pyridine/quinoline + [choline chloride + glycerol] DES and n-heptane + pyridine/quinoline + [choline chloride + ethylene glycol] DES systems. The obtained data were then regressed using the Non Random Two Liquid and Universal Quasi-Chemical models activity coefficient, and their mathematical reliability was validated using the Othmer Tobias and Hand correlations. A mixture of choline chloride and glycerol (DES1) showed greater extraction potential for basic nitrogen containing compounds compared to choline chloride and ethylene glycol with a distribution coefficient and selectivity of 22.7 and 2056 for pyridine, and 3.3 and 164.9 for quinoline respectively. The studied solvents showed comparability to organic and ionic liquids solvents in selectivity and distribution coefficients. The obtained liquid-liquid equilibrium data can be used in the design of a solvent extraction equipment, as phase diagrams plays an important role in separation process design.

scholarly journals Effective Extraction of Limonene and Hibaene from Hinoki (Chamaecyparis obtusa) Using Ionic Liquid and Deep Eutectic Solvent

Molecules ◽  
2021 ◽  
Vol 26 (14) ◽  
pp. 4271
Author(s):  
Rina Yasutomi ◽  
Riki Anzawa ◽  
Masamitsu Urakawa ◽  
Toyonobu Usuki
Keyword(s):  
Ionic Liquid ◽  
Organic Solvent ◽  
Essential Oils ◽  
Control Method ◽  
Deep Eutectic Solvent ◽  
Deep Eutectic Solvents ◽  
Chamaecyparis Obtusa ◽  
Molar Ratio ◽  
Gas Chromatography Mass Spectrometry ◽  
Selected Ion Monitoring

The essential oils of hinoki (Chamaecyparis obtusa) leaves have anti-bacterial, anti-fungal, and relaxation properties that are likely associated with the major components such as sabinene, α-terpinyl acetate, limonene, elemol, myrcene, and hibaene. The present study describes the use of a cellulose-dissolving ionic liquid (IL) [C2mim][(MeO)(H)PO2] and low-toxicity solvents called betaine-based deep eutectic solvents (DESs) for the efficient extraction of hinoki essential oils. As a control method, organic solvent extraction was performed using either hexane, ethyl acetate (EtOAc), or acetone at 30 °C for 1 h. Both the experimental and control methods were conducted under the same conditions, which relied on partial dissolution of the leaves using the IL and DESs before partitioning the hinoki oils into the organic solvent for analysis. Quantitative analysis was performed using gas chromatography–mass spectrometry (GC-MS) in selected ion monitoring (SIM) mode. The results indicated that extraction using the [C2mim][(MeO)(H)PO2]/acetone bilayer system improved the yields of limonene and hibaene, 1.5- and 1.9-fold, respectively, when compared with the control method. In addition, extraction using betaine/l-lactic acid (molar ratio 1:1) gave the greatest yields for both limonene and hibaene, 1.3-fold and 1.5-fold greater, respectively, than when using an organic solvent. These results demonstrate the effective extraction of essential oils from plant leaves under conditions milder than those needed for the conventional method. The less toxic and environmentally begin DESs for the extraction are also applicable to the food and cosmetic industries.

scholarly journals Pemanfaatan Hidrofobik Deep Eutectic Solvents dalam Penyisihan Dimetoat, Klorpirifos, dan Profenofos pada Buah Tomat dan Sayur Brokoli

2020 ◽  
Vol 9 (1) ◽  
pp. 7-10
Author(s):  
Axel Try Iddo Daely ◽  
Renita Manurung
Keyword(s):  
Lauric Acid ◽  
Freezing Point ◽  
Deep Eutectic Solvent ◽  
Chemical Properties ◽  
Deep Eutectic Solvents ◽  
Extraction Process ◽  
Molar Ratio ◽  
Organophosphate Insecticide ◽  
Pesticide Removal ◽  
New Generation

Organophosphate insecticide is a type of pesticide that is commonly used, where this pesticide can be toxic to environmental organisms even to humans. Hydrophobic Deep Eutectic Solvent (DES) is a new generation nonpolar solvent of ionic liquids because it has better physical properties and chemical properties so that it can be used in the extraction process. DES was synthesized at 50 oC for 15 minutes with a stirring speed of 300 rpm and a molar ratio of Dl-menthol: lauric acid varied from 1: 1, 2: 1, and 3: 1. Pesticide removal is done by mixing 5 ml of DES with 200 ml of aquadest and then Tomatoes and Broccoli vegetables are washed with the solution. DES characteristics are done by analyzing the shape and measuring the freezing point, density and viscosity of DES. The concentration of pesticide residues was analyzed using Gas Chromatography-Mass Spectrometer (GC-MS). The highest elimination of pesticides obtained with DES hydrophobic which has a molar ratio of dl-menthol: lauric acid is 3: 1 where the highest elimination of pesticides in Tomatoe is 44.82% for Dimethoate pesticide, 84.1% for Chlorpyrifos pesticide, and 83.72% for Profenofos pesticide and Broccoli 35.19% for Dimetoat pesticide, 64.64% for Chlorpyrifos pesticide, and 55.28% for Profenofos pesticides.

scholarly journals Enhanced Furfural Production in Deep Eutectic Solvents Comprising Alkali Metal Halides as Additives

Molecules ◽  
2021 ◽  
Vol 26 (23) ◽  
pp. 7374
Author(s):  
Eduarda S. Morais ◽  
Mara G. Freire ◽  
Carmen S. R. Freire ◽  
Armando J. D. Silvestre
Keyword(s):  
Alkali Metal ◽  
Lithium Bromide ◽  
Deep Eutectic Solvent ◽  
Deep Eutectic Solvents ◽  
Operating Conditions ◽  
Molar Ratio ◽  
Metal Halides ◽  
Promising Alternative ◽  
Operational Conditions ◽  
Alkali Metal Halides

The addition of alkali metal halide salts to acidic deep eutectic solvents is here reported as an effective way of boosting xylan conversion into furfural. These salts promote an increase in xylose dehydration due to the cation and anion interactions with the solvent being a promising alternative to the use of harsh operational conditions. Several alkali metal halides were used as additives in the DES composed of cholinium chloride and malic acid ([Ch]Cl:Mal) in a molar ratio of 1:3, with 5 wt.% of water. These mixtures were then used as both solvent and catalyst to produce furfural directly from xylan through microwave-assisted reactions. Preliminary assays were carried out at 150 and 130 °C to gauge the effect of the different salts in furfural yields. A Response Surface Methodology was then applied to optimize the operational conditions. After an optimization of the different operating conditions, a maximum furfural yield of 89.46 ± 0.33% was achieved using 8.19% of lithium bromide in [Ch]Cl:Mal, 1:3; 5 wt.% water, at 157.3 °C and 1.74 min of reaction time. The used deep eutectic solvent and salt were recovered and reused three times, with 79.7% yield in the third cycle, and the furfural and solvent integrity confirmed.

scholarly journals Structural and Transport Properties of Binary Mixtures of Deep Eutectic Solvent (Ethaline) with Primary Alcohols: A Molecular Dynamics Study

2021 ◽  
Author(s):  
kishant kumar ◽  
Anand Bharti ◽  
Aditya Sinha
Keyword(s):  
Molecular Dynamics ◽  
Transport Properties ◽  
Binary Mixtures ◽  
Choline Chloride ◽  
Deep Eutectic Solvent ◽  
Deep Eutectic Solvents ◽  
Md Simulations ◽  
Molar Ratio ◽  
Green Solvents ◽  
Primary Alcohols

<table><tr><td>Deep eutectic solvents (DESs) are classified as the green solvents which are considered as an alternative to volatile organic solvents. In this work, the thermophysical, structural and transport properties of binary mixtures of DES ethaline (choline chloride (ChCl) + ethylene glycol (etgly) at a molar ratio of 1:2) with primary alcohols (methanol/ethanol) are studied using molecular dynamics (MD) simulations</td></tr></table> <br>

Investigation of a deep eutectic solvent formed by levulinic acid with quaternary ammonium salt as an efficient SO2 absorbent

2015 ◽  
Vol 39 (10) ◽  
pp. 8158-8164 ◽  
Author(s):  
Dongshun Deng ◽  
Guoqiang Han ◽  
Yaotai Jiang
Keyword(s):  
Ammonium Salt ◽  
Quaternary Ammonium ◽  
Quaternary Ammonium Salt ◽  
Levulinic Acid ◽  
Deep Eutectic Solvent ◽  
Deep Eutectic Solvents ◽  
Separation Performance

Six new deep eutectic solvents with good absorption and separation performance for SO2 were developed.

scholarly journals Separation of Benzene-Cyclohexane Azeotropes Via Extractive Distillation Using Deep Eutectic Solvents as Entrainers

Processes ◽  
2021 ◽  
Vol 9 (2) ◽  
pp. 336
Author(s):  
Fang Bai ◽  
Chao Hua ◽  
Jing Li
Keyword(s):  
Atmospheric Pressure ◽  
Levulinic Acid ◽  
Petrochemical Industry ◽  
Choline Chloride ◽  
Tetrabutylammonium Bromide ◽  
Deep Eutectic Solvents ◽  
Extractive Distillation ◽  
Liquid Equilibrium ◽  
Ft Ir ◽  
Modelling Approach

The separation of benzene and cyclohexane azeotrope is one of the most challenging processes in the petrochemical industry. In this paper, deep eutectic solvents (DES) were used as solvents for the separation of benzene and cyclohexane. DES1 (1:2 mix of tetrabutylammonium bromide (TBAB) and levulinic acid (LA)), DES2 (1:2 mix of TBAB and ethylene glycol (EG)) and DES3 (1:2 mix of ChCl (choline chloride) and LA) were used as entrainers, and vapor-liquid equilibrium (VLE) measurements at atmospheric pressure revealed that a DES comprised of a 2:1 ratio of LA and TBAB could break this azeotrope with relative volatility (αij) up to 4.763. Correlation index suggested that the NRTL modelling approach fitted the experimental data very well. Mechanism of extractive distillation gained from FT-IR revealed that with hydrogen bonding and π–π bond interactions between levulinic acid and benzene could be responsible for the ability of this entrainer to break the azeotrope.

scholarly journals Enzymatic Polymerization of Dihydroquercetin (Taxifolin) in Betaine-Based Deep Eutectic Solvent and Product Characterization

Catalysts ◽  
2021 ◽  
Vol 11 (5) ◽  
pp. 639
Author(s):  
Maria Khlupova ◽  
Irina Vasil’eva ◽  
Galina Shumakovich ◽  
Elena Zaitseva ◽  
Vyacheslav Chertkov ◽  
...  
Keyword(s):  
Average Molecular Weight ◽  
Deep Eutectic Solvent ◽  
Linear Structure ◽  
Deep Eutectic Solvents ◽  
Enzymatic Polymerization ◽  
Molar Ratio ◽  
Average Chain Length ◽  
Trametes Hirsuta ◽  
Synthetic Reactions ◽  
Buffer Mixture

Deep eutectic solvents (DESs) are an alternative to conventional organic solvents in various biocatalytic reactions. Meanwhile, there have been few studies reporting on synthetic reactions in DESs or DES-containing mixtures involving oxidoreductases. In this work, we have studied the effects of several DESs based on betaine as the acceptor of hydrogen bonds on the catalytic activity and stability of laccase from the basidial fungus Trametes hirsuta and performed enzymatic polymerization of the flavonoid dihydroquercetin (DHQ, taxifolin) in a DES–buffer mixture containing 60 vol.% of betaine-glycerol DES (molar ratio 1:2). The use of the laccase redox mediator TEMPO enabled an increased yield of DHQ oligomers (oligoDHQ), with a number average molecular weight of 1800 g mol−1 and a polydispersity index of 1.09. The structure of the synthesized product was studied using different physicochemical methods. NMR spectroscopy showed that oligoDHQ had a linear structure with an average chain length of 6 monomers. A scheme for enzymatic polymerization of DHQ in a DES–buffer mixture was also proposed.

scholarly journals Synthesis of various 2-benzylbenzoxazole derivatives catalyzed by deep eutectic solvent-supported onto magnetic nanoparticles

2020 ◽  
Vol 4 (3) ◽  
pp. First
Author(s):  
The Thai Nguyen ◽  
Phuong Hoang Tran
Keyword(s):  
Magnetic Nanoparticles ◽  
Magnetic Nanoparticle ◽  
Fourier Transforms ◽  
Condensation Reaction ◽  
Deep Eutectic Solvent ◽  
Deep Eutectic Solvents ◽  
Significant Loss ◽  
Molar Ratio ◽  
Efficient Catalyst ◽  
X Ray

Magnetic nanoparticle supported deep eutectic solvents have been synthesized by preparing and grafting [Urea]4[ZnCl2] deep eutectic solvent onto the surface of silica-coated Fe3O4 magnetic nanoparticles using 3‐ chloropropyltrimethoxysilane as a linker. DES@MNP was fully characterized using scanning and transmission electron microscopies, Fourier transforms infrared, energy-dispersive X-ray spectroscopies, vibrating sample magnetometer X-ray diffraction, and thermogravimetric analysis. In this study, we have developed the synthesis of 2-benzylbenzoxazole via condensation reaction of 2-nitrophenols and acetophenones using a magnetic nanoparticle supported [Urea]4[ZnCl2] deep eutectic solvent as a novel, green and efficient catalyst. In the presence of 1,4-diazabicyclo[2.2.2]-octane, elemental sulfur acted as an excellent reductant in promoting oxidative rearranging coupling in this reaction. The reaction has been conducted via the stirring method and the reaction conditions were surveyed (16 h, 130 °C, acetophenone, 2-nitrophenol, DABCO and sulfur molar ratio of 2:1:1:3, 10 mol% DES@MNP catalyst). Six 2-benzylbenzoxazole derivatives have been synthesized via this method with good yield (86-91%). The structure of the pure product has been confirmed through FT-IR, 1H NMR, 13C NMR, and GC-MS methods. More importantly, DES@MNP has been separated from the reaction mixture by a magnet and reused over five consecutive runs without significant loss of catalytic activity.

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